The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Melanoxazal, New Melanin Biosynthesis Inhibitor Discovered by Using the Larval Haemolymph of the Silkworm, Bombyx mori
Production, Isolation, Structural Elucidation, and Biological Properties
SENJI TAKAHASHIRYUJU HASHIMOTOKUNIKATSU HAMANOTOMOO SUZUKIAKIRA NAKAGAWA
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1996 Volume 49 Issue 6 Pages 513-518

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Abstract

A new melanin biosynthesis inhibitor, melanoxazal, was isolated from the fermentation broth of Trichoderma sp. ATF-451 by successive purification procedures of carbon adsorption, ethyl acetate extraction and silica gel column chromatography. The inhibitor possesses a novel oxazole-containing structure with molecular formula, C8H9NO3. The structure was determined by means of NMR analyses to be (E)-4-(2'-formyl-3'-hydroxybuten-r-yl) oxazole, which is related to melanoxadin. Melanoxazal inhibited melanin formation in the larval haemolymph of the silkworm, Bombyx mori; IC50 value=30.1 μg/ml. Melanoxazal also showed a strong inhibitory activity against mushroom tyrosinase with IC50 value=4.2μg/ml.

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