Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives.
Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 microM.
Lambert
Joshua D
JD
Department of Chemical Biology, Ernest Mario School of Pharmacy, Rutgers, The State University of New Jersey, Piscataway, NJ 08854-8020, USA.
Rice
Joseph E
JE
Hong
Jungil
J
Hou
Zhe
Z
Yang
Chung S
CS
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D016718:Arachidonic Acid / Q000378:metabolism; D002392:Catechin / Q000031:analogs & derivatives* / Q000378:metabolism / Q000494:pharmacology; D002460:Cell Line; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D009569:Nitric Oxide / Q000096:biosynthesis; D013329:Structure-Activity Relationship; D013662:Tea / Q000737:chemistry
D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D008070:Lipopolysaccharides; D013662:Tea; D016718:Arachidonic Acid; D009569:Nitric Oxide; D002392:Catechin