Molecular Design of Antibrowning Agents

Tyrosinase inhibitory and antioxidant activity of gallic acid and its series of alkyl chain esters were investigated. All inhibited the oxidation of l-3,4-dihydroxyphenylalanine (l-DOPA) catalyzed by mushroom tyrosinase. However, gallic acid and its short alkyl chain esters were oxidized as substrat...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2000-04, Vol.48 (4), p.1393-1399
Main Authors: Kubo, Isao, Kinst-Hori, Ikuyo, Kubo, Yumi, Yamagiwa, Yoshiro, Kamikawa, Tadao, Haraguchi, Hiroyuki
Format: Article
Language:English
Subjects:
Agaricales - enzymology
Antioxidants - chemical synthesis
Antioxidants - pharmacology
Biological and medical sciences
Drug Design
Food additives
Food industries
Food Preservation
Fundamental and applied biological sciences. Psychology
Gallic Acid - analogs & derivatives
Gallic Acid - chemical synthesis
Gallic Acid - pharmacology
General aspects
Kinetics
Monophenol Monooxygenase - antagonists & inhibitors
Oxidation-Reduction
Structure-Activity Relationship
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Summary:Tyrosinase inhibitory and antioxidant activity of gallic acid and its series of alkyl chain esters were investigated. All inhibited the oxidation of l-3,4-dihydroxyphenylalanine (l-DOPA) catalyzed by mushroom tyrosinase. However, gallic acid and its short alkyl chain esters were oxidized as substrates yielding the colored oxidation products. In contrast, the long alkyl chain esters inhibited the enzyme activity without being oxidized. This indicates that the carbon chain length is associated with their tyrosinase inhibitory activity, presumably by interacting with the hydrophobic protein pocket in the enzyme. On the other hand, the esters, regardless their carbon chain length, showed potent scavenging activity on the autoxidation of linoleic acid and 1,1-diphenyl-2-p-picryhydrazyl (DPPH) radical, suggesting that the alkyl chain length is not related to the activity. The effects of side-chain length of gallates in relation to their antibrowning activity are studied. Keywords: Tyrosinase inhibitors; antioxidants; antibrowning agents; molecular design; gallic acid; dodecyl gallate
ISSN:0021-8561
1520-5118
DOI:10.1021/jf990926u