Isolation of three marine prostanoids, possible biosynthetic intermediates for clavulones, from the okinawan soft coral Clavularia viridis

被引：0

作者：

Watanabe, K ^{[1
]}

Sekine, M ^{[1
]}

Iguchi, K ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Life Sci, Tokyo 1920392, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2003年 / 51卷 / 08期

关键词：

soft coral; Clavularia viridis; marine prostanoid; biosynthesis; preclavulone-A methyl ester;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three marine prostanoids, 1, 2, and 3, were isolated from the extract of the Okinawan soft coral Clavularia viridis. The structures of these compounds were assigned based on the results of spectroscopic analysis. Compound 1 was shown to be preclavulone-A methyl ester, and this is the first isolation of the ester of preclavulone-A as a natural product. Preclavulone-A is proposed to be the key intermediate in the biosynthesis of marine prostanoids exemplified by clavulones in C. viridis. The new prostanoid 3 was suggested to be a biosynthetic intermediate from preclavulone-A to clavulones, and a possible biogenetic pathway via 3 is proposed.

引用

页码：909 / 913

页数：5

共 20 条

[1]

Agalias A, 2000, Z NATURFORSCH C, V55, P425

[2] ANTIVIRAL ACTIVITY OF THE PROSTANOID CLAVULONE-II AGAINST VESICULAR STOMATITIS-VIRUS [J].

BADER, T ;

YAMADA, Y ;

ANKEL, H .

ANTIVIRAL RESEARCH, 1991, 16 (04) :341-355

[3] IDENTIFICATION OF A NEW EICOSANOID FROM INVITRO BIOSYNTHETIC EXPERIMENTS WITH CLAVULARIA-VIRIDIS - IMPLICATIONS FOR THE BIOSYNTHESIS OF CLAVULONES [J].

COREY, EJ ;

LANSBURY, PT ;

YAMADA, Y .

TETRAHEDRON LETTERS, 1985, 26 (35) :4171-4174

[4] INTERMEDIACY OF 8-(R)-HPETE IN THE CONVERSION OF ARACHIDONIC-ACID TO PRE-CLAVULONE-A BY CLAVULARIA-VIRIDIS - IMPLICATIONS FOR THE BIOSYNTHESIS OF MARINE PROSTANOIDS [J].

COREY, EJ ;

DALARCAO, M ;

MATSUDA, SPT ;

LANSBURY, PT ;

YAMADA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) :289-290

[5] GENERALITY OF MARINE PROSTANOID BIOSYNTHESIS BY THE 2-OXIDOPENTADIENYL CATION PATHWAY [J].

COREY, EJ ;

MATSUDA, SPT .

TETRAHEDRON LETTERS, 1987, 28 (37) :4247-4250

[6] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-PRECLAVULONE-A [J].

COREY, EJ ;

XIANG, YB .

TETRAHEDRON LETTERS, 1988, 29 (09) :995-998

[7] BIOSYNTHESIS OF 8-R-HPETE AND PRECLAVULONE-A FROM ARACHIDONATE IN SEVERAL SPECIES OF CARIBBEAN CORAL - A WIDESPREAD ROUTE TO MARINE PROSTANOIDS [J].

COREY, EJ ;

MATSUDA, SPT ;

NAGATA, R ;

CLEAVER, MB .

TETRAHEDRON LETTERS, 1988, 29 (21) :2555-2558

[8]

HONDA A, 1987, MOL PHARMACOL, V32, P530

[9] ANTILEUKEMIC EFFECT OF CORAL-PROSTANOIDS CLAVULONES FROM THE STOLONIFER CLAVULARIA-VIRIDIS ON HUMAN MYELOID-LEUKEMIA (HL-60) CELLS [J].

HONDA, A ;

YAMAMOTO, Y ;

MORI, Y ;

YAMADA, Y ;

KIKUCHI, H .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1985, 130 (02) :515-523

[10] New marine prostanoids from the Okinawan soft coral, Clavularia viridis [J].

Iwashima, M ;

Okamoto, K ;

Konno, F ;

Iguchi, K .

JOURNAL OF NATURAL PRODUCTS, 1999, 62 (02) :352-354

← 1 2 →