WO2023150072A1

WO2023150072A1 - Compositions and methods for the preservation of plant matter

Info

Publication number: WO2023150072A1
Application number: PCT/US2023/011839
Authority: WO
Inventors: David A. Sinclair
Original assignee: Sinclair David A
Priority date: 2022-02-01
Filing date: 2023-01-30
Publication date: 2023-08-10

Abstract

The present invention relates to a composition of cutin-derived monomers and oligomers and xenohormetic compounds or derivatives thereof, as well as xenhormetin conjugates, for the preservation of plants and/or plant parts.

Description

COMPOSITIONS AND METHODS FOR THE PRESERVATION OF PLANT MATTER

RELATED APPLICATION

This application claims priority to U.S. Provisional Application No. 63/305368, filed on February 1, 2022. The entire contents of the aforementioned application is incorporated herein by reference.

FIELD OF THE DISCLOSURE

[0001] The present invention relates to a composition of xenohormetic compounds or derivatives thereof with cutin-derived monomers and oligomers, and methods for extending the shelf-life of plant matter.

BACKGROUND

[0002] Most fruit and vegetable products are harvested in a fairly narrow time period or season. However, consumer demand remains high for fresh produce out of season. Often, fresh produce is transported hundreds of miles from the initial site of harvest and stored for many months after harvest. For these reasons, it is desirable to extend produce shelf-life. "Shelf-life" is the time that elapses before stored foods become unsuitable for use due to degradation. The migration of moisture, oxygen or other components in foods can cause deleterious changes in the taste, texture, smell, nutritive value, and storage stability of products. The typical shelf-life of a fruit or vegetable (i.e., fresh produce) depends on several factors including ripeness at time of harvest, handling conditions, and storage conditions.

[0003] Agricultural products (e.g., fruits, vegetables, produce, flowers, and/or whole plants) are susceptible to degradation and decomposition/spoilage when exposed to the environment thereby decreasing their shelf-life. The degradation of agricultural products can occur via abiotic or biotic processes. Generally, degradation via an abiotic process is the result of evaporative moisture loss from the external surface of the agricultural products to the atmosphere and/or oxidation by oxygen that diffuses into the agricultural products from the environment and/or mechanical damage to the surface and/or light- induced degradation (i.e., photodegradation). Furthermore, biotic stressors such as bacteria, fungi, viruses, and/or pests can also infest and decompose the agricultural products.

[0004] The most common methods currently utilized for reducing water loss of postharvest produce include lowering the temperature and/or raising the relative humidity (RH) of the storage environment. However, these storage environments can cause chilling injury, enhance disease development and increased incidence of fruit decay. Additionally, the low temperature storage environments require costly equipment and constant supply of energy to keep the temperature and humidity at a constant level. Despite the benefits afforded by refrigeration, the handling and transportation of agricultural products can cause surface abrasion or bruising that serves as points of ingress for bacteria and fungi.

[0005] Coating fresh fruits and/or vegetables is preservation technique which has been employed with varying degrees of success. Not only must the coating be effective in prolonging the useful shelf-life of the fresh product, but the appearance of the product must not be detrimentally altered. The selection of a coating material is further complicated where the fruit or vegetable is to be consumed in its natural state and it is considered essential that there be no need to remove the coating. In that event, the coating material must not only be edible, it must not affect or alter the natural organoleptic characteristics of the fresh fruit or vegetable.

[0006] Typical of these prior art coatings are the wax emulsions of U.S. Pat. No. 2,560,820 to Recker and U.S. Pat. No. 2,703,760 to Cunning. Coatings of natural materials have been employed including milk whey (U.S. Pat. No. 2,282,801 to Musher), lecithin (U.S. Pat. No. 2,470,281 to Allingham and U.S. Pat. No. 3,451,826 to Mulder), gelatin together with polyhydric alcohol (U.S. Pat. No. 3,556,814 to Whitman et al.) and protein (U.S. Pat. No.

4,344,971 to Garbutt). Polymers have also been used extensively, examples of which include thermoplastic polymers (U.S. Pat. No. 2,213,557 to Tisdale et al.), vinyl acetate polymers (U.S. Pat. No. 3,410,696 to Rosenfield), hydrophilic polymers (U.S. Pat. No. 3,669,691 to De Long et al.) and the combination of water soluble polymers and a hydrophobic material (U.S. Pat. No. 3,997,674 to Ukai et al.). Cellulosic materials have found utility in coating fruits and vegetables including hydrated cellulose (U.S. Pat. No. 1,774,866 to Beadle), a combination of cellulose and wax (U.S. Pat. No. 2,364,614 to Beatty), cellulose ether in combination with a fatty acid ester (U.S. Pat. No. 3,471,303 to Hamdy et al.) or monoglyceride and a fatty acid metal salt (U.S. Pat. No. 3,461,304 to Hamdy et al.), or a sucrose ester of a fatty acid (U.S. Pat. No. 4,338,342 to Tan et al.).

[0007] Notwithstanding these efforts, there remains a substantial need in the art for improved preservation of produce. In particular, pressure from worldwide urbanization, manufacturing, and population growth necessitates development of new technologies to increase the efficiency and yield of natural resources expended on delivering food to the growing global population. In the United States, for example, it is estimated that between 8% and 16% of profit loss of fresh produce is due to spoilage and shrinkage which is estimated at $8 billion-$28 billion system wide. This loss translates to significant wasted resources, for example pesticides, fertilizer, and herbicide use; land and water use; transportation, including oil and gas use; and resources associated with the storage of produce. Loss of these and other resources are due to inefficiencies in production and delivery that allows significant spoilage of fruits and vegetables before these critical products can reach the consumer.

[0008] Therefore, there is a strong need for methods for further improving the shelf-life of fruits and vegetables which avoid the drawbacks resulting from the prior art methods.

SUMMARY

[0009] The present disclosure addresses these challenges by providing composition for the preservation of plant matter (e.g., produce, such as fruits and vegetables). Disclosed herein are compositions for coating or forming a film on a plant and/or plant part. The compositions are useful to improve the shelf-life of plants and/or plant parts (e.g., produce).

[0010] Accordingly, in one aspect, the present disclosure provides compositions for coating or forming a film on a plant and/or plant part. The compositions include one or more cutin- derived monomers, oligomers, or combinations thereof; and one or more xenohormetic compounds or derivatives thereof. In some embodiments, the xenohormetic compound is a flavone, flavanone, isoflavone, isoflavanone, stilbene, catechin, chaicone, tannin, anthocyanidin, polyphenol, or a derivative thereof. In further embodiments, the compositions include one or more nicotinamide adenine dinucleotide (NAD) increasing compounds (e.g., nicotinic acid or nicotinic acid riboside).

