Autoxidation of phosphatidylcholine liposomes. 1982

G S Wu, and R A Stein, and J F Mead

Autoxidation of pure soybean phosphatidylcholine liposomes at 40 C was found to proceed without an observed induction period, but otherwise, the rates of disappearance of the linoleic acid (70% of total) and linolenic acid (6% of total) followed typical autocatalytic kinetics. Incorporation of 0.05 mol % of tocopherol into the liposomes produced an induction period of about 7 hr under the condition used for the incubation. The products formed from the autoxidation of pure soybean phosphatidylcholine liposomes were mostly 9- and 13-hydroperoxyoctadecadienoates (isolated as hydroxy esters). The yield of hydroperoxides with cis,trans configuration was about the same as those with trans,trans configuration throughout incubation period. After extensive autoxidation, a large quantity of trihydroxyoctadecenoate was also produced. When a large quantity of dipalmitoyl phosphatidylcholine was incorporated into soybean phosphatidylcholine liposomes, the rate of autoxidation decreased and was found to conform to apparent first-order kinetics. In this system, the yield of trans,trans hydroperoxides was much greater than that of cis,trans isomers at all stages of autoxidation. Late in the autoxidation of the mixed liposomes, both trihydroxyoctadecenoate and hydroxyepoxyoctadecenoate were produced in substantial quantities.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008081 Liposomes Artificial, single or multilaminar vesicles (made from lecithins or other lipids) that are used for the delivery of a variety of biological molecules or molecular complexes to cells, for example, drug delivery and gene transfer. They are also used to study membranes and membrane proteins. Niosomes,Transferosomes,Ultradeformable Liposomes,Liposomes, Ultra-deformable,Liposome,Liposome, Ultra-deformable,Liposome, Ultradeformable,Liposomes, Ultra deformable,Liposomes, Ultradeformable,Niosome,Transferosome,Ultra-deformable Liposome,Ultra-deformable Liposomes,Ultradeformable Liposome
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D010713 Phosphatidylcholines Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety. Choline Phosphoglycerides,Choline Glycerophospholipids,Phosphatidyl Choline,Phosphatidyl Cholines,Phosphatidylcholine,Choline, Phosphatidyl,Cholines, Phosphatidyl,Glycerophospholipids, Choline,Phosphoglycerides, Choline
D002849 Chromatography, Gas Fractionation of a vaporized sample as a consequence of partition between a mobile gaseous phase and a stationary phase held in a column. Two types are gas-solid chromatography, where the fixed phase is a solid, and gas-liquid, in which the stationary phase is a nonvolatile liquid supported on an inert solid matrix. Chromatography, Gas-Liquid,Gas Chromatography,Chromatographies, Gas,Chromatographies, Gas-Liquid,Chromatography, Gas Liquid,Gas Chromatographies,Gas-Liquid Chromatographies,Gas-Liquid Chromatography
D013025 Glycine max An annual legume. The SEEDS of this plant are edible and used to produce a variety of SOY FOODS. Soy Beans,Soybeans,Bean, Soy,Beans, Soy,Soy Bean,Soybean
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

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