Chemical Composition and Nematicidal Activity of Essential Oil of Agastache rugosa against Meloidogyne incognita
Abstract
:1. Introduction
2. Results and Discussion
2.1. Essential Oil Chemical Composition
RI * | Compound | Composition, % |
---|---|---|
Monoterpenoids | 14.22 | |
931 | α-Pinene | 0.52 |
984 | β-Pinene | 1.21 |
1029 | D-Limonene | 2.49 |
1057 | γ-Terpinene | 0.13 |
1188 | α-Terpineol | 0.34 |
1097 | Linalool | 1.77 |
1236 | Pulegone | 2.56 |
1288 | Cuminic alcohol | 1.38 |
1292 | Thymol | 3.62 |
Sesquiterpenoids | 13.34 | |
1313 | Elixene | 0.12 |
1317 | Carvacrol | 0.20 |
1350 | α-Cubebene | 0.13 |
1382 | iso-Ledene | 0.11 |
1385 | β-Bourbonene | 0.37 |
1393 | β-Elemen | 0.26 |
1420 | Caryophyllene | 2.38 |
1462 | cis-α-Farnesene | 0.17 |
1473 | γ-Muurolene | 0.41 |
1486 | Germacrene D | 1.45 |
1491 | Aromadendrene | 0.32 |
1499 | Bicyclogermacrene | 0.88 |
1500 | α-Muurolene | 0.29 |
1511 | α-Farnesene | 0.72 |
1454 | α-Caryophyllene | 0.19 |
1521 | δ-Cadinene | 0.85 |
1546 | Cadina-4,9-diene | 0.28 |
1561 | Germacrene B | 0.68 |
1578 | Spatulenol | 1.11 |
1584 | Caryophyllene oxide | 0.73 |
1592 | Viridiflorol | 0.12 |
1642 | τ-Muurolol | 0.81 |
1652 | α-Cadinol | 0.96 |
Phenylpropanoids | 66.60 | |
1195 | Estragole | 8.55 |
1356 | Eugenol | 7.54 |
1369 | Methyleugenol | 50.51 |
Others | 1.98 | |
975 | Morrilol | 0.16 |
1066 | Acetophenone | 1.82 |
Total identified | 96.14 |
2.2. Nematicidal Activity
Treatments | Concentrations (μg/mL) | LC50 (μg/mL) 95% FL * | LC90 (μg/mL) 95% FL * | Slope ± SE | Chi square (χ2 ) |
---|---|---|---|---|---|
A. rugosa | 12.5-200.0 | 47.3 (42.9–55.2) | 174.6 (156.9–191.1) | 6.51 ± 0.66 | 9.06 |
Estragole | 80.0-860.0 | 185.9 (169.7–206.1) | 463.6 (422.9–489.5) | 7.03 ± 0.68 | 7.64 |
Eugenol | 12.5-200.0 | 66.6 (60.6–74.1) | 182.3 (164.8–198.6) | 5.21 ± 0.53 | 9.77 |
Methyleugenol | 40.0-240.0 | 89.4 (79.7–98.1) | 193.7 (176.7–214.9) | 8.36 ± 0.78 | 8.25 |
Carbofuran ** | 25.0-400.0 | 72.3 (37.9–118.0) | - | - | 13.57 |
3. Experimental
3.1. Plant Material and Essential Oil Extraction
3.2. Gas Chromatography-Mass Spectrometry
3.3. Purification and Characterization of Three Constituent Compounds
3.4. Isolated Constituent Compounds
3.5. Nematicidal Assay
4. Conclusions
Acknowledgments
References
- Bai, C.Q.; Liu, Z.L.; Liu, Q.Z. Nematicidal constituents from the essential oil of Chenopodium ambrosioides aerial parts. E-J. Chem. 2011, 8, 143–148. [Google Scholar] [CrossRef]
- Wang, J.H.; Zhao, J.L.; Liu, H.; Zhou, L.; Liu, Z.L.; Han, J.G.; Zhu, Y.; Yang, F.Y. Chemical analysis and biological activity of the essential oils of two Valerianaceous species from China: Nardostachys chinensis and Valeriana. officinalis. Molecules 2010, 15, 6411–6422. [Google Scholar] [CrossRef]
- Wang, J.H.; Xu, L.; Yang, L.; Liu, Z.L.; Zhou, L. Composition, antibacterial and antioxidant activities of essential oils from Ligusticum sinense and L. jeholense (Umbelliferae) from China. Rec. Nat. Prod. 2011, 5, 314–318. [Google Scholar]
- Chu, S.S.; Hu, J.F.; Liu, Z.L. Composition of essential oil of Chinese Chenopodium ambrosioides and insecticidal activities to maize weevil, Sitophilus zeamais. Pest. Manag. Sci. 2011, 67, 714–718. [Google Scholar] [CrossRef]
