Structures of Zeylenol and Zeylena, Constituents of Uvaria zeylanica (Annonaceae)

Shivanand D. Jolad, Joseph J. Hoffmann, Karl H. Schram, Jack R. Cole, Michael S. Tempesta, Robert B. Bates

Research output: Contribution to journalArticlepeer-review

78 Scopus citations

Abstract

From the methanol extract of the roots of Uvaria zeylanica (Annonaceae), two new crystalline compounds, named zeylenol and zeylena, have been isolated. Evidence is presented that zeylenol, C21H20O7, a minor constituent, has structure la and that zeylena, C23H20O5, a major constituent, has structure 3a. Benzene oxide 6 is an apparent biogenetic precursor for these two and many other substances found in Uvaria species; its conversion to zeylena (3a) involves addition of (E)-cinnamic acid followed by an intramolecular Diels-Alder reaction.

Original languageEnglish (US)
Pages (from-to)4267-4272
Number of pages6
JournalJournal of Organic Chemistry
Volume46
Issue number21
DOIs
StatePublished - Oct 1981

ASJC Scopus subject areas

  • Organic Chemistry

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