Cited by 495Fatty Acid Research and HealthEdible Oils Quality and AnalysisLipid metabolism and biosynthesis

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Bioconversion of vaccenic acid to conjugated linoleic acid in humans

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Turpeinen, Anu M, Mutanen, Marja, Aro, Antti, Salminen, Irma, Basu, Samar, Palmquist, Donald L, Griinari, J Mikko·2002·The American Journal of Clinical Nutrition

DOI 10.1093/ajcn/76.3.504

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Abstract

Background Vaccenic acid (11-trans octadecenoic acid; VA), a major trans fatty acid in the fat of ruminants, is produced in the rumen and converted in tissues to rumenic acid (9-cis, 11-trans octadecenoic acid; RA), an isomer of conjugated linoleic acid, by Delta(9)-desaturase. There are indications that this conversion also occurs in humans.Objective The aim of this controlled intervention was to study the conversion of VA to RA in humans after consumption of diets with increasing amounts of VA.Design Thirty healthy subjects consumed a baseline diet rich in oleic acid for 2 wk. The subjects were then divided into 3 groups (n = 10 per group) and provided a diet containing 1.5, 3.0, or 4.5 g VA/d for 9 d. All diets contained equal amounts of macronutrients and differed only in their fatty acid compositions. The fats were mixed into conventional foods, and nearly all food was provided during the study.Results The proportion of VA in serum total fatty acids increased 94%, 307%, and 620% above baseline with the 1.5-, 3.0-, and 4.5-g diets, respectively. This was associated with a linear increase in the proportion of RA. The conversion rate was 19% on average, with significant interindividual differences with all 3 intakes of VA. The urinary excretion of 8-iso-prostaglandin F(2alpha) increased in all groups (P < 0.001).Conclusions The results quantify the desaturation of VA to RA in humans. Conversion is likely to contribute significantly to the amount of RA available to the body, and dietary intakes of VA should thus be taken into account when predicting RA status.

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Background
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BackgroundInfluential
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“In addition, vaccenic acid (18:2, trans-11), a trans-fatty acid, also elevated urinary F2-isoprostanes (266) through metabolic conversion to conjugated linoleic acid (CLA).”
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“Vaccenic acid (C18:1 trans-11; VA) also has potential health benefits because VA can be converted to C18:2 c-9, t-11 in human (Turpeinen et al., 2002) and animal (Corl et al.”
Background
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“The slope of linear regression varies between data sets, and it is thought to reflect the rate of conversion between trans-11 18:1 and cis-9, trans-11 CLA (i.e., Δ9desaturase activity in a situation where the supply of preformed cis-9, trans-11 CLA is relatively low; Turpeinen et al., 2002).”
Background
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Background
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“CLA9 synthesis in human tissue (Turpeinen et al., 2002), dietary VA concentration ought to be considered”
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BackgroundInfluential
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Background
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Background
Bioactivity and health effects of ruminant meat lipids. Invited Review
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Background
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Background
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Method
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“Endogenous synthesis of RA from VA has also been reported in humans (6) and other species (7,8).”
Background
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Background
Tissue Fatty Acid Profiles Can Be Used to Quantify Endogenous Rumenic Acid Synthesis in Lambs
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Background
Novel cyclooxygenase‐catalyzed bioactive prostaglandin F2α from physiology to new principles in inflammation
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Background
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Effects of winter stocker growth rate and finishing system on: III. Tissue proximate, fatty acid, vitamin, and cholesterol content1
Duckett, S. K., Neel, J. P. S., Fontenot, J. P., & Clapham, W. M. (2009) · Journal of Animal Science · doi:10.2527/jas.2009-1850 · Cited by 114
“%) reported by Turpeinen et al. (2002), then the predicted level of cis-9, trans-11 CLA due to the conversion of trans-11 vaccenic acid in the human body would effectively be 12.4 mg greater.”
