Method of producing proanthocyanidin oligomer

Abstract

The present invention relates to a composition containing as its main component proanthocyanidin oligomer to which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded, and reduced in the molecular weight, which is obtained by heating plant materials containing proanthocyanidin polymer or extract thereof with a substance having a phloroglucinol ring structure or resorcinol ring structure in an acidic aqueous solution, production method thereof, and uses of the composition in health products and pharmaceutical products. According to the invention, proanthocyanidin oligomer having physiological activity, to which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded and reduced in the molecular weight to such a level that the oligomer can be absorbed into living body, which has been conventionally difficult to obtain at high yield from plant raw materials, can be produced efficiently and easily.

1 . A composition containing as its main component proanthocyanidin oligomer to terminal of which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded and reduced in the molecular weight, which is obtained by heating plant materials containing proanthocyanidin polymer or extract thereof with a substance having a phloroglucinol ring structure or resorcinol ring structure, plant containing such a substance or extract thereof in an acidic aqueous solution. 
   
   
       2 . The composition containing as its main component proanthocyanidin oligomer described in  claim 1 , wherein the plant containing proanthocyanidin polymer is at least one kind selected from a group consisting of grape, pine, Chamaecyparis obtuse, camphor tree, wax myrtle, cacao, date plum, banana, Chinese quince, apple, hawthorn, Litchee, Myrica rubra and Cinnamomi Cortex. 
   
   
       3 . The composition containing as its main component proanthocyanidin oligomer described in  claim 1 , wherein the substance having a phloroglucinol ring structure or resorcinol ring structure is at least one kind selected from a group consisting of resveratrol, phloroglucinol, flavonoid and flavonoid (galloylester of catechin). 
   
   
       4 . The composition containing as its main component proanthocyanidin oligomer described in  claim 1 , wherein the substance having a phloroglucinol ring structure or resorcinol ring structure is at least one kind selected from a group consisting of green tea, fresh tea leaves, grape seed, grape seed coat, cube gambir, red algae and extracts thereof. 
   
   
       5 . The composition containing as its main component proanthocyanidin oligomer described in  claim 1 , having a polymerization degree of 2 to 4. 
   
   
       6 . (canceled) 
   
   
       7 . (canceled) 
   
   
       8 . (canceled) 
   
   
       9 . (canceled) 
   
   
       10 . The composition containing proanthocyanidin oligomer according to  claim 1 , wherein said composition is used in health food products for treatment/prevention of lifestyle-related diseases caused by generation of reactive oxygen species and brain diseases or for prevention of aging. 
   
   
       11 . The composition containing proanthocyanidin oligomer described in  claim 10 , used in pharmaceutical products for treatment/prevention of lifestyle-related diseases caused by generation of reactive oxygen species and brain diseases or for prevention of aging. 
   
   
       12 . The composition containing proanthocyanidin oligomer described in  claim 10 , used in cosmetic products for prevention of aging caused by generation of reactive oxygen species. 
   
   
       13 . A proanthocyanidin oligomer represented by formula (1) below. 
     
       
         
         
             
             
         
       
     
     (In the formula, n is 0 or an integer of 1 to 2.) 
   
   
       14 . A proanthocyanidin oligomer represented by formula (2) below. 
     
       
         
         
             
             
         
       
     
     (In the formula, n is 0 or an integer of 1 to 2.) 
   
   
       15 . A method for producing a composition containing as its main component proanthocyanidin oligomer to terminal of which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded and reduced in the molecular weight, comprising a step of heating plant materials containing proanthocyanidin polymer or extract thereof with plants having a phloroglucinol ring structure or resorcinol ring structure or extract thereof in an acidic aqueous solution and a step of concentrating the reaction solution containing proanthocyanidin oligomer having a phloroglucinol ring structure or resorcinol ring structure bonded to the terminals and reduced in the molecular weight and drying the solution. 
   
   
       16 . The method according to  claim 15 , wherein the plant containing proanthocyanidin polymer is at least one kind selected from a group consisting of grape, pine, Chamaecyparis obtuse, camphor tree, wax myrtle, cacao, date plum, banana, Chinese quince, apple, hawthorn, litchee, Myrica rubra and Cinnamomi Cortex. 
   
   
       17 . The method according to  claim 15 , wherein the substance having a phloroglucinol ring structure or resorcinol ring structure is at least one kind selected from a group consisting of resveratrol, phloroglucinol, flavonoid and flavonoid (galloylester of catechin). 
   
   
       18 . The method according to  claim 15 , wherein the substance having a phloroglucinol ring structure or resorcinol ring structure is at least one kind selected from a group consisting of green tea, fresh tea leaves, grape seed, grape seed coat, cube gambir, red algae and extracts thereof. 
   
   
       19 . The method according to  claim 15 , wherein the composition has a polymerization degree of 2 to 4. 
   
   
       20 . The method according to  claim 15 , wherein the acidic condition is prepared by using an inorganic acid, organic acid or both of the two. 
   
   
       21 . The method according to  claim 20 , wherein at least one kind is selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, acetic acid, citric acid, ascorbic acid and malic acid. 
   
   
       22 . A method for producing a composition containing as its main component proanthocyanidin oligomer to terminal of which a substance having a phloroglucinol ring structure or resorcinol ring structure has been bonded and reduced in the molecular weight, comprising a step of concentrating a reaction solution containing proanthocyanidin oligomer having a substance having a phloroglucinol ring structure or resorcinol ring structure bonded at the terminals and reduced in the molecular weight and a step of subjecting the concentrated solution to fractionating treatment. 
   
   
       23 . The method according to  claim 22 , wherein the plant containing proanthocyanidin polymer is at least one kind selected from a group consisting of grape, pine, Chamaecyparis obtuse, camphor tree, wax myrtle, cacao, date plum, banana, Chinese quince, apple, hawthorn, litchee, Myrica rubra and Cinnamomi Cortex. 
   
   
       24 . The method according to  claim 22 , wherein the substance having a phloroglucinol ring structure or resorcinol ring structure is at least one kind selected from a group consisting of resveratrol, phloroglucinol, flavonoid and flavonoid (galloylester of catechin). 
   
   
       25 . The method according to  claim 22 , wherein the substance having a phloroglucinol ring structure or resorcinol ring structure is at least one kind selected from a group consisting of green tea, fresh tea leaves, grape seed, grape seed coat, cube gambir, red algae and extracts thereof. 
   
   
       26 . The method according to  claim 22 , wherein the composition has a polymerization degree of 2 to 4. 
   
   
       27 . The method according to  claim 22 , wherein the acidic condition is prepared by using an inorganic acid, organic acid or both of the two. 
   
   
       28 . The method according to  claim 27 , wherein at least one kind is selected from the group consisting of hydrochloric acid, sulfuric acid, nitric acid, acetic acid, citric acid, ascorbic acid and malic acid.