Novel secondary metabolites, spirosorbicillinols A, B, and C, from a fungus

• Published in: Bioscience, biotechnology, and biochemistry Vol. 73; no. 6; pp. 1355 - 1361
• Main Authors: Washida, K.(Shizuoka Univ. (Japan). School of Food and Nutritional Sciences), Abe, N, Sugiyama, Y, Hirota, A
• Format: Journal Article
• Language: English
• Published: Tokyo Japan Society for Bioscience, Biotechnology, and Agrochemistry 01.06.2009; Japan Society for Bioscience Biotechnology and Agrochemistry; Oxford University Press
• Subjects: AISLAMIENTO; Biological and medical sciences; biosynthesis; CHEMICAL REACTIONS; CHEMICAL STRUCTURE; COMPOSE ORGANIQUE; COMPUESTOS ORGANICOS; DEGRADACION; DEGRADATION; Diels-Alder reaction; DPPH-radical scavenger; ESPECTROSCOPIA RMN; ESTRUCTURA QUIMICA; FERMENTACION; FERMENTATION; Fundamental and applied biological sciences. Psychology; Fungi - chemistry; IDENTIFICACION; IDENTIFICATION; ISOLATION; ISOLEMENT; Magnetic Resonance Spectroscopy; Models, Molecular; NMR SPECTROSCOPY; ORGANIC COMPOUNDS; REACCIONES QUIMICAS; REACTION CHIMIQUE; Resorcinols - chemistry; Resorcinols - isolation & purification; Resorcinols - metabolism; SOIL; SOL; sorbicillin related compounds; Spectrometry, Mass, Fast Atom Bombardment; SPECTROSCOPIE RMN; Stereoisomerism; STRUCTURE CHIMIQUE; SUELO; TRICHODERMA; Fungi; sorbicillin related compounds; Metabolite; Diels Alder addition; DPPH-radical scavenger; Biosynthesis; Diels-Alder reaction
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.90015

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.