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Chemosystematics of the Rosiflorae/Quimiossistematica de Rosiflorae.

1. Introduction

Today there are many plant classification systems. The major botanical authorities often disagree with respect to the positioning of certain taxa (Goldberg, 1986). Such discrepancies frequently concern the position of subtribes in tribes, of families in orders, and of subclasses or orders in superorders. This situation is due to the utilization of different morphological markers, as well as chiefly to the absence of unique criteria for the taxonomic evaluation of the markers (Gottlieb et al., 1996).

Recent developments in plant chemosystematics, represented by the demonstration of basic principles (Gottlieb, 1982), confirmed the relevance of special metabolites in phylogenetic studies. Thus correlation among chemical characters and numerical parameters referring to oxidation level, skeletal specialization and protection of flavonoid hydroxyls with plant taxonomic positioning is a promising subject for study.

The superorder Rosiflorae (Dahlgren, 1980) belongs to the Angiospermae and comprises twelve orders (Fagales, Cunoniales, Saxifragales, Rosales, Juglandales, Myricales, Balanopales, Casuarinales, Trochodendrales, Hamamelidales, Gunnerales and Buxales) and thirtyeight families formed by species with varied habits and a wide distribution in temperate regions. Dahlgren, in his first system of classification for Angiospermae (Dahlgren, 1975), placed the families of Rosiflorae in three superorders: Hamamelidanae, Rosanae and Saxifraganae allied with other families and orders. In 1989, an important system of classification for the flowering plants appeared showing modifications in the neighbourhood in Rosanae orders former (Rosiflorae) (Dahlgren, 1989; 1995). In Cronquist's system of classification (Cronquist, 1981), Dahlgren's Rosiflorae is separated in two Subclasses: Hamamelidae (15 families in 7 orders) and Rosidae (16 families in 4 orders).

The positioning of the Rosiflorae (or Rosanae) families shows great controversy according to recent botanists (Goldberg, 1986). In order to analyse the validity of the positioning of the families and orders into superorders in Rosiflorae, a detailed study of micromolecular composition of the Rosiflorae families has been made.

The present work attempts to look for the phylogenetic affinities in Rosiflorae. The flavonoids and triterpenoids were selected as chemosystematic markers for this purpose, due to their general occurrence and diversification in this superorder.

2. Material and Methods

Chemical data were collected from Chemical Abstracts and from specific literature surveys. Selected micromolecules were tabulated with the occurrence number (ON = number of compounds of a chemical class produced by a taxon) and correlated with respect to their evolutionary parameters determined according to chemosystematic methodology (Gottlieb, 1982). The occurrence numbers were used as a base for calculation of flavonoid chemical indexes (Figure 1 and 2). Evolutionary advancement parameters related to the orders were evaluated by the weighted average of their flavonoid chemical indexes (Barreiros, 1990). These parameters were further correlated to each other and to the chemo-morphological and morphological indexes: the herbaceousness index (HI) (Borin, 1993) and the Sporne index (SI) (Sporne, 1980). The systems of classification used for taxa of flowering plants circumscription were those of Dahlgren (1980) and of Brummitt (1992).

[FIGURE 1 OMITTED]

[FIGURE 2 OMITTED]

3. Results and Discussion

Among the botanists specialized in plant taxonomy, there are differences in opinion with respect to the systematic positioning of some families in Rosiflorae. However, for many families, total agreement is observed in their classification systems. The families Fagaceae, Betulaceae and Corylaceae are invariably positioned in the order Fagales. The families Casuarinaceae and Rosaceae are classified, respectively, in the orders Casuarinales and Rosales. Neuradaceae for modern botanists is positioned in Rosales, however Emberger (1960), Hutchinson (1973), Benson (1979) and Thorne (1983), consider Neurada a genus of Rosaceae. The same happens with all genera of Chrysobalanaceae, which Hutchinson (1973) maintains included in Rosaceae (Goldberg, 1986).

