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Oxyresveratrol: Structural Modification and Evaluation of Biological Activities

1
Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand
2
Department of Biochemistry and Microbiology, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand
3
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, and Program in Chemical Biology, Chulabhorn Graduate Institute, 54 Kampaeng Phet 6 Road, Bangkok 10210, Thailand
*
Authors to whom correspondence should be addressed.
Academic Editors: Dominique Vervandier-Fasseur, Norbert Latruffe and Ole Vang
Molecules 2016, 21(4), 489; https://doi.org/10.3390/molecules21040489
Received: 29 February 2016 / Revised: 5 April 2016 / Accepted: 11 April 2016 / Published: 19 April 2016
(This article belongs to the Special Issue Improvements for Resveratrol Efficacy)
Oxyresveratrol (2,4,3′,5′-tetrahydroxystilbene, 1), a phytoalexin present in large amounts in the heartwood of Artocarpus lacucha Buch.-Ham., has been reported to possess a wide variety of biological activities. As part of our continuing studies on the structural modification of oxyresveratrol, a library of twenty-six compounds was prepared via O-alkylation, aromatic halogenation, and electrophilic aromatic substitution. The two aromatic rings of the stilbene system of 1 can be chemically modulated by exploiting different protecting groups. Such a strategy allows for selective and exclusive modifications on either ring A or ring B. All compounds were evaluated in vitro for a panel of biological activities, including free radical scavenging activity, DNA protective properties, antiherpetic activity, inhibition of α-glucosidase and neuraminidase, and cytotoxicity against some cancer cell lines. Several derivatives were comparably active or even more potent than the parent oxyresveratrol and/or the appropriate positive controls. The partially etherified analogs 5′-hydroxy-2,3′,4-trimethoxystilbene and 3′,5′-dihydroxy-2,4-dimethoxystilbene demonstrated promising anti-herpetic and DNA protective activities, offering new leads for neuropreventive agent research, whereas 5′-hydroxy-2,3′,4,-triisopropoxystilbene displayed anti-α-glucosidase effects, providing a new lead molecule for anti-diabetic drug development. 3′,5′-Diacetoxy-2,4-diisopropoxystilbene showed potent and selective cytotoxicity against HeLa cancer cells, but the compound still needs further in vivo investigation to verify its anticancer potential. View Full-Text
Keywords: oxyresveratrol; stilbene; free radicals; α-glucosidase; herpes simplex; cytotoxicity; Artocarpus lacucha; Artocarpus lakoocha oxyresveratrol; stilbene; free radicals; α-glucosidase; herpes simplex; cytotoxicity; Artocarpus lacucha; Artocarpus lakoocha
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MDPI and ACS Style

Chatsumpun, N.; Chuanasa, T.; Sritularak, B.; Lipipun, V.; Jongbunprasert, V.; Ruchirawat, S.; Ploypradith, P.; Likhitwitayawuid, K. Oxyresveratrol: Structural Modification and Evaluation of Biological Activities. Molecules 2016, 21, 489.

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