Key points are not available for this paper at this time.
The PUFAs include many bioactive lipids. The microbial metabolism of C18 PUFAs is known to produce their bioactive isomers, such as conjugated FAs and hydroxy FAs, but there is little information on that of C20 PUFAs. In this study, we aimed to obtain anaerobic bacteria with the ability to produce novel PUFAs from C20 PUFAs. Through the screening of ∼100 strains of anaerobic bacteria, Clostridium bifermentans JCM 1386 was selected as a strain with the ability to saturate PUFAs during anaerobic cultivation. This strain converted arachidonic acid (cis-5,cis-8,cis-11,cis-14-eicosatetraenoic acid) and EPA (cis-5,cis-8,cis-11,cis-14,cis-17-EPA) into cis-5,cis-8,trans-13-eicosatrienoic acid and cis-5,cis-8,trans-13,cis-17-eicosatetraenoic acid, giving yields of 57% and 67% against the added PUFAs, respectively. This is the first report of the isolation of a bacterium transforming C20 PUFAs into corresponding non-methylene-interrupted FAs. We further investigated the substrate specificity of the biohydrogenation by this strain and revealed that it can convert two cis double bonds at the ω6 and ω9 positions in various C18 and C20 PUFAs into a trans double bond at the ω7 position. This study should serve to open up the development of novel potentially bioactive PUFAs. The PUFAs include many bioactive lipids. The microbial metabolism of C18 PUFAs is known to produce their bioactive isomers, such as conjugated FAs and hydroxy FAs, but there is little information on that of C20 PUFAs. In this study, we aimed to obtain anaerobic bacteria with the ability to produce novel PUFAs from C20 PUFAs. Through the screening of ∼100 strains of anaerobic bacteria, Clostridium bifermentans JCM 1386 was selected as a strain with the ability to saturate PUFAs during anaerobic cultivation. This strain converted arachidonic acid (cis-5,cis-8,cis-11,cis-14-eicosatetraenoic acid) and EPA (cis-5,cis-8,cis-11,cis-14,cis-17-EPA) into cis-5,cis-8,trans-13-eicosatrienoic acid and cis-5,cis-8,trans-13,cis-17-eicosatetraenoic acid, giving yields of 57% and 67% against the added PUFAs, respectively. This is the first report of the isolation of a bacterium transforming C20 PUFAs into corresponding non-methylene-interrupted FAs. We further investigated the substrate specificity of the biohydrogenation by this strain and revealed that it can convert two cis double bonds at the ω6 and ω9 positions in various C18 and C20 PUFAs into a trans double bond at the ω7 position. This study should serve to open up the development of novel potentially bioactive PUFAs. The PUFAs include many bioactive lipids that play an important role in the maintenance of biological functions in mammals (1Benatti P. Peluso G. Nicolai R. Calvani M. Polyunsaturated fatty acids: biochemical, nutritional and epigenetic properties.J. Am. Coll. Nutr. 2004; 23: 281-302Crossref PubMed Scopus (317) Google Scholar, 2Spector A.A. Essentiality of fatty acids.Lipids. 1999; 34: S1-S3Crossref PubMed Google Scholar). The vast majority of PUFAs have two or more cis double bonds that are separated from each other by a single methylene group (known as methylene-interrupted FAs). They include two major subgroups (the ω3 and ω6 PUFAs) that have different functions (1Benatti P. Peluso G. Nicolai R. Calvani M. Polyunsaturated fatty acids: biochemical, nutritional and epigenetic properties.J. Am. Coll. Nutr. 2004; 23: 281-302Crossref PubMed Scopus (317) Google Scholar, 2Spector A.A. Essentiality of fatty acids.Lipids. 