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

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

Research output: Contribution to journalArticle

17 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 IC50 value of 26.3 nM.

Original languageEnglish
Pages (from-to)5472-5478
Number of pages7
JournalTetrahedron
Volume72
Issue number35
DOIs
Publication statusPublished - 2016 Sep 1

Fingerprint

Depsipeptides
Stereochemistry
Bioassay
Cyanobacteria
Cytotoxicity
Fractionation
Uterine Cervical Neoplasms
Biological Assay
Inhibitory Concentration 50
High Pressure Liquid Chromatography
Cells
Nuclear magnetic resonance
Degradation

Keywords

  • Cyclic depsipeptide
  • Cytotoxicity
  • Marine natural products
  • Okeania

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Sueyoshi, K., Kaneda, M., Sumimoto, S., Oishi, S., Fujii, N., Suenaga, K., & Teruya, T. (2016). Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp. Tetrahedron, 72(35), 5472-5478. https://doi.org/10.1016/j.tet.2016.07.031

Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp. / Sueyoshi, Kosuke; Kaneda, Masato; Sumimoto, Shinpei; Oishi, Shinya; Fujii, Nobutaka; Suenaga, Kiyotake; Teruya, Toshiaki.

In: Tetrahedron, Vol. 72, No. 35, 01.09.2016, p. 5472-5478.

Research output: Contribution to journalArticle

Sueyoshi, K, Kaneda, M, Sumimoto, S, Oishi, S, Fujii, N, Suenaga, K & Teruya, T 2016, 'Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp.', Tetrahedron, vol. 72, no. 35, pp. 5472-5478. https://doi.org/10.1016/j.tet.2016.07.031
Sueyoshi, Kosuke ; Kaneda, Masato ; Sumimoto, Shinpei ; Oishi, Shinya ; Fujii, Nobutaka ; Suenaga, Kiyotake ; Teruya, Toshiaki. / Odoamide, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Okeania sp. In: Tetrahedron. 2016 ; Vol. 72, No. 35. pp. 5472-5478.
@article{cabf02674e264a81bc0e15a79055449e,
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 IC50 value 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",
year = "2016",
month = "9",
day = "1",
doi = "10.1016/j.tet.2016.07.031",
language = "English",
volume = "72",
pages = "5472--5478",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "35",

}

TY - JOUR

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

PY - 2016/9/1

Y1 - 2016/9/1

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 IC50 value 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 IC50 value of 26.3 nM.

KW - Cyclic depsipeptide

KW - Cytotoxicity

KW - Marine natural products

KW - Okeania

UR - http://www.scopus.com/inward/record.url?scp=84979917087&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84979917087&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2016.07.031

DO - 10.1016/j.tet.2016.07.031

M3 - Article

AN - SCOPUS:84979917087

VL - 72

SP - 5472

EP - 5478

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 35

ER -