Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities

Nagy Morsy; Toshihiro Houdai; Shigeru Matsuoka; Nobuaki Matsumori; Seiji Adachi; Tohru Oishi; Michio Murata; Takashi Iwashita; Tsuyoshi Fujita

doi:10.1016/j.bmc.2006.06.012

Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities

Nagy Morsy, Toshihiro Houdai, Shigeru Matsuoka, Nobuaki Matsumori, Seiji Adachi, Tohru Oishi, Michio Murata, Takashi Iwashita, Tsuyoshi Fujita

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72 Citations (Scopus)

Abstract

Two new homologues of amphidinols (AM14 and AM15) were isolated from the cultured dinoflagellate Amphidinium klebsii. The structures were elucidated on the basis of 2D NMR and collision-induced dissociation MS/MS and turned out to be closely related homologues of AM7. Their weak membrane-disrupting activity indicates that the hydrophobic polyene chain is essential for the potent biological activities. Structure-activity relationship for the polyhydroxyl part was then examined with use of AM homologues possessing various chain lengths, indicating that the pore size of the channel/lesion formed by AMs was not greatly affected by the length of the polyhydroxyl chain.

Original language	English
Pages (from-to)	6548-6554
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	19
DOIs	https://doi.org/10.1016/j.bmc.2006.06.012
Publication status	Published - Oct 1 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2006.06.012

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title = "Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities",

abstract = "Two new homologues of amphidinols (AM14 and AM15) were isolated from the cultured dinoflagellate Amphidinium klebsii. The structures were elucidated on the basis of 2D NMR and collision-induced dissociation MS/MS and turned out to be closely related homologues of AM7. Their weak membrane-disrupting activity indicates that the hydrophobic polyene chain is essential for the potent biological activities. Structure-activity relationship for the polyhydroxyl part was then examined with use of AM homologues possessing various chain lengths, indicating that the pore size of the channel/lesion formed by AMs was not greatly affected by the length of the polyhydroxyl chain.",

author = "Nagy Morsy and Toshihiro Houdai and Shigeru Matsuoka and Nobuaki Matsumori and Seiji Adachi and Tohru Oishi and Michio Murata and Takashi Iwashita and Tsuyoshi Fujita",

note = "Funding Information: We are grateful to Prof. Shoichi Kusumoto, Suntory Institute for Bioorganic Research, for encouragement and discussion, and to Prof. Masayuki Satake for valuable information. This study was supported by Grants-in-Aid from MEXT Japan (Scientific Research (A) No. 15201048 and Priority Area (A) No. 16073211), and by Yamada Science Foundation. S.M. and T.H. among the authors have been supported by 21 century COE program {\textquoteleft}Creation of Integrated Ecochemistry{\textquoteright}.",

year = "2006",

month = oct,

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doi = "10.1016/j.bmc.2006.06.012",

language = "English",

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TY - JOUR

T1 - Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities

AU - Morsy, Nagy

AU - Houdai, Toshihiro

AU - Matsuoka, Shigeru

AU - Matsumori, Nobuaki

AU - Adachi, Seiji

AU - Oishi, Tohru

AU - Murata, Michio

AU - Iwashita, Takashi

AU - Fujita, Tsuyoshi

N1 - Funding Information: We are grateful to Prof. Shoichi Kusumoto, Suntory Institute for Bioorganic Research, for encouragement and discussion, and to Prof. Masayuki Satake for valuable information. This study was supported by Grants-in-Aid from MEXT Japan (Scientific Research (A) No. 15201048 and Priority Area (A) No. 16073211), and by Yamada Science Foundation. S.M. and T.H. among the authors have been supported by 21 century COE program ‘Creation of Integrated Ecochemistry’.

PY - 2006/10/1

Y1 - 2006/10/1

N2 - Two new homologues of amphidinols (AM14 and AM15) were isolated from the cultured dinoflagellate Amphidinium klebsii. The structures were elucidated on the basis of 2D NMR and collision-induced dissociation MS/MS and turned out to be closely related homologues of AM7. Their weak membrane-disrupting activity indicates that the hydrophobic polyene chain is essential for the potent biological activities. Structure-activity relationship for the polyhydroxyl part was then examined with use of AM homologues possessing various chain lengths, indicating that the pore size of the channel/lesion formed by AMs was not greatly affected by the length of the polyhydroxyl chain.

AB - Two new homologues of amphidinols (AM14 and AM15) were isolated from the cultured dinoflagellate Amphidinium klebsii. The structures were elucidated on the basis of 2D NMR and collision-induced dissociation MS/MS and turned out to be closely related homologues of AM7. Their weak membrane-disrupting activity indicates that the hydrophobic polyene chain is essential for the potent biological activities. Structure-activity relationship for the polyhydroxyl part was then examined with use of AM homologues possessing various chain lengths, indicating that the pore size of the channel/lesion formed by AMs was not greatly affected by the length of the polyhydroxyl chain.

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JO - Bioorganic and Medicinal Chemistry

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IS - 19

ER -

Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities

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