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Constituyentes de los aceites esenciales de Baccharis trinervis (Asteraceae) de Costa Rica.

Essential oils of Baccharis trinervis (Asteraceae) from Costa Rica.

Baccharis L. is one of the largest genera within Asteraceae family (tribe Astereae, sub-tribe Baccharidinae) including herbaceous perennials, vines, shrubs and trees. This genus includes ca. 340 to 400 species ranging from the Southern United States to the Southern extreme of Argentina and Chile through Central America and the Caribbean basin (Heiden, Andrade-Baumgratz, & Esteves, 2012). Some of the species are economically important as medicinals--used mainly as infusions and decoctions--for treat stomach and liver ailments, inflammations, anemia, diabetes and prostate diseases (Verdi, Brighente, & Pizzolatti, 2005). The vassoura essential oil (Baccharis dracunculifolia DC.) and carqueja oil [B. genistelloides (Lam.) Pers.] are used in perfume industry (Ferracini et al., 1995).

Baccharis trinervis Pers. [=Pseudobaccharis trinervis (Pers.) V M. Badillo] is a common shrub or sub-scandent shrub in the Pacific slope of Costa Rica, with hairless ribbed stems and oblong-elliptic or lanceolate-elliptic alternate leaves, 3 to 10 cm long, 1.5 to 3.5 cm wide, hard and rough, with three prominent, longitudinal veins, puberulent to pilose on both sides. Flowers are greenish-white disposed in terminal panicles (Leon & Poveda, 2000) situated within or overtopping the foliage. This plant has a wide distribution, from Mexico, Central America and throughout South America. In Costa Rica it is distributed over the country, from lowlands to 1 900 m of elevation, in both dry and wet forests. This plant is commonly known as alcotan, and in the Northwestern Guanacaste Province it is known as jalapatras and rastrapo (Leon & Poveda, 2000). In Costa Rica, the fresh leaves are used as a poultice on wounds and ulcers (Pittier, 1978) and the alcoholic extracts of roots are said to be used as remedy for snakebites (Nunez-Melendez, 1978). In Honduras, the extracted juice of the leaf, and root decoctions, are taken as a remedy for kidney troubles, pain and inflammations, as a febrifuge, for halting diarrhea, and against rheumatic pains (House et al., 1995). It has also been used in various liver diseases, as a purgative, antiseptic, digestive and diuretic, in rectal washes against hemorrhoids and as a remedy for typhoid fever (Ramirez-Cardenas, IsazaMejia, & Perez-Cardenas, 2013).

Many phytochemical investigations have been performed on plants of the Baccharis genus and are characterized by the occurrence of flavonoids, diterpenoids (the most prominent classes are clerodanes and labdanes, and with some frequency, kauranes), triterpenes, phenolic compounds, and particularly important is the occurrence of essential oils (Verdi et al., 2005; Abad & Bermejo, 2007; Ramos Campos et al., 2016). From the aerial parts of Baccharis trinervis, Bohlmann and Zdero (1970) reported the presence of matricaria ester, and three C-17 esters with an ene-diyne-diene-structure. From air-dried aerial parts (from Brazil) were obtained the terpenoids phytene, caryophyllene, germacrene D, bicyclogermacrene, [alpha]- and [gamma]-humulene, squalene, lupeyl acetate, lupeol, [beta]-amyrin and the diacetylenic compound lachnophyllum ester (Bohlmann, Kramp, Grenz, Robinson, & King, 1981), whereas the study of Kuroyanagi, Uchida, Ueno, Satake, and Shimomura (1993) afforded 24 neo-clerodane type diterpenes, many of them new. Also, Herrera, Rosas-Romero, Crescente, Acosta, and Pekerar (1996) reported several 5-hydroxy 7-methoxyflavones from leaves, and Sharp et al. (2001) reported three 6-oxigenated flavones from branches.

Regarding biological activities attributed to this species there are some reports about antioxidant activity of the ethanolic extract (Heras et al., 1998), antiviral activity against herpes simplex type I (HSV-1), vesicular stomatitis virus (VSV-1) and poliovirus type I (Abad, Bermejo, Sanchez-Palomino, Chiriboga, & Carrasco, 1999), anti-HIV activity in macrophages (Sanchez-Palomino et al., 2002), antimicrobial activity (Albuquerque et al., 2004), and antioxidant, antifungal and hemolytic activities of the essential oil (Sobrinho et al., 2016).

In relation to the essential oil composition of the aerial parts of this species, there are only three previous reports: two studies from material collected in the state of Ceara, Northeast Brazil (Albuquerque et al., 2004; Sobrinho et al., 2016), and another from the state of Merida, Venezuela (Rojas et al., 2008).

The objective of the present research was the characterization of the chemical composition of seven different samples of essential oils from diverse morphological parts of B. trinervis collected in three different locations in central Costa Rica. To the best of our knowledge, no previous chemical work on B. trinervis from Costa Rica has been reported.

MATERIALS AND METHODS

Plant material: The aerial parts of Baccharis trinervis were collected from three localities of Costa Rica: Miramar, Montes de Oro mountains (west central Pacific), Province of Puntarenas (10[degrees]06'12.79" N - 84[degrees]42'26.09" W, at an elevation of 750 m), on April 2009, during the flowering stage; in the University of Costa Rica Campus, San Pedro de Montes de Oca, Province of San Jose (9[degrees]56'14.60" N - 84[degrees]02'51.51" W, at 1 210 m elevation), on February 2009, during vegetative stage, and Pavas, Province of San Jose (9[degrees]56'37.20" N - 84[degrees]06'59.40" W, at an elevation of 1 093 m) on November 2015, during the flowering stage of the plant. A voucher specimen has been deposited in the Herbarium of the University of Costa Rica at the School of Biology (USJ 93916).

Isolation of the essential oils: Plant materials were hydrodistilled at atmospheric pressure, for 3 h, using a Clevenger-type apparatus. The distilled oils were collected and dried over anhydrous sodium sulfate, filtered and stored at 0-10[degrees]C in the dark, for further analysis. The essential oil yields (v/w) from diverse morphological parts from three localities in central Costa Rica were: Miramar sample, 0.32 % (leaf), 0.04 % (flower); San Pedro sample, 0.35 % (leaf), 0.03 % (branch); and Pavas sample, 0.23 % (leaf), 0.06 % (flower), and 0.05 % (branch).

Gas chromatographic (GC-FID) analyses: The oils of Baccharis trinervis were analyzed using a Shimadzu GC-2014 gas chromatograph. The data were obtained on a 5 % phenyl/dimethylpolysiloxane column (30 m x 0.25 mm; film thickness 0.25 pm), (MDN-5S, Supelco), with a Shimadzu GCsolution Chromatography Data System, Shimadzu GC Solution, Chromatography Data System, software version 2.3. The experimental conditions were: carrier gas [N.sub.2], flow 1.0 mL/min; oven temperature program: 60 to 280[degrees]C at 3[degrees]C/min, 280[degrees]C (2 min); sample injection port temperature 250[degrees]C; detector temperature 280[degrees]C; split 1:60.

Gas chromatography-mass spectrom etry (GC-MS): The analyses were performed using a Shimadzu GC-17A gas chromatograph coupled with a GCMS-QP5000 apparatus and CLASS 5000 software with Wiley 139 and NIST computer databases. The data were obtained on a MDN-5S column (30 m x 0.25 mm), coated with 5 % phenyl/dimethyl-polysiloxane (film thickness 0.25 [micro]m). Experimental conditions were: carrier gas He, flow 1.0 mL/min; oven temperature program: 60 to 280[degrees]C at 3[degrees]C/min; sample injection port temperature 250[degrees]C; detector temperature 260[degrees]C; ionization voltage: 70 eV; ionization current 60 pA; scanning speed 0.5 s over 38 to 400 amu range; split 1:70.

Compound identification and quantification: The components of the oils were identified by comparison of their linear retention indices which were calculated in relation to a homologous series of n-alkanes, on 5 % phenyl/ dimethylpolysiloxane type column (van den Dool & Kratz, 1963), and by comparison of their mass spectral fragmentation patterns with those published in the literature (Adams, 2007) or those of our own database. To obtain the retention indices for each peak, 0.1[micro]L of n-alkane mixture (Sigma, [C.sub.8] to [C.sub.32] standard mixture) was injected under the same experimental conditions reported above. Integration of the total chromatogram (GC-FID), expressed as area percent, has been used to obtain quantitative compositional data without FID response factor correction.

RESULTS

The essential oils from different parts of Baccharis trinervis from Costa Rica presented a very complex chemical profile. The compounds identified, their experimental retention indices (RI) determined in relation to a homologous series of linear alkanes ([C.sub.8] to [C.sub.32]), their relative percentage concentrations, and the method used for their identification are presented in table 1. The constituents are listed in order of elution on a MDN-5S column and for comparison purposes, previously published values of the retention indices are included (Lit. RI). Compounds identified in this study and previously reported in the Venezuelan and Brazilian essential oil samples are indicated by bullets and/or asterisks.

Baccharis trinervis gave essential oils which were predominantly terpenoid in nature with a few aliphatic and aromatic compounds as minor and trace constituents. In table 2, the percentages of the various classes of constituents of the essential oils are indicated. In total, 268 compounds were identified by means of GC-FID and GC-MS techniques, which represented 95.6 to 98.6 % of the total essential oil compositions.

Samples of the species were gathered in three different Costa Rican locations, showing qualitative similarities, but some major quantitative differences. The leaf essential oil obtained from Miramar was dominated by oxygenated sesquiterpenes (64.6 %), with caryophyllene oxide (22.5 %) (Fig. 1), viridiflorol (20.3 %) and spathulenol (8.3 %) as principal components, accompanied by lesser amounts in the 1.53.9 % range, namely a-pinene, [beta]-caryophyllene, cubebol, humulene epoxide II, 1-epi-cubenol, [delta]-3-carene, ar-curcumene, cis-cadin-4-en-7-ol, [beta]-pinene, and [gamma]-curcumene. The main constituents of the leaf essential oil from San Pedro were germacrene D (19.1 %), germacrene B (16.0 %), [beta]-caryophyllene (9.1 %), viridiflorol (8.8 %), and [delta]-3-carene (6.8 %). Other significant constituents in the 1.3-3.4 % range were [delta]-cadinene, [alpha]-pinene, [beta]-elemene, [gamma]-elemene, [beta]-phellandrene, [alpha]-thujene, and [beta]-pinene. The main components of Pavas leaf essential oil were viridiflorol (21.0 %), [beta]-caryophyllene (7.9 %), [delta]-3-carene (6.6 %), germacrene D (6.3 %), and a-pinene (5.9 %). These compounds were accompanied by other significant constituents in the 1.4-3.0 % range, namely [beta]-elemene, spathulenol, limonene, [beta]-pinene, bicyclogermacrene, [alpha]-cadinol, caryophyllene oxide, [alpha]-thujene, sabinene, [gamma]-muurolene, [delta]-cadinene, and germacrene B.

