Antimicrobial ferulic acid derivatives and uses thereof

Abstract

Antimicrobial diferulates, compositions containing same, and uses of same for inhibiting growth of microorganisms. The antimicrobial diferulates can be used alone or in combination with other antimicrobial agents to inhibit growth of microorganisms such as fungi, oomycetes, and other microorganisms having a glucan-containing cell wall. The antimicrobial diferulates can be included in pharmaceutical compositions for treatment of animals or included in agricultural compositions for treatment of plants, crops, and soils.

What is claimed is: 
     
         1 . An antimicrobial composition comprising an antimicrobial-effective amount of a substantially purified compound selected from the group consisting of a compound of Formula I, a compound of Formula II, and combinations thereof, in combination with an inert carrier, wherein:
 the compound of Formula I is selected from the group consisting of:   
       
         
           
           
               
               
           
         
       
       wherein R 1 -R 5  are each independently selected from the group consisting of hydrogen, C1-C6 linear, branched, or cyclic alkyl, and C6 aryl; and a salt thereof; and
 the compound of Formula II is selected from the group consisting of: 
 
       
         
           
           
               
               
           
         
       
       wherein R 6 -R 10  are each independently selected from the group consisting of hydrogen, C1-C6 linear, branched, or cyclic alkyl, and C6 aryl; and a salt thereof. 
     
     
         2 . The composition of  claim 1  wherein the substantially purified compound comprises the compound of Formula I and the compound of Formula II. 
     
     
         3 . The composition of  claim 1  wherein the compound of Formula I is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       and a salt thereof. 
     
     
         4 . The composition of  claim 1  wherein the compound of Formula II is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       and a salt thereof. 
     
     
         5 . The composition of  claim 1  wherein the composition is substantially devoid of one or more diferulate compounds selected from the group consisting of 5-5 diferulate, 8-5-O diferulate, 8-8-C diferulate, 8-8-THF diferulate, 4-O-5 diferulate, 8-O-4 diferulate, and 8-8-O diferulate. 
     
     
         6 . The composition of  claim 1  wherein the composition comprises from about 0.01% to about 95% by mass of the substantially purified compound. 
     
     
         7 . The composition of  claim 1  wherein the composition comprises at least 5% water by mass. 
     
     
         8 . The composition of  claim 1  wherein the inert carrier comprises a solid carrier. 
     
     
         9 . The composition of  claim 1  wherein the inert carrier comprises a semi-solid carrier. 
     
     
         10 . The composition of  claim 1  wherein the inert carrier comprises a liquid carrier including at least 5% water by mass. 
     
     
         11 . The composition of  claim 1  further comprising an additional antimicrobial compound. 
     
     
         12 . The composition of  claim 11  wherein the additional antimicrobial compound comprises an antifungal compound. 
     
     
         13 . The composition of  claim 12  wherein the antifungal compound comprises a cell-wall targeting agent. 
     
     
         14 . A method of inhibiting growth of a microorganism comprising contacting the microorganism with a composition as recited in  claim 1 . 
     
     
         15 . The method of  claim 14  wherein the microorganism comprises a glucan-containing cell wall. 
     
     
         16 . The method of  claim 14  wherein the microorganism is selected from the group consisting of a fungus and an oomycete. 
     
     
         17 . A method of inhibiting microbial infection in a host comprising administering to the host a composition as recited in  claim 1 . 
     
     
         18 . The method of  claim 17  wherein the administering inhibits growth of a microorganism comprising a glucan-containing cell wall. 
     
     
         19 . The method of  claim 17  wherein the administering inhibits growth of a microorganism selected from the group consisting of a fungus and an oomycete. 
     
     
         20 . The method of  claim 17  wherein the host is an animal. 
     
     
         21 . The method of  claim 17  wherein the host is a plant. 
     
     
         22 . A method of inhibiting growth of a microorganism comprising contacting the microorganism with an effective amount of a substantially purified compound selected from the group consisting of a compound of Formula I, a compound of Formula II, and combinations thereof, wherein:
 the compound of Formula I is selected from the group consisting of:   
       
         
           
           
               
               
           
         
       
       wherein R 1 -R 5  are each independently selected from the group consisting of hydrogen, C1-C6 linear, branched, or cyclic alkyl, and C6 aryl; and a salt thereof; and
 the compound of Formula II is selected from the group consisting of: 
 
       
         
           
           
               
               
           
         
       
       wherein R 6 -R 10  are each independently selected from the group consisting of hydrogen, C1-C6 linear, branched, or cyclic alkyl, and C6 aryl; and a salt thereof.