1999; 34: S1-S3Crossref PubMed Google Scholar, 3Lands W.E. Stories about acyl chains.Biochim. Biophys. Acta. 2000; 1483: 1-14Crossref PubMed Scopus (123) Google Scholar). Arachidonic acid cis-5,cis-8,cis-11,cis-14-eicosatetraenoic acid (20:4, ω6), AA, which is the C20 PUFA of the ω6 class and is made from linoleic acid cis-9,cis-12-octadecadienoic acid (18:2, ω6), LA, is involved in many cellular signaling mechanisms and is also the precursor for the formation of the 2 series of prostaglandins. On the other hand, EPA cis-5,cis-8,cis-11,cis-14,cis-17-EPA (20:5, ω3), which is a C20 PUFAs of the ω3 class and is made from α-linolenic acid cis-9,cis-12,cis-15-octadecatrienoic acid (18:3, ω3), is the precursor for the formation of the 3 series of prostaglandins and can compete with the effects of AA, such as the AA conversion to the prostaglandins. Unlike methylene-interrupted FAs, rare isomers of PUFAs, which have at least two double bonds that are separated by a single carbon-carbon bond (known as conjugated FAs) (4Kepler C.R. Hirons K.P. McNeill J.J. Tove S.B. Intermediates and products of the biohydrogenation of linoleic acid by Butyrinvibrio fibrisolvens.J. Biol. Chem. 1966; 241: 1350-1354Abstract Full Text PDF PubMed Google Scholar, 5Wilde P.F. Dawson R.M. The biohydrogenation of alpha-linolenic acid and oleic acid by rumen micro-organisms.Biochem. J. 1966; 98: 469-475Crossref PubMed Scopus (55) Google Scholar, 6Harfoot C.G. Hazlewood G.P. Lipid metabolism in the rumen.in: Hobson P.N. Stewart C.S. In The Rumen Microbial Ecosystem. Blackie Academic 14: 153-172Crossref PubMed Scopus (143) Google Scholar) or two or more methylene groups known as non-methylene-interrupted FAs (NMIFAs) (8Wolff R.L. Bayard C.C. Fatty acid composition of some pine seed oils.J. Am. Oil Chem. Soc. 1995; 72: 1043-1046Crossref Scopus (89) Google Scholar, 9Houtsmuller U.M. Columbinic acid, a new type of essential fatty acid.Prog. Lipid Res. 1981; 20: 889-896Crossref PubMed Scopus (45) Google Scholar, 10Takagi T. Itabashi Y. cis-5-Olefinic unusual fatty acids in seed lipids of gymnospermae and their distribution in triacylglycerols.Lipids. 1982; 17: 716-723Crossref Scopus (111) Google Scholar), have been found in several materials including plant oil. These rare PUFAs have also been reported to show interesting physiological effects (9Houtsmuller U.M. Columbinic acid, a new type of essential fatty acid.Prog. Lipid Res. 1981; 20: 889-896Crossref PubMed Scopus (45) Google Scholar, 11Sugano M. Ikeda I. Wakamatsu K. Oka T. Influence of Korean pine (Pinus koraiensis)-seed oil containing cis-5,cis-9,cis-12-octadecatrienoic acid on polyunsaturated fatty acid metabolism, eicosanoid production and blood pressure of rats.Br. J. Nutr. 1994; 72: 775-783Crossref PubMed Scopus (81) Google Scholar, 12Lee J.W. Lee K.W. Lee S.W. Kim I.H. Rhee C. Selective increase in pinolenic acid (all-cis-5,9,12–18:3) in Korean pine nut oil by crystallization and its effect on LDL-receptor activity.Lipids. 2004; 39: 383-387Crossref PubMed Scopus (50) Google Scholar, 13Berger A. German J.B. Extensive incorporation of dietary delta-5,11,14 eicosatrienoate into the phosphatidylinositol pool.Biochim. Biophys. Acta. 1991; 1085: 371-376Crossref PubMed Scopus (41) Google Scholar, 14Pariza M.W. Park Y. Cook M.E. The biologically active isomers of conjugated linoleic acid.Prog. Lipid Res. 2001; 40: 283-298Crossref PubMed Scopus (916) Google Scholar, 15Toomey S. McMonagle J. Roche H.M. Conjugated linoleic acid: a functional nutrient in the different pathophysiological components of the metabolic syndrome?.Curr. Opin. Clin. Nutr. Metab. Care. 2006; 9: 740-747Crossref PubMed Scopus (27) Google Scholar). Therefore, they have gained considerable attention, but natural sources rich in them are limited. The partial hydrogenation of PUFAs is the process of converting PUFAs into the more saturated FAs and can produce NMIFAs from more readily available PUFAs. This can be performed mainly by chemical hydrogenation in industry and by microbial biohydrogenation in living organisms (16Menaa F. Menaa A. Tréton J. Menaa B. Technological approaches to minimize industrial trans fatty acids in foods.J. Food Sci. 2013; 78: R377-R386Crossref PubMed Scopus (31) Google Scholar). Chemical partial hydrogenation is widely used to convert vegetable oils into foods such as margarine. The partial hydrogenation of vegetable oils produces various hydrogenated vegetable oils, including several isomers of octadecenoic acid (18:1), depending on the reaction conditions. In contrast, microbial biohydrogenation can selectively produce specific isomers (4Kepler C.R. Hirons K.P. McNeill J.J. Tove S.B. Intermediates and products