Four new prenylindole derivatives, (R)-6-(2,3-dihydroxy-3-methylbutyl)indole (1), (R)-6-(2,3-dihydroxy-3-methylbutyl)indolin-2-one (2), and an unseparated mixture of (Z)-6-(4-hydroxy-3-methylbut-2-en-1-yl)indolin-2-one (3a) and (E)-6-(4-hydroxy-3-methylbut-2-en-1-yl)indolin-2-one (3b) with a ratio of 3 : 2, were isolated from the culture broth of a streptomycete isolated from Ailuropoda melanoleuca feces. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopic techniques. The absolute configuration of 1 was determined by Mosher's method.
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Prenylated indole alkaloids are a diverse group of fungal secondary metabolites and represent an important biosynthetic class. In this study we have identified new halogenated prenyl-indole alkaloids from an invertebrate-derived Malbranchea graminicola strain. Using direct analysis in real time (DART) mass spectrometry, these compounds were initially detected from hyphae of the fungus grown on agar plates, without the need for any organic extraction.
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