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Stereochemical assignment of five new lignan glycosides from Viscum album by NMR study combined with CD spectroscopy
Author(s) -
Nhiem Nguyen Xuan,
Lee Hwa Young,
Kim Nan Young,
Park Seon Ju,
Kim Eun Sil,
Han Jeong Eun,
Yang Heejung,
Kim Seung Hyun
Publication year - 2012
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.3875
Subject(s) - lignan , chemistry , glycoside , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , nuclear magnetic resonance spectroscopy , chemical shift
The chemical study of the leaves and twigs of Viscum album led to the isolation of five new lignan glycosides, namely, ligalbumosides A–E (2‐6) and one known lignan glycoside, alangilignoside C (1). The structures of five new lignan glycosides were determined to be (7 R ,8 S ,8' S )‐4,9,4'‐trihydroxy‐3,5,3',5'‐tetramethoxy‐7,9'‐epoxylignan 9‐ O ‐β‐D‐glucopyranoside (2), (7 S ,8 S ,7' S ,8' R )‐4,9,4'‐trihydroxy‐3,5,3',5',7'‐pentamethoxy‐7,9'‐epoxylignan 9‐ O ‐β‐D‐glucopyranoside (3), (7 R ,8 R ,7' S ,8' S )‐4,9,4'‐trihydroxy‐3,5,3',5',7'‐pentamethoxy‐7,9'‐epoxylignan 9‐ O ‐β‐D‐glucopyranoside (4), (7 S ,8 R ,7' S ,8' R )‐4,9,4'‐trihydroxy‐3,5,3',5',7'‐pentamethoxy‐7,9'‐epoxylignan 9‐ O ‐β‐D‐glucopyranoside (5), and (7 R ,8 S ,7' R ,8' S )‐4,9,4',7'‐tetrahydroxy‐3,5,3',5'‐tetramethoxy‐7,9'‐epoxylignan 9‐ O ‐β‐D‐glucopyranoside (6) using 1D‐, 2D‐NMR, and CD spectra, chemical methods, as well as comparing the results with those reported in the literature. Copyright © 2012 John Wiley & Sons, Ltd.