Novel Secondary Metabolites, Spirosorbicillinols A, B, and C, from a Fungus
Authors:
- Naoki AbeNANaoki Abe
- Yasumasa SugiyamaYSYasumasa Sugiyama
- Akira HirotaAHAkira Hirota
- 23 June 2009
- journal article
- Published by Oxford University Press (OUP) in Bioscience, Biotechnology, and Biochemistry
- Vol. 73 (6) , 1355-1361
Abstract
In our searching program for novel sorbicillin related compounds, three novel compounds, spirosorbicillinols A (1), B (2), and C (3), were isolated from the fermentation broth of the USF-4860 strain isolated from a soil sample. The planar structures of compounds 1-3 were determined from spectroscopic evidence and degradation reaction, and that of 1 was the same as that of 2. The relative stereochemistries of compounds 1-3 were determined by (1)H-(1)H coupling constants, the elucidation of HMBC and NOESY spectra in detail. 1 and 2 were stereoisomers at C8 position, each other. We propose that compounds 1 and 2 were formed by exo and endo intermolecular Diels-Alder reaction between sorbicillinol as a diene and scytolide (proposed precursor-1) as a dienophile, respectively. Similarly, we propose that compound 3 was formed by an endo intermolecular Diels-Alder reaction between sorbicillinol and proposed precursor-2.Keywords
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