BackgroundInfluential
Human health effects of conjugated linoleic acid from milk and supplements
McCaffrey, T. A., Keaveney, E. M., Wallace, J. M. W., Binns, N. M., & Livingstone, M. B. E. (2011) · Nutrition Research Reviews · doi:10.1017/s0954422411000114 · Cited by 110
“However, it is unclear whether the partial conversion of trans-vaccenic to c9,t11-CLA in human intestines, liver and adipose tissue promotes adverse or beneficial effects on lipid profile((113,117)).”
Background
Derivatization of fatty acids and its application for conjugated linoleic acid studies in ruminant meat lipids
Aldai, N., Murray, B. E., Nájera, A. I., TROY, D. J., & Osoro, K. (2005) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.2110 · Cited by 110
Factors Regulating Isoprostane Formation In Vivo
Basu, S., & Helmersson, J. (2004) · Antioxidants and Redox Signaling · doi:10.1089/ars.2005.7.221 · Cited by 110
“Vaccenic acid is converted to the conjugated linoleic acid (CLA) isomer 18:2 cis -9 , trans-11 in humans (125), and this CLA isomer is known to result in elevation of levels of 8-iso-PGF 2 (cid:1) .”
Quick changes in milk fat composition from cows after transition from fresh grass to a silage diet
Elgersma, A., Ellen, G., van der Horst, H., de Boer, H. C., Dekker, P. R., & Tamminga, S. (2004) · Animal Feed Science and Technology · doi:10.1016/j.anifeedsci.2004.08.003 · Cited by 110
“Some UFA, particularly vaccenic acid (C18:1, trans-11) (Banni et al., 2001; Turpeinen et al., 2002), omega-3 polyunsaturated fatty acids (PUFA) such as linolenic acid (C18:3) and conjugated linoleic acid (CLA), especially rumenic acid (C18:2 cis-9, trans-11) (Martin and Valeille, 2002) have shown additional positive h…”
Background
Lack of effect of dietary conjugated linoleic acids naturally incorporated into butter on the lipid profile and body composition of overweight and obese men
Desroches, S., Chouinard, P. Y., Galibois, I., Corneau, L., Delisle, J., Lamarche, B., Couture, P., & Bergeron, N. (2005) · American Journal of Clinical Nutrition · doi:10.1093/ajcn.82.2.309 · Cited by 108
“In addition, 18:1 trans-11 appears to be partly converted to cis-9, trans-11 18:2 (CLA) via the action of the -9 desaturase present in the intestinal epithelium, liver, and adipose tissue of humans (63, 64).”
Background
Microbial Production of Conjugated Linoleic Acid and Conjugated Linolenic Acid Relies on a Multienzymatic System
Salsinha, A. S., Pimentel, L. L., Fontes, A. L., Gomes, A., & Rodríguez-Alcalá, L. M. (2018) · Microbiology and Molecular Biology Reviews · doi:10.1128/mmbr.00019-18 · Cited by 109
Pros and cons of CLA consumption: an insight from clinical evidences
Benjamin, S., Prakasan, P., Sreedharan, S., Wright, A. G., & Spener, F. (2015) · Nutrition & Metabolism · doi:10.1186/1743-7075-12-4 · Cited by 110
“It is also synthesized endogenously in humans from dietary VA by the activity of Δ(9)-desaturase [4,5] (Figure 1).”
Background
Nutrition and oxidative stress: a systematic review of human studies
Vetrani, C., Costabile, G., Marino, L., & Rivellese, A. A. (2012) · International Journal of Food Sciences and Nutrition · doi:10.3109/09637486.2012.738651 · Cited by 105
“An observational study (Tomey et al. 2007) shows a positive association between TFA intake and OS (Table II), but RCTs do not confirm this connection (Turpeinen et al. 2002; Tholstrup et al. 2006; Table IV).”
Background
Effect of a High Intake of Conjugated Linoleic Acid on Lipoprotein Levels in Healthy Human Subjects
Wanders, A. J., Brouwer, I. A., Siebelink, E., & Katan, M. (2010) · PLoS ONE · doi:10.1371/journal.pone.0009000 · Cited by 105
“CLA is also formed from ingested vaccenic acid in animals and in humans [6].”
