Pteroside A2a New Illudane-Type Sesquiterpene Glucoside from Pteridium caudatum L. Maxon, and the Spectrometric Characterization of Caudatodienone
- 27 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Agricultural and Food Chemistry
- Vol. 51 (9) , 2559-2564
- https://doi.org/10.1021/jf026238j
Abstract
Fractionation of an extract of Pteridium caudatum L. Maxon. (syn P. aquilinum L. Kuhn var.caudatum) which had earlier yielded the illudane-type sesquiterpene glucosides, ptaquiloside (1a), isoptaquiloside (1b), and caudatoside (1c) afforded a mixture containing 1a and two minor components. Preparative HPLC afforded ptaquiloside Z (1d) and a new pteroside glucoside (pteroside A2) (3e), which was identified using a combination of mass spectral and one- and two-dimensional NMR analyses. The 1H and 13C NMR and mass spectrometric characterization of caudatodienone (2b), an unstable dienone derived from the degradation of caudatoside (1c) in pyridine solution, and the GC-MS characterization of some pterosin-type degradation products produced by reacting this solution with cosolvents is also reported. Keywords: Pteridium aquilinum; Pteridium caudatum; bracken fern; illudane glucosides; caudatoside; ptaquiloside Z; caudatodienone; pteroside A2Keywords
This publication has 10 references indexed in Scilit:
- Carcinogenic effects of ptaquiloside in bracken fern and related compoundsBritish Journal of Cancer, 2000
- Bracken ptaquiloside in milkNature, 1996
- microcystis aeruginosa: Behaviour and toxic features in San Roque Dam (Argentina)Natural Toxins, 1995
- DNA damage by ptaquiloside, a potent bracken carcinogen: detection of selective strand breaks and identification of DNA cleavage productsJournal of the American Chemical Society, 1994
- Total synthesis of natural (-)-ptaquilosin, the aglycon of a potent bracken carcinogen ptaquiloside and the (+)-enantiomer, and their DNA cleaving activitiesJournal of the American Chemical Society, 1993
- Dennstoside a, an analogue of ptaquiloside, from Dennstaedtia scabraPhytochemistry, 1991
- The sesquiterpenoid carcinogen of bracken fern, and some analogues, from the pteridaceaePhytochemistry, 1990
- Bracken (Pteridium aquilinum)—toxic effects and toxic constituentsJournal of the Science of Food and Agriculture, 1989
- Assay of ptaquiloside, the carcinogenic principle of bracken, Pteridium aquilinum, by mutagenicity testing in Salmonella typhimuriumMutagenesis, 1986
- Separation of carcinogenic fraction of bracken fernCancer Letters, 1984