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

Transformation 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%. Presented in part at the 37th West Central States Biochemistry Conference Annual Meeting, Columbia, Missouri, Oct. 1994.