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Appl Environ Microbiol. 1987 October; 53(10): 2482-2486
Copyright © 1987, American Society for Microbiology. All Rights Reserved.

Microbial Hydroxylation of 1,4-Cineole

¹ Division of Medicinal and Natural Products Chemistry, College of Pharmacy, The University of Iowa, Iowa City, Iowa 52242, and Agricultural Products Department, Experimental Station, E. I. du Pont de Nemours & Co., Inc., Wilmington, Delaware 19898²

ABSTRACT

Microorganisms were examined for their potential to hydroxylate the oxygenated monoterpene 1,4-cineole. Using gas chromatography and thin-layer chromatography, screening experiments revealed that hydroxylation at position 2 was the most commonly observed microbial transformation reaction. In most microorganisms, the predominant alcohol metabolite was the 2-endo-alcohol isomer. Preparative-scale incubations were conducted in order to isolate and characterize microbial transformation products by comparison of proton nuclear magnetic resonance, mass spectrometry, and chromatography profiles with those of cineole standards. Streptomyces griseus yielded 8-hydroxy-1,4-cineole as the major hydroxylation product together with 2-exo- and 2-endo-hydroxy-1,4-cineoles.

^* Corresponding author.