Skip to main content

Melanins and Their Importance in Pathogenic Fungi

  • Chapter
Current Topics in Medical Mycology

Part of the book series: Current Topics in Medical Mycology ((CT MYCOLOGY,volume 2))

Abstract

Melanins are generally described as dark brown or black pigments of high molecular weight formed by oxidative polymerization of phenolic compounds. Certain yellow, red, green, purple, or blue pigments have similar chemical structures and occasionally are referred to as types of melanins. Melanins are found in humans and various other warm- and cold-blooded vertebrates; invertebrates, including insects; higher plants; fungi; and bacteria, including actinomycetes. Most animal melanins are synthesized by tyrosinase, whereas a number of less specific polyphenol oxidases may form melanins in various cellular and extracellular environments of other organisms. In some cases melanins are autoxidative products made in the absence of enzymes.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Ajello L, Iger M, Wybel R, Vigil FJ: Drechslera rostrata as an agent of phaeohyphomycosis. Mycologia 82:1094–1102, 1980.

    Google Scholar 

  2. Al-Doory Y: The infrastructure of Cryptococcus neoformans. Sabouraudia 9:113–118,1971.

    Google Scholar 

  3. Aldridge DC, Davies AB, Jackson, MR, Turner WB: Pentaketide metabolites of the fungus Phialophora lagerbergii. J Chem Soc Perkin Trans 1:1540–1541, 1974.

    Google Scholar 

  4. Allport DC, Bu’Lock JD: Biosynthetic pathways in Daldinia concentrica. J Chem Soc Part I, 654–662, 1960.

    Google Scholar 

  5. Araki F, Miyagi Y: Effects of fungicides on penetration by Pyricularia oryzae as evaluated by an improved cellophane method. J Pesticide Sci 2:457–461,1977.

    CAS  Google Scholar 

  6. Arnone A, Camarda L, Nasini G: Secondary mould metabolites. Part 13. Fungal perylenequinones: Phleichrome, isophleichrome, and their endoperoxides. J Chem Soc Perkin Trans 1:1387–1392, 1985.

    Google Scholar 

  7. Arnone A, Nasini G, Merlini L, Assante G: Secondary mould metabolites. Part 16. Stemphylotoxins. New reduced perylenequinone metabolites from Stemphylium botryosum var. lactucum . J Chem Soc Perkin Trans 1:525–530, 1986.

    Google Scholar 

  8. Assante G, Locci R, Camarda L, Merlini L, Nasini G: Screening of the genus Cercospora for secondary metabolites. Phytochemistry 16:243–247, 1977.

    CAS  Google Scholar 

  9. Astill BD, Roberts JC: Studies in mycological chemistry. Part I. Flaviolin, 2 (or 3):5:7-trihydroxy-l:4-naphthaquinone, a metabolic product of Aspergillus citricus (Wehmer) Mosseray. J Chem Soc Part 3, 3302–3307, 1953.

    Google Scholar 

  10. Bardshiri E, Simpson TJ: 13C and 2H labelling studies on the biosynthesis of scytalone in Phialophora lagerbergii. Tetrahedron 39:3539–3542, 1983.

    CAS  Google Scholar 

  11. Bartsch E, Lerbs W, Luckner M: Phenol oxidase activity and pigment synthesis in conidiospores of Pencillium cudopium. Z Allg Mikrobiol 19:75–82, 1979

    PubMed  CAS  Google Scholar 

  12. Bell AA: Biochemical mechanisms of disease resistance. Ann Rev Plant Physiol 32:21–81, 1981.

    CAS  Google Scholar 

  13. Bell AA, Puhalla, JE, TolmsoffWJ, Stipanovic RD: Use of mutants to establish (+ )-scytalone as an intermediate in melanin biosynthesis by Verticillium dahliae. Can J Microbiol 22:787–799, 1976.

    PubMed  CAS  Google Scholar 

  14. Bell AA, Stipanovic RD, Puhalla JE: Pentaketide metabolites of Verticillium dahliae: Identification of (+ )-scytalone as a natural precursor to melanin. Tetrahedron 32:1353–1356, 1976.

    CAS  Google Scholar 

  15. Bell AA, Wheeler MH: Biosynthesis and functions of fungal melanins. Ann Rev Phytopathol 24:411–451, 1986.

    CAS  Google Scholar 

  16. Bellinck C: Chemical study of Penicillium and Trichoderma pigments. Ann Microbiol 2:131–142, 1975.

    Google Scholar 

  17. Beneke ES, Rogers AL: Medical Mycology Manual with Human Mycoses Monograph, (4th ed). Minneapolis, Burgess Publishing, 1980.

    Google Scholar 

  18. Benes SE, Ritchie DF: Evidence for increased malanin content in dicarboximideresistant strains of Moniliniafructicola. Phytopathology 74 (abstract A697): 877, 1984.

    Google Scholar 

  19. Benitez T, Villa TG, Acha IG: Some chemical and structural features of the conidial wall of Trichoderma viride. Can J Microbiol 22:318–321, 1976.

    PubMed  CAS  Google Scholar 

  20. Beresky MA, Hall DW: The influence of phenylthiourea on encapsulation, melanization, and survival in larvae of the mosquito Aedes aegypti parasitized by the nematode Neoaplectana carpocapsae. J Invert Pathol 29:74–80, 1977.

    CAS  Google Scholar 

  21. Blois MS Jr: Physical studies of the melanins, In Kawamura T, Fitzpatrick TB, Seiji M (eds): Biology of Normal and Abnormal Melanocytes. Tokyo, University of Tokyo Press, 1971, 125–139.

    Google Scholar 

  22. Blois MS Jr: The melanins: Their synthesis and structure. Photochem Photobiol Rev 3:115–134, 1978.

    CAS  Google Scholar 

  23. Blois MS Jr, Taskovich L: The reversible binding of some aromatic and cyclic compounds to biopolymers in vitro. J Invest Dermatol 53:344–350, 1969.

    PubMed  CAS  Google Scholar 

  24. Bloomfield BJ, Alexander M: Melanins and resistance of fungi to lysis. J Bacteriol 93:1276–1280, 1967.

    PubMed  CAS  Google Scholar 

  25. Boekelheide K, Graham DG, Mize PD, Anderson CW, Jeffs PW: Synthesis of y-L-Glutaminyl-[3,5-3H] 4-hydroxybenzene and the study of reactions catalyzed by the tyrosinase of Agaricus bisporus. J Biol Chem 254:12185–12191, 1979.

    PubMed  CAS  Google Scholar 

  26. Buchenauer H, Zeun R, Schinzer U: Effect of tricyclazole on mycelium growth as well as on development and pigmentation of scelorotia of Sclerotinia sclerotiorum. Z Pflanzenkr Pflanzenschutz 92:17–26, 1985.

    CAS  Google Scholar 

  27. Bull AT: Chemical composition of wild-type and mutant Aspergillus nidulans cell walls. The nature of polysaccharide and melanin constituents. J Gen Microbiol 63:75–94, 1970.

    PubMed  CAS  Google Scholar 

  28. Bull AT: Kinetics of cellulase inactivation by melanin. Enzymologia 39:333–347, 1970.

    PubMed  CAS  Google Scholar 

  29. Bull AT: Inhibition of polysaccharases by melanin: Enzyme inhibition in relation to mycolysis. Arch Biochem Biophys 137:345–356, 1970.

    PubMed  CAS  Google Scholar 

  30. Bull AT, Carter BLA: The isolation of tyrosinase from Aspergillus nidulans, its kinetic and molecular properties and some consideration of its activity in vivo. J Gen Microbiol 75:61–73, 1973.

    PubMed  CAS  Google Scholar 

  31. Bu’Lock, J: Essays in Biosynthesis and Microbial Development. New York, Wiley and Sons, 1967. 3la. Bustamam M, Sisler HD: Effect of pentachloronitrobenzene, pentachloroaniline and albinism on epidermal penetration of appressoria of Pyricularia. Pestle Biochem Physiol (in press).

    Google Scholar 

  32. Butler MJ, Lachance M-A: Quantitative binding of azure A to melanin of the black yeast Phaeococcomyces. Exp My col 10:166–170, 1986.

    CAS  Google Scholar 

  33. Cameron DW, Sidell MD: 1,3,6,8,11,13-Hexachloro-4,10-dihydroxydinaphtho [2,1-6:1 2’-d] furan-5,9-dione. A polychloro quinone from green soils. Aust J Chem 31:1323–1333, 1978.

    CAS  Google Scholar 

  34. Campbell CK, Mulder JL: Skin and nail infection by Scytalidium hyalinum sp. nov. Sabouraudla 15:161–166, 1977.

    CAS  Google Scholar 

  35. Cantino EC, Horenstein EA: The role of ketoglutarate and polyphenol oxidase in the synthesis of melanin during morphogenesis in Blastocladiella emersonii. Physiol Plant 8:189–221, 1955.

    CAS  Google Scholar 

  36. Carley HE, Watson RD, Huber DM: Inhibition of pigmentation in Aspergillus niger by dime thy Isulfoxide. Can J Bot 45:1451–1453, 1967.

