Three new cycloartenol triterpenoid saponins from the roots of cimicifuga simplex wormsk

Molecules

Volumn 16, Issue 6, 2011, Pages 4348-4357

  Kuang, Haixue ^a   Su, Yang ^a   Yang, Bingyou ^a   Xia, Yonggang ^a   Wang, Qiuhong ^a   Wang, Zhibin ^a   Yu, Zhengfan ^a  

^a HEILONGJIANG UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

9,19 cyclanstane triterpenic glycosides; Cimicifuga simplex Wormsk; Cycloartenol triterpenoid saponins

Indexed keywords

SAPONIN;

ARTICLE; CHEMISTRY; CIMICIFUGA; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT;

CIMICIFUGA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT ROOTS; SAPONINS;

EID: 79959618747     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16064348     Document Type: Article

References (28)

1. Schmid, D.; Woehs, F.; Svoboda, M.; Thalhammer, T.; Chiba, P.; Moeslinger, T. Aqueous extracts of Cimicifuga racemosa and phenolcarboxylic constituents inhibit production of proinflammatory cytokines in LPS-stimulated human whole blood. Can. J. Physiol. Pharmacol. 2009, 87, 963-972.
2. Liu, I.M.; Chi, T.C.; Hsu, F.L.; Chen, C.F.; Cheng, J.T. Isoferulic acid as active principle from the rhizoma of Cimicifuga dahurica to lower plasma glucose in diabetic rats. Planta Med. 1999, 65, 712-714.
3. Kim, H.Y.; Shin, H.S.; Park, H.; Kim, Y.C.; Yun, Y.G.; Park, S.; Shin, H.J.; Kim, K. In vitro inhibition of coronavirus replications by the traditionally used medicinal herbal extracts, Cimicifuga rhizoma, Meliae cortex, Coptidis rhizoma, and Phellodendron cortex. J. Clin. Virol. 2008, 41, 122-128. (Pubitemid 351179456)
4. Hirabayashi, T.; Ochiai, H.; Sakai, S.; Nakajima, K.; Terasawa, K. Inhibitory effect of ferulic acid and isoferulic acid on murine interleukin-8 production in response to influenza virus infections in vitro and in vivo. Planta Med. 1995, 61, 221-226.
5. Sakai, S.; Kawamata, H.; Kogure, T.; Mantani, N.; Terasawa, K.; Umatake, M.; Ochiai, H. Inhibitory effect of ferulic acid and isoferulic acid on the production of macrophage inflammatory protein-2 in response to respiratory syncytial virus infection in RAW264.7 cells. Mediators Inflamm. 1999, 8, 173-175. (Pubitemid 29332057)
6. Li, J.X.; Yu, Z.Y. Cimicifugae rhizoma: from origins, bioactive constituents to clinical outcomes. Curr. Med. Chem. 2006, 13, 2927-2951.
7. Cao, P.; Pu, X.F.; Peng, S.L.; Zhang, X.R.; Ding, L.S. Chemical constituents from Cimicifuga foetida. J. Asian Nat. Prod. Res. 2005, 7, 145-149. (Pubitemid 40139371)
8. Li, C.J.; Li, Y.H.; Xiao, P.G.; Mabry, T.J.; Watson, W.H.; Krawiec, M. A unusual cycloartane triterpenoid from Cimicifuga foetida. Phytochemistry 1996, 42, 489-494. (Pubitemid 126655056)
9. Sun, L.R.; Qing, C.; Zhang, Y.L.; Jia, S.Y.; Li, Z.R.; Pei, S.J.; Qiu, M.H.; Gross, M.L.; Qiu, S.X. Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells. Beilstein J. Org. Chem. 2007, 3, 3-8.
10. Genjiro, K.; Sachiko, H.; Yoshikazu, K.; Tsunematsu, T. Studies on the constituents of Cimicifuga spp. XIII. Structure of Cimicifugoside. Chem. Pharm. Bull. 1977, 25, 3182-3189.
11. Genjiro, K.; Mayumi, I.; Yoshie, S.; Makio, S.; Akiko, K.; Takashi, I. Studies on the constituents of Cimicifuga species. XIV. A new xyloside from the aerial parts of Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1994, 42, 1106-1110.
12. Akiko, K.; Makio, S.; Satoshi, K.; Genjiro, K.; Shigeo, N.; Shinji, F. Studies on the constituents of Cimicifuga species. XV. Two new diglycosides from the aerial parts of Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1994, 42, 1940-1943.
