Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Phytochemical Study of the Aerial Parts of Conyza discoridis Growing in Saudi Arabia

  • Published : 2009.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Phytochemical investigation of the aerial parts of Conyza discoridis (L.) Desf. resulted in the isolation of the new sesquiterpene dilactone ester vernomenin-6-(2-hydroxymethyl)-acrylate (4) and two known sesquiterpene dilactones vernolepin (1) and vernomenin (3). Two known flavonols, 3-O-methylquercetin (2) and transilin (3-O-methylquercetin 7-O-${\beta}$-D-glucopyranoside) (5), were also identified. The structures were determined utilizing physical, chemical and spectral methods.

Keywords

References

  1. Abdallah, O.M. and Ibraheim, Z.Z., Sesquiterpene lactones from Pluchea dioscoridis. Pharmazie 50, 277-278 (1995)
  2. Abegaz, B.M., Keige, A.W., Diaz, J.G. and Herz, W., Sesquiterpene lactones and other constituents of Vernonia species from Ethiopia. Phytochemistry 37, 191-196 (1994) https://doi.org/10.1016/0031-9422(94)85023-2
  3. Al-Yahya, M.A., Al-Meshal, I.A., Mossa, J.S., Al-Badr, A.A. and Tariq, M., Saudi Plants A phytochemical and biological approach. King Saud University Press, 1990, pp. 10-12
  4. Bauer, L, Simoes, C.M.O., De Siqueira, N.C.S., Schenkel, E.P., Silva, G.A.A.B. and Alice, C.B., Flavonoids of the inflorescences of Achyrocline alata. Revista Latinoamericana de Quimica 20, 68-69. (1989)
  5. Bohlmann, F., Metwally, M.A. and Jakupovic, J., Eudesmanolides from Pluchea dioscoridis. Phytochemistry 23, 1975-1977 (1984) https://doi.org/10.1016/S0031-9422(00)84953-5
  6. Bohlmann, F. and Zdero, C., New glaucolides from Vernonia species. Revista Latinoamericana de Quimica 19, 63-65 (1988)
  7. Chagonda, L., Lockey, P.M., Marples, B.A., Salt, W.G. and Traynor, J.R., Cytotoxic action of α-methylene lactones towards HeLa cells in culture. Phytothe. Res. 3,196-200 (1989) https://doi.org/10.1002/ptr.2650030509
  8. Chen, Y., Wu, Z. and Cheng, P., Antitumor activity and internal stress of partially conjugated five and/or six-member rings of natural terpenoids. Youji Huaxue 1, 21-28 (1987)
  9. Dawidar, A. and Metwally, M., Egyptian Compositae. V. New $\alpha$- cyclocostunolide and isocostic acid derivatives from Pluchea dioscoridis. Chem. Pharm. Bull. 33, 5068-5070 (1985) https://doi.org/10.1248/cpb.33.5068
  10. El-Shanawany, M.A.A., Plants used in Saudi Folk medicine. King Abdul- Aziz City for Science and Technology, Riyadh, 1996, p. 277
  11. Ghazanfar, S.A., Handbook of Arabian medicinal plants. CRC Press, Boca Raton, Ann Arbor, London, Tokyo, 1994, pp. 109-110
  12. Grace, M.H., Chemical composition and biological activity of the volatiles of Anthemis melampodina and Pluchea dioscoridis. Phytother. Res. 16(S1), 183-185 (2002) https://doi.org/10.1002/ptr.872
  13. Harborne, J.B., Mabry, T.J., and Mabry, H., The flavonoids. Academic press, New York San Francisco, 1975
  14. Imomnazarov, B. A. and Bandyukova, V.A., Polyphenols in Astragalus species of the flora of the Western pamirs. III. Khimiya Prirodnykh Soedinenii, 876-7 (1988)
  15. Iwashina, T., Ootani, S., and Hayashi, K., Neochilenin, a new glycoside of 3-O-methylquercetin, and other flavonols in the tepals of Neochilenia, Neoporteria and Parodia species (Cactaceae). Botanical Magazine, Tokyo 97, 23-30 (1984) https://doi.org/10.1007/BF02488144
  16. Jain, A.K. and Saxena, V.K., Isolation and characterization of 3-methoxyquercetin 7-O-$\beta$-D-glucopyranoside from Trifolium pretense. National Academy Science Letters (India) 9, 379- 380 (1986)
