Black fungal extremes - CBS

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Yu r l o va e t a l.AcetateMelanin(O)OHOH(H)TrOHO-H 2 OOHOH(H)TrOOH-H 2 OOHOHHOOHHOOHHOHO1,3,6,8-THNScytalone1,3,8-THNVermeloneDHN(O)(O)OOHHOOOOHHOOH(o)HOOH2HOOOOFlaviolin3,3'-Biflaviolin2-HJ(H)(O)(H)(O)OHOH(H)OHO-H 2 OOHOHOOH(O)HOOOHHOOHHOOHHOOHOHOHOO1,2,4,5 ,7-P HN5-HS1,2,4,5-THNJuglone3-HJ(H)(H)(H)(O)OOHOOHOHOHOOH-H 2 O(H)HOOHHOOHOHOHOH4-HS3,4,8-THT1,4,5-THN4,8-DHTFig. 7. Biosynthetic pathway of DHN-melanin and related pentaketide metabolites, from the scheme shown by Bell & Wheeler (1986). The first known product of the pathwayis I.3.6.8-THN. This metabolite is reduced lo scytalone, which is then dehydrated to 1,3.8-THN. Next, 1.3.8-THN is reduced to vermelone, which is then dehydrated to DHN.The enzyme(s) that catalyze the final polymerization reaction, oxidation of DHN to melanin, have not yet been adequately studied but it appears to be a laccase. Tricyclazole(Tr) inhibits the reduction of 1.3.6,8-THN and 1.3.8-THN to scytalone and vermelone, respectively. Its strongest inhibitory effect is on the reduction of 1.3.8-THN. This results in theaccumulation of flaviolin, 2-HJ, and their re lated shunt products, 1.2.4.5.7-pentahydroxynaphthalene (1.2.4.5.7-PHN), 1.2.4.5-tetrahydroxynaphthalene (1.2.4.5-THN), and 1.4.5-trihydroxynaphthalene (1.4.5-THN) are extremely unstable and have not been isolated from fungi.cultivated in media with high (30−50 µg/mL) concentrations oftricyclazole. The halophilic ascomycetous black yeasts Hortaeawerneckii, Phaeotheca triangularis and Trimmatostroma salinumaccumulated 4,8-dihydroxytetralone (4,8-DHT) in cultures noninhibitedby TR (Kogej et al. 2004) (Fig. 7). Small amounts of4-hydroxyscytalone (4-HS) (Fig. 7) have been reported in wild-typecultures of Curvularia lunata non-inhibited by TR (Rižner & Wheeler2003), as well as of scytalone in Thielaviopsis basicola (Wheeler &Stipanovic 1979) and Sporothrix schenckii (Romero-Martinez et al.2000). This means that products which are typical for cultures ofblack yeasts inhibited by tricyclazole (TR) were also found in noninhibitedcultures.In our earlier investigations (Yurlova & Sindeeva 1996) we provedthe presence of intracellular and extracellular laccase activity of 14above mentioned strains of black yeasts. Tricyclazole decreasedlaccase activity (Yurlova & Sindeeva 1995). Tyrosinase, whichoxidises tyrosine, was not found in any of the strains investigated(Table 1) (Yurlova & Sindeeva 1995). On the basis of the presentdata we hypothesise that black yeasts contain a multipotentpolyphenoloxidase able to oxidise substrates characteristicfor o-diphenoloxidases and p-diphenoloxidases. Such kind ofmultipotent polyphenoloxidase has previously been observed inthe marine bacterium Marinomonas mediterranea (Fernandez etal. 1999). The melanisation process might involve other enzymesand more substrates than those commonly recognised. Themechanism of biosynthesis of black yeast melanins remains to befurther elucidated.ACKNOWLEDGEMENTSWe are grateful to Drs N.N. Stepanichenko and L.N. Ten, Tashkent State University,Uzbekistan, for assistance in obtaining TLC data.REFERENCESBell AA, Wheeler MH (1986). Biosynthesis and function of fungal melanins. AnnualReviews in Phytopathology 24: 41–451.Butler MJ, Day AW (1998). Fungal melanins: a review. Canadian Journal ofMicrobiology 44: 1115–1136.Blinova MI, Yudintzeva NM, Kalmykova NV, Kuzminykh EV, Yurlova NA,Ovchinnikova OA, Potokin IA (2003). Effects of melanins from black yeastfungi on proliferation and differentiation of cultivated human keratinocytes andfibroblasts. International Journal of Cell Biology 27: 135–146.Butler MJ, Gardiner RB, Day AW (2004). Use of the black yeast Phaeococcomyces48
Pi gm e n t f o r m at i o n in b l a c k y e a s t-l i k e f u n g ifungal melanin model system for preparation of 1,3,6,8-tetrahydroxynaphthaleneand the other component of the DHN fungal melanin pathway. InternationalJournal of Plant Science 165: 787–793.Della-Cioppa G, Garger SJ, Sverlow GG, Turpen TH, Grill LK (1990). Melaninproduction in Escherichia coli from a cloned tyrosinase gene. Biotechnology8: 634–638.Deshpande MS, Rale VB, Lynch JM (1992). Aureobasidium pullulans in appliedmicrobiology: a status report. Enzyme Microbiology and Technology 14: 514–527.Fernandez E, Sanchez-Amat A, Solano F (1999). Location and catalic characteristicsof a multipotent bacterial polyphenol oxidase. Pigment Cell Research 12: 331–339.Hoog GS de, Guarro J, Gené J, Figueras MJ (2000). Atlas of Clinical Fungi. 