Platelet-activating Factor (PAF)-like Phospholipids Formed during Peroxidation of Phosphatidylcholines from Different Foodstuffs

Tanaka, Tamotsu; Tokumura, Akira; Tsukatani, Hiroaki

doi:10.1271/bbb.59.1389

Cited by 23 publications

(15 citation statements)

References 7 publications

(7 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The PAF-like activity due to the secondary oxidation products of salmon roe PC was found to be about 17 pmol PAF (C 16 ) equivalent/µmol parent PC, which is approximately equal to the value for sea urchin PC, but about ten times higher than that of hen egg yolk PC [8]. Conversely, salmon roe is enriched in DHA, but the percentage of its alkyl-acyl subclass is low.…”

Section: Paf-like Lipids Are Generated After Peroxidation Of Pcmentioning

confidence: 80%

Platelet‐activating factor (PAF)‐like oxidized phospholipids: Relevance to atherosclerosis

Tokumura¹,

Sumida²,

Toujima³

et al. 2000

BioFactors

Self Cite

View full text Add to dashboard Cite

Lipid peroxidation is involved in the pathogenesis of chronic diseases including atherosclerosis. Oxidized lipoprotein has diverse biological activities and is believed to initiate atheroma formation and maturate fatty plaque. The active components of oxidized lipoproteins still remain to be clarified, but a likely candidate is the phosphatidylcholine (PC) having an sn-2-short-chain acyl group with a methyl, hydroxyl, aldehydic or carboxylic terminal. These unique PCs, formed by oxidative fragmentation of the polyunsaturated acyl group of the parent PC in liposomes, low density lipoproteins and blood plasma, induce platelet aggregation through the activation of the receptor for platelet-activating factor (PAF), due to their resemblance in structure with PAF. We have found that PAF-like lipids regulate DNA synthesis and production of nitric oxide independently of the activation of the PAF receptor in vascular smooth muscle cells. Regulation of vascular cell function through two distinct signaling pathways mediated by PAF-like lipids provides new insight into the mechanism of induction of atherosclerosis.

show abstract

Section: Paf-like Lipids Are Generated After Peroxidation Of Pcmentioning

confidence: 80%

Platelet‐activating factor (PAF)‐like oxidized phospholipids: Relevance to atherosclerosis

Tokumura¹,

Sumida²,

Toujima³

et al. 2000

BioFactors

Self Cite

View full text Add to dashboard Cite

show abstract

“…This large family of oxidation products has now also been observed in oxidized LDL (14, 18 -20), human plasma (21), and food products (22). They are found in atherosclerotic lesions (13) and in the blood of animals (23) and humans (24) exposed to cigarette smoke.…”

Section: Lipid Oxidationmentioning

confidence: 90%

Biologically Active Oxidized Phospholipids

McIntyre¹,

Zimmerman²,

Prescott³

1999

Journal of Biological Chemistry

145

105

View full text Add to dashboard Cite

Oxidants and free radicals are deleterious in many ways, and organisms employ numerous approaches to block their production or limit their damage. Hydrogen atoms adjacent to olefinic bonds are susceptible to oxidative attack and those between unconjugated olefinic bonds especially so. Lipids are a rich source of these bonds and so are a primary target for oxidative reactions. Lipid oxidation is problematic as the many oxidative chemical reactions are not controlled and constrained by enzymes and may show exponential reaction rates, and some of the products of the attack are highly reactive species that modify proteins and DNA. This review summarizes current information about another outcome of the uncontrolled attack on cellular and circulating phospholipids, the generation of potent biologically active compounds that activate components of the immune and inflammatory systems.The biologically active species discussed here include oxidized phosphatidylcholines with biologic activity similar to platelet-activating factor (PAF), 1 oxidized phosphatidylcholines that stimulate responses through ways other than the PAF receptor, and the lysophosphatidylcholines that result from the enzymatic metabolism of these modified phospholipids. Oxidation products that mimic the properties of a wide variety of arachidonate metabolites are discussed in a separate review in this series (FitzGerald et al. (85)), as is a study of the effects of cholesterol oxidation (Chisolm et al. (86)). We will briefly mention the role of PAF acetylhydrolase in the catabolism of oxidized phospholipids. With the structures of some biologically active oxidation products deciphered, there is physical evidence to show that oxidatively modified phospholipids accumulate in vivo. This suggests that potent biologic mediators can arise from uncontrolled chemical reactions when the antioxidant defenses of the organism are overwhelmed. One area where such newly formed species subvert physiologic events is atherogenesis, but exposure to cigarette smoke, reperfusion injury, and stroke are also likely candidates for inappropriate events initiated or propagated by biologically active oxidized phospholipids. Lipid OxidationOxidative reactions of free fatty acids have been defined (e.g. Refs. 1-3), and oxidation of fatty acyl residues esterified in phospholipids appears to proceed in a similar fashion. The initial oxidative attack on polyunsaturated fatty acids generates alkyl radicals and then with the addition of oxygen, alkoxy radicals and peroxides. Arachidonate when oxidized enzymatically generates hydroperoxyeicosatetraenoates, hydroxyeicosatetraenoates, prostaglandins, and leukotrienes. A larger series of stereo and positional isomers known as isoprostanes, isothromboxanes, and isoleukotrienes (4, 5) is produced when arachidonate is nonenzymatically oxidized by a series of competing chemical reactions.

