(2E,9E)-pyronaamidine 9-(N-methylimine), a new imidazole alkaloid from the northern Mariana islands sponge Leucetta sp. cf. chagosensis

A Plubrukarn; D W Smith; R E Cramer; B S Davidson

doi:10.1021/np960673o

(2E,9E)-pyronaamidine 9-(N-methylimine), a new imidazole alkaloid from the northern Mariana islands sponge Leucetta sp. cf. chagosensis

J Nat Prod. 1997 Jul;60(7):712-5. doi: 10.1021/np960673o.

Authors

A Plubrukarn¹, D W Smith, R E Cramer, B S Davidson

Affiliation

¹ Department of Chemistry, University of Hawaii at Manoa, Honolulu 96822, USA.

PMID: 9249976
DOI: 10.1021/np960673o

Abstract

A new imidazole alkaloid, (2E,9E)-pyronaamidine 9-(N-methylimine) (4), was isolated along with the known compounds pyronaamidine (3) and kealiiquinone (5) from the yellow sponge Leucetta sp. cf. chagosensis collected near the Island of Rota, Northern Mariana Islands. Single-crystal X-ray diffraction analysis allowed the unambiguous assignment of the structure of compound 4, including the position of the exchangeable proton and the geometry of the two imino double bonds. Compound 4 exhibited mild cytotoxicity toward the A-549, MCF-7, and HT-29 human tumor cell lines.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification*
Animals
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification*
Humans
Imidazoles / chemistry
Imidazoles / isolation & purification*
Molecular Structure
Porifera / chemistry*
Tumor Cells, Cultured
X-Ray Diffraction

Substances

Alkaloids
Antineoplastic Agents
Imidazoles
pyronaamidine 9-(N-methylimine)