Isolation and structure determination of acetylated triterpenoid saponins from the seeds of Centratherum anthelminticum

Natural Product Research

Volumn 24, Issue 2, 2010, Pages 120-130

  Mehta, B K ^a   Mehta, Darshana ^a   Itoriya, Amrita ^a  

^a VIKRAM UNIVERSITY   (India)

Author keywords

Acetylated; Centratherum anthelminticum; Hederagenin; Saponin

Indexed keywords

3 O [BETA DEXTRO GLUCOPYRANOSYL (1-2) ALPHA LEVO RHAMNOPYRANOSYL (1-2) ALPHA LEVO ARABINOPYRANOSYL] 28 O [BETA DEXTR XYLOPYRANOSYL (1-4) ALPHA LEVO RHAMNOPYRANOSYL (1-3) BETA DEXTRO GLUCOPYRANOSYL] 23 HYDROXYOLEAN 12 EN 28 OIC ACID; 3 O [BETA DEXTRO GLUCOPYRANOSYL (1-2) ALPHA LEVO RHAMNOPYRANOSYL (1-2) ALPHA LEVO ARABINOPYRANOSYL] 28 O [BETA DEXTRO GLUCORANOSYL (1-3) BETA DEXTRO GLUCOPYRANOSYL] 23 HYDROXYOLEAN 12 EN 28 OIC ACID; ACETONE; CENTRATHERUM ANTHELMINTICUM EXTRACT; GLYCOSIDE; METHANOL; PLANT EXTRACT; SAPONIN; TRITERPENOID; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CENTRATHERUM ANTHELMINTICUM; CONTROLLED STUDY; DRUG ACETYLATION; DRUG ISOLATION; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; MEDICINAL PLANT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; PLANT SEED; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

ACETYLATION; ASTERACEAE; SAPONINS; SEEDS; TRITERPENES;

CENTRATHERUM ANTHELMINTICUM;

EID: 75349107285     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786410802405128     Document Type: Article

References (28)

