Oils having antibacterial activity

Patent metadata

Field	Value
Publication number	US-9950986-B2
Application number	US-201515126182-A
Country	US
Kind code	B2
Filing date	Mar 16, 2015
Priority date	Mar 20, 2014
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

Novel compounds, called liamocins from Aureobasidium pullulans , having the general structure in Formula 1 are disclosed.

where R 1 is either COCH 3 or H; and R 2 is between two to ten O-linked 3,5-dihydroxydecanoate; and R 3 can be a polyol (e.g., L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol (also called sorbitol), L- or D-galactitol (also called dulcitol), and L- or D-talitol), 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; except when R 3 is D-mannitol, R 2 is not 2 nor 3 O-linked 3,5-dihydroxydecanoate chains. These liamocins described above in addition to D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, and D-mannitol liamocin B2, alone or in combination with each other, can be used to kill certain bacteria and to treat certain bacterial infections.

First claim

We, the inventors, claim:

1. A composition having anti-bacterial activity comprising one or more of the compounds of Formula 1, optionally a carrier, and optionally a diluent, wherein said compounds of Formula 1 can kill Streptococcus spp., Enterococcus spp., and Bacillus spp., and wherein Formula 1 is

where R 1 is, independently, either COCH 3 or H; and R 2 is, independently, between two to ten O-linked 3,5-dihydroxydecanoate; and R 3 is, independently, one of the following: L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol, L- or D-galactitol, L- or D-talitol, 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; except when R 3 is D-mannitol, R 2 is not 2 nor 3 O-linked 3,5-dihydroxydecanoate chains.

2. A method of treating a disease caused by Streptococcus spp., Enterococcus spp., or Bacillus spp. in an animal having said disease comprising administering a therapeutically effective amount of a composition to said animal to kill said Streptococcus spp., said Enterococcus spp., or said Bacillus spp., wherein said composition comprises an oil having the chemical structure of Formula 1

where R 1 is, independently, either COCH 3 or H; and R 2 is, independently, between two to ten O-linked 3,5-dihydroxydecanoate; and R 3 is, independently, one of the following: L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol, L- or D-galactitol, L- or D-talitol, 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; and a combination thereof; optionally a carrier; and optionally a diluent.

3. The method of claim 2 , wherein said oil is selected from the group comprising L-mannitol liamocin A1, L-mannitol liamocin A2, L-mannitol liamocin B1, L-mannitol liamocin B2, D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, D-mannitol liamocin B2, L-arabitol liamocin A1, L-arabitol liamocin A2, L-arabitol liamocin B1, L-arabitol liamocin B2, D-arabitol liamocin A1, D-arabitol liamocin A2, D-arabitol liamocin B1, D-arabitol liamocin B2, L-threitol liamocin A1, L-threitol liamocin A2, L-threitol liamocin B1, L-threitol liamocin B2, D-threitol liamocin A1, D-threitol liamocin A2, D-threitol liamocin B1, D-threitol liamocin B2, L-glycerol liamocin A1, L-glycerol liamocin A2, L-glycerol liamocin B1, L-glycerol liamocin B2, D-glycerol liamocin A1, D-glycerol liamocin A2, D-glycerol liamocin B1, and D-glycerol liamocin B2.

4. The method of claim 2 , wherein said method further comprises administering said composition topically, orally, or parenterally to said animal.

5. The method of claim 2 , wherein said animal is selected from the group consisting of a mammal, a bird, a fish, an amphibian, and a reptile.

6. A method of reducing the population of Streptococcus spp., Enterococcus spp., or Bacillus spp. on a surface comprising applying to said surface an effective amount of a composition to reduce the population of said Streptococcus spp., said Enterococcus spp., or said Bacillus spp., wherein said composition comprises an oil having the chemical structure of Formula 1

where R 1 is, independently, either COCH 3 or H; and R 2 is, independently, between two to ten O-linked 3,5-dihydroxydecanoate; and R 3 is, independently, one of the following: L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol, L- or D-galactitol, L- or D-talitol, 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; and a combination thereof; optionally a carrier; and optionally a diluent.

7. The method of claim 6 , wherein said oil is selected from the group comprising L-mannitol liamocin A1, L-mannitol liamocin A2, L-mannitol liamocin B1, L-mannitol liamocin B2, D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, D-mannitol liamocin B2, L-arabitol liamocin A1, L-arabitol liamocin A2, L-arabitol liamocin B1, L-arabitol liamocin B2, D-arabitol liamocin A1, D-arabitol liamocin A2, D-arabitol liamocin B1, D-arabitol liamocin B2, D-threitol liamocin A1, D-threitol liamocin A2, D-threitol liamocin B1, D-threitol liamocin B2, L-glycerol liamocin A1, L-glycerol liamocin A2, L-glycerol liamocin B1, L-glycerol liamocin B2, D-glycerol liamocin A1, D-glycerol liamocin A2, D-glycerol liamocin B1, and D-glycerol liamocin B2.

8. A method of killing Streptococcus spp., Enterococcus spp., or Bacillus spp. growing on a surface comprising applying to said surface an effective amount of a composition to kill said Streptococcus spp., said Enterococcus spp., or said Bacillus spp., wherein said composition comprises an oil having the chemical structure of Formula 1

where R 1 is, independently, either COCH 3 or H; and R 2 is, independently, between two to ten O-linked 3,5-dihydroxydecanoate; and R 3 is, independently, one of the following: L- or D-glycerol, L- or D-threitol, L- or D-erythritol, L- or D-arabitol, L- or D-xylitol, L- or D-lyxitol, L- or D-ribitol, L- or D-allitol, L- or D-altritol, L- or D-mannitol, L- or D-iditol, L- or D-gulitol, L- or D-glucitol, L- or D-galactitol, L- or D-talitol, 2-amino-D-mannitol, 2N-acetylamino-D-mannitol, L-rhamnitol, or D-fucitol; and a combination thereof; optionally a carrier; and optionally a diluent.

9. The method of claim 8 , wherein said oil is selected from the group comprising L-mannitol liamocin A1, L-mannitol liamocin A2, L-mannitol liamocin B1, L-mannitol liamocin B2, D-mannitol liamocin A1, D-mannitol liamocin A2, D-mannitol liamocin B1, D-mannitol liamocin B2, L-arabitol liamocin A1, L-arabitol liamocin A2, L-arabitol liamocin B1, L-arabitol liamocin B2, D-arabitol liamocin A1, D-arabitol liamocin A2, D-arabitol liamocin B1, D-arabitol liamocin B2, L-threitol liamocin A1, L-threitol liamocin A2, L-threitol liamocin B1, L-threitol liamocin B2, D-threitol liamocin A1, D-threitol liamocin A2, D-threitol liamocin B1, D-threitol liamocin B2, L-glycerol liamocin A1, L-glycerol liamocin A2, L-glycerol liamocin B1, L-glycerol liamocin B2, D-glycerol liamocin A1, D-glycerol liamocin A2, D-glycerol liamocin B1, and D-glycerol liamocin B2.

Assignees

• Us Agriculture

Inventors

• Bischoff Kenneth M
• Leathers Timothy D
• Price Neil P
• Manitchotpisit Pennapa

Classifications

• A61P31/12

  Antivirals · CPC title

• C07C69/675 Primary

  of saturated hydroxy-carboxylic acids · CPC title

• A61K31/191

  having two or more hydroxy groups, e.g. gluconic acid · CPC title

• A01N37/36

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids · CPC title

• C07C69/21

  of hydroxy compounds with more than three hydroxy groups (esters of sugars C07H) · CPC title