Isolation of Hennaminal and Isolation and Total Synthesis of Hennamide, Pyrrolinone Compounds from the Marine Cyanobacterium Rivularia sp.

Hiroki Takahashi; Arihiro Iwasaki; Akira Ebihara; Raimu Taguchi; Ghulam Jeelani; Tomoyoshi Nozaki; Kiyotake Suenaga

doi:10.1021/acs.orglett.3c00421

Isolation of Hennaminal and Isolation and Total Synthesis of Hennamide, Pyrrolinone Compounds from the Marine Cyanobacterium Rivularia sp.

Hiroki Takahashi, Arihiro Iwasaki, Akira Ebihara, Raimu Taguchi, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

Department of Chemistry

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

Abstract

Two new natural products were isolated from the marine cyanobacterium Rivularia sp. collected in Japan. Hennaminal possesses a very rare functional group, β,β-diamino unsaturated ketone, which has only been found in bohemamine-type natural products so far. Hennamide possesses a reactive N-acyl pyrrolinone moiety, which induces self-dimerization. The isolation and structure determination supported by computational chemistry and total synthesis, as well as the antitrypanosomal activities of hennaminal and hennamide are described.

Original language	English
Pages (from-to)	2400-2404
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.3c00421
Publication status	Published - 2023 Apr 14

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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10.1021/acs.orglett.3c00421

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title = "Isolation of Hennaminal and Isolation and Total Synthesis of Hennamide, Pyrrolinone Compounds from the Marine Cyanobacterium Rivularia sp.",

abstract = "Two new natural products were isolated from the marine cyanobacterium Rivularia sp. collected in Japan. Hennaminal possesses a very rare functional group, β,β-diamino unsaturated ketone, which has only been found in bohemamine-type natural products so far. Hennamide possesses a reactive N-acyl pyrrolinone moiety, which induces self-dimerization. The isolation and structure determination supported by computational chemistry and total synthesis, as well as the antitrypanosomal activities of hennaminal and hennamide are described.",

author = "Hiroki Takahashi and Arihiro Iwasaki and Akira Ebihara and Raimu Taguchi and Ghulam Jeelani and Tomoyoshi Nozaki and Kiyotake Suenaga",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant No. 20H02870, Keio Gijuku Academic Development Funds, and The Okawa Foundation for Information and Telecommunications. Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

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doi = "10.1021/acs.orglett.3c00421",

language = "English",

volume = "25",

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journal = "Organic Letters",

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T1 - Isolation of Hennaminal and Isolation and Total Synthesis of Hennamide, Pyrrolinone Compounds from the Marine Cyanobacterium Rivularia sp.

AU - Takahashi, Hiroki

AU - Iwasaki, Arihiro

AU - Ebihara, Akira

AU - Taguchi, Raimu

AU - Jeelani, Ghulam

AU - Nozaki, Tomoyoshi

AU - Suenaga, Kiyotake

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant No. 20H02870, Keio Gijuku Academic Development Funds, and The Okawa Foundation for Information and Telecommunications. Publisher Copyright: © 2023 American Chemical Society.

PY - 2023/4/14

Y1 - 2023/4/14

N2 - Two new natural products were isolated from the marine cyanobacterium Rivularia sp. collected in Japan. Hennaminal possesses a very rare functional group, β,β-diamino unsaturated ketone, which has only been found in bohemamine-type natural products so far. Hennamide possesses a reactive N-acyl pyrrolinone moiety, which induces self-dimerization. The isolation and structure determination supported by computational chemistry and total synthesis, as well as the antitrypanosomal activities of hennaminal and hennamide are described.

AB - Two new natural products were isolated from the marine cyanobacterium Rivularia sp. collected in Japan. Hennaminal possesses a very rare functional group, β,β-diamino unsaturated ketone, which has only been found in bohemamine-type natural products so far. Hennamide possesses a reactive N-acyl pyrrolinone moiety, which induces self-dimerization. The isolation and structure determination supported by computational chemistry and total synthesis, as well as the antitrypanosomal activities of hennaminal and hennamide are described.

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Isolation of Hennaminal and Isolation and Total Synthesis of Hennamide, Pyrrolinone Compounds from the Marine Cyanobacterium Rivularia sp.

Abstract

ASJC Scopus subject areas

UN SDGs

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