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Two New Resveratrol (=5‐[(1 E )‐2‐(4‐Hydroxyphenyl)ethenyl]benzene‐1,3‐diol) Tetramers with a Tetrahydrofuran Ring from Dipterocarpus grandiflorus
Author(s) -
Ito Tetsuro,
Tanaka Toshiyuki,
Iinuma Munekazu,
Nakaya Kenichi,
Takahashi Yoshikazu,
Sawa Ryuichi,
Murata Jin,
Darnaedi Dedy
Publication year - 2004
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.200490046
Subject(s) - chemistry , tetrahydrofuran , benzene , resveratrol , diol , ring (chemistry) , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , dimer , organic chemistry , solvent , biochemistry
Abstract Two new stilbene tetramers, grandiphenols A ( 1 ) and B ( 2 ), along with ten known stilbene oligomers and bergenin were isolated from the stem of Dipterocarpus grandiflorus. The structures of 1 and 2 composed of four resveratrol (=5‐[(1 E )‐2‐(4‐hydroxyphenyl)ethenyl]benzene‐1,3‐diol) units had eight asymmetric C‐atoms in the partial structures of a tetrahydrofuran and two dihydrobenzofuran moieties. Detailed spectroscopic analyses, especially HMBC and NOESY experiments, allowed to differentiate the configurations of 1 and 2 .