[0011] In some embodiments of the compositions described herein, the cutin-derived monomers, oligomers, or combinations thereof comprises compounds of Formula (I), Formula (II), and/or Formula (III):

(Formula I)

wherein for Formula (I):

R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, and R¹⁰ are each independently — H, — OR¹³, — NR¹³R¹⁴, —SR¹³, halogen, — Ci-C₆ alkyl, — Ci-C₆ alkenyl, — Ci-C₆ alkynyl, — C₃- C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹³, — NR¹³R¹⁴, — SR¹³, or halogen;

R¹³ and R¹⁴ are each independently — H, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, or — Ci- Ce alkynyl;

R¹¹ is — H, — glyceryl, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, — C₁-C₆ alkynyl, — C₃- C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹³, — NR¹³R¹⁴, — SR¹³, or halogen;

R¹² is —OH, — H, — Ci-C₆ alkyl, — Ci-C₆ alkenyl, — Ci-C₆ alkynyl, — C₃- C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹³, — NR¹³R¹⁴, — SR¹³, halogen, — COOH, or — COOR¹¹; and m, n, and o are each independently an integer in the range of 0 to 30, and 0<m+n+o<30; wherein for Formula II:

R¹, R², R⁴ and R⁵ are each independently — H, — OR¹¹, — NR¹¹R¹², — SR¹¹, halogen, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, — C₁-C₆ alkynyl, — C₃-C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹¹, — NRⁿR¹², — SR¹¹, or halogen; R¹¹ and R¹² are each independently — H, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, or — Ci- Ce alkynyl; the symbol represents an optionally single or cis or trans double bond; the symbol = represents a cis or trans double bond;

R³ is — OH and R³ is selected from the group consisting of — H, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, — C₁-C₆ alkynyl, — C3-C7 cycloalkyl, and aryl when between

R³ and R³’ is a single bond, and R³ and R³’ are absent when between R³ and R³ represents a double bond; n is an integer in the range of 0 to 11; m is an integer in the range of 0 to 25; and

0<m+n<25; wherein for Formula III:

R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², and R¹³ are each independently, at each occurrence, — H, — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, halogen, — C₁-C₆ alkyl, — C2-C6 alkenyl, — C2-C6 alkynyl, — C3-C7 cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, or halogen;

R³, R⁴, R⁷, and R⁸ are each independently, at each occurrence, — H, — OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, halogen, — Ci-C₆ alkyl, — C₂-C₆ alkenyl, — C₂-C₆ alkenyl, — C₂- Ce alkynyl, — C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen; or

R³ and R⁴ can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or

R⁷ and R⁸ can combine with the carbon atoms to which they are attached to form a C3-C6 cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle;

R¹⁴ and R¹⁵ are each independently, at each occurrence, — H, — C₁-C₆ alkyl, — C2-C6 alkenyl, or — C2-C6 alkynyl; the symbol represents a single bond or a cis or trans double bond; the symbol = represents a cis or trans double bond; n is 0, 1, 2, 3, 4, 5, 6, 7 or 8; m is 0, 1, 2 or 3; q is 0, 1, 2, 3, 4 or 5; r is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and R is selected from — H, — C₁-C₆ alkyl, — C2-C6 alkenyl, — C2-C6 alkynyl, — C3- C7 cycloalkyl, aryl, 1-glyceryl, 2-glyceryl, or heteroaryl.

[0012] A further aspect of the present invention relates to a method of preparing a composition of xenohormetic compounds and cutin-derived monomers, oligomers, or combinations thereof. The method includes providing cutin-derived monomers, oligomers, or combinations thereof; providing xenohormetic compounds; and combining the xenohormetic compounds and cutin-derived monomers, oligomers, or combinations thereof in a solvent to form a first mixture.

[0013] Another aspect of the present invention relates to a xenhormetin conjugate of Formula (IV) for coating or forming a film on a plant and/or plant part: wherein:

Q is a xenhormetin moiety;

X is O, or N;

R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², and R¹³ are independently selected at each occurrence from — H, —OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, halogen, — Ci-C₆ alkyl, — C₂-C₆ alkenyl, — C2- Ce alkynyl, — C3-C7 cycloalkyl, aryl, and heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen;

R³, R⁴, R⁷, and R⁸ are independently selected at each occurrence from — H, — OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, halogen, — Ci-C₆ alkyl, — C₂-C₆ alkenyl, — C₂-C₆ alkenyl, — C₂-C₆ alkynyl, — C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen; or

R³ and R⁴ can combine with the carbon atoms to which they are attached to form a C3- Ce cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or

R⁷ and R⁸ can combine with the carbon atoms to which they are attached to form a C3- Ce cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle;

R¹⁴ and R¹⁵ are independently selected at each occurrence from — H, — C₁-C₆ alkyl, — C2-C6 alkenyl, and — C2-C6 alkynyl;

= represents a single bond or a cis or trans double bond; a is 0 or 1 ;

[0014] In some embodiments of the xenhormetin conjugate, Q is a moiety selected from the group consisting of flavones, isoflavones, stilbenes, flavanones, isoflavanones, catechins, chaicones, tannins, and anthocyanidins.

[0015] A further aspect of the present invention relates to a method of forming the xenhormetin conjugate of Formula (IV), wherein Formula (IV) is as described supra. The method includes providing a xenohormetin compound; obtaining cutin from cutin-containing plant matter; adding the xenohormetin compound and cutin to a solvent to form a first mixture, the solvent having a boiling point at a first temperature at a pressure of one atmosphere; and heating the first mixture to a second temperature and second pressure, the second temperature being higher than the first temperature and the second pressure being higher than one atmosphere, to form a second mixture comprising the xenohormetin-conjugate of Formula (IV). [0016] Another aspect of the present invention relates to a method for preserving a plant and/or plant part. The method includes providing a plant and/or plant part; applying to the surface of the plant and/or plant part the compositions or conjugates described herein, thereby forming a coating on the plant and/or plant part.

[0017] Those skilled in the art will recognize or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments of the invention described herein. Such equivalents are intended to be encompassed by the following enumerated embodiments.

[0018] The details of various aspects or embodiments of the present disclosure are set forth below. Other features, objects, and advantages of the disclosure will be apparent from the description and the claims. In the description, the singular forms also include the plural unless the context clearly dictates otherwise. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art in the field of this disclosure. In the case of conflict, the present description will control. DETAILED DESCRIPTION

Overview

[0019] Described herein are compositions for the preservation of a plant and/or plant part (e.g., produce, such as fruits or vegetables). A first aspect of the present invention relates to a composition for coating or forming a film on a plant and/or plant part comprising one or more cutin-derived monomers, oligomers, or combinations thereof; and one or more xenohormetic compounds or derivatives thereof. The compositions and compounds described herein are able to preserve (e.g., extend the shelf-life of) produce including fruits and vegetables.

