title: Rapid formation of 4-hydroxy-2-nonenal, malondialdehyde, and phosphatidylcholine aldehyde from phospholipid hydroperoxide by hemoproteins.
abstract: 4-Hydroxy-2-nonenal (HNE) and malondialdehyde (MDA) are well-known toxic products of lipid peroxidation. Phosphatidylcholine aldehydes are also known as oxidation products of phosphatidylcholine. The mechanism of the formation of these compounds in vivo has been a long-standing question. We observed that the rapid reaction of hemoproteins (methemoglobin, metmyoglobin, and cytochrome c) with 1-palmitoyl-2-(13-hydroperoxy-cis-9, trans-11-octadecadienoyl) phosphatidylcholine (PLPC-OOH), having a hydroperoxylinoleoyl residue, generated HNE, MDA, and the phosphatidylcholine aldehyde 1-palmitoyl-2-(9-oxononanoyl) phosphatidylcholine. The efficiencies (mol% yield) of the formation of HNE and MDA from decomposed PLPC-OOH by methemoglobin, metmyoglobin, and cytochrome c after incubation for 10 min were 1.6, 1.0, and 1.0% for HNE and 1.2, 0.6, and 0.9% for MDA, respectively. When 1-palmitoyl-2-linoleoyl phosphatidylcholine was incubated with lipoxidase and methemoglobin, the formation of HNE and the phosphatidylcholine aldehyde 1-palmitoyl-2-(9-oxononanoyl) phosphatidylcholine was observed. When 1-palmitoyl-2-arachidonyl phosphatidylcholine was used instead of 1-palmitoyl-2-linoleoyl phosphatidylcholine, the phosphatidylcholine aldehyde 1-palmitoyl-2-oxovaleroyl phosphatidylcholine was obtained. These data suggest that HNE and phosphatidylcholine aldehydes might be rapidly formed from phosphatidylcholine by lipoxygenase and hemoproteins. Furthermore, hemichrome, converted from methemoglobin by deoxycholic acid and ursodeoxycholic acid, showed marked decomposition of HNE. These results suggest that hemoproteins are related to both the formation and the decomposition of HNE.
authors.affiliation: Hokkaido Institute of Public Health, Kita 12, Nishi 6, Kita-ku, Sapporo 060-0819, Japan.
authors.forename: Takaaki
authors.initials: T
authors.lastname: Hayashi
authors.forename: Koji
authors.initials: K
authors.lastname: Uchida
authors.forename: Gen
authors.initials: G
authors.lastname: Takebe
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Takahashi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000975:Antioxidants / Q000494:pharmacology; D003840:Deoxycholic Acid / Q000737:chemistry; D005609:Free Radicals; D006420:Hemeproteins / Q000737:chemistry*; D006454:Hemoglobins / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry*; D050356:Lipid Metabolism; D015227:Lipid Peroxidation; D008074:Lipoproteins / Q000737:chemistry; D008084:Lipoxygenase / Q000737:chemistry / Q000378:metabolism; D008315:Malondialdehyde / Q000737:chemistry*; D008706:Methemoglobin / Q000737:chemistry; D008956:Models, Chemical; D010713:Phosphatidylcholines / Q000737:chemistry*; D010742:Phospholipid Ethers / Q000494:pharmacology; D013997:Time Factors; D014466:Ultraviolet Rays; D014580:Ursodeoxycholic Acid / Q000737:chemistry
chemical_list: C400184:1-palmitoyl-2-(5-oxovaleroyl)-sn-glycero-3-phosphorylcholine; D000447:Aldehydes; D000975:Antioxidants; D005609:Free Radicals; D006420:Hemeproteins; D006454:Hemoglobins; D008074:Lipoproteins; D010713:Phosphatidylcholines; D010742:Phospholipid Ethers; C001332:hemichrome; C057590:phosphatidylcholine hydroperoxide; D003840:Deoxycholic Acid; D008315:Malondialdehyde; C055402:1-palmitoyl-2-linoleoylphosphatidylcholine; D014580:Ursodeoxycholic Acid; D008706:Methemoglobin; D006861:Hydrogen Peroxide; D008084:Lipoxygenase; C027576:4-hydroxy-2-nonenal