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Archives of Microbiology

, Volume 142, Issue 3, pp 234–241 | Cite as

Melanin biosynthesis and the metabolism of flaviolin and 2-hydroxyjuglone inWangiella dermatitidis

  • Michael H. Wheeler
  • Robert D. Stipanovic
Original Papers

Abstract

Melanin biosynthesis in the human pathogenWangiella dermatitidis was inhibited by tricyclazole, causing pentaketide melanin metabolites to accumulate in the cultures. One of these metabolites, scytalone, was racemic and thus different than the (+)-enantiomer fromVerticillium dahliae. An albino mutant ofW. dermatitidis metabolized scytalone to a pigment ultrastructurally identical to wild-type melanin. Cell-free homogenates of the wild type carried out typical reductive and dehydrative reactions with known melanin intermediates and the reductive reactions were inhibited by tricyclazole. Other reductive and dehydrative reactions that utilize flaviolin and 2-hydroxyjuglone were studied anaerobically with homogenates from both the wild type and the albino mutant. The homogenates converted flaviolin to 5-hydroxyscytalone and products identical to those obtained from 2-hydroxyjuglone. The albino, in culture, carried out the same reactions with 2-hydroxyjuglone but metabolized flaviolin to a number of unknown colored products apparently through oxidative reactions. Similarities between the melanin pathway and the flaviolin and 2-hydroxyjuglone branch pathways are discussed and tricyclazole is shown to inhibit reductive reactions with naphthols in the three pathways.

Key words

Chromoblastomycosis Enzymes Flaviolin 2-Hydroxyjuglone Melanin Metabolism Pathogen Pigments Tricyclazole Wangiella dermatitidis 

