Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma

Satoru Tamura, Tomomichi Ohno, Yuuhi Hattori, Nobutoshi Murakami

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Falcarindiol (1) was isolated as an algicidal principle against the harmful red tide dinoflagellate, Heterocapsa circularisquama, from Notopterygii Rhizoma through bioassay-guided separation. In order to determine the ambiguous absolute structure of this active principle, all three stereoisomers as well as falcarindiol (1) were synthesized. As a result of intensive analysis of their physicochemical properties, the configuration of 1 was revealed to be 3R,8S. On the other hand, (3S,8S)- and (3S,8R)-isomers were found to exhibit more potent algicidal activity than (3R,8S)-falcarindiol (1) isolated from Notopterygii Rhizoma. In addition, the diyne moiety of 1 was established as the crucial structural requirement for algicidal potency.

Original languageEnglish
Pages (from-to)1523-1525
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number11
DOIs
Publication statusPublished - 2010 Mar 17

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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