  17. Jakupovic, J., Baruah, R.N., Chau T.T.V., Bohlmann, F., Msonthi, J.D., and Schmeda-Hirschmann, G. New vernolepin derivatives from Vernonia glabra and glaucolides from Vernonia scorpioides. Planta Med. 378-380 (1985) https://doi.org/10.1055/s-2007-969524
  18. Jisaka, M., Ohigashi, H., Takegawa, K., Huffman, M.A., and Koshimizu, K., Antitumoral and antimicrobial activities of bitter sesquiterpene lactones of Vernonia amygdalina, a possible medicinal plant used by wild chimpanzees. Biosci. Biotechnol. Biochem. 57, 833-834 (1993) https://doi.org/10.1271/bbb.57.833
  19. Jurzysta, A., Flavonoids of leaves of some Nicotiana species. Pamietnik Pulawski 79, 231-237 (1983)
  20. Khafagy, S.M., Sabri, N.N., Abd El-Salam, N., and Seif El-Din, A., Flavonoidal contents of Carthamus glaucus Bieb-Emend, Hanelt spp. alexandrinus Hanelt (Compositae). Egyptian Journal of Pharmaceutical Sciences 19, 307-312 (1978)
  21. Klyshev, L.K. and Baltabaeva, G.R., Resources and biochemical characteristics of Artemisia cina Berg. Biologicheskaya 16, 7-9 (1978)
  22. Krenn, L., Miron, A., Pemp, E., Petr, U., and Kopp, B., Flavonoids from Achillea nobilis L. Zeitschrift fuer Naturforschung (C: Journal of Biosciences) 58, 11-16 (2003)
  23. Kupchan, S.M., Hemingway, R.J., Werner, D., and Karim, A., Tumor inhibitors. XLVI. Vernolepin, a novel sesquiterpene dilactone tumor inhibitor from Vernonia hymenolepis. J. Org. Chem. 34, 3903-3908 (1969) https://doi.org/10.1021/jo01264a034
  24. Kupchan, S.M., Hemingway, R.J., Werner, D., Karim, A., McPhail, A.T., and Sim, G. A., Tumor inhibitors. XXXI. Vernolepin, a novel elemanolide dilactone tumor inhibitor from Vernonia hymenolepis. J. Am. Chem. Soc. 90, 3596-3597 (1968) https://doi.org/10.1021/ja01015a073
  25. Laekeman, G.M., De Clerck, F., Vlietinck, A.J., and Herman, A.G., Vernolepin: an antiplatelet compound of natural origin. Naunyn- Schmiedeberg's Archives of Pharmacology 331,108-113 (1985) https://doi.org/10.1007/BF00498859
  26. Laekeman, G.M., Mertens, J., Totte, J., Bult, H., Vlietinck, A.J., and Herman, A.G., Isolation and pharmacological characterization of vernolepin. J. Nat. Prod. 46, 161-169 (1983) https://doi.org/10.1021/np50026a003
  27. Magboul, A.Z.I., Bashir, A.K., Khalid, S.A., and Farouk, A., Antimicrobial activity of vernolepin and vernodalin. Fitoterapia 68, 83-84 (1997)
  28. Mahmoud, A.A., 7-Epi-eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenes from Pluchea dioscoridis. Phytochemistry 45, 1633-1638 (1997). https://doi.org/10.1016/S0031-9422(97)00257-4
  29. Migahid, AM., Flora of Saudi Arabia, Riyadh University Publications, Riyadh,Vol. 1, 2th edition, 33, 1978
  30. Mossa, J.S., Al-Yahya, M.A., and Al-Meshal, I.A., Medicinal plants of Saudi Arabia. King Saud University Libraries Publications, Riyadh, 1987, pp. 30, 174
  31. Oksuz, S., Flavonoidal compounds of Inula viscosa. Part II. Planta Med. 31, 270-273 (1977) https://doi.org/10.1055/s-0028-1097528
  32. Omar, A.A., Sarg, T.M., Khafagy, S.M., Ibrahim, Y.E., Zdero, C., and Bohlmann, F., Naturally occurring terpene derivatives. Part 467. A eudesmanolide from Pluchea dioscoridis. Phytochemistry 22, 779-780 (1983) https://doi.org/10.1016/S0031-9422(00)86986-1
  33. Souleles, C. and Philianos, S., Chemical constituents of Inula graveolens Desf. Fitoterapia 50, 251-254 (1979)
  34. Toubiana, R., Mompon, B., Ho, C., and Toubiana, M.J., Isolation of vernodalin and vernolepin from Vernonia guineensis. Authenticity of the elemane skeleton. Phytochemistry 14, 775-778 (1975) https://doi.org/10.1016/0031-9422(75)83033-0