The composition of the flower essential oil obtained from samples collected in the localities of Miramar and Pavas were dominated by sesquiterpenoids (86.6 %) with cis-muurola-4(14),5-diene (13.7 %), [beta]-caryophyllene (9.5 %), bicyclogermacrene (8.3 %), and arcurcumene (8.0 %) as major constituents, accompanied by lesser amounts of several compounds in the 2.2-4.7 % range, namely viridiflorol, germacrene D, germacrene B, spathulenol, cis-cadin-4-en-7-ol, [gamma]-cadinene, [beta]-elemene, and humulene or globulol (24.8 %), [beta]-caryophyllene (17.1 %), germacrene D (9.9 %), bicyclogermacrene (5.9 %), spathulenol (4.8 %), caryophyllene oxide (4.7 %), and [beta]-elemene (4.3 %). The branch essential oil from San Pedro sample also was constituted mainly by sesquiterpenoids (87.4 %) with germacrene B (18.7 %), germacrene D (14.7 %), [beta]-caryophyllene (12.4 %) and globulol (11.3 %) as main constituents. There were also lesser amounts of several compounds in the 2.2-4.3 % range, namely [delta]-cadinene, bicyclogermacrene, [beta]-copaene, [beta]-elemene, and [delta]-3-carene. The branch essential oil from Pavas sample was constituted mainly by sesquiterpenoids (67.1 %) with more quantity of monoterpenoids (27.8 %) than the sample from San Pedro (10.4 %). The main compounds were germacrene D (15.6 %), viridiflorol (11.5 %), [beta]-caryophyllene (10.1 %), [delta]-3-carene (8.1 %), [beta]-phellandrene (6.5 %), bicyclogermacrene (4.9 %), and [delta]-cadinene (3.5 %).

As can be seen from table 1 and table 2, the major constituents of the leaf essential oil from the sample collected in Miramar were oxygenated sesquiterpenes (64.6 %), whereas sesquiterpene hydrocarbons (64.3 %) were the major components of the San Pedro sample. However, in the sample from Pavas, the two cited classes of metabolites were almost equally distributed (30.7 and 33.6 %, respectively).

DISCUSSION

The essential oil of fresh aerial parts of Baccharis trinervis, collected on Merouca mountain region of Ceara state, Northeastern Brazil (Albuquerque et al., 2004; Sobrinho et al., 2016), revealed that the major constituents were terpenoids with the presence of [beta]-phellandrene (18.4-27.8 %), sabinene (10.914.2 %), [alpha]-thujene (6.6-10.5 %), (Z)-pocimene (2.3-8.1 %), [alpha]-pinene (5.5-8.7 %), and (E)-[beta]-ocimene (1.9-6.3 %), including two non-terpenoid C-10 ene-diyne esters: methyl (Z)-dec-2-en-4,6-diynoate (0.8-14.6 %) and methyl (E)-dec-2-en-4,6-diynoate (10.7-14.7 %) not found in other oils of Baccharis species studied up to day. Rojas et al. (2008) examined the essential oil from leaves collected on Santa Rosa, La Hechicera, in Merida State (Venezuela). In this study, the authors reported that the major constituents were germacrene D (20.1 %), limonene (15.0 %), [delta]-cadinene (5.2 %), [beta]-caryophyllene (4.8 %), [alpha]-pinene (4.5 %), and bicyclogermacrene (4.0 %), and this oil can be distinguished from the Brazilian ones in the fact that the main C-10 ene-diyne esters were absent. Our experimental data support those obtained by Rojas et al. (2008) because the results of the essential oil samples from the three different locations in Costa Rica do not contain those characteristic and very specific C-10 ene-diyne esters found in the Brazilian botanical material. As an additional support, the phytochemical study realized by Bohlmann and Zdero (1970) of fresh aerial parts of B. trinervis, cultured from seeds -of not specified origin- at Botanical Garden of the University of Berkeley, verified the presence of matricaria ester and three C-17 ene-diyne-diene esters but not C-10 ene-diyne esters (see also, Bohlmann, Burkhardt, & Zdero, 1973). Nonetheless, in a later phytochemical study of nine species of Baccharis collected in Brazil, the aerial parts of B. trinervis afforded, besides several terpenoids, one compound which has the trivial name lachnophyllum ester (probably, its Z isomer) corresponding to methyl dec-2-en-4,6-diynoate (Bohlmann et al., 1981). This was the first diacetylenic compound with established chemical constitution isolated from an essential oil (Serensen, 1977). This significant variation in the qualitative composition of the essential oils of the same species collected in Venezuela and Costa Rica compared with the Brazilian samples could be caused by the habitat and environment factors as well as the genotype of the plant, but real sources of variability, according to Nemeth-Zamborine (2016), are 'hard to determine'. Furthermore, it is known that Baccharis is a diverse and complex genus of the Asteraceae because some of the species present a high degree of morphological and chemical variability. One of the distinguishing factors of the oils from this plant growing wild in Costa Rica is the presence of an array of terpenoids with diverse carbon skeletons that could arise through various biosynthetic patterns. Especially important in number are the cadinane class and the guaiane family of sesquiterpenoids that are originated from the germacrane biosynthetic pathway. A distinctive character of the oils of B. trinervis studied from Costa Rica is the presence of the oxygenated sesquiterpenoids spathulenol, viridiflorol and globulol, in important amounts, accompanied by lesser quantities of several compounds of the same carbon skeleton, that are not found in the Venezuelan sample nor in the oils of Brazilian botanical material. These compounds also were found in B. articulata (Lam.) Pers. (Minteguiaga et al., 2015), B. caprariifolia DC. (Ferracini et al., 1995), B. crispa Spreng. (Simoes-Pires et al., 2005), B. dracunculifolia DC. (Frizzo et al., 2008; Fabiane, Ferronatto, dos Santos, & Onofre, 2008), B. erioclada DC. (Ferracini et al., 1995), B. platipoda DC. (Ferracini et al., 1995; Quiroga, Ferracini, & Marsaioli, 1996), B. semiserrata DC. (Vannini et al., 2012), B. tridentata Vahl (Ferracini et al., 1995; Quiroga et al., 1996), B. trimera (Less.) DC. (Silva et al., 2007; Oliveira et al., 2012), B. uncinella (Fabiane et al., 2008), and B. vincaefolia Baker (Ferracini et al., 1995). Spathulenol appear to be a widespread compound in the essential oils from plants of the genus Baccharis. Our findings corroborate the presence of 41 compounds previously reported (Albuquerque et al., 2004; Sobrinho et al., 2016; Rojas et al., 2008) indicated by asterisks and bullets in table 1, whereas 227 constituents are newly reported in the composition of oils from Baccharis trinervis.

The aerial parts of Baccharis trinervis growing wild in Costa Rica produce terpenoid-rich essential oils whose compositions were dominated by either globulol (0-24.8 %), caryophyllene oxide (0.1-22.5 %), viridiflorol (0-21.0 %), germacrene D (0.5-19.1 %), germacrene B (0.2-18.7 %), [beta]-caryophyllene (3.517.1 %), cis-muurola-4(14),5-diene (0-13.7 %), bicyclogermacrene (0-8.3 %), spathulenol (0.18.3 %), ar-curcumene (0-8.0 %), [delta]-3-carene (0.9-6.8 %), or [alpha]-pinene (0.3-5.9 %), according to the morphological part studied or the locality of collection of the sample. The composition of the essential oils of B. trinervis from central Costa Rica is qualitatively different to the composition of the oils from samples of the same species collected in the state of Ceara, Brazil, which contain two characteristic stereoisomeric lachnophyllum esters, compounds not detected in this study. The essential oils of plants from Costa Rica resemble the composition of the oil from Venezuelan origin, but differ from both Brazilian and Venezuelan essential oils by the presence of sesquiterpenoids of the guaiane carbon skeleton, some of them as prominent members: viridiflorol, globulol, and spathulenol.

ACKNOWLEDGMENTS

The authors are grateful to Escuela de Quimica and Vicerrectoria de Investigacion (UCR) for financial support (Project No. 809B1-190) and to C. O. Morales (Biology School, UCR) for the species identification.

REFERENCES

Abad, M. J., Bermejo, P., Sanchez-Palomino, S., Chiriboga, X., & Carrasco, L. (1999). Antiviral activity of some South American medicinal plants. Phytothera py Research, 13, 142-146.

Abad, M. J., & Bermejo, P. (2007). Baccharis (Compositae): a review update. ARKIVOC, Part (vii), 76-96.

Adams R. P. (2007). Identification of Essential Oil Components by Gas Chromatography / Mass Spectrometry (4th ed). Carol Stream, Illinois: Allured Publishing Corporation.

Ali, N. A. A., Wurster, M., Arnold, N., Teichert, A., Schmidt, J., Lindequist, U., & Wessjohann, L. (2008). Chemical composition and biological activities of essential oils from the oleogum resins of three endemic soqotraen Boswellia species. Records of Natural Products, 2(1), 6-12.

Albuquerque, M. R. J. R., Souza, E. B., Lins, M. U. D. S., Nogueira, N. A. P., Lemos, T. L. G., Silveira, E. R., & Pessoa, O. D. L. (2004). Composition and antimicrobial activity of the essential oil from aerial parts of Baccharis trinervis (Lam.) Pers. ARKIVOC, Part (vi), 59-65.

Bohlmann, F., & Zdero, C. (1970). Polyacetylenverbindungen. 179. Uber die Inhaltsstoffe von Baccharis trinervis Pers. Chemische Berichte, 103(8), 2327-2329.

Bohlmann, F., Burkhardt, T., & Zdero, C. (1973). Naturally occurring acetylenes (pp. 215-217). London: Academic Press.

Bohlmann, F., Kramp, W., Grenz, M., Robinson, H., & King, R. M. (1981). Diterpenes from Baccharis species. Phytochemistry, 20(8), 1907-1913.

Ferracini, V. L., Paraiba, L. C., Leitao Filho, H. F., da Silva, A. G., Nascimento, L. R., & Marsaioli, A. J. (1995). Essential oils of seven Brazilian Baccharis species. Journal of Essential Oil Research, 7(4), 355-67.

Fabiane, K. C., Ferronatto, R., dos Santos, A. C., & Onofre, S. B. (2008). Physicochemical characteristics of the essential oils of Baccharis dracunculifolia and Baccharis uncinella DC. (Asteraceae). Revista Brasileira de Farmacognosia, 18(2), 197-203.

Flamini, G., Cioni, P. L, Morelli, I., Ceccarini L., Andolfi, L., & Macchia, M. (2003). Composition of the essential oil of Medicago marina L. from the coastal dunes of Tuscany, Italy. Flavour and Fragrance Journal, 18, 460-462.

Frizzo, C. D., Atti-Serafini, L., Laguna, S. E., Cassel, E., Lorenzo, D., & Dellacassa, E. (2008). Essential oil variability in Baccharis uncinella DC and Baccharis dracunculifolia DC growing wild in southern Brazil, Bolivia and Uruguay. Flavour and Fragrance Journal, 23(2), 99-106.

Heiden, G., Andrade-Baumgratz, J. F., & Esteves, R. L. (2012). Baccharis subgen. Molina (Asteraceae) no estado do Rio de Janeiro, Brasil. Rodriguesia, 63(3), 649-687.

Heras, B., Slowing, K., Benedi, J., Carretero, E., Ortega, T., Toledo, C., Bermejo, P., ..., & Villar, A. (1998). Antiinflammatory and antioxidant activity of plants used in traditional medicine in Ecuador. Journal of Ethnopharmacology, 61, 161-166.

Herrera, J. C., Rosas-Romero, A. J., Crescente, O. E., Acosta, M., & Pekerar, S. (1996). Analysis of 5-hydroxy-7-methoxyflavones by normal-phase high-performance liquid chromatography. Journal of Chromatography A, 740, 201-206.

House, P. R., Lagos-Witte, S., Ochoa, L., Torres, C., Mejia, T., & Rivas, M. (1995). Plantas medicinales comunes de Honduras (pp. 50-51). Tegucigalpa, Honduras: UNAH, CIMN-H, CID/CIIR, GTZ.

Jordan, M. J., Margaria, C. C., Shaw, P. E., & Goodner, K. L. (2002). Aroma active components in aqueous Kiwi fruit essence and Kiwi fruit puree by GC-MS and multidimensional GC/GC-O. Journal of Agricultural and Food Chemistry, 50, 5386-5390.

Kuroyanagi, M., Uchida, K., Ueno, A., Satake, M., & Shimomura, K. (1993). Neo-clerodane type diterpenes from Baccharis trinervis. Phytochemistry, 34(5), 1377-1384.

