A novel gamma-methylidene-spirobutanolide spirolephtoshol (1) was isolated from ascomycetous fungus Leptosphaeria doliolum as a cytotoxic compound. The relative structure was established by the NMR analysis involving the NOE experiments. Absolute structure of the bicyclic moiety was determined by chemical derivation followed by the CD analysis. The relative and absolute stereochemistry of the side chain was established by comparison of the (1)H NMR spectra and the chiral GC chromatograms of the degradation product with the synthetic samples.
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Characterization of Eight Novel Spiroleptosphols from .
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Department of Chemistry and Bioscience-Section for Biotechnology, Aalborg University, Frederik Bajers Vej 7H, 9220 Aalborg Ø, Denmark.
Chemical analyses of grown on banana medium resulted in eight novel spiroleptosphols, T1, T2 and U-Z (-). The structures were elucidated by a combination of high-resolution mass spectrometric data and 1- and 2-D NMR experiments. The relative stereochemistry was assigned by H coupling and NOESY/ROESY experiments.
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CBS-KNAW Fungal Biodiversity Centre, P.O. Box 85167, 3508 AD Utrecht, The Netherlands ; Wageningen University and Research Centre (WUR), Laboratory of Phytopathology, Droevendaalsesteeg 1, 6708 PB Wageningen, The Netherlands.
Unlabelled: The anamorphic genus Phoma was subdivided into nine sections based on morphological characters, and included teleomorphs in Didymella, Leptosphaeria, Pleospora and Mycosphaerella, suggesting the polyphyly of the genus. Recent molecular, phylogenetic studies led to the conclusion that Phoma should be restricted to Didymellaceae. The present study focuses on the taxonomy of excluded Phoma species, currently classified in Phoma sections Plenodomus, Heterospora and Pilosa.
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Faculty of Agriculture and Life Science, Hirosaki University, 3 Bunkyo-Cho, Hirosaki, Aomori 036-8561, Japan.
Spiroleptosphol B (2), spiroleptosphol C (3), norleptosphol C (4) and hydroleptosphol (5) were isolated from ascomycete Leptosphaeria doliolum. Detailed (1)H and (13)C NMR spectral analyses revealed these were structural analogues of spiroleptosphol (1) which we have recently isolated from the same fungi. Spiroleptosphol B (2) carried an unprecedent 5,3-dioxatricyclo[4.
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A novel gamma-methylidene-spirobutanolide spirolephtoshol (1) was isolated from ascomycetous fungus Leptosphaeria doliolum as a cytotoxic compound. The relative structure was established by the NMR analysis involving the NOE experiments. Absolute structure of the bicyclic moiety was determined by chemical derivation followed by the CD analysis.
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Universität Essen, FB 9 Botanik Universitätsstr. 5, D-45117 Essen, Germany.
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