Scytalols A, B, C, and D and other modulators of melanin biosynthesis from Scytalidium sp. 36-93.
From submerged cultures of Scytalidium sp. 36-93, ten metabolites were isolated due to their effects on dihydroxynaphthalene (DHN) or DOPA melanin biosynthesis. Four of the compounds, scytalols A (1a), B (1b), C (2) and D (3), are new secondary metabolites, the structures of which were determined by spectroscopy, while the other compounds are known. Scytalols A (1a) and D (3) are selective inhibitors of DHN melanin biosynthesis and exhibit no antifungal or cytotoxic activities. Nectriapyrone, 6-methoxymellein and 4-chloro-6-methoxymellein stimulated the formation of DOPA melanin in B16-F1 melanoma cells in the absence of melanin-stimulating hormone.
Thines
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E
University of Kaiserslautern, Germany.
Anke
H
H
Sterner
O
O
D000818:Animals; D004295:Dihydroxyphenylalanine / Q000031:analogs & derivatives / Q000096:biosynthesis; D005658:Fungi / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D009284:Naphthols / Q000378:metabolism
D006571:Heterocyclic Compounds; D008543:Melanins; D009284:Naphthols; C041660:1,8-dihydroxynaphthalene; D004295:Dihydroxyphenylalanine; C040616:DOPA melanin