Ma'edamines E and F, rare bromotyrosine alkaloids possessing a 1,2,3,5-tetrasubstituted pyridinium moiety from an Okinawan marine sponge Suberea sp.

Shin ichiro Kurimoto; Ayano Okamoto; Satsuki Seino; Jane Fromont; Jun'ichi Kobayashi; Takaaki Kubota

doi:10.1016/j.tetlet.2022.153985

Ma'edamines E and F, rare bromotyrosine alkaloids possessing a 1,2,3,5-tetrasubstituted pyridinium moiety from an Okinawan marine sponge Suberea sp.

Shin ichiro Kurimoto, Ayano Okamoto, Satsuki Seino, Jane Fromont, Jun'ichi Kobayashi, Takaaki Kubota

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

Abstract

Two new bromotyrosine alkaloids, ma'edamines E (1) and F (2), were isolated from an Okinawan marine sponge Suberea sp., and their structures were elucidated by the analyses of spectroscopic (UV, IR, and NMR) and spectrometric (MS) data. Ma'edamines E (1) and F (2) are the second and third examples of natural products possessing an N-alkyl-3,5-diethyl-2-propylpyridinium moiety. Ma'edamine F (2) is the first bromotyrosine alkaloid having both pyridinium and quaternary ammonium moieties. Ma'edamines E (1) and F (2) showed moderate cytotoxicity against L1210 murine leukemia cells in vitro.

Original language	English
Article number	153985
Journal	Tetrahedron Letters
Volume	103
DOIs	https://doi.org/10.1016/j.tetlet.2022.153985
Publication status	Published - Aug 3 2022

Keywords

Bromotyrosine alkaloid
Cytotoxicity
Ma'edamine
Marine sponge
Suberea sp.

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.tetlet.2022.153985

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title = "Ma'edamines E and F, rare bromotyrosine alkaloids possessing a 1,2,3,5-tetrasubstituted pyridinium moiety from an Okinawan marine sponge Suberea sp.",

abstract = "Two new bromotyrosine alkaloids, ma'edamines E (1) and F (2), were isolated from an Okinawan marine sponge Suberea sp., and their structures were elucidated by the analyses of spectroscopic (UV, IR, and NMR) and spectrometric (MS) data. Ma'edamines E (1) and F (2) are the second and third examples of natural products possessing an N-alkyl-3,5-diethyl-2-propylpyridinium moiety. Ma'edamine F (2) is the first bromotyrosine alkaloid having both pyridinium and quaternary ammonium moieties. Ma'edamines E (1) and F (2) showed moderate cytotoxicity against L1210 murine leukemia cells in vitro.",

keywords = "Bromotyrosine alkaloid, Cytotoxicity, Ma'edamine, Marine sponge, Suberea sp.",

author = "Kurimoto, {Shin ichiro} and Ayano Okamoto and Satsuki Seino and Jane Fromont and Jun'ichi Kobayashi and Takaaki Kubota",

note = "Funding Information: We thank the late Mr. Nagahama for his help with sponge collection and Mr. K. Chiba, The Instruments Analysis Equipment Research Center, Showa Pharmaceutical University, for measurements of MS. This work was partly supported by Kobayashi Foundation, a Grant-in-Aid for Young Scientists of Showa Pharmaceutical University, and JSPS KAKENHI Grant Numbers JP17K08345, JP19K16398, JP20K07116. Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

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doi = "10.1016/j.tetlet.2022.153985",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Ma'edamines E and F, rare bromotyrosine alkaloids possessing a 1,2,3,5-tetrasubstituted pyridinium moiety from an Okinawan marine sponge Suberea sp.

AU - Kurimoto, Shin ichiro

AU - Okamoto, Ayano

AU - Seino, Satsuki

AU - Fromont, Jane

AU - Kobayashi, Jun'ichi

AU - Kubota, Takaaki

N1 - Funding Information: We thank the late Mr. Nagahama for his help with sponge collection and Mr. K. Chiba, The Instruments Analysis Equipment Research Center, Showa Pharmaceutical University, for measurements of MS. This work was partly supported by Kobayashi Foundation, a Grant-in-Aid for Young Scientists of Showa Pharmaceutical University, and JSPS KAKENHI Grant Numbers JP17K08345, JP19K16398, JP20K07116. Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022/8/3

Y1 - 2022/8/3

N2 - Two new bromotyrosine alkaloids, ma'edamines E (1) and F (2), were isolated from an Okinawan marine sponge Suberea sp., and their structures were elucidated by the analyses of spectroscopic (UV, IR, and NMR) and spectrometric (MS) data. Ma'edamines E (1) and F (2) are the second and third examples of natural products possessing an N-alkyl-3,5-diethyl-2-propylpyridinium moiety. Ma'edamine F (2) is the first bromotyrosine alkaloid having both pyridinium and quaternary ammonium moieties. Ma'edamines E (1) and F (2) showed moderate cytotoxicity against L1210 murine leukemia cells in vitro.

AB - Two new bromotyrosine alkaloids, ma'edamines E (1) and F (2), were isolated from an Okinawan marine sponge Suberea sp., and their structures were elucidated by the analyses of spectroscopic (UV, IR, and NMR) and spectrometric (MS) data. Ma'edamines E (1) and F (2) are the second and third examples of natural products possessing an N-alkyl-3,5-diethyl-2-propylpyridinium moiety. Ma'edamine F (2) is the first bromotyrosine alkaloid having both pyridinium and quaternary ammonium moieties. Ma'edamines E (1) and F (2) showed moderate cytotoxicity against L1210 murine leukemia cells in vitro.

KW - Bromotyrosine alkaloid

KW - Cytotoxicity

KW - Ma'edamine

KW - Marine sponge

KW - Suberea sp.

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Ma'edamines E and F, rare bromotyrosine alkaloids possessing a 1,2,3,5-tetrasubstituted pyridinium moiety from an Okinawan marine sponge Suberea sp.

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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