Leon, J., & Poveda, L. J. (2000). In P. E. Sanchez-Vindas (Ed.), Nombres comunes de las plantas en Costa Rica (pp. 48). San Jose, Costa Rica: Editorial Guayacan.

Minteguiaga, M., Umpierrez, N., Farina, L., Falcao, M. A., Xavier, V. B., Cassel, E., & Dellacassa, E. (2015). Impact of gas chromatography and mass spectrometry combined with gas chromatography and olfactometry for the sex differentiation of Baccharis articulata by the analysis of volatile compounds. Journal of Separation Science, 38(17), 2931-3118.

Nemeth-Zamborine, E. (2016). Natural variability of essential oil components. In K. H. C. Bacir, & G. Buchbauer (Eds.). Handbook of essential oils: Science, technology, and applications (pp. 87-125). Boca Raton, FL: CRC Press/Taylor & Francis.

Nunez-Melendez, E. (1978). Plantas medicinales de Costa Rica y su folklore. San Jose, Costa Rica: Editorial Universidad de Costa Rica.

Oliveira, R. N., Rehder, V. L., Oliveira, A. S. S., Junior, I. M., de Carvalho, J. E., de Ruiz, A. L. T., Jeraldo, V. L. S., Linhares, A. X., & Allegretti, S. M. (2012). Schistosoma mansoni: In vitro schistosomicidal activity of essential oil of Baccharis trimera (Less.) DC. Experimental Parasitology, 132, 135-143.

Pittier, H. (1978). Plantas usuales de Costa Rica (reprint of 2nd ed., 1957). San Jose, Costa Rica: Editorial Costa Rica.

Quiroga, C. L., Ferracini, V. L., & Marsaioli, A. J. (1996). Three new oxigenated cadinanes from Baccharis Species. Phytochemistry, 42(4), 1097-1103.

Radulovic, N. S., Dordevic, N. D., & Palic, R. (2010). Volatile of Pleurospermim austriacum (L.) Hoffm. (Apiaceae). Journal of Serbian Chemical Society, 75(12), 1-11.

Ramirez-Cardenas, A., Isaza-Mejia, G. & Perez-Cardenas, J. E. (2013). Especies vegetales investigadas por sus propiedades antimicrobianas, inmunomoduladoras e hipoglicemientes en el Departamento de Caldas (Colombia, Sudamerica). Biosalud, 12(1), 59-82.

Ramos Campos, F., Bressan, J., Godoy Jasinski, V. C., Zuccolotto, T., da Silva, L. E., & Bonancio Cerqueira, L. (2016). Baccharis (Asteraceae): Chemical constituents and biological activities. Chemistry and Biodiversity, 13, 1-17.

Rojas, J., Velasco, J., Morales, A., Rojas, L., Diaz, T., Rondon, M., & Carmona, J. (2008). Chemical composition and antibacterial activity of the essential oil of Baccharis trinervis (Lam.) Pers. (Asteraceae) collected in Venezuela. Natural Product Communications, 3(3), 369-372.

Sanchez-Palomino, S., Abad, M. J., Bedoya, L. M., Garcia, J., Gonzales, E., Chiriboga, X., Bermejo, P., & Alcami, J. (2002). Screening of South American plants against human immunodeficiency virus: Preliminary fractionation of aqueous extract from Baccharis trinervis. Biological and Pharmaceutical Bulletin, 25, 1147-1150.

Sharp, H., Bartholomew, B., Bright, C., Latif, Z., Sarker, S. D., & Nash, R. J. (2001). 6-Oxygenated flavones from Baccharis trinervis (Asteraceae). Biochemical Systematics and Ecology, 29, 105-107.

Silva, F. G., Oliveira, C. B. A., Pinto, J. E. B. P., Nascimento, V. E., Santos, S. C., Seraphin, J. C., & Ferri, P. H. (2007). Seasonal variability in the essential oils of wild and cultivated Baccharis trimera. Journal of the Brazilian Chemical Society, 18(5), 990-997.

Simoes-Pires, C. A., Debenedetti, S., Spegazzini, E., Mentz, L. A., Matzenbacher, N. I., Limberger, R. P., & Henriques, A. T. (2005). Investigation of the essential oil from eight species of Baccharis belonging to sect. Caulopterae (Asteraceae, Astereae): a taxonomic approach. Plant Systematics and Evolution, 253, 23-32.

Sobrinho, C. A. N., Souza, E. B., Rocha, M. F. G., Albuquerque, M. R. J. R., Bandeira, P. N., Santos, H. S., Cavalcante, C. S. P., ..., & Fontenelle, R. O. S. (2016). Chemical composition, antioxidant, antifungal and hemolytic activities of essential oil from Baccharis trinervis (Lam.) Pers. (Asteraceae). Industrial Crops and Products, 84,108-115. http://dx.doi. org/10.1016/j.indcrop.2016.01.051

Serensen, N. A. (1977). Polyacetylenes and conservatism of chemical characters in the Compositae. In V. H. Heywood, J. B. Harborne, & B. L. Turner (Eds.). The biology and chemistry of the Compositae (Vol. 1, pp. 385-409). London: Academic Press.

van den Dool, H. & Kratz, P. D. (1963). A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. Journal of Chromatography A, 11, 463-471.

Vannini, A. B., Santos, T. G., Fleming, A. C., Purnhagen, L. R. P., Lourenco, L. A., Butzke, E. T. B., Kempt, M., ., & Steindel, M. (2012). Chemical characterization and antimicrobial evaluation of the essential oils from Baccharis uncinella D.C. and Baccharis semiserrata D.C. (Asteraceae). Journal of Essential Oil Research, 24(6), 547-554.

Verdi, L. G, Brighente, I. M. C., & Pizzolatti, M. G. (2005). Genero Baccharis (Asteraceae): aspectos quimicos, economicos e biologicos. Quimica Nova, 28(1), 85-94. http://dx.doi.org/10.1590/ S0100-40422005000100017

Zoghbi, M. G. B., Andrade, E. H. A., Santos, A. S., Silva, M. H. L., & Maia, J. G. S. (1998). Essential oils of Lippia alba (Mills.) N. E. Br. growing in the Brazilian Amazon. Flavour and Fragrance Journal, 13(1), 47-48.

Carlos Chaverri & Jose F. Ciccio *

Escuela de Quimica and Centro de Investigaciones en Productos Naturales (CIPRONA), Universidad de Costa Rica, 11501-2060, San Jose, Costa Rica; carloschaverri@yahoo.com, jfciccio@gmail.com

Received 11-V-2017. Corrected 20-VII-2017. Accepted 23-VIII-2017.

Leyenda: Fig. 1. Chemical structures of some principal sesquiterpenic constituents of Baccharis trinervis essential oil from Costa Rica: a) Spathulenol, b) viridiflorol, c) caryophyllene oxide, d) [beta]-caryophyllene, e) germacrene D, and f) germacrene B.
TABLE 1
Chemical and percentage composition of oils of Baccharis trinervis
from three locations in Costa Rica

Compound (a)                                RI     Lit. RI    Class
                                            (b)      (c)       (d)