By contrast, most of the Rosiflorae families exhibit different positionings outside the superorder. Melchior (1964), Benson (1979), Cronquist (1981) and Rouleau (1981) classify Buxaceae in Euphorbiales; Takhtajan (1983) in Hamamelidales, suborder Buxineae; Thorne (1983) in Pittosporales, suborder Buxineae; Emberger (1960) in Terembinthales; Melchior (1964) in Celastrales, suborder Buxineae; Dahlgren (1980) and Young (1981) in Buxales. Grubbiaceae is another example of uncertain positioning. According to Emberger (1960), Melchior (1964), Hutchinson (1973) and Benson (1979), it is classified in Santalales; while for Stebbins (1974), Cronquist (1981), Rouleau (1981) and Takhtajan (1983) it is in Ericales, whilst for Young (1981) and Thorne (1983) it is in Pittosporales, but for Dahlgren (1980) it is in Cunoniales (Goldberg, 1986).

3.1. Chemical profile of Rosiflorae

In Rosiflorae families, approximately 60% of the families have undergone some chemical study. The main special metabolites of these plants are biosynthesized through the shikimic acid pathway but very representative terpenoids are also produced (Castilho, 1997).

The special metabolism of Rosiflorae to date is characterized by: flavonoids, condensed and hydrolysable tannins, cinnamic and benzoic acid derivatives, alkaloids, mono and triterpenes, carotenes and steroids, among others (Figure 3).

Monoterpenes have been isolated from eight families of Rosiflorae. In Rosaceae they are the largest representatives, belonging mainly to canfeno, pineno and cimeno types. These metabolites appear mainly in Bruniaceae, Hamamelidaceae, Saxifragaceae, Fagaceae, Myricaceae, Betulaceae and Juglandaceae.

Iridoids are very rare in Rosiflorae: Buxaceae having only one representative, buxeletin; Daphniphyllaceae, with three representatives, such as: asperuloside, daphylloside and geniposidic acid; and Hamamelidaceae with two representatives from the genus Liquidambar, asperuloside and monotropein.

The sesquiterpenes of Rosiflorae are sparsely distributed in five families and they are represented mainly by caryophyllene, humulene, eudesmene, cadinene and germacrene.

In Rosiflorae the presence of diterpenes is rare, registered only in three families, Crassulaceae with one labdane representative, Rosaceae with representatives of the kaurene and abietane types and Chrysobalanaceae with representatives of the kaurene types.

Triterpenes are found in almost all studied Rosiflorae families, with a large occurrence and great structural diversity in Rosaceae and Betulaceae.

The Rosiflorae flavonoids are represented mainly by flavonols, which constitute more than 50% of all isolated flavonoids from this taxon.

Tannins are commonly found in Rosiflorae, having predominant distribution of polygalloyl-ellagoyl glucose in all families. Condensed tannins are recorded for the superorder occurring mainly in Rosaceae, Myricaceae, Saxifragaceae and Crassulaceae. Another group of substances usually found in the Rosiflorae families, mainly in Rosaceae, are aromatic acids, such as: cinnamic, caffeic, ferulic, vanillic, sinapic and benzoic acids (Geissman and Crout, 1969).

Steroid chemistry is simple involving fifteen families. The more common structural types are: colestane, stigmastane and ergostane, apart from the Crassulaceae family which produces highly oxydised bufadienolides.

Ten Rosiflorae families produce alkaloids. They belong to the types: spermidine/guanidine/piperidine/ pyrrolizidine/indolic/Daphyniphyllum/triterpene and diterpene alkaloids. Attention should be given to the presence of a pyrrolizidine alkaloid in Casuarinaceae of the same type as produced by Crotalaria, Leguminosae (Castilho et al., 1999).

Other more restricted chemical classes of compounds produced by some Rosiflorae families are: diarylheptanoids in Myricaceae; phloroglucinol derivatives (common in ferns) in Rosaceae (Murakami and Tanaka, 1988); lignans are restricted to three families: Casuarinaceae, Gunneraceae and Rosaceae; coumarins to Rosaceae, Crassulaceae, Buxaceae and Saxifragaceae; hydroquinone glycosides as arbutin in Fagaceae, Juglandaceae, Casuarinaceae, Buxaceae, Saxifragaceae and Rosaceae; anthraquinones as emodin and chrysophanol in Saxifragaceae and Rosaceae.

