Heracleifolinosides A-F, new triterpene glycosides from cimicifuga heracleifolia, and their inhibitory activities against hypoxia and reoxygenation

Planta Medica

Volumn 79, Issue 3-4, 2013, Pages 301-307

  Liu, Yan Ru ^a,c   Wu, Zhi Jun ^a   Li, Chun Tong ^a   Xi, Feng Min ^a   Sun, Lian Na ^b   Chen, Wan Sheng ^a  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

^b SECOND MILITARY MEDICAL UNIVERSITY   (China)

^c FUDAN UNIVERSITY   (China)

Author keywords

9,19 cycloartane triterpene bisglycosides; Cimicifuga heracleifolia; hypoxia; Ranunculaceae; reoxygenation

Indexed keywords

CIMICIFUGA HERACLEIFOLIA EXTRACT; HERACLEIFOLINOSIDE A; HERACLEIFOLINOSIDE B; HERACLEIFOLINOSIDE C; HERACLEIFOLINOSIDE D; HERACLEIFOLINOSIDE E; HERACLEIFOLINOSIDE F; NORKHELLOSIDE; PLANT EXTRACT; TRITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CELL DAMAGE; CELL HYPOXIA; CELL VIABILITY; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; MASS SPECTROMETRY; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REOXYGENATION; UMBILICAL VEIN ENDOTHELIAL CELL;

CELL HYPOXIA; CELL SURVIVAL; CIMICIFUGA; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; GLYCOSIDES; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANT EXTRACTS; RHIZOME; SAPONINS; TRITERPENES;

CIMICIFUGA HERACLEIFOLIA; RANUNCULACEAE;

EID: 84874944891     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0032-1328174     Document Type: Article

References (27)

