Article

Enzymatic transformation of caffeic acid with enhanced cyclooxygenase-2 inhibitory activity.

College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu 702-701, Republic of Korea.
Bioorganic & medicinal chemistry letters (impact factor: 2.65). 12/2011; 22(2):793-6. DOI:10.1016/j.bmcl.2011.12.072 pp.793-6
Source: PubMed

ABSTRACT 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.

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Keywords

3 exhibited
 
7,8-erythro-caffeicin
 
caffeicinic acid
 
Convenient enzymatic transformation
 
cyclooxygenase-2
 
inhibitory activity
 
isocaffeicinic acid
 
new oxidized metabolites
 
parent caffeic acid
 
phenylpropanoid caffeic acid
 
polyphenol oxidase originating
 
structures
 
three new caffeic acid oxidation products
 

Jong-Sup Bae