BIOTRANSFORMATION OF SATURATED MONOHYDROXYL FATTY ACIDS TO 2-TETRAHYDRO- FURANYL ACETIC ACID DERIVATIVES: MECHANISM OF FORMATIONS AND THE BIOLOGICALACTIVITY OF 5-N-HEXYL-TETRAHYDROFURAN-2-ACETIC ACID

Authors: HUANG, JENQ-K - WESTERN IL UNIV, MACOMB; DOWD, PATRICK - 3620-30-00; KEUDELL, KENNETH - WESTERN IL UNIV, MACOMB; KLOPFENSTEIN, WILLIAM - WESTERN IL UNIV, MACOMB; WEN, LISA - WESTERN IL UNIV, MACOMB; Bagby, Marvin; Lanser, Alan; Norton, Robert

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/25/1996
Publication Date: N/A
Citation: N/A

Interpretive Summary: While searching for microorganisms that are capable of modifying the fatty acids found in soybean oil, a Bacillus was identified that produced new compounds (called tetrahydrofurans) that interfere with insect development (juvenile hormone activity). The mechanism of product formation was shown to occur through fatty acid chain shortening by loss of two carbon atoms per cycle (known as beta-oxidation). Knowledge of the mechanism will allow the preparation of similar compounds differing in sidechain substituents. This family of compounds will possess a variety of physical properties and should show a range of biological activity.

Technical Abstract: Transformation of 12-hydroxyoctadecanoic acid (12-HOA) to 5-n-hexyl-tetrahydrofuran-2-acetic acid (5-HTFA) by Bacillus lentus NRRL B-14864 (B-14864) was carried out in the presence or absence of oligomycin, 2-bromooctanoic acid (2-BA) or sodium azide. In addition, several saturated and monounsaturated monohydroxy fatty acids, saturated monooxofatty acids and a monounsaturated fatty acid were used as substrates. Methyl esters of the transformation products were analyzed by gas chromatography (GC) and gas chromatography-mass spectroscopy (GC-MS). Various delta-lactones and tetrahydrofuran fatty acid derivatives were conversion products when saturated monohydroxy fatty acids were used as substrates; the production of 5-HTFA from 12-HOA by B-14864 cells was completely inhibited in the presence of high concentration, 2-BA or sodium azide; and fatty acid beta-oxidation metabolic intermediates, 6-hydroxydodecanoic, 4-oxododecanoic and 4-oxodecanoic acids were products when 12-HOA, 10-oxo- and 12-oxooctadecanoic acids were used as substrates, respectively. Our results suggest that the production of 5-HTFA from 12-HOA by B-14864 was through the fatty acid beta-oxidation pathway.