Contact Toxicity and Repellency of the Essential Oil from Bupleurum bicaule Helm against Two Stored Product Insects.
1. IntroductionThe economy of agriculture and food industry has been threatened by insects in the process of production, transportation, and storage. It is estimated that about 10-40% of the world's annual stored product loss was caused by the insects [1]. The cigarette beetle (Lasioderma serricorne Fabricius) and the booklouse (Liposcelis bostrychophila Badonnel) are two major insects in the warehouses of stored foods, grains, and some herbal medicines [2, 3]. Under appropriate environmental conditions, they can reproduce rapidly [4, 5]. The insects not only consume the stored commodities, but also lead to contamination and deterioration of stored products in the short term. A great effort has been focused on the prophylaxis of insects in stored products. Many methods, such as the cold storage, the light traps, and the chemical treatment [5] have been successively used to control the insects. Among them the chemical treatment is the most commonly used method with different chemical synthetic insecticides. However, a series of negative effects such as insecticide residues and environmental damage have been exposed, so that the development of the new environmental friendly, economical, and effective methods [2, 6] is necessary. Antagonistic storage, a traditional method, has been used for Chinese medicinal material conservation for a long history. Our ancestors skillfully used the special odors of some Chinese herbs to repel the insects and to achieve the purpose of protecting another kind of medicinal materials [7]. For instance, Rhizoma Alismatis is easily infected by insects. If it is stored with Cortex Moutan which has a special odor, Rhizoma Alismatis would not be susceptible to insects, and the quality of the two medicinal materials would be maintained for a long time [8]. The antagonistic storage method is mostly related to the special odor reeked off by the stored materials. Thus, the essential oils of the stored materials could be considered as the effective elements in antagonistic storage method. The research on the essential oils would be helpful to reveal the mechanism of the antagonistic storage method. In practice, this kind of research has become a hot topic in the field of controlling stored product insects [9-11].
Bupleurum bicaule Helm (Chinese name: Zhuiye Chaihu) is widely distributed in northeast region of China, and its roots have been medicinally used for the treatment of fever, cold, hypochondriac pain, hepatitis, biliary tract infection, irregular menstruation, uterine prolapse, and anal prolapse [12-15]. As is well known, essential oils are abundant in Umbelliferae (Apiaceae) plants [16]. Many of these essential oils obtained from Umbelliferae (Apiaceae) plants have been proven to possess insecticidal activities against certain kinds of insects. For examples, the essential oil of Heracleum persicum showed fumigant toxicity against Callosobruchus maculatus [17], Pimpinella anisum essential oil also showed strong fumigant toxicity against Ephestia kuehniella and Sitophilus oryzae [18], and Ferula asafetida essential oil possessed strong repellent activity against Tribolium castaneum [19].
The phytochemistry of Bupleurum plants has been investigated, and some of the secondary metabolites obtained from B. salicifolium showed antifeedant activity against Spodoptera littoralis [20]. For B. bicaule, the chemical components of the essential oil obtained from this plant have been reported [21]. In this work, the essential oil of B. bicaule was further investigated, and its insecticidal and repellent activities against the cigarette beetles and booklice adults were evaluated; meanwhile, the same kinds of biological activity tests were carried out with four representative compounds identified in the sample of the essential oil.
2. Materials and Methods
2.1. Plant Materials and Preparation of the Essential Oil. Roots of B. bicaule were collected in Hailar, Inner Mongolia Autonomous Region, China (northern latitude: 9[degrees]5'-19[degrees]27'; east longitude: 119[degrees]30'-120[degrees]35') in August 2016. The species was identified by Dr. Yan H. (National Institutes for Food and Drug Control, China Food and Drug Administration, China). The voucher specimen (NIFDC-20160801-01) was deposited at Herbarium (NIFDC) of National Institutes for Food and Drug Control. After air drying for one week (25-28[degrees]C and 13-20% RH), the dried roots (2.4 kg) were ground to powders with a grinding mill. The extraction of essential oil was carried out by hydrodistillation using a modified Clevenger apparatus for 8 h [22]. The distilled oils were dried over anhydrous sodium sulfate and stored in glass vials at 4[degrees]C.
2.2. GC-MS and GC-FID Analysis. The GC-MS analysis of B. bicaule essential oil was performed by an Agilent 6890N GC/MS instrument equipped with an Agilent 5973N mass selective detector and a HP-5 MS column (30 m x 0.25 mm x 0.25 [micro]m). The carrier gas was helium, and the flow rate was 1.0 mL/min. Analytical conditions are as follows: column temperature was programmed from 50[degrees]C (2 min) to 150[degrees]C at 2[degrees]C/min and kept isothermal for 2 min, then increased to 250[degrees]C at 10[degrees]C/min, and held for 5 min. The injector temperature was 250[degrees]C. The MS spectra were obtained in the electron-impact mode with ionization energy of 70 eV, and mass range was from m/z 50 to 550.
The essential oil was diluted with n-hexane to prepare a GC sample solution with content of 1% (v/v), and the sample solution of 0.1 [micro]L was injected into the instrument. Relative percentages of the individual components were determined by GC-FID via percentage peak area calculations. These components were further identified based on their retention index and by comparison with NIST 05 (Standard Reference Data, Gaithersburg, MD) and Wiley 275 GC-MS databases (Wiley, New York, NY).
2.3. Test Insects. The cigarette beetles were originally delivered from Henan University of Technology, China, since 2013, and the species was identified by Dr. Lv J. H. (School of Food Science and Technology, Henan University of Technology, China). The booklice were adopted from China Agricultural University and identified by Dr. Liu Z. L. (China Agricultural University, China). The cigarette beetles were reared on wheat flour mixed with yeast (10: 1, w/w) at 12-13% moisture content, and the booklice were cultured with the flour mixture, which was prepared with flour, yeast, and milk powder at 10:1:1 mixed proportion [2]. Insect rearing were carried out in the dark in incubators at 29-30[degrees]C and 70-80% RH. All the unsexed insects used in the experiments were one to two weeks old. The escape proof was made of polytetrafluoroethylene (Beijing Sino-Rich Co., Ltd., Beijing, China) coating on all insect containers and experimental Petri dishes.
