Utilizing DART Mass Spectrometry to Pinpoint Halogenated Metabolites from a Marine Invertebrate-Derived Fungus
- 17 June 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (15), 6201-6208
- https://doi.org/10.1021/jo2009593
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.Keywords
This publication has 36 references indexed in Scilit:
- Genome-Based Characterization of Two Prenylation Steps in the Assembly of the Stephacidin and Notoamide Anticancer Agents in a Marine-Derived Aspergillus sp.Journal of the American Chemical Society, 2010
- Concise Enantioselective Synthesis of ent-Malbrancheamide BJournal of the American Chemical Society, 2009
- Isolation of Antipodal (−)-Versicolamide B and Notoamides L−N from a Marine-Derived Aspergillus sp.Organic Letters, 2009
- Calmodulin inhibitory activity of the malbrancheamides and various analogsBioorganic & Medicinal Chemistry Letters, 2008
- Notoamides F−K, Prenylated Indole Alkaloids Isolated from a Marine-Derived Aspergillus sp.Journal of Natural Products, 2008
- Premalbrancheamide: Synthesis, Isotopic Labeling, Biosynthetic Incorporation, and Detection in Cultures of Malbranchea aurantiacaOrganic Letters, 2008
- Molecular Analysis of a 4-Dimethylallyltryptophan Synthase from Malbranchea aurantiacaPublished by Elsevier BV ,2008
- Cuticular hydrocarbon analysis of an awake behaving fly using direct analysis in real-time time-of-flight mass spectrometryProceedings of the National Academy of Sciences of the United States of America, 2008
- Biomimetic Total Synthesis of Malbrancheamide and Malbrancheamide BThe Journal of Organic Chemistry, 2008
- Tremorgenic Toxins from Aspergillus fumigatus FRESCHEMICAL & PHARMACEUTICAL BULLETIN, 1971