Synthesis of a new phospholipase A2 inhibitor of an aldehyde terpenoid and its possible inhibitory mechanism

被引：45

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 662, Japan

[2] Osaka Univ Pharmaceut Sci, Dept Biochem, Takatsuki, Osaka 56911, Japan

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(97)10805-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-(E)-Methoxycarbonyl-2,4,6-trienal compound A was stereoselectively synthesized and found to show strong inhibitory activity toward phospholipase A(2) (PLA(2)) from bovine pancreas. As the inhibitory mechanism of PLA(2) by A, the irreversible formation of dihydropyridine resulting from the reaction of A with lysine residues in PLA(2) is proposed based on the model reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1185 / 1188

页数：4

相关论文

共 17 条

[1] CORRELATION OF THE REACTIVITY OF 1,4-DIALDEHYDES WITH METHYLAMINE IN BIOMIMETIC CONDITIONS TO THEIR HOT TASTE - COVALENT BINDING TO PRIMARY AMINES AS A MOLECULAR MECHANISM IN HOT TASTE RECEPTORS [J].

CIMINO, G ;

SODANO, G ;

SPINELLA, A .

TETRAHEDRON, 1987, 43 (22) :5401-5410

[2]

de Silva E.D., 1980, TETRAHEDRON LETT, V21, P1611, DOI [10.1016/S0040-4039(00)77766-5, DOI 10.1016/S0040-4039(00)77766-5]

[3] 2-STEP INACTIVATION OF BEE VENOM PHOSPHOLIPASE-A2 BY SCALARADIAL [J].

DECARVALHO, MS ;

JACOBS, RS .

BIOCHEMICAL PHARMACOLOGY, 1991, 42 (08) :1621-1626

[4]

Dennis E.A., 1983, The Enzymes, P307

[5] CHEMICAL MODIFICATION AND INACTIVATION OF PHOSPHOLIPASES A(2) BY A MANOALIDE ANALOG [J].

FUJII, S ;

TAHARA, Y ;

TOYOMOTO, M ;

HADA, S ;

NISHIMURA, H ;

INOUE, S ;

IKEDA, K ;

INAGAKI, Y ;

KATSUMURA, S ;

SAMEJIMA, Y ;

OMORISATOH, T ;

TAKASAKI, C ;

HAYASHI, K .

BIOCHEMICAL JOURNAL, 1995, 308 :297-304

[6] REGIOSPECIFIC SYNTHESIS OF GAMMA-HYDROXYBUTENOLIDE - PHOTOSENSITIZED OXYGENATION OF SUBSTITUTED 2-TRIMETHYLSILYLFURAN [J].

KATSUMURA, S ;

HORI, K ;

FUJIWARA, S ;

ISOE, S .

TETRAHEDRON LETTERS, 1985, 26 (38) :4625-4628

[7] TOWARD ELUCIDATION OF THE INHIBITION-MECHANISM OF PHOSPHOLIPASE-A2 BY MANOALIDE - SELECTIVELY MODIFIED AMINO-ACID-RESIDUES BY MANOALIDE ANALOGS [J].

KATSUMURA, S ;

HAN, Q ;

FUJIWARA, S ;

ISOE, S ;

NISHIMURA, H ;

INOUE, S ;

IKEDA, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (10) :1267-1268

[8] PHOSPHOLIPASE-A2 INHIBITION BY MANOALIDE - DEVELOPMENT OF SIMPLE ANALOGS AND NECESSARY FUNCTIONAL-GROUPS FOR INHIBITION [J].

KATSUMURA, S ;

HAN, Q ;

KADONO, H ;

FUJIWARA, S ;

ISOE, S ;

FUJII, S ;

NISHIMURA, H ;

IKEDA, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (10) :1263-1266

[9] A TOTAL SYNTHESIS OF (+/-)-ZOAPATANOL AND DEMETHYL-ORF13811 [J].

KOCIENSKI, PJ ;

LOVE, CJ ;

WHITBY, RJ ;

COSTELLO, G ;

ROBERTS, DA .

TETRAHEDRON, 1989, 45 (12) :3839-3848

[10] 6-PI-ELECTROCYCLIZATION OF 1-AZATRIENES TO 1,2-DIHYDROPYRIDINES [J].

MAYNARD, DF ;

OKAMURA, WH .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1763-1771