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Trans-11–18: 1 is effectively δ9-desaturated compared with Trans-12–18: 1 in humans

Published online by Cambridge University Press:  08 March 2007

Katrin Kuhnt ,
Jana Kraft ,
Peter Moeckel  and
Gerhard Jahreis
Katrin Kuhnt
Affiliation:
Institute of Nutrition, Friedrich Schiller University, Jena, Germany
Jana Kraft
Affiliation:
Institute of Nutrition, Friedrich Schiller University, Jena, Germany
Peter Moeckel
Affiliation:
Institute of Nutrition, Friedrich Schiller University, Jena, Germany
Gerhard Jahreis*
Affiliation:
Institute of Nutrition, Friedrich Schiller University, Jena, Germany
*
*Corresponding author: Dr Gerhard Jahreis, fax +49 3641 949612, email Gerhard.Jahreis@uni-jena.de
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Abstract

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The aim of this human intervention study was to evaluate the Δ9-desaturation of trans-11–18:1 (trans-vaccenic acid; tVA) to cis-9,trans-11–18:2 (c9,t11 conjugated linoleic acid; CLA) and of trans-12–18:1 (t12) to cis-9,trans-12–18:2 after a short-term (7d) and a long-term (42d) supplementation period. The conversion rates of both trans-18:1 isomers were estimated by lipid analysis of serum and red blood cell membranes (RBCM). Subjects started with a 2-week adaptation period without supplements. During the 42d intervention period, the diet of the test group was supplemented with 3g/d of tVA and 3g/d of t12. The diet of the control group was supplemented with a control oil. Serum tVA and t12 levels in the test group increased by fivefold and ninefold after 7d, respectively, and by eight- and 12-fold after 42d, respectively, when compared with the adaptation period (p≤0·002). The serum c9,t11CLA levels increased by 1·7- and 2·0-fold after 7d and 42d, respectively (p≤0·001). After 42d, the test group's RBCM c9,t11CLA content was elevated by 20% (p=0·021), whereas in the control group it was decreased by 50% (p=0·002). The conversion rate of tVA was estimated at 24% by serum and 19% by RBCM. No increase in c9,t12–18:2 was observed in the serum and RBCM, and thus no conversion of t12 could be determined. In conclusion, the endogenous conversion of dietary tVA to c9,t11CLA contributes approximately one quarter to the human CLA pool and should be considered when determining the CLA supply.

Keywords

Conjugated linoleic acidstrans-Vaccenic acidtrans-12-181Δ9-DesaturationMan
Type
Research Article
Information
British Journal of Nutrition , Volume 95 , Issue 4 , April 2006 , pp. 752 - 761
Copyright
Copyright © The Nutrition Society 2006