Analysis of the chemical profile for Rosiflorae orders (Table 1), excluding Buxales, shows a good homogeneous production of secondary metabolites. On the basis of these data, flavonoids and triterpenoids were shown to be real taxonomic markers for the taxon, due not only to the large number of occurrences, but also to their high structural diversity. On the other hand, alkaloids may be suitable as chemical markers only for the order Buxales (Castilho, 1997).

3.2. Flavonoid evolution in Rosiflorae

Flavonoids constitute a special category of metabolite derived by a mixed (acetate-mevalonate/shikimate) biosynthetic pathway (Torssell, 1983). The potentiality of these compounds as systematic markers is due not only to their ubiquity in all Metaphyta but also to their great structural diversity (Barreiros, 1990).

Flavonoid chemistry is quite diversified in Rosiflorae and it reveals some evolutionary polarizations of great chemosystematic value. Rosaceae is the family that presents the largest flavonoid occurrence number (ON) in the superorder, followed by Saxifragaceae and Crassulaceae. The other families are not so expressive, presenting ON less then 100 (Figure 4).

[FIGURE 4 OMITTED]

Among twenty-three Rosiflore families chemically studied, twenty were shown to have produced flavonoids, nineteen of them were shown to have a preponderance of flavonols and in only nine families flavone production has been recorded. The flavonoid profile for Rosiflorae shows flavonols (54%), anthocyanidins (20%), flavones (8%), flavanones (7%), dihydroflavonols (4%), flavan3-ols (4%) and others (3%) including chalcones, dihydrochalcones, isoflavonoids, biflavonoids and flavans (Figure 5). The occurrence of flavonols generally prevails in the most primitive plants (Harborne and Turner, 1984; Gottlieb and et al., 1996). This happens for the superorder Rosiflorae, suggesting a low "evolutionary status" for the taxon. This proposal can be strengthened by analysis of the flavone/flavonol ratio (Figure 6), which is very low for most of the studied families, and also for the whole superorder (Soares and Kaplan, 2001). Analysis of the hydroxyl protection mechanism for the Rosiflorae flavonoids states that 69% of hydroxyls are protected. Among them 49% are protected by glycosylation only, 11% by methylation only and 9% receive double protection (methylation and glycosylation) (Figure 7). Once again, this high percentage of protection by glycosylation (49%), together with the percentage of unprotected glycosyls (31%), indicates a more primitive character for the superorder.

In the order Trochodendrales, the family Eupteleaceae produces flavonols and dihydroflavonols with free and protected hydroxyl groups in close percentages; Cercidiphyllaceae exhibit only dihydroflavonols with unprotected hydroxyl groups, but that order does not show transformation of the A-ring flavonoids (Table 2).

In Hamamelidales, the family Hamamelidaceae biosynthesises anthocyanidins, flavonols, dihydroflavonols and flavan-3-ols all have a high proportion of unprotected hydroxyls and when they are protected, the mechanism is through glycosylation. Platanaceae only produce flavonol glycosides.

[FIGURE 6 OMITTED]

Fagaceae is one family of Fagales with a high diversity of flavonoid structural types with low hydroxyl protection and when this happens it is by glycosylation. On the other hand, in Betulaceae, 84% of flavonoid hy droxyls are protected by methylation and/or glycosylation. Corylaceae follows the same pattern, but in this case the protection is only made by glycosylation.

Saxifragales is the order that presents the largest index of A-ring transformation. The flavonoids found in Saxifragaceae have their hydroxyl groups mainly protected by methylation, glycosylation, or for double protection (glycosylation and methylation). In this family, the methylation protection mechanism is preferentially used in the genus Chrysosplenium, justifying the highest evolutionary advancement methylation index (EAM) indicating its advanced positioning. The flavonoids of Crassulaceae have the largest A-ring transformation in the order, but its hydroxyl groups are protected mainly by glycosylation.

In Superorder Rosiflorae, Rosaceae stands out for being the family that shows the largest flavonoid number of occurrence and produces the greatest variety of structural types. These flavonoids have their hydroxyl groups protected by glycosylation (53%) and 34% being free, proving the low "evolutionary status" of the family.

