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KMID : 1134820150440121912
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Journal of the Korean Society of Food Science and Nutrition
2015 Volume.44 No. 12 p.1912 ~ p.1917
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Secondary Metabolites from Enzymatic Oxidation of Caffeic Acid with Pancreatic Lipase Inhibitory Activity
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Kim Tae-Hoon
Kim Myiung-Kwon
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Abstract
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Pancreatic lipase is a potential therapeutic target for the treatment of diet-induced obesity in humans. As part of our continuing search for novel bioactive compounds, the convenient enzymatic transformation of caffeic acid into neolignans as well as related oxidized-products enhanced pancreatic lipase inhibitory activity. Enzymatic transformation of caffeic acid (1) using polyphenol oxidase originating from Korean pear yielded four oxidized metabolites, which were identified by different spectroscopic techniques (1H,13C NMR, DEP/T, 1H－1H COSY, HMBC, HMQC, and NOESY). The anti-obesity efficacy of caffeic acid reactant was tested by in vitro porcine pancreatic lipase assay. All tested samples showed dose-dependent pancreatic lipase inhibitory activities. Four oxidative products including phellinsin A (2), caffeicinic acid (3), isocaffeicinic acid (4), and 7,8-erythro-caffeicin (5) were isolated and identified. The major metabolites (2～5) were evaluated for their pancreatic lipase inhibitory activity, and oxidized-products (2 ～3) improved potency against pancreatic lipase when compared to original caffeic acid. This result suggested that the neolignans isolated from oxidative transformation of caffeic acid might be beneficial in the treatment of obesity and relevant diseases, and the convenient enzymatic transformation by polyphenol oxidase may be a valuable method for structural modification and enhancement of activity.
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KEYWORD
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enzymatic transformation, caffeic acid, neolignan, obesity, pancreatic lipase
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