[0020] In order that the present description may be more readily understood, certain terms are first defined. Additional definitions are set forth throughout the detailed description. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art.

[0021] The term “cis” is art-recognized and refers to the arrangement of two atoms or groups around a double bond such that the atoms or groups are on the same side of the double bond. Cis configurations are often labeled as (Z) configurations.

[0022] The term “trans” is art-recognized and refers to the arrangement of two atoms or groups around a double bond such that the atoms or groups are on the opposite sides of a double bond. Trans configurations are often labeled as (E) configurations.

[0023] The term “aliphatic” is art-recognized and refers to a linear, branched, cyclic alkane, alkene, or alkyne. In certain embodiments, aliphatic groups in the present compounds are linear or branched and have from 1 to about 20 carbon atoms.

[0024] The term “alkyl” is art-recognized, and includes saturated aliphatic groups, including straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl (alicyclic) groups, alkyl substituted cycloalkyl groups, and cycloalkyl substituted alkyl groups. In certain embodiments, a straight chain or branched chain alkyl has about 30 or fewer carbon atoms in its backbone (e.g., Ci-C ofor straight chain, C3-C30 for branched chain), and alternatively, about 20 or fewer.

Likewise, cycloalkyls have from about 3 to about 10 carbon atoms in their ring structure, and alternatively about 5, 6 or 7 carbons in the ring structure. The term “alkyl” is also defined to include halosubstituted alkyls.

[0025] The term “aralkyl” is art-recognized and refers to an alkyl group substituted with an aryl group (e.g., an aromatic or heteroaromatic group).

[0026] The terms “alkenyl” and “alkynyl” are art-recognized and refer to unsaturated aliphatic groups analogous in length and possible substitution to the alkyls described above, but that contain at least one double or triple bond respectively. [0027] Unless the number of carbons is otherwise specified, “lower alkyl” refers to an alkyl group, as defined above, but having from one to about ten carbons, alternatively from one to about six carbon atoms in its backbone structure. Likewise, “lower alkenyl” and “lower alkynyl” have similar chain lengths.

[0028] The term “heteroatom” is art-recognized and refers to an atom of any element other than carbon or hydrogen. Illustrative heteroatoms include boron, nitrogen, oxygen, phosphorus, sulfur and selenium.

[0029] The term “aryl” is art-recognized and refers to 5-, 6- and 7-membered single-ring aromatic groups that may include from zero to four heteroatoms, for example, benzene, naphtalene, anthracene, pyrene, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine, pyridazine and pyrimidine, and the like. Those aryl groups having heteroatoms in the ring structure may also be referred to as “aryl heterocycles” or “heteroaromatics.” The aromatic ring may be substituted at one or more ring positions with such substituents as described above, for example, halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxyl, amino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, sulfonamide, ketone, aldehyde, ester, heterocyclyl, aromatic or heteroaromatic moieties, — CF3, — CN, or the like. The term “aryl” also includes polycyclic ring systems having two or more cyclic rings in which two or more carbons are common to two adjoining rings (the rings are “fused rings”) wherein at least one of the rings is aromatic, e.g., the other cyclic rings may be cycloalkyls, cycloalkenyls, cycloalkynyls, aryls and/or heterocyclyls.

[0030] The terms ortho, meta and para are art-recognized and refer to 1,2-, 1,3- and 1,4- disubstituted benzenes, respectively. For example, the names 1,2-dimethylbenzene and ortho- dimethylbenzene are synonymous.

[0031] The terms “heterocyclyl” or “heterocyclic group” are art-recognized and refer to 3- to about 10-membered ring structures, alternatively 3- to about 7-membered rings, whose ring structures include one to four heteroatoms. Heterocycles may also be polycycles. Heterocyclyl groups include, for example, thiophene, thianthrene, furan, pyran, isobenzofuran, chromene, xanthene, phenoxanthene, pyrrole, imidazole, pyrazole, isothiazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indolizine, isoindole, indole, indazole, purine, quinolizine, isoquinoline, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, carbazole, carboline, phenanthridine, acridine, pyrimidine, phenanthroline, phenazine, phenarsazine, phenothiazine, furazan, phenoxazine, pyrrolidine, oxolane, thiolane, oxazole, piperidine, piperazine, morpholine, lactones, lactams such as azetidinones and pyrrolidinones, sultams, sultones, and the like. The heterocyclic ring may be substituted at one or more positions with such substituents as described above, as for example, halogen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, ketone, aldehyde, ester, a heterocyclyl, an aromatic or heteroaromatic moiety, — CF3, — CN, or the like.

[0032] The terms “polycyclyl” or “polycyclic group” are art-recognized and refer to two or more rings (e.g., cycloalkyls, cycloalkenyls, cycloalkynyls, aryls and/or heterocyclyls) in which two or more carbons are common to two adjoining rings, e.g., the rings are “fused rings”. Rings that are joined through non-adjacent atoms are termed “bridged” rings. Each of the rings of the polycycle may be substituted with such substituents as described above, as for example, halogen, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, amino, nitro, sulfhydryl, imino, amido, phosphonate, phosphinate, carbonyl, carboxyl, silyl, ether, alkylthio, sulfonyl, ketone, aldehyde, ester, a heterocyclyl, an aromatic or heteroaromatic moiety, — CF3, — CN, or the like. [0033] The term “carbocycle” is art-recognized and refers to an aromatic or non-aromatic ring in which each atom of the ring is carbon.

[0034] The term “nitro” is art-recognized and refers to — NO2; the term “halogen” is art- recognized and refers to — F, — Cl, — Br or — I; the term “sulfhydryl” is art-recognized and refers to — SH; the term “hydroxyl” means — OH; and the term “sulfonyl” is art-recognized and refers to — SO2 ”. “Halide” designates the corresponding anion of the halogens, and “pseudohalide” has the definition set forth on 560 of “Advanced Inorganic Chemistry” by Cotton and Wilkinson.

[0035] The terms “amine” and “amino” are art-recognized and refer to both unsubstituted and substituted amines, e.g., a moiety that may be represented by the general formulas:

wherein R50, R51 and R52 each independently represent a hydrogen, an alkyl, an alkenyl, — (CH₂) m - R61, or R50 and R51, taken together with the N atom to which they are attached complete a heterocycle having from 4 to 8 atoms in the ring structure; R61 represents an aryl, a cycloalkyl, a cycloalkenyl, a heterocycle or a polycycle; and m is zero or an integer in the range of 1 to 8. In certain embodiments, only one of R50 or R51 may be a carbonyl, e.g., R50, R51 and the nitrogen together do not form an imide. In other embodiments, R50 and R51 (and optionally R52) each independently represent a hydrogen, an alkyl, an alkenyl, or — (CH2)_m — R61. Thus, the term “alkylamine” includes an amine group, as defined above, having a substituted or unsubstituted alkyl attached thereto, i.e., at least one of R50 and R51 is an alkyl group.

