Retroconversion of dietary trans-vaccenic (trans-C18:1 n-7) acid to trans-palmitoleic acid (trans-C16:1 n-7): proof of concept and quantification in both cultured rat hepatocytes and pregnant rats

Guillocheau, Étienne; Garcia, Cyrielle; Drouin, Gaëtan; Richard, Léo; Catheline, Daniel; Legrand, Philippe; Rioux, Vincent

doi:10.1016/j.jnutbio.2018.09.010

Cited by 18 publications

(11 citation statements)

References 65 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Besides, TVA may be converted to the trans-13 C20:1 thanks to an elongation step (Rioux et al, 2013). Last but not least, our research group recently gave formal evidence of the peroxisomal b-oxidation of dietary TVA yielding TPA (Guillocheau et al, 2019).…”

Section: Rumenic Acid (Rma)mentioning

confidence: 99%

Benefits of natural dietarytransfatty acids towards inflammation, obesity and type 2 diabetes: defining the n-7transfatty acid family

Guillocheau

Legrand

Rioux

2019

OCL

Self Cite

View full text Add to dashboard Cite

Natural trans fatty acids are trans fatty acids that naturally occur in ruminant-derived foods: milk (derived from cow, ewe, goat), dairy products (yoghurt, cheese) and ruminant meat (beef, lamb). Because natural trans fatty acids are part of the trans fatty acid family, they have been compared for decades to their industrial counterparts on a cardiovascular outcome’s basis. At current dietary intakes, it is now well recognized that natural trans fatty acids are neutral towards cardiovascular health. Still, the negative connotation remains. It is usually taken for granted in the scientific community that natural trans fatty acids have no known physiological function and therefore no particular nutritional interest. This prevailing view has totally hidden several studies, which pointed out unsuspected benefits of natural trans fatty acids on inflammation, type 2 diabetes and obesity. Some supplementation studies dealt with pure trans-vaccenic acid (trans-C18:1 n-7) and pure rumenic acid (cis-9, trans-11 C18:2), but remained somewhat aside as they were carried out on rodents. However, recent epidemiological data reached considerable impact, highlighting a protective effect of trans-palmitoleic acid (trans-C16:1 n-7) towards the risk of type 2 diabetes. Bearing in mind that natural trans fatty acids do not just consist of rumenic acid, this review is the opportunity to sum up scientific knowledge about each of these three fatty acids. We shall therefore, review their occurrence in foods, and their physiological impacts. An overlooked aspect of natural trans fatty acids is that they are metabolically connected. The second aim of this review is to underline these metabolic connections. In fact, combining physiological impacts and metabolic pathways unravel shared mechanisms of action of trans-palmitoleic, trans-vaccenic and rumenic acids, that might be explained by their common n-7 trans double bond.

show abstract

Section: Rumenic Acid (Rma)mentioning

confidence: 99%

Benefits of natural dietarytransfatty acids towards inflammation, obesity and type 2 diabetes: defining the n-7transfatty acid family

Guillocheau

Legrand

Rioux

2019

OCL

Self Cite

View full text Add to dashboard Cite

show abstract

“…[ 22–26 ] According to the second way, cis ‐vaccenic acid ( cis ‐11 C18:1, or C18:1 n‐7 cis , CVA) is chemically synthesized first, then a cis / trans isomerization and a cis / trans fractionation are carried out. [ 20,21,27–31 ]…”

Section: Fatty Acid Macadamia Nut Oil [%] Provinal [%]mentioning

confidence: 99%

“…Indeed, we previously succeeded in doing the same between CVA and TVA, reaching a 5/95 purity ratio. [ 29,30 ] As a result, we hypothesized that LC flash would work as well for C16:1 fatty acids. The negative outcomes following urea complexation were however more in line with our hypothesis: to our knowledge, this widespread technique has never been used for cis / trans fractionation.…”

Section: Fatty Acid Macadamia Nut Oil [%] Provinal [%]mentioning

confidence: 99%

Chemical Synthesis and Isolation of Trans‐Palmitoleic Acid (Trans‐C16:1 n‐7) Suitable for Nutritional Studies

