Journal
PHYTOCHEMISTRY
Volume 68, Issue 8, Pages 1206-1211Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2007.01.022
Keywords
Humulus lupulus; Cannabaceae; hops; high performance liquid chromatography; chiral resolution; naringenin; 8-prenylnaringenin; 6-prenylnaringenin; prenylflavonoids; camphanic acid chloride
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Prenylflavonoids are an unique class of phytochemicals found in the inflorescences of the hop plant (Humulus Inpulus). These flavonoids have demonstrated a wide range of biological activities, which may be influenced by their stereochemical configuration. Additionally, recent studies suggest that hop prenylflavonoids are subject to biotransformations which could alter or enrich their stereochemistry. In order to facilitate studies of the stereoisomers of flavanones, a facile method was developed for resolving the diastereomeric esters of flavanones via reversed-phase HPLC. Herein, a method for forming the tri-(1S)-(-)-camphanic acid esters of the 4',5,7-trihydroxy flavanones naringenin, 8-prenylnaringenin and 6-prenylnaringenin, is described. The respective diastereomers were separated using analytical reversed-phase HPLC. Diastereomeric esters were isolated by preparative HPLC to > 98% d.e. based on HPLC, with their absolute configurations established by application of CD spectrometry. (c) 2007 Elsevier Ltd. All rights reserved.
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