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NMR assignments and absolute configuration of kauranoids
Author(s) -
Tan R. X.,
Wang W. Z.,
Wu S. X.,
Yang L.
Publication year - 1995
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.1260330911
Subject(s) - chemistry , absolute configuration , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , circular dichroism , glycoside , carbon 13 nmr , nmr spectra database , spectral line , physics , astronomy
Abstract A new ent ‐kaurane diterpenoid glycoside has been shown to be the main sweetening constituent of the traditional medicines Aster tongolensis and A. ageratoides native to China. This study involved the total 1 H and 13 C spectral assignment of the compound and its degraded product by means of two‐dimensional NMR techniques (COSY, NOESY, HETCOR and TOCSY) and resulted in unambiguous spectral assignments, particularly in the heavily convoluted regions of the spectra. Concerning the absolute stereochemistry, the sweetener was determined to be (4 R ,5 S ,8 S ,9 S ,10,13 R )‐16,17‐dihydroxykauran‐19‐oic acid β‐D‐glucopyranosyl ester through a combination of circular dichroism and 2D NMR techniques.