Variable-Temperature 1H-NMR Studies on Two C-Glycosylflavones 英文参考文献.docVIP

Molecules 2012, 17, 7914-7926; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Variable-Temperature 1H-NMR Studies on Two C-Glycosylflavones Julia H. Frank 1, Yomica L. Powder-George 1, Russel S. Ramsewak 1,* and William F. Reynolds 2,* 1 Department of Chemistry, The University of the West Indies, St. Augustine, Trinidad and Tobago, West Indies; E-Mails: modelle_cc@ (J.H.F.); pyomica@ (Y.L.P.-G.) 2 Department of Chemistry, University of Toronto, Toronto, ON M5S 3H6, Canada * Authors to whom correspondence should be addressed; E-Mails: russel.ramsewak@ (R.S.R.); wreynold@chem.utoronto.ca (W.F.R.) Received: 5 April 2012; in revised form: 26 May 2012 / Accepted: 18 June 2012 / Published: 2 July 2012 Abstract: Two known C-glycosylflavones, swertisin and embinoidin, were isolated from the leaves of Anthurium aripoense, and characterized by room temperature 1D and 2D NMR experiments. At this temperature, the 1H- and 13C-NMR spectra of these C-glycosylflavones revealed doubling of signals, which suggested the presence of two rotamers in solution. Variable-temperature (VT) 1H-NMR studies supported this hypothesis. The T-ROESY data, in addition to the theoretical (MM2) calculations utilizing the Chem3D Pro software, confirmed the hypothesis that the two rotamers interchange via rotation about the C-glycosidic bond. Keywords: variable-temperature 1H-NMR; C-glycosylflavones; rotamers; swertisin; embinoidin; Anthurium aripoense 1. Introduction Anthurium is a genus of evergreen, climbing or epiphytic herbs which belongs to the Araceae [1], and has reported folkloric uses, which include hallucinogens, insecticides, oral contraceptives, rheumatoid arthritis treatments and skin care agents [2–4]. Anthurium aripoense is a terrestrial or short climbing herb found in Trinidad and Venezuela [5,6]. A survey of the literature revealed tha