Properties and biotechnological methods to produce lipids containing conjugated linoleic acid

Adamczak, Marek; Bornscheuer, Uwe T.; Bednarski, W.

doi:10.1002/ejlt.200800020

Cited by 48 publications

(41 citation statements)

References 144 publications

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“…Due to its potential health effects, enrichment of food with CLA (Griinari & Bauman 1999;Nurmela & Griinari 1999;Mir et al 2004;Hennessy et al 2007; Adamczak et al 2008) and the design of new health products based on CLA are of increasing interest. In food technology, one of the major concerns is the autoxidation of lipids (Simic 1981).…”

Section: T H E R E F O R E K N O W L E D G E O F C L a O X I D A T mentioning

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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Section: T H E R E F O R E K N O W L E D G E O F C L a O X I D A T mentioning

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 influence of the processing conditions for producing of CLA in vitro using microorganisms has been largely studied (24,(58)(59)(60). The concentration of linoleic acid, pH, temperature and the microbial growth stage are the most important factors on the bioproduction yield of CLA (24).…”

Section: Fermentationmentioning

confidence: 99%

Conjugated Linoleic Acid in Milk and Fermented Milks: Variation and Effects of the Technological Processes

Gutiérrez

2016

Vitae

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Background: Conjugated linoleic acid (CLA) is a generic term used to describe a group of geometric and positional isomers of linoleic acid with a conjugated double bond system. CLA-isomers have been widely studied because of their important biological activity and their protective effects against several diseases, such as obesity, atherosclerosis, chronic inflammatory diseases, and cancer. Consequently, these biomolecules have attracted much attention from the dairy industry, since they are naturally found in ruminants' milk, and because the development of CLA-enriched dairy foods can be a good economic opportunity given the growth of the functional foods market, in which the dairy industry plays an important role. Objectives: This work presents a comprehensive review of the following aspects: (i) The synthesis and concentration of the CLA-isomers in milk, and the main strategies employed to increase their content in a natural manner; (ii) The influence of the main technological treatments applied to milk on the concentration of CLA-isomers; and (iii) The effects of milk fermentation on the content of CLA-isomers, and the challenges of this technological process, which has been though as a promissory alternative to naturally increase the content of CLA in fermented dairy products. Methods: Information available in various databases was reviewed. A total of 103 articles were selected on the basis of their relevance and scientific-technical quality. Results: The CLA concentration in cows' milk normally ranges between 2 and 37 mg/g fat, and is mainly affected by the dietary regime offered to the animals. From the total CLA-isomers, rumenic acid represents between 75 and 90%. The technological processes normally applied to milk (thermal processing, high pressure processing, and fermentation) might cause slight changes on the CLA concentration, but the mechanisms causing these changes have not been still established. The increase in CLA concentration by milk fermentation is strain-dependent, because of the different linoleate isomerase activity of the species. . Conclusions: Although several studies have reported increases in the concentration of CLA in milk and fermented milks in a natural manner, they are fairly moderate, and the obtained levels of CLA are significantly lower than those recommended to achieve therapeutic effects.

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“…Neben anderen Enzymen war hier vor allem eine Lipase aus Geotrichum candidum geeignet, um dieses Isomer von anderen abzutrennen, die bei der chemischen Isomerisierung von Linolsäure entstehen. [184] Lipasen wurden auch im industriellen Maßstab genutzt, um einfache Ester, beispielsweise für Anwendungen in der Kosmetik, herzustellen (Schema 22). Bekannte Beispiele sind Myristylmyristat (44) und Cetylricinoleat (45).…”

Section: Anwendung Von Lipasenunclassified

Fette und Öle als nachwachsende Rohstoffe in der Chemie

et al. 2011

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Pflanzliche und tierische Öle und Fette waren und sind die wichtigsten nachwachsenden Rohstoffe der chemischen Industrie. In den vergangenen zehn Jahren hat eine beträchtliche Verlagerung der oleochemischen Produktion sowohl geographisch als auch hinsichtlich des Rohstoffs stattgefunden: von Nordamerika und Westeuropa nach Südostasien bzw. von Rindertalg zu Palmöl. Es wird in den kommenden Jahren von großer Bedeutung sein, neue Ölpflanzen mit gewünschten interessanten Eigenschaften für die chemische Nutzung einzuführen und anzubauen, was auch die agrokulturelle Biodiversität erhöhen könnte. Das Problem der industriellen Nutzung von Pflanzenölen, die vorzugsweise Nahrungsmittel sind, ist mit der Entwicklung der globalen Biodieselproduktion dringlicher geworden. Im Folgenden werden die bemerkenswerten Fortschritte diskutiert, die während des letzten Jahrzehnts mit Pflanzenölen und den daraus erhaltenen oleochemischen Basischemikalien in der organischen Synthese, der Katalyse und der Biotechnologie gemacht wurden. Diese in großem Maßstab als nachwachsende Kohlenstoffquelle zur Verfügung stehenden Rohstoffe können beispielsweise über eine ω‐Funktionalisierung von Fettsäuren mit inneren Doppelbindungen, die Anwendung der Olefinmetathese oder die De‐novo‐Synthese von Fettsäuren zu wichtigen Produkten der chemischen Industrie veredelt werden.

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Properties and biotechnological methods to produce lipids containing conjugated linoleic acid

Cited by 48 publications

References 144 publications

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

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

Conjugated Linoleic Acid in Milk and Fermented Milks: Variation and Effects of the Technological Processes

Fette und Öle als nachwachsende Rohstoffe in der Chemie

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