title: Synthesis and cytotoxic activities of E-resveratrol derivatives.
abstract: The present study was designed to synthesize derivatives of E-resveratrol and evaluate their cytotoxic activity in vitro. Different functional groups were conjugated with the phenolic hydroxyl group of E-resveratrol, and the double bond of E-resveratrol was reduced. The in vitro cytotoxicity of the synthetic derivatives was evaluated against three tumor cell lines (A549, LAC, and HeLa) using the MTT assay. Twenty-six E-resveratrol derivatives were synthesized and their structures were confirmed by (1)H NMR, MS, IR, and elemental analyses. Compounds 1-6, 12, 15-21, and 23-26 were reported for the first time. Among them, Compounds 1, 2, 4, 5, and 9-11, showed significant cytotoxicity against tumor cells; especially, Compound 1 showed an IC50 value of 4.38 μmol · L(-1) in the A549 cells which was 15-fold more active than E-resveratrol; Compound 9 showed an IC50 value of 1.41 μmol · L(-1) in the HeLa cell line which was 90-fold more active than E-resveratrol, and close to adriamycin. The structure-activity relationships were also investigated. Compounds 1, 2 and 9-11 may serve as potential lead compounds for the discovery of new anticancer drugs.
authors.affiliation: Sino-German Joint Research Institute of Nanchang University, Nanchang 330047, China; Jiangxi Provincial Institute for Food and Drug Control, Jiangxi Provincial Engineering Research Center for Drug and Medical Device Quality, Nanchang 330029, China.
authors.forename: Ting
authors.initials: T
authors.lastname: Hong
authors.affiliation: Sino-German Joint Research Institute of Nanchang University, Nanchang 330047, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Jiang
authors.affiliation: Sino-German Joint Research Institute of Nanchang University, Nanchang 330047, China.
authors.forename: Huai-Ming
authors.initials: HM
authors.lastname: Dong
authors.affiliation: Chinese Academy of Sciences, South China Botanical Garden, Guangzhou 510650, China.
authors.forename: Sheng-Xiang
authors.initials: SX
authors.lastname: Qiu
authors.affiliation: Sino-German Joint Research Institute of Nanchang University, Nanchang 330047, China. Electronic address: luyzsu@hotmail.com.
authors.forename: Yu
authors.initials: Y
authors.lastname: Lu
mesh_terms: D000230:Adenocarcinoma / Q000188:drug therapy; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D005260:Female; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008175:Lung Neoplasms / Q000188:drug therapy; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D002583:Uterine Cervical Neoplasms / Q000188:drug therapy
chemical_list: D000970:Antineoplastic Agents; D013267:Stilbenes; D000077185:Resveratrol
keywords: Cytotoxic activity; E-resveratrol derivatives; Structure-activity relationships; Synthesis