Eudistomidin G, a new β-carboline alkaloid from the Okinawan marine tunicate Eudistoma glaucus and structure revision of eudistomidin B

Yohei Takahashi, Haruaki Ishiyama, Takaaki Kubota, Jun'ichi Kobayashi

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

A new β-carboline alkaloid, eudistomidin G (1), has been isolated from the Okinawan marine tunicate Eudistoma glaucus, and the structure was elucidated from spectroscopic data. Furthermore, the structure of eudistomidin B (2), which has been isolated from the same tunicate, was revised from 2a to 2b by detailed analyses of spectroscopic data. Asymmetric synthesis of the revised structure (2b) of eudistomidin B (2) and its (1S,10S)-diastereomer (2c) has been accomplished with the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of eudistomidin B (2) was confirmed to be 2b possessing (1R,10S)-configuration, from comparison of the 1H NMR data, CD spectra, [α] D values, and HPLC analysis of 2b, 2c, and natural eudistomidin B.

Original languageEnglish
Pages (from-to)4100-4103
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume20
Issue number14
DOIs
Publication statusPublished - Jul 15 2010
Externally publishedYes

Keywords

  • β-Carboline alkaloids
  • Eudistoma glaucus
  • Eudistomidins B and G
  • Tunicate

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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