- Chu, S.S.; Jiang, G.H.; Liu, Z.L. Insecticidal compounds from the essential oil of Chinese medicinal herb, Atractylodes chinensis. Pest. Manag. Sci. 2011, 67, 1253–1257. [Google Scholar] [CrossRef]
- Zhao, N.N.; Zhou, L.; Liu, Z.L.; Du, S.S.; Deng, Z.W. Evaluation of toxicities of some common spices essential oils from China against Liposcelis bostrychophila. Food Control. 2012, 26, 486–490. [Google Scholar] [CrossRef]
- Liu, Z.L.; He, Q.; Chu, S.S.; Wang, C.F.; Du, S.S.; Deng, Z.W. Essential oil composition and larvicidal activity of Saussurea lappa roots against the mosquito Aedes albopictus (Diptera: Culicidae). Parasitol. Res. 2012, 110, 2125–2130. [Google Scholar] [CrossRef]
- Liu, Z.L.; Liu, Q.Z.; Du, S.S.; Deng, Z.W. Mosquito larvicidal activity of alkaloids and limonoids derived from Evodia rutaecarpa unripe fruits against Aedes albopictus (Diptera: Culicidae). Parasitol. Res. 2012, 111, 991–996. [Google Scholar] [CrossRef]
- Liu, X.C.; Dong, H.W.; Zhou, L.; Du, S.S.; Liu, Z.L. Essential oil composition and larvicidal activity of Toddalia asiatica roots against the mosquito Aedes albopictus (Diptera: Culicidae). Parasitol. Res. 2013. [Google Scholar] [CrossRef]
- Sung, B.K.; Lee, H.S. Chemical composition and acaricidal activities of constituents derived from Eugenia caryophyllata leaf oils. Food Sci. Biotechnol. 2005, 14, P73–P76. [Google Scholar]
- Li, H.Q.; Bai, C.Q.; Chu, S.S.; Zhou, L.; Du, S.S.; Liu, Z.L.; Liu, Q.Z. Chemical composition and toxicities of the essential oil derived from Kadsura heteroclita stems against Sitophilus zeamais and Meloidogyne incognita. J. Med. Plants Res. 2011, 5, 4943–4948. [Google Scholar]
- Liu, Q.Z.; Li, H.Q.; Liu, Z.L. Nematicidal constituents from the ethanol extract of Evodia rutaecarpa Hort unripe fruits. J. Chem. 2013. [Google Scholar] [CrossRef]
- Lahlou, M. Methods to study the phytochemistry and bioactivity of essential oils. Phytother. Res. 2004, 18, 435–448. [Google Scholar] [CrossRef]
- Ntalli, N.G.; Manconi, F.; Leonti, M.; Maxia, A.; Caboni, P. Aliphatic ketones from Ruta chalepensis (Rutaceae) induce paralysis on root knot nematodes. J. Agric. Food Chem. 2011, 59, 7098–7103. [Google Scholar] [CrossRef]
- Oka, Y.; Nacar, S.; Putievsky, E.; Ravid, U.; Yaniv, Z.; Spiegel, Y. Nematicidal activity of essential oils and their components against the root-knot nematode. Phytopathology 2000, 90, 710–715. [Google Scholar] [CrossRef]
- Al-Banna, L.; Darwish, R.M.; Aburjai, T. Effect of plant extracts and EOs on root-knot nematode. Phytopathol. Mediterr. 2003, 42, 123–128. [Google Scholar]
- Ntalli, N.G.; Caboni, P. Botanical nematicides: A review. J. Agric. Food Chem. 2012, 60, 9929–9940. [Google Scholar] [CrossRef]
- Andres, M.F.; Gonzalez-Coloma, A.; Sanz, J.; Burillo, J.; Sainz, P. Nematicidal activity of essential oils: A review. Phytochem. Rev. 2013. [Google Scholar] [CrossRef]
- Isman, M.B. Plant essential oils for pest and disease management. Crop. Prot. 2000, 19, 603–608. [Google Scholar] [CrossRef]
- Isman, M.B. Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Ann. Rev. Entomol. 2006, 51, 45–66. [Google Scholar] [CrossRef]
- Jinagsu New Medical College, Dictionary of Chinese Herbal Medicine; Shanghai Science & Technology Press: Shanghai, China, 1977; pp. 2710–2712.