    CAS  Google Scholar 

  37. Carter BLA, Bull AT: Studies of fungal growth and intermediary carbon metabolism under steady and non-steady state conditions. Biotechnol Bioeng 11:785–804, 1969.

    Google Scholar 

  38. Chantarakul N: Subcutaneous cystic granuloma due to brown pigmented fungi (subcutaneous chromoblastomycosis) Report of 6 cases. J Med Assoc Thailand 54:953–958, 1971.

    CAS  Google Scholar 

  39. Chaskes S, Edberg SC, Singer JM: A DL-DOPA drop test for the identification of Cryptococcus neoformans. Mycopathologla 74:143–148, 1981.

    CAS  Google Scholar 

  40. Chaskes S, Tyndall RL: Pigment production by Cryptococcus neoformans from para- and ortho-diphenols: Effect of the nitrogen source. J Clln Microblol 1:509–514, 1975.

    CAS  Google Scholar 

  41. Chaskes S, Tyndall RL: Pigment production by Cryptococcus neofomans and other Cryptococcus species from aminophenols and diaminobenzenes. J Clln Microbiol 1:146–152, 1978.

    Google Scholar 

  42. Chaskes S, Tyndall RL: Pigmentation and autofluorescence of Cryptococcus species after growth on tryptophan and anthranilic acid media. Mycopathologia 64:105–112, 1978.

    PubMed  CAS  Google Scholar 

  43. Chavin W: Mechanisms in the control of dermal pigment in fishes, In Fitzpatrick TB, Kukita A, Morikawa A, Seiji M, Sober AJ, Toda K (eds): Biology and Disease of Dermal Pigmentation. Tokyo, University of Tokyo Press, 1981, 345–362.

    Google Scholar 

  44. Chet I, Henis Y: Effect of catechol and disodium EDTA on melanin content of hyphal and sclerotial walls of Sclerotlum rolfsll Sacc. and the role of melanin in the susceptibility of these walls to β-(1,3)-glucanase and chitinase. Soil Biol Biochem 1:131–138, 1969.

    CAS  Google Scholar 

  45. Chida T, Sisler HD: Restoration of appressorial penetration ability with melanin precursors in Pyricularia oryzae treated with antipenetrants and in melanindeficient mutants. J Pesticide Scl 12:49–55, 1987.

    CAS  Google Scholar 

  46. Clutterbuck AJ: Absence of laccase from yellow-spored mutants of Aspergillus nldulans. J Gen Microbiol 70: 423-435, 1972.

    PubMed  CAS  Google Scholar 

  47. Cooper LA, Gadd GM: Differentiation and melanin production in hyaline and pigmented strains of Mlcrodochlum bolleyl. Antonle van Leeuwenhoek 50:53–62, 1984.

    CAS  Google Scholar 

  48. Corrado ML, Kramer M, Cuirnnings M, Eng RH: Susceptibility of dematiaceous fungi to amphotericin B, miconazole, ketoconazole, flucytosine and rifampin alone and in combination. Sabouraudla 20:109–113, 1982.

    CAS  Google Scholar 

  49. Cutler JE, Swatek FE: Pigment production by Basidlobolus in the presence of tyrosine. Mycologla 61:130–135, 1969.

    CAS  Google Scholar 

  50. Davies JE, King FE, Roberts JC: The structure of flaviolin. Chem Ind No. 36, 1110–1111, 1954.

    Google Scholar 

  51. Dixon DM, Polak A: In vitro and in vivo drug studies with three agents of central nervous system phaeohyphomycosis. Chemotherapy 33:129–140, 1987.

    PubMed  CAS  Google Scholar 

  52. Dixon DM, Polak A, Szaniszlo PJ: Pathogenicity and virulence of wild-type and melanin-deficient Wangiella dermatitidis. J Med Vet My col 25:97–106, 1987.

    CAS  Google Scholar 

  53. Dixon DM, Walsh TJ, Salkin IF, Polak A: Dactylaria constricta: Another dematiaceous fungus with neurotropic potential in mammals. J Med Vet My col 25:55–58, 1986.

    Google Scholar 

  54. Doherty MD, Cohen GM, Gant TW, Naish S, Riley PA: Metabolism of 1-naphthol by tyrosinase. Biochem Pharmacol 34:3167–3172, 1985.

    CAS  Google Scholar 

  55. Duckworth HW, Coleman JE: Physicochemical and kinetic properties of mushroom tyrosinase. J Biol Chem 245:1613–1625, 1970.

    PubMed  CAS  Google Scholar 

  56. Durrell LW: The composition and structure of walls of dark fungus spores. Mycopathol My col Appl 23:339–345, 1964.

    Google Scholar 

  57. Edberg SC, Chaskes SJ, Alture-Werber E, Singer JM: Esculin-based medium for isolation and identification of Cryptococcus neoformans. J Clin Microbiol 12:332–335, 1980.

    PubMed  CAS  Google Scholar 

  58. Ellis DH, Griffiths DA: The location and analysis of melanins in the cell walls of some soil fungi. Can J Microbiol 20:1379–1386, 1974.

    CAS  Google Scholar 

  59. Ellis DH, Griffiths DA: Melanin deposition in the hyphae of a species of Phomopsis. Can J Microbiol 21:442–452, 1975.

    PubMed  CAS  Google Scholar 

  60. Farmer SG, Komorowski RA: Cutaneous microabscess formation from Alternaria alternata. Am J Clin Pathol 66:565–569, 1976.

    PubMed  CAS  Google Scholar 

  61. Filip Z, Haider K, Beutelspacher H, Martin JP: Comparisons of IR-spectra from melanins of microscope soil fungi, humic acids and model phenol polymers. Geoderma 11:37–52, 1974.

    CAS  Google Scholar 

  62. Findlay GH, Vismer HF: Black grain mycetoma. A study of the chemistry, formation and significance of the tissue grain in Madurella mycetomi infection. Br J Dermatol 91:297–303, 1974.

    PubMed  CAS  Google Scholar 

  63. Findlay GH, Vismer HF, Liebenberg NvdW: Black grain mycetoma: The ultrastructure of Madurella mycetomi . Mycopathologia 67:51–54, 1979.

    PubMed  CAS  Google Scholar 

  64. Findlay JA, Kwan D: Metabolites from a Scytalidium species. Can J Chem 51:3299–3301, 1973.

    CAS  Google Scholar 

  65. Findlay JA, Kwan D: Scytalone (3,6,8-trihydroxytetralone), a metabolite from a Scytalidium species. Can J Chem 51:1617–1619, 1973.

    CAS  Google Scholar 

  66. Fitzpatrick TB, Kukita A, Morikawa F, Seiji M, Sober AJ, Toda K, (eds): Biology and Diseases of Dermal Pigmentation. Tokyo, University of Tokyo Press, 1981.

    Google Scholar 

  67. Fitzpatrick TB, Lerner AB, Nordlund JJ, Anderson RR, Szabo G, et al: Introduction to dermal pigment biology and dermal pigmentary disorders (Ceruloderma): Significance, physical basis, cytologic and biochemical basis, In Fitzpatrick TB et al (eds): Biology and Diseases of Dermal Pigmentation. Tokyo, University of Tokyo Press, 1981, 3–18.

    Google Scholar 

  68. Fleming WH, Hopkins JM, Land GA: New culture medium for the presumptive identification of Candida albicans and Cryptococcus neoformans. J Clin Microbiol 5:236–243, 1977.

    PubMed  CAS  Google Scholar 

  69. Fling M, Horowitz NH, Heinemann SF: The isolation and properties of crystalline tyrosinase from Neurospora. J Biol Chem 238:2045–2052, 1963.

    PubMed  CAS  Google Scholar 

  70. Friis J, Ottolenghi P: Pigment formation by the "black yeast" Phialophora jeanselmii. Antonie van Leeuwenhoek Yeast Symp 35(suppl):H13–14, 1969.

    Google Scholar 

  71. Fromtling RA, Shadomy HJ, Jacobson ES: Decreased virulence in stable, acapsular mutants of Cryptococcus neoformans. Mycopathologia 79:23–29, 1982.

    PubMed  CAS  Google Scholar 

  72. Fuste FJ, Ajello L, Threlkeld R, Henry JE Jr: Drechslera hawatiensis: Causative agent of a fatal fungal meningo-encephalitis. Sabouraudia 11:59–63, 1973.

    PubMed  CAS  Google Scholar 

  73. Gadd GM: Melanin production and differentiation in batch cultures of the polymorphic fungus, Aureobasidium pullulans . FEMS Microbiol Lett 9:237–240, 1980.

    CAS  Google Scholar 

  74. Gafoor A, Heale JB: Melanin formation and peroxidase activity in Verticillium. Microbios3:87–95, 1971.

    PubMed  CAS  Google Scholar 

  75. Garau J, Diamond RD, Lagrotteria LB, Kabins SA: Alternaria osteomyelitis. Ann Intern Med 86:747–748, 1977.

    PubMed  CAS  Google Scholar 

  76. Geis PA, Szaniszlo PJ: Carotenoid pigments of the dematiaceous fungus Wangiella dermatitidis. Mycologia 76:268–273, 1984.

