Actaeaepoxide 3-O-β-d-Xylopyranoside, a New Cycloartane Glycoside from the Rhizomes of Actaea racemosa (Cimicifuga racemosa)

Abstract

A new cycloartane glycoside (1) was obtained from a minor triterpene fraction of the rhizome extract of Actaea racemosa (synonym: Cimicifuga racemosa) along with a known compound, cimigenol 3-O-beta-D-xylopyranoside. The structure of 1 was elucidated as 20(S),22(R),23(R),24(S)-12beta-acetoxy-16beta:23,23alpha:24-diepoxy-3beta,22beta,25-trihydroxy-9,19-cyclolanost-7-ene 3-O-beta-D-xylopyranoside (actaeaepoxide 3-O-beta-D-xylopyranoside) on the basis of spectral and chemical evidence.

9,10-seco-9,19-Cyclolanostane arabinosides from the roots of Actaea podocarpa

“…The DEPT experiment resolved the 35 carbon signals as 7 methyls, 9 methylenes, 10 methines and 9 quaternary carbons. The signals in the 1 H NMR spectrum (see Table 1 (Shao et al, 2000;Hamburger et al, 2001;Wende et al, 2001;Kusano et al, 2001;He et al, 2000). However, the signals for cyclopropane methylene protons (2H-19) and two quaternary carbons (C-9 and C-10) were not observed at characteristic high magnetic field indicating a 9,10-seco-9,19-cyclolanostane derivative (Li et al, 1993;Kadota et al, 1995 (C-15, C-19 and C-24) which indicated the quaternary centers adjacent to them.…”

“…It has also been used for the treatment of diarrhea and sore throat (Watanabe et al, 2002). A number of cyclolanostane type triterpenes and their glycosides (Shao et al, 2000;Hamburger et al, 2001;Wende et al, 2001;Kusano et al, 2001;He et al, 2000) and phenylpropenoids and their glycosides (Kruse et al, 1999;Chen et al, 2002a) have been reported from black cohosh. It is usually collected from the wild in North America where its range overlaps with the closely related summer cohosh (A. podocarpa) (Zerega et al, 2002).…”

Black cohosh: Coming full circle?

“…Whether black cohosh contains the isoflavone formononetin is still under debate (Jarry and Harnischfeger, 1985;Panossian et al, 2004;Jiang et al, 2006). The principal bioactive constituents of black cohosh are N--methylserotonin and the triterpene glycosides actein, 23-epi-26-deoxyactein, and cimicifugoside Khan, 2000, 2001;Shao et al, 2000;Wende et al, 2001;Chen et al, 2002;Watanabe et al, 2002;Powell et al, 2008).…”

Molecular structure of actein: 13C CPMAS NMR, IR, X-ray diffraction studies and theoretical DFT–GIAO calculations

“…There are above 40 triterpene glycosides found in C. racemosa extract [7][8][9][10][11][12][13][14] of which actein (Fig. 1) is one of the most studied.…”