Brevisulcatic Acids, Marine Ladder-Frame Polyethers from the Red Tide Dinoflagellate Karenia brevisulcata in New Zealand

被引：11

作者：

Suzuki, Rina ^{[1
]}

Irie, Raku ^{[1
]}

Harntaweesup, Yanit ^{[1
]}

Tachibana, Kazuo ^{[1
]}

Holland, Patrick T. ^{[2
]}

Harwood, D. Tim ^{[2
]}

Shi, Feng ^{[2
]}

Beuzenberg, Veronica ^{[2
]}

Itoh, Yoshiyuki ^{[3
]}

Pascal, Steven ^{[4
]}

Edwards, Patrick J. B. ^{[4
]}

Satake, Masayuki ^{[1
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

[2] Cawthron Inst, Nelson 7042, New Zealand

[3] JEOL Ltd, MS Business Unit, Tokyo, Japan

[4] Massey Univ, Inst Fundamental Sci, Palmerston North 4442, New Zealand

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 22期

关键词：

BREVETOXIN-A; GAMBIERDISCUS-TOXICUS; GYMNODINIUM-MIKIMOTOI; GYMNOCIN-A; CIGUATOXIN; TOXINS; NMR;

D O I：

10.1021/ol502700h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The isolation and structural determination of new marine ladder-frame polyethers, brevisulcatic acids-1 (1) and -4 (2) are reported. Brevisulcatic acids were isolated from the dinoflagellate Karenia brevisulcata, which was identified as the causative species of a major red tide event in New Zealand in 1998. The ether ring composition and a beta-hydroxy, gamma-methylene valeric acid side chain of 1 and 2 are common, but 2 has a gamma-lactone as the 5-membered A-ring while 1 is the seco acid analogue. Compound 2 has structural and bioactivity similarities to brevetoxin A.

引用

页码：5850 / 5853

页数：4

共 19 条

[1] Characterization of polar brevetoxin derivatives isolated from Karenia brevis cultures and natural blooms [J].

Abraham, Ann ;

Plakas, Steven M. ;

Wang, Zhihong ;

Jester, Edward L. E. ;

El Said, Kathleen R. ;

Granade, Hudson R. ;

Henry, Michael S. ;

Blum, Patricia C. ;

Pierce, Richard H. ;

Dickey, Robert W. .

TOXICON, 2006, 48 (01) :104-115

[2]

Chang F. H, 1999, HARMFUL ALGAE, V38, P377

[3]

Chang F.H., 1999, HARMFUL ALGAE NEWS, V19, P3

[4] THE RELATIONSHIP OF BREVETOXIN LENGTH AND A-RING FUNCTIONALITY TO BINDING AND ACTIVITY IN NEURONAL SODIUM-CHANNELS [J].

GAWLEY, RE ;

REIN, KS ;

JEGLITSCH, G ;

ADAMS, DJ ;

THEODORAKIS, EA ;

TIEBES, J ;

NICOLAOU, KC ;

BADEN, DG .

CHEMISTRY & BIOLOGY, 1995, 2 (08) :533-541

[5] Brevisulcenal-F: A Polycyclic Ether Toxin Associated with Massive Fish-kills in New Zealand [J].

Hamamoto, Yuka ;

Tachibana, Kazuo ;

Holland, Patrick T. ;

Shi, Feng ;

Beuzenberg, Veronica ;

Itoh, Yoshiyuki ;

Satake, Masayuki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (10) :4963-4968

[6] A sensitive LC-MS/MS assay for brevisulcenal and brevisulcatic acid toxins produced by the dinoflagellate Karenia brevisulcata [J].

Harwood, D. Tim ;

Shi, Feng ;

Satake, Masayuki ;

Holland, Patrick T. .

TOXICON, 2014, 84 :19-27

[7] Novel toxins produced by the dinoflagellate Karenia brevisulcata [J].

Holland, Patrick T. ;

Shi, Feng ;

Satake, Masayuki ;

Hamamoto, Yuka ;

Ito, Emiko ;

Beuzenberg, Veronica ;

McNabb, Paul ;

Munday, Rex ;

Briggs, Lyn ;

Truman, Penelope ;

Gooneratne, Ravi ;

Edwards, Patrick ;

Pascal, Steven M. .

HARMFUL ALGAE, 2012, 13 :47-57

[8]

IENAGA K, 1988, CHEM PHARM BULL, V36, P70

[9] C-13 NMR ASSIGNMENTS OF CIGUATOXIN BY INVERSE-DETECTED 2D-SPECTROSCOPY AND AN EXPLANATION OF NMR SIGNAL BROADENING [J].

MURATA, M ;

LEGRAND, AM ;

SCHEUER, PJ ;

YASUMOTO, T .

TETRAHEDRON LETTERS, 1992, 33 (04) :525-526

[10] STRUCTURES AND CONFIGURATIONS OF CIGUATOXIN FROM THE MORAY EEL GYMNOTHORAX-JAVA']JAVANICUS AND ITS LIKELY PRECURSOR FROM THE DINOFLAGELLATE GAMBIERDISCUS-TOXICUS [J].

MURATA, M ;

LEGRAND, AM ;

ISHIBASHI, Y ;

FUKUI, M ;

YASUMOTO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4380-4386

← 1 2 →