US2016089357A1PendingUtilityA1

Use of fractionated products of gamboge resin in the treatment of cancer, pain, and inflammation

Assignee: LEE SEN-BINPriority: Jun 11, 2010Filed: Dec 9, 2015Published: Mar 31, 2016
Est. expiryJun 11, 2030(~3.9 yrs left)· nominal 20-yr term from priority
Inventors:Sen-Bin Lee
A61P 35/00A61P 35/02A61P 29/00A61K 36/38C07D 493/22A61K 31/353A61K 31/352
33
PatentIndex Score
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Claims

Abstract

Disclosed herein are seventeen new compounds and five fractionated products obtained from an acetone-extracted product of gamboge resin. The seventeen new compounds and the five fractionated products have activities in inhibiting the growth of tumor/cancer cells. In addition, the acetone-extracted product of gamboge resin and the five fractionated products obtained therefrom have analgesic and anti-inflammatory effects.

Claims

exact text as granted — not AI-modified
1 .- 7 . (canceled) 
     
     
         8 . A method of treating a cancer in a subject, comprising administering to the subject at least one of fractionated products of gamboge resin, the fractionated products being prepared by a process comprising:
 providing an acetone-extracted product from gamboge resin by pulverizing gamboge resin into powder, followed by extracting the pulverized powder with acetone;   fractionating the acetone-extracted product by semi-preparative RP-HPLC so as to provide five eluates;   separately concentrating the five eluates, followed by partitioning in H 2 O and ethyl acetate, so as to obtain five crude fractionated products, and   separately refining the five crude fractionated products by semi-preparative RP-HPLC, concentrating, and partitioning in H 2 O and ethyl acetate, so that a consistent elution profile for each of the five crude fractionated products is obtained,   wherein the fractionated products are:   (1) fractionated product TSB-14A, said fractionated product consisting of formoxanthone A,   
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
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       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process;
 (2) fractionated product TSB-14B, said fractionated product consisting of isomorellic acid, morellic acid, isomorellinol and compounds refined along with such recited compounds in the process; 
 (3) fractionated product TSB-14C, said fractionated product consisting of 30-hydroxyepigambogic acid, 30-hydroxygambogic acid, neogambogic acid, a compound of the formula 
 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process;
 (4) fractionated product TSB-14D, said fractionated product consisting of isomorellin, isogambogenic acid, gambogenic acid, 
 
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process; and
 (5) fractionated product TSB-14E, said fractionated product consisting of gambogic acid, epigambogic acid, isogambogic acid, epiisogambogic acid, desoxymorellin, desoxygambogenin, gambogellic acid, epigambogellic acid, a compound of the formula 
 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process. 
     
     
         9 . A method of treating pain in a subject, comprising administering to the subject an acetone-extracted product from gamboge resin, at least one of fractionated products of gamboge resin, or a combination of the acetone-extracted product and the at least one of the fractionated products, wherein:
 the acetone-extracted product is obtained by pulverizing gamboge resin into powder, followed by extracting the pulverized powder with acetone;   the fractionated products are prepared by a process comprising: providing an acetone-extracted product from gamboge resin by pulverizing gamboge resin into powder, followed by extracting the pulverized powder with acetone;   fractionating the acetone-extracted product by semi-preparative RP-HPLC so as to provide five eluates;   separately concentrating the five eluates, followed by partitioning in H 2 O and ethyl acetate, so as to obtain five crude fractionated products, and   separately refining the five crude fractionated products by semi-preparative RP-HPLC, concentrating, and partitioning in H 2 O and ethyl acetate, so that a consistent elution profile for each of the five crude fractionated products is obtained; and   the fractionated products are:   (1) fractionated product TSB-14A, said fractionated product consisting of formoxanthone A,   
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process;
 (2) fractionated product TSB-14B, said fractionated product consisting of isomorellic acid, morellic acid, isomorellinol and compounds refined along with such recited compounds in the process; 
 (3) fractionated product TSB-14C, said fractionated product consisting of 30-hydroxyepigambogic acid, 30-hydroxygambogic acid, neogambogic acid, a compound of the formula 
 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process;
 (4) fractionated product TSB-14D, said fractionated product consisting of isomorellin, isogambogenic acid, gambogenic acid, 
 
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process; and
 (5) fractionated product TSB-14E, said fractionated product consisting of gambogic acid, epigambogic acid, isogambogic acid, epiisogambogic acid, desoxymorellin, desoxygambogenin, gambogellic acid, epigambogellic acid, a compound of the formula 
 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process. 
     
     
         10 . A method of treating inflammation in a subject, comprising administering to the subject an acetone-extracted product from gamboge resin, at least one of fractionated products of gamboge resin, or a combination of the acetone-extracted product and the at least one of the fractionated products, wherein:
 the acetone-extracted product is obtained by pulverizing gamboge resin into powder, followed by extracting the pulverized powder with acetone;   the fractionated products are prepared by a process comprising:   providing an acetone-extracted product from gamboge resin by pulverizing gamboge resin into powder, followed by extracting the pulverized powder with acetone;   fractionating the acetone-extracted product by semi-preparative RP-HPLC so as to provide five eluates;   separately concentrating the five eluates, followed by partitioning in H 2 O and ethyl acetate, so as to obtain five crude fractionated products, and   separately refining the five crude fractionated products by semi-preparative RP-HPLC, concentrating, and partitioning in H 2 O and ethyl acetate, so that a consistent elution profile for each of the five crude fractionated products is obtained; and   the fractionated products are:   (1) fractionated product TSB-14A, said fractionated product consisting of formoxanthone A,   
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process;
 (2) fractionated product TSB-14B, said fractionated product consisting of isomorellic acid, morellic acid, isomorellinol and compounds refined along with such recited compounds in the process; 
 (3) fractionated product TSB-14C, said fractionated product consisting of 30-hydroxyepigambogic acid, 30-hydroxygambogic acid, neogambogic acid, a compound of the formula 
 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process;
 (4) fractionated product TSB-14D, said fractionated product consisting of isomorellin, isogambogenic acid, gambogenic acid, 
 
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process; and
 (5) fractionated product TSB-14E, said fractionated product consisting of gambogic acid, epigambogic acid, isogambogic acid, epiisogambogic acid, desoxymorellin, desoxygambogenin, gambogellic acid, epigambogellic acid, a compound of the formula 
 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       a compound of the formula 
       
         
           
           
               
               
           
         
       
       and compounds refined along with such recited compounds in the process.

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