[0036] The term “acylamino” is art-recognized and refers to a moiety that may be represented by the general formula:

wherein R50 is as defined above, and R54 represents a hydrogen, an alkyl, an alkenyl or — (CH2)m — R61, where m and R61 are as defined above.

[0037] The term “amido” is art recognized as an amino-substituted carbonyl and includes a moiety that may be represented by the general formula:

wherein R50 and R51 are as defined above. Certain embodiments of amides may not include imides which may be unstable.

[0038] The term “alkylthio” refers to an alkyl group, as defined above, having a sulfur radical attached thereto. In certain embodiments, the “alkylthio” moiety is represented by one of -S- alkyl, -S-alkenyl, -S-alkynyl, and — S — (CH2)_m — R61, wherein m and R61 are defined above. Representative alkylthio groups include methylthio, ethyl thio, and the like.

[0039] The term “carbonyl” is art recognized and includes such moieties as may be represented by the general formulas:

wherein X50 is a bond or represents an oxygen or a sulfur, and R55 and R56 represents a hydrogen, an alkyl, an alkenyl, — (CH2)_m — R61 or a pharmaceutically acceptable salt, R56 represents a hydrogen, an alkyl, an alkenyl or — (CH2)_m — R61, where m and R61 are defined above. Where X50 is an oxygen and R55 or R56 is not hydrogen, the formula represents an “ester”. Where X50 is an oxygen, and R55 is as defined above, the moiety is referred to herein as a carboxyl group, and particularly when R55 is a hydrogen, the formula represents a “carboxylic acid”. Where X50 is an oxygen, and R56 is hydrogen, the formula represents a “formate”. In general, where the oxygen atom of the above formula is replaced by sulfur, the formula represents a “thiolcarbonyl” group. Where X50 is a sulfur and R55 or R56 is not hydrogen, the formula represents a “thiolester.” Where X50 is a sulfur and R55 is hydrogen, the formula represents a “thiolcarboxylic acid.” Where X50 is a sulfur and R56 is hydrogen, the formula represents a “thiolformate.” On the other hand, where X50 is a bond, and R55 is not hydrogen, the above formula represents a “ketone” group. Where X50 is a bond, and R55 is hydrogen, the above formula represents an “aldehyde” group.

[0040] The terms “alkoxy!” or “alkoxy” are art-recognized and refer to an alkyl group, as defined above, having an oxygen radical attached thereto. Representative alkoxyl groups include methoxy, ethoxy, propyloxy, tert-butoxy and the like. An “ether” is two hydrocarbons covalently linked by an oxygen. Accordingly, the substituent of an alkyl that renders that alkyl an ether is or resembles an alkoxyl, such as may be represented by one of -O-alkyl, -O-alkenyl, -

O-alkynyl, — O — (CH2)_m — R61, where m and R61 are described above.

[0041] The term “sulfonate” is art recognized and refers to a moiety that may be represented by the general formula:

in which R57 is an electron pair, hydrogen, alkyl, cycloalkyl, or aryl.

[0042] The term “sulfate” is art recognized and includes a moiety that may be represented by the general formula: in which R57 is as defined above.

[0043] The term “sulfonamide” is art recognized and includes a moiety that may be represented by the general formula:

in which R50 and R56 are as defined above.

[0044] The term “sulfamoyl” is art-recognized and refers to a moiety that may be represented by the general formula:

in which R50 and R51 are as defined above.

[0045] The term “sulfonyl” is art-recognized and refers to a moiety that may be represented by the general formula:

in which R58 is one of the following: hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl or heteroaryl.

[0046] The term “sulfoxido” is art-recognized and refers to a moiety that may be represented by the general formula:

in which R58 is defined above.

[0047] The term “phosphoryl” is art-recognized and may in general be represented by the formula:

wherein Q50 represents S or O, and R59 represents hydrogen, a lower alkyl or an aryl. When used to substitute, e.g., an alkyl, the phosphoryl group of the phosphorylalkyl may be represented by the general formulas:

wherein Q50 and R59, each independently, are defined above, and Q51 represents O, S or N.

When Q50 is S, the phosphoryl moiety is a “phosphorothioate”.

[0048] The term “phosphoramidite” is art-recognized and may be represented in the general formulas:

wherein Q51, R50, R51 and R59 are as defined above.

[0049] The term “phosphonamidite” is art-recognized and may be represented in the general formulas:

wherein Q51, R50, R51 and R59 are as defined above, and R60 represents a lower alkyl or an aryl.

[0050] Analogous substitutions may be made to alkenyl and alkynyl groups to produce, for example, aminoalkenyls, aminoalkynyls, amidoalkenyls, amidoalkynyls, iminoalkenyls, iminoalkynyls, thioalkenyls, thioalkynyls, carbonyl-substituted alkenyls or alkynyls. [0051] The definition of each expression, e.g. alkyl, m, n, and the like, when it occurs more than once in any structure, is intended to be independent of its definition elsewhere in the same structure.

[0052] The term “selenoalkyl” is art-recognized and refers to an alkyl group having a substituted seleno group attached thereto. Exemplary “selenoethers” which may be substituted on the alkyl are selected from one of -Se-alkyl, -Se-alkenyl, -Se-alkynyl, and — Se — (CH2)_m — R61, m and R61 being defined above.

[0053] The terms triflyl, tosyl, mesyl, and nonaflyl are art-recognized and refer to trifluoromethanesulfonyl, p-toluenesulfonyl, methanesulfonyl, and nonafluorobutanesulfonyl groups, respectively. The terms triflate, tosylate, mesylate, and nonaflate are art-recognized and refer to trifluoromethanesulfonate ester, p-toluenesulfonate ester, methanesulfonate ester, and nonafluorobutanesulfonate ester functional groups and molecules that contain said groups, respectively.

[0054] The abbreviations Me, Et, Ph, Tf, Nf, Ts, and Ms represent methyl, ethyl, phenyl, trifluoromethanesulfonyl, nonafluorobutanesulfonyl, p-toluenesulfonyl and methanesulfonyl, respectively. A more comprehensive list of the abbreviations utilized by organic chemists of ordinary skill in the art appears in the first issue of each volume of the Journal of Organic Chemistry, this list is typically presented in a table entitled Standard List of Abbreviations. [0055] Certain compounds contained in compositions described herein may exist in particular geometric or stereoisomeric forms. In addition, compounds may also be optically active. Contemplated herein are all such compounds, including cis- and trans-isomers, R- and S- enantiomers, diastereomers, (D)-isomers, (L)-isomers, the racemic mixtures thereof, and other mixtures thereof. Additional asymmetric carbon atoms may be present in a substituent such as an alkyl group. All such isomers, as well as mixtures thereof, are encompassed herein.

