Applied Microbiology and Biotechnology

, Volume 103, Issue 17, pp 7151–7160 | Cite as

Role of 10-hydroxy-cis-12-octadecenic acid in transforming linoleic acid into conjugated linoleic acid by bifidobacteria

  • He Gao
  • Bo Yang
  • Catherine Stanton
  • R. Paul Ross
  • Hao Zhang
  • Haiqin ChenEmail author
  • Wei Chen
Applied microbial and cell physiology


10-hydroxy-cis-12 octadecenoic acid (10-HOE) is a type of octadecenoic acid with a hydroxyl on the C10 carbon. It is generated from linoleic acid (LA) catalyzed by linoleate hydratase in lactobacilli, which was initially named as myosin-cross-reactive antigen (MCRA). In lactobacilli, 10-HOE is the first intermediate in the production of conjugated LA (CLA). Although MCRA from bifidobacteria can generate 10-HOE, the precise role of 10-HOE in CLA production in bifidobacteria remains unknown. In the current work, 10-HOE and LA were added to the medium as the substrate both separately and synchronously to analyze their influence on CLA production. Using 10-HOE as the substrate, bifidobacteria were able to generate CLA by first converting it to LA, followed by CLA accumulation. Recombinant MCRA catalyzed the conversion of 10-HOE to LA, indicating that bifidobacterial MCRA can account for the reversible conversion between LA and 10-HOE. This is the first report to demonstrate the precise role of 10-HOE in the process of CLA production among bifidobacteria.


Linoleic acid Conjugated linoleic acid 10-Hydroxy-cis-12-octadecenoic acid Bifidobacterium 


Funding information

This research was funded by the National Natural Science Foundation of China (nos. 31722041, 31801521, 31571810), the Fundamental Research Funds for the Central Universities (nos. JUSRP51702A, JUSRP11733), the national first-class discipline program of Food Science and Technology (JUFSTR20180102), and the Jiangsu Province “Collaborative Innovation Center for Food Safety and Quality Control,” the Postgraduate Research & Practice Innovation Program of Jiangsu Province (KYCX18_1763).

Compliance with ethical standards

This article does not contain any studies with human participants or animals performed by any of the authors.

Conflict of interest

The authors declare that they have no conflict of interest.


  1. Black BA, Sun C, Zhao YY, Ganzle MG, Curtis JM (2013) Antifungal lipids produced by lactobacilli and their structural identification by normal phase LC/atmospheric pressure photoionization-MS/MS. J Agric Food Chem 61:5338–5346. CrossRefGoogle Scholar
  2. Coakley M, Ross RP, Nordgren M, Fitzgerald G, Devery R, Stanton C (2003) Conjugated linoleic acid biosynthesis by human-derived Bifidobacterium species. J Appl Microbiol 94:138–145. CrossRefGoogle Scholar
  3. Jiang J, Bjorck L, Fonden R (1998) Production of conjugated linoleic acid by dairy starter cultures. J Appl Microbiol 85:95–102. CrossRefGoogle Scholar
  4. Kishino S, Takeuchi M, Park SB, Hirata A, Kitamura N, Kunisawa J, Kiyono H, Iwamoto R, Isobe Y, Arita M, Arai H, Ueda K, Shima J, Takahashi S, Yokozeki K, Shimizu S, Ogawa J (2013) Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition. Proc Natl Acad Sci U S A 110:17808–17813. CrossRefGoogle Scholar
  5. Liavonchanka A, Hornung E, Feussner I, Rudolph MG (2006) Structure and mechanism of the Propionibacterium acnes polyunsaturated fatty acid isomerase. Proc Natl Acad Sci U S A 103:2576–2581. CrossRefGoogle Scholar
  6. O’Connell KJ, Motherway MOC, Hennessey AA, Brodhun F, Ross RP, Feussner I, Stanton C, Fitzgerald GF, van Sinderen D (2013) Identification and characterization of an oleate hydratase-encoding gene from Bifidobacterium breve. Bioengineered 4:313–321. CrossRefGoogle Scholar
  7. Ogawa J, Matsumura K, Kishino S, Omura Y, Shimizu S (2001) Conjugated linoleic acid accumulation via 10-hydroxy-12 octadecenoic acid during microaerobic transformation of linoleic acid by Lactobacillus acidophilus. Appl Environ Microbiol 67:1246–1252. CrossRefGoogle Scholar
  8. Peng SS, Deng M-D, Grund AD, Rosson RA (2007) Purification and characterization of a membrane-bound linoleic acid isomerase from Clostridium sporogenes. Enzyme Microb Tech 40:831–839. CrossRefGoogle Scholar
  9. Rosberg-Cody E, Liavonchanka A, Gobel C, Ross RP, O’Sullivan O, Fitzgerald GF, Feussner I, Stanton C (2011) Myosin-cross-reactive antigen (MCRA) protein from Bifidobacterium breve is a FAD-dependent fatty acid hydratase which has a function in stress protection. Biochem 12:9. Google Scholar
  10. Volkov A, Liavonchanka A, Kamneva O, Fiedler T, Goebel C, Kreikemeyer B, Feussner I (2010) Myosin cross-reactive antigen of Streptococcus pyogenes M49 encodes a fatty acid double bond hydratase that plays a role in oleic acid detoxification and bacterial virulence. J Biol Chem 285:10353–10361. CrossRefGoogle Scholar
  11. Yang B, Chen H, Song Y, Chen YQ, Zhang H, Chen W (2013) Myosin-cross-reactive antigens from four different lactic acid bacteria are fatty acid hydratases. Biotechnol Lett 35:75–81. CrossRefGoogle Scholar
  12. Yang B, Chen H, Gu Z, Tian F, Ross RP, Stanton C, Chen YQ, Chen W, Zhang H (2014) Synthesis of conjugated linoleic acid by the linoleate isomerase complex in food-derived lactobacilli. J Appl Microbiol 117 (2):430-439.
  13. Yang B, Chen H, Stanton C, Ross RP, Zhang H, Chen YQ, Chen W (2015) Review of the roles of conjugated linoleic acid in health and disease. J Funct Foods 15:314–325. CrossRefGoogle Scholar
  14. Yang B, Gao H, Stanton C, Ross RP, Zhang H, Chen YQ, Chen H, Chen W (2017a) Bacterial conjugated linoleic acid production and their applications. Prog Lipid Res 68:26–36. CrossRefGoogle Scholar
  15. Yang B, Qi H, Gu Z, Zhang H, Chen W, Chen H, Chen YQ (2017b) Characterization of the triple-component linoleic acid isomerase in Lactobacillus plantarum ZS2058 by genetic manipulation. J Appl Microbiol 123:1263–1273. CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.State Key Laboratory of Food Science and TechnologyJiangnan UniversityWuxiChina
  2. 2.School of Food Science and TechnologyJiangnan UniversityWuxiChina
  3. 3.International Joint Research Centre for Probiotics & Gut HealthJiangnan UniversityWuxiChina
  4. 4.Teagasc Food Research CentreMoorepark, Fermoy, CoCorkIreland
  5. 5.APC Microbiome IrelandUniversity College CorkCorkIreland
  6. 6.Beijing Innovation Centre of Food Nutrition and Human HealthBeijing Technology & Business UniversityBeijingChina

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