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

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Bae JS, Kim TH

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

Bioorg Med Chem Lett. 2012 Jan 15;22(2):793-6. doi: 10.1016/j.bmcl.2011.12.072. Epub 2011 Dec 21.

PubMed ID

22217871 [ View in PubMed

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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.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Celecoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	200	N/A	N/A	Details