Oxyresveratrol: Structural Modification and Evaluation of Biological Activities
AbstractOxyresveratrol (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
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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.
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(4):489.Chicago/Turabian Style
Chatsumpun, Nutputsorn; Chuanasa, Taksina; Sritularak, Boonchoo; Lipipun, Vimolmas; Jongbunprasert, Vichien; Ruchirawat, Somsak; Ploypradith, Poonsakdi; Likhitwitayawuid, Kittisak. 2016. "Oxyresveratrol: Structural Modification and Evaluation of Biological Activities." Molecules 21, no. 4: 489.
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