title: Unusual withanolides from aeroponically grown Withania somnifera.
abstract: In an attempt to maximize production and the structural diversity of plant metabolites, the effect of growing the medicinal plant Withania somnifera under soil-less aeroponic conditions on its ability to produce withaferin A and withanolides was investigated. It resulted in the isolation and characterization of two compounds, 3α-(uracil-1-yl)-2,3-dihydrowithaferin A (1) and 3β-(adenin-9-yl)-2,3-dihydrowithaferin A (2), in addition to 10 known withanolides including 2,3-dihydrowithaferin A-3β-O-sulfate. 3β-O-Butyl-2,3-dihydrowithaferin A (3), presumably an artifact formed from withaferin A during the isolation process was also encountered. Reaction of withaferin A with uracil afforded 1 and its epimer, 3β-(uracil-1-yl)-2,3-dihydrowithaferin A (4). The structures of these compounds were elucidated on the basis of their high resolution mass and NMR spectroscopic data.
authors.affiliation: SW Center for Natural Products Research and Commercialization, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, The University of Arizona, 250 E. Valencia Road, Tucson, AZ 85706-6800, USA.
authors.forename: Ya-ming
authors.initials: YM
authors.lastname: Xu
authors.forename: Song
authors.initials: S
authors.lastname: Gao
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Bunting
authors.forename: A A Leslie
authors.initials: AA
authors.lastname: Gunatilaka
mesh_terms: D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry; D032341:Withania / Q000737:chemistry* / Q000254:growth & development*; D054358:Withanolides / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D054358:Withanolides