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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Background
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Background
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Background
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“However, generally, the major trans FA in ruminant’s meat, the vaccenic acid, is precursor of rumenic acid, a CLA isomer with potent biological properties (Turpeinen et al., 2002), being for this reason regarded as a beneficial trans FA (Lock and Bauman, 2004).”
Background
Metabolism of Conjugated Linoleic Acids
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“The anti-carcinogenic effect of VA is associated with its conversion to CLA, humans convert on average 19% of dietary VA to CLA via Δ9-desaturase (Turpeinen et al. 2002; Field et al. 2009).”
Background
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Background
Raman spectroscopy-based screening of IgM positive and negative sera for dengue virus infection
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Background
Butterfat fatty acids differentially regulate growth and differentiation in Jurkat T‐cells
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“Additionally, its significant bioconversion of dietary VA in humans by D9-desaturase [Turpeinen et al., 2002], supports the hypothesis that increased VA content in dairy, and in other ruminant products, may increase RA availability in human tissue.”
Background
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“Oleic acid reduces total cholesterol and low-density lipoprotein (LDL) [13], while TVA is desaturated to CLA in the human body at a rate of 19% [14].”
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“The most abundant naturally occurring CLA isomers are CLAc9,t11 (76 %) and CLAt10,c12 (1 %) [1, 2], and are derived from food sources containing ruminant fat [3].”
Background
Improving the Quality of Milk Fatty Acid in Dairy Cows Supplemented with Soybean Oil and DHA-Micro Algae in a Confined Production System
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“The main precursor of RA in the cows mammary gland is vaccenic acid (trans-11C18:1, VA) which showed anticarcinogenic properties itself and conversion to RA by human tissues [6] at an average rate of 20% [10].”
Background
Low Dietary c9t11‐Conjugated Linoleic Acid Intake from Dairy Fat or Supplements Reduces Inflammation in Collagen‐Induced Arthritis
Huebner, S. M., Olson, J. M., Campbell, J. P., Bishop, J. W., Crump, P. M., & Cook, M. E. (2016) · Lipids · doi:10.1007/s11745-016-4163-8 · Cited by 9
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Fatty Acids
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“desaturase (8), but the health effects of this remain”
Background
Alimentation animale et valeur nutritionnelle induite sur les produits dérivés consommés par l’homme : Les lipides sont-ils principalement concernés ?
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“L’homme est capable de transformer l’acide vaccénique en CLA [113].”
Background
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Schmid, A., Collomb, M., Bee, G., Bütikofer, U., Wechsler, D., Eberhard, P., & Sieber, R. (2008) · British Journal Of Nutrition · doi:10.1017/s000711450887359x · Cited by 7
“In humans the conversion rate is estimated to be about 19 %((23)).”
Background
Ruminal fermentation and degradation, kinetic flow of the digesta and milk fatty acid composition of cows fed chopped elephantgrass supplemented with soybean oil
Ribeiro, C. G. S., Lopes, F. C. F., Rodríguez, N. M., da Gama, M. A. S., & Morenz, M. J. F. (2018) · Semina Ciências Agrárias · doi:10.5433/1679-0359.2018v39n4p1775 · Cited by 7
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Consumption of dairy products of biodynamic origin is correlated with increased contents of rumenic and trans-vaccenic acid in the breast milk of lactating women
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“Since TVA can be converted to rumenic acid in humans (Turpeinen et al. 2002; Mosley et al. 2006), we believe that in this group, rumenic acid was probably newly synthesized from TVA, which is present in low amounts in industrially partially hydrogenated fats (Brouwer et al.”
Background
Cis-vaccenic acid induces differentiation and up-regulates gamma globin synthesis in K562, JK1 and transgenic mice erythroid progenitor stem cells
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“CLA (9-cis 11-trans octadecenoic acid) is one of a group of conjugated C18: Δ9,11 fatty acids that are known to mediate various beneficial health effects in humans (Turpeinen et al., 2002).”
