JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 65 No 3 (2020): Journal of the Chilean Chemical Society
Original Research Papers

CONVERSION OF LINOLEIC ACID TO DIFFERENT FATTY ACID METABOLITES BY LACTOBACILLUS PLANTARUM 13-3 AND IN SILICO CHARACTERIZATION OF THE PROMINENT REACTIONS

Tariq Aziz
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing, China
Abid Sarwar
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing, China
Muhammad Fahim
Center of Omic sciences, Islamia College University Peshawar, KP, Pakistan, 25120
Sam Al Dalali
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing, China
Zia Ud Din
Department of Chemistry Universidade Federeal de Sao Carlos, SP, Brazil
Jalal Ud Din
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing, China
Taicia Pacheco Fill
Institute of Chemistry Universidade Estadual de Campinas, SP, Brazil
Yang Zhennai
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology and Business University, Beijing, China
Published September 10, 2020
Keywords
  • Lactobacillus plantarum,
  • fatty acid metabolites,
  • Linoleate isomerase,
  • Acetoacetate decarboxylase,
  • Dehydrogenase,
  • in silico study
  • ...More
    Less

Abstract

1352-Image-3971-1-11-20191213.jpgLactobacillus plantarum strains have been extensively used in food processing and preservation. L. plantarum also has the potential to convert polyunsaturated fatty acids, e.g. linoleic acid (LA) into bioactive and less toxic fatty acid metabolites. The objective of this study was to assess the capability of probiotic L. plantarum 13-3 to convert Linoleic Acid (LA) to different fatty acid metabolites in the medium supplemented with differential concentrations of LA, and the relevant reactions were characterized by in silico calculation. L. plantarum 13-3 was grown in MRS medium containing LA from 1% to 10%, and the fatty acid metabolites formed in the medium were identified and quantitated by GC-MS and in silico studies were done to confirm the enzymatic reactions involved in its conversion. The results showed that L. plantarum 13-3 could convert LA at different concentrations to 5 different fatty acid metabolites i.e, (Z)-Ethyl heptadec-9-enoate, 9,12-Octadecadienoic acid (Z, Z), methyl ester, Octadec-9-enoic acid, cis-11,14-Eicosadienoic acid, methyl ester and (Z)-18-Octadec-9-enolide. Among these metabolites, the formation of an long chain fatty acid Octadec-9-enoic Acid, also known as 18:1, N-9 or Delta(9)-Octadecenoic acid, is classified as a member of the Long-chain fatty acids in media supplemented with 4% to 10% LA, is being reported for the first time. Putative candidate enzymes involved in biotransformation of LA into fatty acid metabolites were identified in whole genome of L. plantarum 13-3, sequenced previously. In silico studies confirmed that several enzymes including the linoleate isomerase, acetoacetate decarboxylase and oxidoreductase may be involved in biotransformation of LA into fatty acid metabolites. These enzymes could effectively bind the LA molecule mainly by forming hydrogen bonding between the acidic groups of LA and the proline residues at the active sites of the enzymes validating the putative reacting partners.

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