- Charles, D.J.; Simon, J.E; Widrlechner, M.P. Characterization of the essential oil of Agastache species. J. Agric. Food Chem. 1991, 39, 1946–1949. [Google Scholar] [CrossRef]
- Weyerstahl, P.; Marschall, H.; Manteuffel, E. Volatile constituents of Agastache rugosa. J. Essent. Oil Res. 1992, 4, 585–587. [Google Scholar]
- Svoboda, K.P.; Gough, J.; Hampson, J.; Galambosi, B. Analysis of the essential oils of some Agastache. species grown in Scotland from various seed sources. Flav. Fragr. J. 1995, 10, 139–145. [Google Scholar] [CrossRef]
- Nguyen, X.D.; Luu, D.C.; Nguyen, H.T.; La, D.M.; Le, V.H.; Leclercq, P.A. Constituents of the leaf and flower oils of Agastache rugosa (Fisch. et Mey) O. Kuntze from Vietnam. J. Essent. Oil Res. 1996, 8, 135–138. [Google Scholar] [CrossRef]
- Song, J.H.; Kim, M.J.; Kwon, H.D.; Lee, W.K.; Park, I.H. Antimicrobial activity and characterization of volatile flavor extracts from Agastache rugosa. J. Food Sci. Nutr. 1999, 4, 97–102. [Google Scholar]
- Yang, D.; Wang, F.; Su, J.; Zeng, L. Chemical composition of essential oil in stems, leaves and flowers of Agastache rugosa. J. Chin. Med. Mater. 2000, 23, 149–151. [Google Scholar]
- Kim, T.H.; Shin, J.H.; Baek, H.H.; Lee, H.J. Volatile flavour compounds in suspension culture of Agastache rugosa Kuntze (Korean mint). J. Sci. Food Agric. 2001, 81, 569–575. [Google Scholar] [CrossRef]
- Shin, S.; Kim, Y.S.; Kang, C.A. Production of volatile oil components by cell culture of Agastache rugosa O. Kuntze. Nat. Prod. Sci. 2001, 7, 120–123. [Google Scholar]
- Shin, S.; Kang, C.A. Antifungal activity of the essential oil of Agastache rugosa Kuntze and its synergism with ketoconazole. Lett. Appl. Microbiol. 2003, 36, 111–115. [Google Scholar] [CrossRef]
- Shin, S. Essential oil compounds from Agastache rugosa as antifungal agents against Trichophyton species. Arch. Pharm. Res. 2004, 27, 295–299. [Google Scholar] [CrossRef]
- Chae, Y.A.; Hyun-Choong, O.; Song, J.S. Variability of the volatile composition of Agastache rugosa in South Korea. Acta. Hort. 2005, 675, 59–64. [Google Scholar]
- Kim, J. Phytotoxic and antimicrobial activities and chemical analysis of leaf essential oil from Agastache rugosa. J. Plant. Biol. 2008, 51, 276–283. [Google Scholar] [CrossRef]
- Skakovskii, E.D.; Kiselev, W.P.; Tychinskaya, L.Y; Schutova, A.G.; Gonsharova, L.W.; Spiridowish, E.W.; Bovdey, N.A.; Kiselev, P.A.; Gaidukevich, O.A. Characterization of the essential oil of Agastache rugosa by NMR spectroscopy. J. Appl. Spectrosc. 2010, 77, 329–334. [Google Scholar] [CrossRef]
- Jun, H.J.; Chung, M.J.; Dawson, K.; Rodriguez, R.L.; Houng, S.J.; Cho, S.Y.; Jeun, J.; Kim, J.Y.; Kim, K.H.; Park, K.W. Nutrigenomic analysis of hypolipidemic effects of Agastache rugosa essential oils in HepG2 cells and C57BL/6 mice. Food Sci. Biotechnol. 2010, 19, 219–227. [Google Scholar] [CrossRef]
- Mo, J.X.; Ma, L. Volatile oil of Herba agastache in various growth periods and different parts by GC-MS. Chin. J. Pharm. 2011, 42, 268–270. [Google Scholar]
- Kim, S.I.; Park, C.; Ohh, M.H.; Cho, H.C.; Ahn, Y.J. Contact and fumigant activities of aromatic plant extracts and essential oils against Lasioderma serricorne (Coleoptera: Anobiidae). J. Stored Prod. Res. 2003, 39, 11–19. [Google Scholar] [CrossRef]
- Kim, S.I.; Roh, J.Y.; Kim, D.H.; Lee, H.S.; Ahn, Y.J. Insecticidal activities of aromatic plant extracts and essential oils against Sitophilus oryzae and Callosobruchus chinensis. J. Stored Prod. Res. 2003, 39, 293–303. [Google Scholar] [CrossRef]
