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Bioconversion of vaccenic acid to conjugated linoleic acid in humans
Open accessAbstract
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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“Notably, CLA is distinct from octadeca-(9Z,12Z)-dienoic acid (linoleic acid, LA) by having a conjugated rather than methylene-interrupted diene.”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [6]
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“Vaccenic acid (trans-1118:1) could be desaturated into rumenic acid (CLA cis-9,trans11-18:2) by a 9-desaturase (called SCD-1) in rodent or human tissues [22, 23].”
National Cattlemen's Beef Association
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“Previously, we detected an increase in urinary 8-iso-PGF2a after dietary supplementation with vaccenic acid (trans-11-C18 : 1), a precursor of cis-9, trans-11-CLA((41)).”
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“the principal TFA in animal fats, vaccenic acid, can be desaturated to cis-9,trans-11 18:2 in the human organism (Turpeinen et al., 2002).”
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“Therefore, t11 is a suitable precursor for synthesis of c9,t11 CLA (Turpeinen et al., 2002; Kuhnt et al., 2006).”
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“oleic acid isomer trans-11 aka 18:1 D11 trans), which can be converted in mammals into small amounts of the conjugated linoleic acid (CLA) 18:2 cis-9, trans-11 [2, 5], whereas conventional feeding (i.”
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“In addition, it has been demonstrated that VA consumption can increase serum RA in humans (Turpeinen et al., 2002) and milk RA in lactating women (Mosley et al., 2006), and the literature suggests that VA has health benefits beyond those associated with being the only known precursor of RA (Field…”
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“…which is produced either by microbial isomerization of LA in the rumen (Harfoot and Hazlewood 1997), or by delta-9 desaturation of trans-vaccenic acid (t-VA), a microbial hydrogenation product of CLA, in the body of most mammals, including humans (Griinari et al. 2000; Turpeinen et al. 2002).”
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“The D-9-desaturase enzyme is responsible for the conversion of VA to CLA and this conversion reduces mammary carcinogenesis in rats((66,67)).”
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“This conversion also occurs in humans [22,25,26].”
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“Human tissues can directly convert vaccenic acid into the c9t11-CLA isomer (Adlof, Duval, & Emken, 2000; Turpeinen et al., 2002).”
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“Trans-11 vaccenic acid (VA) is the precursor to endogenous synthesis of the cis-9, trans-11 CLA isomer in rats [12,13] and humans [14], and is the predominant isomer of the total trans fatty acids found in ruminantderived fats such as dairy and meat products.”
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Philippaerts, A., Goossens, S., Jacobs, P. A., & Sels, B. F. (2011) · ChemSusChem · doi:10.1002/cssc.201100086 · Cited by 49
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“VA, a milk trans fatty acid [t18:1(n-7)], was shown to be the major precursor of CLA in ruminants (4) and to increase the serum level of c9,t11-CLA in humans (5,6).”
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“, 2011) and up to 30% of VA consumed can be converted to RA by humans (Turpeinen et al., 2002).”
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“Controlled intervention studies with human volunteers consuming VA have provided evidence that 19–24% of VA is desaturated to cis-9, trans-11 CLA (29,30).”
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“Trans-vaccenic acid can be converted to CLA through 9-desaturation and can contribute 20 to 25% of the CLA in humans (Turpeinen et al., 2002; Kuhnt et al., 2006).”
BackgroundQualitative characteristics of meat from young bulls fed different levels of crude glycerin
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“The development of feeding systems designed to produce milk that is low in medium chain saturated fatty acids and high in odd and branched chain fatty acids, C18:1, cis-9, and C18:2 cis-9, trans-11 CLA and PUFA could have long-term benefits on human health, without the need for consumers to change their dietary habits.”
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“Specifically, CLA may have antiobesity and antidiabetic properties by activating proliferator-activated receptors (PPAR) and adiponectin production, resulting in an increased FA oxidation and an increased glucose uptake [43].”
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“(43) showed that approximately 20 % of dietary VA was converted to CLA endogenously by D(9)-desaturase in human subjects, and because ruminant products contain at least twofold more VA than CLA, the effective physiological dose of CLA will be CLA intake £ 1·4((25)).”
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“However, meat fat from control lambs had higher VA concentrations, which could represent an advantage over PF lambs, considering that about 20 % of the dietary VA is desaturated to c9,t11-CLA in the human liver (Turpeinen et al. 2002).”
