title: 3,4,4'-Trihydroxy-trans-stilbene, an analogue of resveratrol, is a potent antioxidant and cytotoxic agent.
abstract: Resveratrol (3,5,4'-trihydroxy-trans-stilbene) is a naturally occurring polyphenol widely distributed in food and dietary plants. This phytochemical has been intensively studied as an efficient antioxidant and anticancer agent, and a variety of substituted stilbenes have been developed in order to improve the potency of resveratrol. In this work, we described the synthesis of 3,4,4 -trihydroxy-trans-stilbene (3,4,4'-THS), an analogue of resveratrol, and studied its antioxidant and cytotoxic activity in vitro. 3,4,4 -THS was much more efficient than resveratrol in protecting against free radical-induced lipid peroxidation, photo-sensitized DNA oxidative damage, and free radical-induced hemolysis of human red blood cells. More potent growth inhibition in cultured human leukemia cells (HL-60) was also observed for 3,4,4 -THS. The relationship between the antioxidant efficiency and cytotoxic activity was discussed, with the emphasis on inhibition of the free radical enzyme ribonucleotide reductase by antioxidants. The result that this subtle structure modification of resveratrol drastically improves its bioactivity provides important strategy to develop novel resveratrol-based molecules.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu, China.
authors.forename: Wenqing
authors.initials: W
authors.lastname: Cai
authors.forename: Liangwei
authors.initials: L
authors.lastname: Zhang
authors.forename: Yanlin
authors.initials: Y
authors.lastname: Song
authors.forename: Baoxin
authors.initials: B
authors.lastname: Zhang
authors.forename: Xuemei
authors.initials: X
authors.lastname: Cui
authors.forename: Guanming
authors.initials: G
authors.lastname: Hu
authors.forename: Jianguo
authors.initials: J
authors.lastname: Fang
mesh_terms: D000840:Anisoles / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004249:DNA Damage / Q000187:drug effects; D005609:Free Radicals / Q000737:chemistry; D018922:HL-60 Cells / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D007700:Kinetics; D019787:Linoleic Acid / Q000737:chemistry; D015227:Lipid Peroxidation / Q000187:drug effects; D015394:Molecular Structure; D018384:Oxidative Stress / Q000187:drug effects; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C570432:3,4,4'-trihydroxystilbene; D000840:Anisoles; D000970:Antineoplastic Agents; D000975:Antioxidants; D005609:Free Radicals; D013267:Stilbenes; D019787:Linoleic Acid; C060998:anisole; D000077185:Resveratrol