US2004242501A1PendingUtilityA1

Spermicidal and virucidal properties of various forms of sophorolipids

54
Priority: Mar 20, 2003Filed: Mar 19, 2004Published: Dec 2, 2004
Est. expiryMar 20, 2023(expired)· nominal 20-yr term from priority
Inventors:Richard A. GrossVishal ShahGustavo F. Doncel
A61P 31/18A61P 31/12C12P 19/44C07H 15/24A61P 15/16A61K 31/704A61K 36/062A61P 15/18A61P 15/00A61K 45/06
54
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Claims

Abstract

A method for producing sophorolipids having spermicidal and/or antiviral properties by synthesizing the sophorolipid by fermentation of Candida bombicola in a fermentation media to form a natural mixture of lactonic sophorolipids compounds and non-lactonic sophorolipids compounds and utilizing the natural mixture as a spermicidal and/or antiviral agent, and/or separating the lactonic sophorolipids from the natural mixture to form a lactonic fraction and mixing all remaining fractions to form a non-lactonic fraction and utilizing the lactonic fraction and/or the non-lactonic fraction as an spermicidal and/or antiviral agent, and sophorolipid compounds for use as spermicidal and/or antiviral agents.

Claims

exact text as granted — not AI-modified
What is claimed is:  
     
         1 . A method for producing sophorolipids having spermicidal and/or antiviral properties comprising the steps of: 
 a. synthesizing the sophorolipid by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;    b. utilizing the natural mixture as a spermicidal and/or antiviral agent;    c. separating the lactonic sophorolipids from the natural mixture to form a lactonic fraction and mixing all remaining fractions to form a non-lactonic fraction;    d. utilizing the lactonic fraction as an spermicidal and/or antiviral agent; and    e. utilizing the non-lactonic fraction as a spermicidal and/or antiviral agent.    
     
     
         2 . A method for producing sophorolipids having spermicidal and/or antiviral properties comprising the steps of: 
 a. synthesizing the sophorolipid by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids; and    b. utilizing the natural mixture as a spermicidal and/or antiviral agent.    
     
     
         3 . A method for producing sophorolipids having spermicidal and/or antiviral properties comprising the steps of: 
 a. synthesizing the sophorolipid by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;    b. separating the lactonic sophorolipids from the natural mixture to form a lactonic fraction and mixing all remaining fractions to form a non-lactonic fraction; and    c. utilizing the lactonic fraction as an spermicidal and/or antiviral agent.    
     
     
         4 . A method for producing sophorolipids having spermicidal and/or antiviral properties comprising the steps of: 
 a. synthesizing the sophorolipid by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;    b. separating the lactonic sophorolipids from the natural mixture to form a lactonic fraction and mixing all remaining fractions to form a non-lactonic fraction; and    c. utilizing the non-lactonic fraction as an spermicidal and/or antiviral agent.    
     
     
         5 . 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.  
     
     
         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 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate, Hexyl 17-L[(2′-O-p-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, and Ethyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         7 . The method as claimed in  claim 2 , wherein the sophorolipid is 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based.  
     
     
         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 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate, Hexyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, and Ethyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         9 . The method as claimed in  claim 3 , wherein the sophorolipid is 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based.  
     
     
         10 . The method as claimed in  claim 9 , 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 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate, Hexyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, and Ethyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         11 . 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.  
     
     
         12 . The method as claimed in  claim 11 , 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 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate, Hexyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, and Ethyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         13 . A method for inactivating spermatozoa using 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based sophorolipids.  
     
     
         14 . The method as claimed in  claim 13 , 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 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate, Hexyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, and Ethyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         15 . A method for neutralizing or inactivating viruses using 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based sophorolipids.  
     
     
         16 . The method as claimed in  claim 15 , 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 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate, Hexyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, and Ethyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         17 . A method for neutralizing or inactivating HIV using 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate based sophorolipids.  
     
     
         18 . The method as claimed in  claim 17 , 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 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate, Hexyl 17-L[(2′-O-p-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate, and Ethyl 17-L[(2′-O-β-D glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         19 . A sophorolipid compound having the formula 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate.  
     
     
         20 . The sophorolipid compound as claimed in  claim 19  having spermicidal properties.  
     
     
         21 . The sophorolipid compound as claimed in  claim 19  having antiviral properties.  
     
     
         22 . A sophorolipid compound having the formula Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         23 . The sophorolipid compound as claimed in  claim 22  having spermicidal properties.  
     
     
         24 . The sophorolipid compound as claimed in  claim 22  having antiviral properties.  
     
     
         25 . A sophorolipid compound having the formula Hexyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate.  
     
     
         26 . The sophorolipid compound as claimed in  claim 25  having spermicidal properties.  
     
     
         27 . The sophorolipid compound as claimed in  claim 25  having anti-viral properties.  
     
     
         28 . The method as claimed in  claim 1 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a gel, a film, a foam, a suppository, a pessary, a liposomic formulation, and as a liquid imbibed in a sponge.  
     
     
         29 . The method as claimed in  claim 2 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a gel, a film, a foam, a suppository, a pessary, a liposomic formulation, and as a liquid imbibed in a sponge.  
     