Background
The Biology of Conjugated Linoleic Acids in Ruminants
(2020) · AOCS Publishing eBooks · doi:10.1201/9781439822166-10 · Cited by 103
Enrichment of Pecorino cheese with conjugated linoleic acid by feeding dairy ewes with extruded linseed: Effect on fatty acid and triglycerides composition and on oxidative stability
Mele, M. L., Contarini, G., Cercaci, L., Serra, A., Buccioni, A., Povolo, M., Conte, G., Funaro, A., Banni, S., Lercker, G., et al. (2011) · International Dairy Journal · doi:10.1016/j.idairyj.2010.12.015 · Cited by 102
Effect of dietary replacement of sunflower oil with linseed oil on intramuscular fatty acids of lamb meat
Jerónimo, E., Alves, S. P., Prates, J. A. M., Santos‐Silva, J., & Bessa, R. J. B. (2009) · Meat Science · doi:10.1016/j.meatsci.2009.06.033 · Cited by 100
“The 18:2 cis-9, trans-11 is formed during the ruminal biohydrogenation of 18:2n 6 to stearic acid (Harfoot & Hazelwood, 1997) and by endogenous conversion of 18:1 trans-11 by D9-desaturase in tissues (Griinari et al., 2000).”
Background
Comparing Subcutaneous Adipose Tissue in Beef and Muskox with Emphasis on trans 18:1 and Conjugated Linoleic Acids
Dugan, M. E. R., Kramer, J. K. G., Robertson, W. M., Meadus, W. J., Aldai, N., & Rolland, D. C. (2007) · Lipids · doi:10.1007/s11745-007-3051-7 · Cited by 100
“In addition, vaccenic acid (11t-18:1), the major trans-18:1 isomer generally present in ruminant fats is equally effective in cancer prevention [9], because of its endogenous conversion to 9c,11t-18:2 in animals [10], humans [11], and human cell lines [12].”
Background
Trans-11–18: 1 is effectively δ9-desaturated compared withTrans-12–18: 1 in humans
Kuhnt, K., Kraft, J., Moeckel, P., & Jahreis, G. (2006) · British Journal Of Nutrition · doi:10.1079/bjn20051680 · Cited by 97
“In other studies, Salminen et al. (1998) did not analyse any individual trans-18 : 1 isomers, and Turpeinen et al. (2002) gave no detailed information on serum t12 and c9,t12-18 : 2 levels.”
BackgroundMethodResultInfluential
Conjugated Linoleic Acid in Food
Parodi, P. W. (2020) · AOCS Publishing eBooks · doi:10.4324/9780429270703-8 · Cited by 96
Influence of organic diet on the amount of conjugated linoleic acids in breast milk of lactating women in the Netherlands
Rist, L., Mueller, A., Barthel, C., Snijders, B. E. P., Jansen, M. C. J. F., Simões‐Wüst, A. P., Huber, M., Kummeling, I., von Mandach, U., Steinhart, H., et al. (2007) · British Journal Of Nutrition · doi:10.1017/s0007114507433074 · Cited by 95
“In man, it can be converted by D9 desaturation to rumenic acid (Turpeinen et al. 2002), being probably responsible for one-quarter of the human CLA pool (Kuhnt et al.”
Background
Conjugated Linoleic Acid: Biosynthesis and Nutritional Significance
Bauman, D. E., & Lock, A. L. (2007) · Springer eBooks · doi:10.1007/0-387-28813-9_3 · Cited by 95
Conjugated linoleic acids: all the same or to everyone its own function?
