Diol lipids

Bergel'son, L. D.; Vaver, V. A.; Prokazova, N. V.; Ushakov, A. N.; Rozynov, B. V.; Stefanov, Kamen; Ilukhina, L.I.; Simonova, Tatyana N.

doi:10.1016/0005-2760(72)90006-9

Cited by 22 publications

(1 citation statement)

References 18 publications

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“…Our results would be the first one that diol lipid was found in the phospholipid fraction of yeast, though Bergelson and his coworkers recently reported the finding of ethyleneglycol plasmalogen in a rat liver. 3) It is now under the investigation which type of base was bound to the diol phospholipid. The mechanism of the diol lipid synthesis in nature is still unknown, thus it is necessary to have further studies on the conditions under which the diol lipid is synthesized.…”

Section: Polyols and Fatty Acids From The Madg Fractionmentioning

confidence: 99%

Diol Lipids in the Phospholipid Fraction ofLipomyces starkeyiGrown in the Medium Containing 1,2-Propanediol

Suzuki

Hasegawa

1974

Agricultural and Biological Chemistry

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After training for 1,2-propanediol, a yeast, Lipomyces starkeyi, grew well in the media containing the diol, showing a diauxie-like pattern. The yeast phospholipid was converted into monoacetyl-diglyceride by acetolysis. The presence of monoacetyl-mono fatty acyl esters of the diol in this fraction was found by GC-MS. The data suggested that the diol was present as 2-palmitoyl-ester and 2-oleoyl-ester in the form of phospholipid analogue, in which phosphorus bound in I-position of the diol. Molecular species of the phospholipid was also deduced from the GC-MS data. Diol diester was not found in the triglyceride fraction of the yeast.Following the first discovery of a fatty acid ester of 2,3-butanediol, named as coixenolide, by Ukita et al.,11 several kinds of short chain dials, ethyleneglycol, propanediol, butanediol and so on, were detected in lipid hydrolyzates from many biological sources by many investigators. 21 However, only one diol phospholipid had been reported until the recent studies by Bergelson et aU' Little is known about the biogenesis of diol lipids. It has not been known whether a free diol in the medium would be incorporated into the lipid as an alcohol constituent or not.The present investigation was undertaken to find out if the diol supplemented in the cultivation medium would be incorporated into the lipid of the yeast, L. starkeyi. During the course of this experiment, a direct method to distinguish the free diol from the diol lipids became necessary. To resolve this problem, acetolysis method and combined gas chromatot A part of this work was presented at the Annual Meeting of the Agricultural Chemical Society of Japan, held in Tokyo, April, 1973, and also at 9th International Congress of Biochemistry, held in Stockholm, Sweden, July, 1973. Abbreviations used: MADG, monoacetyl-diglyceride; CoM, chloroform-methanol; GC-MS, gas chromatography-mass spectrometry; TLC, thin-layer chromatography; TMS, trimethyl silylether; GLC, gas-liquid chromatography; DEGS, diethyleneglycol succinate polyester. graphy-mass spectrometry were employed. The results showed that diollipids were detected in the phospholipid fraction obtained from the cells harvested at the stages adaptating and consuming 1,2-propanediol. MATERIAL" AND METHODS Microorganism and culture conditions.The microorganism used in this study was Lipomyces starkeyi IFO 0678. In order to adapt L. starkeyi to the new carbon source, it was preliminarily cultured in the following three different media. The first strain was grown in a glucose medium, then transferred to the medium containing 1~~of 1,2-propanediol and 4 % of glucose, and then transferred to 2.5 % each of 1,2-propanediol and glucose. The strain cultivated in the last medium was used in the main culture.The culture medium used in this experiment was as Cultivation was carried out at 30°C under shaking. During the cultivation, the pH of the medium was controlled at approximately 4 to 6 by means of adding 1 N-NaOH. Aliquots of yeast cells were harvested at 100 hr, 121 hr, 168 hr...

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Section: Polyols and Fatty Acids From The Madg Fractionmentioning

confidence: 99%

Diol Lipids in the Phospholipid Fraction ofLipomyces starkeyiGrown in the Medium Containing 1,2-Propanediol

Suzuki

Hasegawa

1974

Agricultural and Biological Chemistry

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Diol Lipids New Types of Naturally Occuring Lipid Substances

Bergel'son¹

1973

Fette, Seifen, Anstrichm.

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Lipids of plants, animals and microorganisms frequently conkain minor amounts of lipophylic derivatives of ethyleneglycol and related lower dihydric alcohols, which mostly have been overlooked in the part. Methods for the quantitative determination of diols in lipid hydrolyzates have been developed. In some particular cases, e.g. lipids of marine invertebrates, regenerating rat liver and young corn seeds comparatively high diol/glycerol ratios were found. Various methods for the structural investigation of diol lipids, including mass-spectrometry and combined GLC-mass-spectrometry are described. The chemical structure of a number of diol lipids including simple neutral lipids, diol galactolipids and diol cholinephosphatides has been clarified, the existence of other types is probable. The biosynthetic pathways of the diol lipids seem to be similar to those of the glycerolipids. Diol-Lipide -Neue Arten von natiirlid, vorkommenden Lipid- SubstanzenLipide von Pflanzen, Tieren und Mikroorganismen enthalten oft kleinere Mengen von lipophilen Derivaten des Athylenglycols und verwandter Diole. die in der Vergangenheit meist iibersehen wurden. Methoden zur quantitativen Bestimmung von Diolen in Lipidhydrolysaten wurden entwidcelt. In Lipiden von wirbellosen Seetieren, regenerierender Rattenleber und jungen Maiskornern wurden verhaltnismaDig hohe DioljGlyzerinwerte gefunden. Verschiedene Methoden zur Strukturaufklarung von Diol-Lipiden einschlieDlich Massen-Spektrometrie und kombinierte GLC-Massen-Spektrometrie werden beschrieben. Die chemische Struktur einer Anzahl von Diol-Lipiden, darunter einfache Neutrallipide, Diol-Galaktolipide und Diol-Cholinphosphatide, wurde aufgeklart ; das Vorkommen anderer Typen ist wahrscheinlich. Die Wege der Biosynthese der Diol-Lipide sheinen denen der Glycerolipide zu ahneln.

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Cholesteryl sulfate in meconium: Inhibitory action on rabbit anti-M and anti-N antisera

Gauster

Tuppy

1983

Monatsh Chem

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Diol lipids

Cited by 22 publications

References 18 publications

Diol Lipids in the Phospholipid Fraction ofLipomyces starkeyiGrown in the Medium Containing 1,2-Propanediol

Diol Lipids in the Phospholipid Fraction ofLipomyces starkeyiGrown in the Medium Containing 1,2-Propanediol

Diol Lipids New Types of Naturally Occuring Lipid Substances

Cholesteryl sulfate in meconium: Inhibitory action on rabbit anti-M and anti-N antisera

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