88125-07-9Relevant academic research and scientific papers
TETRAHYDROFURAN-TYPE TERPENOIDS FROM TANACETUM VULGARE
Appendino, Giovanni,Gariboldi, Pierluigi,Nano, Gian Mario,Tetenyi, Peter
, p. 2545 - 2552 (1984)
Investigation of a rare genotype of Tanacetum vulgare afforded a series of tetrahydrofuran-type terpenoids, whose pattern was different in flowers and leaves.The major constituent of the flowers was the trans Δ3,4-hydroperoxide of davanone, whereas the leaves gave mostly a peroxyhemiketalic compound resulting from the intramolecular cyclization of the cis Δ3,4-hydroperoxide of davanone.Structures were elucidated by spectral data and chemical reactions, including correlation with natural (+)-davanone.The peroxyhemiketalic compound upon acylation of its hydroxyl group gave an instantaneous complex reaction, resulting in the formation of a β-acyloxyenone and loss of one molecule of acetone.Among the minor constituents of the leaves, a C-10 carboxylic acid biogenetically related with davanone was isolated.Key Word Index - Tanacetum vulgare; Compositae; sesquiterpenes; davanone; hydroperoxides; peroxyhemiketals; chemotaxonomy.
Peroxides as plant constituents, XII: Davanone type peroxides from Artemisia abrotanum and their preparation
Rucker,Manns,Wilbert
, p. 457 - 460 (1993)
From the aerial parts of Artemisia abrotanum L. (Asteraceae), besides (+)-Davanone (1) and Arteincultone (2), the known peroxy-semiketals 2, 5, and 7 were isolated. In addition, the previously unknown davanone type peroxides epi-arteincultone (4) and spiro-arteincultone (6) were identified in A. abrotanum by TLC. By means of singlet oxygen oxidation of 1, compounds 2, 3, 4, 5, and 7 are formed, by triplet oxygen oxidation compounds 2, 3, 5, 6, 7 as well as hydroxy-davanone.
