Enfumafungin (1) is a hemiacetal, triterpene glycoside that was isolated from a fermentation of
Hormonema sp. as a mixture of two interconverting forms. The primary structure of the major component of
the mixture was determined as part of the mixture, mainly via NMR and comparison with hyalodendroside A
(2), a related hemiacetal, triterpene glycoside that exists in a single form. The primary structure was confirmed,
and the relative stereochemistry determined, based on a pair of methylacetal derivatives (3 and 4). Enfumafungin
is an antifungal agent that acts as a specific inhibitor of glucan synthesis in cells and in vitro, and leads to
morphological changes in yeasts and molds.
Serine palmitoyltransferase condenses serine with a fatty acyl-CoA to form ketodihydrosphingosine in the first committed step of sphingolipid biosynthesis. A family of novel compounds, called the sphingofungins, have recently been discovered to be the first specific inhibitors of this enzyme1~3). Initially identified as antifungal agents, the sphingofungins resemble the long chain base intermediates in the sphingolipid pathway and inhibit the serine Liquid production medium C consisted of 10 g of beta-cyclodextrin, 40 g of dextrin, 7 g of distillers solubles and 5 g of yeast extract per liter of distilled water. Forty four ml of this mediumwas distributed into 250-ml unbaffled Erlenmeyer flasks. Production of antifungal activity was accomplished by adding 2ml of the seed culture described above to each production flask. Production cultures were incubated at 28°C for 4 days. Antifungal activity was produced in the culture filtrate and could conveniently be detected using the formation of zones of inhibition against Candida and Penicillium.Twoliters of the fermentation described above
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