Naturally occurring ω‐Hydroxyacids

Abstract

x-Hydroxyacids are fatty acids bearing a hydroxyl group on the terminal carbon. They are found in mammals and higher plants and are often involved in providing a permeability barrier, the primary purpose of which is to reduce water loss. Some x-hydroxyacid derivatives may be involved in waterproofing and signalling. The purpose of this review was to survey the known natural sources of x-hydroxyacids. x-Hydroxyacids are produced by two different P450-dependent mechanisms. The longer (30-34 carbons) x-hydroxyacids are produced by chain extension from palmitic acid until the chain extends across the membrane in which the extension is taking place, and then the terminal carbon is hydroxylated. Shorter fatty acids can be hydroxylated directly to produce C16 and C18 x-hydroxyacids found in plants and 20-eicosatetraenoic acid (20-HETE) by a different P450. The C16 and C18 x-hydroxyacids are components of polymers in plants. The long-chain x-hydroxyacids are found in epidermal sphingolipids, in giant-ring lactones from the sebum of members of the equidae, as a component of meibum and in carnauba wax and wool wax.R esum e Les x-hydroxyacides sont des acides gras portant un groupe hydroxyle sur le carbone terminal. Ils sont pr esents chez les mammif eres et les plantes sup erieures et sont souvent impliqu es dans les ph enom enes de barri ere de perm eabilit e, dont le but principal est de r eduire la perte d'eau. Certains d eriv es x-hydroxyacides peuvent etre impliqu es dans l'imperm eabilisation et la signalisation. Le but de cette revue est d' etudier les sources naturelles connues de xhydroxyacides. Les H -hydroxyacides sont produits par deux m ecanismes diff erents P450 d ependants. Les x-hydroxyacides plus longs (30 a 34 atomes de carbone) sont produits par extension de la chaîne a partir de l'acide palmitique jusqu' a ce que la chaîne s' etende a travers la membrane dans laquelle l'extension a lieu, puis le carbone terminal est hydroxyl e. Les acides gras plus courts peuventêtre hydroxyl es directement pour produire des x-hydroxyacides en C16 et C18 trouv es dans les plantes et l'acide 20-eicosat etra eno€ ıque (20-HETE) par un P450 diff erent. Les x-hydroxyacides en C16 et C18 sont des composants de polym eres dans les plantes. Les x-hydroxyacides a longue chaîne se trouvent dans les sphingolipides epidermiques, dans des anneaux g eants des lactones provenant du s ebum des equid es, en tant que constituants du meibum et dans la cire de carnauba et la cire de laine.

Commensal adaptation of yeast Saccharomyces cerevisiae to grape-skin environment

“…This is the rst report on ω-hydroxypalmitic acid assimilation as a carbon source by A. pullulans and several yeast species. Although ω-hydroxylation of fatty acids also occurs in mammals and insects, ωhydroxy fatty acids play a broad and vital biological role in higher plants as major components of cutin and suberin [24][25][26][52][53][54] . Thus, the microbial ability to assimilate ω-hydroxy fatty acids may mainly contribute to symbiotic interactions with terrestrial plants.…”

“…Thus, the microbial ability to assimilate ω-hydroxy fatty acids may mainly contribute to symbiotic interactions with terrestrial plants. In the ω-oxidation process of animals and plants, known as a minor, fatty acid catabolic pathway, a hydroxy group is introduced onto the ω carbon of the medium to long-chain fatty acids 53,54 . The resultant ω-hydroxy fatty acids are oxidized to ωcarboxy fatty acids (i.e., dicarboxylic fatty acids), further degraded through the β-oxidation pathway.…”

Oral Administration of Sodium Nitrate to Metabolic Syndrome Patients Attenuates Mild Inflammatory and Oxidative Responses to Acute Exercise

“…The changes in plasma concentration of 16-HPAL are reported for the first time. ω-Hydroxyacids of saturated and unsaturated fatty acids are produced by cytochrome P450-dependent mechanisms in both plants and in mammals [ 45 ]. The ω-oxidation of saturated fatty acids mainly occurs in liver and kidney cells [ 46 ].…”

Accelerated Alcoholic Fermentation of Intact Grapes by Saccharomyces Cerevisiae in Symbiosis with Microbial Community Inhabiting Grape-skin

“…This is the first report on ω-hydroxypalmitic acid assimilation as a carbon source by A. pullulans and several yeast species. Although ω-hydroxylation of fatty acids also occurs in mammals and insects, ω-hydroxy fatty acids play a broad and vital biological role in higher plants as major components of cutin and suberin [18][19][20][45][46][47] . Thus, the microbial ability to assimilate ω-hydroxy fatty acids may mainly contribute to symbiotic interactions with terrestrial plants.…”

“…Thus, the microbial ability to assimilate ω-hydroxy fatty acids may mainly contribute to symbiotic interactions with terrestrial plants. In the ω-oxidation process of animals and plants, known as a minor, fatty acid catabolic pathway, a hydroxy group is introduced onto the ω carbon of the medium to long-chain fatty acids 46,47 . The resultant ω-hydroxy fatty acids are oxidized to ω-carboxy fatty acids (i.e., dicarboxylic fatty acids), further degraded through the β-oxidation pathway.…”