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J Org Chem. 2011 Aug 5;76(15):6201-8. doi: 10.1021/jo2009593. Epub 2011 Jun 29.

Utilizing DART mass spectrometry to pinpoint halogenated metabolites from a marine invertebrate-derived fungus.

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1
Department of Chemistry and Biochemistry, University of California, Santa Cruz, Santa Cruz, California 95064, USA.

Abstract

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. Subsequently, the metabolites were isolated from liquid culture in artificial seawater. The structures of two novel chlorinated metabolites, named (-)-spiromalbramide and (+)-isomalbrancheamide B, provide additional insights into the assembly of the malbrancheamide compound family. Remarkably, two new brominated analogues, (+)-malbrancheamide C and (+)-isomalbrancheamide C, were produced by enriching the growth medium with bromine salts.

PMID:
21682275
PMCID:
PMC3242642
DOI:
10.1021/jo2009593
[Indexed for MEDLINE]
Free PMC Article
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