title: One new and six known triterpene xylosides from Cimicifuga racemosa: FT-IR, Raman and NMR studies and DFT calculations.
abstract: 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)-3β-hydroxy-24,25-oxiirane-16,23-dione-9,10-seco-9,19-cyclolanost-1(10),7(8),9(11)-trien 3-O-β-d-xylopyranoside, by means of (1)H and (13)C 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'-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 (13)C 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.
authors.affiliation: Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Street, 02-097 Warsaw, Poland. marta.jamroz@wum.edu.pl
authors.forename: Marta K
authors.initials: MK
authors.lastname: Jamróz
authors.forename: Michał H
authors.initials: MH
authors.lastname: Jamróz
authors.forename: Jan
authors.initials: J
authors.lastname: Cz Dobrowolski
authors.forename: Jan A
authors.initials: JA
authors.lastname: Gliński
authors.forename: Michał
authors.initials: M
authors.lastname: Gleńsk
mesh_terms: D031885:Cimicifuga / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D006027:Glycosides; D010936:Plant Extracts; D014315:Triterpenes; C010807:xylosides