Journal
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
Volume 73, Issue 6, Pages 1355-1361Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1271/bbb.90015
Keywords
sorbicillin related compounds; biosynthesis; Diels-Alder reaction; DPPH-radical scavenger
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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 or 1 was the same as that or 2. The relative stereochemistries of compounds 1-3 were determined by H-1-H-1 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.
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