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Bioscience, Biotechnology, and Biochemistry Volume 67, 2003 - Issue 1
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Original Articles

Structural Analysis of Conjugated Linoleic Acid Produced by Lactobacillus plantarum, and Factors Affecting Isomer Production

Shigenobu KISHINODivision of Applied Life Sciences, Graduate School of Agriculture, Kyoto University Sakyo-ku, Kyoto 606-8502, Japan
,
Jun OGAWADivision of Applied Life Sciences, Graduate School of Agriculture, Kyoto University Sakyo-ku, Kyoto 606-8502, Japan
,
Akinori ANDODivision of Applied Life Sciences, Graduate School of Agriculture, Kyoto University Sakyo-ku, Kyoto 606-8502, Japan
,
Takashi IWASHITASuntory Institute for Bioorganic Research Shimamoto-cho, Mishima-gun, Osaka 618-8503, Japan
,
Tsuyoshi FUJITASuntory Institute for Bioorganic Research Shimamoto-cho, Mishima-gun, Osaka 618-8503, Japan
,
Hiroshi KAWASHIMAInstitute for Fundamental Research, Suntory Ltd. Shimamoto-cho, Mishima-gun, Osaka 618-0001, Japan
&
Sakayu SHIMIZUDivision of Applied Life Sciences, Graduate School of Agriculture, Kyoto University Sakyo-ku, Kyoto 606-8502, Japan
show all
Pages 179-182 | Received 18 Jun 2002, Accepted 26 Sep 2002, Published online: 22 May 2014

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Michiki Takeuchi, Shigenobu Kishino, Si-Bum Park, Nahoko Kitamura, Hiroko Watanabe, Azusa Saika, Makoto Hibi, Kenzo Yokozeki & Jun Ogawa. (2016) Production of dicarboxylic acids from novel unsaturated fatty acids by laccase-catalyzed oxidative cleavage. Bioscience, Biotechnology, and Biochemistry 80:11, pages 2132-2137.
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Shigenobu KISHINO, Jun OGAWA, Kenzo YOKOZEKI & Sakayu SHIMIZU. (2011) Linoleic Acid Isomerase in Lactobacillus plantarum AKU1009a Proved to Be a Multi-Component Enzyme System Requiring Oxidoreduction Cofactors. Bioscience, Biotechnology, and Biochemistry 75:2, pages 318-322.
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Yumiko Yasui, Rikako Suzuki, Hiroyuki Kohno, Shingo Miyamoto, Fumiaki Beppu, Masashi Hosokawa, Kazuo Miyashita & Takuji Tanaka. (2007) 9trans,11trans Conjugated Linoleic Acid Inhibits the Development of Azoxymethane-Induced Colonic Aberrant Crypt Foci in Rats. Nutrition and Cancer 59:1, pages 82-91.
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Articles from other publishers (40)

Heena Sharma, Guadalupe D. El Rassi, Angie Lathrop, Veneta B. Dobreva, Thiago Sakomoto Belem & Ranjith Ramanathan. (2021) Comparative analysis of metabolites in cow and goat milk yoghurt using GC–MS based untargeted metabolomics. International Dairy Journal 117, pages 105016.
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Themistoklis Venianakis, Christina Oikonomaki, Michael G. Siskos, Panayiotis C. Varras, Alexandra Primikyri, Eleni Alexandri & Ioannis P. Gerothanassis. (2020) DFT Calculations of 1H- and 13C-NMR Chemical Shifts of Geometric Isomers of Conjugated Linoleic Acid (18:2 ω-7) and Model Compounds in Solution. Molecules 25:16, pages 3660.
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Widodo .Ari Surya Suka, Kafaah Estancia, Donny Widianto & Indratiningsih .. (2018) Conjugated Linoleic Acid Synthesis in Milk Fermented with Lactobacillus casei Strain AG. Pakistan Journal of Nutrition 17:11, pages 524-529.
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Susana C. Ribeiro, Catherine Stanton, Bo Yang, R. Paul Ross & Célia C.G. Silva. (2018) Conjugated linoleic acid production and probiotic assessment of Lactobacillus plantarum isolated from Pico cheese. LWT 90, pages 403-411.
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Jun Ogawa, Michiki Takeuchi & Shigenobu Kishino. 2018. Lipid Modification by Enzymes and Engineered Microbes. Lipid Modification by Enzymes and Engineered Microbes 119 137 .
M. Takeuchi, S. Kishino, S.-B. Park, A. Hirata, N. Kitamura, A. Saika & J. Ogawa. (2016) Efficient enzymatic production of hydroxy fatty acids by linoleic acid Δ9 hydratase from Lactobacillus plantarum AKU 1009a . Journal of Applied Microbiology 120:5, pages 1282-1288.