Guillocheau

Drouin

Catheline

et al. 2020

Euro J Lipid Sci & Tech

Self Cite

View full text Add to dashboard Cite

Trans-palmitoleic acid (trans-9 C16:1, or trans-C16:1 n-7, TPA) is typically found in ruminant-derived foods (milk and meat). Of note, previous epidemiological studies associated high levels of circulating TPA with a lower risk of type 2 diabetes and metabolic syndrome in humans. At the current time, TPA intakes in humans are ensured by ruminant-derived foods. However, due to the very low commercial availability of TPA, there are no supplementation studies carried out so far. Therefore, the ability for dietary TPA to prevent type 2 diabetes and metabolic syndrome has never been experimentally assessed. Here, a method (among others) to get dozens of grams of pure TPA as ethyl ester, to perform dedicated supplementation studies, is reported. For that purpose, it starts from food sources containing high amounts of cis-palmitoleic acid (cis-9 C16:1, or cis-C16:1 n-7, CPA), dealing with fatty acids ethyl esters all along the experiment. CPA is purified with flash liquid chromatography, then submitted to a cis/trans isomerization step. Finally, TPA is separated from CPA by low-temperature crystallization in methanol. The final product is fully characterized by 1 H and 13 C nuclear magnetic resonance spectrometry. It is possible to produce ≈70 g of 85%-purity TPA suitable for nutritional studies. Practical Applications: The synthesized trans-palmitoleic acid may serve for supplementation (or nutritional) studies aiming at unravelling its physiological impacts suggested by epidemiological work. Depending on the amount of synthesized trans-palmitoleic acid, one may carry out nutritional studies on rodents or even on humans.Trans-palmitoleic acid (trans-9 C16:1, or trans-C16:1 n-7, TPA) belongs to the family of natural trans fatty acids, as reviewed by

show abstract

“…The rate of PAO synthesis is regulated by both the synthesis and desaturation of palmitate. Importantly, trans-palmitoleic acid, which was previously thought to be obtained only from the diet, can be endogenously generated in the liver by the cleavage of trans-vaccenic acid (trans-C18:1 n-7) by hepatic peroxisomal β-oxidation [44], which produces palmitoleic acid. This novel hepatic retro-conversion mechanism of an abundant dietary fatty acid (trans-vaccenic acid) leads to the accumulation of PAO in multiple tissues [44].…”

Section: Lipokinesmentioning

confidence: 99%

“…Importantly, trans-palmitoleic acid, which was previously thought to be obtained only from the diet, can be endogenously generated in the liver by the cleavage of trans-vaccenic acid (trans-C18:1 n-7) by hepatic peroxisomal β-oxidation [44], which produces palmitoleic acid. This novel hepatic retro-conversion mechanism of an abundant dietary fatty acid (trans-vaccenic acid) leads to the accumulation of PAO in multiple tissues [44]. Mice deficient in adipose tissue Transcriptional repressor B cell lymphoma 6 ( Bcl6 ) have increased de novo lipogenesis and an accumulation of PAO in the TAG of serum and adipose tissue.…”

Section: Lipokinesmentioning

confidence: 99%

The Regulation of Lipokines by Environmental Factors

Hernández-Saavedra

Stanford

2019

Nutrients

View full text Add to dashboard Cite

Adipose tissue is a highly metabolically-active tissue that senses and secretes hormonal and lipid mediators that facilitate adaptations to metabolic tissues. In recent years, the role of lipokines, which are lipid species predominantly secreted from adipose tissue that act as hormonal regulators in many metabolic tissues, has been an important area of research for obesity and diabetes. Previous studies have identified that these secreted lipids, including palmitoleate, 12,13-diHOME, and fatty acid–hydroxy–fatty acids (FAHFA) species, are important regulators of metabolism. Moreover, environmental factors that directly affect the secretion of lipokines such as diet, exercise, and exposure to cold temperatures constitute attractive therapeutic strategies, but the mechanisms that regulate lipokine stimulation have not been thoroughly reviewed. In this study, we will discuss the chemical characteristics of lipokines that position them as attractive targets for chronic disease treatment and prevention and the emerging roles of lipokines as regulators of inter-tissue communication. We will define the target tissues of lipokines, and explore the ability of lipokines to prevent or delay the onset and development of chronic diseases. Comprehensive understanding of the lipokine synthesis and lipokine-driven regulation of metabolic outcomes is instrumental for developing novel preventative and therapeutic strategies that harness adipose tissue-derived lipokines.

show abstract

Retroconversion of dietary trans-vaccenic (trans-C18:1 n-7) acid to trans-palmitoleic acid (trans-C16:1 n-7): proof of concept and quantification in both cultured rat hepatocytes and pregnant rats

Cited by 18 publications

References 65 publications

Benefits of natural dietarytransfatty acids towards inflammation, obesity and type 2 diabetes: defining the n-7transfatty acid family

Benefits of natural dietarytransfatty acids towards inflammation, obesity and type 2 diabetes: defining the n-7transfatty acid family

Chemical Synthesis and Isolation of Trans‐Palmitoleic Acid (Trans‐C16:1 n‐7) Suitable for Nutritional Studies

The Regulation of Lipokines by Environmental Factors

Contact Info

Product

Resources

About