2-linoleoyl glycerol

Ben-Shabat and co-workers (1998) have reported that in the spleen, as in the brain and gut, 2-AG is accompanied by several 2-acyl-glycerol esters, two major ones being 2-linoleoyl-glycerol (2-Lino-Gl) and 2-palmitoyl-glycerol (2-Palm-Gl). These two esters do not bind to the cannabinoid receptors. 

Figure 25.6. Ion trap mass spectrum of ESI-MS3 of [RLR + Li - RCOOH]+ at m/z 623.5. For abbreviations, see Figures 25.2 and 25.3. L CH=CHCOOH is oc,p-unsaturated linoleic acid from the sn-2 position. Both L and LCOOH are linoleic acid. RLR here is diricinoleoy-linoleoyl-glycerol (non-stereospecific) from castor oil included RRL and LRR if any.

Palm oil contains 6-10 % of tri-saturated fatty acids (SSS), especially tripalmitoil glycerol (PPP). Saturated fraction corresponds to 1-5 % of lauric and myristic acid and 17-23 % to palmitic acid (C16 0) in sn-2 position, while the myristic (C14 0) and the stearic (C18 0) in 1 and 3 position [23]. The unsaturated fraction represents 44-50 % of di-unsaturated fatty acids (SSU or SUS) dipalmitoyl oleoyl glycerol (POP) and dipalmitoyl linoleoyl glycerol (PLP) 38-42 % diunsaturated (SUU or USU) POO and PLO, palmitoyl dioleoyl glycerol and... 

Fig. 12.41. Positive-ion APCI mass spectra of (a) triolein (OOO) and (b) l(3)-palmitoyl-2-stearoyl-3(l)-linoleoyl glycerol (PSL) from soybean oil. The ion in (a) is a solvent...

The principal components of oils and fats on which all the physical and chemical properties depend are the TAG molecules. The TAGs are in turn made up of a variety of fatty acids esterified to the hydroxyl groups on glycerol molecules. TAG profiles of morama bean oil has been carried out by Mitei et ah (2008) who found seven major TAG classes, with the dominating classes being C54 4, C54 3, and C52 3. Occupancy of the sn-1 and sn-3 positions is 45.0% saturated, 38.4% oleoyl, and 16.6% linoleoyl. The sn-2 position is occupied by oleoyl (56.4%) and linoleoyl (43.6%). 

Stearoyl, 2-linoleoyl, 3-palmitoyl glycerol, a mixed triacylglycerol... 

Figure 8-9 Differential scanning calorimetric curves for l-stearoyl-2-linoleoyl-sw-glycerol. (A) Crystals of the compound grown from a hexane solution were heated from -10° to 35°C at a rate of 5°C per minute and the heat absorbed by the sample was recorded. (B) The molten lipid was cooled from 35° to -10°C at a rate of 5° per minute and the heat evolved was recorded as the lipid crystallized in the a phase and was then transformed through two sub-a phases. (C) The solid was reheated. From Di and Small.87 Courtesy of Donald M. Small.

Regarding the lipid composition of phosphatidyhnositols, the mammalian PIPn carry stearic and arachidonic acid esters at the glycerol sn-1 and i n-2-positions, respectively (11). The composition of inositol phospholipids isolated from plants varies from those present in mammalian tissues because they contain linoleoyl residue at the 5 n-2-position and palmitoyl residue at the i n-l-position. 

Glycerophospholipids (PL) are abundant lipid components found in Nature [1]. Most vegetable oils, fish oil and egg yolk are particularly rich in mixtures of phospholipids. They are characterized by the presence of a polar head and two fatty acid chains in the apolar part of the molecule. The two acyl chains mainly consist of saturated fatty acid residues in the snl position and mainly (poly)unsaturated fatty acid chains in the sn2 position. Mixtures of phospholipids at low cost are obtained from the degumming process of vegetable oils. Lecithin, the main component of the mixture, has the polar head characterized by the choline residue. It is usually defined as phosphatidyl choline (PC) and it is understood that the composition of the apolar part is composed of mixtures of fatty acid residues dependent to a large extent on the source of the raw material (fatty acid chains composition of PC from soy beans palmitic 11.6%, stearic 3.4%, oleic 4.6%, linoleic 66.4%, linolenic 8.7%). Scheme 1 shows a PC with two defined acyl chains at the glycerol backbone l-palmitoyl-2-linoleoyl-5n-glycero-3-phosphocholine (PLPC). 

ADP -I- l-palmitoyl-2-arachidonoyl-sn-glycerol 3-phosphate ATP -I- l-palmitoyl-2-linoleoyl-sn-glycerol <7> (<7>, enzyme type I activity is 116% of the activity with rac-l,2-dioleoylglycerol, enzyme type II activity is 86% of the activity with rac-l,2-dioleoylglycerol [16]) (Reversibility <7> [16]) [16]... 

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