Heteroaromatic alkaloids, nakijinamines, from a sponge Suberites sp.

Yohei Takahashi, Naonobu Tanaka, Takaaki Kubota, Haruaki Ishiyama, Azusa Shibazaki, Tohru Gonoi, Jane Fromont, Jun'Ichi Kobayashi

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

The structures of seven new secondary metabolites isolated from an Okinawan marine sponge Suberites sp., nakijinamines A (1), B (2), and F-I (3-6) and 6-bromoconicamin (7), have been elucidated on the basis of spectroscopic analysis, chemical conversion, and conformational analysis. These analyses disclosed that 1-6 were heteroaromatic alkaloids having the hybrid structures of an aaptamine-type alkaloid and an indole alkaloid, while 7 was a bromoindole alkaloid. Nakijinamine I (6) is the first example of an aaptamine-type alkaloid possessing a 1,4-dioxane ring. Antimicrobial activities of 1-7 were evaluated.

Original languageEnglish
Pages (from-to)8545-8550
Number of pages6
JournalTetrahedron
Volume68
Issue number41
DOIs
Publication statusPublished - Oct 14 2012
Externally publishedYes

Keywords

  • Heteroaromatic alkaloids
  • Marine sponge
  • Nakijinamines
  • Suberites sp.

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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