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-te trahydrofuran-2-acetic acid (5-HTFA) by Bacillus lentus NRRL B-14864 ( B-14864) was carried out in the presence or absence of oligomycin, 2-b romooctanoic acid (2-BA), or sodium azide. In addition, several satura ted and monounsaturated monohydroxyfatty acids, saturated monooxofatty acids, and monounsaturated fatty acid were used as substrates for tra nsformation reactions by B-14864 or corynebacterium FUI-2. Methyl este rs of the transformation products were analyzed by gas chromatography and gas chromatography/mass spectroscopy. Various gamma-lactones and t etrahydrofuran fatty acid derivatives were conversion products when sa turated monohydroxyfatty acids were used as substrates; the production of 5-HTFA from 12-HOA by B-14864 cells was completely inhibited in th e presence of high concentration of oligomycin, 2-BA, or sodium azide; and fatty acid P-oxidation metabolic intermediates, 6-hydroxydodecano ic, 4-oxododecanoic, and 4-oxodecanoic acids were products when 12-HOA , 10-ore-, and 12-oxooctadecanoic acids were used as substrates. Our r esults suggest that the production of 5-HTFA from 12-HOA by B-14864 wa s through the fatty acid P-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-lik e activity in pure form but not when it was diluted to 10%.