    CAS  Google Scholar 

  77. Geis PA, Wheeler MH, Szaniszlo PJ: Pentaketide metabolites of melanin synthesis in the dematiaceous fungus Wangiella dermatitidis. Arch Microbiol 137:324–328,1984.

    PubMed  CAS  Google Scholar 

  78. Gentles JC, Evans EG: Infection of the feet and nails with Hendersonula toruloidea. Sabouraudia 8:72–75, 1970.

    PubMed  CAS  Google Scholar 

  79. Gerber NN, Wieclawek B: The structures of two naphthoquinone pigments from an actinomycete. J Org Chem 31:1496–1498, 1966.

    PubMed  CAS  Google Scholar 

  80. Geremia E, Corsaro C, Bonomo R: Eumelanins as free radicals trap and superoxide dismutase activities in amphibia. Comp Biochem Physiol 79:67–69, 1984.

    Google Scholar 

  81. Ghani HM, Lancaster JH, Larsh HW: Genetic analysis of pigmentation in Arthroderma benhamiae. J Gen Microbiol 84:205–208, 1974.

    PubMed  CAS  Google Scholar 

  82. Gordon MA, Salkin IF, Stone WB: Phoma (Peyronellaea) as zoopathogen. Sabouraudia 13:329–333, 1975.

    PubMed  CAS  Google Scholar 

  83. Greenblatt GA, Wheeler MH: HPLC analysis of fungal melanin intermediates and related metabolites. J Liquid Chromatogr 9:971–981, 1986.

    CAS  Google Scholar 

  84. Haars A, Huttermann A: Function of laccase in the white-rot fungus Fomes annosus. Arch Microbiol 125:233–237, 1980.

    CAS  Google Scholar 

  85. Ha-Huy-Ke, Luckner M: Structure and function of the conidiospore pigments of Pencillium cyclopium. Z Allg Mikrobiol 19:117–122, 1979.

    PubMed  CAS  Google Scholar 

  86. Haider K, Martin JP: Synthesis and transformation of phenolic compounds by Epicoccum nigrum in relation to humic acid formation. Soil Sci Soc Am Proc 31:766–771, 1967.

    CAS  Google Scholar 

  87. Harris R, Smith RE, Wood TR, Biddle M: Helminthosporium corneal ulcers. Ann Ophthalmol 10:729–733, 1978.

    PubMed  CAS  Google Scholar 

  88. Heale JB, Isaac I: Dark pigment formation in Verticillium albo-atrum. Nature 202:412–413, 1964.

    PubMed  CAS  Google Scholar 

  89. Healy ME, Dillavou CL, Taylor GE: Diagnostic medium containing inositol, urea, and caffeic acid for selective growth of Cryptococcus neformans. J Clin Microbiol 6:387–391, 1977.

    PubMed  CAS  Google Scholar 

  90. Hegnauer H, Nyhlen LE, Rast DM: Ultrastructure of native and synthetic Agaricus bisporus melanins—implications as to the compartmentation of melanogenesis in fungi. Exp My col 9:221–229, 1985.

    CAS  Google Scholar 

  91. Hemingway RW, McGraw GW, Barras SJ: Polyphenols in Ceratocystis minor infected Pinus taeda: Fungal metabolites, phloem and xylem phenols. J Agric Food Chem 25:717–722, 1977.

    CAS  Google Scholar 

  92. Hermann TE, Kurtz MB, Champe SP: Laccase localized in hulle cells and cleistothecial primordia of Aspergillus nidulans. J Bacterial 154:955–964, 1983.

    CAS  Google Scholar 

  93. Hignett RC, Kirkham DS: The role of extracellular melanoproteins of Venturia inaequalis in host susceptability. J Gen Microbiol 48:269–275, 1967.

    PubMed  CAS  Google Scholar 

  94. Hignett RC, Roberts AL, Carder JH: The properties of extracellular enzymes of Venturia inaequalis and their association with loss of virulence of the fungus in culture. J Gen Microbiol 110:67–75, 1979.

    CAS  Google Scholar 

  95. Hignett RC, Roberts AL, Carder JH: Melanoprotein and virulence determinants of Venturia inaequalis. Physiol Plant Pathol 24:321–330, 1984.

    CAS  Google Scholar 

  96. Hironaga M, Watanabe S: Studies on the genera Arthroderma-Trichophyton. Jpn J Med Mycol 18:l6l–168, 1977.

    Google Scholar 

  97. Hollis JP : Studies on Streptomyces scabies. I. Variability in a melanin-indicator medium. Phytopathology 42:273–276, 1952.

    Google Scholar 

  98. Hopfer RL, Blank F: Caffeic acid-containing medium for identification of Cryptococcus neoformans. J Clin Microbiol 2:115–120, 1975.

    Google Scholar 

  99. Hopfer RL, Groschel D: Six-hour pigmentation test for the identification of Cryptococcus neoformans. J Clin Microbiol 2:96–98, 1975.

    Google Scholar 

  100. Horowitz NH, Fling M, Macleod HL, Watanabe Y: Structural and regulative genes controlling tyrosinase synthesis in Neurospora. Cold Spring Harbor Symp Quant Biol 26:233–238, 1961.

    PubMed  CAS  Google Scholar 

  101. Howard DH, Dabrowa N: Mutants of Arthroderma benhamiae. Sabouraudia 17:35–50, 1979.

    PubMed  CAS  Google Scholar 

  102. Hunt GA, Fogel R: Fungal hyphal dynamics in a western Oregon Douglas-fir stand. Soil Biol Biochem 15:641–649, 1983.

    Google Scholar 

  103. Hurst HM, Wagner GH: Decomposition of 14C-labeled cell wall and cytoplasmic fractions rom hyaline and melanic fungi. Soil Sci Soc Am Proc 33:707–711, 1969.

    CAS  Google Scholar 

  104. Ikeda R, Shinoda T, Kagaya K, Fukazawa Y: Role of serum factors in the phagocytosis of weakly or heavily encapsulated Cryptococcus neoformans strains by guinea pig peripheral blood leukocytes. Microbiol Immunol 28:51–61, 1984.

    PubMed  CAS  Google Scholar 

  105. Imshenetsky AA, Lysenko SV, Kazokov GA: Upper boundary of the biosphere. Appl Environ Microbiol 35:1–5, 1978.

    PubMed  CAS  Google Scholar 

  106. Ings RMJ: The melanin binding of drugs and its implications. Drug Metab Rev 15:1183–1212, 1984.

    PubMed  CAS  Google Scholar 

  107. Inoue S, Maeda K, Uematsu T, Kato T: Comparison of tetrachlorophthalide and pentachlorobenzyl alcohol with chlobenthiazone and other melanin inhibitors in the mechanism of rice blast control, J Pesticide Sci 9:731 -761, 1984.

    CAS  Google Scholar 

  108. Ito Y, Nanba H, Kuroda H: Melanin produced by Cochliobolus miyabeanus I. The physical and chemical properties. Yakugaku Zasshi 99:1027–1030, 1979.

    PubMed  CAS  Google Scholar 

  109. Ito Y, Nanba H, Kuroda, H: Melanin produced by Cohliobolus miyabeanus. II. Gas chromatographic-mass spectrometric analysis of the degradation products by alkaline fusion. Yakugaku Zasshi 99:971–975, 1979.

    PubMed  CAS  Google Scholar 

  110. Ivins BE, Holmes RK: Isolation and characterization of melanin-producing (mel) mutants of Vibrio cholerae. Infect Immun 27:721–736, 1980.

    PubMed  CAS  Google Scholar 

  111. Ivins BE, Holmes RK: Factors affecting phaeomelanin production by a melaninproducing (mel) mutant of Vibrio cholerae. Infect Immun 34:895–899, 1981.

    PubMed  CAS  Google Scholar 

  112. Iwasaki S, Muro H, Nozoe S, Okuda S: Isolation of 3,4-dihydro-3,4,8-trihydroxy-l(2H)-naphthalenone and tenuazonic acid from Pyricularia oryzae Cavara. Tetrahedron Lett No. l,13-16, 1972.

    Google Scholar 

  113. Iwasaki S, Muro H, Sasaki K, Nozoe S, Okuda S: Isolations of phytotoxic substances produced by Pyricularia oryzae Cavara. Tetrahedron Lett No. 37, 3537–3542, 1973.

    Google Scholar 

  114. Jackson GVH, Gay JL: Perennation of Sphaerotheca mors-uvae as cleistothecia with particular reference to microbiol activity. Trans Br My col Soc 66:463–471, 1976.

    Google Scholar 

  115. Kaufmann CS, Merz WG: Two rapid pigmentation tests for identification of Cryptococcus neoformans. J Clin Microbiol 15:339–341, 1982.

    PubMed  CAS  Google Scholar 

  116. Kaufman SM: Curvularia endocarditis following cardiac surgery. Am J Clin Pathol 56:466–470, 1971.

    PubMed  CAS  Google Scholar 

  117. Keilin D, Mann T: Polyphenol oxidase: purification, nature and properties. Proc Roy Soc B 125:187–204, 1938.

    CAS  Google Scholar 

  118. Koenigs JW: Production of extracellular hydrogen peroxide and peroxidase by wood-rotting fungi. Phytopathology 62:100–110, 1972.

