Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.bmcl.2010.12.029
Title: Methoxylation of resveratrol: Effects on induction of NAD(P)H Quinone-oxidoreductase 1 (NQO1) activity and growth inhibitory properties
Authors: Zhang, W.
Go, M.L. 
Keywords: Growth inhibitory effects
Methoxy analogs
NQO1 induction
Resveratrol
Structure-activity relationship
Issue Date: 1-Feb-2011
Citation: Zhang, W., Go, M.L. (2011-02-01). Methoxylation of resveratrol: Effects on induction of NAD(P)H Quinone-oxidoreductase 1 (NQO1) activity and growth inhibitory properties. Bioorganic and Medicinal Chemistry Letters 21 (3) : 1032-1035. ScholarBank@NUS Repository. https://doi.org/10.1016/j.bmcl.2010.12.029
Abstract: A series of methoxystilbenes (E and Z isomers) related to resveratrol were investigated for their effects on NQO1 induction in murine hepatoma cells and growth inhibitory effects on human cancer cell lines. Both activities were enhanced in compounds with methoxy groups on rings A and B of resveratrol but methoxylation of the di-meta (3,5) hydroxyl groups on ring A of resveratrol was found to be more critical for improving activity. Strikingly different structure-activity trends were observed, namely the association of E isomers with potent NQO1 induction activity and Z isomers with growth inhibitory properties. The introduction of ortho-methoxy groups on ring A greatly benefited NQO1 induction activity while meta/para methoxy groups on ring A were preferred for potent growth inhibitory effects. These results serve to highlight the contrasting effects on different activities brought about by methoxylation, which is widely employed as a structural modification approach to improve potency and bioavailability of resveratrol. It serves as a timely reminder that in the course of structural modification, a balance between optimizing desired outcomes against unwanted effects is necessary and the most potent analog need not always be the most desirable. © 2010 Elsevier Ltd. All rights reserved.
Source Title: Bioorganic and Medicinal Chemistry Letters
URI: http://scholarbank.nus.edu.sg/handle/10635/106142
ISSN: 0960894X
DOI: 10.1016/j.bmcl.2010.12.029
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