Cytotoxic oleanane-type triterpenoid saponins from the rhizomes of Anemone rivularis var. flore-minore

Molecules

Volumn 19, Issue 2, 2014, Pages 2121-2134

  Wang, Xiaoyang ^a,b   Wang, Minchang ^c   Xu, Min ^c   Wang, Yi ^b   Tang, Haifeng ^a,b   Sun, Xiaoli ^a,b  

^a FOURTH MILITARY MEDICAL UNIVERSITY   (China)

^b FOURTH MILITARY MEDICAL UNIVERSITY   (China)

^c XI'AN MODERN CHEMISTRY RESEARCH INSTITUTE   (China)

Author keywords

Anemone rivularis var. flore minore; Cytotoxicity; Triterpenoid saponin

Indexed keywords

ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; OLEANANE; OLEANOLIC ACID; PLANT EXTRACT; SAPONIN; TRITERPENE;

ANEMONE; ARTICLE; CHEMISTRY; DRUG SCREENING; HELA CELL LINE; HEPG2 CELL LINE; HUMAN; ISOLATION AND PURIFICATION; RHIZOME;

ANEMONE; ANTINEOPLASTIC AGENTS, PHYTOGENIC; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HEP G2 CELLS; HUMANS; OLEANOLIC ACID; PLANT EXTRACTS; RHIZOME; SAPONINS; TRITERPENES;

EID: 84894621225     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19022121     Document Type: Article

References (31)

