Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities.
Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activities against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated.
Sang
Shengmin
S
Department of Chemical Biology, Ernest Mario School of Pharmacy, Rutgers University, 164 Frelinghuysen Road, Piscataway, NJ 08854-8020, USA. ssang@rci.rutgers.edu
Lambert
Joshua D
JD
Tian
Shiying
S
Hong
Jungil
J
Hou
Zhe
Z
Ryu
Jae-He
JH
Stark
Ruth E
RE
Rosen
Robert T
RT
Huang
Mou-Tuan
MT
Yang
Chung S
CS
Ho
Chi-Tang
CT
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D016718:Arachidonic Acid / Q000378:metabolism; D044946:Biflavonoids / Q000737:chemistry*; D001671:Biochemistry / Q000379:methods; D002294:Carcinoma, Squamous Cell / Q000188:drug therapy; D002392:Catechin / Q000737:chemistry*; D002455:Cell Division / Q000187:drug effects; D002478:Cells, Cultured; D003110:Colonic Neoplasms / Q000188:drug therapy; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004427:Ear Diseases / Q000139:chemically induced / Q000188:drug therapy; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D004938:Esophageal Neoplasms / Q000188:drug therapy; D005260:Female; D006735:Horseradish Peroxidase / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D008815:Mice, Inbred Strains; D013329:Structure-Activity Relationship; D013662:Tea / Q000737:chemistry; D013755:Tetradecanoylphorbol Acetate / Q000633:toxicity; D018675:Toxicity Tests; D014407:Tumor Cells, Cultured
D000893:Anti-Inflammatory Agents; D044946:Biflavonoids; D013662:Tea; C056068:theaflavin; D016718:Arachidonic Acid; D002392:Catechin; D006735:Horseradish Peroxidase; D013755:Tetradecanoylphorbol Acetate