Ma'edamines C and D, New Bromotyrosine Alkaloids Possessing a Unique Tetrasubstituted Pyridinium Moiety from an Okinawan Marine Sponge Suberea sp.

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

doi:10.1021/acs.orglett.9b03457

Ma'edamines C and D, New Bromotyrosine Alkaloids Possessing a Unique Tetrasubstituted Pyridinium Moiety from an Okinawan Marine Sponge Suberea sp.

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

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

8 Citations (Scopus)

Abstract

Two new bromotyrosine alkaloids, ma'edamines C and D, were isolated from an Okinawan marine sponge Suberea sp. The structures of ma'edamines C and D were elucidated on the basis of spectroscopic data. Ma'edamines C and D were the first natural products possessing a unique tetrasubstituted pyridinium moiety such as N-alkyl-3,5-diethyl-2-propylpyridinium and N-alkyl-3,5-diethyl-4-propylpyridinium, respectively. Ma'edamines C and D exhibited moderate cytotoxicity against murine leukemia cell line L1210 in vitro.

Original language	English
Pages (from-to)	8824-8826
Number of pages	3
Journal	Organic Letters
Volume	21
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.9b03457
Publication status	Published - Nov 1 2019
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Ma'edamines C and D, New Bromotyrosine Alkaloids Possessing a Unique Tetrasubstituted Pyridinium Moiety from an Okinawan Marine Sponge Suberea sp.",

abstract = "Two new bromotyrosine alkaloids, ma'edamines C and D, were isolated from an Okinawan marine sponge Suberea sp. The structures of ma'edamines C and D were elucidated on the basis of spectroscopic data. Ma'edamines C and D were the first natural products possessing a unique tetrasubstituted pyridinium moiety such as N-alkyl-3,5-diethyl-2-propylpyridinium and N-alkyl-3,5-diethyl-4-propylpyridinium, respectively. Ma'edamines C and D exhibited moderate cytotoxicity against murine leukemia cell line L1210 in vitro.",

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

note = "Funding Information: We thank the late Mr. Z. Nagahama for his help with sponge collection and Mr. K. Chiba, The Instrument 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 Nos. JP17K08345 and JP19K16398. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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doi = "10.1021/acs.orglett.9b03457",

language = "English",

volume = "21",

pages = "8824--8826",

journal = "Organic Letters",

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T1 - Ma'edamines C and D, New Bromotyrosine Alkaloids Possessing a Unique Tetrasubstituted Pyridinium Moiety from an Okinawan Marine Sponge Suberea sp.

AU - Kurimoto, Shin ichiro

AU - Seino, Satsuki

AU - Fromont, Jane

AU - Kobayashi, Jun'ichi

AU - Kubota, Takaaki

N1 - Funding Information: We thank the late Mr. Z. Nagahama for his help with sponge collection and Mr. K. Chiba, The Instrument 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 Nos. JP17K08345 and JP19K16398. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/11/1

Y1 - 2019/11/1

N2 - Two new bromotyrosine alkaloids, ma'edamines C and D, were isolated from an Okinawan marine sponge Suberea sp. The structures of ma'edamines C and D were elucidated on the basis of spectroscopic data. Ma'edamines C and D were the first natural products possessing a unique tetrasubstituted pyridinium moiety such as N-alkyl-3,5-diethyl-2-propylpyridinium and N-alkyl-3,5-diethyl-4-propylpyridinium, respectively. Ma'edamines C and D exhibited moderate cytotoxicity against murine leukemia cell line L1210 in vitro.

AB - Two new bromotyrosine alkaloids, ma'edamines C and D, were isolated from an Okinawan marine sponge Suberea sp. The structures of ma'edamines C and D were elucidated on the basis of spectroscopic data. Ma'edamines C and D were the first natural products possessing a unique tetrasubstituted pyridinium moiety such as N-alkyl-3,5-diethyl-2-propylpyridinium and N-alkyl-3,5-diethyl-4-propylpyridinium, respectively. Ma'edamines C and D exhibited moderate cytotoxicity against murine leukemia cell line L1210 in vitro.

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JF - Organic Letters

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Ma'edamines C and D, New Bromotyrosine Alkaloids Possessing a Unique Tetrasubstituted Pyridinium Moiety from an Okinawan Marine Sponge Suberea sp.

Abstract

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