Plant extract compositions and methods of preparation thereof

Patent metadata

Field	Value
Publication number	US-9743679-B2
Application number	US-201615254263-A
Country	US
Kind code	B2
Filing date	Sep 1, 2016
Priority date	May 20, 2015
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

Embodiments described herein relate generally to plant extract compositions and methods to isolate cutin-derived monomers, oligomers, and mixtures thereof for application in agricultural coating formulations, and in particular, to methods of preparing plant extract compositions that include functionalized and non-functionalized fatty acids and fatty esters (as well as their oligomers and mixtures thereof), which are substantially free from accompanying plant-derived compounds (e.g., proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, and aldehydes) and can be used in agricultural coating formulations.

First claim

The invention claimed is:

1. A method of preparing a plant extract composition, comprising:
obtaining cutin from a cutin-containing portion of a plant matter, the cutin-containing portion being at least partially separated from a non-cutin-containing portion of the plant matter;
at least partially depolymerizing the cutin in a first solvent to obtain a first solution comprising a first intermediate extract dissolved in the first solvent, the first intermediate extract including a plurality of cutin-derived monomers, oligomers, or combinations thereof:
acidifying the first intermediate extract:
selectively filtering the first intermediate extract to obtain a second intermediate extract having a higher purity than the first intermediate extract;
functionalizing the cutin-derived monomers, oligomers, or combinations thereof of the second intermediate extract by esterification; and
dissolving the functionalized second intermediate extract in a second solvent to obtain the plant extract composition.

2. The method of claim 1 , wherein obtaining the second intermediate extract includes removing the second intermediate extract from the first solvent.

3. The method of claim 2 , wherein the first solvent includes at least one of chloroform, hexane, acetonitrile, and ethyl acetate.

4. The method of claim 1 , wherein selectively filtering the first intermediate extract includes solidifying the first intermediate extract and washing the solidified first intermediate extract in a selective solvent.

5. The method of claim 1 , wherein the first solution has a pH in the range of 10 to 14.

6. The method of claim 1 , wherein the first solvent is less than 5% water by mass.

7. The method of claim 6 , wherein the first solvent comprises at least one of ethanol and methanol.

8. A method of preparing a plant extract composition, comprising:
obtaining cutin from a cutin-containing portion of a plant matter, the cutin-containing portion being at least partially separated from the non-cutin-containing portion of the plant matter;
at least partially depolymerizing the cutin in a first solvent, the first intermediate extract including a plurality of cutin-derived monomers, oligomers, or combinations thereof;
selectively filtering the first intermediate extract to obtain a second intermediate extract having a higher purity than the first intermediate extract, the second intermediate extract including at least one of the cutin-derived monomers, oligomers, or combinations thereof; and
functionalizing the cutin-derived monomers, oligomers, or combinations thereof of the second intermediate extract by esterification to form the plant extract composition.

9. The method of claim 8 , further comprising:
causing the plant extract composition to be applied to a plant or agricultural product to form a protective coating over the plant or agricultural product.

10. The method of claim 9 , wherein the plant or agricultural product to which the plant extract composition is applied is different from the plant from which the cutin is obtained.

11. The method of claim 8 , wherein functionalizing the cutin-derived monomers, oligomers, or combinations thereof comprises glycerating the cutin-derived monomers, oligomers, or combinations thereof to form monoacylglyceride compounds.

12. The method of claim 8 , wherein functionalizing the cutin-derived monomers, oligomers, or combinations thereof comprises esterifying the cutin-derived monomers, oligomers, or combinations thereof to form ethyl esters.

13. A method of preserving an agricultural product, comprising:
obtaining a plant extract composition comprising a plurality of cutin-derived monomers, oligomers, or combinations thereof;
functionalizing the cutin-derived monomers, oligomers, or combinations thereof by esterifying the cutin-derived monomers, oligomers, or combinations thereof with a glycerol molecule; and
causing the agricultural product to be coated with the functionalized cutin-derived monomers, oligomers, or combinations thereof.

14. The method of claim 13 , wherein the cutin-derived monomers, oligomers, or combinations thereof comprise fatty acids.

15. The method of claim 14 , wherein the fatty acids are palmitic acid or 10-16-dihydroxyhexadecanoic acid.

16. The method of claim 13 , wherein obtaining the plant extract composition comprises at least partially depolymerizing cutin derived from plant matter.

17. The method of claim 13 , wherein the functionalized cutin-derived monomers, oligomers, or combinations thereof are dissolved in a solvent prior to coating the agricultural product.

18. The method of claim 17 , wherein the solvent is water, ethanol, or a combination thereof.

19. The method of claim 13 , wherein the process of coating the agricultural product with the functionalized cutin-derived monomers, oligomers, or combinations thereof comprises dip-coating or spray-coating of the agricultural product with a solution comprising the functionalized cutin-derived monomers, oligomers, or combinations thereof.

20. The method of claim 13 , wherein the process of coating the agricultural product with the functionalized cutin-derived monomers, oligomers, or combinations thereof causes one or more of the functionalized cutin-derived monomers or oligomers to cross-link on the surface of the product.

21. The method of claim 13 , wherein the cutin-derived monomers, oligomers, or combinations thereof are functionalized by esterifying as a 1-glycerol or a 2-glycerol ester.

22. The method of claim 13 , wherein the functionalized cutin-derived monomers, oligomers, or combinations thereof are not naturally occurring on the surface of the agricultural product.

23. A method of treating an agricultural product, comprising:
obtaining a plant extract composition comprising a plurality of monomers, oligomers, or combinations thereof, wherein the monomers, oligomers or combinations thereof comprise fatty acids or esters;
functionalizing the monomers, oligomers, or combinations thereof by esterification; and
causing the agricultural product to be coated with the functionalized monomers, oligomers, or combinations thereof.

24. The method of claim 23 , wherein obtaining the plant extract composition comprises at least partially depolymerizing cutin derived from plant matter.

25. The method of claim 23 , wherein the functionalized monomers, oligomers, or combinations thereof are dissolved in a solvent prior to coating the agricultural product.

26. The method of claim 25 , wherein the solvent is ethanol, water, or a combination thereof.

27. The method of claim 23 , wherein the process of coating the agricultural product with the functionalized monomers, oligomers, or combinations thereof comprises dip-coating or spray-coating of the agricultural product with a solution comprising the functionalized monomers, oligomers, or combinations thereof.

28. The method of claim 23 , wherein the process of coating the agricultural product with the functionalized monomers, oligomers, or combinations thereof causes one or more of the functionalized monomers or oligomers to cross-link on the surface of the agricultural product.

29. The method of claim 23 , wherein the monomers, oligomers, or combinations thereof are functionalized by esterifying as a 1-glycerol or a 2-glycerol ester.

30. The method of claim 23 , wherein t

Assignees

• Apeel Tech Inc

Inventors

• Perez Louis
• Rogers James
• Bakus Ii Ronald C
• Holland Chance
• Du Jenny

Classifications

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A23B7/16 Primary

  Coating with a protective layer; Compositions or apparatus therefor (A23B7/08 takes precedence) · CPC title

• B01D11/0288

  Applications, solvents · CPC title

• A23B7/154 Primary

  Organic compounds; Microorganisms; Enzymes · CPC title

• B01D11/0284

  Multistage extraction · CPC title