Disease relevance of palmitoleic acid

• Palmitoleate is not present in lipid A isolated from Escherichia coli grown at 30 degrees C or higher, but it comprises approximately 11% of the fatty acyl chains of lipid A in cells grown at 12 degrees C. The appearance of palmitoleate at 12 degrees C is accompanied by a decline in laurate from approximately 18% to approximately 5.5% [1].
• Liver microsomal fatty-acid composition in hyperthyroidism is altered with significantly increased proportions of stearate and arachidonate and decreased proportions of palmitate, palmitoleate, linoleate (C18:2) and eicosa-8,11,14-trienoate (C20:3) [2].

High impact information on palmitoleic acid

• Unsaturated NEFAs (palmitoleate, oleate, and linoleate) did not promote apoptosis but prevented stearate-induced apoptosis (P < 0.05; n = 4) [3].
• Strains lacking lpxP fail to incorporate palmitoleate into their lipid A at 12 degrees C but make normal amounts of hexa-acylated lipid A and are viable [4].
• Stearoyl-CoA desaturase (SCD) is a microsomal enzyme required for the biosynthesis of oleate and palmitoleate, which are the major monounsaturated fatty acids of membrane phospholipids, triglycerides, and cholesterol esters [5].
• The replacement of laurate with palmitoleate in lipid A may reflect the desirability of maintaining the optimal outer membrane fluidity at 12 degrees C [1].
• Stearoyl-CoA desaturase (SCD) is a microsomal enzyme involved in the biosynthesis of oleate and palmitoleate [6].

Biological context of palmitoleic acid

• However, unlike palmitoleate, elevation of cAMP was unable to prevent the cytotoxic actions of palmitate since it caused a diversion of the pathway of cell death from apoptosis to necrosis [7].

Anatomical context of palmitoleic acid

• During the differentiation of 3T3-L1 preadipocytes into adipocytes, SCD1 and SCD2 mRNAs are induced concomitant with increased de novo synthesis of palmitoleate and oleate [8].
• Differential effects of palmitate and palmitoleate on insulin action and glucose utilization in rat L6 skeletal muscle cells [9].

Associations of palmitoleic acid with other chemical compounds

• Stimulation of Sr2+ accumulation was not evident following enrichment of S. cerevisiae with either palmitoleate (16:1), linolenate (18:3) (n-3 and n-6 isomers), or eicosadienoate (20:2) (n-6 and n-9 isomers) [10].
• [1-14C]palmitic acid was aerobically converted to palmitoleate and cis-vaccenate, and the radioactivities on their carboxyl carbons were 100 and 43%, respectively, of the total radioactivity in the fatty acids [11].

Gene context of palmitoleic acid

• Stearoyl-CoA desaturase (SCD) is a microsomal enzyme required for the biosynthesis of oleate (C18:1) and palmitoleate (C16:1) which are the major monounsaturated fatty acids of membrane phospholipids, triglycerides and cholesterol esters [12].
• Stearoyl-CoA desaturase (SCD) is expressed at high levels in several human tissues and is required for the biosynthesis of oleate (18:1) and palmitoleate (16:1) [13].
• Comparison of Arrhenius plots of the oxidation of [U-14C]palmitoleate by whole cells and acyl-CoA synthetase activity with palmitoleate as substrate demonstrated that the two exhibited virtually identical Arrhenius activation energies and temperature optima [14].
• Palmitoleate inhibited remarkably LDH, MDH, ICDH and G6P-DH [15].

Analytical, diagnostic and therapeutic context of palmitoleic acid

• The crystal structure of the palmitoleate-bound A264E mutant reveals that substrate binding promotes heme ligation by Glu(264), with little other difference from the palmitoleate-bound wild-type structure observable [16].

References