Malbrancheamide B, a novel compound from the fungusMalbranchea aurantiaca1
- 19 May 2008
- journal article
- research article
- Published by Informa UK Limited in Natural Product Research
- Vol. 22 (8), 709-714
- https://doi.org/10.1080/14786410802012361
Abstract
A new indole alkaloid, namely malbrancheamide B (2), was isolated from the culture medium and mycelia of the ascomycete Malbranchea aurantiaca along with malbrancheamide (1). Structural elucidation of 2 was carried out by a combination of mass spectrometry (MS) and 1H and 13C NMR spectroscopy analyses, as well as by comparison of the NMR data with those of 1. According to the conformational studies using molecular mechanics analyses, compound 2 exists in one preferred conformation, which was optimised by density functional theory (DFT) calculations. Compound 2 is the second chlorinated indole alkaloid possessing a bicyclo [2.2.2] ring with an unusual relative configuration at C12a in the bicyclo [2.2.2] diazaoctane ring system. So far, these structural features seem to be unique for the alkaloids biosynthesised by the fungus M. aurantiaca.Keywords
This publication has 7 references indexed in Scilit:
- Malbrancheamide, a new calmodulin inhibitor from the fungus Malbranchea aurantiacaTetrahedron, 2006
- Phytotoxins from the fungus Malbranchea aurantiacaPhytochemistry, 2005
- Chemistry and Biology of Biosynthetic Diels–Alder ReactionsAngewandte Chemie-International Edition, 2003
- Paraherquamides, Brevianamides, and Asperparalines: Laboratory Synthesis and Biosynthesis. An Interim ReportAccounts of Chemical Research, 2002
- An internal-coordinate Monte Carlo method for searching conformational spaceJournal of the American Chemical Society, 1989
- Studies in relation to biosynthesis—XLIVTetrahedron, 1972
- Studies in relation to biosynthesis—XLIITetrahedron, 1970