Isolation of Fatty Acids from the Enzymatic Hydrolysis of Capsaicinoids and Their Use in Enzymatic Acidolysis of Coconut Oil.

Herein we report the optimization of enzymatic hydrolysis of a mixture of capsaicinoids, capsaicin and dihydrocapsaicin obtained from chili peppers, and the utilization of the isolated fatty acids for the modification of coconut oil using enzyme catalyzed acidolysis. This work was carried out as the fatty acids that can be isolated from capsaicinoid hydrolysis have been shown to possess interesting biological properties. These biological properties could be better exploited by incorporating the fatty acids into a suitable delivery vehicle. The enzymatic hydrolysis of the mixture of capsaicin and dihydrocapsaicin was carried out using Novozym® 435 in phosphate buffer (pH 7.0) at 50℃. The enzyme catalyst could be reused in multiple cycles of the hydrolysis reaction. The desired 8-methyl-6-trans-nonenoic acid and 8-methylnonanoic acid were isolated from the hydrolysis reaction mixture using a simple extraction procedure with a 47.8% yield. This was carried out by first extracting the reaction mixture at pH 10 with ethyl acetate to remove any dissolved capsaicinoids and vanillyl amine side product. The fatty acids were isolated after adjustment of the pH of the reaction mixture to 5 and second extraction with ethyl acetate. The acidolysis of coconut oil with the obtained fatty acids was performed using Lipozyme® TL IM. The performance of the acidolysis reaction was evaluated using 1H-NMR spectroscopy and verified in selected cases using gas chromatography. The best performing conditions involved carrying out the acidolysis reaction at 60℃ with a 1.2 w/w ratio of the fatty acids to coconut oil and 10% enzyme loading for 72 h. This resulted in the incorporation of 26.61% and 9.86% of 8-methyl-6-trans-nonenoic acid and 8-methylnonanoic acid, respectively, into the modified coconut oil product. This product can act as a potential delivery vehicle for these interesting compounds.

Reduction of lauric acid content in virgin coconut oil improved plasma lipid profile in high-fat diet-induced hypercholesterolemic mice.

Virgin coconut oil (VCO) is claimed to have various health benefits, but favorable effects of its major component (∼50%), lauric acid, are controversial. Therefore, we aimed to reduce lauric acid content (∼30%) in VCO and evaluate its effect compared to VCO and medium-chain triglycerides (MCT), on food intake, bodyweight (BW), lipid profiles, and hepatic histology. Female C57BL/6 mice were treated with different diets for 3 months: control (normal diet), high-fat diet (HF), HF + VCO, HF + MCT, HF + low lauric acid VCO (LLA), and normal diet + LLA (C + LLA). LLA was prepared by enzymatic interesterification of VCO with methyl octanoate (methyl caprylate) and methyl decanoate (methyl caprate). Plasma and liver lipids, including total cholesterol (TC), high-density lipoprotein (HDL), and triglyceride, were measured by colorimetric assay, and hepatic fat accumulation was examined by oil-red-O staining. HF mice exhibited high plasma and liver TC and low-density lipoprotein (LDL). VCO or MCT treatment lowered liver TC and LDL, whereas LLA increased plasma HDL and markedly improved TC:HDL ratio. The HF-induced hepatic fat accumulation was attenuated by all treatments, of which VCO was the most effective. Control mice administered with LLA demonstrated lower liver TC and LDL, but higher plasma TC and HDL compared to controls. Lowest BW gain and food intake were found in mice treated with LLA. In conclusion, VCO, MCT, and LLA ameliorated hepatic histopathology caused by HF. VCO and MCT improved liver lipid profiles, whereas LLA has more beneficial effect on plasma lipids via a better TC:HDL ratio and showed promise for BW control.

Incrementing MCT Character of Coconut Oil Using Enzyme Catalyzed Interesterification.

The fatty acid composition of coconut oil was modified using enzyme catalyzed interesterification with the aim of obtaining a product more alike to commercial MCT oils. This modification was carried out with the aim to obtain a product with some of the health benefits shown by MCT oils. Initially, lipase B from Candida antarctica immobilized on acrylic resin and lipozyme TL IM were tested as enzyme catalysts for the reaction. The enzyme catalysts have shown similar performance and lipozyme TL IM has been chosen as the catalyst based on its lower cost. The effects of reaction time, oil to methyl octanoate ratio, and enzyme loading on the reaction performance have been investigated with response surface methodology (RSM) utilizing the Box-Behnken approach. The optimized reaction was scaled up to 20 g. The possibility to source the medium chain fatty acid esters from coconut oil fatty acid distillate using a simple procedure was demonstrated and the possibility to use these esters for the interesterification of coconut oil has been demonstrated as well.