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.
ASJC Scopus subject areas
- Organic Chemistry