Biotransformation of saturated monohydroxyl fatty acids to 2‐tetrahydrofuranyl acetic acid derivatives: Mechanism of formations and the biological activity of 5‐n‐hexyl‐tetrahydrofuran‐2‐acetic acid

Abstract

AbstractTransformation of 12‐hydroxyoctadecanoic acid (12‐HOA) to 5‐n‐hexyl‐tetrahydrofuran‐2‐acetic acid (5‐HTFA) byBacillus 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 monohydroxyfatty acids, saturated monooxofatty acids, and monounsaturated fatty acid were used as substrates for transformation reactions by B‐14864 or corynebacterium FUI‐2. Methyl esters of the transformation products were analyzed by gas chromatography and gas chromatography/mass spectroscopy. Various γ‐lactones and tetrahydrofuran fatty acid derivatives were conversion products when saturated monohydroxyfatty 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 of oligomycin, 2‐BA, or sodium azide; and fatty acid β‐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. Our results suggest that the production of 5‐HTFA from 12‐HOA by B‐14864 was through the fatty acid β‐oxidation pathway. Three‐day‐old driedfruit beetle pupae were topically treated with 5‐HTFA to test for juvenile hormone activity, and 5‐HTFA was found to possess juvenile hormone‐like activity in pure form but not when it was diluted to 10%.