1. Chemical constituents derived from Artocarpus xanthocarpus as inhibitors of melanin biosynthesis.
- Author
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Jin YJ, Lin CC, Lu TM, Li JH, Chen IS, Kuo YH, and Ko HH
- Subjects
- Animals, Antioxidants chemistry, Cell Line, Tumor drug effects, Cell Survival drug effects, Drug Evaluation, Preclinical methods, Enzyme Inhibitors chemistry, Enzyme Inhibitors pharmacology, Flavonoids chemistry, Flavonoids isolation & purification, Flavonoids pharmacology, Melanoma, Experimental drug therapy, Melanoma, Experimental metabolism, Mice, Molecular Structure, Monophenol Monooxygenase antagonists & inhibitors, Monophenol Monooxygenase metabolism, Stilbenes chemistry, Stilbenes metabolism, Antioxidants pharmacology, Artocarpus chemistry, Melanins antagonists & inhibitors, Melanins biosynthesis
- Abstract
Twenty-four compounds, including the previously unknown artoxanthocarpuone A, artoxanthocarpuone B, hydroxylakoochin A, methoxylakoochin A, epoxylakoochin A, and artoxanthol, were isolated and characterized spectroscopically. Among them, artoxanthol is stilbene oligomer presumably constructed in a 5,11,12-triphenyl hexahydrochrysene scaffold by a Diels-Alder type of reaction, for which a biosynthetic pathway is proposed. Artoxanthol, alboctalol, steppogenin, norartocarpetin, resveratrol, oxyresveratrol, and chlorophorin potently inhibited mushroom tyrosinase activity with IC50 values from 0.9 to 5.7 μM that were all far stronger than the positive controls. Artoxanthocarpuone A, artoxanthocarpuone B, methoxylakoochin A, lakoochin A, cudraflavone C, artonin A, resveratrol, and chlorophorin reduced tyrosinase activity and inhibited α-melanocyte-stimulating hormone-induced melanin production in B16F10 melanoma cells without affecting cell proliferation. Collectively, the results suggest that the constituents of Artocarpus xanthocarpus have potential to be used as depigmentation agents., (Copyright © 2015 Elsevier Ltd. All rights reserved.)
- Published
- 2015
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