Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.

Kosuke Sueyoshi; Masato Kaneda; Shinpei Sumimoto; Shinya Oishi; Nobutaka Fujii; Kiyotake Suenaga; Toshiaki Teruya

doi:10.1016/j.tet.2016.07.031

Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.

Kosuke Sueyoshi, Masato Kaneda, Shinpei Sumimoto, Shinya Oishi, Nobutaka Fujii, Kiyotake Suenaga, Toshiaki Teruya

Department of Chemistry

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

30 Citations (Scopus)

Abstract

The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the 26-membered cyclodepsipeptide odoamide (1). The gross structure of 1 was determined by 1D and 2D NMR analyses, whereas its absolute stereochemistry was determined using a variety of different methods, including synthesis and chemical degradation followed by chiral HPLC analysis. Notably, odoamide (1) showed potent cytotoxicity against HeLa S3 human cervical cancer cells with an IC₅₀value of 26.3 nM.

Original language	English
Pages (from-to)	5472-5478
Number of pages	7
Journal	Tetrahedron
Volume	72
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2016.07.031
Publication status	Published - 2016

Keywords

Cyclic depsipeptide
Cytotoxicity
Marine natural products
Okeania

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tet.2016.07.031

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title = "Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.",

abstract = "The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the 26-membered cyclodepsipeptide odoamide (1). The gross structure of 1 was determined by 1D and 2D NMR analyses, whereas its absolute stereochemistry was determined using a variety of different methods, including synthesis and chemical degradation followed by chiral HPLC analysis. Notably, odoamide (1) showed potent cytotoxicity against HeLa S3 human cervical cancer cells with an IC50value of 26.3 nM.",

keywords = "Cyclic depsipeptide, Cytotoxicity, Marine natural products, Okeania",

author = "Kosuke Sueyoshi and Masato Kaneda and Shinpei Sumimoto and Shinya Oishi and Nobutaka Fujii and Kiyotake Suenaga and Toshiaki Teruya",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Young Scientists (B) ( 21710237 ) from the Ministry of Education, Culture, Sports, Science and Technology, Japan ; University of the Ryukyus Strategic Research Grant ; and Takeda Science Foundation . M.K. is grateful for Japan Society for the Promotion of Science Research Fellowships for Young Scientists ( 15J05499 ). Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

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language = "English",

volume = "72",

pages = "5472--5478",

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T1 - Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.

AU - Sueyoshi, Kosuke

AU - Kaneda, Masato

AU - Sumimoto, Shinpei

AU - Oishi, Shinya

AU - Fujii, Nobutaka

AU - Suenaga, Kiyotake

AU - Teruya, Toshiaki

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Young Scientists (B) ( 21710237 ) from the Ministry of Education, Culture, Sports, Science and Technology, Japan ; University of the Ryukyus Strategic Research Grant ; and Takeda Science Foundation . M.K. is grateful for Japan Society for the Promotion of Science Research Fellowships for Young Scientists ( 15J05499 ). Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the 26-membered cyclodepsipeptide odoamide (1). The gross structure of 1 was determined by 1D and 2D NMR analyses, whereas its absolute stereochemistry was determined using a variety of different methods, including synthesis and chemical degradation followed by chiral HPLC analysis. Notably, odoamide (1) showed potent cytotoxicity against HeLa S3 human cervical cancer cells with an IC50value of 26.3 nM.

AB - The bioassay-guided fractionation of the Okinawan marine cyanobacterium Okeania sp. led to the isolation of the 26-membered cyclodepsipeptide odoamide (1). The gross structure of 1 was determined by 1D and 2D NMR analyses, whereas its absolute stereochemistry was determined using a variety of different methods, including synthesis and chemical degradation followed by chiral HPLC analysis. Notably, odoamide (1) showed potent cytotoxicity against HeLa S3 human cervical cancer cells with an IC50value of 26.3 nM.

KW - Cyclic depsipeptide

KW - Cytotoxicity

KW - Marine natural products

KW - Okeania

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DO - 10.1016/j.tet.2016.07.031

M3 - Article

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SN - 0040-4020

VL - 72

SP - 5472

EP - 5478

JO - Tetrahedron

JF - Tetrahedron

IS - 35

ER -

Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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