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Trienylfuranol A and trienylfuranone A-B: metabolites isolated from an endophytic fungus, Hypoxylon submoniticulosum, in the raspberry Rubus idaeus.
- Source :
-
The Journal of antibiotics [J Antibiot (Tokyo)] 2017 Jun; Vol. 70 (6), pp. 721-725. Date of Electronic Publication: 2017 Mar 01. - Publication Year :
- 2017
-
Abstract
- A strain of Hypoxylon submonticulosum was isolated as an endophyte from a surface-sterilized leaf of a cultivated raspberry (Rubus idaeus). The liquid culture extract displayed growth inhibition activity against Saccharomyces cerevisiae using a disc diffusion assay. The extract's major component was identified as a new natural product, trienylfuranol A (1S,2S,4R)-1-((1'E,3'E)-hexa-1',3',5'-trienyl)-tetrahydro-4-methylfuran-2-ol (1), by high-resolution LC-MS and 1D and 2D NMR spectroscopy. Two additional new metabolites, trienylfuranones A (2) and B (3), were isolated as minor components of the extract and their structure elucidation revealed that they were biosynthetically related to 1. Absolute stereochemical configurations of compounds 1-3 were confirmed by NOE NMR experiments and by the preparation of Mosher esters. Complete hydrogenation of 1 yielded tetrahydrofuran 7 that was used for stereochemical characterization and assessment of antifungal activity.
- Subjects :
- 4-Butyrolactone chemistry
4-Butyrolactone isolation & purification
4-Butyrolactone pharmacology
Antifungal Agents chemistry
Antifungal Agents isolation & purification
Antifungal Agents pharmacology
Chromatography, Liquid
Endophytes isolation & purification
Endophytes metabolism
Furans chemistry
Furans pharmacology
Magnetic Resonance Spectroscopy
Mass Spectrometry
Microbial Sensitivity Tests
Plant Leaves
Saccharomyces cerevisiae drug effects
Xylariales isolation & purification
4-Butyrolactone analogs & derivatives
Furans isolation & purification
Rubus microbiology
Xylariales metabolism
Subjects
Details
- Language :
- English
- ISSN :
- 1881-1469
- Volume :
- 70
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- The Journal of antibiotics
- Publication Type :
- Academic Journal
- Accession number :
- 28246381
- Full Text :
- https://doi.org/10.1038/ja.2017.18