References

Adlof, RO, Duval, S & Emken, EABiosynthesis of conjugated linoleic acid in humans. Lipids (2000) 35, 131–135.CrossRefGoogle ScholarPubMed
Arab, LBiomarkers of fat and fatty acid intake. J Nutr (2003) 133, 925S–932S.CrossRefGoogle ScholarPubMed
Aro, A, Kosmeijeir-Schuil, T, van den Bovenkamp, P, Hulshof, P, Zock, P & Katan, MBAnalysis of C18: 1 cis and trans fatty acid isomers by the combination of gas-liquid chromatography of 4,4- dimethyloxazoline derivatives and methyl esters. J Am Oil Chem Soc (1998) 75, 977–985.CrossRefGoogle Scholar
Aro, A, Mannisto, S, Salminen, I, Ovaskainen, ML, Kataja, V & Uusitupa, MInverse association between dietary and serum conjugated linoleic acid and risk of breast cancer in postmenopausal women. Nutr. Cancer (2000) 38, 151–157.CrossRefGoogle ScholarPubMed
Association of Official Analytical Chemists Official Method of Analysis Vol. II, 16th ed. Arlington VA: AOAC. (1995)Google Scholar
Banni, S, Angioni, E, Murru, E, Carta, G, Melis, MP, Bauman, DE, Dong, Y & Ip, CVaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland. Nutr Cancer (2001) 41, 91–97.CrossRefGoogle ScholarPubMed
Bauman, DE & Griinari, JMNutritional regulation of milk fat synthesis. Annu Rev Nutr (2003) 23, 203–227.CrossRefGoogle ScholarPubMed
Belury, MADietary conjugated linoleic acid in health: physiological effects and mechanisms of action. Annu Rev Nutr (2002) 22, 505–531.CrossRefGoogle ScholarPubMed
Burdge, GC, Derrick, PR, Russell, JJ, Tricon, S, Kew, S, Banerjee, T, Grimble, RF, Williams, CM, Yaqoob, P & Calder, PCIncorporation of cis-9, trans-11 or trans-10, cis-12 conjugated linoleic acid into human erythrocytes in vivo. Nutr Res (2005) 25, 13–19.CrossRefGoogle Scholar
Cohen, P & Friedman, JMLeptin and the control of metabolism: role for stearoyl-CoA desaturase-1 (SCD-1). J Nutr (2004) 134, 2455S–2463S.CrossRefGoogle ScholarPubMed
Corl, BA, Barbano, DM, Bauman, DE & Ip, Ccis-9 trans-11 CLA derived endogenously from trans-11-18: 1 reduces cancer risk in rats. J Nutr (2003) 133, 2893–2900.CrossRefGoogle ScholarPubMed
Corl, BA, Baumgard, LH, Dwyer, DA, Griinari, JM, Phillips, BS & Bauman, DEThe role of D9-desaturase in the production of cis-9 trans-11 CLA. J Nutr Biochem (2001) 12, 622–630.CrossRefGoogle Scholar
European Food Safety Authority The Opinion of the Scientific Panel on dietetic Products, Nutrition and Allergies on a request from the Commission related to the presence of trans-fatty acids in foods and the effect on human health of the consumption of trans-fatty acids. EFSA J (2004) 81, 1–49.Google Scholar
Folch, J, Lees, M & Stanley, GHSAsimple method for isolation and purification of total lipids from animal tissues. J Biol Chem (1957) 226, 497–509.CrossRefGoogle Scholar
Fremann, D, Linseisen, J & Wolfram, GDietary conjugated linoleic acid (CLA) intake assessment and possible biomarkers of CLA intake in young women. Public Health Nutr (2002) 5, 73–80.CrossRefGoogle ScholarPubMed
Fritsche, J & Steinhart, HAmounts of conjugated linoleic (CLA) in German foods and evaluation of daily intake. Z Lebensm Unters Forsch A (1998) 2065, 77–82.CrossRefGoogle Scholar
Galluzzi, JR, Cupples, LA, Otvos, JD, Wilson, PW, Schaefer, EJ & Ordovas, JMAssociation of the A/T54 polymorphism in the intestinal fatty acid binding protein with variations in plasma lipids in the Framingham Offspring Study. Atherosclerosis (2001) 159, 417–424.CrossRefGoogle ScholarPubMed
Gläser, KR, Scheeder, MRL & Wenk, CDietary C18:1 trans fatty acids increase conjugated linoleic acid in adipose tissue of pigs. Eur J Lipid Sci Technol (2000) 102, 684–686.3.0.CO;2-R>CrossRefGoogle Scholar
Griinari, JM & Bauman, DEBiosynthesis of conjugated linoleic acid and its incorporation into meat and milk in ruminants In Advances in Conjugated Linoleic Acid Research, [MP, Yurawecz, MM, Mossoba, JKG, Kramer, MW, Pariza, and GJ, Nelson, editors]. Champaign IL: AOCS Press pp. vol. 1, 180–200 (1999)Google Scholar
Griinari, JM, Corl, BA, Lacy, SH,Chouinard, PY, Nurmela, KVV & Bauman, DEConjugated linoleic acid is synthesized endogenously in lactating dairy cows by D9-desaturase. J Nutr (2000) 130, 2285–2291.CrossRefGoogle Scholar
Halsall, DJ, Martensz, ND, Luan, J, Maison, P, Wareham, NJ, Hales, CN & Byrne, CDA common apolipoprotein B signal peptide polymorphism modifies the relation between plasma non-esterified fatty acids and triglyceride concentration in men. Atherosclerosis (2000) 152, 9–17.CrossRefGoogle ScholarPubMed