Hexane                                      623      623        A
3-Methylbutanal                             655      658        A
2-Ethylfuran                                702      702      Misc.
Pentanal                                    704      704        A
4-Methylcyclohexene                         740      740        A
Toluene                                     768    770 (f)      B
Octane                                      800      800        A
Hexanal                                     801      801        A
(E)-Hex-2-enal                              852      846        A
(Z)-Salvene                                 846      847        M
(E)-Hex-2-en-1-ol                           859      854        A
Hexan-1-ol                                  864      863        A
2-Butylfuran                                883    885 (g)    Misc.
Heptan-2-one                                888      889        A
(Z)-Hept-4-enal                             897      898        A
Heptanal                                    901      901        A
[alpha]-Thujene * **                        923      924        M
[alpha]-Knene * **                          930      932        M
Camphene * **                               946      946        M
Thuja-2,4(10)-diene                         952      953        M
Benzaldehyde                                959      952        B
Sabinene * **                               970      969        M
[beta]-Pinene * **                          978      974        M
6-Methylhept-5-en-2-one                     982      981        A
Myrcene * **                                986      988        M
Dehydro-1,8-cineole                         988      988        M
Mesitylene                                  995      995        B
Decane                                     1 000    1 000       A
[delta]-2-Carene                           1 000    1 001       M
[alpha]-Phellandrene *                     1 002    1 002       M
p-Mentha-1(7)-8-diene                      1 003    1 003       M
(Z)-Hex-3-en-1-yl acetate                  1 004    1 004       A
(E)-Hex-2-en-1-yl acetate                  1 007    1 010       A
[delta]-3-Carene *                         1 008    1 008       M
[alpha]-Terpinene *                         1 016    1 014       M
p-Cymene *                                 1 020    1 020       M
o-Cymene                                   1 022    1 022       M
Limonene *                                 1 026    1 024       M
[beta]-Phellandrene * **                   1 027    1 025       M
1,8-Cineole                                1 031    1 026       M
(Z)-P-Ocimene * **                         1 036    1 032       M
(E)-P-Ocimene * **                         1 043    1 034       M
[gamma]-Terpinene * **                     1 056    1 054       M
(E)-Oct-2-en-1-ol                          1 063    1 060       A
cis-Sabinene hydrate **                    1 068    1 065       M
cis-Linalool oxide (furanoid)              1 074    1 067       M
m-Cymenene                                 1 079    1 082       M
p-Mentha-2,4(8)-diene                      1 080    1 085       M
Terpinolene *                              1 084    1 086       M
p-Cymenene                                 1 089    1 089       M
Linalool *                                 1 094    1 095       M
trans-Sabinene hydrate **                  1 099    1 098       M
Undecane                                   1 100    1 100       A
Nonanal                                    1 101    1 100       A
Perillene                                  1 104    1 102      Misc
[alpha]-Fenchocamphorone                   1 109    1 104       M
(Z)-2-Isopropyl-5-methyl-                  1 112    1 112       A
  hex-2-enal
trans-Thujone                              1 113    1 112       M
Dehydro-sabina ketone                      1 116    1 117       M
cis-p-Menth-2-en-1-ol * **                 1 122    1 118       M
[alpha]-Campholenal                        1 123    1 122       M
(E,E)-2,6-Dimethyl-1,3,5,7-                1 128   1 130 (h)    M
  octatetraene
cis-Limonene oxide                         1 131    1 132       M
cis-p-Mentha-2,8-dien-1-ol * **            1 133    1 133       M
trans-Pinocarveol                          1 135    1 135       M
trans-p-Menth-2-en-1-ol                    1 136    1 136       M
trans-Sabinol                              1 136    1 137       M
cis-Pinene hydrate                         1 139    1 139       M
(E)-Tagetone                               1 139    1 139       M
trans-Verbenol                             1 144    1 140       M
p-Meth-3-en-8-ol                           1 148    1 145       M
Eucarvone                                  1 148    1 146       M
neo-iso-Thujan-3-ol                        1 149    1 147       M
Nerol oxide                                1 150    1 154       M
neo-Thujan-3-ol                            1 153    1 149       M
(E)-Non-2-enal                             1 157    1 157       A
Benzyl acetate                             1 158    1 157       B
trans-Pinocamphone                         1 160    1 158       M
[delta]-Terpineol                          1 161    1 162       M
(2Z)-Non-2-en-1-ol                         1 163    1 162       A
1,3-Dimetoxibenzene                        1 165    1 165       B
Borneol                                    1 165    1 165       M
p-Mentha-1,5-dien-8-ol                     1 167    1 166       M
Santolinyl acetate                         1 173    1 171       M
cis-Pinocamphone                           1 175    1 172       M
Terpinen-4-ol * **                         1 177    1 174       M
p-Methyl acetophenone                      1 182    1 179       B
p-Cymen-8-ol                               1 184    1 179       M
Cryptone **                                1 186    1 183       M
Dill ether                                 1 188    1 184       M
[alpha]-Terpineol                          1 190   1 192 (i)    M
Methyl salicylate                          1 191    1 190       B
Dihydrocarveol                             1 192    1 192       M
Myrtenol                                   1 196    1 194       M
cis-Piperitol                              1 198    1 195       M
Safranal                                   1 199    1 197       M
Dodecane                                   1 200    1 200       A
Verbenone                                  1 206    1 204       M
trans-Piperitol                            1 207    1 207       M
(E,E)-Nona-2,4-dienal                      1 209    1 210       A
4-Methylene-isophorone                     1 216    1 216       M
[beta]-Cyclocitral                         1 217    1 217       M
cis-Sabinene-hydrate acetate               1 218    1 219       M
Citronellol                                1 218    1 219       M
(Z)-Ocimenone                              1 228    1 226       M
Nerol                                      1 230    1 227       M
(3Z)-Hexenyl 3-methylbutanoate             1 232    1 230       A
(3Z)-Hexenyl 2-methylbutanoate             1 232    1 232       A
Ascaridole                                 1 234    1 234       M
Cumin aldehyde                             1 240    1 238       M
Carvone                                    1 241    1 239       M
(2Z)-Hexenyl 3-methylbutanoate             1 242    1 241       A
(2E)-Hexenyl 3-methylbutanoate             1 243    1 243       A
Car-3-en-2-one                             1 245    1 244       M
Piperitone                                 1 249    1 249       M
Geraniol                                   1 250    1 249       M
trans-Ascaridol glicol                     1 267    1 266       M
p-Menth-1-en-7-al                          1 285    1 273       M
p-Ethyl acetophenone                       1 285    1 279       B
Bornyl acetate                             1 286    1 287       M
Thymol *                                   1 288    1 289       M
y-Terpinen-7-al                            1 289    1 291       M
Undecan-2-one                              1 295    1 293       A
Tridecane                                  1 300    1 300       A
Undecanal                                  1 308    1 305       A
Dihydrocarveol acetate                     1 309    1 306       M
Isoverbanol acetate                        1 310    1 308       M
(E,E)-Deca-2,4-dienal                      1 314    1 315       A
[delta]-Terpinyl acetate                   1 319    1 316       M
(3Z)-Hexenyl tiglate                       1 320    1 319       A
Silphiperfol-5-ene                         1 323    1 326       S
cis-Piperitol acetate                      1 331    1 332       M
[delta]-Elemene *                          1 334    1 335       S
7-epi-Silphiperfol-5-ene                   1 344    1 345       S
[alpha]-Cubebene                           1 345    1 345       S
[alpha]-Terpinyl acetate *                 1 347    1 346       M
[alpha]-Longipinene                        1 357    1 350       S
Cyclosativene                              1 366    1 369       S
[alpha]-Ylangene                           1 369    1 373       S
[alpha]-Copaene * **                       1 373    1 374       S
Silphiperfol-6-ene                         1 377    1 377       S
[beta]-Patchoulene                         1 379    1 379       S
[beta]-Cubebene                            1 384    1 387       S
[beta]-Bourbonene                          1 386    1 387       S
[beta]-Elemene * **                        1 386    1 389       S
Tetradecane                                1 400    1 400       A
[beta]-Longipinene                         1 401    1 400       S
Methyleugenol                              1 403    1 403       PP
Longifolene                                1 405    1 407       S
[alpha]-Gurjunene                          1 409    1 409       S
[beta]-Caryophyllene * **                  1 416    1 417       S
[beta]-Copaene                             1 428    1 430       S
[beta]-Gurjunene                           1 429    1 431       S
[alpha]-trans-Bergamotene                  1 432    1 432       S
[gamma]-Elemene                            1 432    1 434       S
[alpha]-Guaiene                            1 434    1 437       S
Aromadendrene                              1 437    1 439       S
(Z)-[beta]-Farnesene                       1 438    1 440       S
6,9-Guaiadiene                             1 442    1 442       S
cis-Muurola-3,5-diene                      1 447    1 448       S
trans-Muurola-3,5-diene                    1 450    1 451       S
[alpha]-Humulene * **                      1 453    1 452       S
(E)-[beta]-Farnesene                       1 454    1 454       S
Alloaromadendrene                          1 458    1 458       S
cis-Cadina-1(6),4-diene                    1 460    1 461       S
9-epi-[beta]-Caryophyllene                 1 461    1 464       S
cis-Muurola-4(14),5-diene                  1 465    1 465       S
Dauca-5,8-diene                            1 471    1 471       S
trans-Cadina-1(6),4-diene                  1 471    1 475       S
[gamma]-Gurjunene                          1 477    1 475       S
[gamma]-Muurolene * **                     1 478    1 478       S
ar-Curcumene                               1 471    1 479       S
[gamma]-Curcumene                          1 478    1 481       S
[alpha]-Amorphene                          1 483    1 483       S
Germacrene D *                             1 486    1 484       S
[beta]-Selinene *                          1 490    1 489       S
cis-[beta]-Guaiene                         1 493    1 492       S
trans-Muurola-4(14),5-diene                1 493    1 493       S
Viridiflorene                              1 496    1 496       S
Bicyclogermacrene * **                     1 498    1 500       S
[alpha]-Muurolene *                        1 497    1 500       S
Epizonarene                                1 502    1 501       S
trans-[beta]-Guaiene                       1 506    1 502       S
[beta]-Bisabolene                          1 505    1 505       S
Germacrene A                               1 507    1 508       S
[delta]-Amorphene                          1 510    1 511       S
[gamma]-Cadinene *                         1 513    1 513       S
Cubebol                                    1 515    1 514       S
[beta]-Sesquiphellandrene                  1 518    1 521       S
[delta]-Cadinene *                         1 519    1 522       S
cis-Calamenene                             1 526    1 528       S
Zonarene                                   1 527    1 528       S
(Z)-Nerolidol                              1 533    1 531       S
trans-Cadina-1,4-diene                     1 531    1 533       S
10-epi-Cubebol                             1 535    1 533       S
[alpha]-Cadinene *                         1 536    1 536       S
cis-Sesquisabinene hydrate                 1 537    1 542       S
[alpha]-Calacorene                         1 538    1 544       S
Selina-3,7(11)-diene                       1 541    1 545       S
Hedycaryol                                 1 546    1 546       S
Elemol                                     1 547    1 548       S
trans-Dauca-4(11),7-diene                  1 552    1 557       S
Silphiperfol-5-en-3-ol A                   1 554    1 557       S
Germacrene B *                             1 557    1 559       S
[beta]-Calacorene                          1 560    1 564       S
(E)-Nerolidol                              1 567    1 561       S
Palustrol                                  1 569    1 567       S
Dendrolasin                                1 570    1 570      Misc
(Z)-Dihydroapofarnesol                     1 571    1 571       S
Spathulenol                                1 577    1 577       S
Caryophyllene oxide                        1 583    1 582       S
Thujopsan-2-[alpha]-ol                     1 585    1 586       S
Globulol                                   1 590    1 590       S
Salvial-4(14)-en-1-one                     1 593    1 594       S
Viridiflorol                               1 594    1 592       S
Ledol                                      1 604    1 602       S
5-epi-7-epi-[alpha]-Eudesmol               1 606    1 607       S
Humulene epoxide II                        1 608    1 608       S
1,10-di-epi-Cubenol                        1 616    1 618       S
Junenol                                    1 622    1 618       S
1-epi-Cubenol                              1 626    1 627       S
(E)-Sesquilavandulol                       1 631    1 631       S
cis-Cadin-4-en-7-ol                        1 634    1 635       S
epi-[alpha]-Cadinol (=T-Cadinol) *         1 641    1 638       S
epi-[alpha]-Muurolol (=T-Muurolol)         1 642    1 640       S
Cubenol                                    1 644    1 645       S
[alpha]-Muurolol (=Torreyol) *             1 645    1 644       S
[alpha]-Cadinol *                          1 655    1 652       S
Selin-11-en-4-[alpha]-ol                   1 658    1 658       S
neo-Intermedeol                            1 660    1 658       S
cis-Calamenen-10-ol                        1 663    1 660       S
Intermedeol                                1 665    1 665       S
trans-Calamenen-10-ol                      1 667    1 668       S
14-Hydroxy-9-epi-[beta]-                   1 668    1 668       S
  caryophyllene
Cadalene                                   1 672    1 675       S
Mustakone                                  1 672    1 676       S
Khusinol                                   1 679    1 679       S
epi-[alpha]-Bisabolol                      1 683    1 683       S
Germacra-4(15),5,10(4)-                    1 687    1 685       S
  trien-1-[alpha]-ol
[alpha]-Bisabolol                          1 688    1 685       S
Eudesma-4(15),7-dien-1-[beta]-ol           1 690    1 687       S
Eudesm-7(11)-en-4-ol                       1 697    1 700       S
Heptadecane                                1 700    1 700       A
Amorpha-4,9-dien-2-ol                      1 699    1 700       S
10-Nor-Calamenen-10-one                    1 701    1 702       B
Pentadecanal                               1 724   1 717 (j)    A
Isobicyclogermacrenal                      1 730    1 733       S
Mint sulfide                               1 738    1 740       S
2-[alpha]-Hydroxy-amorpha-                 1 775    1 775       S
  4,7(11)-diene
Hexadecanal                                1 836    1 836       A
6,10,14-Trimethyl-2-pentadecanone          1 848    1 848       IT
Farnesyl acetone                           1 886    1 889       IT
Hexadecanoic acid                          1 959    1 959       A
Ethyl hexadecanoate                        1 992    1 993       A
(Z,E)-Geranyl linalool                     1 998    1 997       D
(6E,10Z)-pseudo Phytol                     2 016    2 018       D
(Z)-Phytol                                 2 014    2 014       D
(E)-Phytol                                 2 106    2 107       D
Linolenic acid                             2 132    2 129       A
Docosane                                   2 200    2 200       A
Tricosane                                  2 300    2 300       A
Pentacosane                                2 500    2 500       A
Hexacosane                                 2 600    2 600       A
Heptacosane                                2 700    2 700       A
Octacosane                                 2 800    2 800       A
Nonacosane                                 2 900    2 900       A
Triacontane                                3 000    3 000       A
Untriacontane                              3 100    3 100       A

