Identification of tricyclic guanidino compounds from the tetrodotoxin-bearing newt taricha granulosa

Yuta Kudo, Charles T. Hanifin, Mari Yamashita

Research output: Contribution to journalArticlepeer-review

Abstract

The biosynthesis of the potent neurotoxin tetrodotoxin (TTX, 1) is still unresolved. We used MS-guided screening and nuclear magnetic resonance analyses including long-range HSQMBC to characterize two novel skeletal tricyclic guanidino compounds, Tgr-288 (2a and 2b) and Tgr-210 (3), from the TTX-bearing newt, Taricha granulosa. The presence of these compounds in toxic newts is congruent with a previously proposed pathway for TTX biosynthesis in terrestrial organisms that includes a monoterpene precursor and the production of structurally diversified guanidino compounds.

Original languageEnglish
Pages (from-to)3513-3517
Number of pages5
JournalOrganic letters
Volume23
Issue number9
DOIs
Publication statusPublished - 2021 May 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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