Correlation of the flavonoid chemosystematic parameters with the herbaceousness index (HI) and Sporne index (SI), allows visualization of valuable evolutionary tendencies inside the superorder. A positive correlation is observed when the herbaceousness index (HI) and Sporne index (SI) are compared, with the chemosystematic evolutionary advancement parameter of the flavonoid hydroxyl protection by glycosylation (EAG) for the of Rosiflorae families (Figure 8a,b). These Figures demonstrate that taxa of the Rosiflorae preferentially use the glycosylation mechanism to protect their flavonoid hydroxyls. The families of Saxifragales are a closely related and more developed group, while the families of Trochodendrales were shown to be less developed. The families of the other orders have an intermediary positioned.

[FIGURE 8 OMITTED]

The systematic indexes: herbaceousness index (HI) and the Sporne index (SI) were compared with the flavonoid protection parameter. When evolutionary advancement parameters for methylation index (EAM) are compared, it is observed that Buxaceae presents a prominent position, showing that the protection of its flavonoid hydroxyls is mainly by means of methylation. This fact separates Buxaceae from Daphniphyllaceae. Evidence of Betulaceae is also shown by being separated from Fagaceae and Corylaceae. The positioning of Saxifragales should be noted in that its families form a closed group, positioned at a higher evolutionary level. The other families are grouped together in a small homogeneous range, demonstrating that the Rosiflorae flavonoid hydroxyl groups in general are not protected by methylation (Figures 9a,b).

[FIGURE 9 OMITTED]

Correlations of the herbaceousness index (HI) and the Sporne index (SI) with the total protection evolutionary advancement parameters (EATP), revealed the prominence of the family Buxaceae relative to the other families of the superorder. The families of Saxifragales, were still shown to be closely related and positioned in the highest advancement level.

4. Conclusion

The results of chemosystematics analysis: the ubiquitous production of flavonols in detriment of other flavonoid type metabolites resulted in a very low flavone/ flavonol ratio; the high degree of unprotected flavonoid hydroxyls (31%) and preferential hydroxyl protection by glycosylation mechanism (49%) in contrast to methylation (11%) and double protection (9%) mechanism; besides the low level of A-ring transformation, confirm the primitive positioning of the superorder Rosiflorae according to the botanists.

Acknowledgements--The authors are grateful to CNPq for finanancial support and to Mrs Marylin Davies for comments.

Received October 20, 2006--Accepted December 11, 2006--Distributed August 31, 2008 (With 9 figures)

References

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BORIN, MRMB., 1993. Polifenois: indicadores da evolucao de plantas floriferas. Sao Paulo: Instituto de Quimica, Universidade de Sao Paulo. [Doctor Thesis].

BRUMMITT, RK., 1992. Vascular plant families and genera. Kew: Royal Botanical Gardens.

CASTILHO, RO., 1997. Tendencias filogeneticas em Rosiflorae. Rio de Janeiro: Nucleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro. [Master Thesis].

CASTILHO, RO., BULHOES, AGS. and KAPLAN, MAC., 1999. Controversy in Buxales systematic positioning. Nord. J. Bot. vol. 19, no. 5, p.541-546.

CRONQUIST, A., 1981. An integrated system of classification of flowering plants. New York: The New York Botanical Garden; Columbia University Press.

DAHLGREN, G., 1989. An updated angiosperm classification. Bot. J. Linn. Soc. vol. 100, no.3, p. 197-203.

-, 1995. On Dahlgrenograms--a system for the classification of angiosperms and its use mapping characters. An. Acad. Bras. Cienc. vol. 67, Supp. 3, p. 383-404.

DAHLGREN, RMT., 1975. A system of classification of angiosperms to be used to demonstrate the distribution of characters. Bot. Notiser, vol. 128, p. 119-147.

DAHLGREN, RMT., 1980. A revised system of classification of the angiosperms. Bot. J. Linn. Soc. vol. 80, no.2, p. 91-124.

GEISSMAN, TA. and CROUT, DHG., 1969. Organic Chemistry of Secondary Metabolism. San Francisco: Freeman Cooper & Co.

GOLDBERG, A., 1986. Classification, evolution and phylogeny of the families of dicotyledons. Washington: Smithsonian Institution Press.