Martin, J., & Valeille, K. (2002) · annales de biologie animale biochimie biophysique · doi:10.1051/rnd:2002042 · Cited by 94
Effect of level and duration of dietary n-3 polyunsaturated fatty acid supplementation on the transcriptional regulation of Δ9-desaturase in muscle of beef cattle1
Waters, S. M., Kelly, J., O’Boyle, P., MOLONEY, A. P., & Kenny, D. A. (2008) · Journal of Animal Science · doi:10.2527/jas.2008-1005 · Cited by 94
Gas–liquid chromatographic method for analysing complex mixtures of fatty acids including conjugated linoleic acids (cis9trans11 and trans10cis12 isomers) and long-chain (n-3 or n-6) polyunsaturated fatty acids
Aldai, N., Osoro, K., Barrón, L. J. R., & Nájera, A. I. (2006) · Journal of Chromatography A · doi:10.1016/j.chroma.2006.01.049 · Cited by 93
Milk and Cheese from Cows Fed Calcium Salts of Palm and Fish Oil Alone or in Combination with Soybean Products
Allred, S., Dhiman, T. R., Brennand, C., Khanal, R. C., McMahon, D. J., & Luchini, N. D. (2006) · Journal of Dairy Science · doi:10.3168/jds.s0022-0302(06)72088-4 · Cited by 91
“(Turpeinen et al., 2002) and animal (Corl et al.”
Intake of ruminant versus industrial trans fatty acids and risk of coronary heart disease – what is the evidence?
Weggemans, R. M., Rudrum, M., & Trautwein, E. A. (2004) · European Journal of Lipid Science and Technology · doi:10.1002/ejlt.200300932 · Cited by 90
Vaccenic acid favourably alters immune function in obese JCR:LA-cp rats
Blewett, H., Gerdung, C. A., Ruth, M. R., Proctor, S. D., & Field, C. J. (2009) · British Journal Of Nutrition · doi:10.1017/s0007114509231722 · Cited by 89
“Interest in VA has increased based on its ability to be converted to the cis-9, trans-11 form of CLA, including in humans((10)).”
Background
Enhancing the fatty acid profile of milk through forage‐based rations, with nutrition modeling of diet outcomes
Benbrook, C., Davis, D. R., Heins, B., Latif, M. A., Leifert, C., Peterman, L., Butler, G., Færgeman, O., Abel-Caines, S. F., & Barański, M. (2018) · Food Science & Nutrition · doi:10.1002/fsn3.610 · Cited by 88
“Humans are also able to convert some VA in milk to this form of CLA (Lock & Bauman, 2004; Turpeinen et al., 2002; Tyburczy et al., 2008).”
Background
Diets enriched in trans-11 vaccenic acid alleviate ectopic lipid accumulation in a rat model of NAFLD and metabolic syndrome
Jácome-Sosa, M., Borthwick, F., Mangat, R., Uwiera, R. R. E., Reaney, M. J. T., Shen, J., Quiroga, A. D., Jacobs, R. L., Lehner, R. S., & Proctor, S. D. (2014) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2014.02.011 · Cited by 87
“Thus, VA can be endogenously converted to CLA with purported health benefits in animal models and humans [4,5].”
Correlation of trans fatty acids with the severity of coronary artery disease lesions
Ahmed, S. H., Kharroubi, W., Kaoubaa, N., Zarrouk, A., Batbout, F., Gamra, H., Najjar, M. F., Lizard, G., Hininger‐Favier, I., & Hammami, M. (2018) · Lipids in Health and Disease · doi:10.1186/s12944-018-0699-3 · Cited by 82
“In humans, vaccenic acid is a precursor of the conjugated linoleic acid (CLA) C18:2, cis 9, trans 11 [45].”
Effects of feeding flaxseed or sunflower-seed in high-forage diets on beef production, quality and fatty acid composition
Mapiye, C., Aalhus, J. L., Turner, T. D., Rolland, D. C., Basarab, J. A., Baron, V. S., McAllister, T. A., Block, H. C., Uttaro, B., López-Campos, Ó., et al. (2013) · Meat Science · doi:10.1016/j.meatsci.2013.03.033 · Cited by 82
Health Implications of Beef Intramuscular Fat Consumption
TROY, D. J., Tiwari, B. K., & Joo, S.-T. (2016) · Korean Journal for Food Science of Animal Resources · doi:10.5851/kosfa.2016.36.5.577 · Cited by 80
“Similarly, some fatty acids trans-11 vaccenic acid (C18:1 trans-11) and their isomers i.e., cis-9, trans-11 of conjugated linoleic acid (CLA cis-9, trans-11) found in beef at varying level are known to have anti-carcinogenic and anti-atherogenic effects (Tricon et al., 2005; Turpeinen et al., 2002).”
