Melanoxazal, new melanin biosynthesis inhibitor discovered by using the larval haemolymph of the silkworm, Bombyx mori. Production, isolation, structural elucidation, and biological properties.
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-1'-yl) oxazole, which is related to melanoxadin. Melanoxazal inhibited melanin formation in the larval haemolymph of the silkworm, Bombyx mori; IC50 value = 30.1 micrograms/ml. Melanoxazal also showed a strong inhibitory activity against mushroom tyrosinase with IC50 value = 4.2 micrograms/ml.
Takahashi
S
S
Department of Bioscìences, Teikyo University, Utsunomiya, Japan.
Hashimoto
R
R
Hamano
K
K
Suzuki
T
T
Nakagawa
A
A
D000818:Animals; D012831:Bombyx; D005285:Fermentation; D008543:Melanins / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014242:Trichoderma
D008543:Melanins; D010080:Oxazoles; C100695:melanoxazal