Plant extract compositions and methods of preparation thereof
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.
1. A method of treating an agricultural product, comprising:
obtaining a composition comprising plant-derived fatty acids;
functionalizing the fatty acids by esterification to form fatty acid esters, the fatty acid esters comprising monoacylglycerides;
causing the monoacylglycerides to be added to a solvent, thereby forming a mixture; and
causing the mixture to be applied to a surface of the agricultural product to form a protective coating from the monoacylglycerides over the agricultural product.
2. The method of claim 1 , further comprising causing an emulsifier to be added to the solvent.
3. The method of claim 2 , wherein the solvent is water.
4. The method of claim 1 , wherein the forming of the protective coating further comprises causing the solvent to be removed from the surface of the product.
5. The method of claim 1 , wherein the product is an edible product.
6. The method of claim 1 , wherein the product is an inedible product.
7. The method of claim 1 , wherein the protective coating is formulated to prevent diffusion of gaseous species.
8. The method of claim 1 , wherein the fatty acids comprise at least one of hexadecanoic acid, 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, or 9,10,16-trihydroxyhexadecanoic acid.
9. The method of claim 1 , wherein the fatty acids comprise at least one of octadecanoic acid, 18-hydroxyoctadecanoic acid, 9,18-dihydroxyoctadecanoic acid, 10,18-dihydroxyoctadecanoic acid, or 9,10,18-trihydroxyoctadecanoic acid.
10. The method of claim 1 , wherein the agricultural product is a fruit or a vegetable.
11. The method of claim 1 , wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:
wherein:
R is a 1-glyceryl or a 2-glyceryl;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl, wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 and R 8 are each independently —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 14 and R 15 are each independently —H, —C 1 -C 6 alkyl, —C 1 -C 6 alkenyl, or —C 1 -C 6 alkynyl;
the symbol represents an optionally single or cis or trans double bond;
n is an integer between 0 and 8;
m is an integer between 0 and 3;
q is an integer between 0 and 5; and
r is an integer between 0 and 8.
12. A method of treating an agricultural product, comprising:
obtaining a composition comprising a first group of plant-derived fatty acid esters;
transesterifying the first group of fatty acid esters to form a second group of fatty acid esters different from the first group of fatty acid esters, the second group of fatty acid esters comprising monoacylglycerides; and
causing the monoacylglycerides to be applied to a surface of the agricultural product to form a protective coating from the monoacylglycerides over the agricultural product.
13. The method of claim 12 , wherein the agricultural product is an edible product, and the protective coating serves to reduce moisture loss from the product.
14. The method of claim 12 , wherein the agricultural product is a fruit or a vegetable.
15. The method of claim 12 , wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:
wherein:
R is a 1-glyceryl or a 2-glyceryl;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl, wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 and R 8 are each independently —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 14 and R 15 are each independently —H, —C 1 -C 6 alkyl, —C 1 -C 6 alkenyl, or —C 1 -C 6 alkynyl;
the symbol represents an optionally single or cis or trans double bond;
n is an integer between 0 and 8;
m is an integer between 0 and 3;
q is an integer between 0 and 5; and
r is an integer between 0 and 8.
16. A method of treating an agricultural product, comprising:
obtaining a composition comprising monoacylglycerides, wherein the monoacylglycerides are formed by esterification of plant-derived fatty acids;
causing the composition to be added to a solvent, thereby forming a mixture; and
causing the mixture to be applied to a surface of the agricultural product to form a protective coating from the monoacylglycerides over the agricultural product.
17. The method of claim 16 , wherein the fatty acids comprise at least one of hexadecanoic acid, 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, or 9,10,16-trihydroxyhexadecanoic acid.
18. The method of claim 16 , wherein the fatty acids comprise at least one of octadecanoic acid, 18-hydroxyoctadecanoic acid, 9,18-dihydroxyoctadecanoic acid, 10,18-dihydroxyoctadecanoic acid, or 9,10,18-trihydroxyoctadecanoic acid.
19. The method of claim 16 , wherein the composition further comprises a salt.
20. The method of claim 19 , wherein the mixture further comprises a weak acid.
21. The method of claim 16 , wherein the agricultural product is a fruit or a vegetable.
22. The method of claim 16 , wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:
wherein:
R is a 1-glyceryl or a 2-glyceryl;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl, wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 and R 8 are each independently —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 14 and R 15 are each independently —H, —C 1 -C 6 alkyl, —C 1 -C 6 alkenyl, or —C 1 -C 6 alkynyl;
the symbol represents an optionally single or cis or trans double bond;
n is an integer between 0 and 8;
m is an integer between 0 and 3;
q is an integer between 0 and 5; and
r is an integer between 0 and 8.
23. A method of treating an agricultural product, comprising:
obtaining a composition comprising monoacylglycerides, wherein the monoacylglycerides are formed by transesterification of plant-derived fatty acid esters; and
causing the composition to be applied to a surface of the agricultural product to form a protective coating from the monoacylglycerides over the agricultural product.
24. The method of claim 23 , wherein the protective coating serves to reduce a rate of mass loss in the agricultural product.
25. The method of claim 23 , wherein the agricultural product is a fruit or a vegetable.
26. The method of claim 23 , wherein the monoacylglycerides are compounds of Formula I, wherein Formula I is:
wherein:
R is a 1-glyceryl or a 2-glyceryl;
R 1 , R 2 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl, wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen;
R 3 , R 4 , R 7 and R 8 are each independently —H, —OR 14 , —NR 14 R 15 , —SR 14 , halogen, —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl wherein each —C 1 -C 6 alkyl, —C 2 -C 6 alkenyl, —C 2 -C 6 alkynyl, —C 3 -C 7 cycloalkyl, —C 6 -C 10 aryl, or 5 to 10-membered ring heteroaryl is optionally substituted with —OR 14 , —NR 14 R 15 , —SR 14 , or halogen; or
R 3 and R 4 can combine with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 7 and R 8 can combine with the carbon atoms to which they are attached to form a 3 to 6-membered ring, such as a cyclic ether;
R 14 and R 15 are each independently —H, —C 1 -C 6 alkyl, —C 1 -C 6 alkenyl, or —C 1 -C 6 alkynyl;
the symbol represents an optionally single or cis or trans double bond;
n is an integer between 0 and 8;
m is an integer between 0 and 3;
q is an integer between 0 and 5; and
r is an integer between 0 and 8.