Background
Intake of butter naturally enriched with cis9,trans11 conjugated linoleic acid reduces systemic inflammatory mediators in healthy young adults
Penedo, L. A., Nunes, J. C., da Gama, M. A. S., Leite, P. E. C., Quírico‐Santos, T., & Torres, A. G. (2013) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2013.08.006 · Cited by 79
Conjugated linoleic acid in adipose tissue and risk of myocardial infarction
Smit, L. A., Baylín, A., & Campos, H. (2010) · American Journal of Clinical Nutrition · doi:10.3945/ajcn.2010.29524 · Cited by 79
“For example, trans-vaccenic acid can be converted to CLA in humans (36).”
Background
Trans10,cis12–18:2 Is a More Potent Inhibitor of De Novo Fatty Acid Synthesis and Desaturation than cis9,trans11–18:2 in the Mammary Gland of Lactating Mice
Lin, X., Loor, J. J., & Herbein, J. H. (2004) · Journal of Nutrition · doi:10.1093/jn/134.6.1362 · Cited by 78
Development of conjugated linoleic acid (CLA)-mediated lipoatrophic syndrome in the mouse
Poirier, H., Niot, I., Clément, L. C., Guerre-Millo, M., & Besnard, P. (2004) · Biochimie · doi:10.1016/j.biochi.2004.11.006 · Cited by 78
Use of tannins to improve fatty acids profile of meat and milk quality in ruminants: A review
Morales, R., & Ungerfeld, E. M. (2015) · Chilean journal of agricultural research · doi:10.4067/s0718-58392015000200014 · Cited by 80
“Turpeinen et al. (2002) estimated the rate of conversion of VA to RA to be in the range from 5% to 12% in rodents and 19% to 30% in humans.”
Background
Survey of the fatty acid composition of Canadian beef: Backfat and longissimus lumborum muscle
Aldai, N., Dugan, M. E. R., Rolland, D. C., & Kramer, J. K. G. (2009) · Canadian Journal of Animal Science · doi:10.4141/cjas08126 · Cited by 76
The role of ruminant trans fat as a potential nutraceutical in the prevention of cardiovascular disease
Wang, Y., Jácome-Sosa, M., & Proctor, S. D. (2011) · Food Research International · doi:10.1016/j.foodres.2011.08.019 · Cited by 73
“In humans, the conversion of VA to c9,t11CLA has been estimated to range from 11 to 30% (Turpeinen et al., 2002).”
Background
Characterisation of intramuscular, intermuscular and subcutaneous adipose tissues in yearling bulls of different genetic groups
Aldai, N., Nájera, A. I., Dugan, M. E. R., Celaya, R., & Osoro, K. (2007) · Meat Science · doi:10.1016/j.meatsci.2007.02.008 · Cited by 74
“trans-Monenoic acid isomers are produced by rumen microorganisms as intermediates during hydrogenation of PUFAs, and it is known that C18:1trans11 (trans-vaccenic acid) can be desaturated in humans yielding the most abundant CLA isomer found in beef (cis9, trans11-CLA) (Turpeinen et al., 2002).”
Background
Serum Fatty Acids and Breast Cancer Incidence
Rissanen, H. A., Knekt, P., Järvinen, R., Salminen, I., & Hakulinen, T. (2003) · Nutrition and Cancer · doi:10.1207/s15327914nc4502_05 · Cited by 73
“The 1% of H2SO4 provides sufficient methylation but does not cause isomerization of CLA to a significant extent (27).”
Background
Trans-11 Vaccenic Acid Reduces Hepatic Lipogenesis and Chylomicron Secretion in JCR:LA-cp Rats
Wang, Y., Jácome-Sosa, M., Ruth, M. R., Goruk, S. D., Reaney, M. J. T., Glimm, D. R., Wright, D. C., Vine, D. F., Field, C. J., & Proctor, S. D. (2009) · Journal of Nutrition · doi:10.3945/jn.109.109488 · Cited by 72
Cis-9, Trans-11 Conjugated Linoleic Acid Is Synthesized from Vaccenic Acid in Lactating Women
Mosley, E. E., McGuire, M. K., Williams, J. E., & McGuire, M. A. (2006) · Journal of Nutrition · doi:10.1093/jn/136.9.2297 · Cited by 73
“Additionally, the desaturation of VA to cis-9, trans-11 CLA was also shown to occur in humans (10) and rodents (11,12).”