Total
Compounds

Compound (a)                                     Miramar

                                            Leaf     Flower

Hexane                                        t
3-Methylbutanal                               t
2-Ethylfuran                                  t
Pentanal
4-Methylcyclohexene
Toluene                                       t
Octane                                        t
Hexanal                                                t
(E)-Hex-2-enal                                t        t
(Z)-Salvene                                   t
(E)-Hex-2-en-1-ol
Hexan-1-ol                                             t
2-Butylfuran                                           t
Heptan-2-one                                           t
(Z)-Hept-4-enal                                        t
Heptanal                                      t       0.1
[alpha]-Thujene * **                         1.0      0.3
[alpha]-Knene * **                           3.9      1.0
Camphene * **                                0.1       t
Thuja-2,4(10)-diene                           t
Benzaldehyde                                  t        t
Sabinene * **                                0.8      0.3
[beta]-Pinene * **                           1.6      1.0
6-Methylhept-5-en-2-one                       t
Myrcene * **                                 0.2      0.3
Dehydro-1,8-cineole                          0.1
Mesitylene
Decane                                                 t
[delta]-2-Carene                              t        t
[alpha]-Phellandrene *
p-Mentha-1(7)-8-diene                         t
(Z)-Hex-3-en-1-yl acetate                     t       0.1
(E)-Hex-2-en-1-yl acetate                              t
[delta]-3-Carene *                           2.0      0.9
[alpha]-Terpinene *                           t       0.1
p-Cymene *                                             t
o-Cymene                                     0.1      0.1
Limonene *                                   0.9      0.6
[beta]-Phellandrene * **                     0.1      0.5
1,8-Cineole                                            t
(Z)-P-Ocimene * **                           0.1       t
(E)-P-Ocimene * **                            t       0.1
[gamma]-Terpinene * **                        t       0.1
(E)-Oct-2-en-1-ol                                      t
cis-Sabinene hydrate **                      0.1      0.2
cis-Linalool oxide (furanoid)
m-Cymenene                                    t        t
p-Mentha-2,4(8)-diene
Terpinolene *                                 t       0.1
p-Cymenene                                    t       0.1
Linalool *                                   0.3      0.1
trans-Sabinene hydrate **                    0.1
Undecane
Nonanal                                       t       0.2
Perillene                                              t
[alpha]-Fenchocamphorone                      t
(Z)-2-Isopropyl-5-methyl-                              t
  hex-2-enal
trans-Thujone                                 t
Dehydro-sabina ketone                        0.1
cis-p-Menth-2-en-1-ol * **                            0.1
[alpha]-Campholenal                          0.1
(E,E)-2,6-Dimethyl-1,3,5,7-
  octatetraene
cis-Limonene oxide                           0.1
cis-p-Mentha-2,8-dien-1-ol * **
trans-Pinocarveol                             t       0.1
trans-p-Menth-2-en-1-ol
trans-Sabinol                                 t
cis-Pinene hydrate
(E)-Tagetone                                 0.3
trans-Verbenol                                         t
p-Meth-3-en-8-ol                             0.2
Eucarvone                                    0.2
neo-iso-Thujan-3-ol
Nerol oxide
neo-Thujan-3-ol                               t
(E)-Non-2-enal                                         t
Benzyl acetate                               0.1
trans-Pinocamphone
[delta]-Terpineol                                     0.2
(2Z)-Non-2-en-1-ol
1,3-Dimetoxibenzene                                   0.1
Borneol                                      0.1
p-Mentha-1,5-dien-8-ol                                 t
Santolinyl acetate
cis-Pinocamphone                             0.1      0.1
Terpinen-4-ol * **                           0.7      0.1
p-Methyl acetophenone                         t
p-Cymen-8-ol                                 0.4
Cryptone **                                           0.1
Dill ether
[alpha]-Terpineol                            0.5
Methyl salicylate
Dihydrocarveol                                t
Myrtenol                                              0.1
cis-Piperitol
Safranal                                      t
Dodecane
Verbenone                                    0.3      0.1
trans-Piperitol
(E,E)-Nona-2,4-dienal                         t
4-Methylene-isophorone                        t
[beta]-Cyclocitral                                    0.1
cis-Sabinene-hydrate acetate
Citronellol
(Z)-Ocimenone                                          t
Nerol
(3Z)-Hexenyl 3-methylbutanoate
(3Z)-Hexenyl 2-methylbutanoate
Ascaridole
Cumin aldehyde                                        0.1
Carvone                                      0.2
(2Z)-Hexenyl 3-methylbutanoate
(2E)-Hexenyl 3-methylbutanoate
Car-3-en-2-one                               0.1      0.1
Piperitone                                   0.1       t
Geraniol                                               t
trans-Ascaridol glicol
p-Menth-1-en-7-al                                      t
p-Ethyl acetophenone
Bornyl acetate                               0.1       t
Thymol *                                     0.3
y-Terpinen-7-al
Undecan-2-one                                          t
Tridecane                                             0.1
Undecanal                                             0.1
Dihydrocarveol acetate
Isoverbanol acetate
(E,E)-Deca-2,4-dienal                                  t
[delta]-Terpinyl acetate                      t
(3Z)-Hexenyl tiglate
Silphiperfol-5-ene                                    0.1
cis-Piperitol acetate                                 0.2
[delta]-Elemene *                                     0.2
7-epi-Silphiperfol-5-ene
[alpha]-Cubebene                             0.4      0.3
[alpha]-Terpinyl acetate *
[alpha]-Longipinene                           t
Cyclosativene                                0.5       t
[alpha]-Ylangene                                      0.4
[alpha]-Copaene * **                         1.3      0.7
Silphiperfol-6-ene                                    0.2
[beta]-Patchoulene                            t
[beta]-Cubebene                                       0.1
[beta]-Bourbonene                             t
[beta]-Elemene * **                          0.8      2.5
Tetradecane                                            t
[beta]-Longipinene                                    0.1
Methyleugenol                                0.2
Longifolene
[alpha]-Gurjunene
[beta]-Caryophyllene * **                    3.5      9.5
[beta]-Copaene                               0.3      0.8
[beta]-Gurjunene
[alpha]-trans-Bergamotene                     t       0.1
[gamma]-Elemene
[alpha]-Guaiene
Aromadendrene                                 t       0.1
(Z)-[beta]-Farnesene                         0.1      0.3
6,9-Guaiadiene
cis-Muurola-3,5-diene                                  t
trans-Muurola-3,5-diene
[alpha]-Humulene * **                        0.5      2.2
(E)-[beta]-Farnesene                                   t
Alloaromadendrene                            0.1
cis-Cadina-1(6),4-diene
9-epi-[beta]-Caryophyllene
cis-Muurola-4(14),5-diene                             13.7
Dauca-5,8-diene                               t
trans-Cadina-1(6),4-diene                     t
[gamma]-Gurjunene
[gamma]-Muurolene * **
ar-Curcumene                                 2.0      8.0
[gamma]-Curcumene                            1.5
[alpha]-Amorphene                            0.2
Germacrene D *                               0.5      4.3
[beta]-Selinene *                                     0.3
cis-[beta]-Guaiene                           0.6
trans-Muurola-4(14),5-diene                            t
Viridiflorene
Bicyclogermacrene * **                                8.3
[alpha]-Muurolene *                          0.5
Epizonarene
trans-[beta]-Guaiene                                  0.5
[beta]-Bisabolene                            0.4      1.4
Germacrene A
[delta]-Amorphene                            0.1      0.4
[gamma]-Cadinene *                           0.3      2.5
Cubebol                                      2.5      0.3
[beta]-Sesquiphellandrene                             0.5
[delta]-Cadinene *                           0.8
cis-Calamenene                               0.3
Zonarene
(Z)-Nerolidol                                0.1
trans-Cadina-1,4-diene                       0.2      0.5
10-epi-Cubebol                               0.1
[alpha]-Cadinene *                                    0.2
cis-Sesquisabinene hydrate
[alpha]-Calacorene                           0.7      0.5
Selina-3,7(11)-diene
Hedycaryol
Elemol
trans-Dauca-4(11),7-diene
Silphiperfol-5-en-3-ol A                     0.1
Germacrene B *                               0.2      4.3
[beta]-Calacorene                            1.3
(E)-Nerolidol                                0.2
Palustrol                                    0.3      0.1
Dendrolasin                                           0.1
(Z)-Dihydroapofarnesol                                 t
Spathulenol                                  8.3      4.3
Caryophyllene oxide                         22.5      3.1
Thujopsan-2-[alpha]-ol
Globulol
Salvial-4(14)-en-1-one                                 t
Viridiflorol                                20.3      4.7
Ledol                                        0.5
5-epi-7-epi-[alpha]-Eudesmol
Humulene epoxide II                          2.5      1.2
1,10-di-epi-Cubenol
Junenol
1-epi-Cubenol                                2.1      0.7
(E)-Sesquilavandulol                         0.3
cis-Cadin-4-en-7-ol                          1.6      3.5
epi-[alpha]-Cadinol (=T-Cadinol) *           0.3      1.1
epi-[alpha]-Muurolol (=T-Muurolol)                    1.0
Cubenol                                               0.5
[alpha]-Muurolol (=Torreyol) *               0.5
[alpha]-Cadinol *                                      1.2
Selin-11-en-4-[alpha]-ol                                t
neo-Intermedeol
cis-Calamenen-10-ol
Intermedeol
trans-Calamenen-10-ol
14-Hydroxy-9-epi-[beta]-                     1.3
  caryophyllene
Cadalene                                      t       0.4
Mustakone                                    0.5
Khusinol
epi-[alpha]-Bisabolol                                  0.5
Germacra-4(15),5,10(4)-
  trien-1-[alpha]-ol
[alpha]-Bisabolol                                      0.5
Eudesma-4(15),7-dien-1-[beta]-ol             0.6
Eudesm-7(11)-en-4-ol
Heptadecane
Amorpha-4,9-dien-2-ol                         t
10-Nor-Calamenen-10-one                       t
Pentadecanal                                          0.3
Isobicyclogermacrenal                         t
Mint sulfide                                          0.5
2-[alpha]-Hydroxy-amorpha-                    t
  4,7(11)-diene
Hexadecanal
6,10,14-Trimethyl-2-pentadecanone                     0.3
Farnesyl acetone
Hexadecanoic acid
Ethyl hexadecanoate
(Z,E)-Geranyl linalool
(6E,10Z)-pseudo Phytol                                0.2
(Z)-Phytol                                            0.1
(E)-Phytol
Linolenic acid
Docosane                                               t
Tricosane                                              t
Pentacosane                                            t
Hexacosane                                             t
Heptacosane                                            t
Octacosane                                             t
Nonacosane                                             t
Triacontane                                            t
Untriacontane                                          t

Total                                       97.3      95.6
Compounds                                    121      129

