Symbiodinolide, a novel polyol macrolide that activates N-type Ca2+ channel, from the symbiotic marine dinoflagellate Symbiodinium sp.

被引：56

作者：

Kita, Masaki ^{[2
]}

Ohishi, Nao ^{[1
]}

Konishi, Kaori ^{[1
]}

Kondo, Mikiko ^{[1
]}

Koyama, Tomoyuki ^{[1
]}

Kitamura, Makoto ^{[1
]}

Yamada, Kaoru ^{[1
]}

Uemura, Daisuke ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Sci, Dept Chem, Nagoya, Aichi 4648602, Japan

[2] Nagoya Univ, Grad Sch Sci, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan

来源：

TETRAHEDRON | 2007年 / 63卷 / 27期

关键词：

symbiodinolide; super-carbon-chain compounds; isolation and structure; N-type Ca2+ channel activator;

D O I：

10.1016/j.tet.2007.02.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 62-membered novel polyol macrolide with a molecular weight of 2859 mu, symbiodinolide, was isolated from the symbiotic dinoflagellate Symbiodinium sp. Symbiodinolide exhibited a potent voltage-dependent N-type Ca2+ channel-opening activity at 7 nM and immediately ruptured the tissue surface of the acoel flatworm Amphiscolops sp. at 2.5 mu M. The planar structure of symbiodinolide was elucidated by spectroscopic analysis and chemical degradations including hydrolysis and ethenolysis using the second-generation Grubbs' catalyst. Symbiodinolide was found to be a structural congener of zooxanthellatoxins. The relative stereochemistries of C26-C32, C44-C51, and C64-C66 parts, and the absolute stereochemistries of C69-73, C83-C103, and C30-C180 parts in symbiodinolide were established. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6241 / 6251

页数：11

共 43 条

[21] Synthesis and absolute configuration of an exomethylene portion of zooxanthellatoxin-A [J].

Nakamura, H ;

Takahashi, M ;

Murai, A .

TETRAHEDRON-ASYMMETRY, 1998, 9 (15) :2571-2574

[22] ZOOXANTHELLATOXIN-A, A POTENT VASOCONSTRICTIVE 62-MEMBERED LACTONE FROM A SYMBIOTIC DINOFLAGELLATE [J].

NAKAMURA, H ;

ASARI, T ;

MURAI, A ;

KAN, Y ;

KONDO, T ;

YOSHIDA, K ;

OHIZUMI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :550-551

[23] ZOOXANTHELLATOXIN-B, VASOCONSTRICTIVE CONGENER OF ZOOXANTHELLATOXIN-A FROM A SYMBIOTIC DINOFLAGELLATE SYMBIODINIUM SP [J].

NAKAMURA, H ;

ASARI, T ;

FUJIMAKI, K ;

MARUYAMA, K ;

MURAI, A ;

OHIZUMI, Y ;

KAN, Y .

TETRAHEDRON LETTERS, 1995, 36 (40) :7255-7258

[24] Absolute configuration of the spiroacetal portion of zooxanthellatoxin-A. [J].

Nakamura, H ;

Sato, K ;

Murai, A .

TETRAHEDRON LETTERS, 1996, 37 (40) :7267-7270

[25] Synthetic studies on the common C25 long chain acid portion of zooxanthellatoxins from a symbiotic dinoflagellate Symbiodinium sp. [J].

Nakamura, H ;

Fujimaki, K ;

Murai, A .

TETRAHEDRON LETTERS, 1996, 37 (18) :3153-3156

[26] Absolute configuration of the common terminal acid portion of zooxanthellatoxins from a symbiotic dinoflagellate Symbiodinium sp established by the synthesis of its ozonolysis product [J].

Nakamura, H ;

Maruyama, K ;

Fujimaki, K ;

Murai, A .

TETRAHEDRON LETTERS, 2000, 41 (12) :1927-1930

[27] STRUCTURE OF PERIODATE-OXIDATION PRODUCTS WITH CHARACTERISTIC PARTIAL STRUCTURES OF ZOOXANTHELLATOXIN-A, A POTENT VASOCONSTRICTIVE POLYOL FROM A SYMBIOTIC DINOFLAGELLATE [J].

NAKAMURA, H ;

ASARI, T ;

MURAI, A ;

KONDO, T ;

YOSHIDA, K ;

OHIZUMI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02) :313-314

[28] Zooxanthellamide Cs:: Vasoconstrictive polyhydroxylated Macrolides with the largest lactone ring size from a marine dinoflagellate of Symbiodinium sp. [J].

Onodera, K ;

Nakamura, H ;

Oba, Y ;

Ohizumi, Y ;

Ojika, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10406-10411

[29] Zooxanthellamide A, a novel polyhydroxy metabolite from a marine dinoflagellate of Symbiodinium sp. [J].

Onodera, K ;

Nakamura, H ;

Oba, Y ;

Ojika, M .

TETRAHEDRON, 2003, 59 (07) :1067-1071

[30] Zooxanthellamide B, a novel large polyhydroxy metabolite from a marine dinoflagellate of Symbiodinium sp. [J].

Onodera, KI ;

Nakamura, H ;

Oba, Y ;

Ojika, M .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2004, 68 (04) :955-958

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