    CAS  Google Scholar 

  119. Kohno M, Ishizaki H, Lin P-H, Yamamori K, Kunoh H: Effect of polyoxin on fungi. (IX). Ultrastructural and cytochemical analyses of polyoxin-treated hyphae of Alternaria kikuchiana Tanaka. Ann Phytopathol Soc Jpn 49:38–46, 1983.

    CAS  Google Scholar 

  120. Korner A, Pawelek J: Mammalian tyrosinase catalyzes three reactions in the biosynthesis of melanin. Science 217:1163–1165, 1982.

    PubMed  CAS  Google Scholar 

  121. Kozlova TM, Lyakh SP: Morphological and ultrastructural features of the black yeast Nadsoniella nigra var. psychrophilica. Microbiology USSR 50:198–202, 1981.

    Google Scholar 

  122. Krachmer JH, Anderson RL, Binder PS, Waring GO, Rowsey JJ, Meek ES: Helminthosporium corneal ulcers. Am J Ophthalmol 85:666–670, 1978.

    PubMed  CAS  Google Scholar 

  123. Kubo Y, Furusawa I: Localization of melanin in appressoria of Colletotrichum lagenarium. Can J Microbiol 32:280–283, 1986.

    CAS  Google Scholar 

  124. Kubo Y, Suzuki K, Furusawa I, Yamamoto M: Effect of tricyclazole on appressorial pigmentation and penetration from appressoria of Colletotrichum lagenarium. Phytopathology 72:1198–1200, 1982.

    CAS  Google Scholar 

  125. Kubo Y, Suzuki K, Furusawa I, Yamamoto M: Scytalone as a natural intermediate of melanin biosynthesis in appressoria of Colletotrichum lagenarium. Exp Mycol 7:208–2l5, 1983.

    CAS  Google Scholar 

  126. Kubo Y, Suzuki K, Furusawa I, Yamamoto M: Melanin biosynthesis as a prerequisite for penetration by appressoria of Colletotrichum lagenarium: Site of inhibition by melanin-inhibiting fungicides and their action on appressoria. Pestic Biochem Physiol 23:47–55, 1985.

    CAS  Google Scholar 

  127. Kuo M-J, Alexander M: Inhibition of the lysis of fungi by melanins. J Bacteriol 94:624–629, 1967.

    PubMed  CAS  Google Scholar 

  128. Kurtz MB, Champe SP: Dominant spore color mutants of Aspergillus nidulans defective in germination and sexual development. J Bacteriol 148:629–638, 1981.

    PubMed  CAS  Google Scholar 

  129. Kurtz MB, Champe SP: Purification and characterization of the conidial laccase of Aspergillus nidulans. J Bacteriol 151:1338–1345, 1982.

    PubMed  CAS  Google Scholar 

  130. Kwon-Chung KJ, Bennett JE, Rhodes JC: Taxonomic studies on Filobasidiella species and their anamorphs. Antonie van Leeuwenhoek 48:25–38, 1982.

    PubMed  CAS  Google Scholar 

  131. Kwon-Chung KH, Polacheck I, Popkin TJ: Melanin-lacking mutants of Cryptococcus neoformans and their virulence for mice. J Bacteriol 150:1414–1421, 1982.

    PubMed  CAS  Google Scholar 

  132. Kwon-Chung KH, Rhodes JC: Encapsulation and melanin formation as indicators of virulence in Cryptococcus neoformans. Infect Immun 51:218–223, 1986.

    PubMed  CAS  Google Scholar 

  133. Kwon-Chung KJ, Tom WK, Costa JL: Utilization of indole compounds by Cryptococcus neoformans to produce a melanin-like pigment. J Clin Microbiol 18:1419–1421,1983.

    PubMed  CAS  Google Scholar 

  134. Lampert RP, Hutto JH, Donnelly WH, Shulman ST: Pulmonary and cerebral mycetoma caused by Curvularia pallescens. J Pediatr 91:603–605, 1977.

    PubMed  CAS  Google Scholar 

  135. Land GA, Dorn GL, Fleming WH, Beadles TA, Foxworth JH: Isolation and rapid identification of yeasts from compromised hosts. Mycopathologia 65: 123–131, 1978.

    PubMed  CAS  Google Scholar 

  136. Lazarovits G, Stoessl A: Tricyclazole inhibition of melanin and altersolanol A formation in Alternaria solani. Abst 6th Internal Cong of Pestic Chem, Ottawa, 1986,P2F–14.

    Google Scholar 

  137. Lerch K: Neurospora tyrosinase: Structural, spectroscopic and catalytic properties. Mol Cell Biochem 52:125–138, 1983.

    PubMed  CAS  Google Scholar 

  138. Lillie RD: Histochemistry of melanins, In Wolman M (ed):Pigments in Pathology. New York, Academic Press, 1969, 327–351.

    Google Scholar 

  139. Linderman RG, Toussoun TA: Behavior of albino chlamydospores of Thielaviopsis basicola. Phytopathology 56:887, 1966.

    Google Scholar 

  140. Lingappa Y, Sussman AS, Bernstein I A: Effect of light and media upon growth and melanin formation in Aureobasidium pullulans (DeBary) Arn. (= Pullularia pullulans). Mycopathol Mycol Appl 20:109–l28, 1963.

    CAS  Google Scholar 

  141. Linhares LF, Martin JP: Decomposition in soil of the humic acid-type polymers (melanins) ofEurotium echinulatum, Aspergillus glaucus sp. and other fungi. Soil Sci Soc Am J43:738–743, 1978.

    Google Scholar 

  142. Linhares LF, Martin JP: Carbohydrate content of fungal humic acid-type polymers (melanins). Soil Sci Soc Am J43:313–318, 1979.

    CAS  Google Scholar 

  143. Linhares LF, Martin JP: Decomposition in soil of emodin, chrysophanic acid, and a mixture of anthraquinones synthesized by an Aspergillus glaucus isolate. Soil Sci Soc Am J43:940–945, 1979.

    CAS  Google Scholar 

  144. Lockwood JL: Lysis of mycelium of plant-pathogenic fungi by natural soil. Phytopathology 50:787–789, 1960.

    Google Scholar 

  145. Lukiewicz S, Ablewicz E: EPR studies on the radioprotective role of melanins. Radial Res 59:220–221, 1974.

    Google Scholar 

  146. Luther JP, Lipke H: Degradation of melanin by Aspergillus fumigatus. Appl Environ Microbiol 40:145–155, 1980.

    PubMed  CAS  Google Scholar 

  147. Malmstrom BG, Ryden L: The copper-containing oxidases, In Singer TP (ed):Biological Oxidations, New York, Interscience, 1968, 415–438.

    Google Scholar 

  148. Mariat F, Liautaud B, Liautaud M, Marill F-G: Rendersonula toruloidea, agent d’une dermatite verruqueuse mycosique observee en Algerie. Sabouraudia 16:133–140, 1978.

    PubMed  CAS  Google Scholar 

  149. Marr CD: Laccase and tyrosinase oxidation of spot test reagents. Mycotaxon 9:244–276,1979.

    Google Scholar 

  150. Marr CD: Spot tests for detection of tyrosinase. Mycotaxon 19:299–305, 1984.

    Google Scholar 

  151. Marsden CD: Brain melanin, In Wolman M (ed):Pigments in Pathology. New York, Academic Press, 395–420.

    Google Scholar 

  152. Martin JP, Haider K: Phenolic polymers of Stachybotrys atra, Stachybotrys chartarum, and Epicoccum nigrum in relation to humic acid formation. Soil Sci 107:260–270, 1969.

    CAS  Google Scholar 

  153. Martin JP, Haider K: A comparison of the use of phenolase and peroxidase for the synthesis of model humic acid-type polymers. Soil Sci Soc Am J 44:983–988, 1980.

    CAS  Google Scholar 

  154. Martin JP, Haider K, Bondietti E: Properties of model humic acids synthesized by phenoloxidase and autoxidation of phenols and other compounds formed by soil fungi in Proc Int Meet Humic Substances. Pudoc, Nieuwersluis, 1972, 171–186.

    Google Scholar 

  155. Martin JP, Haider K, Linhares LF: Decomposition and stabilization of ring-14C-labeled catechol in soil. Soil Sci Soc Am J43:100–104, 1979.

    CAS  Google Scholar 

  156. Martin JP, Haider K, Wolf D: Synthesis of phenols and phenolic polymers by Hendersonula toruloidea in relation to humic acid formation. Soil Sci Soc Am Proc 36:311–315, 1972.

    CAS  Google Scholar 

  157. Mason HS : The chemistry of melanin. III. Mechanism of the oxidation of dihydroxyphenylalanine by tyrosinase. J Biol Chem 172:83–99, 1948.

    PubMed  CAS  Google Scholar 

  158. Matsumoto T, Padhye AA, Ajello L, Standard PG, McGinnis MR: Critical review of human isolates of Wangiella dermatitidis. Mycologia 76:232–249,1984.

    Google Scholar 

  159. Matsuura K: Effect of melanin synthesis inhibitors on appressorial function in plant pathogenic fungi. J Pesticide Sci 8:379–383, 1983.

