The inhibitory mechanism of bovine pancreatic phospholipase A2 by aldehyde terpenoids

被引：58

作者：

Tanaka, K

Kamatani, M

Mori, H

Fujii, S

Ikeda, K

Hisada, M

Itagaki, Y

Katsumura, S ^{[1
]}

机构：

[1] Kwansei Gakuin Univ, Sch Sci, Nishinomiya, Hyogo 6628501, Japan

[2] Osaka Univ Pharmaceut Sci, Dept Biochem, Takatsuki, Osaka 5691094, Japan

[3] Suntory Inst Bioorgan Res, Osaka 618, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 06期

关键词：

bovine pancreatic phospholipase A(2); (E)-3-methoxycarbonyl-2,4,6-trienal compounds; dihydropyridine; lysine residue;

D O I：

10.1016/S0040-4020(98)01197-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We established the stereoselective synthesis of (E)-3-methoxycarbonyl-2,4,6-trienal compound A and discovered that the compound A showed more powerful inhibitory activity toward phospholipase A(2)(PLA(2)) from bovine pancreas than manoalide which is a typical PLA(2) inhibitor. As the inhibitory mechanism of PLA(2) by A, the irreversible formation of dihydropyridine derivative resulting from the reaction of A with lysine residues in PLA(2) was proposed based on the model reactions. Furthermore, A was found to selectively modify Lys56 which is included in the interfacial recognition site of this enzyme by the MALDI-TOF-MS peptide mapping analyses. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1657 / 1686

页数：30

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[1] LUFFARIELLOLIDE, AN ANTIINFLAMMATORY SESTERTERPENE FROM THE MARINE SPONGE LUFFARIELLA SP [J].