of the biohydrogenation of linoleic acid by Butyrinvibrio fibrisolvens.J. Biol. Chem. 1966; 241: 1350-1354Abstract Full Text PDF PubMed Google Scholar, 5Wilde P.F. Dawson R.M. The biohydrogenation of alpha-linolenic acid and oleic acid by rumen micro-organisms.Biochem. J. 1966; 98: 469-475Crossref PubMed Scopus (55) Google Scholar, 6Harfoot C.G. Hazlewood G.P. Lipid metabolism in the rumen.in: Hobson P.N. Stewart C.S. In The Rumen Microbial Ecosystem. Blackie Academic 14: 153-172Crossref PubMed Scopus (143) Google Scholar). Thus, microbial biohydrogenation has several advantages over chemical hydrogenation. Recently, some studies, including ours, have found that many anaerobic bacteria, such as Lactobacillus species, can produce conjugated LAs from LA (4Kepler C.R. Hirons K.P. McNeill J.J. Tove S.B. Intermediates and products of the biohydrogenation of linoleic acid by Butyrinvibrio fibrisolvens.J. Biol. Chem. 1966; 241: 1350-1354Abstract Full Text PDF PubMed Google Scholar, 17Mosley E.E. Powell G.L. Riley M.B. Jenkins T.C. Microbial biohydrogenation of oleic acid to trans isomers in vitro.J. Lipid Res. 2002; 43: 290-296Abstract Full Text Full Text PDF PubMed Google Scholar, 18Jiang J. Björck L. Fondén R. Production of conjugated linoleic acid by dairy starter cultures.J. Appl. Microbiol. 1998; 85: 95-102Crossref PubMed Scopus (251) Google Scholar, 19Coakley M. Ross R.P. Nordgren M. Fitzgerald G. Devery R. Stanton C. Conjugated linoleic acid biosynthesis by human-derived Bifidobacterium species.J. Appl. Microbiol. 2003; 94: 138-145Crossref PubMed Scopus (265) Google Scholar, 20Ogawa J. Kishino S. Ando A. Sugimoto S. Mihara K. Shimizu S. Production of conjugated fatty acids by lactic acid bacteria.J. Biosci. Bioeng. 2005; 100: 355-364Crossref PubMed Scopus (232) Google Scholar). Further, we have revealed that lactic acid bacteria produce unique PUFAs from various C18 PUFAs through partial biohydrogenation (21Kishino S. Ogawa J. Yokozeki K. Shimizu S. Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production.Appl. Microbiol. Biotechnol. 2009; 84: 87-97Crossref PubMed Scopus (54) Google Scholar, 22Kishino S. Ogawa J. Ando A. Yokozeki K. Shimizu S. Microbial production of conjugated gamma-linolenic acid from gamma-linolenic acid by Lactobacillus plantarum AKU 1009a.J. Appl. Microbiol. 2010; 108: 2012-2018Crossref PubMed Scopus (21) Google Scholar, 23Kishino S. Takeuchi M. Park S.B. Hirata A. Kitamura N. Kunisawa J. Kiyono H. Iwamoto R. Isobe Y. Arita M. et al.Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition.Proc. Natl. Acad. Sci. USA. 2013; 110: 17808-17813Crossref PubMed Scopus (243) Google Scholar). Thus, the biohydrogenation of C18 PUFAs has been widely studied. However, as far as we know, the biohydrogenation of other FAs, especially C20 PUFAs, has not been extensively studied so far. In this paper, we report about the screening of anaerobic bacteria for the ability to transform C20 PUFAs through biohydrogenation. We found that Clostridium bifermentans JCM 1386 can specifically convert AA and EPA into their partially saturated FAs with a trans double bond at the ω7 position. We further found that other C18 and C20 PUFAs were also converted in a similar manner. Thus, we succeeded in the production of various C18 and C20 NMIFAs with a trans double bond at the ω7 position through the biohydrogenation by C. bifermentans JCM 1386, leading to the development of novel potentially bioactive PUFAs. LA and α-linolenic acid were purchased from Wako Pure Chemical (Osaka, Japan). γ-Linolenic acid (cis-6,cis-9,cis-12-18:3), dihomo-γ-linolenic acid cis-8,cis-11,cis-14-eicosatrienoic acid (20:3), AA, and EPA were purchased from Sigma (St. Louis, was purchased from Chemical other used were of and are The anaerobic bacteria used for this study were in of of and from other of and The anaerobic bacteria used for this study were from and so The was with AA, or strain was into of the in and in an anaerobic and at for the the was separated into and by and the was used for lipid were from the with to the of of lipid and J. PubMed Scopus Google Scholar) and with at for The were with and by a with a and a and with a Japan). The was and was to at a of and at that for The and were at was used as a at the isolation of the in a of C. bifermentans JCM 1386 with AA its were by at and a with a Japan). The was at a of and the of The containing was further by on with C18 Japan). was used as the at a of the isolation of the in a of C. bifermentans JCM 1386 with EPA its were a as for that the used for the was at a of The chemical of FAs were by effect and were performed on a for and chemical were to the were by of the with acid in for at by to the of and for of the position of the double bond in fatty acids.Lipids. 9: PubMed Scopus Google Scholar). The was with and over and the was by a in a with a was used for The of the and the was performed on an at was used in the at with a of was used with the at were performed on the acids of the FAs with a The was and the was 3 was used for the The ability of anaerobic bacteria to convert the C20 PUFAs of EPA and AA during was investigated with LA as a of C18 We ∼100 including the bacteria, which to such as and so on and the The of the PUFAs were by with the of the on bacteria, two strains of C. bifermentans 1386 and JCM the to convert AA and strains the two C20 strains to the of Clostridium and were found to have the ability to convert LA to acid for the ability of transforming from from from were in with of AA, or of EPA for 3 as in and not in a new were in with of AA, or of EPA for 3 as in and not the of FAs by C. bifermentans JCM 1386 from AA, and LA as C. bifermentans JCM 1386 was with AA or FAs from AA and from EPA were on the of FAs. The were C. bifermentans JCM was with AA or EPA However, C. JCM C. JCM and P. JCM not convert AA and the of the C20 PUFAs added C. bifermentans C. bifermentans JCM not C. bifermentans was used for further the lipids from the of C. bifermentans JCM 1386 with AA were by lipids were in the not of the the were and used for The of the of a of that is C20 PUFA containing double The by of the of was by and The and were from single bonds and as from the The and from the of single bonds the and positions from the double bonds were On the of the of was as the isomers of also that is an of The of the of double bonds in The of the from the of the was and or and on the of in The was as the by the of a and but not and in was to the of double The and and and that the two double bonds of the and positions are in the cis and that the position is in the trans On the of the of the was as of the of and The are in The effect are in the lipids from the of C. bifermentans JCM 1386 with EPA were by lipids were in the not of the the were and used for The of the of a of This that is C20 PUFA containing double The by of the of was by and The and were from the of single bonds and as from The and from the of single bonds the and positions from the double bonds were On the of the of was as the isomers of also that is an of The of and the of double bonds in The of the from the of the was and on the of and revealed that the and and and and and and that the double bonds of the and position are in cis and that the double bond of the position is in the trans On the of the of the was as of AA and EPA on their by C. bifermentans were investigated various of AA were added to the the of production with of AA up to giving a of 57% against the added AA various of EPA were added to the the of production with of EPA up to giving a of 67% against the added EPA However, C. bifermentans JCM 1386 more EPA was the substrate specificity of PUFA during the of C. bifermentans JCM 1386, of α-linolenic acid, acid, dihomo-γ-linolenic acid, AA, and were added to the C. bifermentans JCM 1386 convert AA, α-linolenic acid, acid, and dihomo-γ-linolenic acid, but not The products from α-linolenic acid, acid, and dihomo-γ-linolenic acid were by The of of the from α-linolenic acid a of and of and and and that this is a C18 PUFA with double bonds at the ω3 and ω7 positions The of the from acid a of and of and and and that the is a C18 PUFA with double bonds at the ω7 and positions The of the from dihomo-γ-linolenic acid a of and of and and and that the is a C20 PUFA with double bonds at the ω7 and positions Thus, C. bifermentans JCM 1386 convert C18 and C20 PUFAs with double bonds at the ω6 and ω9 positions into their corresponding NMIFAs by C. bifermentans JCM 1386 of PUFA during of C. bifermentans JCM The on PUFA conversion by anaerobic bacteria have been with the to the of products such as or In the of studies, bacteria, such as (4Kepler C.R. Hirons K.P. McNeill J.J. Tove S.B. Intermediates and products of the biohydrogenation of linoleic acid by Butyrinvibrio fibrisolvens.J. Biol. Chem. 1966; 241: 1350-1354Abstract Full Text PDF PubMed Google Scholar), Lactobacillus plantarum J. Kishino S. Ando A. Sugimoto S. Mihara K. Shimizu S. Production of conjugated fatty acids by lactic acid bacteria.J. Biosci. Bioeng. 2005; 100: 355-364Crossref PubMed Scopus (232) Google Scholar, S. Ogawa J. Yokozeki K. Shimizu S. Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production.Appl. Microbiol. Biotechnol. 2009; 84: 87-97Crossref PubMed Scopus (54) Google Scholar, 22Kishino S. Ogawa J. Ando A. Yokozeki K. Shimizu S. Microbial production of conjugated gamma-linolenic acid from gamma-linolenic acid by Lactobacillus plantarum AKU 1009a.J. Appl. Microbiol. 2010; 108: 2012-2018Crossref PubMed Scopus (21) Google Scholar, 23Kishino S. Takeuchi M. Park S.B. Hirata A. Kitamura N. Kunisawa J. Kiyono H. Iwamoto R. Isobe Y. Arita M. et al.Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition.Proc. Natl. Acad. Sci. USA. 2013; 110: 17808-17813Crossref PubMed Scopus (243) Google Scholar), and Bifidobacterium M. Ross R.P. Nordgren M. Fitzgerald G. Devery R. Stanton C. Conjugated linoleic acid biosynthesis by human-derived Bifidobacterium species.J. Appl. Microbiol. 2003; 94: 138-145Crossref PubMed Scopus (265) Google Scholar), have been and their metabolic of C18 PUFAs, such as LA and α-linolenic acid, have been However, the ability to transform C20 and PUFAs has not been studied in there have been several that EPA and are hydrogenated in the rumen in P. A. S. S. A. P. et oil the of fatty acids at the and in the in Nutr. PubMed Scopus Google Scholar) and during in with P. and of fatty acid biohydrogenation in containing PubMed Scopus Google Scholar, A.A. Jenkins T.C. of and acids from of Sci. 2004; Full Text Full Text PDF PubMed Scopus Google Scholar). In this study, we found that C. bifermentans JCM 1386 convert AA and EPA into and which are NMIFAs with a trans double bond at the ω7 position This is the first report of the isolation of the bacterium transforming C20 PUFAs into corresponding that similar were with LA this strain can convert two cis double bonds at the ω6 and ω9 positions in PUFAs into a trans double bond at the ω7 position to the trans FAs of the of double bonds at other In similar were also of other C18 and C20 PUFAs acid, acid, and dihomo-γ-linolenic acid) They be converted into the corresponding NMIFAs with a trans double bond at the ω7 position. However, C. bifermentans JCM 1386 not convert that PUFAs not be a substrate for this Thus, we succeeded in the production of various C18 and C20 NMIFAs with a trans double bond at the ω7 position through the biohydrogenation by C. bifermentans JCM NMIFAs are a class of PUFAs that has of their unique and physiological and they have been found in plant acid and acid are C18 NMIFAs that were found in and (8Wolff R.L. Bayard C.C. Fatty acid composition of some pine seed oils.J. Am. Oil Chem. Soc. 1995; 72: 1043-1046Crossref Scopus (89) Google Scholar, 9Houtsmuller U.M. Columbinic acid, a new type of essential fatty acid.Prog. Lipid Res. 1981; 20: 889-896Crossref PubMed Scopus (45) Google Scholar). They are isomers of acid and show various such as the of by of the of blood and essential (9Houtsmuller U.M. Columbinic acid, a new type of essential fatty acid.Prog. Lipid Res. 1981; 20: 889-896Crossref PubMed Scopus (45) Google Scholar, 11Sugano M. Ikeda I. Wakamatsu K. Oka T. Influence of Korean pine (Pinus koraiensis)-seed oil containing cis-5,cis-9,cis-12-octadecatrienoic acid on polyunsaturated fatty acid metabolism, eicosanoid production and blood pressure of rats.Br. J. Nutr. 1994; 72: 775-783Crossref PubMed Scopus (81) Google Scholar, 12Lee J.W. Lee K.W. Lee S.W. Kim I.H. Rhee C. Selective increase in pinolenic acid (all-cis-5,9,12–18:3) in Korean pine nut oil by crystallization and its effect on LDL-receptor activity.Lipids. 2004; 39: 383-387Crossref PubMed Scopus (50) Google Scholar). acid is a C20 that was found in oil T. Itabashi Y. cis-5-Olefinic unusual fatty acids in seed lipids of gymnospermae and their distribution in triacylglycerols.Lipids. 1982; 17: 716-723Crossref Scopus (111) Google Scholar). has been reported to show a in the AA in the phosphatidylinositol of A. German J.B. Extensive incorporation of dietary delta-5,11,14 eicosatrienoate into the phosphatidylinositol pool.Biochim. Biophys. Acta. 1991; 1085: 371-376Crossref PubMed Scopus (41) Google Scholar), which functions in such as in the A. German J.B. Extensive incorporation of dietary delta-5,11,14 eicosatrienoate into the phosphatidylinositol pool.Biochim. Biophys. Acta. 1991; 1085: 371-376Crossref PubMed Scopus (41) Google Scholar, of Rev. 2001; PubMed Scopus Google Scholar). that PUFAs show an novel NMIFAs are to show novel interesting physiological several natural plant oils have a of PUFAs with a double bond at the ω7 position G. J. Metabolic of can of fatty acids with the found in natural plant 2010; PubMed Scopus Google Scholar), and the biohydrogenation of PUFAs produces PUFAs with a double bond at the ω7 such as C.G. Hazlewood G.P. Lipid metabolism in the rumen.in: Hobson P.N. Stewart C.S. In The Rumen Microbial Ecosystem. Blackie Academic 14: 153-172Crossref PubMed Scopus (143) Google Scholar). These to that a double bond at the ω7 position a for a biological In this various C18 and C20 NMIFAs in this study be is also that NMIFAs were in Therefore, this study serve to open up the development of novel in the of rare bioactive PUFAs. Lipid metabolism by anaerobic bacteria is an from the of the role of the gut in to of the by a has been to be with of gut composition M. and gut 2006; PubMed Scopus Google Scholar, F. L. is to but in the gut Full Text Full Text PDF PubMed Scopus Google Scholar). are by gut as as by the is that the biohydrogenation of FAs as a in bacteria, and PUFAs especially are more saturated FAs J. Björck L. Fondén R. Production of conjugated linoleic acid by dairy starter cultures.J. Appl. Microbiol. 1998; 85: 95-102Crossref PubMed Scopus (251) Google Scholar, C.S. N. of fatty acids to the Microbiol. 2010; PubMed Scopus Google Scholar). This that the for the biohydrogenation of PUFAs to the of gut bacteria dietary of PUFAs is In the that lipid metabolism by gut the of the host by composition S. Takeuchi M. Park S.B. Hirata A. Kitamura N. Kunisawa J. Kiyono H. Iwamoto R. Isobe Y. Arita M. et al.Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition.Proc. Natl. Acad. Sci. USA. 2013; 110: 17808-17813Crossref PubMed Scopus (243) Google Scholar). Therefore, on lipid metabolism by gut bacteria, including C. bifermentans this and Lactobacillus (21Kishino S. Ogawa J. Yokozeki K. Shimizu S. Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production.Appl. Microbiol. Biotechnol. 2009; 84: 87-97Crossref PubMed Scopus (54) Google Scholar, 22Kishino S. Ogawa J. Ando A. Yokozeki K. Shimizu S. Microbial production of conjugated gamma-linolenic acid from gamma-linolenic acid by Lactobacillus plantarum AKU 1009a.J. Appl. Microbiol. 2010; 108: 2012-2018Crossref PubMed Scopus (21) Google Scholar, 23Kishino S. Takeuchi M. Park S.B. Hirata A. Kitamura N. Kunisawa J. Kiyono H. Iwamoto R. Isobe Y. Arita M. et al.Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition.Proc. Natl. Acad. Sci. USA. 2013; 110: 17808-17813Crossref PubMed Scopus (243) Google Scholar, S. Park S.B. Takeuchi M. Yokozeki K. Shimizu S. Ogawa J. in lactic acid bacteria double bond for conjugated fatty acid Biophys. Res. PubMed Scopus Google Scholar), should serve to and the of the with arachidonic acid linoleic acid non-methylene-interrupted effect acid
Sakurama et al. (Tue,) studied this question.