Abbreviations

DHN

dihydroxynaphtalene

HJ

hydroxyjuglone

THT

trihydroxytetralone

THN

trihydroxynaphthalene or tetrahydroxynaphthalene

DTT

dithiothreitol

HS

hydroxyscytalone

PHN

pentahydroxynaphthalene

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References

  1. Aldridge DC, Davies AB, Jackson MR, Turner WB (1974) Pentaketide metabolites of the fungusPhialophora lagerbergii. J Chem Soc Perkin Trans I 1974:1540–1541Google Scholar
  2. Bell AA, Stipanovic RD, Puhalla JE (1976) Pentaketide metabolites ofVerticillium dahliae: Identification of (+)-scytalone as a natural precursor to melanin. Tetrahedron 32:1353–1356Google Scholar
  3. Geis PA, Szaniszlo PJ (1984) Carotenoid pigments of the dematiaceus fungusWangiella dermatitidis. Mycologia 76: 268–273Google Scholar
  4. Geis PA, Wheeler MH, Szaniszlo PJ (1984) Pentaketide metabolites of melanin synthesis in the dematiaceous fungusWangiella dermatitidis. Arch Microbiol 137:324–328Google Scholar
  5. Harborne JB (1982) Introduction to ecological biochemistry. Academic Press Inc. New York, pp 210–212Google Scholar
  6. Iwasaki S, Muro H, Nozoe S, Okuda S, Sato Z (1972) Isolation of 3,4-dihydro-3,4,8-trihydroxy-1(2H) naphthalenone and tenuazonic acid fromPyricularia oryzae Cavara. Tetrahedron Lett 1972:13–16Google Scholar
  7. Iwasaki S, Muro H, Sasaki K, Sasaki K, Nozoe S, Okuda S, Sato Z (1973) Isolation of phytotoxic substances produced byPyricularia oryzae Cavara. Tetrahedron Lett 1973:3537Google Scholar
  8. Kubo Y, Suzuki K, Furusawa I, Yamamoto M (1983) Scytalone as a natural intermediate of melanin biosynthesis in appressoria ofColletotrichum lagenarium. Exp Mycol 7:208–215Google Scholar
  9. Rippon JW (1982) Medical mycology. Saunders Company, PhiladelphiaGoogle Scholar
  10. Sankawa U, Shimada H, Sato T, Kinoshita T, Yamasaki K (1981) Biosynthesis of scytalone. Chem Pharm Bull 29(12):3536–3542Google Scholar
  11. Singh H, Folk TL, Scheuer PJ (1969) Synthesis of juglone derivatives: hydroxyl, acetyl and ethyl substituents. Tetrahedron Lett 1969:5301–5310Google Scholar
  12. Soga O (1982) Stimulative production of flaviolin byPhoma wasabiae. Agric Biol Chem 46:1061–1063Google Scholar
  13. Stewart TE, Plummer EL, McCandless LL, West JR, Silverstein RM (1977) Determination of enantiomer composition of several bicyclic ketal insect pheromone components. J Chem Ecol 3:27–43Google Scholar
  14. Stipanovic RD, Bell AA (1977) Pentaketide metabolites ofVerticillium dahliae. II. Accumulation of naphthol derivatives by the aberrant-melanin mutantbrm-2. Mycologia 69:164–172Google Scholar
  15. Sussman AS (1968) Longevity and survivability of fungi. In: Ainsworth GC, Sussman AS (eds) The fungi, vol 3. Academic Press Inc. New York, pp 447–486Google Scholar
  16. Szaniszlo PJ, Geis PA, Jacobs CW, Cooper CR, Harris JL (1983) Cell wall changes associated with yeast-to-multicellular form conversion inWangiella dermatitidis. In: Schlessinger D (ed) Microbiology, vol 83. American Society for Microbiology, Washington, DC, pp 239–244Google Scholar
  17. Tokousbalides MC, Sisler HD (1978) Effect of tricyclazole on growth and secondary metabolism inPyricularia oryzae. Pest Biochem Physiol 8: 26–32Google Scholar
  18. Tokousbalides MC, Sisler HD (1979) Site of inhibition by tricyclazole in the melanin biosynthetic pathway ofVerticillium dahliae. Pest Biochem Physiol 11:64–73Google Scholar
  19. Wheeler MH (1981) Melanin biosynthetic enzymes in cell-free homogenates ofVerticillium dahliae andPyricularia oryzae. Phytophatology 71:912 (Abstract)Google Scholar
  20. Wheeler MH (1982) Melanin biosynthesis inVerticillium dahliae: dehydration and reduction reactions in cell-free homogenates. Exp Mycol 6:171–179Google Scholar
  21. Wheeler MH (1983) Comparisons of fungal melanin biosynthesis in ascomycetous, imperfect and basidiomycetous fungi. Trans Br Mycol Soc 81:29–36Google Scholar
  22. Wheeler MH, Stipanovic RD (1979) Melanin biosynthesis inThielaviopsis basicola. Exp Mycol 3:340–350Google Scholar
  23. Wheeler MH, Tolmsoff WJ, Meola S (1976) Ultrastructure of melanin formation inVerticillium dahliae with (+)-scytalone as a biosynthetic intermediate. Can J Microbiol 22:702–711Google Scholar
  24. Wheeler MH, Tolmsoff WJ, Bell AA (1977) Ultrastructure of melanin formation inCurvularia sp.,Alternaria sp., andDrechslera sorokiniana. In: Proceedings of the 35th Annual Meeting of the Electron Microscopy Society of America, Boston, pp 398–399Google Scholar
  25. Wheeler MH, Tolmsoff WJ, Bell AA, Mollenhauer HH (1978) Ultrastructure and chemical distinction of melanins formed byVerticillium dahliae from (+)-scytalone, 1,8-dihydroxynaphthalene, catechol andl-3,4-dihydroxyphenylalanine. Can J Microbiol 24:289–297Google Scholar
  26. Wolkow PM, Sisler HD, Vigil EL (1983) Effect of inhibitors of melanin biosynthesis on structure and function of appressoria ofColletotrichum lindemuthianum. Phys Plant Path 23:55–71Google Scholar
  27. Woloshuk CP, Sisler HD, Tokousbalides MC, Dutky SR (1980) Melanin biosynthesis inPyricularia oryzae: site of tricyclazole inhibition and pathogenicity of melanin-deficient mutants. Pest Biochem Physiol 14:256–264Google Scholar
  28. Woloshuk CP, Sisler HD, Vigil EL (1983) Action of the antipenetrant, tricyclazole, on appressoria ofPyricularia oryzae. Phys Plant Path 22:245–259Google Scholar
  29. Yamaguchi I, Sekido S, Misato T (1982) The effect of non-fungicidal anti-blast chemicals on the melanin biosynthesis and infection byPyricularia oryzae. J Pest Sci 7:523–529Google Scholar

Copyright information

© Springer-Verlag 1985

Authors and Affiliations

  • Michael H. Wheeler
    • 1
  • Robert D. Stipanovic
    • 1
  1. 1.National Cotton Pathology Research LaboratoryCollege StationUSA

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