Biotransformation of p-Coumaric Acid (=(2E)-3-(4-Hydroxyphenyl)prop-2-enoic Acid) by Momordica charantia Peroxidase

• Published in: Helvetica chimica acta Vol. 90; no. 6; pp. 1117 - 1132
• Main Authors: Liu, Hai-Li, Huang, Xue-Feng, Wan, Xiang, Kong, Ling-Yi
• Format: Journal Article
• Language: English
• Published: Zürich WILEY-VCH Verlag 01.06.2007; WILEY‐VCH Verlag; Wiley
• Subjects: Antioxidants; Biotransformation; Chemistry; Chemistry, Multidisciplinary; Momordica charantia peroxidase; p-Coumaric acid; Physical Sciences; Science & Technology; OXIDATION; DECARBOXYLASE; METABOLISM; GENE; FERULIC ACID; PURIFICATION
• ISSN: 0018-019X; 1522-2675
• DOI: 10.1002/hlca.200790111

LC/MS3‐Guided biotransformation of p‐coumaric acid (=(2E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoic acid; CA) with H2O2/Momordica charantia peroxidase at pH 5.0 and 45° in the presence of acetone has resulted in the isolation of three CA trimers, triCA1 (1), triCA2 (trans‐2), and triCA3 (cis‐2), and seven CA dimers, diCA1–diCA7, i.e., 3–9, among which seven (triCA1–triCA3 and diCA1–diCA4) are new compounds and three (diCA5–diCA7) are known compounds. The structures were established by 2D‐NMR such as HSQC, HMBC, and NOESY measurements. The possible mechanism for the formation of the products is also discussed (Schemes 1–3). This is the first time that the biotansformation of p‐coumaric acid catalyzed by peroxidase in vitro was achieved. Compounds triCA3 (cis‐2), diCA1 (3), diCA5 (7), and diCA7 (9) exhibit a stronger antioxidative activity than the parent CA.