[0056] If, for instance, a particular enantiomer of a compound is desired, it may be prepared by asymmetric synthesis, or by derivation with a chiral auxiliary, where the resulting diastereomeric mixture is separated and the auxiliary group cleaved to provide the pure desired enantiomers. Alternatively, where the molecule contains a basic functional group, such as amino, or an acidic functional group, such as carboxyl, diastereomeric salts are formed with an appropriate optically-active acid or base, followed by resolution of the diastereomers thus formed by fractional crystallization or chromatographic means well known in the art, and subsequent recovery of the pure enantiomers.

[0057] It will be understood that “substitution” or “substituted with” includes the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound, e.g., which does not spontaneously undergo transformation such as by rearrangement, cyclization, elimination, or other reaction.

[0058] The term “substituted” is also contemplated to include all permissible substituents of organic compounds. In a broad aspect, the permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds. Illustrative substituents include, for example, those described herein above. The permissible substituents may be one or more and the same or different for appropriate organic compounds. Heteroatoms such as nitrogen may have hydrogen substituents and/or any permissible substituents of organic compounds described herein which satisfy the valences of the heteroatoms. Compounds are not intended to be limited in any manner by the permissible substituents of organic compounds.

[0059] The chemical elements are identified in accordance with the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 67th Ed., 1986-87, inside cover. [0060] The term “UV damage” as used herein refers to any sort of damage to the objects described herein (e.g., plants and/or plant parts (e.g., fruits and/or vegetables)) that is caused by ultraviolet light. In some embodiments, such damage can include wilting, discoloration, shrinking, spotting, and the like.

[0061] A “form that is naturally occurring” when referring to a compound means a compound that is in a form, e.g., a composition, in which it can be found naturally. For example, since resveratrol can be found in red wine, it is present in red wine in a form that is naturally occurring. A compound is not in a form that is naturally occurring if, e.g., the compound has been purified and separated from at least some of the other molecules that are found with the compound in nature.

[0062] A “naturally occurring compound” refers to a compound that can be found in nature, i.e., a compound that has not been designed by man. A naturally occurring compound may have been made by man or by nature. For example, resveratrol is a naturally occurring compound. A “non-naturally occurring compound” is a compound that is not known to exist in nature or that does not occur in nature.

[0063] The term “xenohormesis” as used herein refers to the phenomenon by which a stress signal(s) in a first organism is transmitted to a second organism in a process where the second organism employs the first organism as an energy source. Where xenohormesis occurs, the first organism is stressed in some manner, e.g., by caloric intake, substance intake, and/or environment. This stress may manifest in a number of different phenotypic ways, ranging from outward appearance (e.g., in some way deviating from a normal, wild-type appearance) or in other ways, e.g., by changes in genomic and/or proteomic profiles. Xenohormesis occurs when the second organism that employs the first organism as food (e.g., by eating the first organism) responds in some way to the stress phenotype of the first organism, e.g., by adopting a stressed phenotype itself. As such, xenohormesis can result in a stressed phenotype of a first organism being transmitted to a second organism when the second organism employs the first organism as food.

[0064] A “xenohormetic compound” as used herein is compound when ingested that can improve longevity and fitness of an organism by activating the organism's cellular or organismal stress and/or defense response.

[0065] A xenohormetic compound may be a "naturally occurring compound," i.e., a compound that can be found in nature, i.e., a compound that has not been designed by man. A naturally occurring compound may have been made by man or by nature. A xenohormetic compound may also be a "non- naturally occurring compound," i.e., a compound that is not known to exist in nature or that does not occur in nature. A xenohormetic compound may be in a "form that is naturally occurring, " i.e., in a form, e.g., a composition, in which it can be found naturally. For example, since resveratrol can be found in red wine, it is present in red wine in a form that is naturally occurring. A compound is not in a form that is naturally occurring if, e.g., the compound has been purified and separated from at least some of the other molecules that are found with the compound in nature

[0066] The term “stabilizing agent” refers to a compound that can improve the material properties, particularly water resistance and mechanical properties of the films formed from the coating composition.

I. Compositions

Cutin-Derived Monomers and Oligomers

[0067] The cells that form the aerial surface of most plants (such as higher plants) include an outer envelope or cuticle, which provides varying degrees of protection against water loss, oxidation, mechanical damage, photodegradation, and/or biotic stressors, depending upon the plant species and the plant organ (e.g., fruit, seeds, bark, flowers, leaves, stems, etc.). Cutin, which is a biopolyester derived from cellular lipids, forms the major structural component of the cuticle and serves to provide protection to the plant against environmental stressors (both abiotic and biotic). The thickness, density, as well as the composition of the cutin (i.e., the different types of monomers that form the cutin and their relative proportions) can vary by plant species, by plant organ within the same or different plant species, and by stage of plant maturity. This variation in the cutin composition as well as the thickness and density of the cutin layer between plant species and/or plant organs and/or a given plant at different stages of maturation can lead to varying degrees of resistance between plant species or plant organs to attack by environmental stressors (i.e., water loss, oxidation, mechanical injury, and light) and/or biotic stressors (e.g., fungi, bacteria, viruses, insects, etc.).

