Halichonines A, B, and C, novel sesquiterpene alkaloids from the marine sponge Halichondria okadai Kadota

Osamu Ohno; Tatsuhiko Chiba; Seiji Todoroki; Hideaki Yoshimura; Norihito Maru; Ken Maekawa; Hiroshi Imagawa; Kaoru Yamada; Atsushi Wakamiya; Kiyotake Suenaga; Daisuke Uemura

doi:10.1039/c1cc15557a

Halichonines A, B, and C, novel sesquiterpene alkaloids from the marine sponge Halichondria okadai Kadota

Chem Commun (Camb). 2011 Dec 14;47(46):12453-5. doi: 10.1039/c1cc15557a. Epub 2011 Oct 31.

Authors

Osamu Ohno¹, Tatsuhiko Chiba, Seiji Todoroki, Hideaki Yoshimura, Norihito Maru, Ken Maekawa, Hiroshi Imagawa, Kaoru Yamada, Atsushi Wakamiya, Kiyotake Suenaga, Daisuke Uemura

Affiliation

¹ Department of Chemistry, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.

PMID: 22042320
DOI: 10.1039/c1cc15557a

Abstract

Novel sesquiterpene alkaloids, halichonines A (1), B (2), and C (3), were identified from the marine sponge Halichondria okadai Kadota. By spectroscopic analyses and synthesis, their structures were revealed to include a 6,6-bicyclic ring system and two prenylated amine moieties. In addition, 2 induced apoptosis in HL60 human leukemia cells.

Publication types

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

MeSH terms

Alkaloids / chemistry*
Alkaloids / isolation & purification
Alkaloids / pharmacology*
Animals
Antineoplastic Agents / chemistry*
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
HL-60 Cells
Humans
Inhibitory Concentration 50
Models, Molecular
Molecular Conformation
Porifera / chemistry*
Sesquiterpenes / chemistry*
Sesquiterpenes / isolation & purification
Sesquiterpenes / pharmacology*

Substances

Alkaloids
Antineoplastic Agents
Sesquiterpenes