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EnglishTwo new metabolites, (4S)-(+)-ascochin (1a) and (S,S)-(+)-ascodiketone (3), together with the known compounds (3R,4R)-(–)-4-hydroxymellein (2), ent-α-cyperone (4) and (3S,4R)-(–)-dihydroxy-(6S)-undecyl-α-pyranone (5) were isolated from cultures of the of the endophytic fungus Ascochyta sp. The biologically active isocoumarin derivative, (4S)-(+)-ascochin (1a), has an unusual substitution pattern which was confirmed by X-ray diffraction. Its absolute configuration was determined by our solid-state TDDFT CD methodology using the X-ray coordinates as input for the calculation. By catalytic hydrogenation, (4S)-(+)-ascochin was converted into the corresponding (3S,4S)-dihydroisocoumarin derivative 1b. The measured and TDDFT calculated CD spectra enabled studies on the correlation between absolute configuration and n-π* transition Cotton effect.
| Autori interni: | ||
| Autori: | KROHN K; KOCK I; ELSSSER B; FLOERKE U; SCHULZ B; DRAEGER S; PESCITELLI G; ANTUS S; KURTAN T | |
| Titolo: | Bioactive Natural Products from the Endophytic Fungus Ascochyta sp. From Meliotus dentatus – Configurational Assignment by Solid-State CD and TDDFT Calculations | |
| Anno del prodotto: | 2007 | |
| Digital Object Identifier (DOI): | 10.1002/ejoc.200600907 | |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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http://hdl.handle.net/11568/116913
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