The biologically active isomers of conjugated linoleic acid

Pariza, Michael W.; Park, Yeonhwa; Cook, Mark E.

doi:10.1016/s0163-7827(01)00008-x

Cited by 924 publications

(689 citation statements)

References 51 publications

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“…The concentrations of total CLA at the end of the study were 20.18 mg g -1 (diet C) and 5.71 mg g -1 (diet D); for the isomers 9c, 11t and 10t, 12c, they were 12.52 and 7.66 mg g -1 (diet C) and 3.86 and 1.85 mg g -1 (diet D), respectively. The difference in the incorporation of the isomers is due to the fact that 9c, 11t is better incorporated into the lipid fractions (Yu et al, 1998), whereas 10t, 12c is related to energy metabolism (Pariza et al, 2001). The concentrations of CLA found in the muscle of Striped bass was 73.0 mg g -1 (Twibell et al, 2000); 19.0 mg g -1 in codfish fingerlings (Kennedy et al, 2007); and 35.8 mg g -1 in the muscle of pacu (Santos et al, 2009).…”

Section: Resultsmentioning

confidence: 99%

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Incorporation of conjugated linoleic acid (CLA) and α-linolenic acid (LNA) in pacu fillets

et al. 2014

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Section: Resultsmentioning

confidence: 99%

“…These compounds occur in meat and dairy products from ruminants, but they are also present at lower levels in many other foodstuffs (Chin et al, 1992;Pariza et al, 2001). …”

Section: Introductionmentioning

confidence: 99%

Incorporation of conjugated linoleic acid (CLA) and α-linolenic acid (LNA) in pacu fillets

et al. 2014

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“…Trans-10,cis-12 CLA also induces adipocyte apoptosis in mice [39][40][41][42][43] , perhaps mediated by an increase in tumour necrosis factor alpha (TNFa) 39 , but the effects of CLA on lipolysis in vivo and in vitro are conflicting 10,38 . Data regarding its effects on preadipocyte differentiation are inconclusive, possibly depending on species, CLA isomer and experimental conditions 4,37 . Chronic treatment with trans-10,cis-12 CLA significantly reduces the expression of several adipocytespecific genes, including PPARa and PPARg target genes, partly due to an increase in nuclear factor kappa B (NFkB) activity and subsequent induction of interleukin-6 44 , therefore explaining at least part of its effects on glucose and lipid metabolism.…”

Section: Effects Of Conjugated Linoleic Acid On Adipocytesmentioning

confidence: 99%

Conjugated linoleic acid (CLA) and obesity

Silveira

Carraro

Monereo

et al. 2007

Public Health Nutr.

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Background: The term conjugated linoleic acid (CLA) refers to several positional and geometric conjugated dienoic isomers of linoleic acid (LA), of which the trans-10,cis-12 isomer has been reported to reduce adiposity and increase lean mass in mice and other animals when included at #1% of the diet. However, most dietary CLA in humans is obtained from dairy products, accounting for the cis-9,trans-11 CLA isomer, also known as rumenic acid, for more than 90% of the total CLA intake. Commercial CLA preparations industrially produced, containing trans-10,cis-12 and cis-9,trans-11 CLA isomers in diverse proportions, are attracting consumers' interest because of the purported body fat-lowering effects of CLA, coupled to the perception of a 'natural' compound devoid of harmful effects. Nevertheless, despite numerous studies on CLA effects on body composition for nearly a decade, the mechanisms by which CLA isomers elicit their effects remain largely unknown. The purpose of this paper is to provide an updated review of the studies performed on animals and humans, as well as to describe the potential mechanisms involved in CLA effects on body weight and composition and metabolism. Method: Literature review. Results: Experiments in humans have not been able to show a significant effect on body weight, body composition or weight regain related to either of the CLA isomers. In fact, some studies suggest a tendency towards a decrease in body fat mass and an increase in body lean mass, while some others raise concern about the possibility of deleterious effects of trans-10,cis-12 CLA on lipid profile, glucose metabolism and insulin sensitivity. Conclusions: Evidence regarding effectiveness of CLA in humans is not concluding.

