Chemical transformations of oxyresveratrol (trans-2,4,3′,5′-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 21, 2006, Pages 5650-5653

  Likhitwitayawuid, Kittisak ^a   Sornsute, Acom ^a   Sritularak, Boonchoo ^a   Ploypradith, Poonsakdi ^b  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b CHULABHORN RESEARCH INSTITUTE   (Thailand)

Author keywords

Cytotoxicity; Oxyresveratrol; Stilbene; Tyrosinase inhibitor

Indexed keywords

2 METHOXY 4,3',5' TRIHYDROXYSTILBENE; 2,3' DIMETHOXY 4,5' DIHYDROXYSTILBENE; 2,4,3',5' TETRAHYDROXYBIBENZYL; 2,4,3',5' TETRAMETHOXYBIBENZYL; 2,4,3',5' TETRAMETHOXYSTILBENE; 4,3' DIMETHOXY 2,5' DIHYDROXYSTILBENE; ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; DOXORUBICIN; ELLIPTICINE; LEVODOPA; OXYGENASE INHIBITOR; OXYRESVERATROL; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CHEMICAL REACTION; CONTROLLED STUDY; CYTOTOXICITY; DRUG TRANSFORMATION; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROGENATION; KINETICS; METHYLATION; MUSHROOM;

CELL LINE, TUMOR; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; KINETICS; MONOPHENOL MONOOXYGENASE; PLANT EXTRACTS; STILBENES;

BASIDIOMYCOTA; TETRA;

EID: 33748766664     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.08.018     Document Type: Article

References (19)

1. Mongkolsuk S., Alexander R., and Towers R. J. Chem. Soc. (1957) 2231
2. Likhitwitayawuid K., Sritularak B., Benchanak K., Lipipun V., Mathew J., and Schinazi R.F. Nat. Prod. Res. 19 (2005) 177
3. Poopyruchpong N., Rungruangsak K., Nimmanpisut S., Panijpan B., and Ratanabanangkoon K. J. Sci. Soc. Thai. 4 (1978) 163
4. Sritularak B., De-Eknamkul W., and Likhitwitayawuid K. Thai. J. Pharm. Sci. 22 (1998) 149
5. Kim Y.M., Yun J., Lee C.K., Lee H., Min K.R., and Kim Y. J. Biol. Chem. 277 (2002) 16340
6. Tengamnuay, P.; Pengrungruangwong, K.; Likhitwitayawuid, K. In Proceedings of the IFCC Conference Cosmetics: Where Science Meets Dream, Seoul, Korea, September 22-24, 2003, pp 201-212.
7. Chung K.O., Kim B.Y., Lee M.H., Kim Y.R., Chung H.Y., Park J.H., and Moon J.O. J. Pharm. Pharmacol. 55 (2003) 1695
8. Lorenz P., Roychowdhury S., Engelmann M., Wolf G., and Horn T.F.W. Nitric Oxide 9 (2003) 64
9. Andrabi S.A., Spina M.G., Lorenz P., Ebmeyer U., Wolf G., and Horn T.F.W. Brain Res. 1017 (2004) 98
10. Full experimental details about the preparations and biological evaluations of derivatives of 1 are available as Supporting Information which can be obtained upon request to the corresponding author.
11. Likhitwitayawuid K., Sritularak B., and De-Eknamkul W. Planta Med. 66 (2000) 275
12. Sritularak, B. Chemical constituents of Artocarpus lakoocha and A. gomezianus. MS thesis, Chulalongkorn University, 1998; pp 101-102.
13. Likhitwitayawuid K., and Sritularak B. J. Nat. Prod. 64 (2001) 1457
14. Shimizu K., Kondo R., and Sakai K. Planta Med. 66 (2000) 11
15. Shin N.H., Ryu S.Y., Choi E.J., Kang S.H., Chang I.M., Min K.R., and Kim Y. Biochem. Biophys. Res. Commun. 243 (1998) 801
16. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107
17. Plumb J.A., Milroy R., and Kaye S.B. Cancer Res. 49 (1989) 4435
18. Pettit G.R., Singh S.B., Niven M.L., Hamel E., and Schmidt J.M. J. Nat. Prod. 50 (1987) 119
19. Guengerich F.P., Chun Y.J., Kim D., Gillam E.M.J., and Shimada T. Mutation Res. 523-524 (2003) 173