Synthesis of a tricyclic bisguanidine compound structurally related to saxitoxin and its identification in paralytic shellfish toxin-producing microorganisms

Shigeki Tsuchiya, Yuko Cho, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima, Mari Yotsu-Yamashita

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

We recently reported the chemical synthesis and identification of the genetically predicted biosynthetic intermediates of saxitoxin (STX), including a 2-aminoimidazole-bearing monoguanidine compound (Int-C2) in two paralytic shellfish toxin (PST)-producing microorganisms. In this study, we achieved the direct conversion of Int-C′2 into a tricyclic bisguanidine compound (called Cyclic-C′), which is structurally related to STX, through oxidative intramolecular guanidine transfer to 2-aminoimidazole catalyzed by Pd/C under basic conditions in air. By using HPLC-MS analysis, Cyclic-C′ was also identified in the PST-producing microorganisms, suggesting that Cyclic-C′ is either another biosynthetic intermediate or a shunt product of PSTs. In addition, a weak inhibitory activity of Cyclic-C′ to the voltage-gated sodium channels was detected by using a cell-based assay.

Original languageEnglish
Pages (from-to)7835-7840
Number of pages6
JournalChemistry - A European Journal
Volume21
Issue number21
DOIs
Publication statusPublished - 2015 May 18

Keywords

  • biosynthesis
  • cyclization
  • natural products
  • palladium
  • toxicology

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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