BackgroundTrans-vaccenate is Δ13-desaturated by FADS3 in rodents
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“Trans-vaccenic acid has been suggested to be even health promoting due to its possible conversion to CLA c9t11 in humans [41].”
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“Endogenous synthesis of cis-9, trans-11 CLA from C18:1 trans-11 has also been reported in humans [15] and other species [16,17], which further contributes to increasing the cis-9, trans-11 CLA levels in the body tissues.”
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“Intake of vaccenic acid resulted in a dose dependent increase in cis9,trans11-18:2 concentration in human serum (Turpeinen et al., 2002) or milk (Park et al.”
BackgroundBurdge, G. C., Tricon, S., Morgan, R., Kliem, K. E., Childs, C. E., Jones, E., Russell, J. J., Grimble, R. F., Williams, C. M., Yaqoob, P., et al. (2005) · British Journal Of Nutrition · doi:10.1079/bjn20051506 · Cited by 41
“Man is able to convert tVA to c9,t11 CLA (Turpeinen et al. 2002).”
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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 C18:1 and cis9, trans-11 CLA (i.e. D9-desaturase activity in a situation where the supply of preformed cis-9, trans11 CLA is relatively low; Turpeinen et al., 2002).”
BackgroundImpact of Conjugated Linoleic Acid (CLA) on Skeletal Muscle Metabolism
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“It has been suggested that CLA itself might be metabolized to structurally similar isoprostanes that cannot be distinguished from the isoprostanes used as oxidative markers [131, 132].”
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“food and from the conversion of other trans isomers of fatty acids [12].”
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Guillocheau, É., Legrand, P., & Rioux, V. (2019) · OCL · doi:10.1051/ocl/2019047 · Cited by 36
“2), a well-described step in both rodents (Santora et al., 2000; Gruffat et al., 2005; Kraft et al., 2006) and humans (Turpeinen et al., 2002; Kuhnt et al., 2006; Mosley et al., 2006).”
BackgroundEnhancing unsaturated fatty acids in ewe's milk by feeding rapeseed or linseed oil
Cieślak, A., Kowalczyk, J., Czauderna, M., Potkański, A., & Szumacher‐Strabel, M. (2010) · Czech Journal of Animal Science · doi:10.17221/1704-cjas · Cited by 36
“VA was also shown to increase the serum level of C18:2 c9 t11 CLA in humans (Salminen et al., 1998; Turpeinen et al., 2002).”
BackgroundWang, Y., & Proctor, S. D. (2013) · British Journal Of Nutrition · doi:10.1017/s0007114513001086 · Cited by 37
“VA is also the major precursor for the endogenous synthesis of cis-9, trans-11-CLA((85,86)).”
BackgroundTrans-fatty acids and cancer: the evidence reviewed
Thompson, A. K., Shaw, D. I., Minihane, A. M., & Williams, C. M. (2008) · Nutrition Research Reviews · doi:10.1017/s0954422408110964 · Cited by 36
“reported conversion rates in rodents of 5–12%((12)) and 19% in humans((13)).”
BackgroundNajbjerg, H., Afseth, N. K., Young, J. F., Bertram, H. C., Pedersen, M. E., Grimmer, S., Vogt, G., & Köhler, A. (2011) · The Analyst · doi:10.1039/c0an00916d · Cited by 36
Nutritional Quality of Beef Produced in Chile from Different Production Systems
Morales, R., Folch, C., Iraira, S., Teuber, N., & Realini, C. E. (2012) · Chilean journal of agricultural research · doi:10.4067/s0718-58392012000100013 · Cited by 35
“…c-9, t-11 synthesis as the C18:1 t-11 content of the diet increased in human subjects (Salminen et al., 1998; Turpeinen et al., 2002a), whereas, the rate of conversion of C18:1 t-11 to CLA c-9, t-11 was estimated to range from 5 to 12% in rodents to 19 to 30% in humans (Turpeinen et al., 2002b).”
BackgroundFatty acid composition and interrelationships among eight retail cuts of grass-feed beef
Pavan, E., & Duckett, S. K. (2012) · Meat Science · doi:10.1016/j.meatsci.2012.09.021 · Cited by 35
Manipulating dietary PUFA in animal feed: implications for human health
Butler, G. (2013) · Proceedings of The Nutrition Society · doi:10.1017/s0029665113003790 · Cited by 35
“There are numerous studies showing the potential benefits from CLA in in vitro or animal models, suggesting activity against cancer, hypertension, diabetes and other conditions((8,9)) and evidence that it can be synthesised in adipose tissue from VA((10)).”