Compound (2)                                      San Pedro     Pavas

                                             Leaf      Branch   Leaf

Hexane
3-Methylbutanal
2-Ethylfuran
Pentanal                                       t        0.1
4-Methylcyclohexene                            t
Toluene
Octane
Hexanal                                                  t
(E)-Hex-2-enal                                 t         t       0.1
(Z)-Salvene
(E)-Hex-2-en-1-ol                             0.1                0.2
Hexan-1-ol                                    0.1                 t
2-Butylfuran
Heptan-2-one
(Z)-Hept-4-enal
Heptanal                                       t         t        t
[alpha]-Thujene * **                          1.7       0.3      1.6
[alpha]-Knene * **                            2.5       0.6      5.9
Camphene * **                                 0.1                0.1
Thuja-2,4(10)-diene
Benzaldehyde                                   t
Sabinene * **                                 0.4       0.2      1.6
[beta]-Pinene * **                            1.3       0.8      2.5
6-Methylhept-5-en-2-one                                           t
Myrcene * **                                  0.8       0.5      1.3
Dehydro-1,8-cineole
Mesitylene                                                        t
Decane
[delta]-2-Carene                               t                  t
[alpha]-Phellandrene *                                           0.1
p-Mentha-1(7)-8-diene
(Z)-Hex-3-en-1-yl acetate
(E)-Hex-2-en-1-yl acetate
[delta]-3-Carene *                            6.8       4.1      6.6
[alpha]-Terpinene *                           0.2       0.1      0.1
p-Cymene *                                    0.1                 t
o-Cymene                                                         0.8
Limonene *                                    0.9       0.7      2.9
[beta]-Phellandrene * **                      1.9       1.5      1.0
1,8-Cineole
(Z)-P-Ocimene * **                             t                  t
(E)-P-Ocimene * **                            0.5       0.3      0.1
[gamma]-Terpinene * **                        0.9       0.3       t
(E)-Oct-2-en-1-ol
cis-Sabinene hydrate **                                           t
cis-Linalool oxide (furanoid)
m-Cymenene
p-Mentha-2,4(8)-diene                          t                 0.1
Terpinolene *                                 1.0       0.6       t
p-Cymenene                                     t        0.1
Linalool *                                     t         t       0.1
trans-Sabinene hydrate **                      t                 0.1
Undecane
Nonanal                                                  t        t
Perillene                                               0.1       t
[alpha]-Fenchocamphorone
(Z)-2-Isopropyl-5-methyl-
  hex-2-enal
trans-Thujone
Dehydro-sabina ketone
cis-p-Menth-2-en-1-ol * **                    0.1        t       0.2
[alpha]-Campholenal
(E,E)-2,6-Dimethyl-1,3,5,7-                    t
  octatetraene
cis-Limonene oxide                                                t
cis-p-Mentha-2,8-dien-1-ol * **                          t
trans-Pinocarveol
trans-p-Menth-2-en-1-ol                        t                 0.1
trans-Sabinol
cis-Pinene hydrate
(E)-Tagetone
trans-Verbenol
p-Meth-3-en-8-ol
Eucarvone
neo-iso-Thujan-3-ol                                      t
Nerol oxide                                    t                  t
neo-Thujan-3-ol
(E)-Non-2-enal                                           t
Benzyl acetate
trans-Pinocamphone
[delta]-Terpineol
(2Z)-Non-2-en-1-ol
1,3-Dimetoxibenzene
Borneol                                        t
p-Mentha-1,5-dien-8-ol                                   t        t
Santolinyl acetate
cis-Pinocamphone
Terpinen-4-ol * **                            0.5       0.3      0.7
p-Methyl acetophenone
p-Cymen-8-ol                                   t                 0.7
Cryptone **                                    t         t       0.1
Dill ether
[alpha]-Terpineol                                        t       0.1
Methyl salicylate                              t         t
Dihydrocarveol
Myrtenol
cis-Piperitol                                  t
Safranal
Dodecane
Verbenone
trans-Piperitol                                t                  t
(E,E)-Nona-2,4-dienal
4-Methylene-isophorone                                           0.1
[beta]-Cyclocitral
cis-Sabinene-hydrate acetate                   t
Citronellol                                    t
(Z)-Ocimenone
Nerol                                          t
(3Z)-Hexenyl 3-methylbutanoate
(3Z)-Hexenyl 2-methylbutanoate                 t
Ascaridole                                                        t
Cumin aldehyde
Carvone
(2Z)-Hexenyl 3-methylbutanoate                                    t
(2E)-Hexenyl 3-methylbutanoate                                   0.1
Car-3-en-2-one                                 t                 0.1
Piperitone
Geraniol                                                 t
trans-Ascaridol glicol                                           0.1
p-Menth-1-en-7-al
p-Ethyl acetophenone                                     t
Bornyl acetate
Thymol *
y-Terpinen-7-al                                          t
Undecan-2-one
Tridecane
Undecanal
Dihydrocarveol acetate
Isoverbanol acetate                                              0.5
(E,E)-Deca-2,4-dienal                                   0.1
[delta]-Terpinyl acetate
(3Z)-Hexenyl tiglate                                              t
Silphiperfol-5-ene
cis-Piperitol acetate                                    t
[delta]-Elemene *                             0.3       0.2      0.1
7-epi-Silphiperfol-5-ene                       t         t
[alpha]-Cubebene                              0.5       0.7      0.2
[alpha]-Terpinyl acetate *                                        0.2
[alpha]-Longipinene
Cyclosativene                                            t
[alpha]-Ylangene                              0.3       0.5      0.4
[alpha]-Copaene * **                          1.1       1.5      0.6
Silphiperfol-6-ene
[beta]-Patchoulene
[beta]-Cubebene                                t                  t
[beta]-Bourbonene                                                0.2
[beta]-Elemene * **                           2.1       2.7      3.0
Tetradecane
[beta]-Longipinene                             t        0.1
Methyleugenol                                  t
Longifolene                                    t         t
[alpha]-Gurjunene                                        t       0.2
[beta]-Caryophyllene * **                     9.1       12.4     7.9
[beta]-Copaene                                 t        2.8      0.7
[beta]-Gurjunene
[alpha]-trans-Bergamotene
[gamma]-Elemene                               1.9                 t
[alpha]-Guaiene                               0.1                0.1
Aromadendrene                                 0.2       0.1      0.3
(Z)-[beta]-Farnesene
6,9-Guaiadiene                                0.1        t        t
cis-Muurola-3,5-diene                                    t       0.2
trans-Muurola-3,5-diene                       0.2        t        t
[alpha]-Humulene * **                         1.0       1.3      1.1
(E)-[beta]-Farnesene
Alloaromadendrene                             0.1
cis-Cadina-1(6),4-diene                        t
9-epi-[beta]-Caryophyllene                                       0.1
cis-Muurola-4(14),5-diene                                t       0.1
Dauca-5,8-diene
trans-Cadina-1(6),4-diene
[gamma]-Gurjunene                                                 t
[gamma]-Muurolene * **                                  2.1      1.6
ar-Curcumene
[gamma]-Curcumene
[alpha]-Amorphene                                        0.1
Germacrene D *                               19.1       14.7     6.3
[beta]-Selinene *                             0.9       1.6      1.1
cis-[beta]-Guaiene
trans-Muurola-4(14),5-diene                   0.7                 t
Viridiflorene                                           0.7
Bicyclogermacrene * **                        4.4       3.6      2.5
[alpha]-Muurolene *                                      1.0       t
Epizonarene                                   0.7
trans-[beta]-Guaiene
[beta]-Bisabolene
Germacrene A                                  0.5       0.4      0.3
[delta]-Amorphene                                       0.4
[gamma]-Cadinene *                            0.6       0.8      0.5
Cubebol                                       0.1        t
[beta]-Sesquiphellandrene
[delta]-Cadinene *                            3.4       4.3      1.4
cis-Calamenene                                          0.2       t
Zonarene                                      0.1
(Z)-Nerolidol
trans-Cadina-1,4-diene                        0.2       0.2      0.2
10-epi-Cubebol
[alpha]-Cadinene *                            0.4       0.6      0.2
cis-Sesquisabinene hydrate                                        t
[alpha]-Calacorene                                                 t
Selina-3,7(11)-diene                          0.3       0.6
Hedycaryol                                                       0.3
Elemol
trans-Dauca-4(11),7-diene                                t
Silphiperfol-5-en-3-ol A
Germacrene B *                               16.0       18.7     1.4
[beta]-Calacorene
(E)-Nerolidol                                           0.1
Palustrol                                     0.1       0.2      0.4
Dendrolasin                                             0.1
(Z)-Dihydroapofarnesol
Spathulenol                                   0.1       0.2      3.0
Caryophyllene oxide                           0.1       1.3      1.7
Thujopsan-2-[alpha]-ol                                    t
Globulol                                      0.1       11.3     0.3
Salvial-4(14)-en-1-one
Viridiflorol                                  8.8               21.0
Ledol                                         0.1       0.1      0.5
5-epi-7-epi-[alpha]-Eudesmol                             t       0.6
Humulene epoxide II
1,10-di-epi-Cubenol                            t
Junenol                                                  t
1-epi-Cubenol                                 0.1       0.2      0.4
(E)-Sesquilavandulol
cis-Cadin-4-en-7-ol
epi-[alpha]-Cadinol (=T-Cadinol) *            0.3       0.4      1.3
epi-[alpha]-Muurolol (=T-Muurolol)            0.1       0.1      0.9
Cubenol
[alpha]-Muurolol (=Torreyol) *                 t         t
[alpha]-Cadinol *                             0.8       0.5      1.7
Selin-11-en-4-[alpha]-ol                      0.1                0.5
neo-Intermedeol                                         0.3
cis-Calamenen-10-ol                                              0.3
Intermedeol                                              t
trans-Calamenen-10-ol                                            0.3
14-Hydroxy-9-epi-[beta]-                       t
  caryophyllene
Cadalene
Mustakone
Khusinol                                                 t
epi-[alpha]-Bisabolol
Germacra-4(15),5,10(4)-                                          0.4
  trien-1-[alpha]-ol
[alpha]-Bisabolol
Eudesma-4(15),7-dien-1-[beta]-ol
Eudesm-7(11)-en-4-ol                           t        0.1
Heptadecane
Amorpha-4,9-dien-2-ol
10-Nor-Calamenen-10-one
Pentadecanal                                            0.1
Isobicyclogermacrenal
Mint sulfide                                                     0.6
2-[alpha]-Hydroxy-amorpha-                              0.3
  4,7(11)-diene
Hexadecanal
6,10,14-Trimethyl-2-pentadecanone
Farnesyl acetone                                         t
Hexadecanoic acid                                       0.3
Ethyl hexadecanoate
(Z,E)-Geranyl linalool
(6E,10Z)-pseudo Phytol
(Z)-Phytol
(E)-Phytol                                                        t
Linolenic acid
Docosane
Tricosane
Pentacosane
Hexacosane
Heptacosane
Octacosane
Nonacosane
Triacontane
Untriacontane

Total                                        96.0       98.6    93.1
Compounds                                     92         93      102

