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Absolute Configuration of Resveratrol Oligomers Isolated from Hopea utilis
Author(s) -
Ito Tetsuro,
Hoshino Ryosuke,
Iinuma Munekazu
Publication year - 2015
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400146
Subject(s) - dipterocarpaceae , resveratrol , chemistry , pentamer , absolute configuration , phytochemical , trimer , stereochemistry , organic chemistry , biochemistry , botany , dimer , biology
Phytochemical studies on a stem of Hopea utilis (Dipterocarpaceae) resulted in the isolation of two new resveratrol derivatives, namely hopeaside E ( 1 ; resveratrol trimer) and hopeaside F ( 2 ; resveratrol pentamer), together with ten known resveratrol derivatives, 3 – 12 . The structures of the new compounds were elucidated by spectroscopic analyses, including NMR experiments, and their absolute configurations were determined on the basis of a comparative configurational analysis using the β ‐ D ‐glucopyranosyl group and chiroptical data. The absolute configuration of (+)‐balanocarpol ( 3 ) was also determined by acid‐catalyzed skeletal conversion.