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 journalArticlepeer-review

12 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 languageEnglish
Article number463
JournalMarine Drugs
Volume16
Issue number12
DOIs
Publication statusPublished - Nov 23 2018
Externally publishedYes

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

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