Minnamide A, a Linear Lipopeptide from the Marine Cyanobacterium Okeania hirsuta

Shimpei Sumimoto; Masayuki Kobayashi; Rio Sato; Seiichi Shinomiya; Arihiro Iwasaki; Shoichiro Suda; Toshiaki Teruya; Toshiyasu Inuzuka; Osamu Ohno; Kiyotake Suenaga

doi:10.1021/acs.orglett.9b00135

Minnamide A, a Linear Lipopeptide from the Marine Cyanobacterium Okeania hirsuta

Shimpei Sumimoto, Masayuki Kobayashi, Rio Sato, Seiichi Shinomiya, Arihiro Iwasaki, Shoichiro Suda, Toshiaki Teruya, Toshiyasu Inuzuka, Osamu Ohno, Kiyotake Suenaga

Department of Chemistry

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

11 Citations (Scopus)

Abstract

Minnamide A is a lipopeptide with a unique repeating structure consisting of hydroxy and proposed β-branched methyl groups. The absolute configuration of minnamide A was determined by a combination of chemical degradation, chiral HPLC analyses, and synthetic methods. Minnamide A showed growth-inhibitory activity toward HeLa cells with an IC ₅₀ value of 0.17 μM and rapidly induced cell death at a concentration of 2 μM. Minnamide A induced the copper-mediated accumulation of reactive oxygen species.

Original language	English
Pages (from-to)	1187-1190
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.9b00135
Publication status	Published - 2019 Feb 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b00135

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title = "Minnamide A, a Linear Lipopeptide from the Marine Cyanobacterium Okeania hirsuta",

abstract = " Minnamide A is a lipopeptide with a unique repeating structure consisting of hydroxy and proposed β-branched methyl groups. The absolute configuration of minnamide A was determined by a combination of chemical degradation, chiral HPLC analyses, and synthetic methods. Minnamide A showed growth-inhibitory activity toward HeLa cells with an IC 50 value of 0.17 μM and rapidly induced cell death at a concentration of 2 μM. Minnamide A induced the copper-mediated accumulation of reactive oxygen species. ",

author = "Shimpei Sumimoto and Masayuki Kobayashi and Rio Sato and Seiichi Shinomiya and Arihiro Iwasaki and Shoichiro Suda and Toshiaki Teruya and Toshiyasu Inuzuka and Osamu Ohno and Kiyotake Suenaga",

note = "Funding Information: This work was supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology of Japan (16H03285 and 17H05450). We thank Kaneka Corporation for their gift of (S)-Roche ester. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b00135",

language = "English",

volume = "21",

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journal = "Organic Letters",

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T1 - Minnamide A, a Linear Lipopeptide from the Marine Cyanobacterium Okeania hirsuta

AU - Sumimoto, Shimpei

AU - Kobayashi, Masayuki

AU - Sato, Rio

AU - Shinomiya, Seiichi

AU - Iwasaki, Arihiro

AU - Suda, Shoichiro

AU - Teruya, Toshiaki

AU - Inuzuka, Toshiyasu

AU - Ohno, Osamu

AU - Suenaga, Kiyotake

N1 - Funding Information: This work was supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology of Japan (16H03285 and 17H05450). We thank Kaneka Corporation for their gift of (S)-Roche ester. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/2/15

Y1 - 2019/2/15

N2 - Minnamide A is a lipopeptide with a unique repeating structure consisting of hydroxy and proposed β-branched methyl groups. The absolute configuration of minnamide A was determined by a combination of chemical degradation, chiral HPLC analyses, and synthetic methods. Minnamide A showed growth-inhibitory activity toward HeLa cells with an IC 50 value of 0.17 μM and rapidly induced cell death at a concentration of 2 μM. Minnamide A induced the copper-mediated accumulation of reactive oxygen species.

AB - Minnamide A is a lipopeptide with a unique repeating structure consisting of hydroxy and proposed β-branched methyl groups. The absolute configuration of minnamide A was determined by a combination of chemical degradation, chiral HPLC analyses, and synthetic methods. Minnamide A showed growth-inhibitory activity toward HeLa cells with an IC 50 value of 0.17 μM and rapidly induced cell death at a concentration of 2 μM. Minnamide A induced the copper-mediated accumulation of reactive oxygen species.

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Minnamide A, a Linear Lipopeptide from the Marine Cyanobacterium Okeania hirsuta

Abstract

ASJC Scopus subject areas

UN SDGs

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