Novel and unusual triterpene from Black Cohosh. Determination of structure of 9,10-seco-9,19-cyclolanostane xyloside (cimipodocarpaside) by NMR, IR and Raman spectroscopy and DFT calculations

作者：Jamroz Marta K^*; Jamroz Michal H; Dobrowolski Jan Cz; Glinski Jan A; Davey Matthew H; Wawer Iwona

来源：Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy , 2011, 78(1): 107-112.

DOI：10.1016/j.saa.2010.09.005

• Actea racemosa
• Triterpene glycosides
• NMR spectroscopy
• IR and Raman spectroscopy
• PED analysis
• DFT calculations

A new triterpene xyloside, designated cimipodocarpaside was isolated from a Black Cohosh (Actea racemosa L) extract and its structure was elucidated by means of H-1, C-13 NMR, IR and Raman spectroscopy supported by B3LYP/6-31G** calculations. The vibrational spectra were interpreted using the PED analysis of 273 fundamentals. Its structure comprises four condensed rings A-D which are 6, 7, 6, and 5-membered. respectively. An oxiirane ring is located in the side chain and a xylose moiety is attached to the A-ring. Comparison of the experimental C-13 NMR data with the theoretical chemical shifts of 24S- and 24R-cimipodocarpaside isomers revealed that the isolated compound has the 24S-configuration. Combined spectroscopic and computational studies enabled the determination of the structure of cimipodocarpaside as (24S)-3 beta-hydroxy-24,25-oxiirane-16,23-dione-9,10-seco-9,19-cyclolanost-7(8),9(11),10(19)-trien-3-O-beta-D-xylopyranoside. Triterpenes with 7-membered ring were thus far isolated from only Actea podocarpa DC. plants. This is the first report on the isolation of such a compound from Black Cohosh.

• 出版日期2011-1