Isolation and Total Synthesis of Hoshinolactam, an Antitrypanosomal Lactam from a Marine Cyanobacterium

Hidetoshi Ogawa; Arihiro Iwasaki; Shimpei Sumimoto; Masato Iwatsuki; Aki Ishiyama; Rei Hokari; Kazuhiko Otoguro; Satoshi Omura; Kiyotake Suenaga

doi:10.1021/acs.orglett.7b00047

Isolation and Total Synthesis of Hoshinolactam, an Antitrypanosomal Lactam from a Marine Cyanobacterium

Hidetoshi Ogawa, Arihiro Iwasaki, Shimpei Sumimoto, Masato Iwatsuki, Aki Ishiyama, Rei Hokari, Kazuhiko Otoguro, Satoshi Omura, Kiyotake Suenaga

Department of Chemistry

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

29 Citations (Scopus)

Abstract

In the search for new antiprotozoal substances, hoshinolactam, an antitrypanosomal lactam, was isolated from a marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configuration was determined by the first total synthesis. Hoshinolactam showed potent antitrypanosomal activity with an IC₅₀ value of 3.9 nM without cytotoxicity against human fetal lung fibroblast MRC-5 cells (IC₅₀ > 25 μM).

Original language	English
Pages (from-to)	890-893
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.7b00047
Publication status	Published - 2017 Feb 17

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b00047

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abstract = "In the search for new antiprotozoal substances, hoshinolactam, an antitrypanosomal lactam, was isolated from a marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configuration was determined by the first total synthesis. Hoshinolactam showed potent antitrypanosomal activity with an IC50 value of 3.9 nM without cytotoxicity against human fetal lung fibroblast MRC-5 cells (IC50 > 25 μM).",

author = "Hidetoshi Ogawa and Arihiro Iwasaki and Shimpei Sumimoto and Masato Iwatsuki and Aki Ishiyama and Rei Hokari and Kazuhiko Otoguro and Satoshi Omura and Kiyotake Suenaga",

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T1 - Isolation and Total Synthesis of Hoshinolactam, an Antitrypanosomal Lactam from a Marine Cyanobacterium

AU - Ogawa, Hidetoshi

AU - Iwasaki, Arihiro

AU - Sumimoto, Shimpei

AU - Iwatsuki, Masato

AU - Ishiyama, Aki

AU - Hokari, Rei

AU - Otoguro, Kazuhiko

AU - Omura, Satoshi

AU - Suenaga, Kiyotake

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant No. 16H03285 and the Naito Foundation. Publisher Copyright: © 2017 American Chemical Society. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2017/2/17

Y1 - 2017/2/17

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AB - In the search for new antiprotozoal substances, hoshinolactam, an antitrypanosomal lactam, was isolated from a marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configuration was determined by the first total synthesis. Hoshinolactam showed potent antitrypanosomal activity with an IC50 value of 3.9 nM without cytotoxicity against human fetal lung fibroblast MRC-5 cells (IC50 > 25 μM).

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Isolation and Total Synthesis of Hoshinolactam, an Antitrypanosomal Lactam from a Marine Cyanobacterium

Abstract

ASJC Scopus subject areas

UN SDGs

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