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Bioscience, Biotechnology, and Biochemistry Volume 67, 2003 - Issue 6
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Original Articles

Purification of Conjugated Linoleic Acid Isomers through a Process Including Lipase-catalyzed Selective Esterification

Toshihiro NAGAOOsaka Municipal Technical Research Institute1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan
,
Yoshie YAMAUCHI-SATORinoru Oil Mills Co., Ltd.2-13-12 Nihonbashi, Chuo-ku, Tokyo 103-0027, Japan
,
Akio SUGIHARAFaculty of Engineering, Tokushima Bunri University1314-1 Sido, Sanuki, Kagawa 769-2101, Japan
,
Toshio IWATARinoru Oil Mills Co., Ltd.2-13-12 Nihonbashi, Chuo-ku, Tokyo 103-0027, Japan
,
Koji NAGAODepartment of Applied Biological Sciences, Saga University1 Honjo-machi, Saga 840-8502, Japan
,
Teruyoshi YANAGITADepartment of Applied Biological Sciences, Saga University1 Honjo-machi, Saga 840-8502, Japan
,
Shuji ADACHIDivision of Food Science and Biotechnology, Graduate School of Agriculture, Kyoto UniversitySakyo-ku, Kyoto 606-8502, Japan
&
Yuji SHIMADAOsaka Municipal Technical Research Institute1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan
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Pages 1429-1433 | Received 16 Dec 2002, Accepted 24 Feb 2003, Published online: 22 May 2014

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Yu-Ming WANG, Koji NAGAO, Nao INOUE, Yoko UJINO, Yuji SHIMADA, Toshihiro NAGAO, Toshio IWATA, Takeshi KAMEGAI, Yoshie YAMAUCHI-SATO & Teruyoshi YANAGITA. (2006) Isomer-Specific Anti-Obese and Hypolipidemic Properties of Conjugated Linoleic Acid in Obese OLETF Rats. Bioscience, Biotechnology, and Biochemistry 70:2, pages 355-362.
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Articles from other publishers (32)

