Pteroside A2--a new illudane-type sesquiterpene glucoside from pteridium caudatum L. Maxon, and the spectrometric characterization of caudatodienone.
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 (1)H and (13)C 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.
Castillo
Uvidelio F
UF
Universidad de Los Andes, Facultad de Ciencias, Departamento de Química, Laboratorio de Química Ecológica, Mérida 5101, Venezuela.
Wilkins
Alistair L
AL
Lauren
Denis R
DR
Smith
Barry L
BL
Alonso-Amelot
Miguel
M
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D006027:Glycosides / Q000032:analysis / Q000302:isolation & purification*; D007189:Indans / Q000032:analysis / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D010936:Plant Extracts / Q000032:analysis / Q000302:isolation & purification; D032498:Pteridium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry*
D006027:Glycosides; D007189:Indans; D010936:Plant Extracts; D012717:Sesquiterpenes; C475259:caudatodienone; C010771:pterosides