1. Ahmad, V.U., & Atta-ur-Rahman, A.V. (1994). Handbook of natural products data: Pentacyclic triterpenoids (Vol. 2, pp. 1-512). Amsterdam/London/New York: Elsevier.
2. Ali, M. (2000). Techniques in terpenoid identification. Delhi: Birla Publication.
3. Anjaneyulu, A.S.R., Raju, K.V.S., Mallavadhani, U.V., & Prakash, C.V.S. (1993). Chemical examination of a sea cucumber Holothuria spinifera. Indian Journal of Chemistry, 32(B), 457-459.
4. Arnaldo Viana, F., Braz-Filho, R., Pouliquen, Y.B.M., Neto, M.A., Santiago, G.M.P., & Filho, E.R. (2004). Triterpenoid saponins from stem bark of Pentaclethra macroloba. Journal of Brazilian Chemical Society, 15(4), 595-602.
5. Bauer, A.W., Kirby, W.M.M., Sherris, J.C., & Turck, M. (1966). Antibiotic susceptibility testing by a standardized single disk method. American Journal of Clinical Pathology, 45, 493-496.
6. Bellamy, J.J. (1925). The infrared spectra of complex molecules. London: Chapman & Hall.
7. De Bruyn, A., & Anteunis, M. (1976). Conformation of the C-5/C-6 fragment of aldohexopyranoses. Carbohydrate Research, 47, 311-314.
8. Dey, A.C. (1980). Indian medicinal plants used in ayurvedic preparations (pp. 9-10). Dehradun: B. Singh, & M.P. Singh.
9. Elbandy, M., Miyamoto, T., Chauffert, B., Delaude, C., & Lacaille-Dubois, M.A. (2002). Novel acylated triterpene glycosides from Muraltia heisteria. Journal of Natural Products, 65, 193-197.
10. Finar, L. (1989). Organic chemistry (5th ed., Vol. 2, pp. 517-605). Singapore: Longman, ELBS.
11. Gohar, A.A., Maatooq, G.T., Niwa, M., & Yoshiaki, T. (2002). A new triterpene saponin from Chenopodium ficifolium. Zeitschrift Fur Naturforschung, 57c, 597-602.
12. Khalik, S.M.A., Miyase, T., El-Ashaal, H.A., & Melek, F.R. (2000). Triterpenoid saponins from Fagonia cretica. Phytochemistry, 54, 853-859.
13. Kirtikar, K.R., & Basu, B.D. (1984). Indian medicinal plants (Vol. II, pp. 1326-1327). Dehradun: B. Singh, & M.P. Singh.
14. Maeda, C., Ohtani, K., Kasai, R., Yomasaki, K., Nguyen, M.D., Nguyen, T.N., et al. (1994). Oleanane and ursane glycosides from Schefflera octophylla. Phytochemistry, 37(4), 1131-1137.
15. Mahato, S.B., & Kundu, A.P. (1994). 13C NMR spectra of pentacyclic triterpenoids - a compilation and some salient features. Phytochemistry, 37, 1517-1575.
16. Massicot, G., Lavaud, C., Guillaume, D., Le Men-Oliver, L., & Van Binst, G. (1986). Identification and sequencing of sugars in saponins using 2D-1H NMR spectroscopy. Journal of the Chemical Society - Chemical Communications, 19, 1485-1487.
17. Massiot, G., Lavaud, C., Le Men-Olivier, L., van Binst, G., Miller, S.P.F., & Fales, H.M (1988). Structural elucidation of alfalfa root saponins by mass spectrometry and nuclear magnetic resonance analysis. Journal of the Chemical Society - Perkin Transactions, 1, 3071-3079.
18. Mehta, B.K., Mehta, D., & Itoria, A. (2004a). Structure elucidation by NMR spectroscopy of a new acetylated saponin from Centratherum anthelminticum. Carbohydrate Research, 339, 2871-2874.
19. Mehta, B.K., Verma, M., Kotra, S., & Jafari, M. (2004b). Lipid constituents from Centratherum anthelminticum (seeds). Indian Journal of Chemistry, 43(B), 442-446.
20. Mehta, B.K., Verma, M., & Mehta, D. (2005). Novel steroids from the seeds of Centratherum anthelminticum. Natural Product Research, 19(5), 435-442.
21. Panders, C., & Delaude, C. (1994). Structure elucidation of an acetylated saponin of Blighia welwitschii by NMR spectroscopy. Carbohydrate Research, 263, 79-88.
22. Scott, W.E., & Krewson, C.F. (1965). Vernonia anthelmintica (L.) willd. The effect of storage on the epoxy content of the seed oil and trivernolin. Journal of the American Oil Chemists' Society, 42, 147-149.
23. Shany, S., Gestener, B., Birk, Y., Bondi, A., & Kirson, I. (1972). Isolation of hederagenin and its saponin from alfalfa. Israel Journal of Chemistry, 10, 881-884.
24. Singh, R.S., Pandey, S.N., Singh, L.B., & Sen, S.P. (1981). Studies on Centratherum anthelminticum (Willd.) Kuntze syn. Vernonia anthelminticum Willd. (Family: Compositae) in clinical cases of helminthiasis. Journal of Scientific Research of Plants Medicine, 2, 47-54.
25. Singhal, K.C., Madan, B.R., & Saxena, P.N. (1977). Effect of drug on the nerve muscle complex of Setaria cervi. Indian Journal of Medicinal Research, 66, 517-521.
26. Singhal, K.C., Sharma, S., & Mehta, B.K. (1992). Antifilarial activity of Centratherum anthelminticum seed extracts on Setaria cervi. Indian Journal of Experimental Biology, 30(6), 546-548.
27. Tori, K., Seo, S., Yoshimura, Y., Nakamura, M., Tomita, Y., & Ishii, H. (1976). C-13 NMR spectra of saikogenins - Stereo chemical dependence in hydroxylation effects upon C-13 chemical shifts of oleanene type triterpenoids. Tetrahedron Letters, 46, 4167-4170.
28. Voutquenne, L., Guinot, P., Thoison, O., Sevenet, T., & Lavaud, C. (2003). Oleanolic glycosides from Pometia ridleyi. Phytochemistry, 64, 781-789.