Fetal and neonatal exposure totrans-fatty acids impacts on susceptibility to atherosclerosis in apo E*3 Leiden mice
Gates, L., Langley‐Evans, S. C., Kraft, J., Lock, A. L., & Salter, A. M. (2017) · British Journal Of Nutrition · doi:10.1017/s0007114517000137 · Cited by 7
“This is particularly significant as a proportion of dietary VA is converted to the conjugated linoleic acid (CLA) isomer, 18 : 2c9,t11, through the action of stearoyl CoA desaturase in the tissues of animals, including humans((17,18)).”
Background
Grazing versus indoor feeding : Effects on milking quality
Elgersma, A., Wever, A. C., & Nalescz-Tarwacka, T. (2006) · Socio-Environmental Systems Modeling · Cited by 7
Fatty Acids in Milk Fat
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Milk Lipids
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Endogenous synthesis of rumenic acid in humans and cattle
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“The role of ∆9-desaturase in conversion of VA to RA in humans was confirmed for the first time in the study by Turpeinen et al. (2002).”
Background
Feeding butter with elevated content of trans-10, cis-12 conjugated linoleic acid to lean rats does not impair glucose tolerance or muscle insulin response
Stefanson, A. L., Hopkins, L. E., AlZahal, O., Ritchie, I. R. W., MacDonald, T. L., Wright, D. C., McBride, B. W., & Dyck, D. J. (2014) · Lipids in Health and Disease · doi:10.1186/1476-511x-13-101 · Cited by 6
“CLA cannot be produced endogenously, and so the only source of CLA for humans is dietary consumption of the meat, milk and derived products of ruminant animals [11].”
Background
Trans fatty acid retention and conversion rates of fatty acids in tissues depend on dietary fat in mice
Saín, J., González, M. A., Lavandera, J. V., Scalerandi, M. V., & Bernal, C. (2015) · European Journal of Lipid Science and Technology · doi:10.1002/ejlt.201400287 · Cited by 6
Saturated and monounsaturated fatty acid status is associated with bone strength estimated by calcaneal ultrasonography in Inuit women from Nunavik (Canada): A cross-sectional study
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Dietary conjugated linoleic acid isomers change the unsaturation degree of hepatic fatty acids in neutral lipids but not in polar lipids
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“Apart from ruminant animals, the endogenous synthesis of CLA isomers has been reported in other mammalian species, such as mice [5], rats [6], pigs [7], and humans [8].”
Dietary Intake ofc9,t11-Conjugated Linoleic Acid Correlates with Its Concentration in Plasma Lipid Fractions of Men but Not Women,
Ritzenthaler, K. L., Shahin, A. M., Shultz, T. D., Dasgupta, N., McGuire, M. A., & McGuire, M. K. (2012) · Journal of Nutrition · doi:10.3945/jn.111.156794 · Cited by 6
Metabolism of Conjugated Linoleic Acids
(2020) · AOCS Publishing eBooks · doi:10.1201/9781439822166-15 · Cited by 6
Enrichment of lamb rations with carnosic acid and seleno-compounds affects the content of selected lipids and tocopherols in the pancreas
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“In fact, in mammals, a diet rich in PUFA was shown to decrease Δ9-desaturase activity, whereas carbohydrates, cholesterol and low- or free-fat diets were found to increase it (Turpeinen et al., 2002).”
Background
Infectious enteritis
清, 山., & 聡, 河. (1999) · Current Treatment Options in Gastroenterology · doi:10.1007/s11938-999-0039-9 · Cited by 5
Effects of oats grain supplements on performance, rumen parameters and composition of beef from cattle grazing oats pasture
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HACIA UNA ARGENTINA LIBRE DE GRASAS TRANS
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“Something more, a definite portion of vaccenic from the human diet is converted into rumenic acid (Turpeinen et al., 2002).”
Background
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“In addition, in human tissues, approximately 19% of the consumed trans-11 C18:1 is converted to rumenic acid (TURPEINEN et al., 2002).”
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Sheep Milk
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Ácidos grasos trans: consumo e implicaciones en la salud en niños
Fernández-Michel, S. G., Díaz, C. L. G., Guzmán, M. G. A., & Clamont, M. G. R. (2008) · LA Referencia (Red Federada de Repositorios Institucionales de Publicaciones Científicas) · Cited by 3
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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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