Formation of grindelane dimers by microbial transformation

• Published in: Phytochemistry (Oxford) Vol. 31; no. 9; pp. 3045 - 3049
• Main Authors: Hoffmann, Joseph J., .Hutter, Louis K, Dentali, Steven J., Schram, Karl H., Mackenzie, Neil E.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.09.1992; Elsevier
• Subjects: 19-hydroxy-grindelic acid; 3β-hydroxy-7α,8α-epoxy grindelic acid; 3β-hydroxy-grindelic acid; 6α,17-dihydroxy-grindelic acid; Aspergillus niger; Aspergillus niger, biotransformation; Asteraceae; biodegradation; Biological and medical sciences; Biotechnology; chemical composition; derivatives; ethers; Fundamental and applied biological sciences. Psychology; Grindelia; Grindelia camporum; Metabolism; Metabolism. Physicochemical requirements; metabolites; methyl-3β-acetoxy-8α-hydroxy-grindelate-7β-O-7′β-ether hydrate; methyl-8α-hydroxy-grindelate-7β-O-7′β-ether hydrate; plant extracts; Plant physiology and development; spectral analysis; substrates; terpenoids; methyl-8α-hydroxy-grindelate-7β-O-7′β-ether hydrate; methyl-3β-acetoxy-8α-hydroxy-grindelate-7β-O-7′β-ether hydrate; Grindelia camporum; 6α,17-dihydroxy-grindelic acid; 19-hydroxy-grindelic acid; Asteraceae; Aspergillus niger, biotransformation; 3β-hydroxy-grindelic acid; 3β-hydroxy-7α,8α-epoxy grindelic acid; Fungi; Terpene; Ether; Aspergillus niger; Biotransformation; Fungi Imperfecti; Dimerization; Secondary metabolism; Thallophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/0031-9422(92)83444-4

The material balance for the biotransformation of grindelic acid by Aspergillus niger was determined along with the isolation of two novel dimers identified as methyl-8α-hydroxy-grindelate-7β-O-7′β-ether hydrate and methyl-3β-acetoxy-8α-hydroxy-grindelate-7β-O-7′β-ether hydrate. Also identified were the known 19-hydroxy-grindelic acid and the novel 6α,17-dihydroxy-grindelic acid. All compounds were isolated as their methyl ester acetate derivatives. The known 3β-hydroxy-7α,8α-epoxy grindelic acid was the sole product formed when 3β-hydroxy-grindelic acid was used as the substrate for biotransformation.