1. China Pharmacopoeia Committee Pharmacopoeia of the P.R.C., The first division of 2005 edition. Beijing Chemical and Technologic Press: 2005; 50 51
2. New Medical College of Jiangsu Dictionary of Chinese Materia Medica, Vol. 1. Shanghai Shanghai Scientific and Technological Press: 1977; 451 454
3. 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
4. Liu Y., Chen D. H., Si J. Y., Tu G. Z., An D. G. Two new cyclolanostanol xylosides from the aerial parts of Cimicifuga dahurica. J Nat Prod: 2002; 65 1486 1488 (Pubitemid 35239638)
5. Takahira M., Kusano A., Shibano M., Kusano G., Sakurai N., Nagai M., Miyase T. Three new fukiic acid esters, cimicifugic acids A, B and C, from Cimicifuga simplex Wormsk. Chem Pharm Bull: 1998; 46 362 365 (Pubitemid 28124230)
6. Atsufumi I., Genjiro K., Tsutomu W., Toshio M. H. Hyaluronidase inhibitors from "Cimicifugae Rhizomao" (a mixture of the rhizomes of Cimicifuga dahurica and C. heracleifolia). J Nat Prod: 2010; 73 573 578
7. Chen S. N., Li W. K., Fabricant D. S., Santarsiero B. D., Mesecar A., Fitzloff J. F., Fong H. H., Farnsworth N. R. Isolation, structure elucidation, and absolute configuration of 26-deoxyactein from Cimicifuga racemosa and clarification of nomenclature associated with 27-deoxyactein. J Nat Prod: 2002; 65 601 605 (Pubitemid 34456955)
8. Ito M., Kondo Y., Takemoto T. Spasmolytic substances from Cimicifuga dahurica Maxim. Chem Pharm Bull: 1976; 24 580 583
9. Compton J. A., Culham A., Jury S. L. Reclassification of Actaea to include Cimicifuga and Souliea (Ranunculaceae): phylogeny inferred from morphology, nrDNA ITS, and cpDNA trn L-F sequence variation. Taxon: 1998; 47 593 634 (Pubitemid 28395392)
10. Compton J. A., Culham A. J., Gibbings G., Jury S. L. Phylogeny of Actaea including Cimicifuga (Ranunculaceae) inferred from nrDNA ITS sequence variation. Biochem Syst Ecol: 1998; 26 185 197 (Pubitemid 28267640)
11. Shao Y., Amanda H., Wang M. F., Zhang H. J., Geoffrey C., Mika B., Lemmo E. Triterpene glycosides from Cimicifuga racemosa. J Nat Prod: 2000; 63 905 910 (Pubitemid 30624470)
12. Lin Y. P., Qiu M. H., Li Z. R. Studies on the chemical constituents and biologic activities of Cimicifuga. Nat Prod Res Dev: 2002; 14 58 76
13. Li J. X., Yu Z. Y. Cimicifugae Rhizoma: from origins, bioactive constituents to clinical outcomes. Curr Med Chem: 2006; 13 2927 2951
14. Li J. X., Kadota S., Hattori M., Yoshimachi S., Shiro M., Oogami N., Mizuno H. Constituents of Cimicifugae Rhizoma. I. Isolation and characterization of ten new cycloartenol triterpenes from Cimicifuga heracleifolia Komarov. Chem Pharm Bull: 1993; 41 832 841 (Pubitemid 23240041)
15. Kusano G., Uchida H., Murakami Y., Sakurai N., Takemoto T. Studies on the constituents of Cimicifuga spp. XII. A revised structure of acerinol and the structures of the related compounds. Yakugaku Zasshi: 1976; 96 321 323
16. Kusano G., Hojo S., Kondo Y., Takemoto T. Studies on the constituents of Cimicifuga spp. XIII. Structure of cimicifugoside. Chem Pharm Bull: 1977; 25 3182 3184
17. Zhang Q. W., Ye W. C., Hao W. L., Zhao S. X., Che Z. T. Cycloartane glycosides from Cimicifuga dahurica. Chem Pharm Bull: 2001; 49 1468 1470
18. 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
19. Li C. J., Chen D. H., Xiao P. G. Chemical constituents of traditional Chinese drug "Sheng-mao" (Cimicifuga dahurica). III. Structures of cimicifugamide. Acta Chim Sin: 1995; 52 296
20. Ding P. Y., Zhu X. X., Cai M. S., Yu D. Q. Studies on synthesis and pharmacological activities of cimicifugamide from Cimicifuga dahurica, and its analogues. Acta Pharm Sin: 1997; 32 755 760 (Pubitemid 127465012)
21. Song Z. H., Wang B. D., Ba H., Tong X. T., Zhu D. Y., Jiang F. X. Studies on chemical constituents in roots of Paeonia sinjiangensis. China J Chin Mater Med: 2004; 29 748 751
22. Klaus P. L., Maki K., Andreas S., Herbert K. An ellagitannin, n -butyl gallate, two aryltetralin lignans, and an unprecedented diterpene ester from Pelargonium reniforme. Phytochemistry: 2008; 69 820 826
23. Li B. G., Zhou Z. Z. Chemistry of the new drug Di Ao Xin Xue Kang for treating cardiovascular diseases. Chin J New Drugs Clin Rem (in Chinese): 1994; 13 75 76
24. Tsuyoshi I., Hidetsugu T., Masafumi O., Toshihiro N. Pregnane- and furostane-type oligoglycosides from the seeds of Allium tuberosum. Chem Pharm Bull: 2004; 52 142 145
25. Hua H. M., Li X., Pei Y. H. The special characterization of Cycloartane triterpenoids. Nat Prod Res Dev: 2000; 13 65 70
26. Lu L., Chen J. C., Song H. J., Li Y., Nian Y., Qiu M. H. Five new triterpene bisglycosides with acyclic side chains from the rhizomes of Cimicifuga foetida L. Chem Pharm Bull: 2010; 58 729 733
27. Minpei K., Singo U., Kazuki W., Yoshihiro M. Chromones from the tubers of Eranthis cilicica and their antioxidant activity. Phytochemistry: 2009; 70 288 293