2.4. Bioactivities
2.4.1. Preparation of the Treatment Solutions. The essential oil and four representative compounds found in the oil were selected for bioactivity assays. The chemical compounds (2E, 4E)-2,4-nonadienal and [beta]-bisabolene were purchased from TCI (Shanghai) Development Co., Ltd. (Shanghai, China). 1,4-Dimethoxy-2-tert-butylbenzene was obtained from JW&Y PharmLab (Shanghai), PharmLab Co., Ltd. (Shanghai, China). Bornyl acetate was purchased from Acros Organics Co., Ltd. (Geel, Belgium). N,N-Diethyl-3-methylbenzamide (DEET) was obtained from the National Center of Pesticide Standards (8 Shenliao West Road, Tiexi District, Shenyang, China). Each of the above samples was dissolved in the solvent of n-hexane, and their stock solutions with the known concentrations were prepared.
2.4.2. Contact Toxicity. In the evaluation of contact toxicity, two kinds of experimental methods were used based on the size of the insects. The contact toxicity against cigarette beetles was carried out with the methods described in the literature [23]. Before the formal test, the appropriate concentration range was determined by preliminary tests. Ultimately, the essential oil and four selected compounds were diluted with n-hexane into five concentrations. Drop 0.5 [micro]L dilutions on the dorsal thorax of each insect using a TopPette (0.5-10 [micro]L, Dragon Laboratory Instruments Co., Ltd., Beijing, China). Ten insects were used for each concentration, and the experiment was replicated five times for each concentration. Then the treated and control insects were transferred to glass vials (2.5 cm in diameter, 5.5 cm in height). After being cultured in an incubator (29-30[degrees]C and 70-80% R.H) for 24 h, the mortality of tested insects was observed and recorded, and the [LD.sub.50] values were calculated by Probit analysis (SPSS 20.0) [24].
For booklice, the contact toxicity was tested as described [25]. A filter paper of 5.5 cm in diameter was treated with 300 [micro]L dilutions of each test concentration. The treated filter paper was fixed in a 5.5-cm-diameter Petri dish with solid glue, and 10 test insects were placed in each Petri dish. Five concentrations (in n-hexane) and five replicates of each concentration were used. In the above experiments, n-hexane was used as a negative control. The chemical synthetic insecticide pyrethrins was usually served as a positive control; its mortality was taken from Yang et al.'s data with the same experimental methods [26]. The mortality of insects was recorded after these covered-Petri dishes were placed in an incubator at 29-30[degrees]C and 70-80% RH for 24 h. The mortality data was corrected by Abbott's formula [27]:
corrected mortality (%) = 100 x ([M.sub.c] - [M.sub.t])/(1 - [M.sub.c]), (1)
where [M.sub.t] is the observed mortality and [M.sub.c] is the control mortality. With these data, the [LD.sub.50] values were calculated by Probit analysis (SPSS 20.0).
2.4.3. Repellent Activity. The repellent activity of B. bicaule essential oil and four components against cigarette beetles and booklice was investigated with the method proposed by Zhang et al. [28]. The experiments were set with five concentrations (cigarette beetles: 78.63, 15.73, 3.15, 0.63, and 0.13 nL/[cm.sup.2]; booklice: 63.17, 12.63, 2.53, 0.51, and 0.10 nL/[cm.sup.2]) and two observation times (2 h and 4 h). For cigarette beetles, the essential oil and four selected compounds were diluted with n-hexane. Filter paper (9 cm in diameter) was symmetrically cut into two pieces, and 500 [micro]L dilution of each concentration was dropped evenly on half of the filter paper, while the other half was treated with 500 [micro]L of n-hexane as a negative control. After being air-dried for 30 s, both two pieces were stuck to the bottom of the Petri dish (9 cm in diameter) with solid glue abreast. For booklice, due to its tiny body, the diameters of the Petri dish and filter paper were reduced to 5.5 cm. Filter paper was cut into two pieces, and one piece was treated with 150 [micro]L of each solution separately. The other half (negative control) was treated with the same volume of n-hexane. For each test, 20 insects were placed at the center of the disk and covered quickly with lids. All the above procedures were repeated five times for each concentration, and each experiment was repeated three times.
As a commercial insect repellant, DEET was served as positive control. Counts of insects on each half of the paper were recorded separately. The percent repellency (PR) of each test was calculated by the following formula [23]:
PR (%) = [([N.sub.c] - [N.sub.t])/([N.sub.c] + [N.sub.t])] x 100, (2)
where [N.sub.c] is the number of insects in the negative control half and [N.sub.t] is the number of insects in the tested half. The percent repellency was transformed to arcsine square root values for analysis of variance (ANOVA), and the effect on the transformed arcsine of the percent repellency of different treatments (the essential oil, the four compounds, and the control) at each concentration and exposure time was analyzed separately. Significant differences in repellence rates among treatments were given by the analysis of Tukey's test (SPSS 20.0 for Windows 2007).
3. Results and Discussion
3.1. Chemical Constituents of the Essential Oil. The yellow essential oil was obtained from B. bicaule with a yield of 0.04% (v/w). Its chemical components were analyzed by the GC-MS. 26 compounds were identified and their relative contents in the oil sample were determined. The total amount of all the identified compounds was 85.5% (w/w) of the essential oil. The content of trans-2-isopropylbicyclo[4.3.0]non-3-en-8-one was 25.9%, and the content of 4,5-dimethyl-1,2,3,6,7,8,8a,8b-octahydrobiphenylene was 23.5%. These two compounds could be considered as the major components of the essential oil. The results are summarized in Table 1.
With the further analysis of the GS-MS results, it was found that the essential oil contained a plenty of monoterpenes and sesquiterpenes, and their contents accounted for 27.0% and 21.3% of the essential oil, respectively. The other types of chemical components included aldehydes, alkynes, and aromatic compounds. In a published paper [21], Xu and his partners reported that 19 compounds were identified in the root oil of B. bicaule collected from Inner Mongolia, China, and all the types of chemical components mentioned above also existed in Xu et al.'s oil sample. The five types of components accounted for about 60% of the essential oils in the two works. However, the significant difference between the results presented in Xu's paper and our results could be figured out. The compound with the highest content predicted in Xu's paper was 4-tridecen-6-yne (42.6%), but only its isomer, 6-tridecen-4-yne, was discovered in our sample and its content only accounted for 2.7% of the essential oil. The highest content compound in our sample was trans-2-isopropylbicyclo[4.3.0] non-3-en-8-one (25.9%), and it was not reported in the literature.