1. National Pharmacopoeia Committee. Pharmacopoeia of People's Republic of China; Chemical Industry Press: Beijing, China, 2010; p. 157.
2. Ye, W.C.; Zhang, Q.W.; Zhao, S.X.; Che, C.T. Four new oleanane saponins from Anemone anhuiensis. Chem. Pharm. Bull. 2001, 49, 632-634.
3. Lu, J.C.; Xu, B.B.; Gao, S.; Fan, L.; Zhang, H.F.; Liu, R.X.; Kodama, H. Structure elucidation of two triterpenoid saponins from rhizome of Anemone raddeana. Regel. Fitoterapia 2009, 80, 345-348.
4. Wang, M.K.; Wu, F.E.; Chen, Y.Z. Triterpenoid saponins from Anemone hupehensis. Phytochemistry 1997, 44, 333-335.
5. Mimaki, Y.; Watanabe, K.; Matsuo, Y.; Sakagami, H. Triterpene glycosides from the tubers of Anemone coronaria. Chem. Pharm. Bull. 2009, 57, 724-729.
6. Sun, Y.X.; Liu, J.C.; Liu, D.Y. Phytochemicals and bioactivities of Anemone raddeana Regel: A review. Pharmazie 2011, 66, 813-821.
7. Zhang, L.T.; Zhang, Y.W.; Takaishi, Y.; Duan, H.Q. Antitumor triterpene saponins from Anemone flaccida. Chin. Chem. Lett. 2008, 19, 190-192.
8. Wang, J.L.; Liu, K.; Gong, W.Z.; Wang, Q.; Xu, D.T.; Liu, M.F.; Bi, K.L.; Song, Y.F. Anticancer, antioxidant, and antimicrobial activities of Anemone (Anemone cathayensis). Food Sci. Biotechenol. 2012, 21, 551-557.
9. Wang, J.R.; Ma, J.Q.; Peng, L.L.; Feng, J.T.; Ding, L.S. Chemical constituents and antifeeding activity of Anemone tomentosa. Acta Bot. Boreali. Occid. Sin. 1998, 18, 643-644.
10. Flora of China Editorial Committee of Chinese Academy of Sciences. Flora of China; Science Press: Beijing, China, 1980; Volume 28, p. 24.
11. Ding, Y.; Tang, H.F.; Wang, J.B.; Liu, D.; Tian, X.R.; Wang, X.Y.; Zhou, X.M. Triterpenoid saponins from Anemone rivularis var. flore-minore. Biochem. Syst. Ecol. 2011, 39, 236-239.
12. Ding, Y.; Tian, X.R.; Tang, H.F.; Feng, J.T.; Zhang, W.; Hai, W.L.; Wang, X.Y.; Wang, Y. Two new glycosides from the whole plant of Anemone rivularis var. flore-minore. Phytochem. Lett. 2012, 5, 668-672.
13. Wang, Y.; Kang, W.; Hong, L.J.; Hai, W.L.; Wang, X.Y.; Tang, H.F.; Tian, X.R. Triterpenoid saponins from the root of Anemone tomentosa. J. Nat. Med. 2013, 67, 70-77.
14. Wang, X.Y.; Chen, X.L.; Tang, H.F.; Gao, H.; Tian, X.R.; Zhang, P.H. Cytotoxic triterpenoid saponins from the rhizomes of Anemone taipaiensis. Planta Med. 2011, 77, 1550-1554.
15. Wang, X.Y.; Zhang, W.; Gao, K.; Lu, Y.Y.; Tang, H.F.; Sun, X.L. Oleanane-type saponins from the rhizomes of Anemone taipaiensis and their cytotoxic activities. Fitoterapia 2013, 89, 224-230.
16. Wang, X.Y.; Gao, H.; Zhang, W.; Li, Y.; Cheng, G.; Sun, X.L.; Tang, H.F. Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis. Bioorg. Med. Chem. Lett. 2013, 23, 5714-5720.
17. Nie, R.L.; Tanakaa, T.; Miyakoshia, M.; Kasaia, R.; Moritaa, T.; Zhou, J.; Tanaka, O. A triterpenoid saponin from Thladiantha hookeri var. pentadactyla. Phytochemistry 1989, 28, 1711-1715.
18. Mahato, S.B.; Kundu, A.P. 13C-NMR Spectra of pentacyclic triterpenoidse-A compilation and some salient features. Phytochemistry 1994, 37, 1517-1575.
19. De Marino, S.; Borbone, N.; Iorizzi, M.; Esposito, G.; McClintock, J.B.; Zollo, F. Bioactive asterosaponins from the starfish Luidia quinaria and Psilaster cassiope. Isolation and structure characterization by two-dimensional NMR spectroscopy. J. Nat. Prod. 2003, 66, 515-519.
20. Zheng, Q.; Koike, K.; Han, L.K.; Okuda, H.; Nikaido, T. New biologically active triterpenoid saponins from Scabiosatschiliensis. J. Nat. Prod. 2004, 67, 604-613.
21. Xu, T.H.; Xu, Y.J.; Li, H.X.; Han, D.; Zhao, H.F.; Xie, S.X.; Xu, D.M. Two new triterpenoid saponins from Pulsatillacernua (Thunb.) Bercht. etOpiz. J. Asian Nat. Prod. Res. 2007, 9, 705-711.
22. Werner, S.; Nebojsa, S.; Robert, W.; Robert, S.; Olaf, K. Complete assignments of 1H and 13C-NMR resonances of oleanolic acid, 18α-oleanolic acid, ursolic acid and their 11-oxo derivatives. Magn. Reson. Chem. 2003, 41, 636-638.
23. Zhang, W.; Yao, M.N.; Tang, H.F.; Tian, X.R.; Wang, M.C.; Ji, L.J.; Xi, M.M. Triterpenoid saponins with anti-myocardial ischemia activity from the whole plants of Clematis tangutica. Planta Med. 2013, 79, 673-679.
24. Mimaki, Y.; Yokosuka, A.; Hamanaka, M.; Sakuma, C.; Yamori, T.; Sashida, Y. Triterpene saponins from the roots of Clematis chinensis. J. Nat. Prod. 2004, 67, 1511-1516.
25. Lavaud, C.; Crublet, M.L.; Pouny, I.; Litaudon, M.; Sdonet, T. Triterpeniod saponins from the stem bark of Elattostachys apetala. Phytochmistry 2001, 57, 469-478.
26. Zhang, Q.W.; Ye, W.C.; Che, C.T.; Zhao, S.X. Triterpene saponins from Pulsatilla cernua. Acta Pharm. Sin. 2000, 35, 756-759.
27. Schenkel, E.P.; Werner, W.; Schulte, K.E. Saponins from Thinouia coriaceae. Planta Med. 1991, 57, 463-467.
28. Sawada, H.; Miyakoshi, M.; Isoda, S.; Ida, Y.; Shoji, J. Saponins from leaves of Acanthopanax sieboldianus. Phytochemistry 1993, 34, 1117-1121.
29. Bang, S.C.; Lee, J.H.; Song, G.Y.; Kim, D.H.; Yoon, M.Y.; Ahn, B.Z. Antitumor activity of Pulsatilla koreana saponins and their structure-activity relationship. Chem. Pharm. Bull. 2005, 53, 1451-1454.
30. Yokosuka, A.; Sano, T.; Hashimoto, K.; Sakagami, H.; Mimaki, Y. Triterpene glycosides from the whole plant of Anemone hupehensis var. japonica and their cytotoxic activity. Chem. Pharm. Bull. 2009, 57, 1425-1430.
31. Alley, M.C.; Scudiero, D.A.; Monks, A.; Hursey, M.L.; Czerwinski, M.J.; Fine, D.L.; Abbott, B.J.; Mayo, J.G.; Shoemaker, R.H.; Boyd, M.R. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res. 1988, 48, 589-601.