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Resveratrol‐Related Dehydrodimers: Laccase‐Mediated Biomimetic Synthesis and Antiproliferative Activity
Author(s) -
Bhusainahalli Vedamurthy M.,
Spatafora Carmela,
Chalal Malik,
VervandierFasseur Dominique,
Meunier Philippe,
Latruffe Norbert,
Tringali Corrado
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200664
Subject(s) - chemistry , enantiomer , stereocenter , circular dichroism , resveratrol , laccase , stereochemistry , chiral column chromatography , absolute configuration , trametes versicolor , bioassay , high performance liquid chromatography , biological activity , enzyme , in vitro , organic chemistry , enantioselective synthesis , biochemistry , catalysis , biology , genetics
Seven resveratrol‐related monomeric stilbenoids were submitted to biomimetic oxidative coupling in the presence of laccase from Trametes versicolor (TvL), and gave racemic dihydrobenzofuran dehydrodimers (±) ‐15 to (±) ‐21 . These products, after spectral characterization, were submitted to an antiproliferative activity bioassay against SW480 human colon cancer cells. Five racemates were found to be active, and were resolved by chiral HPLC. The pure enantiomers were subjected to circular dichroism measurements to establish their absolute configurations at C‐7 and C‐8. These enantiomerically pure compounds were submitted to the antiproliferative activity assay towards SW480 cells, and were all shown to be active with IC 50 values in the approximate range 20–90 μ M . In some cases, a significant difference between the activity of the 7 R ,8 R and 7 S ,8 S enantiomers was observed, but a defined configuration of the stereogenic centers does not appear to be a structural requirement for the activity. The comparison between the most active compounds and the inactive ones strongly suggests that the presence of a methoxy group in the position ortho to the C‐4 hydroxy group is highly detrimental to the activity.