Tragoponol, a dimeric dihydroisocoumarin from Tragopogon porrifolius L.

Christian Zidorn, Bent O. Petersen, Vipaporn Sareedenchai, Ernst P. Ellmerer, Jens Øllgaard Duus

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A phytochemical re-investigation of Tragopogon porrifolius L. (Asteraceae) yielded (7S,15S)-2,4,12-trihydroxy-7-(4-hydroxyphenyl)-10-methoxy-15-(4-methoxyphenyl)-7,8,15,16-tetrahydrodibenzo[c,i][1,7]dioxacyclododecine-5,13-dione, named tragoponol, a dimeric dihydroisocoumarin.The compound, which represents the first of its kind, is comprised of the open-chained forms of two different mono-methoxylated dihydroisocoumarin moieties, scorzocreticin and hongkongenin, which are connected via two ester bonds to form a macrolide with two lactone moieties featuring a 12-membered ring. The structure of the nearly symmetrical compound was established by HR mass spectrometry, CD measurements, and extensive 1D and 2D NMR experiments. © 2010 Elsevier Ltd. All rights reserved.
Original languageEnglish
JournalTetrahedron Letters
Volume51
Issue number10
Pages (from-to)1390-1393
ISSN0040-4039
DOIs
Publication statusPublished - 2010
Externally publishedYes

Keywords

  • Tragopogon
  • Subtribe Scorzonerinae
  • Tribe Cichorieae
  • Asteraceae
  • Natural products
  • Phenolics

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