Synthesis of multiply 13C-labeled furofuran lignans using 13C-labeled cinnamyl alcohols as building blocks.
Plant lignans are currently being widely studied for their potential benefits for human health as their consumption has been correlated with lower risks for developing chronic diseases, such as breast cancer and coronary heart disease. However, studies of some classes of lignans, in particular the furofurans, are hampered by the lack of suitable standards to allow accurate analysis. Herein, we report the syntheses of two racemic (13)C-labeled furofuran lignans [7,8,9-(13)C(3)]medioresinol and [7,8,9-(13)C(3)]sesamin as internal standards for LC-MS analysis. The labeled furofuran lignans were constructed from triply labeled cinnamyl alcohols, using a radical cyclization method.
Haajanen
Kati
K
School of Chemistry, University of St. Andrews, St. Andrews, Fife, KY16 9ST Scotland, UK.
Botting
Nigel P
NP
D002247:Carbon Isotopes; D002853:Chromatography, Liquid; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D017705:Lignans / Q000138:chemical synthesis*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D002247:Carbon Isotopes; D005663:Furans; D017705:Lignans; D020005:Propanols; C020722:cinnamyl alcohol