GOTTLIEB, OR., KAPLAN, MAC., BORIN, MRMB., 1996. Biodiversidade--Um enfoque Quimico Biologico. Rio de Janeiro: Editora UFRJ.

GOTTLIEB, OR., 1982. Micromolecular evolution, systematics and ecology: na essay into a novel botanical discipline. Berlin: Springer-Verlag.

HARBORNE, JB. and TURNER, BL., 1984. Plant Chemosystematics. London: Academic Press Inc.

MURADAMI, T. and TANAKA, N., 1988. Progress in the chemistry of organic natural products. Berlin: Springer-Verlag.

SOARES, GLG. and KAPLAN, MAC., 2001. Study of flavone-flavonol ratio in Dicotyledonae. Bot. J. Linn. Soc. vol. 135, no. 1, p. 61-66.

SPORNE, KR., 1980. A re-investigation of character correlations among dicotyledons. New Phytology vol. 91, p. 137-145.

TORSSEL, KBG., 1983. Natural Product Chemistry-A mechanistic and biosynthetic approach to secondary metabolism. New York: John Wiley & Sons Ltd.

Castilho, RO. (a) * and Kaplan, MAC. (b)

(a) Departamento de Produtos Farmaceuticos, Faculdade de Farmacia, Campus UFMG-Pampulha, Universidade Federal de Minas Gerais--UFMG, Av. Presidente Antonio Carlos, 6627, CEP 31270-901, Belo Horizonte, MG, Brazil

(b) Nucleo de Pesquisas de Produtos Naturais, Centro de Ciencias da Saude, Universidade Federal do Rio de Janeiro--UFRRJ, Bloco H, Cidade Universitaria, CEP 21941-590, Rio de Janeiro, RJ, Brazil

* e-mail: roc2006@farmacia.ufmg.br
Table 1. Chemical Profile (ON) of families (aceae) of superorder
Rosiflorae.

Chemical
Class/ Families     MON     IRI     SES     DIT     TRI

Trochodendr         --      --      --      --      4
Euptele             --      --      --      --      24
Cercidiphyll        --      --      --      --      --
Hamamelid           14      2       3       --      6
Platan              --      --      --      --      8
Fag                 11      --      --      --      218
Coryl               --      --      --      --      1
Bet                 2       --      7               44
Jugland             3       --      --      --      1
Myric               11      --      9       --      22
Casuarin            --      --      1       --      8
Bux                 --      1       --      --      17
Daphniphyll         --      3       --      --      --
Davdisoni           --      --      --      --      3
Eucryphi            --      --      --      --      --
Bruni               --      --      --      --      --
Crassul             --      --      --      1       15
Cephalot            --      --      --      --      --
Franco              --      --      --      --      --
Saxifrag            14              --      --      11
Gunner              --      --      --      --      24
Ros                 75      --      7       4       61
Chrysobalan         --      --      --      --      2

Chemical
Class/ Families     CAR     STE     ALK     TAN     BCD

Trochodendr         --      --      --      --      --
Euptele             --      2       --      --      --
Cercidiphyll        --      --      --      --      --
Hamamelid           3       6       --      22      --
Platan              --      2       --      --      --
Fag                 19      30      4       70      25
Coryl               12      1       2       5       --
Bet                 38      3       17      8       5
Jugland             1       2       --      9       9
Myric               1       --      1       10      --
Casuarin            --      7       1       12      --
Bux                 --      3       242     --      --
Daphniphyll         --      1       49      --      --
Davdisoni           --      --      --      7       --
Eucryphi            --      --      --      --      --
Bruni               --      --      1       --      --
Crassul             1       80      59      8       64
Cephalot            --      --      --      --      --
Franco              --      --      --      --      --
Saxifrag            --      3       --      --      34
Gunner              --      8       --      --      --
Ros                 301     52      29      86      486
Chrysobalan         --      3       --      1       --

