Research Progress in the Mechanism of the Biosynthesis of Conjugated Linoleic Acid Isomers in Mil

doi:10.7506/spkx1002-6630-201323068

Abstract

Abstract:

Conjugated linoleic acid (CLA) is a collective term for geometric and positional isomers of linoleic acid with
conjugated double bonds. They have been found to be responsible for many biological properties that are related to human
health. c9,t11-CLA has anti-carcinogenic activity, and t10,c12-CLA seems to be specifically responsible for reducing body
fat and enhancing energy metabolism. CLA occurs naturally in milk fat in a relatively low level. Several CLA isomers such
as c9,t11-CLA and t10,c12-CLA are detected in milk. These CLA isomers are mainly biosynthesized by some bacteria in the
rumen. The structure and functions of CLA, analytical methods for CLA isomers, the composition and biosynthesis pathways
of CLA in milk, methods of enhancing CLA content in milk and microorganisms involved in the biosynthesis of CLA in the
rumen are reviewed in this paper.

Key words: conjugated linoleic acid, isomer, biosynthesis, milk

CLC Number:

TS203.7

FU Jin-heng1，DING Yi-chun2，LI Hai-xing1，CHEN Yan1，LI Chao-bo1，CAO Yu-sheng1，LIU Xiao-hua1,*. Research Progress in the Mechanism of the Biosynthesis of Conjugated Linoleic Acid Isomers in Mil[J]. FOOD SCIENCE, 2013, 34(23): 338-343.

References

[1] CHRISTIE W W, DOBSON G, GUNSTONE F D. Isomers in commercial samples of conjugated linoleic acid[J]. Lipids, 1997, 32:1231.

[2] NAGAO T, YAMAUCHI-SATO Y, SUGIHARA A, et al. Purification of conjugated linoleic acid isomers through a process including lipase-catalyzed selective esterification[J]. Biosci Biotechnol Biochem, 2003, 67(6):1429-1433.

[3] PARK H S, RYU J H, HA Y L, et al. Dietary conjugated linoleic acid (CLA) induces apoptosis of colonic mucosa in 1,2-dimethylhydrazine-treated rats: a possible mechanism of the anticarcinogenic effect by CLA[J]. British Journal of Nutrition, 2001, 86(5):549-555.

[4] PARRA P, SERRA F, PALOU A. Moderate doses of conjugated linoleic acid isomers mix contribute to lowering body fat content maintaining insulin sensitivity and a noninflammatory pattern in adipose tissue in mice[J]. J. Nutr. Biochem. 2010, 21:107-115.

[5] STRINGER D M, ZAHRADKA P, DECLERCQ V C, et al. Modulation of lipid droplet size and lipid droplet proteins by trans-10,cis-12 conjugated linoleic acid parallels improvements in hepatic steatosis in obese, insulin-resistant rats[J]. Biochim Biophys Acta, 2010, 1801:1375-1385.

[6] LI C, WANG J, WANG H, et al. Effect of trans10,cis12-conjugated linoleic acid on glucose consumption of insulin resistance Chang liver cells[J]. J Food Biochem, 2011, 35:1593-1602.

[7] HUANG G D, ZHONG X F, CAO Y S, et al. Antiproliferative effects of conjugated linoleic acid on human colon adenocarcinoma cell line Caco-2[J]. Asia Pac J Clin Nutr, 2007, 16 (S1):432-436.

[8] KIM Y S, KIM S J, OH T W, et al. Differential inhibitory effects of conjugated linoleic acid isomers on mouse forestomach neoplasia induced by benzo(a)pyrene[J]. J Agr Food Chem. 2010, 58(5): 3177-3183.

[9] RAKIB M A, KIM Y S, JANG W J, et al. Attenuation of 12-o-tetradecanoylphorbol-13-acetate (TPA)-induced gap junctional intercellular communication (GJIC) inhibition in MCF-10A cells by c9,t11-conjugated linoleic acid[J]. J Agric Food Chem, 2010, 58:12022-12030.

[10] BARRETT E, ROSS R P, FITZGERALD G F, et al. Rapid screening method for analyzing the conjugated linoleic acid production capabilities of bacterial cultures[J]. Appl Environ Microbiol, 2007, 73:2333-2337.

[11] MARIA R M, COLNAGO L A, FORATO L A, et al. Fast and simple nuclear magnetic resonance method to measure conjugated linoleic acid in beef[J]. J Agric Food Chem, 2010, 58:6562-6564.

[12] YEONHWA P, ALBRIGHT K J, CAI Z Y, et a1. Comparison of methylation procedures for conjugated linoleic acid and artifact formation by commercial (trimethyIsily1) diazomethane[J]. J Agric Food Chem, 2001, 49(3):1158-1164.

[13] OSTROWAK E, DUNSHEA F R, MURALITHARAN M, et a1. Comparison of silver-ion high?performance liquid chromatographic quantification of free and methylated conjugated linoleic acids[J]. Lipids, 2000, 35(10):1147-1153.

[14] LIU X, CAO Y, CHEN Y. Separation of conjugated linoleic acid isomers by cyclodextrin-modified micellar electrokinetic chromatography[J]. J Chromatogr A, 2005, 1095:197-200.

[15] 王腊梅, 陈燕, 刘晓华, 等. 胶束电动色谱法分析奶中两种主要的共轭亚油酸异构体[J]. 天然产物研究与开发, 2011, 23(1):15-19.

[16] KRAMER J K G, CRUZ-HERNANDEZ C, et al. Analysis of conjugated linoleic acid and trans 18:1 isomers in synthetic and animal products[J]. Am J Clin Nutr, 2004, 79(s):1137s-1145s.