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Cem O. Özer, Birol Kılıç & Gülden Başyiğit Kılıç. (2016) In-vitro microbial production of conjugated linoleic acid by probiotic L. plantarum strains: Utilization as a functional starter culture in sucuk fermentation. Meat Science 114, pages 24-31.
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Michiki Takeuchi, Shigenobu Kishino, Si-Bum Park, Nahoko Kitamura & Jun Ogawa. (2015) Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a. Journal of Molecular Catalysis B: Enzymatic 117, pages 7-12.
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Michiki Takeuchi, Shigenobu Kishino, Akiko Hirata, Si-Bum Park, Nahoko Kitamura & Jun Ogawa. (2015) Characterization of the linoleic acid Δ9 hydratase catalyzing the first step of polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a. Journal of Bioscience and Bioengineering 119:6, pages 636-641.
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Paolo Bergamo, Diomira Luongo, Junki Miyamoto, Ennio Cocca, Shigenobu Kishino, Jun Ogawa, Soichi Tanabe & Mauro Rossi. (2014) Immunomodulatory activity of a gut microbial metabolite of dietary linoleic acid, 10-hydroxy-cis-12-octadecenoic acid, associated with improved antioxidant/detoxifying defences. Journal of Functional Foods 11, pages 192-202.
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Roberto Mazzoli, Francesca Bosco, Itzhak Mizrahi, Edward A. Bayer & Enrica Pessione. (2014) Towards lactic acid bacteria-based biorefineries. Biotechnology Advances 32:7, pages 1216-1236.
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Jun OGAWA & Shigenobu KISHINO. (2014) Novel Functional Lipid Development Based on the Analysis of Gut Microbial Lipid Metabolism. Oleoscience 14:9, pages 375-380.
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Jun Ogawa, Eiji Sakuradani, Shigenobu Kishino, Akinori Ando, Kenzo Yokozeki & Sakayu Shimizu. 2014. Microbial Production. Microbial Production 207 218 .
Shigenobu KishinoMichiki Takeuchi, Si-Bum ParkAkiko Hirata, Nahoko Kitamura, Jun KunisawaHiroshi KiyonoRyo Iwamoto, Yosuke IsobeMakoto AritaHiroyuki AraiKazumitsu Ueda, Jun ShimaSatomi TakahashiKenzo YokozekiSakayu Shimizu & Jun Ogawa. (2013) Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition. Proceedings of the National Academy of Sciences 110:44, pages 17808-17813.
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Brenna A. Black, Chenxing Sun, Yuan Yuan Zhao, Michael G. Gänzle & Jonathan M. Curtis. (2013) Antifungal Lipids Produced by Lactobacilli and Their Structural Identification by Normal Phase LC/Atmospheric Pressure Photoionization–MS/MS. Journal of Agricultural and Food Chemistry 61:22, pages 5338-5346.
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Michiki Takeuchi, Shigenobu Kishino, Kaori Tanabe, Akiko Hirata, Si‐Bum Park, Sakayu Shimizu & Jun Ogawa. (2013) Hydroxy fatty acid production by Pediococcus sp. . European Journal of Lipid Science and Technology 115:4, pages 386-393.
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JOSÉ C ANDRADE, KELLY ASCENÇÃO, PATRICIA GULLÓN, SILVINO M S HENRIQUES, JORGE M S PINTO, TERESA A P ROCHA-SANTOS, ANA CRISTINA FREITAS & ANA MARIA GOMES. (2012) Production of conjugated linoleic acid by food-grade bacteria: A review. International Journal of Dairy Technology 65:4, pages 467-481.
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Jun Ogawa, Eiji Sakuradani, Shigenobu Kishino, Akinori Ando, Kenzo Yokozeki & Sakayu Shimizu. (2012) Polyunsaturated fatty acids production and transformation by Mortierella alpina and anaerobic bacteria . European Journal of Lipid Science and Technology 114:10, pages 1107-1113.
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Yasuhisa Asano & Kathrin Hölsch. 2012. Enzyme Catalysis in Organic Synthesis. Enzyme Catalysis in Organic Synthesis 1607 1684 .
Shigenobu Kishino, Si-Bum Park, Michiki Takeuchi, Kenzo Yokozeki, Sakayu Shimizu & Jun Ogawa. (2011) Novel multi-component enzyme machinery in lactic acid bacteria catalyzing C C double bond migration useful for conjugated fatty acid synthesis. Biochemical and Biophysical Research Communications 416:1-2, pages 188-193.
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Pei Liu, Sheng-rong Shen, Hui Ruan, Qian Zhou, Liu-liu Ma & Guo-qing He. (2011) Production of conjugated linoleic acids by Lactobacillus plantarum strains isolated from naturally fermented Chinese pickles. Journal of Zhejiang University SCIENCE B 12:11, pages 923-930.