     
         30 . The method as claimed in  claim 3 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a gel, a film, a foam, a suppository, a pessary, a liposomic formulation, and as a liquid imbibed in a sponge.  
     
     
         31 . The method as claimed in  claim 4 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a gel, a film, a foam, a suppository, a pessary, a liposomic formulation, as a liquid imbibed in a sponge, and as a liquid being released from an intravaginal or intrauterine delivery system.  
     
     
         32 . The sophorolipid compound as claimed in  claim 19 , wherein the sophorolipid compound is in a form selected from the group consisting of a gel, a film, a foam, a suppository, a pessary, a liposomic formulation, as a liquid imbibed in a sponge, and as a liquid being released from an intravaginal or intrauterine delivery system.  
     
     
         33 . The sophorolipid compound as claimed in  claim 20 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a gel, a film, a foam, a suppository, and a pessary.  
     
     
         34 . The sophorolipid compound as claimed in  claim 21 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a liposomic formulation, as a liquid imbibed in a sponge, and as a liquid being released from an intravaginal or intrauterine delivery system.  
     
     
         35 . The sophorolipid compound as claimed in  claim 23 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a gel, a film, a foam, a suppository, and a pessary.  
     
     
         36 . The sophorolipid compound as claimed in  claim 24 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a liposomic formulation, as a liquid imbibed in a sponge, and as a liquid being released from an intravaginal or intrauterine delivery system.  
     
     
         37 . The sophorolipid compound as claimed in  claim 26 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a gel, a film, a foam, a suppository, and a pessary.  
     
     
         38 . The sophorolipid compound as claimed in  claim 27 , wherein the sophorolipid compound is delivered in a form selected from the group consisting of a liposomic formulation, as a liquid imbibed in a sponge, and as a liquid being released from an intravaginal or intrauterine delivery system.  
     
     
         39 . The application of a sophorolipid synthesized by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids in combination with at least one sophorolipid selected from the group consisting of: 
 a. 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate;    b. Ethyl 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; and    d. combinations thereof,    as antiviral agents.    
     
     
         40 . The application of a sophorolipid synthesized by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids in combination with at least one sophorolipid selected from the group consisting of: 
 a. 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate;    b. Ethyl 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; and    d. combinations thereof,    as spermicidal agents.    
     
     
         41 . The application of the sophorolipid as claimed in  claim 19  in combination with at least one sophorolipid selected from the group consisting of: 
 a. Sophorolipids synthesized by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;  
 b. Ethyl 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; and  
 d. combinations thereof,  
 as antiviral agents.  
 
     
     
         42 . The application of the sophorolipid as claimed in  claim 19  in combination with at least one sophorolipid selected from the group consisting of: 
 a. Sophorolipid synthesized by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;  
 b. Ethyl 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; and  
 d. combinations thereof,  
 as spermicidal agents.  
 
     
     
         43 . The application of the sophorolipid as claimed in  claim 22  in combination with at least one sophorolipid selected from the group consisting of: 
 a. Sophorolipid synthesized by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;  
 b. 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate;  
 c. Hexyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate; and  
 d. combinations thereof,  
 as antiviral agents.  
 
     
     
         44 . The application of the sophorolipid as claimed in  claim 22  in combination with at least one sophorolipid selected from the group consisting of: 
 a. Sophorolipid synthesized by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;  
 b. 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate;  
 c. Hexyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-9 octadecenoate; and  
 d. combinations thereof,  
 as spermicidal agents.  
 
     
     
         45 . The application of the sophorolipid as claimed in  claim 25  in combination with at least one sophorolipid selected from the group consisting of: 
 a. Sophorolipid synthesized by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;  
 b. 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate-6′,6″-diacetate;  
 c. Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-9 octadecenoate; and  
 d. combinations thereof,  
 as antiviral agents.  
 
     
     
         46 . The application of the sophorolipid as claimed in  claim 25  in combination with at least one sophorolipid selected from the group consisting of: 
 a. Sophorolipid synthesized by fermentation of  Candida bombicola  in a fermentation media to form a natural mixture of lactonic sophorolipids and non-lactonic sophorolipids;  
 b. 17-L-[(2′-O-1-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-7 octadecenoate-6′,6″-diacetate;  
 c. Ethyl 17-L-[(2′-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]-cis-9-octadecenoate; and  
 d. combinations thereof,  
 as spermicidal agents.  
 
     
     
         47 . The application of the sophorolipids as claimed in  claim 1  in combination with known antiviral agents.  
     
     
         48 . The application of the sophorolipids as claimed in  claim 1  in combination with known spermicidal agents.  
     
     
         49 . The application of the sophorolipids as claimed in  claim 17  in combination with known antiviral agents.  
     
     
         50 . The application of the sophorolipids as claimed in  claim 17  in combination with known spermicidal agents.  
     
     
         51 . The application of the sophorolipids as claimed in  claim 20  in combination with known antiviral agents.  
     
     
         52 . The application of the sophorolipids as claimed in  claim 21  in combination with known spermicidal agents.  
     
     
         53 . The application of the sophorolipids as claimed in  claim 23  in combination with known antiviral agents.  
     
     
         54 . The application of the sophorolipids as claimed in  claim 24  in combination with known spermicidal agents.

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