The other differences were showed in Figure 1, the content of aldehydes (12.6%) in Xu's paper was higher than that of terpenoids (6.2%), and the monoterpenes only accounted for a minor proportion (0.8%). However, in our case, the content of terpenoids was 48.3% (27.0% for monoterpenes and 21.3% for sesquiterpenes), which was much higher than that of aldehyde compounds (4.8%). The above differences might be caused by many variables such as the growth environment of plants, the harvest time, and treatment of samples. These differences might further affect the biological activities.
It was reported that terpenoids and aromatic compounds exhibited excellent bioactivities against different stored product insect pests [29-32] and aldehydes showed fair contact toxicity and repellent activities [33]. Here, four representative compounds were selected from 26 components identified in our sample as they belong to the chemical types of monoterpenes, sesquiterpenes, aldehydes, or aromatic compounds, respectively. Their bioactivity tests were evaluated as well. They are bornyl acetate, [beta]-bisabolene, (2E, 4E)2,4-nonadienal, and 1,4-dimethoxy-2-tert-butylbenzene. The molecular structures of the four selected compounds are shown in Figure 2.
3.2. Contact Toxicity. The results of contact toxicity of the essential oil and selected compounds against cigarette beetles and booklice are listed in Table 2. The results showed that the essential oil exhibited fair contact toxicity against cigarette beetles with a [LD.sub.50] value of 11.91 [micro]g/adult but expressed unobservable toxicity against booklice in our measure range.
Among the four selected compounds, (2E, 4E)-2,4-nonadienal showed the strongest toxicity against cigarette beetles ([LD.sub.50] = 2.31 [micro]g/adult) and booklice ([LD.sub.50] = 32.23 [micro]g/[cm.sup.2]). Bornyl acetate also showed certain toxicity against the two insects ([LD.sub.50] = 9.42 [micro]g/adult and 36.67 [micro]g/[cm.sup.2], resp.), while the toxicity of 1,4-dimethoxy-2-tert-butylbenzene and [beta]-bisabolene was relatively weak. No toxicity against booklice was observed for [beta]-bisabolene under the testing concentrations.
From the results, it could be calculated that the contact toxicity of (2E, 4E)-2,4-nonadienal against booklice was only 1.7 times less than that of pyrethrins ([LD.sub.50] = 18.72 [micro]g/[cm.sup.2]). In You et al.'s work [34], it was reported that the perilla aldehyde isolated from the essential oil of Purple Perilla aerial parts also showed significant contact toxicity against cigarette beetles ([LD.sub.50] = 3.82 [micro]g/adult). By the structural analysis, it was found that both of (2E, 4E)-2,4-nonadienal and perilla aldehyde have aldehyde fragment. The toxic characteristic of these compounds against insects might be related to the presence of an aldehyde group in these compounds. Therefore, the content of (2E, 4E)-2,4-nonadienal could be considered as one of the key elements which would affect the contact toxicity of the essential oil against certain kinds of insects.
3.3. Repellency. The results of the ANOVAs indicated that the repellent rate against both insects significantly differ with the different treatments. These results are given in Tables 3 and 4.
The essential oil showed strong repellency against cigarette beetles. After 2h of exposure, the percent repellency (PR) of the essential oil reached 100% at the highest concentration (78.63 nL/[cm.sup.2]). The PR values continuously declined with the decrease of the tested concentrations. The repellent characteristics of the four compounds against the cigarette beetles were variable. At the dose of 78.63 nL/[cm.sup.2], all the four compounds showed definite repellent activities against cigarette beetles, although their individual efficiency of repellency was not as good as that of the essential oil treatment. The PR values of [beta]-bisabolene, 1,4-dimethoxy-2-tertbutylbenzene, bornyl acetate, and (2E, 4E)-2,4-nonadienal were 90%, 62%, 74%, and 56%, respectively, after 2h of exposure. However, the repellent characteristics of the four compounds were obviously different at lower concentrations. The experimental data were further analyzed by Tukey' test, and the statistical results (see Table 3) could be used to exam the repellency level of each sample. Testing results of 0.13 nL/[cm.sup.2] showed that [beta]-bisabolene and (2E, 4E)-2,4-nonadienal possessed a higher level of repellency than DEET (P = 0.019 and 0.009, resp.) after 2h of exposure. The repellency of 1,4-dimethoxy-2-tert-butylbenzene was comparable to DEET (P = 0.966), while the bornyl acetate showed an insect attractant property.
As the results show in Table 4, the B. bicaule essential oil showed relatively weak repellency against booklice; the highest repellent rate of the essential oil was only 56% relative to DEET (PR = 98%) at the dose of 12.63 nL/[cm.sup.2] after 2 h of exposure. However, some of individual compounds showed certain repellent activities. At low concentration (0.10 nL/[cm.sup.2]), the repellency of the four compounds was at the same level as that of DEET (P = 0.952, 0.855, 1.000, and 1.000, resp.) after 2 h of exposure. At the highest concentration (63.17 nL/[cm.sup.2]), only [beta]-bisabolene showed an obvious repellent activity with PR value of 76% after 2 h of exposure.
The experimental results and data analysis showed that the repellent rates of the essential oil were almost comparable to those of the positive control at all testing concentrations against cigarette beetles. Each of the four compounds exhibited a different level of the repellent activity against cigarette beetles. Accordingly, it could be considered that these compounds would make various degrees of contribution to the strong repellency of the essential oil. Among them, [beta]-bisabolene (a sesquiterpene) might be the most important one which majorly affected the repellent activity against cigarette beetles. It has been reported that the sesquiterpenes showed repellent activities against several insects. In Khani and Heydarian's work, the essential oil of Teucrium polium subsp. capitatum (L.), which was rich in sesquiterpene, showed 60% and 52% repellency against Teucrium castaneum and Callosobruchus maculatus adults [35]. Based on the above findings, it was believed that the essential oil of B. bicaule and the types of sesquiterpenes compounds would be the exploration direction of natural repellents.
