Compositions of bakuchiol and methods of making the same

Abstract

The present invention provides compositions of bakuchiol (UP246) having low levels of impurities, particularly furanocoumarin impurities. The present invention further provides improved methods for the isolation, purification and analysis of compositions of bakuchiol. Finally, the present invention provides methods for using the purified bakuchiol compositions and formulations thereof for the prevention and treatment of various diseases and conditions mediated by cyclooxygenase (COX), lipoxygenase (LOX), minor inflammatory conditions and various microbial infections. The methods of this invention are comprised of administering to a host in need thereof an effective amount of the composition of this invention together with a pharmaceutically acceptable carrier.

1 - 27 . (canceled) 
     
     
         28 . A method for preparing a plant extract comprising bakuchiol, the method comprising:
 a) extracting a plant or plant part containing bakuchiol with an organic solvent to obtain an organic extract comprising bakuchiol and furanocoumarin impurities;   b) heating the organic extract obtained in step a) in the presence of a base at a temperature and for a time sufficient to hydrolyze a lactone ring of the furanocoumarin impurities; and   c) separating the hydrolyzed furanocoumarin impurities from the bakuchiol to obtain the plant extract comprising bakuchiol, wherein the plant extract is free of furanocoumarin impurities as measured by high pressure liquid chromatography (HPLC).   
     
     
         29 . The method of  claim 28 , wherein the plant or plant part is from the  Psoralea  genus of plants. 
     
     
         30 . The method of  claim 28 , wherein the plant or plant part is from  Otholobium pubescens  (Fabaceae),  Psoralea corylifolia  L. (Luguminosae) or  Psoralea glandulosa  L. (Papilionaceae). 
     
     
         31 . The method of  claim 28 , wherein the plant part is seeds, stems, bark, twigs, tubers, roots, root bark, young shoots, rhixomes, flowers, leaves or combinations thereof. 
     
     
         32 . The method of  claim 28 , wherein the furanocoumarins are psoralen, isopsoralen or combinations thereof. 
     
     
         33 . The method of  claim 28 , wherein step b) comprises refluxing. 
     
     
         34 . The method of  claim 28 , wherein the base comprises a hydroxide base. 
     
     
         35 . The method of  claim 34 , wherein the base is sodium hydroxide, potassium hydroxide, calcium hydroxide or lithium hydroxide. 
     
     
         36 . The method of  claim 28 , wherein separating the hydrolyzed furanocoumarin impurities from the bakuchiol comprises solvent partitioning. 
     
     
         37 . The method of  claim 28 , wherein the method further comprises steps of column chromatography, extraction followed by crystallization, solvent partition, recrystallization or combinations thereof. 
     
     
         38 . The method of  claim 28 , wherein the plant extract comprises from 14 to 100 weight percent of bakuchiol. 
     
     
         39 . The method of  claim 28 , wherein the plant extract comprises from 30 to 100 weight percent of bakuchiol.