Compound (2)                                     Pavas

                                           Flower   Branch

Hexane
3-Methylbutanal
2-Ethylfuran
Pentanal
4-Methylcyclohexene
Toluene
Octane
Hexanal
(E)-Hex-2-enal                                       0.1
(Z)-Salvene
(E)-Hex-2-en-1-ol                                    0.1
Hexan-1-ol                                            t
2-Butylfuran
Heptan-2-one
(Z)-Hept-4-enal
Heptanal                                              t
[alpha]-Thujene * **                        0.1      0.3
[alpha]-Knene * **                          0.3      1.9
Camphene * **                                         t
Thuja-2,4(10)-diene
Benzaldehyde
Sabinene * **                               0.3      0.3
[beta]-Pinene * **                          0.4      2.1
6-Methylhept-5-en-2-one
Myrcene * **                                0.1      1.4
Dehydro-1,8-cineole
Mesitylene
Decane                                       t
[delta]-2-Carene                             t
[alpha]-Phellandrene *
p-Mentha-1(7)-8-diene
(Z)-Hex-3-en-1-yl acetate
(E)-Hex-2-en-1-yl acetate
[delta]-3-Carene *                          2.2      8.1
[alpha]-Terpinene *                          t       0.4
p-Cymene *                                   t
o-Cymene                                    0.2      0.4
Limonene *                                  0.6      1.5
[beta]-Phellandrene * **                    0.3      6.5
1,8-Cineole
(Z)-P-Ocimene * **                           t        t
(E)-P-Ocimene * **                           t       1.0
[gamma]-Terpinene * **                      0.1      1.1
(E)-Oct-2-en-1-ol
cis-Sabinene hydrate **
cis-Linalool oxide (furanoid)               0.2
m-Cymenene
p-Mentha-2,4(8)-diene
Terpinolene *                               0.2      1.5
p-Cymenene                                           0.2
Linalool *                                  0.1
trans-Sabinene hydrate **
Undecane                                              t
Nonanal                                      t        t
Perillene                                    t       1.0
[alpha]-Fenchocamphorone
(Z)-2-Isopropyl-5-methyl-
  hex-2-enal
trans-Thujone
Dehydro-sabina ketone
cis-p-Menth-2-en-1-ol * **                   t       0.1
[alpha]-Campholenal
(E,E)-2,6-Dimethyl-1,3,5,7-                           t
  octatetraene
cis-Limonene oxide                          0.1
cis-p-Mentha-2,8-dien-1-ol * **
trans-Pinocarveol
trans-p-Menth-2-en-1-ol                               t
trans-Sabinol
cis-Pinene hydrate                           t
(E)-Tagetone
trans-Verbenol                              0.1
p-Meth-3-en-8-ol
Eucarvone
neo-iso-Thujan-3-ol
Nerol oxide
neo-Thujan-3-ol
(E)-Non-2-enal
Benzyl acetate
trans-Pinocamphone                          0.1
[delta]-Terpineol
(2Z)-Non-2-en-1-ol                          0.1
1,3-Dimetoxibenzene
Borneol
p-Mentha-1,5-dien-8-ol                       t
Santolinyl acetate                                    t
cis-Pinocamphone
Terpinen-4-ol * **                          0.1      0.8
p-Methyl acetophenone
p-Cymen-8-ol                                0.1
Cryptone **
Dill ether                                  0.2
[alpha]-Terpineol                           0.1      0.2
Methyl salicylate                                     t
Dihydrocarveol
Myrtenol
cis-Piperitol                                         t
Safranal
Dodecane                                    0.1
Verbenone
trans-Piperitol
(E,E)-Nona-2,4-dienal
4-Methylene-isophorone
[beta]-Cyclocitral
cis-Sabinene-hydrate acetate                          t
Citronellol
(Z)-Ocimenone
Nerol
(3Z)-Hexenyl 3-methylbutanoate                        t
(3Z)-Hexenyl 2-methylbutanoate
Ascaridole
Cumin aldehyde
Carvone
(2Z)-Hexenyl 3-methylbutanoate
(2E)-Hexenyl 3-methylbutanoate                        t
Car-3-en-2-one
Piperitone
Geraniol
trans-Ascaridol glicol
p-Menth-1-en-7-al                                     t
p-Ethyl acetophenone
Bornyl acetate
Thymol *
[gamma]-Terpinen-7-al
Undecan-2-one
Tridecane                                    t
Undecanal                                   0.2
Dihydrocarveol acetate                       t
Isoverbanol acetate
(E,E)-Deca-2,4-dienal
[delta]-Terpinyl acetate
(3Z)-Hexenyl tiglate
Silphiperfol-5-ene
cis-Piperitol acetate
[delta]-Elemene *                           0.2      0.1
7-epi-Silphiperfol-5-ene                    0.1
[alpha]-Cubebene                                      0.2
[alpha]-Terpinyl acetate *
[alpha]-Longipinene                         0.1
Cyclosativene
[alpha]-Ylangene                            0.3      0.3
[alpha]-Copaene * **                        0.8      1.0
Silphiperfol-6-ene
[beta]-Patchoulene
[beta]-Cubebene                             0.3      0.1
[beta]-Bourbonene                                    0.1
[beta]-Elemene * **                         4.3      1.3
Tetradecane                                  t
[beta]-Longipinene
Methyleugenol
Longifolene
[alpha]-Gurjunene                           0.1
[beta]-Caryophyllene * **                   17.1     10.1
[beta]-Copaene                               t       0.6
[beta]-Gurjunene                            0.7
[alpha]-trans-Bergamotene                             0.1
[gamma]-Elemene
[alpha]-Guaiene                             0.1
Aromadendrene                               0.1      0.2
(Z)-[beta]-Farnesene
6,9-Guaiadiene                               t
cis-Muurola-3,5-diene                        t       0.1
trans-Muurola-3,5-diene                              0.1
[alpha]-Humulene * **                       1.8      1.4
(E)-[beta]-Farnesene
Alloaromadendrene                           0.1      0.1
cis-Cadina-1(6),4-diene                              0.1
9-epi-[beta]-Caryophyllene                   t        t
cis-Muurola-4(14),5-diene                    t
Dauca-5,8-diene
trans-Cadina-1(6),4-diene
[gamma]-Gurjunene                           0.6      0.3
[gamma]-Muurolene * **                               1.6
ar-Curcumene
[gamma]-Curcumene
[alpha]-Amorphene
Germacrene D *                              9.9      15.6
[beta]-Selinene *                           0.5
cis-[beta]-Guaiene
trans-Muurola-4(14),5-diene
Viridiflorene                                        1.8
Bicyclogermacrene * **                      5.9      4.9
[alpha]-Muurolene *                                   0.4
Epizonarene
trans-[beta]-Guaiene
[beta]-Bisabolene
Germacrene A
[delta]-Amorphene                           0.5      0.3
[gamma]-Cadinene *                          0.3      0.5
Cubebol                                      t
[beta]-Sesquiphellandrene
[delta]-Cadinene *                          1.4      3.5
cis-Calamenene
Zonarene                                             0.1
(Z)-Nerolidol
trans-Cadina-1,4-diene
10-epi-Cubebol                                       0.3
[alpha]-Cadinene *                          0.1
cis-Sesquisabinene hydrate
[alpha]-Calacorene                          0.1      0.2
Selina-3,7(11)-diene
Hedycaryol
Elemol                                      0.2
trans-Dauca-4(11),7-diene
Silphiperfol-5-en-3-ol A
Germacrene B *                              1.8      1.4
[beta]-Calacorene                           0.2      0.4
(E)-Nerolidol
Palustrol                                   0.4      0.4
Dendrolasin
(Z)-Dihydroapofarnesol                               0.1
Spathulenol                                 4.8      0.3
Caryophyllene oxide                         4.7      0.4
Thujopsan-2-[alpha]-ol
Globulol                                    24.8     0.6
Salvial-4(14)-en-1-one
Viridiflorol                                0.3      11.5
Ledol                                                0.3
5-epi-7-epi-[alpha]-Eudesmol                         0.5
Humulene epoxide II
1,10-di-epi-Cubenol                                  0.3
Junenol                                              0.4
1-epi-Cubenol                                        0.6
(E)-Sesquilavandulol
cis-Cadin-4-en-7-ol                                  0.5
epi-[alpha]-Cadinol (=T-Cadinol) *          0.7       t
epi-[alpha]-Muurolol (=T-Muurolol)          0.8      1.3
Cubenol
[alpha]-Muurolol (=Torreyol) *                       0.4
[alpha]-Cadinol *                           0.3      1.7
Selin-11-en-4-[alpha]-ol                    1.1      0.4
neo-Intermedeol
cis-Calamenen-10-ol
Intermedeol                                          0.1
trans-Calamenen-10-ol                       0.2
14-Hydroxy-9-epi-[beta]-
  caryophyllene
Cadalene
Mustakone
Khusinol
epi-[alpha]-Bisabolol
Germacra-4(15),5,10(4)-                     0.4
  trien-1-[alpha]-ol
[alpha]-Bisabolol

Eudesma-4(15),7-dien-1-[beta]-ol            0.1
Eudesm-7(11)-en-4-ol
Heptadecane                                 0.2
Amorpha-4,9-dien-2-ol
10-Nor-Calamenen-10-one
Pentadecanal                                0.3
Isobicyclogermacrenal
Mint sulfide                                0.4      0.1
2-[alpha]-Hydroxy-amorpha-
  4,7(11)-diene
Hexadecanal                                          0.1
6,10,14-Trimethyl-2-pentadecanone
Farnesyl acetone
Hexadecanoic acid
Ethyl hexadecanoate                                  0.1
(Z,E)-Geranyl linalool                               0.2
(6E,10Z)-pseudo Phytol
(Z)-Phytol                                           0.2
(E)-Phytol
Linolenic acid                                       0.1
Docosane
Tricosane
Pentacosane
Hexacosane
Heptacosane
Octacosane
Nonacosane
Triacontane
Untriacontane

Total                                       93.4     96.8
Compounds                                    84       90

Compound (2)                                 Ident.

                                           method (e)

