Utilizing DART Mass Spectrometry to Pinpoint Halogenated Metabolites from a Marine Invertebrate-Derived Fungus

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 (DAR...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 76; no. 15; pp. 6201 - 6208
Main Authors Watts, Katharine R, Loveridge, Steven T, Tenney, Karen, Media, Joseph, Valeriote, Frederick A, Crews, Phillip
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.08.2011
Amer Chemical Soc
Subjects
Online AccessGet full text

Cover

Loading…
More Information
Summary: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.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
University of California, Santa Cruz
Henry Ford Hospital
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2009593