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S. Kishino, J. Ogawa, A. Ando, K. Yokozeki & S. Shimizu. (2010) Microbial production of conjugated γ-linolenic acid from γ-linolenic acid by Lactobacillus plantarum AKU 1009a . Journal of Applied Microbiology 108:6, pages 2012-2018.
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Michael C. FlickingerEiji Sakuradani, Jun Ogawa, Shigenobu Kishino, Akinori Ando, Kenzo Yokozeki & Sakayu Shimizu. 2009. Encyclopedia of Industrial Biotechnology. Encyclopedia of Industrial Biotechnology.
Kazunori KOBA. (2010) Physiological Functions of Conjugated Linoleic Acid (CLA) and Its Application to Foods. Oleoscience 10:11, pages 415-422.
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Shigenobu Kishino, Jun Ogawa, Kenzo Yokozeki & Sakayu Shimizu. (2009) Microbial production of conjugated fatty acids. Lipid Technology 21:8-9, pages 177-181.
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Shigenobu Kishino, Jun Ogawa, Kenzo Yokozeki & Sakayu Shimizu. (2009) Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production. Applied Microbiology and Biotechnology 84:1, pages 87-97.
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A. Ando, J. Ogawa, S. Sugimoto, S. Kishino, E. Sakuradani, K. Yokozeki & S. Shimizu. (2009) Selective production of cis -9, trans -11 isomer of conjugated linoleic acid from trans- vaccenic acid methyl ester by Delacroixia coronata . Journal of Applied Microbiology 106:5, pages 1697-1704.
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Elisabetta Schievano, Gabriella Pasini, Giulio Cozzi & Stefano Mammi. (2008) Identification of the Production Chain of Asiago d’Allevo Cheese by Nuclear Magnetic Resonance Spectroscopy and Principal Component Analysis. Journal of Agricultural and Food Chemistry 56:16, pages 7208-7214.
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Yunkyoung Lee. (2008) Isomer specificity of conjugated linoleic acid (CLA): 9E,11E-CLA. Nutrition Research and Practice 2:4, pages 326.
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R. John Wallace, Nest McKain, Kevin J. Shingfield & Estelle Devillard. (2007) Isomers of conjugated linoleic acids are synthesized via different mechanisms in ruminal digesta and bacteria. Journal of Lipid Research 48:10, pages 2247-2254.
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Fumiaki Beppu, Masashi Hosokawa, Leo Tanaka, Hiroyuki Kohno, Takuji Tanaka & Kazuo Miyashita. (2006) Potent inhibitory effect of trans9, trans11 isomer of conjugated linoleic acid on the growth of human colon cancer cells. The Journal of Nutritional Biochemistry 17:12, pages 830-836.
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Jun Ogawa, Shigenobu Kishino, Akinori Ando, Satoshi Sugimoto, Kousuke Mihara & Sakayu Shimizu. (2005) Production of conjugated fatty acids by lactic acid bacteria. Journal of Bioscience and Bioengineering 100:4, pages 355-364.
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Koji Nagao & Teruyoshi Yanagita. (2005) Conjugated fatty acids in food and their health benefits. Journal of Bioscience and Bioengineering 100:2, pages 152-157.
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Ching HouSakayu Shimizu & Jun Ogawa. 2005. Handbook of Industrial Biocatalysis. Handbook of Industrial Biocatalysis 2-1 2-21 .
Takeru Ishige, Kohsuke Honda & Sakayu Shimizu. (2005) Whole organism biocatalysis. Current Opinion in Chemical Biology 9:2, pages 174-180.
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Akinori Ando, Jun Ogawa, Shigenobu Kishino & Sakayu Shimizu. (2004) Conjugated linoleic acid production from castor oil by Lactobacillus plantarum JCM 1551. Enzyme and Microbial Technology 35:1, pages 40-45.
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R Sieber, M Collomb, A Aeschlimann, P Jelen & H Eyer. (2004) Impact of microbial cultures on conjugated linoleic acid in dairy products—a review. International Dairy Journal 14:1, pages 1-15.
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Shigenobu Kishino, Jun Ogawa, Akinori Ando & Sakayu Shimizu. (2003) Conjugated α‐linolenic acid production from α‐linolenic acid by Lactobacillus plantarum AKU 1009a . European Journal of Lipid Science and Technology 105:10, pages 572-577.
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Akinori Ando, Jun Ogawa, Shigenobu Kishino & Sakayu Shimizu. (2003) CLA production from ricinoleic acid by lactic acid bacteria. Journal of the American Oil Chemists' Society 80:9, pages 889-894.
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Sakayu SHIMIZU, Eiji SAKURADANI & Jun OGAWA. (2003) Production of Functional Lipids by Microorganisms. Oleoscience 3:3, pages 129-139,128.
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