[0068] Methods of preparing cutin-derived monomers, oligomers, and/or combinations thereof from cutin-containing plant matter is known in the art, including in U.S. Pat. Nos.: 10,959,442; 11,160,287; 10,517,310; and 9,743,679 to Perez et al, and 11,028,030 to Bakus et al. which are hereby incorporated by reference in their entirety. The method can include thermally and/or mechanically and/or enzymatically and/or chemically treating plant matter to, at least partially, separate a cutin-containing portion from the plant matter. The plant matter can be subjected to elevated temperature and/or pressure in an aqueous medium (e.g., as in pressure cooking) to partially separate a cutin-containing portion from the plant matter. Alternatively, the plant matter may be subjected to lower temperatures (e.g., as in freezing) to partially separate a cutin-containing portion from the plant matter. In some methods, the plant matter is subjected to sonication in an aqueous medium to partially separate a cutin-containing portion from the plant matter. Optionally, the cutin-containing portion is heated in a mixture of ammonium oxalate and oxalic acid to aid separation of the cutin from the non-cutin-containing portion (i.e., the remainder of the cuticle and unwanted plant matter). Optionally, this separation can be achieved (or assisted) enzymatically using enzymes capable of hydrolyzing ester bonds and/or alternatively using enzymes capable of breaking down polysaccharides that comprise the non- cutin-containing portion of the plant. Optionally, the cutin-containing portion is refluxed in at least one organic solvent (such as chloroform and/or methanol) to remove residual waxes and/or any remaining soluble polar components from the cutin. Alternatively, removal of residual waxes and remaining soluble components can be achieved using supercritical CO2 or supercritical H2O. The cutin is then refluxed in a solvent having a high pH (e.g., in the range of about 10 to 14, and typically in the range of 12 to 14), for example a solvent in which metal alkoxide or metal hydroxide (or alternative source of alkoxide or hydroxide) is dissolved, to at least partially depolymerize the cutin and obtain an intermediate extract including a plurality of esterified or fatty acid cutin monomers, their oligomers, or mixtures thereof. In cases where the intermediate extract is obtained from (metal) alkoxide-mediated depolymerization, the pH of the intermediate extract is then adjusted to be in the range of about 6.5 to 9.0. In cases where the intermediate extract obtained from (metal) hydroxide-mediated depolymerization, the pH of the intermediate extract is then adjusted to be in the range of about 1.0 to 6.0. Alternatively, the cutin can be at least partially depolymerized under acidic conditions to obtain an intermediate extract including a plurality of fatty acid cutin monomers, oligomers, or mixtures thereof. The intermediate extract is then precipitated and/or extracted and purified (such as by washing with one or more selective solvents) to obtain the plant extract such that the plant extract is substantially free from accompanying plant-derived compounds. Further purification by chromatography or recrystallization in a selective solvent may also be carried out after washing to obtain the final extract.

[0069] The cutin-derived monomers, oligomers, and/or combinations thereof may comprise compounds of Formula (I), Formula (II), and/or Formula (III):

wherein for Formula (I):

R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, and R¹⁰ are each independently — H, — OR¹³, — NR¹³R¹⁴, —SR¹³, halogen, — Ci-C₆ alkyl, — Ci-C₆ alkenyl, — Ci-C₆ alkynyl, — C₃- C? cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹³, — NR¹³R¹⁴, — SR¹³, or halogen;

R¹³ and R¹⁴ are each independently — H, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, or — Ci- Ce alkynyl; R¹¹ is — H, — glyceryl, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, — C₁-C₆ alkynyl, — C₃- C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹³, — NR¹³R¹⁴, — SR¹³, or halogen;

R¹, R², R⁴ and R⁵ are each independently — H, — OR¹¹, — NR¹¹R¹², — SR¹¹, halogen, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, — C₁-C₆ alkynyl, — C3-C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹¹, — NRⁿR¹², — SR¹¹, or halogen;

R¹¹ and R¹² are each independently — H, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, or — Ci- Ce alkynyl; the symbol represents an optionally single or cis or trans double bond; the symbol = represents a cis or trans double bond;

R³ is — OH and R³ is selected from the group consisting of — H, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, — C₁-C₆ alkynyl, — C3-C7 cycloalkyl, and aryl when between R³ and R³ is a single bond, and R³ and R³ are absent when between R³ and R³ represents a double bond; n is an integer in the range of 0 to 11; m is an integer in the range of 0 to 25; and

0<m+n<25; wherein for Formula III:

R¹⁴ and R¹⁵ are each independently, at each occurrence, — H, — C₁-C₆ alkyl, — C2-C6 alkenyl, or — C2-C6 alkynyl; the symbol ~~ ~~ represents a single bond or a cis or trans double bond; the symbol = represents a cis or trans double bond; n is 0, 1, 2, 3, 4, 5, 6, 7 or 8; m is 0, 1, 2 or 3; q is 0, 1, 2, 3, 4 or 5; r is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and

R is selected from — H, — C₁-C₆ alkyl, — C2-C6 alkenyl, — C2-C6 alkynyl, — C3- C7 cycloalkyl, aryl, 1 -glyceryl, 2-glyceryl, or heteroaryl.

[0070] In some embodiments, the cutin-derived monomers, oligomers, or combinations thereof comprises compounds of Formula (I).

[0071] In some embodiments, the cutin-derived monomers, oligomers, or combinations thereof comprises compounds of Formula (II).

[0072] In some embodiments, the cutin-derived monomers, oligomers, or combinations thereof comprises compounds of Formula (III).

[0073] In some embodiments, the cutin-derived monomers, oligomers, or combinations thereof comprises a mixture of compounds of Formula (I), Formula (II), and/or Formula (III).

Xenohormetic Compounds

[0074] Not to be bound by any theory, xenohormesis is a hypothesis which essentially states that organisms have evolved to respond to chemical cues in their diet to gain advance warning of a deteriorating environment (Lamming et al., Small Molecules that Regulate Lifespan: Evidence for Xenohormesis. Mol Microbiol 53: 1003-9 (2004), which is hereby incorporated by reference in its entirety). Phytoalexins such as resveratrol are produced in plants in response to various stresses including injury, infection, and UV light (Langcake et al., The Production of Resveratrol by Vitis Vinifera and Other Members of the Vitaceae as a Response to Infection or Injury. Physiol Plant Pathol 9: 77-86 (1976); Adrian et al., Stilbene Content of Mature Vitis vinifera Berries in Response to UV-C Elicitation. J. Agric. Food Chem, 48(12): 6103-6105 (2000); Larronde et al., Airborne Methyl Jasmonate Induces Stilbene Accumulation in Leaves and Berries of Grapevine Plants. Am. J. Enol. Vitic. 54(1): 63-66 (2003); Schwekendiek et al., Pine Stilbene Synthase cDNA, a Tool for Probing Environmental Stress. FEBS Lett., 301 (l):41-4 (1992), which are hereby incorporated by reference in their entirety). Since these molecules increase when the food source is threatened, it is likely that animals eating these plants experience an increased exposure to these molecules before famine or other stresses, and that responding to their presence in the diet, rather than waiting for a direct stress, might confer an evolutionary advantage.

[0075] According to xenohormesis, stressed plants will form an abundant reservoir for medicinal compounds that may trigger part or all of the caloric restriction response. Studies on caloric restriction have thoroughly established that organisms, including mammals, are capable of entering a state of increased stress-resistance that improves health and survival when energy intake is low (McCay et al., Prolonging the Lifespan. Scientific Monthly 39: 405-414 (1934); Barger et al., The Retardation of Aging by Caloric Restriction: Its Significance in the Transgenic Era. Exp Gerontol 38: 1343-51 (2003), which are hereby incorporated by reference in their entirety). The beneficial effects of a variety of phytochemicals, many of them structurally related to resveratrol, are currently gaining the attention of the scientific community. Molecules such as catchetin, quercetin, and pterostilbene are beneficial alone and may have additive or even synergistic effects in combination with resveratrol.