Holman, RT & Mahfouz, MMCis and trans-octadecenoic acids as precursors of polyunsaturated acids. Prog Lip Res (1981) 20, 151–156.CrossRefGoogle ScholarPubMed
Ip, C, Banni, S, Angioni, E, Carta, G, McGinley, J, Thompson, HJ, Barbano, D & Bauman, DConjugated linoleic acid-enriched butter fat alters mammary gland morphogenesis and reduces cancer risk in rats. J Nutr (1999) 129, 2135–2142.CrossRefGoogle ScholarPubMed
Jahreis, G, Fritsche, J & Steinhart, HConjugated linoleic acid in milk fat: high variation depending on production system. Nutr Res (1997) 17, 1479–1484.CrossRefGoogle Scholar
Jahreis, G & Kraft, JSources of conjugated linoleic acid in the human diet. Lipid Tech (2002) 14, 29–32.Google Scholar
Jones, BA, Maher, MA, Banz, WJ, Zemel, MB, Whelan, J, Smith, PJ & Moustaïd, NAdipose tissue stearoyl-CoA desaturase mRNA is increased by obesity and decreased by polyunsaturated fatty acids. Am J Physiol (1996) 271, E44–E49.Google ScholarPubMed
Kepler, CR, Hirons, KP, McNeill, JJ & Tove, SBIntermediates and products of the biohydrogenation of linoleic acid by Butyrivibrio fibrisolvens. J Biol Chem (1966) 241, 1350–1354.CrossRefGoogle Scholar
Kohlmeier, LFuture of dietary exposure assessment. Am J Clin Nutr (1995) 61, 702S–709S.CrossRefGoogle ScholarPubMed
Kraft, J Incorporation of conjugated linoleic acids into body lipids with special regard to the isomeric distribution PhD Thesis Jena, Friedrich Schiller University, (2004)Google Scholar
Kraft, J, Collomb, M, Möckel, P, Sieber, R & Jahreis, GDifferences in CLA isomer distribution of cow's milk lipids. Lipids (2003) 38, 657–664.CrossRefGoogle ScholarPubMed
Lee, KN, Pariza, MW & Ntambi, JMDifferential expression of hepatic stearoyl-CoA desaturase gene 1 in male and female mice. Biochem Biophys Acta (1996) 1304, 85–88.CrossRefGoogle ScholarPubMed
Lee, KW, Lee, HJ, Cho, HY & Kim, YJRole of the conjugated linoleic acid in the prevention of cancer. Crit Rev Food Sci Technol (2005) 45, 135–144.CrossRefGoogle ScholarPubMed
Legrand, P & Hermier, DHepatic delta 9 desaturation and plasma VLDL level in genetically lean and fat chickens. Int J Obes (1992) 16, 289–294.Google ScholarPubMed
Lippel, KActivation of long-chain fatty-acids by subcellularfractions of rat-liver. 1. Activation of trans-unsaturated acids.Lipids (1973) 8, 111–118.CrossRefGoogle ScholarPubMed
Lock, AL, Corl, BA, Barbano, DM, Bauman, DE & Ip, CThe anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by D9-desaturase in rats. J Nutr (2004) 134, 2698–2704.CrossRefGoogle Scholar
Lock, AL, Parodi, PW & Bauman, DEThe biology of trans fatty acids: implications for human health and the dairy industry. Austr J Dairy Tech (2005) 60, 134–142.Google Scholar
Loeffler, GBasiswissen Biochemie mit Pathobiochemie, 6th ed. BerlinSpringer-Verlag (2005)Google Scholar
Loor, JJ, Lin, X & Herbein, JHDietary trans-vaccenic acid (trans-11–18:1) increases concentration of cis9, trans11-conjugated linoleic acid (rumenic acid) in tissues of lactating mice and suckling pups. Reprod Nutr Dev (2002) 42, 85–99.CrossRefGoogle Scholar
Mahfouz, MM, Valicenti, AJ & Holman, RTDesaturation of isomeric trans-octadecenoic acids by rat liver microsomes. Biochim Biophys Acta (1980) 618, 1–12.CrossRefGoogle ScholarPubMed
Miller, CW, Waters, KM & Ntambi, JMRegulation of hepatic stearoyl-CoA desaturase gene by Vitamin A. Biochem Biophys Res Commun (1997) 231, 206–210.CrossRefGoogle ScholarPubMed
Mittendorfer, BSexual dimorphism in human lipid metabolism. J Nutr (2005) 135, 681–686.CrossRefGoogle ScholarPubMed
Miyazaki, M, Jacobson, MJ, Man, WC, Cohen, P, Asilmaz, E, Freidman, JM & Ntambi, JMIdentification and characterization of murine SCD4: a novel heart-specific stearoyl-CoA desaturase isoform regulated by leptin and dietary factors. J Biol Chem (2003) 278, 33904–33911.CrossRefGoogle ScholarPubMed
Molkentin, J & Precht, DDetermination of trans-octadecenoic acids in German margarines, shortening, cooking and dietary fats by Ag-TLC/GC Z. Ernährungswiss (1995) 34, 314–317.CrossRefGoogle Scholar
Noble, RC, Moore, JH & Harfoot, CGObservations on the pattern on biohydrogenation of esterified and unesterified linoleic acid in the rumen. Br J Nutr (1974) 31, 99–108.CrossRefGoogle ScholarPubMed
