Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata

Noboru Takada; Naoyoshi Umemura; Kiyotake Suenaga; Tong Chou; Akito Nagatsu; Takeharu Haino; Kaoru Yamada; Daisuke Uemura

doi:10.1016/S0040-4039(01)00480-4

Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata

Noboru Takada, Naoyoshi Umemura, Kiyotake Suenaga, Tong Chou, Akito Nagatsu, Takeharu Haino, Kaoru Yamada, Daisuke Uemura

Research output: Contribution to journal › Article › peer-review

114 Citations (Scopus)

Abstract

Pinnatoxins B and C, the most toxic components in the pinnatoxin series, were successfully purified from the Okinawan bivalve Pinna muricata. Their gross structures were determined based on NMR and MS/MS spectral analyses. Their stereostructures were mainly determined by transformation reactions. Pinnatoxins B and C, C-34 epimers of each other, have an amphoteric macrocycle composed of 6,7-spiro, 5,6-bicyclo and 6,5,6-trispiro ketal rings, the same as in pinnatoxins A and D.

Original language	English
Pages (from-to)	3491-3494
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4039(01)00480-4
Publication status	Published - 2001 May 14
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata. / Takada, Noboru; Umemura, Naoyoshi; Suenaga, Kiyotake; Chou, Tong; Nagatsu, Akito; Haino, Takeharu; Yamada, Kaoru; Uemura, Daisuke.

In: Tetrahedron Letters, Vol. 42, No. 20, 14.05.2001, p. 3491-3494.

Research output: Contribution to journal › Article › peer-review

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title = "Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata",

abstract = "Pinnatoxins B and C, the most toxic components in the pinnatoxin series, were successfully purified from the Okinawan bivalve Pinna muricata. Their gross structures were determined based on NMR and MS/MS spectral analyses. Their stereostructures were mainly determined by transformation reactions. Pinnatoxins B and C, C-34 epimers of each other, have an amphoteric macrocycle composed of 6,7-spiro, 5,6-bicyclo and 6,5,6-trispiro ketal rings, the same as in pinnatoxins A and D.",

author = "Noboru Takada and Naoyoshi Umemura and Kiyotake Suenaga and Tong Chou and Akito Nagatsu and Takeharu Haino and Kaoru Yamada and Daisuke Uemura",

note = "Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (No. 11558079) and Scientific Research on Priority Areas (A) (No. 12045235) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We are indebted to Wako Pure Chemical Industries Ltd., and Banyu Pharmaceutical Co., Ltd. for their financial support. We thank Professors R. Noyori and M. Kitamura (COE, Nagoya University) for performing the NMR experiments. ",

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AU - Suenaga, Kiyotake

AU - Chou, Tong

AU - Nagatsu, Akito

AU - Haino, Takeharu

AU - Yamada, Kaoru

AU - Uemura, Daisuke

N1 - Funding Information: This work was supported in part by Grants-in-Aid for Scientific Research (No. 11558079) and Scientific Research on Priority Areas (A) (No. 12045235) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. We are indebted to Wako Pure Chemical Industries Ltd., and Banyu Pharmaceutical Co., Ltd. for their financial support. We thank Professors R. Noyori and M. Kitamura (COE, Nagoya University) for performing the NMR experiments.

PY - 2001/5/14

Y1 - 2001/5/14

N2 - Pinnatoxins B and C, the most toxic components in the pinnatoxin series, were successfully purified from the Okinawan bivalve Pinna muricata. Their gross structures were determined based on NMR and MS/MS spectral analyses. Their stereostructures were mainly determined by transformation reactions. Pinnatoxins B and C, C-34 epimers of each other, have an amphoteric macrocycle composed of 6,7-spiro, 5,6-bicyclo and 6,5,6-trispiro ketal rings, the same as in pinnatoxins A and D.

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Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata

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