13. Akiko, K.; Kei, S.; Mayumi, I.; Makio, S.; Katsuhiko, M.; Genjiro, K. Studies on the constituents of Cimicifuga species. XVI. Three new cycloartane xylosides from the aerial parts of Cimicifuga simplex Wormskjord. Chem. Pharm. Bull. 1995, 43, 279-283.
14. Akiko, K.; Makio, S.; Genjiro, K. Studies on the constituents of Cimicifuga species. XVII. Four new glycosides from the aerial parts of Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1994, 43, 1167-1170.
15. Akiko, K.; Makio, S.; Genjiro, K. Studies on the constituents of Cimicifuga species. XVIII. Four new xylosides from the aerial parts of Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1996, 44, 167-172.
16. Akiko, K.; Makio, S.; Genjiro, K.; Toshio, M. Studies on the constituents of Cimicifuga species. XIX. Eight new glycosides from Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1996, 44, 2078-2085.
17. Akiko, K.; Masayuki, T.; Makio, S.; Yasuko, I.; Toshimasa, I.; Toshio, M.; Genjiro, K. Studies on the constituents of Cimicifuga species. XX. Absolute stereostructures of cimicifugoside and actein from Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1998, 46, 467-472.
18. Akiko, K.; Masayuki, T.; Makio, S.; Toshio, M.; Genjiro, K. Studies on the constituents of Cimicifuga species. XXI. Two new cyclolanostanol xylosides, Bugbanosides A and B from Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1998, 46, 1001-1007.
19. Akiko, K.; Masayuki, T.; Makio, S.; Toshio, M.; Genjiro, K. Studies on the constituents of Cimicifuga species. XXVI. Twelve new cyclolanostanol glycosides from the underground parts of Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1999, 47, 511-516.
20. Toshihiro, A.; Ryuichi, H.; Kazuo, K.; Yumiko, K.; Tamotsu, N. Cycloarta-16,24-dien-3β-ol: revised structure of cimicifugenol, a cycloartane triterpenoid. Chem. Pharm. Bull. 1999, 47, 1157-1160.
21. Akiko, K.; Makio, S.; Genjiro, K. Studies on the constituents of Cimicifuga species. XXVII. Malonyl cyclolanostanol glycosides from the underground parts of Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 1999, 47, 1175-1179.
22. Akiko, K.; Makio, S.; Daisuke, T.; Genjiro, K. Studies on the constituents of Cimicifuga species. XXVIII. Four new cycloart-7-enol glycosides from the underground parts of Cimicifuga simplex Wormsk. Chem. Pharm. Bull. 2001, 49, 437-441.
23. Qiu, M.; Kim, J.H.; Lee, H.K.; Min, B.S. Anticomplement activity of cycloartane glycosides from the rhizome of Cimicifuga foetida. Phytother. Res. 2006, 20, 945-948. (Pubitemid 44763778)
24. Tian, Z.; Pan, R.L.; Si, J.Y.; Xiao, P.G. Cytotoxicity of cycloartane triterpenoids from aerial part of Cimicifuga foetida. Fitoterapia 2006, 77, 39-42 (Pubitemid 43012719)
25. Tian, Z.; Pan, R.L.; Chang, Q.; Xiao, P.G.; Wu, E. Cimicifuga foetida extract inhibits proliferation of hepatocellular cells via induction of cell cycle arrest and apoptosis. J. Ethnopharmacol. 2007, 114, 227-233. (Pubitemid 47539827)
26. Jianhua, J.; Dong, L.; Junshan, Y. The spectroscopic features of natural 9,19-cyclolanstane triterpenic glycosides. Chin. J. Magn. Reson. 2001, 18, 79-90.
27. Jian, X.L.; Shigetoshi, K.; Masao, H.; Sadao, Y.; Motoo, S.; Naoko, O.; Hiroshi, M.; Tsuneo, N. Constituents of Cimicifugae Rhizoma. I. Isolation and Characterization of Ten New Cycloartenol Triterpenes from Cimicifuga heracleifolia Komarov. Chem. Pharm. Bull. 1993, 41, 832-841.
28. Li, G.Y.; Zhang, Y.H.; Yang, B.Y.; Xia, Y.G.; Zhang, Y.L.; Lv, S.W.; Kuang, H.X. Leiyemudanosides A-C, three new bidesmosidic triterpenoid saponins from the roots of Caulophyllum robustum. Fitoterapia 2010, 81, 200-204.