Ntambi, JMDietary regulation of stearoyl-CoA desaturase 1 gene expression in mouse liver. J Biol Chem (1992) 267, 10925–10930.CrossRefGoogle ScholarPubMed
Ntambi, JMRegulation of stearoyl-CoA desaturase by polyunsaturated fatty acids and cholesterol. J Lipid Res (1999) 40, 1549–1558.CrossRefGoogle Scholar
Ntambi, JMRegulation of stearoyl-CoA desaturase expression. Lipids (2004) 39, 1061–1065.CrossRefGoogle ScholarPubMed
Pala, V, Krogh, V, Muti, P, Chajès, V, Riboli, E, Micheli, A, Saadatian, M, Sieri, S & Berrino, FErythrocyte membrane fatty acids and subsequent breast cancer: a prospective Italian study. J Natl Cancer Inst (2001) 93, 1088–1095.CrossRefGoogle ScholarPubMed
Parodi, PWMilk fat in human nutrition. Austr J Dairy Techn (2004) 59, 3–59.Google Scholar
Piperova, LS, Sampugna, J, Teter, BB, Kalscheur, KF, Yurawecz, MP, Ku, Y, Morehouse, KM & Erdman, RADoudenal and milk trans octadecenoic acid and conjugated linoleic acid (CLA) isomers indicate that postabsorptive synthesis is the predominant source of cis-9-containing CLA in lactating dairy cows. J Nutr (2002) 132, 1235–1241.CrossRefGoogle Scholar
Pollard, M, Gunstone, FD, James, AT & Morris, LJDesaturation of postional and geometric isomers of monoenoic fatty acids by microsomal preparations from rat liver. Lipids (1980) 15, 306–314.CrossRefGoogle Scholar
Precht, D, Molkentin, J, Destaillats, F & Wolff, RLComparative studies on individual isomeric 18:1 acids in cow, goat, and ewe milk fats by low-temperature high-resolution capillary gas-liquid chromatography. Lipids (2001) 36, 827–832.CrossRefGoogle Scholar
Salminen, I, Mutanen, M & Aro, ADietary trans fatty acids increase conjugated linoleic acid levels in human serum. J Nutr Biochem (1998) 9, 93–98.CrossRefGoogle Scholar
Santora, JE, Palmquist, DL & Roehrig, KLTrans-vaccenic acid is desaturated to conjugated linoleic acid in mice. J Nutr (2000) 130, 208–215.CrossRefGoogle ScholarPubMed
Sergiel, JP, Chardigny, JM, Sebedio, JL, Berdeaux, O, Juaneda, P, Loreau, O, Pasquis, B & Noel, JPb-oxidation of conjugated linoleic acid isomers and linoleic acid in rats. Lipids (2001) 36, 1327–1329.CrossRefGoogle Scholar
Sessler, AM & Ntambi, JMPolyunsaturated fatty acid regulation of gene expression. J Nutr (1998) 128, 923–926.CrossRefGoogle ScholarPubMed
Stangl, G, Müller, H & Kirchgessner, MConjugated linoleic acid effects on circulating hormones, metabolites and lipoproteins, and its proportion in fasting serum and erythrocyte membranes of swine. Eur J Nutr (1999) 38, 271–277.CrossRefGoogle ScholarPubMed
Talmud, PJ, Palmen, J, Luan, J, Flavell, D, Byrne, CD, Waterworth, DM & Wareham, NJVariation in the promoter of the human hormone sensitive lipase gene shows gender specific effects on insulin and lipid levels: results from the Ely study. Biochim Biophys Acta (2001) 1537, 239–244.CrossRefGoogle ScholarPubMed
Tocher, DR, Leaver, MJ & Hodgson, PARecent advances in the biochemistry and molecular biology of fatty acyl desaturases. Prog Lipid Res (1998) 37, 73–117.CrossRefGoogle ScholarPubMed
Turpeinen, AM, Mutanen, MAA, Salminen, I, Basu, S, Palmquist, DL & Griinari, JMBioconversion of vaccenic acid to conjugated linoleic acid in humans. Am J Clin Nutr (2002) 76, 504–510.CrossRefGoogle ScholarPubMed
Voorrips, LE, Brants, HAM, Kardinaal, AFM, Hiddink, GJ, van den Brandt, PA & Goldbohm, RAIntake of conjugated linoleic acid, fat, and other fatty acids in relation to postmenopausal breast cancer: the Netherlands Cohort Study on Diet and Cancer. Am J Clin Nutr (2002) 76, 873–882.CrossRefGoogle ScholarPubMed
Weggemans, RM, Rudrum, M & Trautwein, EAIntake of ruminant versus industrial trans fatty acids and risk of coronary heart disease - what is the evidence?". Eur J Lipid Sci Technol (2004) 106, 390–397.CrossRefGoogle Scholar
Wolff, RLContent and distribution of trans-18:1 acids in ruminant milk and meat fats. Their importance in European diets and their effect on human milk. J Am Oil Chem Soc (1995) 72, 259–272.CrossRefGoogle Scholar
Wolff, RL, Combe, NA, Destaillats, F, Boue, C, Precht, D, Molkentin, J & Entressangles, BFollow-up of the delta4 to delta16 trans-18: 1 isomer profile and content in French proceeds foods containing partially hydrogenated vegetable oils during the period 1995–1999.. Analytical and nutritional implications. Lipids (2000) 35, 815–825.Google Scholar