Kuhnt, K., Kraft, J., Vogelsang, H., Eder, K., Kratzsch, J., & Jahreis, G. (2007) · British Journal Of Nutrition · doi:10.1017/s0007114507685183 · Cited by 35
“Trans-fatty acids (for example, trans-11- and trans-1218 : 1) as well as CLA are suspected of inducing oxidative stress (8-iso-PGF2a, an isoprostane biomarker of oxidative stress; Turpeinen et al. 2002; Risérus et al. 2002).”
BackgroundScholljegerdes, E. J., Hess, B. W., Moss, G. E., Hixon, D. L., & Rule, D. C. (2004) · Journal of Animal Science · doi:10.2527/2004.82123577x · Cited by 35
Conversion of t11t13 CLA into c9t11 CLA in Caco-2 Cells and Inhibition by Sterculic Oil
Schneider, A.-C., Beguin, P., Bourez, S., Perfield, J. W., Mignolet, É., Debier, C., Schneider, Y., & Larondelle, Y. (2012) · PLoS ONE · doi:10.1371/journal.pone.0032824 · Cited by 34
“It occurs in lactating cows [16–18] as well as in humans [19], mice [20], cultured MCF7 and SW480 cells [21], and represents the primary source of tissular c9t11 CLA.”
BackgroundDocumentation of Fatty Acid Profiles in Lamb Meat and Lamb‐Based Infant Foods
Nudda, A., McGuire, S., Battacone, G., Manca, M. G., Boe, R., & Pulina, G. (2011) · Journal of Food Science · doi:10.1111/j.1750-3841.2010.02027.x · Cited by 34
Ramírez-Retamal, J., & Morales, R. (2014) · Chilean journal of agricultural research · doi:10.4067/s0718-58392014000200015 · Cited by 33
“The rate of C18:1 trans-11 conversion to CLA cis9, trans-11 ranges from 5 to 12% in rodents to 19 to 30% in humans (Turpeinen et al., 2002).”
BackgroundOstrovský, I., Pavlíková, E., Blaško, J., Górová, R., Kubinec, R., Margetín, M., & Soják, L. (2009) · International Dairy Journal · doi:10.1016/j.idairyj.2009.03.006 · Cited by 33
Plata-Pérez, G., Ángeles-Hernández, J. C., Morales-Almaráz, E., del Razo-Rodríguez, O. E., López-González, F., Peláez-Acero, A., Campos-Montiel, R. G., Vargas‐Bello‐Pérez, E., & Vieyra-Alberto, R. (2022) · Animals · doi:10.3390/ani12131642 · Cited by 33
“Additionally, intake of VA increases serum CLA levels in humans [71]; both FA (VA and CLA) have been linked to human health with decreased chronic diseases [72], and the intake of CLA and VA has been shown to lead to a reduction in coronary heart disease, low incidence of atherosclerosis [73], decreased risk of hypert…”
BackgroundResearch progress on conjugated linoleic acid bio-conversion in Bifidobacterium
Mei, Y., Chen, H., Yang, B. K., Zhao, J., Zhang, H., & Chen, W. (2022) · International Journal of Food Microbiology · doi:10.1016/j.ijfoodmicro.2022.109593 · Cited by 35
Vargas‐Bello‐Pérez, E., Íñiguez-González, G., Fehrmann-Cartes, K., Toro-Mújica, P., & Garnsworthy, P. C. (2015) · Animal Feed Science and Technology · doi:10.1016/j.anifeedsci.2015.04.013 · Cited by 32
Benatar, J. R., & Stewart, R. (2014) · Nutrition Journal · doi:10.1186/1475-2891-13-32 · Cited by 32
“Whilst humans are able to convert vaccenic acid to conjugated linoleic acid by delta9 desaturase in the liver [39,40], bioconversion of cis to trans fatty acids has not been demonstrated.”
