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

Jong Sup Bae; Tae Hoon Kim

doi:10.1016/j.bmcl.2011.12.072

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

Jong Sup Bae, Tae Hoon Kim

Daegu Haany University

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

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.

Original language	English
Pages (from-to)	793-796
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2011.12.072
State	Published - 15 Jan 2012

Keywords

Anti-inflammation
Caffeic acid oxidation
Cyclooxygenase-2
Enzymatic transformation
Neolignan

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10.1016/j.bmcl.2011.12.072

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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.",

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AB - 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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KW - Caffeic acid oxidation

KW - Cyclooxygenase-2

KW - Enzymatic transformation

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

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Keywords

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