4. Conclusions
In this work, the chemical composition of B. bicaule essential oil was determined, and its contact and repellent activities against two stored product insects were investigated along with four individual components. A compound (2E, 4E)-2,4-nonadienal with striking contact toxicity was found, and the essential oil showed considerable contact and repellent activities, which could be attributed to the existence of different chemical compounds in essential oil. Some of those components might be the material basis of active effect. This work would provide scientific basis for further development and utilization of B. bicaule in stored product insects control. There must be a certain relationship between the bioactivity and structure of the compounds, which deserves further study and discussion.
https://doi.org/10.1155/2018/5830864
Conflicts of Interest
The authors declare that there are no conflicts of interest.
Acknowledgments
This project was supported by the National Natural Science Foundation of China (no. 81274025).
References
[1] T. Bhumi, C. Urvi, and P Pragna, "Biopesticidal potential of some plant derived essential oils against the stored grain pests," International Journal of Zoological Investigations, vol. 3, pp. 188-197, 2017.
[2] S.-S. Guo, W.-J. Zhang, C.-X. You et al., "Chemical composition of essential oil extracted from Laggera pterodonta and its bioactivities against two stored product insects," Journal of Food Processing and Preservation, vol. 41, no. 2, Article ID e12941,2017
[3] M. Hori, "Repellency of hinokitiol against the cigarette beetle, Lasioderma serricorne (Fabricius) (Coleoptera: Anobiidae)," Applied Entomology and Zoology, vol. 39, no. 3, pp. 521-526, 2004.
[4] B. D. Turner, "Liposcelis bostrychophila (psocoptera: Liposcelididae), a stored food pest in the UK," International Journal of Pest Management, vol. 40, no. 2, pp. 179-190, 1994.
[5] W.-J. Zhang, Z. Zhang, Z.-Y. Chen et al., "Chemical composition of essential oils from six Zanthoxylum species and their repellent activities against two stored-product insects," Journal of Chemistry, vol. 2017, Article ID 1287362, 2017.
[6] M. Lal, B. Ram, and P Tiwari, "Botanicals to Cope Stored Grain Insect Pests: A Review," International Journal of Current Microbiology and Applied Sciences, vol. 6, no. 6, pp. 1583-1594, 2017
[7] Q.-X. Han and J.-L. Chen, "Progress in antagonistic storage of Chinese traditional medicinal materials," Journal of Zhongkai Agrotechnical College, vol. 14, no. 3, pp. 59-63, 2001.
[8] Y.-L. Chang, L. Li, and Q.-N. Wu, "Study on storage and conservation technique of Rhizoma Alismatis," Research and Practice of Chinese Medicines, vol. 24, no. 4, pp. 70-73, 2010.
[9] H. R. El-Seedi, N. S. Khalil, M. Azeem et al., "Chemical composition and repellency of essential oils from four medicinal plants against Ixodes ricinus Nymphs (Acari: Ixodidae)," Journal of Medical Entomology, vol. 49, no. 5, pp. 1067-1075, 2012.
[10] M. Maedeh, I. Hamzeh, D. Hossein, A. Majid, and R. K. Reza, "Bioactivity of essential oil from Zingiber officinale (Zingiberaceae) against three stored-product insect species," Journal of Essential Oil Bearing Plants, vol. 15, no. 1, pp. 122-133, 2012.
[11] J.-Y. Liang, W.-T. Wang, Y.-F. Zheng et al., "Bioactivities and chemical constituents of essential oil extracted from Artemisia anethoides against two stored product insects," Journal of Oleo Science, vol. 66, no. 1, pp. 71-76, 2017
[12] J. Q. Mao, Y. Zhang, J. Gu, X. Zhang, and L. Ma, "Comparative study on antipyretic effect of naphtha in Bupleurum chinense," Chinese Journal of Hospital Pharmacy, vol. 27, pp. 156-159,2007
[13] J. Zhu, C. Luo, P. Wang, Q. He, J. Zhou, and H. Peng, "Saikosaponin A mediates the inflammatory response by inhibiting the MAPK and NF-[kappa]B pathways in LPS-stimulated RAW 264.7 cells," Experimental and Therapeutic Medicine, vol. 5, no. 5, pp. 1345-1350, 2013.
[14] H. Zhao, S. Li, and H. Zhang, "Saikosaponin a protects against experimental sepsis via inhibition of NOD2-mediated NF-[kappa]B activation," Experimental and Therapeutic Medicine, vol. 10, no. 2, pp. 823-827, 2015.
[15] T. Konno, K. Ninomiya, M. Yoshikawa, H. Matsuda, and T. Morikawa, "Triterpene saponin constituents from roots of Bupleurum falcatum: Hepatoprotective effects on D-galactosamine-induced cell damage," Planta Medica, vol. 81, no. S 01, pp. S1-S381, 2016.
[16] M. Sarwar and M. Salman, "Toxicity of oils formulation as a new useful tool in crop protection for insect pests control," International Journal of Chemical and Biomolecular Science, vol. 1, no. 4, pp. 297-302, 2015.
[17] K. Izakmehri, M. Saber, A. Mehrvar, M. B. Hassanpouraghdam, and S. Vojoudi, "Lethal and sublethal effects of essential oils from Eucalyptus camaldulensis and Heracleum persicum against the adults of Callosobruchus maculatus," Journal of Insect Science, vol. 13, article no. 152, 2013.
[18] I.-K. Park, K.-S. Choi, D.-H. Kim et al., "Fumigant activity of plant essential oils and components from horseradish (Armoracia rusticana), anise (Pimpinella anisum) and garlic (Allium sativum) oils against Lycoriella ingenua (Diptera: Sciaridae)," Pest Management Science, vol. 62, no. 8, pp. 723-728, 2006.
[19] D. H. Kim and Y. J. Ahn, "Contact and fumigant activities of constituents of Foeniculum vulgare fruit against three coleopteran stored-product insects," Pest Management Science, vol. 57, no. 3, pp. 301-306, 2001.
[20] J. A. Gonzalez, A. Estevezbraun, R. Estevezreyes et al., "Biological activity of secondary metabolites from Bupleurum salicifolium (Umbelliferae)," Experientia, vol. 51, no. 1, pp. 35-39, 1995.
