Zamamidine C, 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A, and 3,4-dihydromanzamine J N-oxide, new manzamine alkaloids from sponge Amphimedon sp.

Mika Yamada, Yohei Takahashi, Takaaki Kubota, Jane Fromont, Aki Ishiyama, Kazuhiko Otoguro, Haruki Yamada, Satoshi Omura, Jun'ichi Kobayashi

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

New manzamine alkaloids, zamamidine C (1), 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2), and 3,4-dihydromanzamine J N-oxide (3), have been isolated from an Okinawan marine sponge Amphimedon species. The structures and stereochemistries of 1-3 were elucidated from the spectroscopic data and chemical derivatization. Zamamidine C (1) is a new manzamine alkaloid possessing a second β-carboline ring via an ethylene unit at N-2 of manzamine D, while 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2) is the first manzamine alkaloid possessing an epoxide ring at C-10 and C-11. Zamamidine C (1) showed significant antitrypanosomal activity against Trypanosoma brucei brucei, the parasite associated with sleeping sickness, and antimalarial activity against Plasmodium falciparum, the causative agent of malaria in vitro.

Original languageEnglish
Pages (from-to)2313-2317
Number of pages5
JournalTetrahedron
Volume65
Issue number11
DOIs
Publication statusPublished - Mar 14 2009
Externally publishedYes

Keywords

  • 3,4-Dihydro-6-hydroxy-10,11-epoxymanzamine A
  • 3,4-Dihydromanzamine J N-oxide
  • Antimalarial activity
  • Antitrypanosomal activity
  • Manzamine alkaloid
  • Sponge
  • Zamamidine C

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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