Antifungal properties of various forms of sophorolipids

Abstract

The preparation and use of 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, Lactonic and Open ring 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, Methyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, Hexyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6″-acetate and Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate sophorolipids as antifungal agents.

1 . A method for producing sophorolipids having antifungal properties comprising the steps of: 
 a) synthesizing the sophorolipid by fermentation of  Candida bombicola  in a fermentation media to form a mixture of lactonic sophorolipids and non-lactonic sophorolipids;    b) separating the lactonic sophorolipids from the mixture to form a lactonic fraction; and    c) utilizing the lactonic fraction as an antifungal agent.    
     
     
         2 . The method as claimed in  claim 1 , wherein the sophorolipid is 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based.  
     
     
         3 . The method as claimed in  claim 2 , wherein the 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based sophorolipid is selected from the group consisting of: 
 a) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate;    b) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6″-acetate;    c) -Ethyl-17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate;    d) Methyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate; and    e) Hexyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate.    
     
     
         4 . A method for producing sophorolipids having antifungal properties comprising the steps of: 
 a) synthesizing the sophorolipid by fermentation of  Candida bombicola  in a fermentation media to form a mixture comprising open ring sophorolipids;    b) separating the open ring sophorolipids from the mixture to form an open ring fraction; and    c) utilizing the open ring sophorolipid fraction as an antifungal agent.    
     
     
         5 . The method as claimed in  claim 4 , wherein the sophorolipid is 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based.  
     
     
         6 . The method as claimed in  claim 5 , wherein the 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based sophorolipid is selected from the group consisting of: 
 a) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate;    b) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6″-acetate;    c) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate;    d) Methyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate; and    e) Hexyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate.    
     
     
         7 . A method for neutralizing fungi by treating the fungi involved with 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based sophorolipids.  
     
     
         8 . The method as claimed in  claim 7 , wherein the 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based sophorolipid is selected from the group consisting of: 
 a) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate;    b) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6″-acetate;    c) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate;    d) Methyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate; and    e) Hexyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate.    
     
     
         9 . A sophorolipid compound having antifungal properties, wherein the sophorolipid compound is selected from the group consisting of: 
 a) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate;    b) Methyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate;    c) Hexyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate;    d) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6″-acetate; and    e) Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate.