Odd-numbered very-long-chain fatty acids from the microbial, animal and plant kingdoms

Řezanka, Tomáš; Sigler, Karel

doi:10.1016/j.plipres.2009.03.003

Cited by 185 publications

(144 citation statements)

References 354 publications

Supporting

Mentioning

133

Contrasting

Unclassified

Order By: Relevance

“…In fact the even-numbered n-alkanes have optimal intermolecular interactions at both ends, while in odd-numbered the intermolecular distances are not optimal at both ends and this results in weaker intermolecular interactions [29]. In most marine organisms and bacteria an even or odd carbon-chain preference is found in fatty acids and alcohols, while for the hydrocarbon odd chains predominate [30,31]. In organic chemistry this effect occurs most commonly in the solubility of solutes.…”

Section: Specificity In Oil Chain Lengthmentioning

confidence: 99%

Two sides of the coin. Part 1. Lipid and surfactant self-assembly revisited

Ninham

Larsson

Nostro

2017

Colloids and Surfaces B: Biointerfaces

View full text Add to dashboard Cite

a b s t r a c tHofmeister, specific ion effects, hydration and van der Waals forces at and between interfaces are factors that determine curvature and microstructure in self assembled aggregates of surfactants and lipids; and in microemulsions. Lipid and surfactant head group interactions and between aggregates vary enormously and are highly specific. They act on the hydrophilic side of a bilayer, micelle or other self assembled aggregate. It is only over the last three decades that the origin of Hofmeister effects has become generally understood. Knowledge of their systematics now provides much flexibility in designing nanostructured fluids.The other side of the coin involves equally specific forces. These (opposing) forces work on the hydrophobic side of amphiphilic interfaces. They are due to the interaction of hydrocarbons and other "oils" with hydrophobic tails of surfactants and lipids. The specificity of oleophilic solutes in microemulsions and lipid membranes provides a counterpoint to Hofmeister effects and hydration. Together with global packing constraints these effects determine microstructure.Another factor that has hardly been recognised is the role of dissolved gas. This introduces further, qualitative changes in forces that prescribe microstructure.The systematics of these effects and their interplay are elucidated. Awareness of these competing factors facilitates formulation of self assembled nanostructured fluids. New and predictable geometries that emerge naturally provide insights into a variety of biological phenomena like anaesthetic and pheromone action and transmission of the nervous impulse (see Part 2).

show abstract

Section: Specificity In Oil Chain Lengthmentioning

confidence: 99%

Two sides of the coin. Part 1. Lipid and surfactant self-assembly revisited

Ninham

Larsson

Nostro

2017

Colloids and Surfaces B: Biointerfaces

View full text Add to dashboard Cite

show abstract

Section: Nomenclature and Structure Of Vlc-fa And Vlc-pufamentioning

confidence: 99%

“…For the most part, trivial names of the FA such as docosahexaenoic acid (DHA, or 22:6n3) or arachidonic acid (20:4n6) still prevail and are more commonly used ( 9 ). Also, because most studies done previously were focused on FA with a maximum of 22 carbons, most studies refer to FA such as 20:4n6, 22:5n3, and 22:6n3 as either LC-PUFA or VLC-PUFA ( 3,9,21,40,41 ). With advancement in science and technology, coupled with improvement in analytical methods for detection, identifi cation and quantifi cation of FA with carbons chain longer than C22 by GC-MS and/or LC/ ESI-MS and LC-MS/APCI, among others, we are now in a new era of beginning to appreciate the presence and possible function of FA with carbon chains longer than C22 ( 42 ).…”

Section: Nomenclature and Structure Of Vlc-fa And Vlc-pufamentioning

confidence: 99%

“…They are found in most living organisms from humans to autotrophic and heterotrophic lower organisms, including microalgae, sponges, bacteria, and fungi ( 1,9,(11)(12)(13)(14)(15). VLC-FA are found mainly in seed oils, plant waxes, cutin, suberin, skin, hair, and wax glands ( 1 ), whereas VLC-PUFA are found primarily in retina, brain ( 1, 16 ), testis, and spermatozoa ( 17-19 ).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Retinal very long-chain PUFAs: new insights from studies on ELOVL4 protein

Agbaga

Mandal

Anderson

2010

Journal of Lipid Research

142

141

View full text Add to dashboard Cite

This article is available online at http://www.jlr.org tively rare compared with the abundance of FA containing 16-22 carbons, they are widely distributed in higher plants and animals ( 1-10 ). They are found in most living organisms from humans to autotrophic and heterotrophic lower organisms, including microalgae, sponges, bacteria, and fungi ( 1,9,(11)(12)(13)(14)(15). VLC-FA are found mainly in seed oils, plant waxes, cutin, suberin, skin, hair, and wax glands ( 1 ), whereas VLC-PUFA are found primarily in retina, brain ( 1, 16 ), testis, and spermatozoa ( 17-19 ).The unusually long hydrocarbon chains with 3 -9 double bonds, which are prone to oxidative damage, combined with the small quantities found in mammalian tissues, have made them diffi cult to isolate and analyze in detail over the years ( 9 ). Very little is therefore known about the metabolism and function of VLC-PUFA and VLC-FA in mammals, except for their increase in disorders of peroxisomal function ( 3,16,20,21 ), as components of the secretions of meibomian glands (22)(23)(24)(25)(26)(27), and their reduction in animal models of autosomal dominant Stargardt-like macular dystrophy (STGD3) ( 28-32 ), a juvenile form of macular degeneration. In contrast, the roles of long-chain PUFA (LC-PUFA) with carbon chains that range from C18 to C24 are fairly well understood, especially in the retina and other neural tissues. A detailed account on the role and function of LC-PUFA in the retina was reviewed earlier (33)(34)(35)(36).Recent interest in the molecular and physiological roles of VLC-PUFA in the retina came from the fi nding that the gene associated with STGD3 shared sequence homologies with genes involved in FA elongation ( 37,38 ) Abbreviations: AOX, acyl-CoA oxidase; DHA or 22:6n3, docosahexaenoic acid; ELOVL, elongation of very long-chain FA; ELOVL4, elongation of very long-chain FA-4; ERG, electroretinogram; LC-PUFA, long-chain PUFA; PC, phosphatidylcholine; ROS, retinal outer segments; RPE, retinal pigment epithelium; STGD1, recessive Stargardt degeneration; STGD3, autosomal dominant Stargardt-like macular dystrophy; VLC-FA, very long-chain saturated or monounsaturated FA; VLC-PUFA, very long-chain PUFA.

show abstract

“…Lipids with an odd number of carbons were not considered because of their low occurrence in higher order animals [40].…”

Section: Discussionmentioning

confidence: 99%

Advanced Mass Calibration and Visualization for FT-ICR Mass Spectrometry Imaging

Smith

Харченко

Konijnenburg

et al. 2012

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

Mass spectrometry imaging by Fourier transform ion cyclotron resonance (FT-ICR) yields hundreds of unique peaks, many of which cannot be resolved by lower performance mass spectrometers. The high mass accuracy and high mass resolving power allow confident identification of small molecules and lipids directly from biological tissue sections. Here, calibration strategies for FT-ICR MS imaging were investigated. Sub-parts-per-million mass accuracy is demonstrated over an entire tissue section. Ion abundance fluctuations are corrected by addition of total and relative ion abundances for a root-mean-square error of 0.158 ppm on 16,764 peaks. A new approach for visualization of FT-ICR MS imaging data at high resolution is presented. The "Mosaic Datacube" provides a flexible means to visualize the entire mass range at a mass spectral bin width of 0.001 Da. The high resolution Mosaic Datacube resolves spectral features not visible at lower bin widths, while retaining the high mass accuracy from the calibration methods discussed.

show abstract

Odd-numbered very-long-chain fatty acids from the microbial, animal and plant kingdoms

Cited by 185 publications

References 354 publications

Two sides of the coin. Part 1. Lipid and surfactant self-assembly revisited

Two sides of the coin. Part 1. Lipid and surfactant self-assembly revisited

Retinal very long-chain PUFAs: new insights from studies on ELOVL4 protein

Advanced Mass Calibration and Visualization for FT-ICR Mass Spectrometry Imaging

Contact Info

Product

Resources

About