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The marine sponge Agelas citrina as a source of the new pyrrole-imidazole alkaloids citrinamines A-D and N-methylagelongine.

ABSTRACT: The chemical investigation of the Caribbean sponge Agelas citrina revealed four new pyrrole-imidazole alkaloids (PIAs), the citrinamines A-D (1-4) and the bromopyrrole alkaloid N-methylagelongine (5). All citrinamines are dimers of hymenidin (6) which was also isolated from this sponge as the major metabolite. Citrinamines A (1) and B (2) are derivatives of the PIA dimer mauritiamine (7), whereas citrinamine C (3) is derived from the PIA dimer nagelamide B (8). Citrinamine D (4) shows an uncommon linkage between the imidazole rings of both monomeric units as it is only observed in the benzocyclobutane ring moiety of benzosceptrins A-C (9-11). Compound 5 is the N-methyl derivative of agelongine (12) which consist of a pyridinium ring and an ester linkage instead of the aminoimidazole moiety and the common amide bond in PIAs.

SUBMITTER: Cychon C

PROVIDER: S-EPMC4660978 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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The marine sponge Agelas citrina as a source of the new pyrrole-imidazole alkaloids citrinamines A-D and N-methylagelongine.

Cychon Christine C Lichte Ellen E Köck Matthias M

Beilstein journal of organic chemistry 20151029

The chemical investigation of the Caribbean sponge Agelas citrina revealed four new pyrrole-imidazole alkaloids (PIAs), the citrinamines A-D (1-4) and the bromopyrrole alkaloid N-methylagelongine (5). All citrinamines are dimers of hymenidin (6) which was also isolated from this sponge as the major metabolite. Citrinamines A (1) and B (2) are derivatives of the PIA dimer mauritiamine (7), whereas citrinamine C (3) is derived from the PIA dimer nagelamide B (8). Citrinamine D (4) shows an uncommo ...[more]

PMID: 26664624

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