    CAS  Google Scholar 

  160. Mayer AM, Harel E: Polyphenol oxidases in plants. Phytochemistry 18:193–215, 1979.

    CAS  Google Scholar 

  161. McGinness J, Corry P, Proctor P: Amorphous semiconductor switching in melanins. Science 183:854–855, 1974.

    Google Scholar 

  162. McGinness JE: Mobility gaps: A mechanism for band gaps in melanins. Science 177:896–897, 1972.

    PubMed  CAS  Google Scholar 

  163. McGinnis MR: Chromoblastomycosis and phaeohyphomycosis: New concepts, diagnosis, and mycology. J Am Acad Dermatol 8:1–16, 1983.

    PubMed  CAS  Google Scholar 

  164. McGinnis MR: Helminthosporium corneal ulcers. Am J Opthalmol 86:853, 1978.

    Google Scholar 

  165. McGinnis MR: Laboratory Handbook of Medical Mycology. New York, Academic Press, 1980.

    Google Scholar 

  166. McGinnis MR, Borelli D, Padhye AA, Ajello L: Reclassification of Cladosporium bantianum in the genus Xylohypha. J Clin Microbiol 23:1148–1151, 1986.

    PubMed  CAS  Google Scholar 

  167. McGinnis MR, Buck DL, Katz B: Paranasal aspergilloma caused by an albino variant of Aspergillusfumigatus. South Med 770:886–888, 1977.

    Google Scholar 

  168. McGinnis MR, Rinaldi MG, Winn RE: Emerging agents of phaeohyphomycosis: Pathogenic species of Bipolaris and Exserohilum. J Clin Microbiol 24: 250–259, 1986.

    PubMed  CAS  Google Scholar 

  169. McGinnis MR, Sorell DF, Miller RL, Kaminski GW: Subcutaneous phaeohyphomycosis caused by Exophiala moniliae. Mycopathologia 73:69–72, 1981.

    PubMed  CAS  Google Scholar 

  170. McGovern EP, Bentley R: Biosynthesis of flaviolin and 5,8-dihydroxy-2,7-dimethoxy-l,4-napthoquinone. Biochemistry 14:3138–3143, 1975.

    PubMed  CAS  Google Scholar 

  171. McGraw GW, Hemingway RW: 6,8-Dihydroxy-3-hydroxymethyl-isocoumarin, and other phenolic metabolites of Ceratocystis minor. Phytochemistry 16:1315–1316, 1977.

    CAS  Google Scholar 

  172. Mekalanos JJ, Sublett RD, Ronig WR: Genetic mapping of toxin regulatory mutations in Vibrio cholerae. J Bacteriol 139:859–865, 1979.

    PubMed  CAS  Google Scholar 

  173. Melezhik AV: Electron tunneling between photo-induced paramagnetic centres in melanin pigment. Biophysics 25:247–251, 1980.

    Google Scholar 

  174. Mendoza CG, Leal JA, Novaes-Ledieu M: Studies of the spore walls ofAgaricus bisporus and Agaricus campestris. Can J Microbiol 25:32–39, 1979.

    PubMed  CAS  Google Scholar 

  175. Menon I A, Persad S, Ranadive NS, Haberman HF: Role of superoxide and hydrogen peroxide in cell lysis during irradiation in vitro of Ehrlich ascitic carcinoma cells in the presence of melanin. Can JBiochem Cell Biol63:278–283, 1985.

    Google Scholar 

  176. Merz WG, Lloyd KO, Silva-Hunter M: Characterization of a Trichophyton mentagrophytes and its diffusible pigment. Sabouraudia 10:86–93, 1972.

    PubMed  CAS  Google Scholar 

  177. Meyers WM, Dooley JR, Kwon-Chung KJ: Mycotic granuloma caused by Phialophora repens. Am J Clin Pathol 64:549–555, 1975.

    PubMed  CAS  Google Scholar 

  178. Mirchink TG, Kashkina GB, Abatwrov YuD: The resistance of fungi with various pigments to y-radiation. Microbiology USSR 41:67–69, 1972.

    Google Scholar 

  179. Morison WL: What is the function of melanin? Arch Dermatol 121:1160–1163, 1985.

    PubMed  CAS  Google Scholar 

  180. Morita T, Aoki H: Isosclerone, a new metabolite of Sclerotinia sclerotiorum (Lib.) De Bary. Agr Biol Chem 38:1501–1505, 1974.

    CAS  Google Scholar 

  181. Nelson RM, Mason HS: Tyrosinase (mushroom), In Tabor H and Tabor CW (eds): Methods in Enzymology, Vol XVIIA. New York, Academic Press, 1970, 626–632.

    Google Scholar 

  182. Nicolaus RA, Piattelli M: Progress in the Chemistry of natural black pigments. Rend Acad Sci Fis Mat Naples Ser 32:83–97, 1965.

    CAS  Google Scholar 

  183. Nicolaus RA, Piattelli M, Fattorusso E: The structure of melanins and melanogenesis-IV: On some natural melanins. Tetrahedron 20:1163–1172, 1964.

    PubMed  CAS  Google Scholar 

  184. Niebauer G: Dendritic cells of human skin, in Experimental and Biological Medicine, Vol. 2. Basel, Karger, 1968.

    Google Scholar 

  185. Nurudeen TA, Ahearn DG: Regulation of melanin production by Cryptococcus neoformans. J Clin Microbiol 10:724–729, 1979.

    PubMed  CAS  Google Scholar 

  186. Okuno T, Kitamura Y, Matsuura K: Mechanism of inhibitory effect of tricyclazole on secondary infection by spores of Pyricularia oryzae. J Pesticide Sci 8:361–362, 1983.

    CAS  Google Scholar 

  187. Okuno T, Matsuura K, Furusawa I: Recovery of appressorial penetration by some melanin precursors in Pyricularia oryzae treated with tricyclazole and in a melanin deficient mutant. J Pesticide Sci 8:357–360, 1983.

    CAS  Google Scholar 

  188. Okuno T, Natsume I, Sawai K, Sawamura K, Furusaki A, Matsumato T: Structure of antifungal and phy to toxic pigments produced by Alternaria spp. Tetrahedron Lett 24:5653–5656, 1983.

    CAS  Google Scholar 

  189. Old KM, Robertson WM: Effects of lytic enzymes and natural soil on the fine structure of conidia of Cochliobolus sativus. Trans Br Mycol Soc 54:343–350, 1970.

    CAS  Google Scholar 

  190. Old KM, Robertson WM: Growth of bacteria within lysing fungal conidia in soil. Trans Br Mycol Soc 54:337–341, 1970.

    Google Scholar 

  191. Omura S: The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis. Bacteriol Rev 40:681–697, 1976.

    PubMed  CAS  Google Scholar 

  192. Paliwal DK, Randhawa HS: A rapid pigmentation test for identification of Cryptococcus neoformans. Antonie van Leeuwenhoek 44:243–246, 1978.

    PubMed  CAS  Google Scholar 

  193. Paliwal DK, Randhawa HS: Evaluation of a simplified Guizotia abyssinica seed medium for differentiation of Cryptococcus neoformans. J Clin Microbiol 7:346–348, 1978.

    PubMed  CAS  Google Scholar 

  194. Pavlenko GV, Loitsyanskaya MS, Nemirovskaya NI: Melanin pigment of Gluconobacter oxydans. Microbiology USSR 50:539–542, 1982.

    Google Scholar 

  195. Pawelek JM, Korner AM: The biosynthesis of mammalian melanin. Am Sci 70:136–145, 1982.

    PubMed  CAS  Google Scholar 

  196. Pechak DG, Crang RE: Observations on melanin synthesis in the black yeast Aureobasidiumpullulans. Micron 10:207–208, 1979.

    Google Scholar 

  197. Piattelli M, Fattorusso E, Magno S, Nicolaus RA: Ustilago melanin, a naturally occurring catechol melanin. Tetrahedron Lett No. 15, 997–998, 1963.

    Google Scholar 

  198. Piattelli M, Fattorusso E, Nicolaus RA, Magno S: The structure of melanins and melanogensis-V. Ustilagomelanin. Tetrahedron 21:3229–3236, 1965.

    CAS  Google Scholar 

  199. Poinar GO: Arthropod immunity to worms, In Jackson GJ, Herman RA, Singer I (eds): Immunity to Parasitic Animals. New York, Appleton-Century-Crofts, 1969, 173–210.

    Google Scholar 

  200. Polacheck I, Hearing VJ, Kwon-Chung KJ: Biochemical studies of phenoloxidase and utilization of catecholamines in Cryptococcus neoformans. J Bacteriol 150:1212–1220, 1982.

    PubMed  CAS  Google Scholar 

  201. Polacheck I, Rosenberger RF: Aspergillus nidulans mutant lacking a-(l,3)-glucan, melanin, and cleistothecia. J Bacteriol 132:650–656, 1977.

    PubMed  CAS  Google Scholar 

  202. Potgieter HJ, Alexander M: Susceptibility and resistance of several fungi to microbial lysis. J Bacteriol 91: 1526–1532, 1966.