2 ndedition. CBS. Utrecht, The Netherlands. Universitat Rovira i Virgili. Reus,Spain.Hoog GS de, Matos T, Sudhadham M, Luijsterburg KF, Haase G (2005). Intestinalprevalence of the neurotopic black yeast Exophiala (Wangiella) dermatitidis inhealthy and impaired individuals. Mycoses 48: 142–145.Hoog GS de, Zalar P, Urzί C, Leo F de, Yurlova NA, Sterflinger K (1999). Relationshipsof dothideaceous black yeasts and meristematic fungi based on 5.8S and ITS2rDNA sequence comparison. Studies in Mycology 43: 31–37.Kogej T, Wheeler MH, Rižner TL, Gunde-Cimerman N (2004). Evidence for1,8-dihydroxynaphthalene melanin in three halophilic black yeasts grown undersaline and non-saline conditions. FEMS Microbiology Letters 232: 203–209.Latgé JP, Bouziane H, Diaquin M (1988). Ultrastructure and composition ofthe conidial wall of Cladosporium cladosporioides. Canadian Journal ofMicrobiolology 34: 1325–1329.Lyakh SP (1981). Microbial Melaninogenesis and its Function. Moscow: Science.274 pp.Rižner TL, Wheeler MH (2003). Melanin biosynthesis in the fungus Culvularia lunata(teleomorph: Cochliobolus lunatus). Canadian Journal of Microbiolology 49:110–119.Romero-Martinez R, Wheeler MH, Guerrero-Plata A, Pico G, Torres-Guerrero H(2000). Biosynthesis and function of melanin in Sporothrix schenckii. Infectionand Immunity 68: 3696–3703.Siehr DJ (1981). Melanin biosynthesis in Aureobasidium pullulans. Journal ofCoating Technology 53: 23–25.Sterflinger K, Krumbein WE (1995). Multiple stress factors affecting growth of rockinhabiting black fungi. Botanica Acta 108: 467–538.Sterflinger K, Krumbein WE (1997). Dematiaceous fungi as a major agent forbiopitting on Mediterranean marbles and limestones. Geomicrobiology Journal14: 219–230.Taylor BE, Wheeler MH, Szaniszlo PJ (1987). Evidence for pentaketide melaninbiosynthesis in dematiaceous human pathogenic fungi. Mycologia 79: 320–322.Turkovskii II, Yurlova NA (2002). The photochemical and surface-active propertiesof melanins isolated from some black yeast fungi. Mikrobiologiya (Russian)71: 482–490.Vitale RG, Hoog GS de (2002). Molecular diversity, new species and antifungalsusceptibilities in the Exophiala spinifera clade. Medical Mycology 40: 545–556.Wheeler MH (1983). Comparisons of fungal melanin biosynthesis in ascomycetous,imperfect and basidiomycetous fungi. Transactions of the British MycologicalSociety 81: 29–36.Wheeler MH, Greenblatt GA (1988). The inhibition of melanin biosynthesis reactionsin Pyricularia oryzae by compounds the prevent rice blast disease. ExperimentalMycology 12:151–160.Wheeler MH, Stipanovic RD (1979). Melanin biosynthesis in Thielaviopsis basicola.Experimental Mycology 3: 340–350.Yurlova NA (2001). Applied aspects of dothideaceous black yeasts: melanins.21st International specialized symposium on yeasts “Biochemistry, genetics,biotechnology and ecology of non-yeasts (NCY)”. Lviv, Ukraine: 123.Yurlova NA, Hoog GS de (1997). A new variety of Aureobasidium pullulanscharacterized by exopolysaccharide structure, nutritional physiology andmolecular features. Antonie van Leeuwenhoek 72: 141–147.Yurlova NA, Sindeeva LV (1996). Production of phenoloxidases by black yeasts asan indicator of their biodeteriorative activity. Papers of the 10th InternationalBiodeterioration and Biodegradation Symposium, Hamburg, Dechema: 169–175.Zhdanova NM, Vasylevskaya AI, Tugay TI, Artyshkova, LV, Nakonechnaya LT,Dighton J (2007). Results of 20 yr monitoring of soil mycobiota within the 10-km alienation zone of the Chernobyl nuclear power plant. Abstr. XV Congressof European Mycologists. Saint Petersburg, Russia: 108.Zhdanova NM, Zakharchenko VO, Vasylevskaya AI, Shkol’nyi OT, NakonechnayaLT, Artyshkova LV (1994). Peculiarities of soil mycobiota composition inChernobyl NPP. Ukrainian Botanical Zhurnal 51: 134–143.www.studiesinmycology.org49
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Studies in Mycology 61 (2008)Black
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Studies in MycologyThe Studies in M
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On o f r i e t a l.2005). The abili
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De n g e t a l.Table 1. Strains use
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De n g e t a l.10098CBS 157.67 Exop
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e n v i r o nm e n ta l is o l at i
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Origin o f Ex o p h i a l a d e r m
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s u b s t r at e s p e c i f i c i
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homogentisate 165, 171, 173Hortaea
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CBS Biodiversity SeriesNo. 6: Alter
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Studies in Mycology (ISSN 0166-0616
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Satow MM, Attili-Angelis D, Hoog GS
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Black fungal extremes - CBS

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