New Triterpene Diglycosides from the Rhizome of Cimifuga foetida

Five new 9,19-cycloartane triterpene diglycosides, which have been named cimiaceroside C (1), and cimifosides A-D (2-5) together with the known compounds cimiracemoside D (6), cimidahurine (7) and α-d-glucopyranosyl-l-β-d-fructofuranoside (8) were isolated from the rhizome of Cimicifuga foetida. The new triterpene diglycosides 1-5 were identified as cimiacerol-3-O-β-d-xylopyranosyl-(1''→3')-β-d-xylopyranoside, 12β-hydroxycimigenol-3-O-β-d-xylopyranosyl-(1''→3')-β-d-xylopyranoside, 25-O-acetylcimig- enol-3-O-β-d-xylopyranosyl-(1''→3')-β-d-xylopyranoside, 24-acetylhydroshengmanol-3-O-β-d-xylopyranosyl-(1''→3')-β-d-xylopyranoside and 26-deoxyacetylacteol-3-O-β-d-xylo- pyranosyl-(1''→3')-β-d-xylopyranoside, respectively, based on analysis of their spectral data and chemical reactions.

[1]  Michael L Gross,et al.  Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells , 2007, Beilstein journal of organic chemistry.

[2]  Jian-Xin Li,et al.  Cimicifugae rhizoma: from origins, bioactive constituents to clinical outcomes. , 2006, Current medicinal chemistry.

[3]  A. Culham,et al.  Phylogeny and Circumscription of Tribe Actaeeae (Ranunculaceae) , 2009 .

[4]  G. Tu,et al.  Two new cyclolanostanol xylosides from the aerial parts of Cimicifuga dahurica. , 2002, Journal of natural products.

[5]  A. Mesecar,et al.  Isolation, structure elucidation, and absolute configuration of 26-deoxyactein from Cimicifuga racemosa and clarification of nomenclature associated with 27-deoxyactein. , 2002, Journal of natural products.

[6]  Liu Zhong-rong.  STUDIES ON THE CHEMICAL CONSTITUENTS AND BIOLOGIC ACTIVITIES OF CIMICIFUGA , 2002 .

[7]  G. Kusano.  [Studies on the constituents of Cimicifuga species]. , 2001, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.

[8]  D. Mckenna,et al.  Black cohosh: efficacy, safety, and use in clinical and preclinical applications. , 2001, Alternative therapies in health and medicine.

[9]  G. Cordell,et al.  Triterpene glycosides from Cimicifuga racemosa. , 2000, Journal of natural products.

[10]  G. Kusano,et al.  Studies on the Constituents of Cimicifuga Species. XXVII. Malonyl Cyclolanostanol Glycosides from the Underground Parts of Cimicifuga simplex WORMSK. , 1999 .

[11]  T. Miyase,et al.  Studies on the Constituents of Cimicifuga Species. Part 22. Structures of Two New Cyclolanostanol Xylosides, Cimiacerosides A and B. , 1998 .

[12]  A. Culham,et al.  RECLASSIFICATION OF ACTAEA TO INCLUDE CIMICIFUGA AND SOULIEA (RANUNCULACEAE) : PHYLOGENY INFERRED FROM MORPHOLOGY, NRDNA ITS, AND CPDNA TRNL-F SEQUENC E VARIATION , 1998 .

[13]  S Lieberman,et al.  A review of the effectiveness of Cimicifuga racemosa (black cohosh) for the symptoms of menopause. , 1998, Journal of women's health.

[14]  A. Culham,et al.  Phylogeny of Actaea including Cimicifuga (Ranunculaceae) inferred from nrDNA ITS sequence variation , 1998 .

[15]  T. Miyase,et al.  STRUCTURES OF TWO NEW CYCLOLANOSTANOL XYLOSIDES, CIMIACEROSIDES A AND B , 1998 .

[16]  L. Cj.  STUDIES ON PHENOLIC GLYCOSIDES ISOLATED FRoM CIMICIFUGA DAHURICA , 1994 .

[17]  Jian-Xin Li,et al.  Constituents of Cimicifugae Rhizoma. I. Isolation and Characterization of Ten New Cycloartenol Triterpenes from Cimicifuga heracleifolia Komarov. , 1993 .

[18]  Takao Inoue,et al.  Studies on the Chinese Crude Drug "Shoma."V. Structures of 24-O-Acetylhydroshengmanol Xyloside and 22-Hydroxycimigenol Xyloside , 1981 .