Hexane                                       1,2,3
3-Methylbutanal                               1,2
2-Ethylfuran                                  1,2
Pentanal                                      1,2
4-Methylcyclohexene                           1,2
Toluene                                       1,2
Octane                                       1,2,3
Hexanal                                       1,2
(E)-Hex-2-enal                                1,2
(Z)-Salvene                                   1,2
(E)-Hex-2-en-1-ol                             1,2
Hexan-1-ol                                    1,2
2-Butylfuran                                  1,2
Heptan-2-one                                  1,2
(Z)-Hept-4-enal                               1,2
Heptanal                                      1,2
[alpha]-Thujene * **                          1,2
[alpha]-Knene * **                           1,2,3
Camphene * **                                 1,2
Thuja-2,4(10)-diene                           1,2
Benzaldehyde                                  1,2
Sabinene * **                                 1,2
[beta]-Pinene * **                           1,2,3
6-Methylhept-5-en-2-one                       1,2
Myrcene * **                                  1,2
Dehydro-1,8-cineole                           1,2
Mesitylene                                    1,2
Decane                                       1,2,3
[delta]-2-Carene                              1,2
[alpha]-Phellandrene *                        1,2
p-Mentha-1(7)-8-diene                         1,2
(Z)-Hex-3-en-1-yl acetate                     1,2
(E)-Hex-2-en-1-yl acetate                     1,2
[delta]-3-Carene *                            1,2
[alpha]-Terpinene *                           1,2
p-Cymene *                                    1,2
o-Cymene                                      1,2
Limonene *                                   1,2,3
[beta]-Phellandrene * **                      1,2
1,8-Cineole                                  1,2,3
(Z)-P-Ocimene * **                            1,2
(E)-P-Ocimene * **                            1,2
[gamma]-Terpinene * **                        1,2
(E)-Oct-2-en-1-ol                             1,2
cis-Sabinene hydrate **                       1,2
cis-Linalool oxide (furanoid)                 1,2
m-Cymenene                                    1,2
p-Mentha-2,4(8)-diene                         1,2
Terpinolene *                                 1,2
p-Cymenene                                    1,2
Linalool *                                   1,2,3
trans-Sabinene hydrate **                     1,2
Undecane                                      1,2
Nonanal                                       1,2
Perillene                                     1,2
[alpha]-Fenchocamphorone                      1,2
(Z)-2-Isopropyl-5-methyl-                     1,2
  hex-2-enal
trans-Thujone                                 1,2
Dehydro-sabina ketone                         1,2
cis-p-Menth-2-en-1-ol * **                    1,2
[alpha]-Campholenal                           1,2
(E,E)-2,6-Dimethyl-1,3,5,7-                   1,2
  octatetraene
cis-Limonene oxide                            1,2
cis-p-Mentha-2,8-dien-1-ol * **               1,2
trans-Pinocarveol                             1,2
trans-p-Menth-2-en-1-ol                       1,2
trans-Sabinol                                 1,2
cis-Pinene hydrate                            1,2
(E)-Tagetone                                  1,2
trans-Verbenol                                1,2
p-Meth-3-en-8-ol                              1,2
Eucarvone                                     1,2
neo-iso-Thujan-3-ol                           1,2
Nerol oxide                                   1,2
neo-Thujan-3-ol                               1,2
(E)-Non-2-enal                                1,2
Benzyl acetate                                1,2
trans-Pinocamphone                            1,2
[delta]-Terpineol                             1,2
(2Z)-Non-2-en-1-ol                            1,2
1,3-Dimetoxibenzene                           1,2
Borneol                                       1,2
p-Mentha-1,5-dien-8-ol                        1,2
Santolinyl acetate                            1.2
cis-Pinocamphone                              1,2
Terpinen-4-ol * **                           1,2,3
p-Methyl acetophenone                         1,2
p-Cymen-8-ol                                  1,2
Cryptone **                                   1,2
Dill ether                                    1,2
[alpha]-Terpineol                             1,2
Methyl salicylate                             1,2
Dihydrocarveol                                1,2
Myrtenol                                      1,2
cis-Piperitol                                 1,2
Safranal                                      1,2
Dodecane                                     1,2,3
Verbenone                                     1,2
trans-Piperitol                               1,2
(E,E)-Nona-2,4-dienal                         1,2
4-Methylene-isophorone                        1,2
[beta]-Cyclocitral                            1,2
cis-Sabinene-hydrate acetate                  1,2
Citronellol                                   1,2
(Z)-Ocimenone                                 1,2
Nerol                                         1,2
(3Z)-Hexenyl 3-methylbutanoate                1,2
(3Z)-Hexenyl 2-methylbutanoate                1,2
Ascaridole                                    1,2
Cumin aldehyde                                1,2
Carvone                                       1,2
(2Z)-Hexenyl 3-methylbutanoate                1,2
(2E)-Hexenyl 3-methylbutanoate                1,2
Car-3-en-2-one                                1,2
Piperitone                                    1,2
Geraniol                                      1,2
trans-Ascaridol glicol                        1,2
p-Menth-1-en-7-al                             1,2
p-Ethyl acetophenone                          1,2
Bornyl acetate                                1,2
Thymol *                                      1,2
[gamma]-Terpinen-7-al                         1,2
Undecan-2-one                                 1,2
Tridecane                                    1,2,3
Undecanal                                     1,2
Dihydrocarveol acetate                        1,2
Isoverbanol acetate                           1,2
(E,E)-Deca-2,4-dienal                         1,2
[delta]-Terpinyl acetate                      1,2
(3Z)-Hexenyl tiglate                          1,2
Silphiperfol-5-ene                            1,2
cis-Piperitol acetate                         1,2
[delta]-Elemene *                             1,2
7-epi-Silphiperfol-5-ene                      1,2
[alpha]-Cubebene                              1,2
[alpha]-Terpinyl acetate *                    1,2
[alpha]-Longipinene                           1,2
Cyclosativene                                 1,2
[alpha]-Ylangene                              1,2
[alpha]-Copaene * **                          1,2
Silphiperfol-6-ene                            1,2
[beta]-Patchoulene                            1,2
[beta]-Cubebene                               1,2
[beta]-Bourbonene                             1,2
[beta]-Elemene * **                           1,2
Tetradecane                                  1,2,3
[beta]-Longipinene                            1,2
Methyleugenol                                 1,2
Longifolene                                   1,2
[alpha]-Gurjunene                             1,2
[beta]-Caryophyllene * **                    1,2,3
[beta]-Copaene                                1,2
[beta]-Gurjunene                              1,2
[alpha]-trans-Bergamotene                     1,2
[gamma]-Elemene                               1,2
[alpha]-Guaiene                               1,2
Aromadendrene                                 1,2
(Z)-[beta]-Farnesene                          1,2
6,9-Guaiadiene                                1,2
cis-Muurola-3,5-diene                         1,2
trans-Muurola-3,5-diene                       1,2
[alpha]-Humulene * **                        1,2,3
(E)-[beta]-Farnesene                          1,2
Alloaromadendrene                             1,2
cis-Cadina-1(6),4-diene                       1,2
9-epi-[beta]-Caryophyllene                    1,2
cis-Muurola-4(14),5-diene                     1,2
Dauca-5,8-diene                               1,2
trans-Cadina-1(6),4-diene                     1,2
[gamma]-Gurjunene                             1,2
[gamma]-Muurolene * **                        1,2
ar-Curcumene                                  1,2
[gamma]-Curcumene                             1,2
[alpha]-Amorphene                             1,2
Germacrene D *                               1,2,3
[beta]-Selinene *                             1,2
cis-[beta]-Guaiene                            1,2
trans-Muurola-4(14),5-diene                   1,2
Viridiflorene                                 1,2
Bicyclogermacrene * **                        1,2
[alpha]-Muurolene *                           1,2
Epizonarene                                   1,2
trans-[beta]-Guaiene                          1,2
[beta]-Bisabolene                             1,2
Germacrene A                                  1,2
[delta]-Amorphene                             1,2
[gamma]-Cadinene *                            1,2
Cubebol                                       1,2
[beta]-Sesquiphellandrene                     1,2
[delta]-Cadinene *                            1,2
cis-Calamenene                                1,2
Zonarene                                      1,2
(Z)-Nerolidol                                 1,2
trans-Cadina-1,4-diene                        1,2
10-epi-Cubebol                                1,2
[alpha]-Cadinene *                            1,2
cis-Sesquisabinene hydrate                    1,2
[alpha]-Calacorene                            1,2
Selina-3,7(11)-diene                          1,2
Hedycaryol                                    1,2
Elemol                                        1,2
trans-Dauca-4(11),7-diene                     1,2
Silphiperfol-5-en-3-ol A                      1,2
Germacrene B *                                1,2
[beta]-Calacorene                             1,2
(E)-Nerolidol                                1,2,3
Palustrol                                     1,2
Dendrolasin                                   1,2
(Z)-Dihydroapofarnesol                        1,2
Spathulenol                                   1,2
Caryophyllene oxide                           1,2
Thujopsan-2-[alpha]-ol                        1,2
Globulol                                      1,2
Salvial-4(14)-en-1-one                        1,2
Viridiflorol                                  1,2
Ledol                                         1,2
5-epi-7-epi-[alpha]-Eudesmol                  1,2
Humulene epoxide II                           1,2
1,10-di-epi-Cubenol                           1,2
Junenol                                       1,2
1-epi-Cubenol                                 1,2
(E)-Sesquilavandulol                          1,2
cis-Cadin-4-en-7-ol                           1,2
epi-[alpha]-Cadinol (=T-Cadinol) *            1,2
epi-[alpha]-Muurolol (=T-Muurolol)            1,2
Cubenol                                       1,2
[alpha]-Muurolol (=Torreyol) *                1,2
[alpha]-Cadinol *                             1,2
Selin-11-en-4-[alpha]-ol                      1,2
neo-Intermedeol                               1,2
cis-Calamenen-10-ol                           1,2
Intermedeol                                   1,2
trans-Calamenen-10-ol                         1,2
14-Hydroxy-9-epi-[beta]-                      1,2
  caryophyllene
Cadalene                                      1,2
Mustakone                                     1,2
Khusinol                                      1,2
epi-[alpha]-Bisabolol                         1,2
Germacra-4(15),5,10(4)-                       1,2
  trien-1-[alpha]-ol
[alpha]-Bisabolol                             1,2
Eudesma-4(15),7-dien-1-[beta]-ol              1,2
Eudesm-7(11)-en-4-ol                          1,2
Heptadecane                                  1,2,3
Amorpha-4,9-dien-2-ol                         1,2
10-Nor-Calamenen-10-one                       1,2
Pentadecanal                                  1,2
Isobicyclogermacrenal                         1,2
Mint sulfide                                  1,2
2-[alpha]-Hydroxy-amorpha-                    1,2
  4,7(11)-diene
Hexadecanal                                   1,2
6,10,14-Trimethyl-2-pentadecanone             1,2
Farnesyl acetone                              1,2
Hexadecanoic acid                            1,2,3
Ethyl hexadecanoate                           1,2
(Z,E)-Geranyl linalool                        1,2
(6E,10Z)-pseudo Phytol                        1,2
(Z)-Phytol                                    1,2
(E)-Phytol                                    1,2
Linolenic acid                                1,2
Docosane                                     1,2,3
Tricosane                                    1,2,3
Pentacosane                                  1,2,3
Hexacosane                                   1,2,3
Heptacosane                                  1,2,3
Octacosane                                   1,2,3
Nonacosane                                   1,2,3
Triacontane                                  1,2,3
Untriacontane                                1,2,3

Total
Compounds

(a) Compounds listed in order of elution from 5 % phenyl/95 %
dimethylpolysiloxane column. (b) RI = Retention index relative to
[C.sub.8]/[C.sub.32] n/alkanes on the 5 % phenyl/95 %
dimethylpolysiloxane column. (c) Lit. RI= (Adams, 2007). (d) Compound
class: A, aliphatics; B, benzenoids; D, diterpenoids; IT, irregular
terpenoids; M, monoterpenoids; Misc, miscellaneous; PP,
phenylpropanoids; S, sesquiterpenoids. eMethod: 1 = Retention index
on 5 % phenyl/95 % dimethylpolysiloxane. 2 = MS spectra. 3 =
Standard. (f) (Jordan, Margaria, Shaw, & Goodner, 2002). (g)
(Radulovic, Dordevic, & Palic, 2010). (h) (Ali et al., 2008). (i)
(Zoghbi et al., 1998). (j) (Flamini et al., 2003).
t: traces (<0.05 %). Blank space = not detected. Asterisk * =
compounds reported previously in Albuquerque et al. (2004) and
Sobrinho et al. (2016). Bullet ** = compounds reported in Rojas et
al. (2008).

TABLE 2
The chemical class distribution in the essential oils of Baccharis
trinervis from three locations in Costa Rica

Compound class                               Miramar

                                Leaf %   NC    Flower %    NC

Aliphatics (A)                    t       9      0.9       28
  Alcohols                                        t        2
  Aldehydes                       t       5      0.6       10
  Ketones                         t       1       t        2
  Acids
  Esters                          t       1      0.1       2
  Hydrocarbons                    t       2      0.2       12
Terpenoids                       97.0    106     94.5      96
Monoterpenoids (M)               15.3    51      7.3       41
  Monoterpene hydrocarbons       10.8    21      5.5       19
  Oxygenated monoterpenes        4.5     30      1.8       22
Sesquiterpenoids (S)             81.7    55      86.6      52
  Sesquiterpene hydrocarbons     17.1    32      63.4      34
  Oxygenated sesquiterpenes      64.6    23      22.7      17
  Sulfur sesquiterpenes                          0.5       1
Dilerpenoids (D)                                 0.3       2
  Irregular terpenoids (IT)                      0.3       1
Aromatics                        0.3      5      0.1       2
  Benzenoids (B)                 0.1      4      0.1       2
  Phenylpropanoids (PP)          0.2      1
Miscellaneus (Mise)               t       1      0.1       3

TOTAL                            97.3    121     95.6     129

Compound class                             San Pedro          Pavas

                                Leaf %   NC   Branch %   NC   Leaf %

Aliphatics (A)                   0.2     7      0.6      9     0.4
  Alcohols                       0.2     2                      02
  Aldehydes                       t      3      0.3      8     0.1
  Ketones                                                       t
  Acids                                         0.3      1
  Esters                                 1                     0.1
  Hydrocarbons                           1
Terpenoids                       95.8    83     97.8     80    92.7
Monoterpenoids (M)               20.7    34     10.4     24    27.8
  Monoterpene hydrocarbons       20.1    19     10.1     13    24.7
  Oxygenated monoterpenes        0.6     15     0.3      11    3.1
Sesquiterpenoids (S)             75.1    48     87.4     55    64.9
  Sesquiterpene hydrocarbons     64.3    32     72.3     35    30.7
  Oxygenated sesquiterpenes      10.8    16     15.1     20    33.6
  Sulfur sesquiterpenes                                        0.6
Dilerpenoids (D)                                                t
  Irregular terpenoids (IT)                      t       1
Aromatics                         t      3       t       2
  Benzenoids (B)                  t      2       t       2      t
  Phenylpropanoids (PP)           t      1
Miscellaneus (Mise)                             0.2      2      t

TOTAL                            96.0    92     98.6     93    93.1

Compound class                                Pavas

                                NC    Flower %   NC   Branch %   NC

Aliphatics (A)                   9      0.9      9      0.5      11
  Alcohols                       2      0.1      1      0.1      2
  Aldehydes                      3      0.5      3      0.2      4
  Ketones                        1
  Acids                                                 0.1      1
  Esters                         3                      0.1      3
  Hydrocarbons                          0.3      5       t       1
Terpenoids                      91      92.3     72     94.9     77
Monoterpenoids (M)              38      5.6      27     27.8     25
  Monoterpene hydrocarbons      19      4.8      16     26.7     17
  Oxygenated monoterpenes       19      0.9      12     1.1      8
Sesquiterpenoids (S)            52      86.6     45     67.1     50
  Sesquiterpene hydrocarbons    34      47.4     30     46.9     30
  Oxygenated sesquiterpenes     17      38.8     14     20.1     19
  Sulfur sesquiterpenes          1      0.4      1      0.1      1
Dilerpenoids (D)                 1                      0.4      2
  Irregular terpenoids (IT)
Aromatics                                                t       1
  Benzenoids (B)                 1                       t       1
  Phenylpropanoids (PP)                 0.2      1
Miscellaneus (Mise)              1       t       1      1.0      1

TOTAL                           102     93.4     84     96.8     90

NC: number of compounds, t: traces (<0.05 %).
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Author:Chaverri, Carlos; Ciccio, Jose F.
Publication:Revista de Biologia Tropical
Article Type:Report
Date:Dec 1, 2017
Words:10464
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