Nakijinamines C-E, new heteroaromatic alkaloids from the sponge Suberites species

Yohei Takahashi; Takaaki Kubota; Azusa Shibazaki; Tohru Gonoi; Jane Fromont; Jun'ichi Kobayashi

doi:10.1021/ol2008473

Nakijinamines C-E, new heteroaromatic alkaloids from the sponge Suberites species

Org Lett. 2011 Jun 17;13(12):3016-9. doi: 10.1021/ol2008473. Epub 2011 May 16.

Authors

Yohei Takahashi¹, Takaaki Kubota, Azusa Shibazaki, Tohru Gonoi, Jane Fromont, Jun'ichi Kobayashi

Affiliation

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

PMID: 21574567
DOI: 10.1021/ol2008473

Abstract

Three new heteroaromatic alkaloids, nakijinamines C-E (1-3), which are a hybrid of the aaptamine-type and bromoindole alkaloids possessing a taurine- or histidine-derived residue, have been isolated from an Okinawan marine sponge Suberites species. The structures of 1-3 were elucidated on the basis of spectroscopic data and chemical conversions. Nakijinamines C (1) and E (3) are the first natural products possessing a 1H-oxazolo[4',5':4,5]benzo[1,2,3-de][1,6]naphthyridine ring system.

Publication types

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

MeSH terms

Animals
Aspergillus niger / drug effects
Drug Screening Assays, Antitumor
Hydrocarbons, Brominated / chemistry
Hydrocarbons, Brominated / isolation & purification*
Indole Alkaloids / chemistry
Indole Alkaloids / isolation & purification*
Leukemia P388
Microbial Sensitivity Tests
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Suberites / chemistry*

Substances

Hydrocarbons, Brominated
Indole Alkaloids
nakijinamine C
nakijinamine D
nakijinamine E