Zamamidines A and B, new manzamine alkaloids from the sponge Amphimedon species

Yohei Takahashi; Takaaki Kubota; Jane Fromont; Jun'ichi Kobayashi

doi:10.1021/ol802251q

Zamamidines A and B, new manzamine alkaloids from the sponge Amphimedon species

Org Lett. 2009 Jan 1;11(1):21-4. doi: 10.1021/ol802251q.

Authors

Yohei Takahashi¹, Takaaki Kubota, Jane Fromont, Jun'ichi Kobayashi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.

PMID: 19053818
DOI: 10.1021/ol802251q

Abstract

New manzamine alkaloids, zamamidines A (1) and B (2), have been isolated from an Okinawan marine sponge Amphimedon species. The structures and stereochemistry of 1 and 2 were elucidated from the spectroscopic data and conformational analysis. Zamamidines A (1) and B (2) are the first manzamine alkaloids possessing a second beta-carboline ring via an ethylene unit at N-2 of manzamine H and 1,2,3,4-tetrahydromanzamine B, respectively.

Publication types

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

MeSH terms

Alkaloids / chemistry*
Alkaloids / isolation & purification
Animals
Carbazoles / chemistry*
Carbazoles / isolation & purification
Crystallography, X-Ray
Heterocyclic Compounds, 4 or More Rings / chemistry*
Heterocyclic Compounds, 4 or More Rings / isolation & purification
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Porifera / chemistry*
Species Specificity
Stereoisomerism

Substances

Alkaloids
Carbazoles
Heterocyclic Compounds, 4 or More Rings
zamamidine A
zamamidine B