- Wilson, L.A.; Senechal, N.P.; Widrlechnerr, M.P. Headspace analysis of the volatile oils of Agsstache. J. Agric. Food Chem. 1992, 40, 1362–1366. [Google Scholar] [CrossRef]
- Yue, J.L.; Pan, X.F.; Wang, J.C. Chemical constituents of essential oil of Agastache rugosa of northeast China. J. Northeast Forestry Univ. 1998, 26, 72–74. [Google Scholar]
- Wang, D.M.; Yang, D.B.; Wang, F.S.; Wu, H.Y.; Gu, S.Y. Chemical constituent of Agastache. rugosa essential oils and physical forms of Agastache rugosa. Chin. Tradit. Herb. Drugs 2005, 36, 1302–1303. [Google Scholar]
- Mo, J.X.; Jiang, C.; Zhang, X.Y. Studies on characteristics of volatile oil and micro-identification between Herba Pogostamonis and Herba Agastachis Rugosae. J. Chin. Med. Mater. 2009, 32, 1675–1677. [Google Scholar]
- Fujita, S.; Fujita, Y. Miscellaneous contributions to essential oils of the plants from various territories. XXXIII. Essential oil of Agastache rugosa. Yakugaku Zasshi 1973, 93, 1679–1681. [Google Scholar]
- Park, I.K.; Kim, J.; Lee, S.G.; Shin, S.C. Nematicidal activity of plant essential oils and components from ajowan (Trachyspermum ammi), allspice (Pimenta dioica) and litsea (Litsea cubeba) essential oils against pine wood nematode (Bursaphelenchus xylophilus). J. Nematol. 2007, 39, 275–279. [Google Scholar]
- Ntalli, N.G.; Ferrari, F.; Giannakou, I.; Menkissoglu-Spiroudi, U. Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components. J. Agric. Food Chem. 2010, 58, 7856–7863. [Google Scholar] [CrossRef]
- Ntalli, N.G.; Ferrari, F.; Giannakou, I.; Menkissoglu-Spiroudi, U. Synergistic and antagonistic interactions of terpenes against Meloidogyne incognita and the nematicidal activity of essential oils from seven plants indigenous to Greece. Pest. Manag. Sci. 2011, 67, 341–351. [Google Scholar] [CrossRef]
- Abdel-Rahman, F.H.; Alaniz, N.M.; Saleh, M.A. Nematicidal activity of terpenoids. J. Environ. Sci. Health 2013, 48B, 16–22. [Google Scholar]
- Adams, R.P. Identification of Essential Oil Components by Gas Chromatography/Quadrupole. Mass Spectroscopy; Allured: Carol Stream, IL, USA, 2007. [Google Scholar]
- Mohottalage, S.; Tabacchi, R.; Guerin, P.M. Components from Sri Lankan Piper betel L. leaf oil and their analogues showing toxicity against the housefly, Musca domestica. Flav. Fragr. J. 2007, 22, 130–138. [Google Scholar] [CrossRef]
- Miyazawa, M.; Kohno, G. Suppression of chemical mutagen-induced SOS response by allylbenzen from Asiasarum heterotropoides in the Salmonella typhimurium TA1535/pSK1002 umu test. Nat. Prod. Res. 2005, 19, 29–36. [Google Scholar] [CrossRef]
- Sakuma, M. Probit analysis of preference data. Appl. Entomol. Zool. 1998, 33, 339–347. [Google Scholar]
- Sample Availability: Samples of the crude extracts and pure compounds are available from the authors.
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Li, H.Q.; Liu, Q.Z.; Liu, Z.L.; Du, S.S.; Deng, Z.W. Chemical Composition and Nematicidal Activity of Essential Oil of Agastache rugosa against Meloidogyne incognita. Molecules 2013, 18, 4170-4180. https://doi.org/10.3390/molecules18044170
Li HQ, Liu QZ, Liu ZL, Du SS, Deng ZW. Chemical Composition and Nematicidal Activity of Essential Oil of Agastache rugosa against Meloidogyne incognita. Molecules. 2013; 18(4):4170-4180. https://doi.org/10.3390/molecules18044170
Chicago/Turabian StyleLi, He Qin, Qi Zhi Liu, Zhi Long Liu, Shu Shan Du, and Zhi Wei Deng. 2013. "Chemical Composition and Nematicidal Activity of Essential Oil of Agastache rugosa against Meloidogyne incognita" Molecules 18, no. 4: 4170-4180. https://doi.org/10.3390/molecules18044170