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“…Today a number of beneficial physiological properties are attributed to CLA such as anti-cancer, anti-atherosclerosis, anti-inflammatory, and anti-obesity effects (reviewed in Scimeca 1999;Gnädig et al 2001;Pariza et al 2001;Evans ME et al 2002;Belury 2002;Terpstra 2004;Wahle et al 2004;Zulet et al 2005; Kelley et al 2007;Li et al 2008). These beneficial effects seem to be structure-specific.…”

Section: Introductionmentioning

confidence: 99%

Autoxidation of Conjugated Linoleic Acid Methyl Ester in the Presence of α‐Tocopherol: The Hydroperoxide Pathway

Pajunen

Johansson

Hase

et al. 2008

Lipids

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The autoxidation of conjugated linoleic acid (CLA) is poorly understood in spite of increasing interest in the beneficial biological properties of CLA and growing consumption of CLA-rich foods. In this thesis, the autoxidation reactions of the two major CLA isomers, 9-cis,11-transoctadecadienoic acid and 10-trans,12-cis-octadecadienoic acid, are investigated. The results contribute to an understanding of the early stages of the autoxidation of CLA methyl ester, and provide for the first time a means of producing and separating intact CLA methyl ester hydroperoxides as well as basic knowledge on lipid hydroperoxides and their hydroxy derivatives.Conjugated diene allylic monohydroperoxides were discovered as primary autoxidation products formed during autoxidation of CLA methyl esters in the presence and absence oftocopherol. This established that one of the autoxidation pathways of CLA methyl ester is the hydroperoxide pathway.Hydroperoxides were produced from the two major CLA methyl esters by taking advantage of the effect of -tocopherol to promote hydroperoxide formation. The hydroperoxides were analysed and separated first as methyl hydroxyoctadecadienoates and then as intact hydroperoxides by HPLC. The isolated products were characterized by UV, GC-MS, and NMR techniques. In the presence of a high amount of -tocopherol, the autoxidation of CLA methyl ester yields six kinetically-controlled conjugated diene monohydroperoxides and is diastereoselective in favour of one particular geometric isomer as a pair of enantiomers. The primary autoxidation products produced from the two major CLA isomers include new positional isomers of conjugated diene monohydroperoxides, the 8-, 10-, 12-, and 14-hydroperoxyoctadecadienoates. Furthermore, two of these new positional isomers have an unusual structure for a cis,trans lipid hydroperoxide where the allylic methine carbon is adjacent to the cis instead of the usual trans double bond.The 1 H and 13 C NMR spectra of nine isomeric methyl hydroxyoctadecadienoates and of ten isomeric methyl hydroperoxyoctadecadienoates including the unusual cis,trans hydroperoxides, i.e. Me 8-OOH-9c,11t and Me 14-OOH-10t,12c, were fully assigned with the aid of 2D NMR spectroscopy. The assigned NMR data enabled determination of the effects of the hydroxyl and hydroperoxyl groups on the carbon chemical shifts of CLA isomers, identification of diagnostic signals, and determination of chemical shift differences of the olefinic resonances that may help with the assignment of structure to as yet unknown lipid hydroperoxides either as hydroxy derivatives or as intact hydroperoxides.A mechanism for the hydroperoxide pathway of CLA autoxidation in the presence of a high amount of -tocopherol was proposed based on the characterized primary products, their relative distribution, and theoretical calculations. This is an important step forward in CLA research, where exact mechanisms for the autoxidation of CLA have not been presented before. Knowledge of these hydroperoxide formation steps is of cr...

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The biologically active isomers of conjugated linoleic acid

Cited by 924 publications

References 51 publications

Incorporation of conjugated linoleic acid (CLA) and α-linolenic acid (LNA) in pacu fillets

Incorporation of conjugated linoleic acid (CLA) and α-linolenic acid (LNA) in pacu fillets

Conjugated linoleic acid (CLA) and obesity

Autoxidation of Conjugated Linoleic Acid Methyl Ester in the Presence of α‐Tocopherol: The Hydroperoxide Pathway

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