Enzymatic transformation of caffeic acid with enhanced cyclooxygenase-2 inhibitory activity.
Convenient enzymatic transformation of the phenylpropanoid caffeic acid (1) with polyphenol oxidase originating from pear afforded three new oxidized metabolites, caffeoxynic acid (2), caffeicinic acid (3), and isocaffeicinic acid (4), along with, 7,8-erythro-caffeicin (5) and phellinsin A (6). The structures of the three new caffeic acid oxidation products were elucidated on the basis of spectroscopic methods. The new products 2 and 3 exhibited significantly enhanced inhibitory activity against cyclooxygenase-2 (COX-2) when compared to parent caffeic acid.
College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu 702-701, Republic of Korea.
Jong-Sup
JS
Bae
Tae Hoon
TH
Kim
D002109:Caffeic Acids / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D051546:Cyclooxygenase 2 / Q000378:metabolism*; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D002109:Caffeic Acids; D052246:Cyclooxygenase 2 Inhibitors; D051546:Cyclooxygenase 2; C040048:caffeic acid