Zhigang Li, Yinglin Fang, Jiawei Yang, Huayong Chen, Bo Yang & Yonghua Wang. (2023) A green and efficient two-step enzymatic esterification-hydrolysis method for enrichment of c9,t11-CLA isomer based on a three-liquid-phase system. RSC Advances 13:38, pages 26690-26699.
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Yu Fujita, Kuniyuki Kano, Shigenobu Kishino, Toshihiro Nagao, Xuefeng Shen, Chiharu Sato, Hatsune Hatakeyama, Yume Ota, Sho Niibori, Ayako Nomura, Kota Kikuchi, Wataru Yasuno, Sho Takatori, Kazunori Kikuchi, Yoshitake Sano, Taisuke Tomita, Toshiharu Suzuki, Junken Aoki, Kun Zou, Shunji Natori & Hiroto Komano. (2021) Dietary cis-9, trans-11-conjugated linoleic acid reduces amyloid β-protein accumulation and upregulates anti-inflammatory cytokines in an Alzheimer’s disease mouse model. Scientific Reports 11:1.
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Claudia G. Morales-Olvera, Cristell A. Sánchez-Pérez, Varenka J. Barbero-Becerra, Eva Juárez-Hernández, Misael Uribe & Norberto C. Chávez-Tapia. 2021. Bioactive Natural Products. Bioactive Natural Products 263 297 .
Khin Nyein Ei San, Ye Fan, Yun Fang, Yongmei Xia & Lin Ma. (2020) A Soap‐Free Strategy for One‐Pot Synthesizing Conjugated Linoleic Acid: Alkali Isomerization of Linoleic Acid through Preferential Esterification Pathway. Journal of the American Oil Chemists' Society 97:9, pages 1021-1028.
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Jose Cordoba-Chacon, Dhavamani Sugasini, Poorna C.R. Yalagala, Apoorva Tummala, Zachary C. White, Toshihiro Nagao, Rhonda D. Kineman & Papasani V. Subbaiah. (2019) Tissue-dependent effects of cis-9,trans-11- and trans-10,cis-12-CLA isomers on glucose and lipid metabolism in adult male mice. The Journal of Nutritional Biochemistry 67, pages 90-100.
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Jiwon Kim, Min-Yu Chung, Hee-Don Choi, In-Wook Choi, In-Hwan Kim, Hyang Sook Chun & Byung Hee Kim. (2017) Selective Enrichment of Conjugated Linoleic Acid Isomers in Their Mixtures Using Combined Chemical and Enzymatic Methods. Journal of the American Oil Chemists' Society 94:4, pages 577-585.
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Hyun Jung Lee, Hyung Joo Suh, Sung Hee Han, Jungil Hong & Hyeon-Son Choi. (2016) Optimization of Extraction of Cycloalliin from Garlic (Allium sativum L.) by Using Principal Components Analysis. Preventive Nutrition and Food Science 21:2, pages 138-146.
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Ingu Kang, Hyo-Jeong Bang, In-Hwan Kim, Hee-Don Choi & Byung Hee Kim. (2015) Synthesis of trans-10,cis-12 conjugated linoleic acid-enriched triacylglycerols via two-step lipase-catalyzed esterification. LWT - Food Science and Technology 62:1, pages 249-256.
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Hyein Park, Song Hwan Bae, Yooheon Park, Hyeon-Son Choi & Hyung Joo Suh. (2015) Lipase-mediated lipid removal from propolis extract and its antiradical and antimicrobial activity. Journal of the Science of Food and Agriculture 95:8, pages 1697-1705.
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Da Som No, Ting Ting Zhao, Yangha Kim, Mi-Ra Yoon, Jeom-Sig Lee & In-Hwan Kim. (2015) Preparation of highly purified pinolenic acid from pine nut oil using a combination of enzymatic esterification and urea complexation. Food Chemistry 170, pages 386-393.
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Kazunori Koba & Teruyoshi Yanagita. (2014) Health benefits of conjugated linoleic acid (CLA). Obesity Research & Clinical Practice 8:6, pages e525-e532.
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Maryam Jafari, Mahdi Kadivar, Sayed Amir Hossein Goli & Mehran Ghiaci. (2013) Optimization of Lipase-Catalyzed Fractionation of Two Conjugated Linoleic Acid (CLA) Isomers. Journal of the American Oil Chemists' Society 91:4, pages 571-578.
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Natalia Niezgoda & Czesław Wawrzeńczyk. (2014) An efficient method for enzymatic purification of cis-9,trans-11 isomer of conjugated linoleic acid. Journal of Molecular Catalysis B: Enzymatic 100, pages 40-48.
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Takashi Kobayashi, Toshihiro Nagao, Yomi Watanabe & Yuji Shimada. (2012) Promotion of the lipase-catalyzed hydrolysis of conjugated linoleic acid l-menthyl ester by addition of an organic solvent. SpringerPlus 1:1.
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Laura Giua, Lina Cossignani, Maria Stella Simonetti, Germana Lombardi & Francesca Blasi. (2012) Candida rugosa lipase selectivity toward trans,cis- and cis,trans-conjugated linoleic acid isomers. European Food Research and Technology 235:1, pages 53-59.
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Delphine Tissot-Favre & Mark Waldron. 2012. Trans Fatty Acids in Human Nutrition. Trans Fatty Acids in Human Nutrition 231 254 .
Takashi Kobayashi, Toshihiro Nagao, Yomi Watanabe & Yuji Shimada. (2011) Direct GC Analysis of the Fatty Acid Compositions of Conjugated Linoleic Acid and Its L-Menthyl Esters. Journal of Oleo Science 60:8, pages 445-448.
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Koji Nagao. (2010) Prevention of the Metabolic Syndrome with Functional Lipids. Nippon Eiyo Shokuryo Gakkaishi 63:1, pages 3-7.
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Wencheng Li, Bo Yang, Yonghua Wang, Dongqing Wei, Chris Whiteley & Xiaoning Wang. (2009) Molecular modeling of substrate selectivity of Candida antarctica lipase B and Candida rugosa lipase towards c9, t11- and t10, c12-conjugated linoleic acid. Journal of Molecular Catalysis B: Enzymatic 57:1-4, pages 299-303.
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Marek Adamczak, Uwe T. Bornscheuer & Włodzimierz Bednarski. (2008) Properties and biotechnological methods to produce lipids containing conjugated linoleic acid. European Journal of Lipid Science and Technology 110:6, pages 491-504.
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Koji Nagao & Teruyoshi Yanagita. (2008) Bioactive lipids in metabolic syndrome. Progress in Lipid Research 47:2, pages 127-146.
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Yong-hua Wang, Xing-fang Li, Yan-xian Liang, Bo Yang & Shui-hua Zhang. (2007) Enzymatic fractionation of conjugated linoleic acid isomers by selective esterification. Journal of Molecular Catalysis B: Enzymatic 46:1-4, pages 20-25.
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Csilla Dianóczki, Katalin Recseg, Katalin Kővári & László Poppe. (2007) Convenient enzymatic preparation of conjugated linoleic acid alkyl esters with C6–C22 alcohols. Journal of Molecular Catalysis B: Enzymatic 45:1-2, pages 45-49.
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George J. Piazza, Thomas A. Foglia & Xuebing Xu. 2007. Novel Enzyme Technology for Food Applications. Novel Enzyme Technology for Food Applications 285 313 .
Takashi Kobayashi, Toshihiro Nagao, Yomi Watanabe, Yoshie Yamauchi-Sato, Satoshi Negishi & Vuji Shimada. (2006) Enrichment of CLA isomers by selective esterification with l-menthol using Candida rugosa lipase. Journal of the American Oil Chemists' Society 83:2, pages 93-99.
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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 HouYomi Watanabe, Yuji Shimada & Toshihiro Nagao. 2005. Handbook of Industrial Biocatalysis. Handbook of Industrial Biocatalysis 8-1 8-27 .
Oi-Ming Lai & Casimir AkohYuji Shimada. 2005. Healthful Lipids. Healthful Lipids.
Douglas G. Hayes. (2004) Enzyme-Catalyzed modification of oilseed materials to produce eco-friendly products. Journal of the American Oil Chemists' Society 81:12, pages 1077-1103.
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Praphan Pinsirodom, Yomi Watanabe, Toshihiro Nagao, Akio Sugihara, Takashi Kobayashi & Yuji Shimada. (2004) Critical temperature for production of MAG by esterification of different FA with glycerol using Penicillium camembertii lipase . Journal of the American Oil Chemists' Society 81:6, pages 543-547.
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Casimir C. Akoh, Guan-Chiun Lee & Jei-Fu Shaw. (2004) Protein engineering and applications of Candida rugosa lipase isoforms. Lipids 39:6, pages 513-526.
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Koji Nagao, Nao Inoue, Yu-Ming Wang, Junichi Hirata, Yuji Shimada, Toshihiro Nagao, Toshiro Matsui & Teruyoshi Yanagita. (2003) The 10trans,12cis isomer of conjugated linoleic acid suppresses the development of hypertension in Otsuka Long–Evans Tokushima fatty rats. Biochemical and Biophysical Research Communications 306:1, pages 134-138.
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