show abstract

“…According to Paltauf (28), the dietary 1-Oalkyl-sn-glycerols are preferentially incorporated into the glycerophosphoethanolamine in vivo, which, however, could be Nmethylated to yield the corresponding GroPCho. Tanaka et al (4) have discussed the PAF-like phospholipids formed during peroxidation of diacylglycerophosphocholines from different foodstuffs. A short-chain FA terminating in an aldehyde, hydroxyl, or carboxyl group located in the sn-2-position of 1alkyl or 1-acyl glycerophosphocholine can mimic the action of natural PAF.…”

Section: Table 4 Composition Of Molecular Species Of Dnph-derivatizedmentioning

confidence: 99%

1‐O‐alkyl‐2‐(ω‐oxo)acyl‐sn‐glycerols from shark oil and human milk fat are potential precursors of PAF mimics and GHB

Hartvigsen

Ravandi

Harkewicz

et al. 2006

Lipids

View full text Add to dashboard Cite

This study examines the feasibility that peroxidation and lipolysis of 1-O-alkyl-2,3-diacyl-sn-glycerols (DAGE) found in shark liver oil and human milk fat constitutes a potential source of dietary precursors of platelet activating factor (PAF) mimics and of gamma-hydroxybutyrate (GHB). Purified DAGE were converted into 1-O-alkyl-2-acyl-sn-glycerols by pancreatic lipase, without isomerization, and transformed into 1-O-alkyl-2-oxoacyl-sn-glycerols by mild autooxidation. The various core aldehydes without derivatization, as well as the corresponding dinitrophenylhydrazones, were characterized by chromatographic retention time and diagnostic ions by online electrospray mass spectrometry. Core aldehydes of oxidized shark liver oil yielded 23 molecular species of 1-O-alkyl-sn-glycerols with short-chain sn-2 oxoacyl groups, ranging from 4 to 13 carbons, some unsaturated. Autooxidation of human milk fat yielded 1-O-octadecyl-2-(9-oxo)nonanoyl-sn-glycerol, as the major core aldehyde. Because diradylglycerols with short fatty chains are absorbed in the intestine and react with cytidine diphosphate-choline in the enterocytes, it is concluded that formation of such PAF mimics as 1-O-alkyl-2-(omega-oxo)acyl-sn-glycerophosphocholine from unsaturated dietary DAGE is a realistic possibility. Likewise, a C4 core alcohol produced by aldol-keto reduction of a C4 core aldehyde constitutes a dietary precursor of the neuromodulator and recreational drug GHB, which has not been previously pointed out.

show abstract

Platelet-activating Factor (PAF)-like Phospholipids Formed during Peroxidation of Phosphatidylcholines from Different Foodstuffs

Cited by 23 publications

References 7 publications

Platelet‐activating factor (PAF)‐like oxidized phospholipids: Relevance to atherosclerosis

Platelet‐activating factor (PAF)‐like oxidized phospholipids: Relevance to atherosclerosis

Biologically Active Oxidized Phospholipids

1‐O‐alkyl‐2‐(ω‐oxo)acyl‐sn‐glycerols from shark oil and human milk fat are potential precursors of PAF mimics and GHB

Contact Info

Product

Resources

About