Cis-9, trans-11 conjugated linoleic acid is endogenously synthesized from palmitelaidic (C16:1 trans-9) acid in bovine adipocytes1

Kadegowda, Anil K. G.; Burns, T. A.; Miller, M. C.; Duckett, S. K.

doi:10.2527/jas.2012-5590

Cited by 24 publications

(19 citation statements)

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“…Almost 30 MUFAs with less than 18 atoms of carbon were also quantified, but in limited amounts (<0.10% of total FA methyl esters). Of special interest are cis ‐9 14:1 and cis ‐9 16:1, as well as trans ‐9 16:1, because of their relationship with endogenous metabolism . The inclusion of LO in the diet reduced ( P < 0.05) the contents of those cis ‐9 MUFAs in milk fat, whereas it augmented ( P < 0.05) the trans ‐9 16:1 levels.…”

Section: Resultssupporting

confidence: 54%

“…Of special interest are cis-9 14:1 and cis-9 16:1, as well as trans-9 16:1, because of their relationship with endogenous metabolism. [28][29][30] The inclusion of LO in the diet reduced (P < 0.05) the contents of those cis-9 MUFAs in milk fat, whereas it augmented (P < 0.05) the trans-9 16:1 levels. cis-9 14:1 and cis-9 16:1 rapidly increased 3-6 h after LO suppression, while their decrease was delayed for 24 h after LO supplementation (data not shown).…”

Section: Monounsaturated Fatty Acidsmentioning

confidence: 99%

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Quick changes of milk fatty acids after inclusion or suppression of linseed oil in the diet of goats

et al. 2018

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Section: Resultssupporting

confidence: 54%

Section: Monounsaturated Fatty Acidsmentioning

confidence: 99%

Quick changes of milk fatty acids after inclusion or suppression of linseed oil in the diet of goats

et al. 2018

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“…Other isomers of CLA originate from partial reduction or isomerization of dietary PUFA in the rumen [45]. There is some evidence to suggest that cis-9, trans-11 CLA may also be synthesized from the elongation and desaturation of trans-9 16:1 in ruminant tissues [51] and that trans-11 18:1 may be serve as a substrate for fatty acid desaturase-3 to yield trans-11, cis-13 CLA in mammals [148]. Supplements of plant oils and oilseeds enriched in 18:2 n-6 and 18:3 n-3 increase milk fat cis-9, trans-11 CLA concentrations ( Table 5).…”

Section: Conjugated Fatty Acidsmentioning

confidence: 99%

Manipulation of milk fatty acid composition in lactating cows: Opportunities and challenges

Kliem

Shingfield

2016

Euro J Lipid Sci & Tech

106

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Public health policies recommend a population wide decrease in the consumption of saturated fatty acids (SFA) to lower the incidence of cardiovascular and metabolic diseases. In most developed countries, milk and dairy products are the major source of SFA in the human diet. Altering milk fat composition offers the opportunity to lower the consumption of SFA without requiring a change in eating habits. Supplementing the diet of lactating cows with oilseeds, plant oils and marine lipids can be used to replace the SFA in milk fat with monounsaturated fatty acids (MUFA), and to a lesser extent, polyunsaturated fatty acids (PUFA). Due to ruminal metabolism, the decreases in milk SFA are also accompanied by increases in trans fatty acids (TFA), including conjugated isomers. The potential to lower SFA, enrich cis MUFA and PUFA, and alter the abundance and distribution of individual TFA in milk differs according to oil source, form of lipid supplement and degree of oilseed processing, and the influence of other components in the diet. The present review summarises recent evidence on changes in milk fat composition that can be achieved using dietary lipid supplements and highlights the challenges to commercial production of modified milk and dairy products. A meta‐analysis on the effects of oilseeds on milk fatty acid composition is also presented. Practical applications: Milk and dairy products are the major source of SFA in the diet in most developed countries. Including oilseeds, plant oils, and to a lesser extent, marine lipids in the diet of lactating cows can replace SFA with MUFA and PUFA in milk offering a mechanism to lower SFA consumption in human populations. Understanding the sources of variation in milk fat composition responses, and adjusting other ingredients in the diet to accommodate lipid supplements offers the opportunity to consistently produce milk with an altered fatty acid composition. However, commercialisation of dedicated supply chains will depend on whether the added costs of production and segregation of modified milk for processing can be recovered at retail. Dairy products are the major source of saturated fatty acids in diets of developed countries. There are various dietary strategies that can be employed at the dairy cow level to alter milk fat fatty acid composition, but it is important to understand variations in cow response to these interventions to consistently produce milk with altered fatty acid composition.

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“…Its application for the formulations in the fluorescent detection of amidinium-carboxylate and amidinium formation has also been reported [13] Palmitelaidic (C16:1 trans -9) acid has been reported to have beneficial health effects. Circulating palmitelaidic acid in adult human leads to decreased adiposity, decreased triacylglycerol, decreased insulin resistance, greater high-density lipoprotein (HDL) cholesterol concentrations and reduced incidence of diabetes [14]. 9,10-dibromohexadecanoic acid is used in organic synthetic chemistry reactions as related to fatty acid biohydrogenation [15].…”

Section: Discussionmentioning

confidence: 99%

In vitro synthesis of 9,10-dihydroxyhexadecanoic acid using recombinant Escherichia coli

2017

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BackgroundHydroxy fatty acids are widely used in food, chemical and cosmetic industries. A variety of dihydroxy fatty acids have been synthesized so far; however, no studies have been done on the synthesis of 9,10-dihydroxyhexadecanoic acid. In the present study recombinant E. coli has been used for the heterologous expression of fatty acid hydroxylating enzymes and the whole cell lysate of the induced culture was used for in vitro production of 9,10-dihydroxyhexadecanoic acid.ResultsA first of its kind proof of principle has been successfully demonstrated for the production of 9,10-dihydroxyhexadecanoic acid using three different enzymes viz. fatty acid desaturase (FAD) from Saccharomyces cerevisiae, epoxide hydrolase (EH) from Caenorhabditis elegance and epoxygenase (EPOX) from Stokasia laevis. The genes for these proteins were codon-optimised, synthesised and cloned in pET 28a (+) vector. The culture conditions for induction of these three proteins in E. coli were optimised in shake flask. The induced cell lysates were used both singly and in combination along with the trans-supply of hexadecanoic acid and 9-hexadecenoic acid, followed by product profiling by GC–MS. Formation of 9,10-dihydroxyhexadecanoic acid was successfully achieved when combination of induced cell lysates of recombinant E. coli containing FAD, EH, and EPOX were incubated with 9-hexadecenoic acid.ConclusionsThe in vitro production of 9,10-dihydroxyhexadecanoic acid synthesis using three fatty acid modification genes from different sources has been successfully demonstrated. The strategy adopted can be used for the production of similar compounds.Electronic supplementary materialThe online version of this article (doi:10.1186/s12934-017-0696-7) contains supplementary material, which is available to authorized users.

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Cis-9, trans-11 conjugated linoleic acid is endogenously synthesized from palmitelaidic (C16:1 trans-9) acid in bovine adipocytes1

Cited by 24 publications

References 56 publications

Quick changes of milk fatty acids after inclusion or suppression of linseed oil in the diet of goats

Quick changes of milk fatty acids after inclusion or suppression of linseed oil in the diet of goats

Manipulation of milk fatty acid composition in lactating cows: Opportunities and challenges

In vitro synthesis of 9,10-dihydroxyhexadecanoic acid using recombinant Escherichia coli

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