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Mar Drugs ; 16(12)2018 11 23.
Article in English | MEDLINE | ID: mdl-30477099

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).


Subject(s)
Alkaloids/pharmacology , Antimalarials/pharmacology , Plasmodium falciparum/drug effects , Porifera , Tyrosine/analogs & derivatives , Alkaloids/chemistry , Alkaloids/isolation & purification , Animals , Antimalarials/chemistry , Antimalarials/isolation & purification , Circular Dichroism , Magnetic Resonance Spectroscopy , Molecular Structure , Spiro Compounds/chemistry , Spiro Compounds/isolation & purification , Spiro Compounds/pharmacology , Tyrosine/chemistry , Tyrosine/isolation & purification , Tyrosine/pharmacology
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