Ceratinadins E and F, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp.

Shin Ichiro Kurimoto; Taito Ohno; Rei Hokari; Aki Ishiyama; Masato Iwatsuki; Satoshi Ōmura; Jun’ichi Kobayashi; Takaaki Kubota

doi:10.3390/md16120463

Ceratinadins E and F, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp.

Shin Ichiro Kurimoto, Taito Ohno, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Satoshi Ōmura, Jun’ichi Kobayashi, Takaaki Kubota

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

21 Citations (Scopus)

Abstract

Two new bromotyrosine alkaloids, ceratinadins E (1) and F (2), were isolated from an Okinawan marine sponge Pseudoceratina sp. as well as a known bromotyrosine alkaloid, psammaplysin F (3). The gross structures of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute configurations of 1 and 2 were assigned by comparison of the NMR and ECD data with those of a known related bromotyrosine alkaloid, psammaplysin A (4). Ceratinadins E (1) and F (2) are new bromotyrosine alkaloids possessing an 8,10-dibromo-9-methoxy-1, 6-dioxa-2-azaspiro[4.6]undeca-2,7,9-trien-4-ol unit with two or three 11-N-methylmoloka’iamine units connected by carbonyl groups, respectively. Ceratinadin E (1) exhibited antimalarial activities against a drug-resistant and a drug-sensitive strains of Plasmodium falciparum (K1 and FCR3 strains, respectively).

Original language	English
Article number	463
Journal	Marine Drugs
Volume	16
Issue number	12
DOIs	https://doi.org/10.3390/md16120463
Publication status	Published - Nov 23 2018
Externally published	Yes

Keywords

1,6-dioxa-2-azaspiro[4.6]undecane
3,5-dibromotyramine
Antimalarial activity
Bromotyrosine alkaloid
Ceratinadin
Marine sponge
Moloka’iamine
Plasmodium falciparum
Psammaplysin
Pseudoceratina sp.

ASJC Scopus subject areas

Drug Discovery

UN SDGs

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

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10.3390/md16120463

Cite this

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title = "Ceratinadins E and F, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp.",

abstract = "Two new bromotyrosine alkaloids, ceratinadins E (1) and F (2), were isolated from an Okinawan marine sponge Pseudoceratina sp. as well as a known bromotyrosine alkaloid, psammaplysin F (3). The gross structures of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute configurations of 1 and 2 were assigned by comparison of the NMR and ECD data with those of a known related bromotyrosine alkaloid, psammaplysin A (4). Ceratinadins E (1) and F (2) are new bromotyrosine alkaloids possessing an 8,10-dibromo-9-methoxy-1, 6-dioxa-2-azaspiro[4.6]undeca-2,7,9-trien-4-ol unit with two or three 11-N-methylmoloka{\textquoteright}iamine units connected by carbonyl groups, respectively. Ceratinadin E (1) exhibited antimalarial activities against a drug-resistant and a drug-sensitive strains of Plasmodium falciparum (K1 and FCR3 strains, respectively).",

keywords = "1,6-dioxa-2-azaspiro[4.6]undecane, 3,5-dibromotyramine, Antimalarial activity, Bromotyrosine alkaloid, Ceratinadin, Marine sponge, Moloka{\textquoteright}iamine, Plasmodium falciparum, Psammaplysin, Pseudoceratina sp.",

author = "Kurimoto, {Shin Ichiro} and Taito Ohno and Rei Hokari and Aki Ishiyama and Masato Iwatsuki and Satoshi Ōmura and Jun{\textquoteright}ichi Kobayashi and Takaaki Kubota",

note = "Publisher Copyright: {\textcopyright} 2018 by the authors.",

year = "2018",

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doi = "10.3390/md16120463",

language = "English",

volume = "16",

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T1 - Ceratinadins E and F, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp.

AU - Kurimoto, Shin Ichiro

AU - Ohno, Taito

AU - Hokari, Rei

AU - Ishiyama, Aki

AU - Iwatsuki, Masato

AU - Ōmura, Satoshi

AU - Kobayashi, Jun’ichi

AU - Kubota, Takaaki

PY - 2018/11/23

Y1 - 2018/11/23

N2 - Two new bromotyrosine alkaloids, ceratinadins E (1) and F (2), were isolated from an Okinawan marine sponge Pseudoceratina sp. as well as a known bromotyrosine alkaloid, psammaplysin F (3). The gross structures of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute configurations of 1 and 2 were assigned by comparison of the NMR and ECD data with those of a known related bromotyrosine alkaloid, psammaplysin A (4). Ceratinadins E (1) and F (2) are new bromotyrosine alkaloids possessing an 8,10-dibromo-9-methoxy-1, 6-dioxa-2-azaspiro[4.6]undeca-2,7,9-trien-4-ol unit with two or three 11-N-methylmoloka’iamine units connected by carbonyl groups, respectively. Ceratinadin E (1) exhibited antimalarial activities against a drug-resistant and a drug-sensitive strains of Plasmodium falciparum (K1 and FCR3 strains, respectively).

AB - Two new bromotyrosine alkaloids, ceratinadins E (1) and F (2), were isolated from an Okinawan marine sponge Pseudoceratina sp. as well as a known bromotyrosine alkaloid, psammaplysin F (3). The gross structures of 1 and 2 were elucidated on the basis of spectroscopic data. The absolute configurations of 1 and 2 were assigned by comparison of the NMR and ECD data with those of a known related bromotyrosine alkaloid, psammaplysin A (4). Ceratinadins E (1) and F (2) are new bromotyrosine alkaloids possessing an 8,10-dibromo-9-methoxy-1, 6-dioxa-2-azaspiro[4.6]undeca-2,7,9-trien-4-ol unit with two or three 11-N-methylmoloka’iamine units connected by carbonyl groups, respectively. Ceratinadin E (1) exhibited antimalarial activities against a drug-resistant and a drug-sensitive strains of Plasmodium falciparum (K1 and FCR3 strains, respectively).

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KW - Ceratinadin

KW - Marine sponge

KW - Moloka’iamine

KW - Plasmodium falciparum

KW - Psammaplysin

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Ceratinadins E and F, new bromotyrosine alkaloids from an Okinawan marine sponge Pseudoceratina sp.

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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