Scytalols A, B, C, and D and other modulators of melanin biosynthesis from Scytalidium sp. 36-93

J Antibiot (Tokyo). 1998 Apr;51(4):387-93. doi: 10.7164/antibiotics.51.387.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dihydroxyphenylalanine / analogs & derivatives
  • Dihydroxyphenylalanine / biosynthesis
  • Fungi / chemistry*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / isolation & purification
  • Heterocyclic Compounds / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Melanins / biosynthesis*
  • Melanoma, Experimental / metabolism
  • Mice
  • Molecular Structure
  • Naphthols / metabolism

Substances

  • Heterocyclic Compounds
  • Melanins
  • Naphthols
  • 1,8-dihydroxynaphthalene
  • Dihydroxyphenylalanine
  • DOPA melanin