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Oxyresveratrol: Structural Modification and Evaluation of Biological Activities

Chatsumpun, Nutputsorn ; Chuanasa, Taksina ; Sritularak, Boonchoo ; Lipipun, Vimolmas ; Jongbunprasert, Vichien ; Ruchirawat, Somsak ; Ploypradith, Poonsakdi ; Likhitwitayawuid, Kittisak

Molecules (Basel, Switzerland), 2016-04, Vol.21 (4), p.489-489 [Periódico revisado por pares]

Switzerland: MDPI

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Título:
Oxyresveratrol: Structural Modification and Evaluation of Biological Activities
Autor: Chatsumpun, Nutputsorn ; Chuanasa, Taksina ; Sritularak, Boonchoo ; Lipipun, Vimolmas ; Jongbunprasert, Vichien ; Ruchirawat, Somsak ; Ploypradith, Poonsakdi ; Likhitwitayawuid, Kittisak
Assuntos: Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Artocarpus lacucha ; Artocarpus lakoocha ; Cell Line, Tumor ; Cell Survival - drug effects ; cytotoxicity ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Free Radical Scavengers - chemical synthesis ; Free Radical Scavengers - chemistry ; Free Radical Scavengers - pharmacology ; free radicals ; herpes simplex ; Humans ; oxyresveratrol ; Plant Extracts - chemistry ; Plant Extracts - pharmacology ; stilbene ; Stilbenes - chemical synthesis ; Stilbenes - chemistry ; Stilbenes - pharmacology ; α-glucosidase
É parte de: Molecules (Basel, Switzerland), 2016-04, Vol.21 (4), p.489-489
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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Descrição: 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.
Editor: Switzerland: MDPI
Idioma: Inglês

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Oxyresveratrol: Structural Modification and Evaluation of Biological Activities

Chatsumpun, Nutputsorn ; Chuanasa, Taksina ; Sritularak, Boonchoo ; Lipipun, Vimolmas ; Jongbunprasert, Vichien ; Ruchirawat, Somsak ; Ploypradith, Poonsakdi ; Likhitwitayawuid, Kittisak

Switzerland: MDPI

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