Synthesis of medium-chain length capsinoids from coconut oil catalyzed by Candida rugosa lipases

Jovana Trbojević Ivić; Nenad Milosavić; Aleksandra Dimitrijević; Marija Gavrović Jankulović; Dejan Bezbradica; Dušan Kolarski; Dušan Veličković

doi:10.1016/j.foodchem.2016.09.049

Synthesis of medium-chain length capsinoids from coconut oil catalyzed by Candida rugosa lipases

Food Chem. 2017 Mar 1:218:505-508. doi: 10.1016/j.foodchem.2016.09.049. Epub 2016 Sep 9.

Authors

Jovana Trbojević Ivić¹, Nenad Milosavić², Aleksandra Dimitrijević³, Marija Gavrović Jankulović⁴, Dejan Bezbradica⁵, Dušan Kolarski⁶, Dušan Veličković⁴

Affiliations

¹ Innovation Center, Faculty of Chemistry, University of Belgrade, 11000 Belgrade, Serbia.
² Division of Experimental Therapeutics, Department of Medicine, Columbia University, 10032 New York, NY, United States. Electronic address: nm2729@cumc.columbia.edu.
³ Department of Molecular Biology and Biochemistry, University of California Irvine, 92697 Irvine, CA, United States.
⁴ Department of Biochemistry, Faculty of Chemistry, University of Belgrade, 11000 Belgrade, Serbia.
⁵ Department of Biochemical Engineering and Biotechnology, Faculty of Technology and Metallurgy, University of Belgrade, 11000 Belgrade, Serbia.
⁶ Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborg 4, 9747 AG Groningen, The Netherlands.

PMID: 27719942
DOI: 10.1016/j.foodchem.2016.09.049

Abstract

A commercial preparation of Candida rugosa lipases (CRL) was tested for the production of capsinoids by esterification of vanillyl alcohol (VA) with free fatty acids (FA) and coconut oil (CO) as acyl donors. Screening of FA chain length indicated that C8-C12 FA (the most common FA found in CO triglycerides) are the best acyl-donors, yielding 80-85% of their specific capsinoids. Hence, when CO, which is rich in these FA, was used as the substrate, a mixture of capsinoids (vanillyl caprylate, vanillyl decanoate and vanillyl laurate) was obtained. The findings presented here suggest that our experimental method can be applied for the enrichment of CO with capsinoids, thus giving it additional health promoting properties.

Keywords: Candida rugosa lipases; Capsinoids; Coconut oil; Esterification; Vanillyl alcohol.

MeSH terms

Benzyl Alcohols / metabolism
Biocatalysis*
Candida / enzymology*
Capsaicin / analogs & derivatives*
Capsaicin / metabolism
Coconut Oil
Fatty Acids / metabolism
Lipase / metabolism*
Plant Oils / metabolism*

Substances

Benzyl Alcohols
Fatty Acids
Plant Oils
Lipase
Coconut Oil
Capsaicin
vanillyl alcohol