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Mar. Drugs 2018, 16(12), 463; https://doi.org/10.3390/md16120463

Ceratinadins E and F, New Bromotyrosine Alkaloids from an Okinawan Marine Sponge Pseudoceratina sp.

1
Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo 194-8543, Japan
2
Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
3
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
*
Author to whom correspondence should be addressed.
Received: 20 October 2018 / Revised: 10 November 2018 / Accepted: 19 November 2018 / Published: 23 November 2018
(This article belongs to the Collection Bioactive Compounds from Marine Invertebrates)
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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). View Full-Text
Keywords: marine sponge; Pseudoceratina sp.; bromotyrosine alkaloid; ceratinadin; 1,6-dioxa-2-azaspiro[4.6]undecane; 3,5-dibromotyramine; psammaplysin; moloka’iamine; antimalarial activity; Plasmodium falciparum marine sponge; Pseudoceratina sp.; bromotyrosine alkaloid; ceratinadin; 1,6-dioxa-2-azaspiro[4.6]undecane; 3,5-dibromotyramine; psammaplysin; moloka’iamine; antimalarial activity; Plasmodium falciparum
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Kurimoto, S.-I.; Ohno, T.; Hokari, R.; Ishiyama, A.; Iwatsuki, M.; Ōmura, S.; Kobayashi, J.; Kubota, T. Ceratinadins E and F, New Bromotyrosine Alkaloids from an Okinawan Marine Sponge Pseudoceratina sp.. Mar. Drugs 2018, 16, 463.

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