Date of Award
Master of Science (MS)
College of Science and Mathematics
Chemistry and Biochemistry
Thesis Sponsor/Dissertation Chair/Project Chair
Bioactivity guided fractionation of the EtOAc extract from Psoralidium tenuiflorum afforded the known compound bakuchiol as a racemic mixture. This compound was purified by liquid-liquid partitions and chromatographic techniques followed by characterization with ]H NMR, 13C NMR, and GCMS which agreed with previous literature. Previously, bakuchiol was reported from Psoralea corylirolia and Posoralea glandulosa in nature which are from the same family as P. tenuiflorum. This compound exhibited Staphylococcus epidermidis cytotoxicity.
Two Dimensional NMR (HHCOSY and HETCOR) of bakuchiol indicated a disagreement with the previously described NMR structural assignment; a reassignment is described herein.
Long-term storage followed by attempted reisolation by reverse phase HPLC resulted in 4-hydroxybenzaldehyde which was characterized by H NMR, C NMR, and GCMS. Biosynthetically, bakuchiol appears to have been formed from 4-coumaric acid. The 4-coumaric acid can be converted to 4-hydroxybenzaldehyde by an oxidative-reverse Aldol process. The degradation could be consistent with the combined mevalonic acid/shikimic acid biosynthesis of bakuchiol.
Hsu, Pei-Jan, "Isolation, Characterization, and Degradation of Bakuchiol from Psoralidium tenuiflorum" (2007). Theses, Dissertations and Culminating Projects. 1169.