One new and six known triterpene xylosides from Cimicifuga racemosa: FT-IR, Raman and NMR studies and DFT calculations

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• 作者：Marta K. Jamró ; z^a ; ^{marta.jamroz@wum.edu.pl} ; Micha艂 H. Jamró ; z^b ; Jan Cz. Dobrowolski^b ; ^c ; Jan A. Gli艅ski^d ; Micha艂 Gle艅sk^e
• 关键词：Triterpene xylosides ; Cimicifuga racemosa ; IR ; Raman ; NMR ; DFT calculations
• 刊名：Spectrochimica Acta Part A ; Molecular and Biomolecular Spectroscopy
• 出版年：2012
• 期刊代码：99_13861425
• 类别：ch
• 出版时间：July, 2012
• 卷：93
• 期：Complete
• 页码：10-18
• 文件大小：1046 K

摘要

One new and six known triterpene xylosides were isolated from Cimicifuga racemosa (black cohosh, Actaea racemosa). The structure of a new compound, designated as isocimipodocarpaside (1), was established to be (24S)-3尾-hydroxy-24,25-oxiirane-16,23-dione-9,10-seco-9,19-cyclolanost-1(10),7(8),9(11)-trien 3-O-尾-d-xylopyranoside, by means of ¹H and ¹³C NMR, IR and Raman spectroscopies and Mass Spectrometry. The six known compounds are: 23-epi-26-deoxycimicifugoside (2), 23-epi-26-deoxyactein (3), 25-anhydrocimigenol xyloside (4), 23-O-acetylshengmanol xyloside (5), 25-O-acetylcimigenol xyloside (6) and 3鈥?O-acetylcimicifugoside H-1 (7). On the basis of NMR data supported by DFT calculations of NMR shielding constants of (2), its structure, previously described as 26-deoxycimicifugoside was corrected and determined as 23-epi-26-deoxycimicifugoside. The ¹³C CPMAS NMR spectra of the studied compounds (1)-(7) provided data on their solid-state interactions. The IR and Raman spectra in the CO, CC, and CH stretching vibration regions clearly discriminate different triterpenes found in C. racemosa.