Novel secondary metabolites, spirosorbicillinols a, B, and C, from a fungus.
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.
Washida
Kazuto
K
School of Food and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan.
Abe
Naoki
N
Sugiyama
Yasumasa
Y
Hirota
Akira
A
D005658:Fungi / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012118:Resorcinols / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D012118:Resorcinols; C473616:sorbicillin