Synthesis and Biosynthesis of Alkoxylipids

Mangold, Helmut K.

doi:10.1002/anie.197904933

Cited by 53 publications

(11 citation statements)

References 209 publications

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“…Mangold stated more than 30 years ago: "Ideally, triacylglycerols should be converted directly into trialkylglycerols" [9]. At that time the reduction of tristearin and trimyristin with LiAlH 4 in the presence of BF 3 .etherate was claimed [10].…”

Section: Introductionmentioning

confidence: 99%

Reduction of high oleic sunflower oil to glyceryl trioleyl ether

Biermann

Metzger

2013

Euro J Lipid Sci & Tech

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"High oleic" sunflower oil was converted into the respective triether using InBr 3 or GaBr 3 as catalysts and triethylsilane or 1,1,3,3-tetramethyldisiloxane (TMDS) as reducing agent in solvent-free reactions. GaBr 3 /TMDS was found to be the most efficient reduction system enabling to carry out the reduction at room or moderately elevated temperature using stoichiometric amounts of TMDS and low amounts of the catalyst (0.005-0.01 eq. Ga/ester functionality). The conversion of the starting material was 100% yielding 80% of glyceryl trioleyl ether 2.

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Section: Introductionmentioning

confidence: 99%

Reduction of high oleic sunflower oil to glyceryl trioleyl ether

Biermann

Metzger

2013

Euro J Lipid Sci & Tech

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“…Ether lipids. Ether glycerolipids are ubiquitous in the animal kingdom (32)(33)(34). Although the contents of neutral ether lipids and ether phospholipids have been determined extensively in a great variety of fish (35), little is known about the occurrence of ether lipids in Acanthocephala (1,11).…”

Section: Resultsmentioning

confidence: 99%

Sterol and fatty acid composition of neutral lipids ofParatenuisentis ambiguus and its host eel

Weber¹,

Vosmann²,

Aitzetmüller³

et al. 1994

Lipids

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The sterol composition of free sterol and steryl ester fractions of the fish parasite Paratenuisentis ambiguus was determined. In addition, the fatty acid composition of various neutral lipid classes, i.e., wax esters, steryl esters, triacylglycerols and free fatty acids, as well as the composition of the 1-O-alkyl moieties of total ether glycerolipids of the parasite, were investigated. The results of these studies were compared with those obtained on the intestinal tract tissue of its host, the eel (Anguilla anguilla). Cholesterol is the major sterol in both P. ambiguus and A. anguilla. However, the sterols of P. ambiguus contain high proportions (> 20%) of other sterols, such as campesterol and various dehydrosterols. [e.g., 7-dehydrocholesterol and cholesta-5,22(E)-dienol]. The presence of these minor sterols agrees with the known biotransformations of exogenous sterols in various helminths. Considerable differences are found in the fatty acid composition of neutral lipid fractions, as well as the total lipid extract from the endoparasite as compared to the host tissue. In particular, eicosapentaenoic acid (20:5n-3), other polyunsaturated fatty acids, such as 20:4n-6, 22:5n-3 and 22:6n-3, as well as long-chain saturated fatty acids, such as 20:0, are generally enriched in the neutral lipid fractions of the parasite as compared to those of infected eel intestine.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…In animal tissues, acyl-CoA thioesters are reduced to the corresponding long-chain alcohols v/a long-chain aldehyde intermediates (21). Saturated and monounsaturated longchain alcohols are precursors of ether glycerolipids (22,23). They can also be acylated to yield wax esters or can be reoxidized to fatty acids which, in turn, can be incorporated into various ester lipids (24).…”

Section: Metabolism Of [1-14c]hexadecan-1-ol and Rac-l-o-[1-14c]hexadmentioning

confidence: 99%

Metabolism of long‐chain fatty acids, alcohols and alkylglycerols in the fish parasiteParatenuisentis ambiguus (Acanthocephala)

Filipponi

Taraschewski

Weber³

1994

Lipids

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Specific differences between the acyl composition of lipids of the helminth Paratenuisentis ambiguus and its host eel, as shown previously, prompted us to study the lipid metabolism in this intestinal fish parasite. Adults and larvae of P. ambiguus were fed various lipid precursors, e.g., fatty acids, long-chain alcohols and 1-O-alkylglycerols, which may occur as common nutrients of intestinal parasites. Incorporation of [1-14C]palmitic acid into neutral and polar lipids was found to be similar under aerobic and near-anaerobic conditions. In adult parasites maintained in culture medium supplemented with glucose, [1-14C]palmitic acid was incorporated mainly into triacylglycerols and phosphatidylcholines, whereas [1-14C]oleic acid was incorporated preferentially into triacylglycerols. In fasted adults, as well as in larvae, [1-14C]oleic acid was mainly transferred to phosphatidylcholines. Lipolytic activity was detected in adult parasites that had been incubated with radioactive trioleoylglycerol. [1-14C]Hexadecan-1-ol was oxidized in P. ambiguus at a high rate to labeled palmitic acid, which was incorporated into various lipid classes of P. ambiguus. Small but significant proportions of radioactivity from hexadecan-1-ol were incorporated into ether glycerolipids of the parasite. A more direct precursor in ether glycerolipid metabolism, i.e., rac-1-O-[1'-14C]hexadecylglycerol, was incorporated into alkyl and 1'-alkenyl moieties of choline and etha-nolamine ether-glycerophospholipids of P. ambiguus in high yield. High proportions of labeled diacylglycerols, triacylglycerols and steryl esters were detected in surface lipids as well as lipid extracts of the culture media after incubation of P. ambiguus with [1-14C]palmitic or [1-14C]oleic acids.(ABSTRACT TRUNCATED AT 250 WORDS)

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Synthesis and Biosynthesis of Alkoxylipids

Cited by 53 publications

References 209 publications

Reduction of high oleic sunflower oil to glyceryl trioleyl ether

Reduction of high oleic sunflower oil to glyceryl trioleyl ether

Sterol and fatty acid composition of neutral lipids ofParatenuisentis ambiguus and its host eel

Metabolism of long‐chain fatty acids, alcohols and alkylglycerols in the fish parasiteParatenuisentis ambiguus (Acanthocephala)

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