    PubMed  CAS  Google Scholar 

  203. Prabhakaran K: Biochemical studies on Mycobacterium leprae. J Basic Microbiol 26:2:117–126, 1986.

    PubMed  CAS  Google Scholar 

  204. Prabhakaran K, Harris EB, Kirchheimer WF: Effect of inhibitors on phenoloxidase of Mycobacterium leprae. J Bacteriol 100:935–938, 1969.

    PubMed  CAS  Google Scholar 

  205. Prabhakaran K, Harris EB, Kirchheimer WF: The nature of the phenolase enzyme in Mycobacterium leprae: Structure-activity relationships of substrates and comparison with other copper proteins and enzymes. Microbios 5:273–281, 1972.

    PubMed  CAS  Google Scholar 

  206. Prabhakaran K, Harris EB, Kirchheimer WF: Hypopigmentation of skin lesions in leprosy and occurrence of 0-diphenoloxidase in Mycobacterium leprae, In Biley V (ed): Pigment Cell, Vol. 3. Basel, Karger, 1976, 152–164.

    Google Scholar 

  207. Prabhakaran K, Harris EB, Kirchheimer WF: Confirmation of the spot test for the identification of Mycobacterium leprae and occurrence of tissue inhibitors of DOPA oxidation. Lepr Rev 48:49–52, 1977.

    Google Scholar 

  208. Prabhakaran K, Harris EB, Kirchheimer WF: Failure to detect o-diphenoloxidase in cultivable mycobacteria obtained from feral armadillos. Lepr Rev 51:341–349, 1980.

    PubMed  CAS  Google Scholar 

  209. Pridham JB, Woodhead S: The biosynthesis of melanin in Alternaria. Phytochemistry 16:903–906, 1977.

    CAS  Google Scholar 

  210. Proctor PH, McGinness JE: The function of melanin. Arch Dermatol 122:507–508, 1986.

    PubMed  CAS  Google Scholar 

  211. Puhalla JE, Bell AA: Genetics and biochemistry of wilt pathogens, In Mace ME, Bell AA, Beckman CH (eds): Fungal Wilt Disease of Plants. New York, Academic, 1981, 145–192.

    Google Scholar 

  212. Pulverer G, Korth H: Cryptococcus neoformans: Pigmentbildung aus verschiedenen polyphenolen. Med Microbiol Immunol 157:46–51, 1971.

    PubMed  CAS  Google Scholar 

  213. Quevedo WC: Physiology of vertebrate pigmentation, In Fitzpatrick TB, et al (eds): Biology and Diseases of Dermal Pigmentation. Tokyo, University of Tokyo Press, 1981, 39–50.

    Google Scholar 

  214. Ramberg JE, McLaughlin DJ: Ultrastructural study of promycelial development and basidiospore initiation in Ustilago maydis. Can J Bot 58:1548–1561, 1980.

    Google Scholar 

  215. Raper KB, Fennell DI: The Genus Aspergillus. Baltimore, Williams and Wilkins, 1965, p 686.

    Google Scholar 

  216. Rast DM, Stussi H, Hegnauer H, Nyhlen LE: Melanins, In Turian G, Hohl HR (eds): The Fungal Spore: Morphogenetic Controls. New York, Academic Press, 1981, 507–531.

    Google Scholar 

  217. Ray AC, Eakin RE: Studies on the biosynthesis of aspergillin by Aspergillus niger. Appl Microbiol 30:909–915, 1975.

    PubMed  CAS  Google Scholar 

  218. Reiss E, Nickerson WJ: Characterization of two melanins produced by Phialophora verrucosa. Sabouraudia 12:193–201, 1971.

    Google Scholar 

  219. Rhodes JC, Howard DH: Isolation and characterization of arginine auxotrophs of Cryptococcus neoformans. Infect Immun 27:910–914, 1980.

    PubMed  CAS  Google Scholar 

  220. Rhodes JC, Polacheck I, Kwon-Chung KJ: Phenoloxidase activity and virulence in isogenic strains of Cryptococcus neoformans. Infect Immun 36:1175–1184, 1982.

    PubMed  CAS  Google Scholar 

  221. Rippon JW: Medical Mycology. The Pathogenic Fungi and the Pathogenic Actinomycetes, (2nd ed). Philadelphia, WB Saunders, 1982.

    Google Scholar 

  222. Rippon JW, Garber D: Dermatophyte infection as a function of mating type and associated enzymes. J Invest Dermatol 53:445–448, 1969.

    PubMed  CAS  Google Scholar 

  223. Robeson D, Strobel G, Matusumoto GK, Fisher EL, Chen MH, Clardy J: Alteichin: An unusual phy to toxin from Alternaria eichorniae, a fungal pathogen of water hyacinth. Experientia 40:1248–1250, 1984.

    PubMed  CAS  Google Scholar 

  224. Rohwedder JJ, Simmons JL, Colfer H, Gatmaitan B: Disseminated Curvularia lunata infection in a football player. Arch Intern Med 139:940–941, 1979.

    PubMed  CAS  Google Scholar 

  225. Rowley BI, Bull AT: Influence of growth rate history on production of melanin by Aspergillus nidulans. Trans Br My col Soc 70:453–455, 1978.

    CAS  Google Scholar 

  226. Ruban EL, Liakh SP, Volkova-Kozlova TM: Nadsoniella nigra mutant synthesizing extracell melanin. Biol Bull Acad Sci USSR 2:283–285, 1969.

    Google Scholar 

  227. Russell JD, Vaughan D, Jones D, Fraser AR: An IR spectroscopic study of soil humin and its relationship to other soil humic substances and fungal pigments. Geoderma 29:1–12, 1983.

    CAS  Google Scholar 

  228. Saiz-Jimenez C, Haider K, Martin JP: Anthraquinones and phenols as inter mediates in the formation of dark colored, humic acid-like pigments by Eurotium echinulatum. Soil Sci Soc Am Proc 39:649–653, 1975.

    CAS  Google Scholar 

  229. Saiz-Jimenez C, Martin F, Cert A: Low bioling-point compounds produced by pyrolysis of fungal melanins and model phenolic polymers. Soil Biol Biochem 11:305–310, 1979.

    CAS  Google Scholar 

  230. Salkin IF, Martinez JA, Kemna ME: Opportunistic infection of the spleen caused by Aureobasidium pullulans. J Clin Microbiol 23:828–831, 1986.

    PubMed  CAS  Google Scholar 

  231. Sankawa U, Shimada H, Sato T, Kinoshita T, Yamasaki K: Biosynthesis of scytalone. Tetrahedron Lett 1977, 483-486.

    Google Scholar 

  232. Sankawa U, Shimada H, Sato T, Kinoshita T, Yamasaki K: Biosynthesis of scytalone. Chem Pharm Bull 29:3536–3542, 1981.

    CAS  Google Scholar 

  233. Schaeffer P: A black mutant ofNeurospora crassa. Mode of action of the mutant allele and action of light on melanogenesis. Arch Biochem Biophys 47:359–379, 1953.

    PubMed  CAS  Google Scholar 

  234. Schnitzer M, Neyroud JA: Further investigations on the chemistry of fungal "humic acids." Soil Biol Biochem 7:365–371, 1975.

    CAS  Google Scholar 

  235. Schonborn C: Dermatophytes with melanoid pigment. 1. Communication: Investigation on the frequency of pigment-forming fungal stains and the intensity of their pigment production. Z Gesamte Hyg Grenzgeb 17:773–778, 1971.

    CAS  Google Scholar 

  236. Schonborn C, Schuhmann P: Dermatophytes with melanoid pigment 2. Communication: contribution on biology of pigment-forming fungal strains. Z Gesamte Hyg Grenzgeb 17:779–784, 1971.

    CAS  Google Scholar 

  237. Seiji M: Biology of dermal melanin, In Fitzpatrick TB, et al (eds): Biology and Diseases of Dermal Pigmentation. Tokyo, Tokyo University Press, 1981, 21–38.

    Google Scholar 

  238. Seredyuk LS, Yurchak LD: Allelopathic effect of melanins of Stachybotrys alternans. Prikl Biokhim Mikrobiol 7:174–177, 1971.

    Google Scholar 

  239. Seto H, Yonehara H: Utilization of 13C-13C coupling in structural and biosynthetic studies. VIII. The cyclization pattern of a fungal metabolite, scytalone. Tetrahedron Lett No. 5, 487–488, 1977.

    Google Scholar 

  240. Shaw CE, Kapica L: Production of diagnostic pigment by phenoloxidase activity of Cryptococcus neoformans. Appl Microbiol 24:824–830, 1972.

    PubMed  CAS  Google Scholar 

  241. Shevtsova VM : Genetics of the cotton wilt pathogen Verticillium dahliae Kleb IV. Complementation analysis of the melanin-deficient mutants of Verticillium dahliae Kleb. Sov Genet 18:1500–1505, 1982.

    Google Scholar 

  242. Shevtsova VM, Kas’yaneko AG, Ten LN, Stepanichenko NN, Samoilov GG: Genetics of the cotton wilt pathogen, Verticillium dahliae Kleb III. Use of biochemical genetic methods to study melanin synthesis in Verticillium dahliae . Sov Genet 18:1391–1401, 1982.