Chemical
Class/ Families     FLA     COU     HYD     ANT     LIG

Trochodendr         --      --      --      --      --
Euptele             2       --      --      --      --
Cercidiphyll        5       --      --      --      --
Hamamelid           34      --      --      --      --
Platan              7       --      --      --      --
Fag                 41      --      --      --      --
Coryl               16      --      --      --      --
Bet                 81      --      --      --      --
Jugland             15      --      26      --      --
Myric               35      --      --      --      --
Casuarin            49      --      1       --      --
Bux                 --      3       1       --      --
Daphniphyll         2       --      --      --      --
Davdisoni           11      --      --      --      --
Eucryphi            42      --      --      --      --
Bruni               --      --      --      --      --
Crassul             240     13      --      --      --
Cephalot            9       --      --      --      --
Franco              6       --      --      --      --
Saxifrag            445     23      11      2       --
Gunner              --      --      --      --      1
Ros                 579     29      1       5       4
Chrysobalan         3       --      --      --      --

MON = Monoterpenes, IRI = Iridoids, SES = sesquiterpenes,
DIT = Diterpenes, TRI = Triterpenes, CAR = Carotenoids,
STE = Steroids, ALK = Alkaloids, TAN = Tannins, BCD = Benzoic
and Cinnamic acids derivatives, FLA = Flavonoids, COU = Coumarins,
HYD = Hydroquinone, ANT = anthraquinones and LIG = Lignins.

Table 2. Sporne index (SI) and herbaceousness index (HI) and flavonoid
chemical index ([EA.sub.M], [EA.sub.G, [EA.sub.MG], [EA.sub.U] e
[E.sub.AT]) for Rosiflorae taxa.

Orders/Families        HI            SI

TROCHODENDRALES
  Trochodendraceae     1,0           33
  Tetracentraceae      1,0           33
  Eupteleaceae         25,0          35
  Cercidiphyllaceae    1,0           26
HAMAMELIDALES
  Hamamelidaceae       25,0          37
  Platanaceae          1,0           41
  Myrothamnaceae       50,0          33
  Geissolomataceae     50,0          33
FAGALES
  Fagaceae             25,0          43
  Corylaceae           25,0          41
  Betulaceae           25,0          38
BALANOPALES
  Balanopaceae         1,0           38
JUGLANDALES
  Rhoipteliaceae       1,0           40
  Juglandaceae         12,5          50
MYRICALES
  Myricaceae           25,0          50
CASUARINALES
  Casuarinaceae        25,0          50
BUXALES
  Buxaceae             75,0          36
  Daphniphyllaceae     25,0          38
CUNONIALES
  Cunoniaceae          25,0          40
  Baueraceae           50,0          42
  Ribesiaceae          50,0          42
  Brunelliaceae        1,0           43
  Davidsoniaceae       1,0           37
  Eucryphiaceae        25,0          35
  Bruniaceae           37,5          54
  Grubbiaceae          50,0          42
SAXIFRAGALES
  Crassulaceae         75,0          55
  Cephalotaceae        100,0         60
  Iteaceae             25,0          54
  Francoaceae          100,0         54
  Saxifragaceae        75,0          48
  Vahliaceae           100,0         54
  Greviaceae           25,0          54
GUNNERALES
  Gunneraceae          100,0         54
ROSALES
  Crossosomataceae     50,0          43
  Rosaceae             50,0          43
  Neuradaceae          100,0         60
  Chrvsobalanaceac     25,0          48

Orders/Families        [EA.sub.M]    [EA.sub.G]