[21] X.-Q. Li, Z.-G. He, K.-S. Bi, Z.-H. Song, and L. Xu, "Essential oil analyses of the root oils of 10 Bupleurum species from China," Journal ofEssential Oil Research, vol. 19, no. 3, pp. 234-238,2007
[22] National Pharmacopoeia Committee, Pharmacopoeia of Peoples Republic of China, China Medical Science and Technology Press, Beijing, China, 2015.
[23] Z. L. Liu and S. H. Ho, "Bioactivity of the essential oil extracted from Evodia rutaecarpa Hook f. et Thomas against the grain storage insects, Sitophilus zeamais Motsch. and Tribolium castaneum (Herbst)," Journal of Stored Products Research, vol. 35, no. 4, pp. 317-328, 1999.
[24] M. Sakuma, "Probit analysis of preference data," Applied Entomology and Zoology, vol. 33, no. 3, pp. 339-347, 1998.
[25] H.-Y. Zhou, N.-N. Zhao, S.-S. Du et al., "Insecticidal activity of the essential oil of Lonicera japonica flower buds and its main constituent compounds against two grain storage insects," Journal of Medicinal Plants Research, vol. 6, no. 5, 2012.
[26] K. Yang, C. F. Wang, C. X. You et al., "Bioactivity of essential oil of Litsea cubeba from China and its main compounds against two stored product insects," Journal of Asia-Pacific Entomology, vol. 17, no. 3, pp. 459-466, 2014.
[27] W. S. Abbott, "A method of computing the effectiveness of an insecticide," Journal of the American Mosquito Control Association, vol. 3, no. 2, pp. 302-303,1987
[28] J. S. Zhang, N. N. Zhao, Q. Z. Liu et al., "Repellent constituents of essential oil of Cymbopogon distans aerial parts against two stored-product insects," Journal of Agricultural and Food Chemistry, vol. 59, no. 18, pp. 9910-9915, 2011.
[29] F. Bakkali, S. Averbeck, D. Averbeck, and M. Idaomar, "Biological effects of essential oils--a review," Food and Chemical Toxicology, vol. 46, no. 2, pp. 446-475, 2008.
[30] C. X. You, K. Yang, Y. Wu et al., "Chemical composition and insecticidal activities of the essential oil of Perillafrutescens (L.) Britt. aerial parts against two stored product insects," European Food Research and Technology, vol. 239, pp. 481-490, 2014.
[31] S. Guo, W. Zhang, J. Liang et al., "Contact and repellent activities of the essential oil from Juniperusformosana against two stored product insects," Molecules, vol. 21, no. 4, article no. 504, 2016.
[32] C. X. You, H. Y. Jiang, W. J. Zhang et al., "Contact toxicity and repellency of the main components from the essential oil of Clausena anisum-olens against two stored product insects," Journal of Insect Science, vol. 15, no. 1, 2015.
[33] V. Caprioli, G. Cimino, R. Colle, M. Gavagnin, G. Sodano, and A. Spinella, "Insect antifeedant activity and hot taste for humans of selected natural and synthetic 1,4-dialdehydes," Journal of Natural Products, vol. 50, no. 2, pp. 146-151,1987
[34] C.-X. You, Y. Wang, W.-J. Zhang et al., "Chemical constituents and biological activities of the Purple Perilla essential oil against Lasioderma serricorne," Industrial Crops and Products, vol. 61, pp. 331-337, 2014.
[35] A. Khani and M. Heydarian, "Fumigant and repellent properties of sesquiterpene-rich essential oil from Teucrium polium subsp. capitatum (L.)," Asian Pacific Journal of Tropical Medicine, vol. 7, no. 12, pp. 956-961, 2014.
Xiao-Meng Wei, (1) Shan-Shan Guo, (2) Hua Yan, (3) Xian-Long Cheng (iD), (3) Feng Wei (iD), (1,3) and Shu-Shan Du (iD) (2)
(1) Faculty of Traditional Chinese Medicine, Beijing University of Chinese Medicine, Beijing 102488, China
(2) Beijing Key Laboratory of Traditional Chinese Medicine Protection and Utilization, Faculty of Geographical Science, Beijing Normal University, Beijing 100875, China
(3) National Institutes for Food and Drug Control, China Food and Drug Administration, Beijing 100050, China
Correspondence should be addressed to Feng Wei; weifeng@nifdc.org.cn and Shu-Shan Du; dushushan@bnu.edu.cn
Received 11 December 2017; Revised 2 February 2018; Accepted 27 February 2018; Published 16 April 2018
Academic Editor: Jose A. Pereira
Caption: Figure 2: Molecular structures of selected compounds from the essential oil of Bupleurum bicaule.
Table 1: Chemical composition of the essential oil of Bupleurum
bicaule.