BackgroundMethodInfluential
Effect of Grape Seed Extract, Cistus ladanifer L., and Vegetable Oil Supplementation on Fatty Acid Composition of Abomasal Digesta and Intramuscular Fat of Lambs
Jerónimo, E., Alves, S. P., Dentinho, M. T., Martins, S. V., Prates, J. A. M., Vasta, V., Santos‐Silva, J., & Bessa, R. J. B. (2010) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf1021626 · Cited by 72
Production of conjugated linoleic acid enriched milk and dairy products from cows receiving grass silage supplemented with a cereal-based concentrate containing rapeseed oil
Ryhänen, E., Tallavaara, K., Griinari, J. M., Jaakkola, S., Mantere‐Alhonen, S., & Shingfield, K. J. (2004) · International Dairy Journal · doi:10.1016/j.idairyj.2004.07.003 · Cited by 72
Effects of feeding steers extruded flaxseed on its own before hay or mixed with hay on animal performance, carcass quality, and meat and hamburger fatty acid composition
Vahmani, P., Rolland, D. C., McAllister, T. A., Block, H. C., Proctor, S. D., Guan, L. L., Prieto, N., López-Campos, Ó., Aalhus, J. L., & Dugan, M. E. R. (2017) · Meat Science · doi:10.1016/j.meatsci.2017.04.008 · Cited by 71
Effect of grass vs. concentrate feeding on the fatty acid profile of different fat depots in lambs
Nuernberg, K., Nuernberg, G., Ender, K., Dannenberger, D., Schabbel, W., Grumbach, S., Zupp, W., & Steinhart, H. (2005) · European Journal of Lipid Science and Technology · doi:10.1002/ejlt.200501141 · Cited by 72

Authors: Turpeinen, A. M., Mutanen, M., Aro, A., Salminen, I., Basu, S., Palmquist, D. L., & Griinari, J. M.
Affiliations: Uppsala University (SE)
Corresponding author: Turpeinen, Anu M
ORCID: Turpeinen, Anu M
Venue: The American Journal of Clinical Nutrition
Publisher: Elsevier BV
Published: 2002-09
Volume: 76
Issue: 3
Pages: 504-510
ISSN: 0002-9165 (ISSN-L)
DOI: 10.1093/ajcn/76.3.504
OpenAlex: W1942808992
Cited by: 495
References: 49
Citations by year: 2026: 7 · 2025: 8 · 2024: 5 · 2023: 5 · 2022: 8 · 2021: 14 · 2020: 16 · 2019: 15 · 2018: 28 · 2017: 17 · 2016: 25 · 2015: 28 · 2014: 22 · 2013: 34 · 2012: 34
FWCI: 16.52
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/open-access/userlicense/1.0/ (vor, 7481 d)
Locations: American Journal of Clinical Nutrition (publishedVersion)
PubMed (publishedVersion)
STM:n Hallinnonalan avoin julkaisuarkisto (Julkari) (submittedVersion)
Topics: Health Sciences › Nursing › Nutrition and Dietetics › Fatty Acid Research and Health
Physical Sciences › Chemistry › Organic Chemistry › Edible Oils Quality and Analysis
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Lipid metabolism and biosynthesis
Keywords: vaccenic acid, conjugated linoleic acid, rumenic acid, delta-9 desaturase, biotransformation, trans fatty acids, dietary intake, serum fatty acids, ruminant fat, oleic acid
MeSH terms: Adult, Animals, Diet, Dietary Fats, Fatty Acids, Female, Humans, Kinetics, Lipids, Lipoproteins, VLDL, Male, Oleic Acids, Rumen, Stearic Acids, Triglycerides, Dinoprost, Linoleic Acid, F2-Isoprostanes

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Bioconversion of vaccenic acid to conjugated linoleic acid in humans

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