Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata

Kaori Ozaki; Arihiro Iwasaki; Kiyotake Suenaga; Toshiaki Teruya

doi:10.1016/j.tet.2019.04.046

Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata

Kaori Ozaki, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

Department of Chemistry

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

5 Citations (Scopus)

Abstract

Kyanamide (1), a new depsipeptide containing 3-amino-6-hydroxy-2-piperidone moiety, was isolated from the Caldora penicillata marine cyanobacterium collected in Okinawa. Its structure was determined by spectroscopic analysis and Marfey's analysis of acid hydrolysate. Kyanamide exhibited moderate cytotoxicity against HeLa S3 cells. 1 also exhibited potent protease inhibitory activity against elastase and chymotrypsin with IC₅₀ values of 0.13 nM and 1.1 μM.

Original language	English
Pages (from-to)	3382-3386
Number of pages	5
Journal	Tetrahedron
Volume	75
Issue number	25
DOIs	https://doi.org/10.1016/j.tet.2019.04.046
Publication status	Published - 2019 Jun 21

Keywords

Caldora penicillata
Cyclic depsipeptide
Marine natural products
Serine protease inhibition

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.2019.04.046

Cite this

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title = "Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata",

abstract = "Kyanamide (1), a new depsipeptide containing 3-amino-6-hydroxy-2-piperidone moiety, was isolated from the Caldora penicillata marine cyanobacterium collected in Okinawa. Its structure was determined by spectroscopic analysis and Marfey's analysis of acid hydrolysate. Kyanamide exhibited moderate cytotoxicity against HeLa S3 cells. 1 also exhibited potent protease inhibitory activity against elastase and chymotrypsin with IC50 values of 0.13 nM and 1.1 μM.",

keywords = "Caldora penicillata, Cyclic depsipeptide, Marine natural products, Serine protease inhibition",

author = "Kaori Ozaki and Arihiro Iwasaki and Kiyotake Suenaga and Toshiaki Teruya",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Numbers 15K01803 ; University of the Ryukyus Strategic Research Grant . Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2019",

month = jun,

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doi = "10.1016/j.tet.2019.04.046",

language = "English",

volume = "75",

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T1 - Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata

AU - Ozaki, Kaori

AU - Iwasaki, Arihiro

AU - Suenaga, Kiyotake

AU - Teruya, Toshiaki

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Numbers 15K01803 ; University of the Ryukyus Strategic Research Grant . Publisher Copyright: © 2019 Elsevier Ltd Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

PY - 2019/6/21

Y1 - 2019/6/21

N2 - Kyanamide (1), a new depsipeptide containing 3-amino-6-hydroxy-2-piperidone moiety, was isolated from the Caldora penicillata marine cyanobacterium collected in Okinawa. Its structure was determined by spectroscopic analysis and Marfey's analysis of acid hydrolysate. Kyanamide exhibited moderate cytotoxicity against HeLa S3 cells. 1 also exhibited potent protease inhibitory activity against elastase and chymotrypsin with IC50 values of 0.13 nM and 1.1 μM.

AB - Kyanamide (1), a new depsipeptide containing 3-amino-6-hydroxy-2-piperidone moiety, was isolated from the Caldora penicillata marine cyanobacterium collected in Okinawa. Its structure was determined by spectroscopic analysis and Marfey's analysis of acid hydrolysate. Kyanamide exhibited moderate cytotoxicity against HeLa S3 cells. 1 also exhibited potent protease inhibitory activity against elastase and chymotrypsin with IC50 values of 0.13 nM and 1.1 μM.

KW - Caldora penicillata

KW - Cyclic depsipeptide

KW - Marine natural products

KW - Serine protease inhibition

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Kyanamide, a new Ahp-containing depsipeptide from marine cyanobacterium Caldora penicillata

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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