Waxes of the social spiderAnelosimus eximius(Araneae, Theridiidae): Abundance of noveln-propyl esters of long-chain methyl-branched fatty acids

The morphology and molecular conformation of monolayers of straight chain and methyl-branched fatty acids have been investigated by VSFS and AFM, revealing domains in the latter case, due to inverse micellar packing constraints.

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Composition of long-chain bases in sphingomyelin of the guinea pig Harderian gland

Biochemistry and Cell Biology ◽

10.1139/o90-021 ◽

1990 ◽

Vol 68 (1) ◽

pp. 154-160 ◽

Cited By ~ 17

Author(s):

E. Yasugi ◽

T. Kasama ◽

M. Shibahara ◽

Y. Seyama

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Guinea Pig ◽

High Performance ◽

Minor Component ◽

Harderian Gland ◽

Hydroxy Acids ◽

Branched Fatty Acids ◽

Methyl Branched Fatty Acids ◽

Long Chain

Sphingomyelin from the guinea pig Harderian gland was isolated and characterized. The purified sphingomyelin gave a broad spot on thin-layer chromatography. The fatty acid composition of the whole sphingomyelin was 71% nonhydroxy acids and 29% 2-hydroxy acids. Methyl-branched fatty acids were only 2% of the total acids. The long-chain bases were composed of straight-chain sphingenines (50%) and sphinganines (6%). Methyl-branched long-chain bases were 44% of the bases. The sphingomyelin was further separated into four fractions (I, II, III, IV) by high-performance liquid chromatography. The ratio of fractions I, II, III, and IV was approximately 2:5:2:1, respectively. The fatty acids of fractions I and II consisted of nonhydroxy acids and those of fractions III and IV were 2-hydroxy acids. The long-chain bases of fractions I and III were sphinganines including 10-, 9-, and 8-methylsphinganines and anteiso-sphinganines. These methyl-branched bases occupied about 70% of the total sphinganines. The long-chain bases of fractions II and IV consisted of sphingenines. The methyl-branched unsaturated bases were only 30% of the total sphingenines, all in the anteiso-form. Thus, the sphingomyelin obtained from guinea pig Harderian gland had complex compositions of fatty acids and long-chain bases, and half the number of long-chain bases had methyl branches. The methyl-branched fatty acids were only a minor component. These characteristics are similar to those of cerebrosides isolated from the same source.Key words: long chain base, fatty acid, sphingomyelin, guinea pig, Harderian gland.

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Inactivation of the Peroxisomal Multifunctional Protein-2 in Mice Impedes the Degradation of Not Only 2-Methyl-branched Fatty Acids and Bile Acid Intermediates but Also of Very Long Chain Fatty Acids

Journal of Biological Chemistry ◽

10.1074/jbc.m001994200 ◽

2000 ◽

Vol 275 (21) ◽

pp. 16329-16336 ◽

Cited By ~ 133

Author(s):

Myriam Baes ◽

Steven Huyghe ◽

Peter Carmeliet ◽

Peter E. Declercq ◽

Désiré Collen ◽

...

Keyword(s):

Fatty Acids ◽

Bile Acid ◽

Long Chain Fatty Acids ◽

Multifunctional Protein ◽

Branched Fatty Acids ◽

Methyl Branched Fatty Acids ◽

Long Chain ◽

Chain Fatty Acids

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Anaerobic 1-Alkene Metabolism by the Alkane- and Alkene-Degrading Sulfate Reducer Desulfatibacillum aliphaticivorans Strain CV2803T

Applied and Environmental Microbiology ◽

10.1128/aem.01097-07 ◽

2007 ◽

Vol 73 (24) ◽

pp. 7882-7890 ◽

Cited By ~ 25

Author(s):

Vincent Grossi ◽

Cristiana Cravo-Laureau ◽

Alain Méou ◽

Danielle Raphel ◽

Frédéric Garzino ◽

...

Keyword(s):

Fatty Acids ◽

Inorganic Carbon ◽

Direct Evidence ◽

Gas Chromatography Mass Spectrometry ◽

Sulfate Reducing ◽

Branched Fatty Acids ◽

Initial Activation ◽

Fumarate Addition ◽

Chain Lengths ◽

Methyl Branched Fatty Acids

ABSTRACT The alkane- and alkene-degrading, marine sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803T, known to oxidize n-alkanes anaerobically by fumarate addition at C-2, was investigated for its 1-alkene metabolism. The total cellular fatty acids of this strain were predominantly C-(even number) (C-even) when it was grown on C-even 1-alkenes and predominantly C-(odd number) (C-odd) when it was grown on C-odd 1-alkenes. Detailed analyses of those fatty acids by gas chromatography-mass spectrometry after 6- to 10-week incubations allowed the identification of saturated 2- and 4-ethyl-, 2- and 4-methyl-, and monounsaturated 4-methyl-branched fatty acids with chain lengths that correlated with those of the 1-alkene. The growth of D. aliphaticivorans on (per)deuterated 1-alkenes provided direct evidence of the anaerobic transformation of these alkenes into the corresponding 1-alcohols and into linear as well as 10- and 4-methyl-branched fatty acids. Experiments performed with [13C]bicarbonate indicated that the initial activation of 1-alkene by the addition of inorganic carbon does not occur. These results demonstrate that D. aliphaticivorans metabolizes 1-alkene by the oxidation of the double bond at C-1 and by the subterminal addition of organic carbon at both ends of the molecule [C-2 and C-(ω-1)]. The detection of ethyl-branched fatty acids from unlabeled 1-alkenes further suggests that carbon addition also occurs at C-3. Alkylsuccinates were not observed as potential initial intermediates in alkene metabolism. Based on our observations, the first pathways for anaerobic 1-alkene metabolism in an anaerobic bacterium are proposed. Those pathways indicate that diverse initial reactions of 1-alkene activation can occur simultaneously in the same strain of sulfate-reducing bacterium.

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