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- W1966811293 abstract "The endophytic fungus Pestalotiopsis virgatula, derived from the plant Terminalia chebula and previously found to produce a large excess of a single metabolite when grown in the minimal M1D medium, was induced to produce a variety of unusual metabolites by growing in potato dextrose broth medium. Analysis of the fermentation medium extract was performed using an HPLC-PDA-MS-SPE-NMR hyphenated system, which led to the identification of a total of eight metabolites (1-8), six of which are new. Most of the metabolites are structurally related and are derivatives of benzo[c]oxepin, rare among natural products. This includes dispiro derivatives 7 and 8 (pestalospiranes A and B), having a novel 1,9,11,18-tetraoxadispiro[6.2.6.2]octadecane skeleton. Relative and absolute configurations of the latter were determined by a combination of NOESY spectroscopy and electronic circular dichroism spectroscopy supported by time-dependent density-functional theory calculations (B3LYP/TZVP level). This work demonstrates that a largely complete structure elucidation of numerous metabolites present in a raw fermentation medium extract can be performed by the HPLC-SPE-NMR technique using only a small amount of the extract, even with unstable metabolites that are difficult to isolate by traditional methods." @default.
- W1966811293 created "2016-06-24" @default.
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- W1966811293 date "2011-09-26" @default.
- W1966811293 modified "2023-09-27" @default.
- W1966811293 title "Production of Unusual Dispiro Metabolites in<i>Pestalotiopsis virgatula</i>Endophyte Cultures: HPLC-SPE-NMR, Electronic Circular Dichroism, and Time-Dependent Density-Functional Computation Study" @default.
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- W1966811293 doi "https://doi.org/10.1021/np2005665" @default.
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