    Google Scholar 

  243. Shevtsova, VM, Ten LN, Stepanichenko NN: Genetical and biochemical studies of melanogenesis in Verticillium tricorpus and Verticillium nigrescens. Genetika 20:1968–1973, 1984.

    CAS  Google Scholar 

  244. Shmyun MP, Zhdanova NM, Svyshchuk AA: Affinity of dark pigment of Oidiodendron cerealis to melanins. Mikrobiol Zh Kiev 37:700–702, 1975.

    Google Scholar 

  245. Siehr DJ: Melanin biosynthesis in Aureobasidium pullulans. J Coat Tech 53:23–25, 1981.

    CAS  Google Scholar 

  246. Simon LT, Bishop DS, Hooper GR: Ultrastructure and cytochemical localization of laccase in two strains of Leptosphaerulina briosiana (Pollaci) Graham and Luttrell. J Bacteriol 137:537–544, 1979.

    PubMed  CAS  Google Scholar 

  247. Simpson TJ: The biosynthesis of polyketides. Nat Prod Rep 1:321–349, 1985.

    Google Scholar 

  248. Sisler HD: Control of fungal diseases by compounds acting as antipenetrants. Crop Prot 5:306–313, 1986.

    CAS  Google Scholar 

  249. Sisler HD, Woloshuk CP, Wolkow PM: Studies on the mode of action of tricyclazole and related compounds, In Lyr H, Polter C (eds): Systemische Fungizide und Antifungale Verbindungen. Berlin, Akademie-Verlag, 1983, 171–176.

    Google Scholar 

  250. Sisler HD, Woloshuk CP, Wolkow PM: Specific chemical regulation of appressorial function. Tagungsber Akad Landwirtschaftswiss. DDR 222:17–28, 1984.

    CAS  Google Scholar 

  251. Sjoblad RD, Minard RD, Bollag JM: Polymerization of 1-naphthol and related phenolic compounds by an extracellular fungal enzyme. Pestic Biochem Physiol 6:457–463, 1976.

    CAS  Google Scholar 

  252. Slawinska D, Slawinski J, Sarna T: Photoinduced luminescence and EPR signals of polyphenol and quinone polymers. Photochem Photobiol 21:393–396, 1975.

    CAS  Google Scholar 

  253. Soga O: Stimulative production of flaviolin by Phoma wasabiae. Agric Biol Chem 46:1061–1063, 1982.

    CAS  Google Scholar 

  254. Sorokin DYu, Bab’eva IP: Lysis of natural yeast populations by soil microorganisms. Microbiology USSR 51:275–278, 1982.

    Google Scholar 

  255. Staib F : Cryptococcus neoformans and Guizotia abyssinica (Syn G. oleifera). Z Hyg Infektionskr 148:466–475, 1962.

    Google Scholar 

  256. Stipanovic RD, Bell AA: Pentaketide metabolites of Verticillium dahliae. 3. Identification of ( —)-3,4-dihydro-3,8-dihydroxy-l(2//)-naphthalenone [( —)-vermelone] as a precursor to melanin. J Org Chem 41:2468–2469, 1976.

    PubMed  CAS  Google Scholar 

  257. Stipanovic RD, Bell A A: Pentaketide metabolites of Verticillium dahliae. II. Accumulation of naphthol derivatives by the aberrant-melanin mutant brm-2 . Mycologia 69:164–172, 1977.

    PubMed  CAS  Google Scholar 

  258. Stipanovic RD, Wheeler MH: Accumulation of 3,3’-biflaviolin, a melanin shunt product, by tricyclazole-treated Thielaviopsis basicola. Pestic Biochem Physiol 13:198–201, 1980.

    CAS  Google Scholar 

  259. Stott DE, Martin JP, Focht DD, Haider K: Biodegradation, stabilization in humus, and incorporation into soil biomass of 2,4-D and chlorocatechol carbons. Soil Sci Soc Am J 41:66–70, 1983.

    Google Scholar 

  260. Strachan AA, Yu RJ, Blank F: Pigment production of Cryptococcus neoformans grown with extracts of Guizotia abyssinica. Appl Microbiol 22:478–479, 1971.

    PubMed  CAS  Google Scholar 

  261. Stussi H, Rast DM: The biosynthesis and possible function of y-glutaminyl-4-hydroxybenzene in Agaricus bisporus. Phytochemistry 20:2347–2352, 1981.

    Google Scholar 

  262. Sussman AS: Longevity and survivability of fungi, In Ainsworth GC, Sussman AS (eds):The Fungi, Vol. 3. New York, Academic Press, 1968, 447–486.

    Google Scholar 

  263. Suzuki K, Kubo Y, Furusawa I, Ishida N, Yamamoto M: Behavior of colorless appressoria in an albino mutant of Colletotrichum lagenarium. Can J Microbiol 28:1210–1213, 1982.

    Google Scholar 

  264. Swan GA: Structure, chemistry, and biosynthesis of the melanins. Fortschr Chem Organ Natur 31:521–582, 1973.

    Google Scholar 

  265. Szaniszlo PJ, Geis PA, Jacobs CW, Cooper CR, Harris JL: Cell wall changes associated with yeast-to-multicellular form conversion in Wangiella dermatitidis, In Schlessinger D (ed): Microbiology, Vol. 83. Washington, American Society for Microbiology, 1983, 239–244.

    Google Scholar 

  266. Tarasov BP, Yurlova NA, Elinov NP: Melanins formed by a culture of Aureobasidium (Pullularid) pullulans Arnaud (DeBary), 1910. Chem Nat Comp (Engl Transl) 216-221, 1977.

    Google Scholar 

  267. Taylor BE, Wheeler MH, Szaniszlo PJ: Evidence for pentaketide melanin biosynthesis in dematiaceous human pathogenic fungi. Mycologia 79:320–322, 1987.

    CAS  Google Scholar 

  268. Taylor RL: A suggested role for the polyphenol-phenoloxidase system in invertebrate immunity. J Invertebr Pathol 14:427–428, 1969.

    PubMed  CAS  Google Scholar 

  269. Ten LN, Otroshchenko OS, Stepanichenko NN, Inoyatova DA: Metabolites of the pathogenic fungus Verticillium dahliae. VII. The phy to toxic pigment PKZh-1 from the culture liquid. Chem Nat Comp (Engl Transl) 572-574, 1977.

    Google Scholar 

  270. Ten LN, Stepanichenko NN, Mukhamedzhanov SZ, Khotyanovich AV: Action of tricyclazole on the biosynthesis of melanin in some fungi of the genus Verticillium. Chem Nat Comp (Engl Transl) 384-385, 1983.

    Google Scholar 

  271. Ten LN, Stepanichenko NN, Shevtsova VM, Mukhamedzhanov SZ, Kas’yanenko AG, Otroshckenko OS: Metabolites of the pathogenic fungus Verticillium dahliae. IX. Pentaketides of mutants and their role in the biosynthesis of melanin. Chem Nat Comp (Engl Transl) 298-302, 1980.

    Google Scholar 

  272. Ten LN, Tyshchenko AA, Stepanichenko NN, Gusakova SD, Mukhamedzhanov SZ, et al: Metabolites of the pathogenic fungus Verticillium dahliae. VI. Pentaketide metabolites and neutral lipids of virulent and a virulent strains. Chem Nat Comp (Engl Transl) 524-527, 1978.

    Google Scholar 

  273. Terreni AA, Morris PR, Di Salvo AF: A red-pigmented strain of Histoplasma capsulatum. Abst 1985 Am Soc Microbiol Ann Meet, p 369.

    Google Scholar 

  274. Tokousbalides MC, Sisler HD: Site of inhibition by tricyclazole in the melanin biosynthetic pathway of Verticillium dahliae. Pestic Biochem Physiol 11:64–73, 1979.

    CAS  Google Scholar 

  275. Tolmsoff WJ, Bell AA, Wheeler MH: Pigment formation from artificial substrates by albino microsclerotia of Verticillium dahliae in relation to melanin synthesis. Proc Beltwide Cotton Prod Res Conf, 1975, 27–28.

    Google Scholar 

  276. Turner WB: Fungal Metabolites. New York, Academic Press, 1971.

    Google Scholar 

  277. Turner WB, Aldridge DC: Fungal Metabolites II. New York, Academic Press, 1983.

    Google Scholar 

  278. Unestam T: Defense reactions in and susceptibility of Australian and New-Guinean fresh water crayfish to European crayfish plague fungus. Aust J Exp Biol Med Sci 53:349–359, 1975.

    Google Scholar 

  279. Uspenskaya GD, Reshetnikova IA, Kozlenko TN: Some characteristics of the pycnidial mucus of fungi from the genera Ascochyta and Phoma. Mikol Fitopatol 14:21–23, 1980.

    Google Scholar 

  280. Vasilevskaya AI, Zhdanova NM, Pokhodenko VD: Character of survival of some gamma irradiated species of dark-colored Hyphomycetes. Mikrobiol Zh 33:438–441, 1970.