Relative
Compounds content (%) (a) [RI.sub.exp]
Aldehydes
(2E,4E)-2,4-Octadienal 0.8 1113
(2E,4E)-2,4-Nonadienal 1.2 1214
(2E,4E)-2,4-Decadienal 2.8 1317
Monoterpenes
Bornyl acetate 1.1 1280
Trans-2-isopropylbicyclo 25.9 1765
[4.3.0] non-3-en-8-one
Sesquiterpenes
[alpha]-Longipinene 0.5 1352
[beta]-Elemene 0.8 1391
[beta]-Cuvebene 1.5 1390
1,4,7,-Cycloundecatriene, 1.9 1456
1,5,9,9-tetramethyl-,
Z,Z,Z-
Calarene 2.1 1467
[gamma]-Gurjunene 2.0 1479
(E,E)-[alpha]-Farnesene 0.4 1505
[beta]-Bisabolene 2.7 1510
Cuparene 2.9 1502
(E)-Nerolidol 0.5 1565
Spathulenol 0.9 1582
Caryophyllene oxide 1.4 1583
Humulene oxide II 1.4 1607
[alpha]-Cadinol 1.4 1653
[tau]-Muurolol 0.6 1662
Juniper camphor 0.3 1690
Alkynes
(6Z)-6-Tridecen-4-yne 2.7 1470
Aromatic compounds
1,4-Dimethoxy-2-tert- 4.3 1477
butylbenzene
Myristicin 1.6 1529
2(1H)Naphthalenone,3,5,6, 0.3 1772
7,8,8a-hexahydro-4,8a-
dimethyl-6-(1-methyl-
ethenyl)-
Others
4,5-Dimethyl-1,2,3,6,7,8, 23.5 1357
8a,8b-octahydrobiphenylene
Total 85.5
Compounds (b) [RI.sub.lit]
Aldehydes
(2E,4E)-2,4-Octadienal 1109
(2E,4E)-2,4-Nonadienal 1217
(2E,4E)-2,4-Decadienal 1316
Monoterpenes
Bornyl acetate 1281
Trans-2-isopropylbicyclo 1765
[4.3.0] non-3-en-8-one
Sesquiterpenes
[alpha]-Longipinene 1351
[beta]-Elemene 1393
[beta]-Cuvebene 1388
1,4,7,-Cycloundecatriene, 1454
1,5,9,9-tetramethyl-,
Z,Z,Z-
Calarene 1463
[gamma]-Gurjunene 1472
(E,E)-[alpha]-Farnesene 1505
[beta]-Bisabolene 1511
Cuparene 1499
(E)-Nerolidol 1564
Spathulenol 1578
Caryophyllene oxide 1580
Humulene oxide II 1611
[alpha]-Cadinol 1654
[tau]-Muurolol 1660
Juniper camphor 1693
Alkynes
(6Z)-6-Tridecen-4-yne 1470
Aromatic compounds
1,4-Dimethoxy-2-tert- 1477
butylbenzene
Myristicin 1523
2(1H)Naphthalenone,3,5,6, 1773
7,8,8a-hexahydro-4,8a-
dimethyl-6-(1-methyl-
ethenyl)-
Others
4,5-Dimethyl-1,2,3,6,7,8, 1357
8a,8b-octahydrobiphenylene
Total
Identification
Compounds methods (c)
Aldehydes
(2E,4E)-2,4-Octadienal MS; RI
(2E,4E)-2,4-Nonadienal MS; RI
(2E,4E)-2,4-Decadienal MS; RI
Monoterpenes
Bornyl acetate MS; RI
Trans-2-isopropylbicyclo MS; RI
[4.3.0] non-3-en-8-one
Sesquiterpenes
[alpha]-Longipinene MS; RI
[beta]-Elemene MS; RI
[beta]-Cuvebene MS; RI
1,4,7,-Cycloundecatriene, MS; RI
1,5,9,9-tetramethyl-,
Z,Z,Z-
Calarene MS; RI
[gamma]-Gurjunene MS; RI
(E,E)-[alpha]-Farnesene MS; RI
[beta]-Bisabolene MS; RI
Cuparene MS; RI
(E)-Nerolidol MS; RI
Spathulenol MS; RI
Caryophyllene oxide MS; RI
Humulene oxide II MS; RI
[alpha]-Cadinol MS; RI
[tau]-Muurolol MS; RI
Juniper camphor MS; RI
Alkynes
(6Z)-6-Tridecen-4-yne MS; RI
Aromatic compounds
1,4-Dimethoxy-2-tert- MS; RI
butylbenzene
Myristicin MS; RI
2(1H)Naphthalenone,3,5,6, MS; RI
7,8,8a-hexahydro-4,8a-
dimethyl-6-(1-methyl-
ethenyl)-
Others
4,5-Dimethyl-1,2,3,6,7,8, MS; RI
8a,8b-octahydrobiphenylene
Total
(a) Retention index (RI) in this experiment relative to the
homologous series of n-alkanes ([C.sub.5]-[C.sub.36]) on the HP-5
MS capillary column. (b) RI in literature. (c) Mass spectrum.
Table 2: Contact toxicity of Bupleurum bicaule essential oil and
its constituents against Lasioderma serricorne (LS) and Liposcelis
bostrychophila (LB) adults.
Insects Treatments Concentrations
(%)
LS Essential oil 1.91-10.00
[beta]-Bisabolene 2.97-15.00
1,4-Dimethoxy-2-tert- 1.97-10.00
butylbenzene
Bornyl acetate 0.90-4.40
(2E,4E)-2,4-Nonadienal 0.27-1.30
Pyrethrins (a) --
LB Essential oil 0-5.00
[beta]-Bisabolene 0-50.00
1,4-Dimethoxy-2-tert- 0.12-1.00
butylbenzene
Bornyl acetate 0.20-0.40
(2E,4E)-2,4-Nonadienal 0.20-0.40
Pyrethrins (a) --
[LD.sub.50]
Insects Treatments ([micro]g/adult)/
([micro]g/[cm.sup.2])
LS Essential oil 11.91
[beta]-Bisabolene 24.99
1,4-Dimethoxy-2-tert- 23.56
butylbenzene
Bornyl acetate 9.42
(2E,4E)-2,4-Nonadienal 2.31
Pyrethrins (a) 0.24
LB Essential oil --
[beta]-Bisabolene --
1,4-Dimethoxy-2-tert- 62.34
butylbenzene
Bornyl acetate 36.67
(2E,4E)-2,4-Nonadienal 32.23
Pyrethrins (a) 18.72
95% FL
Insects Treatments ([micro]g/adult)/
([micro]g/[cm.sup.2])
LS Essential oil 7.04-15.66
[beta]-Bisabolene 21.68-29.14
1,4-Dimethoxy-2-tert- 20.03-27.24
butylbenzene
Bornyl acetate 8.14-10.87
(2E,4E)-2,4-Nonadienal 2.03-2.61
Pyrethrins (a) 0.22-0.30
LB Essential oil --
[beta]-Bisabolene --
1,4-Dimethoxy-2-tert- 55.97-69.66
butylbenzene
Bornyl acetate 34.67-38.55
(2E,4E)-2,4-Nonadienal 30.59-33.97
Pyrethrins (a) 17.60-19.92
Insects Treatments Slope [+ or -] SE
LS Essential oil 2.01 [+ or -] 0.39
[beta]-Bisabolene 3.86 [+ or -] 0.56
1,4-Dimethoxy-2-tert- 3.18 [+ or -] 0.55
butylbenzene
Bornyl acetate 0.98 [+ or -] 0.17
(2E,4E)-2,4-Nonadienal 4.00 [+ or -] 0.62
Pyrethrins (a) 3.34 [+ or -] 0.32
LB Essential oil --
[beta]-Bisabolene --
1,4-Dimethoxy-2-tert- 6.42 [+ or -] 0.87
butylbenzene
Bornyl acetate 16.73 [+ or -] 2.28
(2E,4E)-2,4-Nonadienal 17.08 [+ or -] 2.31
Pyrethrins (a) 2.98 [+ or -] 0.40
Insects Treatments Chi square
([chi square])
LS Essential oil 17.50
[beta]-Bisabolene 3.61
1,4-Dimethoxy-2-tert- 2.90
butylbenzene
Bornyl acetate 7.53
(2E,4E)-2,4-Nonadienal 9.44
Pyrethrins (a) 13.11
LB Essential oil --
[beta]-Bisabolene --
1,4-Dimethoxy-2-tert- 3.93
butylbenzene
Bornyl acetate 7.04
(2E,4E)-2,4-Nonadienal 9.66
Pyrethrins (a) 10.56
(a) Data from Yang et al. [26].
Table 3: Percent repellency (PR) of the essential oil from
Bupleurum bicaule and its constituents against Lasioderma
serricorne adults at 2h and 4h after exposure. * Comparison of
different samples at the same concentration, df = 5.
Concentrations
Times Treatments (nL/[cm.sup.2])
78.63
2 h Essential oil 100 [+ or -] 0 (c)
[beta]-Bisabolene 90 [+ or -] 6 (bc)
1,4-Dimethoxy-2-tert- 62 [+ or -] 11 (a)
butylbenzene
Bornyl acetate 74 [+ or -] 12 (ab)
(2E,4E)-2,4-Nonadienal 56 [+ or -] 12 (a)
DEET 88 [+ or -] 7 (b)
F 15.878
P 0
4 h Essential oil 100 [+ or -] 0 (c)
[beta]-Bisabolene 88 [+ or -] 12 (bc)
1,4-Dimethoxy-2-tert- 46 [+ or -] 20 (a)
butylbenzene
Bornyl acetate 68 [+ or -] 13 (ab)
(2E,4E)-2,4-Nonadienal 50 [+ or -] 19 (a)
DEET 98 [+ or -] 2 (c)
F 15.428
P 0
Concentrations
Times Treatments (nL/[cm.sup.2])
15.73
2 h Essential oil 74 [+ or -] 12 (c)
[beta]-Bisabolene 12 [+ or -] 9 (b)
1,4-Dimethoxy-2-tert- 40 [+ or -] 13 (bc)
butylbenzene
Bornyl acetate -28 [+ or -] 19 (a)
(2E,4E)-2,4-Nonadienal 66 [+ or -] 20 (c)
DEET 76 [+ or -] 14
F 20.895
P 0
4 h Essential oil 62 [+ or -] 15 (bcd)
[beta]-Bisabolene 26 [+ or -] 17 (b)
1,4-Dimethoxy-2-tert- 32 [+ or -] 9 (bc)
butylbenzene
Bornyl acetate -4 [+ or -] 12 (a)
(2E,4E)-2,4-Nonadienal 72 [+ or -] 9 (cd)
DEET 78 [+ or -] 9 (d)
F 17.091
P 0
Concentrations
Times Treatments (nL/[cm.sup.2])
3.15
2 h Essential oil 70 [+ or -] 12 (c)
[beta]-Bisabolene 34 [+ or -] 15 (bc)
1,4-Dimethoxy-2-tert- 34 [+ or -] 15 (bc)
butylbenzene
Bornyl acetate -4 [+ or -] 17 (a)
(2E,4E)-2,4-Nonadienal 4 [+ or -] 19 (ab)
DEET 28 [+ or -] 7 (bc)
F 9.823
P 0
4 h Essential oil 24 [+ or -] 19 (ab)
[beta]-Bisabolene 24 [+ or -] 11 (ab)
1,4-Dimethoxy-2-tert- 34 [+ or -] 17 (ab)
butylbenzene
Bornyl acetate 14 [+ or -] 12 (ab)
(2E,4E)-2,4-Nonadienal 12 [+ or -] 18 (a)
DEET 58 [+ or -] 16 (b)
F 2.713
P 0.044
Concentrations
Times Treatments (nL/[cm.sup.2])
0.63
2 h Essential oil 66 [+ or -] 11 (b)
[beta]-Bisabolene 10 [+ or -] 16 (a)
1,4-Dimethoxy-2-tert- 6 [+ or -] 12 (a)
butylbenzene
Bornyl acetate -4 [+ or -] 9 (a)
(2E,4E)-2,4-Nonadienal 16 [+ or -] 17 (ab)
DEET 20 [+ or -] 14 (ab)
F 5.244
P 0.002
4 h Essential oil 28 [+ or -] 19 (bc)
[beta]-Bisabolene 14 [+ or -] 17 (abc)
1,4-Dimethoxy-2-tert- -4 [+ or -] 16 (ab)
butylbenzene
Bornyl acetate -8 [+ or -] 18 (ab)
(2E,4E)-2,4-Nonadienal -14 [+ or -] 16 (a)
DEET 56 [+ or -] 14 (c)
F 5.753
P 0.001
Concentrations
Times Treatments (nL/[cm.sup.2])
0.13
2 h Essential oil 38 [+ or -] 4 (bc)
[beta]-Bisabolene 56 [+ or -] 12 (c)
1,4-Dimethoxy-2-tert- 14 [+ or -] 12 (b)
butylbenzene
Bornyl acetate -36 [+ or -] 17 (a)
(2E,4E)-2,4-Nonadienal 60 [+ or -] 10 (c)
DEET 16 [+ or -] 7 (b)
F 39.261
P 0
4 h Essential oil 12 [+ or -] 18 (b)
[beta]-Bisabolene 34 [+ or -] 18 (bc)
1,4-Dimethoxy-2-tert- 28 [+ or -] 4 (bc)
butylbenzene
Bornyl acetate -18 [+ or -] 11 (a)
(2E,4E)-2,4-Nonadienal 32 [+ or -] 19 (bc)
DEET 46 [+ or -] 7 (c)
F 13.079
P 0
* Different letters in the same column (2 h and 4 h, resp.) mean
significant differences (P < 0.05) in ANOVA and Tukey's tests.
PR was subjected to an arcsine square-root transformation before
analysis.
Table 4: Percent repellency (PR) of the essential oil from
Bupleurum bicaule and its constituents against Liposcelis
bostrychophila adults at 2 h and 4 h after exposure. * Comparison of
different samples at the same concentration, df = 5.