[17] RODRIGUEZ-CASTANEDAS J L, PENA-EGIDO M J, GARCIA-MARINO, et al. Quantitative determination of conjugated linoleic acid isomers by silver ion HPLC in ewe milk fat[J]. J Food Compost Anal, 2011, 24:1004-1008.

[18] NUDDA M, MCGUIRE M A, BATTACONE G, et al. Seasonal variation in conjugated linoleic acid and vaccenic acid in milk fat of sheep and its transfer to cheese and ricotta[J]. Journal of Dairy Science, 2005, 88(4):1311-1319.

[19] KEPLER C R, HIRONS K P, MCNEILL J J, et al. Intermediates and products of the biohydrogenation of linoleic acid by Butyrivibrio fibrisolvens[J]. Journal of Biological Chemistry, 1966, 241: 1350-1354.

[20] 王小静. 调控反刍动物消化代谢提高奶中共轭亚油酸及其机理的研究[D]. 南京:南京农业大学, 2007.

[21] LEE Y J, JENKINS T C. Identification of enriched conjugated linoleic acid isomers in cultures of ruminal microorganisms after dosing with 1-13C-linoleic acid[J]. The Journal of Microbiology, 2011,49(4):622-627.

[22] CORL B A, BAUMGARD L H, DWYER D A, et al. The role of △9-desaturase in the production of cis-9,trans-11 CLA[J]. Journal of Nutritional Biochemistry, 2001, 12:622-630.

[23] 刘晓华, 李海星, 陈燕, 等. 瘤胃细菌生物合成共轭亚油酸的累积特性[J]. 食品科学, 2011, 32(17):254-257.

[24] OR-RASHID MM, ALZAHAL O, MEBRIDE BW. Comparative studies on the metabolism of linoleic acid by rumen bacteria, protozoa, and their mixture in vitro[J]. Appl Microbiol Biotechnol. 2011, 89:387-395.

[25] 侯俊财, 刘艳平, 桂仕林, 等. 大豆油对瘤胃培养液中共轭亚油酸及氢化中间产物累积规律的影响[J]. 畜牧兽医学报, 2008, 39(4):449-454.

[26] 杨俊花, 沈向真, 王喜乐, 等. 葵花油和丙酮酸钙对山羊瘤胃消化代谢与瘤胃内反式油酸积累的影响[J]. 南京农业大学学报, 2009, 32(3):164-168.

[27] TORA P G, SHINGFIELD K J, HERVAS G, et al. Effect of fish oil and sunflower oil on rumen fermentation characteristics and fatty acid composition of digesta in ewes fed a high concentrate diet[J]. Journal of Dairy Science, 2010, 93(10):4804-4817.

[28] 尹福泉, 嘎尔迪, 刘瑞芳, 等. 不同油料籽实对奶牛瘤胃液、血浆脂肪酸组成及乳脂CLA 含量的影响[J]. 中国农业科学, 2009, 42(3):1039-1046.

[29] 王丽芳. 添加菊科植物黄花蒿提取物对奶山羊乳中CLA含量影响及机理研究[D]. 呼和浩特:内蒙古农业大学, 2010.

[30] PARK H G, HEO W, KIM S B, et al.Production of conjugated linoleic acid (CLA) by Bifidobacterium breve LMC520 and its compatibility with CLA-producing rumen bacteria[J]. J Agric Food Chem, 2011, 59(3):984-988.

[31] KHANAL R C, DHIMAN T R, URE A L, et al. Consumer acceptability of conjugated linoleic acid-enriched milk and cheddar cheese from cows grazing on pasture[J]. Journal of Dairy Science, 2005, 88(5):1837-1847.

[32] HUWS S A, LEE M R F, MUETZEL S M, et al. Forage type and fish oil cause shifts in rumen bacterial diversity[J]. FEMS Microbiol Ecol, 2010, 73:396-407.

[33] HUGHES P E, HUNTER W J, TOVE S B. Biohydrogenation of unsaturated fatty acids : purification and properties of cis-9,trans-11-octadecadienoate reductase[J]. J Biol Chem, 1982, 257(7):3643-3649.

[34] MAIA M R G, CHAUDHARY L C, FIGUERES L, et al. Metabolism of polyunsaturated fatty acids and their toxicity to the microflora of the rumen[J]. Antonie Van Leeuwenhoek, 2007, 91:303-314.

[35] KIM Y J, LIU R H, RYCHLIK J L, et al. The enrichment of a ruminal bacterium (Megasphaera elsdenii YJ-4) that produces the trans-10, cis-12 isomer of conjugated linoleic acid[J]. Journal of Applied Microbiology, 2002, 92:976-982.

[36] WALLACE R J, MCKAIN N, SHINGFIELD K J, et al. Isomers of conjugated linoleic acids are synthesized via different mechanisms in ruminal digesta and bacteria[J]. Journal of Lipid Research, 2007, 48:2247-2254.

[37] MOON C D, PACHECO D M, KELLY W J, et al. Reclassification of Clostridium proteoclasticum as Butyrivibrio proteoclasticus comb. nov., a butyrate-producing ruminal bacterium[J]. Int J Syst Evol Microbiol, 2008, 58:2041-2045.

[38] LIU X H, LI H X, CHEN Y, et al. Method for Screening of Bacterial Strains Biosynthesizing Specific Conjugated Linoleic Acid Isomers[J]. J Agric Food Chem, 2012,60:9705-9710.

[39] 孙国权, 刘国文邢欣, 等. 奶牛瘤胃埃氏巨型球菌的分离鉴定及对乳酸发酵的影响[J]. 中国兽医学报, 2009, 29(9):1115-1119.

[40] 吴凌, 赵明娟, 夏成, 等. 痤疮丙酸杆菌的分离鉴定及其对瘤胃微生物发酵的影响[J]. 微生物学报, 2009, 49(2):168-173.