    Google Scholar 

  281. Vermeil C, Grodeff A: Blastomycose cheloidienne, a Aureobasidium pullulans. Mycopathologia43:35–39, 1971.

    CAS  Google Scholar 

  282. Vollum DI: Chromomycosis: A review. Br J Dermatol 96:454–458, 1977.

    PubMed  CAS  Google Scholar 

  283. Wang HS, Zeimis RT, Roberts GD: Evaluation of a caffeic acid-ferric citrate test for rapid identification of Cryptococcus neoformans. J Clin Microbiol 6:445–449, 1977.

    PubMed  CAS  Google Scholar 

  284. Wasterstrom S-A: Accumulation of drugs on inner ear melanin. Therapeutic and ototoxic mechanisms. Scand Audiol Suppl 23. Stockholm, Almquist & Wiksell, 1984.

    Google Scholar 

  285. Wheeler MH: Melanin biosynthetic enzymes in cell-free homogenates of Verticillium dahliae and Pyricularia oryzae. Phytopathology 71:912, 1981.

    Google Scholar 

  286. Wheeler MH: Melanin biosynthesis in Verticillium dahliae\ Dehydration and reduction reactions in cell-free homogenates. Exp Mycol6:171-179, 1982.

    Google Scholar 

  287. Wheeler MH: Comparisons of fungal melanin biosynthesis in ascomycetous, imperfect and basidiomycetous fungi. Trans Br My col Soc 81:29–36, 1983.

    CAS  Google Scholar 

  288. Wheeler MH, Stipanovic RD: Melanin biosynthesis in Thielaviopsis basicola. Exp Mycol 3:340–350, 1979.

    CAS  Google Scholar 

  289. Wheeler MH, Stipanovic RD: Melanin biosynthesis and the metabolism of flaviolin and 2-hydroxyjuglone in Wangiella dermatitidis. Arch Microbiol 142:234–241, 1985.

    PubMed  CAS  Google Scholar 

  290. Wheeler MH, Taylor BE, Szaniszlo PJ: Evidence for pentaketide melanin biosynthesis in dematiaceous pathogenic fungi. Abst 1986 Am Soc Microbiol Ann Meet, p 410.

    Google Scholar 

  291. Wheeler MH, Tolmsoff WJ, Bell AA: infrastructure of melanin formation in Curvularia sp., Alternaria sp., and Drechslera sorokiniana. Proc 35th Ann Meet Electron Microsc Soc Am, 1977, 398-399.

    Google Scholar 

  292. Wheeler MH, Tolmsoff WJ, Bell AA: Ultrastructural and chemical distinction of melanins formed by Verticillium dahliae from ( + )-scytalone, 1,8-dihydroxynaphthanlene, catechol, and L-3,4-dihydroxyphenylalanine. Can J Microbiol 24:289–97, 1978.

    PubMed  CAS  Google Scholar 

  293. Wheeler MH, Tolmsoff WJ, Meola S: Ultrastructure of melanin formation in Verticillium dahliae with (+ )-scytalone as a biosynthetic intermediate. Can J Microbiol 22:702–711, 1976.

    PubMed  CAS  Google Scholar 

  294. White LP: Melanin: A naturally occurring cation exchange material. Nature 182:1427–1428, 1958.

    PubMed  CAS  Google Scholar 

  295. Wolkow PM, Sisler HD, Vigil EL: Effect of inhibitors of melanin biosynthesis on structure and function of appressoria of Colletotrichum lindemuthianum. Physiol Plant Pathol 23:55–72, 1983.

    CAS  Google Scholar 

  296. Wolman M (ed):Pigments in Pathology, New York, Academic Press, 1969.

    Google Scholar 

  297. Woloshuk CP, Sisler HD: Tricyclazole, pyroquilon, tetrachlorophthalide, PCBA, coumarin and related compounds inhibit melanization and epidermal penetration by Pyricularia oryzae . JPestic Sci 7: 161–166, 1982.

    CAS  Google Scholar 

  298. Woloshuk CP, Sisler HD, Tokousbalides MC, Dutky SR: Melanin biosynthesis in Pyricularia oryzae: Site of tricyclazole inhibition and pathogenicity of melanin deficient mutants. Pestic Biochem Physiol 14:256–264, 1980.

    CAS  Google Scholar 

  299. Woloshuk CP, Sisler HD, Vigil EL: Action of the antipenetrant, tricyclazole, on appressoria of Pyricularia oryzae. Physiol Plant Pathol 22:245–259, 1983.

    CAS  Google Scholar 

  300. Woloshuk CP, Wolkow PM, Sisler HD: The effect of three fungicides, specific for the control of rice blast disease, on the growth and melanin biosynthesis by Pyricularia oryzae Cav. Pestic Sci 12:86–90, 1981.

    CAS  Google Scholar 

  301. Yamaguchi I, Sekido S, Misato T: The effect of non-fungicidal antiblast chemicals on the melanin biosynthesis and infection by Pyricularia oryzae. J Pestic Sci 7:523–529, 1982.

    CAS  Google Scholar 

  302. Yamaguchi I, Sekido S, Misato T: Inhibition of appressorial melanization in Pyricularia oryzae by non-fungicidal anti-blast chemicals. J Pestic Sci 8:229–232, 1983.

    CAS  Google Scholar 

  303. Yamaguchi I, Sekido S, Seto H, Misato T: Cytotoxic effect of 2-hydroxyjuglone, a metabolite in the branched pathway of melanin biosynthesis in Pyricularia oryzae. J Pestic Sci 8:545–550, 1983.

    CAS  Google Scholar 

  304. Yangco BG, TeStrake D, Okafor J: Phialophora richardsiae isolated from infected human bone: Morphological, physiological and antifungal susceptibility studies. Mycopathologia 86:103–111, 1984.

    PubMed  CAS  Google Scholar 

  305. Young NA, Kwon-Chung KJ, Freeman J: Subcutaneous abcess caused by Phoma sp. resembling Pyrenochaeta romeroi: Unique fungal infection occurring in immunosuppressed recipient of renal allograft. Am J Clin Pathol 59:810–816, 1973.

    PubMed  CAS  Google Scholar 

  306. Zaias N: Chromomycosis. J Cut Pathol 5:155–164, 1978.

    CAS  Google Scholar 

  307. Zenova GM: Melanoid pigments of nonchromogenic actinomycetes. Microbiology USSR 37:367–371, 1968.

    Google Scholar 

  308. Zeun R, Buchenauer H: Effect of tricyclazole on production and melanin contents of sclerotia of Botrytis cinerea. PhytopatholZ 112:259–267, 1985.

    CAS  Google Scholar 

  309. Zhdanova NN, Gauryushina AI, Vasilevskaya AI: Effect of y- and UVirradiation on survival of Cladosporium sp. and Oidiodendron cerealis. Mikrobiol Zh Kiev 35:449–452, 1973.

    PubMed  CAS  Google Scholar 

  310. Zhdanova NN, Melezhik AV, Vasilevskaya AI: Thermostability of some melanin-containing fungi. Biol Bull Acad Sci USSR 1:305–310, 1980.

    Google Scholar 

  311. Zhdanova NN, Melezhik AV, Vasilevskaya AI, Pokhodendo VD: Formation and destruction of photoinduced paramagnetic centers in melanin containing fungi. Biol Bull Acad Sci USSR 5:453–458, 1978.

    PubMed  CAS  Google Scholar 

  312. Zhdanova NN, Pokhodenko VD: The possible participation of a melanin pigment in the protection of the fungus cell from desiccation. Microbiology USSR 42:753–757, 1973.

    Google Scholar 

  313. Zhdanova NN, Pokhodenko VD: The protective properties of fungal melanin pigment of some soil Dematiaceae. Radial Res 59:221, 1974.

    Google Scholar 

  314. Zhdanova NN, Svishchuk AA, Shmygun MP, Bondar AI: The protective effect of the pigment isolated from the fungus Cladosporium sp. Microbiology USSR 39:520–524, 1970.

    Google Scholar 

  315. Zhdanova NN, Vasilevskaya AI, Antonenko AL, Udobenko VF: Resistance of some melanin-containing hyphal fungi to artificial solar light. Mikrobiol Zh Ajev43:178–182, 1981.

    CAS  Google Scholar 

  316. Ziprin R, Hartman PA: Toxicity of Pseudomonas aeruginosa bacterins and cell walls to the greater wax moth, Galleria mellonella. J Invert Pathol 17:265–269, 1971.

    CAS  Google Scholar 

  317. Zussman RA, Lyon L, Vicher EE: Melanoid pigment production in a strain of Trichophyton rubrum. J Bacteriol 80:708–713, 1960.

    PubMed  CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1988 Springer-Verlag New York Inc.

About this chapter

Cite this chapter

Wheeler, M.H., Bell, A.A. (1988). Melanins and Their Importance in Pathogenic Fungi. In: McGinnis, M.R. (eds) Current Topics in Medical Mycology. Current Topics in Medical Mycology, vol 2. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-3730-3_10

Download citation

  • DOI: https://doi.org/10.1007/978-1-4612-3730-3_10

  • Publisher Name: Springer, New York, NY

  • Print ISBN: 978-1-4612-8323-2

  • Online ISBN: 978-1-4612-3730-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics