A novel unsaturated fatty acid hydratase toward C16 to C22 fatty acids from Lactobacillus acidophilus

Abstract

This article is available online at http://www.jlr.org revealed that the metabolites of LA, 10-hydroxy-cis -12-octadecenoic acid and 13-hydroxy-cis -9-octadecenoic acid, were detected at higher levels in the intestines of specifi c pathogen-free (SPF) mice than in those of germ-free mice, indicating that gastrointestinal microbes play a role in modifying the FA profi le of their host mice.The physiological functions of 10-hydroxy FAs and their derivatives begin to become clear. 10-Hydroxy-cis -12-octadecenoic acid ameliorates intestinal epithelial barrier impairment via the G protein-coupled receptor 40 (GPR40)-MAPK/ERK kinase (MEK)-ERK pathway and may be useful in the treatment of tight junction-related disorders such as infl ammatory bowel disease ( 3 ). 10-Oxo-cis -12-octadecenoic acid potently activates PPAR ␥ , a master regulator of adipocyte differentiation, and may be involved in the regulation of host energy metabolism ( 5 ).The production of 10-hydroxy-cis -12-octadecenoic acid from LA has been reported in many bacteria, including Lactobacillus acidophilus ( 7 ), L. plantarum ( 8, 9 ), Streptococcus bovis ( 10 ), and Stenotrophomonas nitritireducens ( 11 ). In our previous study, we reported that the enzyme linoleic acid hydratase (CLA-HY) from L. plantarum AKU 1009a catalyzes the hydration of the cis -9 double bond in C16 and C18 FAs, forming the corresponding 10-hydroxy FAs ( 12 ). Volkov et al. ( 13 ) reported that SPH, a hydratase from Streptococcus pyogenes M49, is a myosin-cross-reactive antigen (MCRA) family protein that catalyzes the hydration of the cis-9 and cis -12 double bonds in C16 and C18 FAs, forming the corresponding 10-hydroxy and 10,13-dihydroxy FAs.The production of 13-hydroxy-cis -9-octadecenoic acid from LA has also been reported in some anaerobic bacteria. Hudson et al. ( 10 ) reported that a ruminant bacterium, S. bovis JB1, converts LA into 13-hydroxy-cis -9-octadecenoic acid, and Kishimoto et al. ( 14 ) reported that L. acidophilus Abstract Hydroxy FAs, one of the gut microbial metabolites of PUFAs, have attracted much attention because of their various bioactivities. The purpose of this study was to identify lactic acid bacteria with the ability to convert linoleic acid (LA) to hydroxy FAs. A screening process revealed that a gut bacterium, Lactobacillus acidophilus NTV001, converts LA mainly into 13-hydroxy-cis -9-octadecenoic acid and resulted in the identifi cation of the hydratase responsible, fatty acid hydratase 1 (FA-HY1) . Recombinant FA-HY1 was purifi ed, and its enzymatic characteristics were investigated. FA-HY1 could convert not only C18 PUFAs but also C20 and C22 PUFAs. C18 PUFAs with a cis carbon-carbon double bond at the ⌬ 12 position were converted into the corresponding 13-hydroxy FAs. Arachidonic acid and DHA were converted into the corresponding 15-hydroxy FA and 14-hydroxy FA, respectively. To the best of our knowledge, this is the fi rst report of a bacterial FA hydratase that can convert C20 and C22 PUFAs into the corresponding hydroxy FAs. These novel ...

658 Marine Omega-3 Polyunsaturated Fatty Acid Intake and Survival After Colorectal Cancer Diagnosis

“…Furthermore, although there are differences in the likelihood of use of adjuvant chemotherapy based on the factors such as socioeconomic status, the fairly homogenous nature of participants (health professionals) would likely increase the probability of at least standard therapy. [39,40] Comorbidities and access to health care may also confound our findings; however, given the population studied, we would expect the latter to be diminished. Moreover, although comorbidities have may influence overall survival, [41,42] such diseases are less likely to affect CRC-specific mortality, [43] the primary endpoint of this study.…”

On the current role of hydratases in biocatalysis

“…NRRL-2994 and Saccharomyces cerevisiae was ranging from 82 to 98%, while Nocardia aurantia ATCC 12674 only produced enantiomeric mixtures of ( R )- and ( S )-10-HSA (Yang et al 1993). For isolated FAHs, excellent ee values were reported in the case of OhyA (ee of 98% for ( R )-10-HSA from OA) (Engleder et al 2015), CLA-HY (ee > 99.9% for ( S )-10-hydroxy fatty acids from LA, α- and γ-linolenic acid (LnA) (Takeuchi et al 2014) and FA-HY1 from L. acidophilus NTV001 (ee > 99% for ( R )-13-hydroxy fatty acids from LA and α-LnA) (Hirata et al 2015). Contrary to the S. cerevisiae -mediated production of 10-HSA from OA (el-Sharkawy et al 1992; Yang et al 1993), more recent investigations are pointing towards hydration of OA by bacterial contaminants of employed yeast preparations (Brunner and Hintermann 2016; Serra and De Simeis 2017).…”

Engineering and application of enzymes for lipid modification, an update

“…Oh and coworkes, however, have identified a new ∆12-hydratase from Lactobacillus acidophilus, which predominantly forms the 13-hydroxy derivative of linoleic acid [133,134]. In addition, Hirata and coworkers showed that the ∆12-hydratase from Lactobacillus not only converts C18 cis PUFAs, but also arachidonic acid (C20) and DHA (C22) into the corresponding 15-hydroxy fatty acid and the14-hydroxy fatty acids, respectively [135]. Moreover, recent reports on ∆9 hydratases processes with recombinant enzymes underline their potential applicability for the large-scale production of 10-hydroxy fatty acids derivatives.…”