Hop extract oxidation-reaction product, preparing method thereof and use thereof

Abstract

The present invention relates to a hop extract having a reduced bitter taste which shows a fat absorption suppressing effect. More specifically the present invention relates to a hop extract oxidation-reaction product obtained by an oxidation-reaction of a hop extract.

1 . A hop extract oxidation-reaction product comprising at least one of the components or component groups (A), (B), (C), (D), (E):
 (A) α acid   (B) iso α acid   (C) β acid   (D) Oxi-Fr.1   (E) Oxi-Fr.2   
       wherein each weight ratio of (A) to (E) is (D)/((A)+(B))>0.1 or more, or (E)/(C)>2 or more. 
     
     
         2 . The hop extract oxidation-reaction product according to  claim 1 , further comprising at least one of the components (F) β1, β2, β3, β4, and wherein the weight ratio of (F)/(C)>0.3 or more. 
     
     
         3 . The hop extract oxidation-reaction product according to  claim 2 , wherein β1 in (F) comprises any of the compounds represented by the formula (I): 
       
         
           
           
               
               
           
         
         β2 comprises any of the compounds represented by the formula (II): 
       
       
         
           
           
               
               
           
         
         β3 comprises any of the compounds represented by the formula (III) or the formula (IV): 
       
       
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
         β4 comprises any of the compounds represented by the formula (V) or the formula (VI). 
       
       
         
           
           
               
               
           
         
       
     
     
         4 . A hop extract oxidation-reaction product according to  claim 1 , wherein the proportion of the peak area of iso α acid, α acid and β acid to the total peak area (mAU·min) of all the peaks of the hop extract oxidation-reaction product as determined by HPLC analysis is 50% or less wherein said HPLC is performed under the following conditions:
 Column: C18 2.1 mm I.D.×100 mm, particle diameter: 3 μm 
 Flow rate: 0.6 mL/min 
 Elution solvent A: water/phosphoric acid, 1000/0.2 (v/v)+EDTA (free) 0.02% (w/v) 
 Elution solvent B: acetonitrile 
 Elution solvent C: water 
 Injection amount: 3 μL 
 Column temperature: 40° C. 
 Detection wavelength: 270 nm (a detection and quantification wavelength for Oxi-Fr1, Oxi-Fr2, iso α acid and β1-4, and a detection wavelength for α acid and β acid): 355 nm (a quantification wavelength for α acid and β acid) Gradient program: 
 
       
         
           
                 
                 
               
                     
                 
                     
                   Mobile phase 
                 
                     
                   composition % 
                 
                 
                 
                 
                 
                 
               
                     
                   Time min 
                   A 
                   B 
                   C 
                 
                     
                 
                 
                 
                 
                 
                 
               
                     
                   0 
                   90 
                   10 
                   0 
                 
                     
                   26.67 
                   48 
                   52 
                   0 
                 
                     
                   30 
                   25 
                   75 
                   0 
                 
                     
                   32.67 
                   15 
                   85 
                   0 
                 
                     
                   37.67 
                   15 
                   85 
                   0 
                 
                     
                   37.68 
                   0 
                   10 
                   90 
                 
                     
                   41.3 
                   0 
                   10 
                   90 
                 
                     
                   41.31 
                   90 
                   10 
                   0 
                 
                 
                 
                 
               
                     
                   51 
                   stop 
                 
                     
                 
                   (After 37.68 min, the washing and equilibration step). 
                 
             
                
                
                
               
            
             
                
                
               
            
             
                
                
                
                
                
                
                
                
               
            
             
                
                
                
               
            
           
         
       
     
     
         5 . The hop extract oxidation-reaction product according to  claim 1 , which is in a form of a liquid composition. 
     
     
         6 . The hop extract oxidation-reaction product according to  claim 5 , wherein the liquid composition comprises alkaline metal salt. 
     
     
         7 . The hop extract oxidation-reaction product according to  claim 1 , which is obtained by a method comprising: oxidizing powdery mixture comprising a hop extract and a base material. 
     
     
         8 . The hop extract oxidation-reaction product according to  claim 7 , wherein the method further comprising: isolating the hop extract oxidation-reaction product from the oxidized powdery mixture. 
     
     
         9 . A food or drink, comprising the hop extract oxidation-reaction product according to  claim 1 . 
     
     
         10 . A method of preparing a hop extract oxidation-reaction product according to  claim 1 , comprising: oxidizing powdery mixture comprising a hop extract and a base material. 
     
     
         11 . The method according to  claim 10 , wherein the hop extract is extracted with supercritical carbon dioxide or an organic solvent. 
     
     
         12 . The method according to  claim 10 , wherein the base material is selected from food or food additives. 
     
     
         13 . The method according to  claim 10 , wherein the base material is at least one selected from the group consisting of saccharides, polysaccharides, inorganic carriers and brewing raw materials. 
     
     
         14 . The method according to  claim 10 , wherein the base material is at least one selected from the group consisting of starch, dextrin, cyclodextrin, cellulose, diatomaceous earth, perlite, activated earth, activated carbon, silica gel, synthetic adsorption resin, a hop and hop lees. 
     
     
         15 . The method according to  claim 10 , wherein a weight ratio of the hop extract and the base material is 1:1 to 1:10. 
     
     
         16 . The method according to  claim 10 , further comprising: isolating the hop extract oxidation-reaction product from the oxidized powdery mixture. 
     
     
         17 . The method according to  claim 10 , wherein the hop extract comprises at least one component selected from α acid and iso α acid. 
     
     
         18 . The method according to  claim 17 , wherein the hop extract comprises β acid.