TROCHODENDRALES
  Trochodendraceae     --            --
  Tetracentraceae      --            --
  Eupteleaceae         0,00          0,10
  Cercidiphyllaceae    0,00          0,00
HAMAMELIDALES
  Hamamelidaceae       0,02          0,13
  Platanaceae          0,00          0,23
  Myrothamnaceae       --            --
  Geissolomataceae     --            --
FAGALES
  Fagaceae             0,01          0,11
  Corylaceae           0,02          0,19
  Betulaceae           0,30          0,04
BALANOPALES
  Balanopaceae         --            --
JUGLANDALES
  Rhoipteliaceae       --            --
  Juglandaceae         0,03          0,18
MYRICALES
  Myricaceae           0,08          0,09
CASUARINALES
  Casuarinaceae        0,06          0,09
BUXALES
  Buxaceae             0,75          0,08
  Daphniphyllaceae     0             0,10
CUNONIALES
  Cunoniaceae          --            --
  Baueraceae           --            --
  Ribesiaceae          --            --
  Brunelliaceae        --            --
  Davidsoniaceae       0,00          0,14
  Eucryphiaceae        0,11          0,16
  Bruniaceae           --            --
  Grubbiaceae          --            --
SAXIFRAGALES
  Crassulaceae         0,07          0,21
  Cephalotaceae        0,00          0,13
  Iteaceae             --            --
  Francoaceae          0,07          0,18
  Saxifragaceae        0,23          0,15
  Vahliaceae           --            --
  Greviaceae           --            --
GUNNERALES
  Gunneraceae          --            --
ROSALES
  Crossosomataceae     --            --
  Rosaceae             0,14          0,11
  Neuradaceae          --            --
  Chrvsobalanaceac     0,00          0,06

Orders/Families        [EA.sub.MG]   [EA.sub.U]   [EA.sub.AT]

TROCHODENDRALES
  Trochodendraceae     --            --           --
  Tetracentraceae      --            --           --
  Eupteleaceae         0,10          0,90         0,00
  Cercidiphyllaceae    0,00          1,00         0,00
HAMAMELIDALES
  Hamamelidaceae       0,15          0,85         0,04
  Platanaceae          0,23          0,77         0,00
  Myrothamnaceae       --            --           --
  Geissolomataceae     --            --           --
FAGALES
  Fagaceae             0,19          0,80         0,18
  Corylaceae           0,21          0,79         0,00
  Betulaceae           0,34          0,65         0,07
BALANOPALES
  Balanopaceae         --            --           --
JUGLANDALES
  Rhoipteliaceae       --            --           --
  Juglandaceae         0,20          0,80         0,00
MYRICALES
  Myricaceae           0,20          0,80         0,32
CASUARINALES
  Casuarinaceae        0,15          0,85         0,17
BUXALES
  Buxaceae             0,08          0,17         1,00
  Daphniphyllaceae     0,10          0,90         0,00
CUNONIALES
  Cunoniaceae          --            --           --
  Baueraceae           --            --           --
  Ribesiaceae          --            --           --
  Brunelliaceae        --            --           --
  Davidsoniaceae       0,14          0,86         0,00
  Eucryphiaceae        0,25          0,74         0,00
  Bruniaceae           --            --           --
  Grubbiaceae          --            --           --
SAXIFRAGALES
  Crassulaceae         0,30          0,70         0,48
  Cephalotaceae        0,13          0,86         0,00
  Iteaceae             --            --           --
  Francoaceae          0,25          0,75         0,00
  Saxifragaceae        0,36          0,60         0,35
  Vahliaceae           --            --           --
  Greviaceae           --            --           --
GUNNERALES
  Gunneraceae          --            --           --
ROSALES
  Crossosomataceae     --            0,67         --
  Rosaceae             0,28          --           0,18
  Neuradaceae          --            0,93         --
  Chrvsobalanaceac     0,07          --           0,00

Figure 3. Chemical Profile of Rosiflorae in ON (Occurrence Number)

Flavanoids                 39%
Triterpenes                11%
Alkaloids                  13%
Monotepenes                 5%
Others                      9%
Benzoic/cinnamic acids      6%
Steroids                    8%
Tannis                      4%
Carotenes                   5%

Note: Table made from pie graph.

Figure 5. Types of flavonoids in Rosiflorae (ON).

Flavonol                   54%
Anthocyanins               20%
Flavone                     8%
Flavonone                   7%
Dihydroflavanol             4%
Flavan-3-ol                 4%
Others                      3%

Note: Table made from bar graph.

Figure 7. Protection of hydroxyls of Rosiflorae flavonoids.
Gly = Glycosylation, Methyl = Methylation, Methyl/Gly =
Methylation/glycosilation (double protection).

Gly                        49%
Methyl                     11%
Methyl/Gly                  9%
Unprotected                31%

Note: Table made from pie graph.
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Author:Castilho, R.O.; Kaplan, M.A.C.
Publication:Brazilian Journal of Biology
Date:Aug 1, 2008
Words:3466
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