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Biotransformation of p ‐Coumaric Acid (=(2 E )‐3‐(4‐Hydroxyphenyl)prop‐2‐enoic Acid) by Momordica charantia Peroxidase
Author(s) -
Liu HaiLi,
Huang XueFeng,
Wan Xiang,
Kong LingYi
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790111
Subject(s) - chemistry , peroxidase , biotransformation , acetone , p coumaric acid , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , enzyme , organic chemistry , biochemistry , ferulic acid
LC/MS 3 ‐Guided biotransformation of p ‐coumaric acid (=(2 E )‐3‐(4‐hydroxyphenyl)prop‐2‐enoic acid; CA) with H 2 O 2 / 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.