[0076] Xenohormetic compounds include molecules that are produced in plants or fungi or products thereof, such as fruit, vegetables, flowers, and grains, in response to a stress condition. Stress may be any non-optimal condition for growth, development or reproduction, or a non- physiological condition, e.g., heat, dehydration, infection, starvation, irradiation, injury, excessive light, and cold, e.g., below freezing temperatures. A "stress condition" can also be exposure to heatshock; osmotic stress; a DNA damaging agent; inadequate salt level; inadequate nitrogen levels; inadequate nutrient level; radiation, e.g., an excess or lack of light, or a toxic compound, e.g., a toxin or chemical warfare agent (such as dirty bombs and other weapons that may be used in bio terrorism). "Inadequate levels" refer to levels that result in non-optimal condition for growth, development or reproduction.

[0077] Xenohormetic molecules modulate the activity of xenohormetic targets. For example, a xenohormetic molecule may inhibit the activity of a protein kinase, e.g., JAK2, Piml, Pirn 2, S6K, NLK, and Rsk2. A xenohormetic molecule may also stimulate the abundance or activity of other xenohormetic targets, such as a sirtuin, e.g., SIRT1 in humans.

[0078] Exemplary xenohormetic molecules include resveratrol, derivatives and analogs thereof, and any other molecule that increases the activity of a sirtuin, such as flavones, isoflavones, stilbenes, flavanones, isoflavanones, catechins, chaicones, tannins and anthocyanidins. Exemplary stilbenes include hydroxystilbenes, such as trihydroxystilbenes, e.g., 3,5,4'- trihydroxystilbene ("resveratrol"). Resveratrol is also known as 3,4',5-stilbenetriol.

[0079] Resveratrol is a naturally occurring phenolic micronutrient produced in select plant species such as grapes, berries, peanuts, and pines (Wagner, et al., Plant Physiol. Biochem., 171: 26-37 (2022), which is hereby incorporated by reference in its entirety). Exogenous application of trans -resveratrol on fruit has been shown to enhance the plants resistance to fungal pathogens, including B. cinerea, Phomopsis viticola, Plasmopara viticola, and Rhizopus stonifer (Urena, et al., J. Agric. Food Chem., 51(1): 82-89 (2003), which is hereby incorporated by reference in its entirety). The preservative properties of resveratrol are further demonstrated by Urena, who applied an aqueous coating of resveratrol to fruit (golden apples). Id. Even after storage of the fruit in ambient conditions for 75 days, the treated fruit displayed no external signs of decay, whereas the nontreated fruit had succumb to rot. Id. Similar results were found for the treatment of other fruit (e.g., tomatoes, grapes, avocadoes, pears, and peppers) with a resveratrol coating (Jimenez et al., J. Agric. Food Chem., 53(5): 1526-1530 (2005), which is hereby incorporated by reference in its entirety).

[0080] Furthermore, resveratrol has also been shown to stimulate the growth of lettuce (Lactuca saliva) (Wagner, et al., Plant Physiol. Biochem., 171: 26-37 (2022), which is hereby incorporated by reference in its entirety). The treated lettuce exhibited a reduction in the concentration of the superoxide anion (O2 ^_), and therefore, a decrease in oxidative damage normally experienced by the plant. Id. Overproduction of reactive oxygen species can inhibit photosynthesis in plants. Id. Thus, resveratrol’s reduction in superoxide concentrations is thought to induce a higher photosynthetic efficiency. Id.

[0081] Resveratrol is also thought to provide human health benefits including antioxidant, anticarcinogenic, antibacterial, anti-inflammatory properties. Id. These beneficial effects are linked to its ability to activate sirtuin-like protein deacetylases, redox-sensing enzymes involved in modulating metabolism regulation, stress responses, ageing processes, and longevity. Id. [0082] Other molecules that activate a sirtuin include tetrahydroxystilbenes, e.g., piceatarmol; hydroxy chalones including trihydroxy chalones, such as isoliquiritigenin, and tetrahydroxy chalones, such as butein; hydroxyflavones including tetrahydroxyflavones, such as fisetin; and pentahydroxy flavones, such as quercetin. Additional compounds include those described in U.S. Publication Nos. 2005/0096256 and 2005/0136537, and PCT Publication Nos. W005/002672 and W005/002555 to Sinclair et al., all of which are hereby incorporated by reference in their entirety.

[0083] In some embodiments of the present invention, the xenohormetic compounds are selected from the group consisting of flavones, isoflavones stilbenes, flavanones, isoflavones, catechins, chaicones, tannins, anthocyanidins, and combinations thereof.

Flavones, Flavanones, Isoflavones, and Isoflavanones

[0084] Flavone and its derivatives (often also collectively called “flavones”) are characterized by the following basic structure (substitution positions are given):

Some of important flavones which can also be found in living nature are given in the table below:

[0085] Exemplary flavones useful in the present invention include, but are not limited to, fisetin (3,7,3',4'-Tetrahydroxyflavone); quercetin (3,5,7,3',4'-Pentahydroxyflavone); 7, 8,3', 4'- Tetrahydroxy flavone; 3, 6, 2', 3 '-Tetrahydroxyflavone; 4'-Hydroxyflavone; 5,4'- Dihydroxyflavone; 5,7-Dihydroxyflavone; Morin (3,5,7,2',4'-Pentahydroxyflavone); Flavone; 5- Hydroxyflavone; Myricetin (3,5,7,3',4',5'-hexahydroxyflavone); 3, 7,3', 4', 5'- pentahydroxyflavone; 5,7,3',4',5'-pentahydroxyflavone; Gossypetin (3, 5, 7, 8, 3', 4'- hexahydroxyflavone); Luteolin (5,7,3',4'-Tetrahydroxyflavone); 3,6,3',4'-Tetrahydroxyflavone; 7,3',4',5'-Tetrahydroxyflavone; Kaempferol (3,5,7,4'-Tetrahydroxyflavone); 6-Hydroxyapigenin (5,6,7,4'-Tetrahydroxyflavone); Scutellarein (5,6,7,4’-Tetrahydroxyflavone); Apigenin (5,7,4'- Trihydroxyflavone); 3,6,2',4'-Tetrahydroxyflavone; 7,4’-Dihydroxyflavone, and combinations thereof. In some embodiments of the present invention, the xenohormetic compound is a flavone or derivative thereof.

[0086] Flavanones are characterized by the basic skeleton of the following structure:

Exemplary flavanones useful in the present invention include, but are not limited to, flavanone, hesperidin, naringenin, 3,5,7,3',4'-pentahydroxyflavanone, naringin, eriocitrin, taxifolin, and combinations thereof. In some embodiments of the present invention, the xenohormetic compound is a flavanone or derivative thereof.