Concentrations
Times Treatments (nL/[cm.sup.2])
63.17
2 h Essential oil 50 [+ or -] 12 (ab)
[beta]-Bisabolene 76 [+ or -] 15 (bc)
1,4-Dimethoxy-2-tert- 52 [+ or -] 19 (ab)
butylbenzene
Bornyl acetate 12 [+ or -] 14 (a)
(2E,4E)-2,4-Nonadienal 18 [+ or -] 20 (a)
DEET 100 [+ or -] 0 (c)
F 8.980
P 0
4 h Essential oil 44 [+ or -] 13 (abc)
[beta]-Bisabolene 74 [+ or -] 22 (bc)
1,4-Dimethoxy-2-tert- 20 [+ or -] 15 (ab)
butylbenzene
Bornyl acetate 10 [+ or -] 19 (a)
(2E,4E)-2,4-Nonadienal 28 [+ or -] 8 (ab)
DEET 96 [+ or -] 3 (c)
F 7.308
P 0
Concentrations
Times Treatments (nL/[cm.sup.2])
12.63
2 h Essential oil 56 [+ or -] 12 (bc)
[beta]-Bisabolene 74 [+ or -] 15 (cd)
1,4-Dimethoxy-2-tert- 8 [+ or -] 19 (a)
butylbenzene
Bornyl acetate 20 [+ or -] 10 (ab)
(2E,4E)-2,4-Nonadienal 74 [+ or -] 8 (cd)
DEET 98 [+ or -] 2 (d)
F 12.170
P 0
4 h Essential oil 48 [+ or -] 15 (a)
[beta]-Bisabolene 64 [+ or -] 20 (a)
1,4-Dimethoxy-2-tert- 28 [+ or -] 20 (a)
butylbenzene
Bornyl acetate 24 [+ or -] 10 (a)
(2E,4E)-2,4-Nonadienal 36 [+ or -] 13 (a)
DEET 82 [+ or -] 5 (a)
F 2.695
P 0.045
Concentrations
Times Treatments (nL/[cm.sup.2])
2.53
2 h Essential oil 4 [+ or -] 17 (a)
[beta]-Bisabolene 42 [+ or -] 19 (ab)
1,4-Dimethoxy-2-tert- 36 [+ or -] 13 (ab)
butylbenzene
Bornyl acetate 32 [+ or -] 9 (ab)
(2E,4E)-2,4-Nonadienal 24 [+ or -] 18 (a)
DEET 78 [+ or -] 10 (b)
F 5.299
P 0.002
4 h Essential oil 16 [+ or -] 10 (b)
[beta]-Bisabolene -16 [+ or -] 15 (a)
1,4-Dimethoxy-2-tert- 18 [+ or -] 16 (b)
butylbenzene
Bornyl acetate 38 [+ or -] 12 (bc)
(2E,4E)-2,4-Nonadienal 46 [+ or -] 7 (bc)
DEET 68 [+ or -] 3 (c)
F 10.321
P 0
Concentrations
Times Treatments (nL/[cm.sup.2])
0.51
2 h Essential oil 24 [+ or -] 19 (a)
[beta]-Bisabolene 12 [+ or -] 18 (a)
1,4-Dimethoxy-2-tert- 22 [+ or -] 18 (a)
butylbenzene
Bornyl acetate 10 [+ or -] 18 (a)
(2E,4E)-2,4-Nonadienal 20 [+ or -] 10 (a)
DEET 66 [+ or -] 8 (a)
F 1.998
P 0.115
4 h Essential oil 36 [+ or -] 10 (a)
[beta]-Bisabolene 48 [+ or -] 20 (a)
1,4-Dimethoxy-2-tert- 30 [+ or -] 14 (a)
butylbenzene
Bornyl acetate 22 [+ or -] 18 (a)
(2E,4E)-2,4-Nonadienal 14 [+ or -] 3 (a)
DEET 54 [+ or -] 6 (a)
F 2.014
P 0.113
Concentrations
Times Treatments (nL/[cm.sup.2])
0.10
2 h Essential oil -6 [+ or -] 20 (a)
[beta]-Bisabolene 18 [+ or -] 16 (a)
1,4-Dimethoxy-2-tert- 16 [+ or -] 13 (a)
butylbenzene
Bornyl acetate 34 [+ or -] 16 (a)
(2E,4E)-2,4-Nonadienal 28 [+ or -] 14 (a)
DEET 8 [+ or -] 3 (a)
F 2.173
P 0.091
4 h Essential oil -10 [+ or -] 16 (a)
[beta]-Bisabolene 16 [+ or -] 18 (ab)
1,4-Dimethoxy-2-tert- 18 [+ or -] 18 (ab)
butylbenzene
Bornyl acetate 44 [+ or -] 18
(2E,4E)-2,4-Nonadienal 8 [+ or -] 20 (ab)
DEET 22 [+ or -] 5 (ab)
F 2.564
P 0.054
* Different letters in the same column (2 h and 4 h, resp.) mean
significant differences (P < 0.05) in ANOVA and Tukey's tests. PR
was subjected to an arcsine square-root transformation before
analysis.
Figure 1: Percentage of different types of compounds in essential
oils of this work and literature.
This work Literature
Monoterpenes 27.0% 0.8%
Alkynes 21.3% 5.4%
Aldehydes 4.8% 12.6%
Sesquiterpenes 2.7% 42.6%
Aromatic compounds 5.9% 1.0%
Total of the five types 61.7% 62.4%
Note: Table made from bar graph.
 Printer friendly
 Cite/link
 Email
 Feedback
| |
| Title Annotation: | Research Article |
|---|---|
| Author: | Wei, Xiao-Meng; Guo, Shan-Shan; Yan, Hua; Cheng, Xian-Long; Wei, Feng; Du, Shu-Shan |
| Publication: | Journal of Chemistry |
| Date: | Jan 1, 2018 |
| Words: | 6885 |
| Previous Article: | Synthesis, Spectral Characterization, and Thermal and Cytotoxicity Studies of Cr(III), Ru(III), Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) Complexes... |
| Next Article: | Transportation and Transformation of Arsenic Species at the Intertidal Sediment-Water Interface of Bohai Bay, China. |
| Topics: | |