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1,8-Dihydroxynaphthalene monoglucoside, a new metabolite of Sclerotinia sclerotiorum, and the effect of tricyclazole on its production

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Isolate SS7 of Sclerotinia sclerotiorum was previously shown to produce and excrete into agar medium copious amounts of the melanin precursor 1,8-dihydroxynaphthalene. Much reduced quantities of this product were produced in the presence of tricyclazole, an inhibitor of pentaketide melanin biosynthesis. In this study, we demonstrate that young cultures of isolate SS7 produce 1,8-dihydroxynaphthalene monoglucoside, a new natural product not previously reported from fungi. When cultured in the presence of tricyclazole, such young cultures also accumulated two new monoglucosides of 1,3,8-trihydroxynaphthalene, which, as well as 1,8-dihydroxynaphthalene monoglucoside, were also obtained from cultures of two other isolates of S. sclerotiorum. It is proposed that rapid glucosylation of 1,3,8-trihydroxynaphthalene in young tricyclazole-inhibited S. sclerotiorum cultures accounts for the failure to observe 2-hydroxyjuglone or other metabolites usually associated with blockage of the pentaketide pathway to melanin in fungi.Key words: Sclerotinia sclerotiorum, melanin production, tricyclazole, phenol glucosylation.

Il a déjà été démontré que l'isolat SS7 de Sclerotinia sclerotiorum produit et sécrète dans des milieux gélosés des quantités importantes de 1,8-dihydroxynaphtalène, un précurseur de la mélanine. Ce composé est produit en beaucoup plus faible quantité en présence de tricyclazole, un inhibiteur de la biosynthèse de la mélanine par le sentier de la pentacétogénine. Dans la présente étude, nous démontrons que des cultures jeunes de cet isolat SS7 produisent du 1,8-dihydroxynaphtalène monoglucoside, un nouveau produit naturel jamais décrit jusqu'à maintenant chez les champignons. En présence de tricyclazole, ces jeunes cultures produisent aussi deux nouveaux monoglucosides du 1,3,8-trihydroxynaphtalène qui, comme le 1,8-dihydroxynaphtalène monoglucoside, sont aussi produits par les cultures de deux autres isolats de S. sclerotiorum. Nous croyons qu'une glycosylation rapide du 1,3,8-trihydroxynaphtalène dans les jeunes cultures de S. sclerotiorum inhibées par le tricyclazole serait responsable de l'absence de 2-hydroxyjuglone ou d'autres métabolites habituellement associés au blocage du sentier de la pentacétogénine de la synthèse de la mélanine chez les champignons.Mots clés : Sclerotinia sclerotiorum, production de mélanine, tricyclazole, glucosylation des phénols.[Traduit par la Rédaction]

Keywords: Sclerotinia sclerotiorum; glucosylation des phénols; melanin production; phenol glucosylation; production de mélanine; tricyclazole

Document Type: Research Article

Publication date: April 1, 2002

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  • Published since 1954, this monthly journal contains new research in the field of microbiology including applied microbiology and biotechnology; microbial structure and function; fungi and other eucaryotic protists; infection and immunity; microbial ecology; physiology, metabolism and enzymology; and virology, genetics, and molecular biology. It also publishes review articles and notes on an occasional basis, contributed by recognized scientists worldwide.
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