BackgroundEnhancing unsaturated fatty acids in ewe's milk by feeding rapeseed or linseed oil
Cieślak, A., Kowalczyk, J., Czauderna, M., Potkański, A., & Szumacher‐Strabel, M. (2010) · Czech Journal of Animal Science · doi:10.17221/874-cjas · Cited by 32
Castro, T., Cabezas, A., la Fuente, J. D., Isabel, B., Manso, T., & Jimeno, V. (2015) · animal · doi:10.1017/s1751731115002554 · Cited by 31
“Due to the ability of Δ desaturase in human tissue to transform t11-18:1 into c9,t 11-18:2 (Turpeinen et al., 2002), the increase in the t 11-18:1 content in meat implies an improvement of its lipid profile.”
BackgroundEbrahimi, M. M., Rajion, M. A., Jafari, S., Jahromi, M. F., Oskoueian, E., Sazili, A. Q., Goh, Y. M., & Ghaffari, M. H. (2018) · PLoS ONE · doi:10.1371/journal.pone.0188369 · Cited by 31
Anadón, A., Martínez-Larrañaga, M. R., Martínez, M., Arés, I., Ramos, E., Gómez‐Cortés, P., Juárez, M., & de la Fuente, M. Á. (2009) · Food and Chemical Toxicology · doi:10.1016/j.fct.2009.11.037 · Cited by 31
“It has also been confirmed that VA is converted via d9-desaturase to RA in human tissues (Adlof et al., 2000; Turpeinen et al., 2002).”
Rego, O. A., Rosa, H. J. D., Regalo, S. M., Alves, S. P., Alfaia, C. M., Prates, J. A. M., Vouzela, C., & Bessa, R. J. B. (2008) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.3289 · Cited by 31
Czauderna, M., Kowalczyk, J., Wąsowska, I., & Niedźwiedzka, K. (2003) · Journal of Animal and Feed Sciences · doi:10.22358/jafs/67717/2003 · Cited by 31
Conjugated linoleic acid and conjugated linolenic acid production by bifidobacteria.
Gorissen, L., Leroy, F., Raes, K., Vuyst, L. D., & Smet, S. D. (2011) · PubMed · doi:10.1016/j.ijfoodmicro.2012.02.012 · Cited by 30
Guillocheau, É., Legrand, P., & Rioux, V. (2019) · Biochimie · doi:10.1016/j.biochi.2019.12.004 · Cited by 33
The Conversion Efficiency of trans-11 and trans-12 18:1 by Δ9-Desaturation Differs in Rats
Kraft, J., Hanske, L., Möckel, P., Zimmermann, S., Härtl, A., Kramer, J. K. G., & Jahreis, G. (2006) · Journal of Nutrition · doi:10.1093/jn/136.5.1209 · Cited by 30
Effect of dietary starch level and its rumen degradability on lamb meat fatty acid composition
Oliveira, M. A., Alves, S. P., Santos‐Silva, J., & Bessa, R. J. B. (2016) · Meat Science · doi:10.1016/j.meatsci.2016.10.001 · Cited by 30
Kadegowda, A. K. G., Burns, T. A., Miller, M. C., & Duckett, S. K. (2013) · Journal of Animal Science · doi:10.2527/jas.2012-5590 · Cited by 30
Speculation on the Mechanisms of Action of Conjugated Linoleic Acid
Pariza, M. W., Park, Y., a, X. X., Ntambi, J. M., & Kang, K. (2020) · AOCS Publishing eBooks · doi:10.4324/9780429270703-14 · Cited by 29
trans Fatty Acid Content of Canadian Margarines Prior to Mandatory trans Fat Labelling
Ratnayake, W. M. N., Gagnon, C., Dumais, L., Lillycrop, W., Wong, L. Y., Meleta, M., & Calway, P. (2007) · Journal of the American Oil Chemists Society · doi:10.1007/s11746-007-1112-y · Cited by 29
“In contrast to other trans isomers of oleic acid, vaccenic acid is proven to be a unique trans isomer because it also occurs in ruminant fats [13] and it could be converted to cis-9, trans-11 conjugated linoleic acid isomer (CLA) in humans by the action of delta-9 desaturase [26, 27].”
BackgroundMa, E., Ingram, K. H., Milne, G. L., & Garvey, W. T. (2017) · Journal of the Endocrine Society · doi:10.1210/js.2017-00006 · Cited by 28
“Subjects were weight-stable upon entering the study and were fed an isocaloric diet with a standard macronutrient composition [14] to account for potential dietary effects on study measurements [39, 40].”
Method
Metadata
- 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)
- 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
- 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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