[0087] Isoflavones and isoflavanone are characterized by the basic skeletons of the following structures:

Some isoflavones are able to mimic the effects of estrogen and modulate estrogen metabolism. As a result, isoflavones are known to reduce tumor cell proliferation, induce tumor cell apoptosis, regulate hormone balance, and reduce the risks of breast and prostate cancer, heart disease, osteoporosis, and several other diseases and conditions. Exemplary isoflavones and isoflavanones useful in the present invention include, but are not limited to, daidzein; daidzin; 6- O-malonyl daidzein; 6-O-acetyl daidzein; genistein; 6-O-malonyl genistein; 6-O-acetyl genistein; glycitein; 6-O-malonyl glycitein; 6-O-acetyl glycitein; Biochanin A; formononetin; irilone; prunetin; pratensein; glycitinn; dihydrodaidzein; equol; O-desmethylangolensin; daidzein 7,4'-di-O-sulfate; daidzein 7-0-beta-D-glucuronide; daidzein 4'-0-sulfate; 6,7,5'- trihydroxyisoflavone; 6,7,3',4'-tetrahydroxyisoflavone; 7,8,4'-trihydroxyisoflavone; 5, 6, 7, d'- tetrahydroxy isoflavone; dihydrogenistein; p-ethylphenol; 3', 4', 5, 7-tetrahydroxyisoflavone; genistein 4'-O-sulfate; genistein 7-O-beta-D-glucuronide; genistein 4'-O-sulfate; and 4',5,7- trihydroxyisoflavanone. In some embodiments of the present invention, the xenohormetic compound is an isoflavone, an isoflavanone, or a derivative thereof.

[0088] The compositions of the present invention may include one or more substituted or unsubstituted flavones, isoflavones, flavanones, and isoflavanones, or analogs thereof. Examples of flavones, flavanones, and isoflavanones are further described in U.S. Pat. No. 9,669,003 to Jin et al.; U.S. Pat. No. 4,013,801 to Dawson et al.; U.S. Pat. No. 3678044 to Adams; and PCT Publication Nos. W007/084861 to Sinclair et al.; WO12/141876 to Pan et al.; W008/003774 to Metz et al.; and W005/067915 to Holyoak et al., which are hereby incorporated by reference in their entirety.

Stilbenes, Catechins and Chaicones

[0089] Stilbenes are characterized by the basic skeleton of the following structure, where A represents a cis or trans carbon-carbon double bond:

Hydroxylated stilbenes are of particular interest, as are esters of hydroxylated stilbenes and/or ethers hydroxylated stilbenes. Some hydroxylated stilbenes are given in the table below:

Exemplary stilbenes useful in the present invention include, but are not limited to, resveratrol (3,5,4'-Trihydroxy-trans-stilbene), trans-stilbene, cis-stilbene, pterostilbene, piceatannol (3,5,3',4'-Tetrahydroxy-trans-stilbene), rhapontigenin, pinosylvin, rhapontin (3,3',5-Trihydroxy- 4'-methoxystilbene 3-O-P-D-glucoside), deoxyrhapontin (3,5-Dihydroxy-4'-methoxystilbene 3- O-P-D-glucoside); BML-230 (3,5-Dihydroxy-4’-thiomethyl-trans-stilbene); BML-217 (3,5- Dihydroxy-4'-chloro-trans-stilbene); pinosylvin (3,5-Dihydroxy-trans-stilbene); BML-225 (3,5- Dihydroxy-4'-ethyl-trans-stilbene); 3,5-Dimethoxy-4'-ethyl-trans-stilbene; BML-212 (3,5- Dihydroxy-4'-fluoro-trans-stilbene); BML-228 (3,5-Dihydroxy-4'-methyl-trans-stilbene); 3,5- Dimethoxy-4'-methyl-trans-stilbene; BML-232 (3,5-Dihydroxy-4'-azido-trans-stilbene); BML- 229 (3,5-Dihydroxy-4'-nitro-trans-stilbene); BML-231 (3,5-Dihydroxy-4'-isopropyl-trans- stilbene); BML-233 (3,5-Dihydroxy-4'-methoxy-trans-stilbene); rhapontin aglycone (3,5,3- Trihydroxy-4'-methoxy-trans-stilbene); BML-227 (3,4'-Dihydroxy-5-acetoxy-trans-stilbene); BML-221 (3,5-Dihydroxy-4'-acetoxy-trans-stilbene); 3,5-Dimethoxy-4'-acetoxy-trans-stilbene; BML-218 ((E)-l-(3,5-Dihydroxyphenyl)-2-(2-napthyl)ethene); BML-216 (3-Hydroxystilbene); BML-226 (3,5-Dimethoxy-4'-thiomethyl-trans-stilbene); BML-222 (3,5-Dihydroxy-4'- acetamide-trans-stilbene); BLM-215 (3,4-Dihydroxy-trans-stilbene); BML-224 ((E)-l-(3,5- Dihydroxyphenyl)-2-(cyclohexyl)ethene); 3,4-Dimethoxy-trans-stilbene; dihydroresveratrol (1- (3,5-Dihydroxyphenyl)-2-(4-hydroxyphenyl)ethane), and combinations thereof. In some embodiments of the present invention, the xenohormetic compound is a stilbene, or a derivative thereof. In some embodiments, the stilbene is selected from the group consisting of resveratrol, trans-stilbene, cis-stilbene, pterostilbene, piceatannol, rhapontigenin, pinosylvin, rhapontin, deoxyrhapontin, and combinations thereof.

[0090] Chaicones are characterized by the basic skeleton of the following structure:

Some common chaicones include unsubstituted chaicone (e.g., unsubstituted trans-chalcone), mono-hydroxy chaicones (e.g., 2'-hydroxy chaicone, 4'-hydroxy chaicone, etc.), di-hydroxy chaicones (e.g., 2',4-dihydroxy chaicone, 2 ',4 '-dihydroxy chaicone, 2,2'-dihydroxy chaicone, 2 ',3 -dihydroxy chaicone, 2',5'-dihydroxy chaicone, etc.), and tri-hydroxy chaicones (e.g., 2',3',4'-trihydroxy chaicone, 4,2',4'-trihydroxy chaicone, 2,2',4'-trihydroxy chaicone). Exemplary chaicones useful in the present invention include, but are not limited to, isoliquiritigenin (4,2',4'-Trihydroxychalcone), Butein (3,4,2',4'-Tetrahydroxychalcone); chaicone; 3,4,2'4'6'-Pentahydroxychalcone; and mixtures thereof. In some embodiments, the xenohormetic compound is a chaicone or a derivative thereof.

[0091] Catechins are characterized by the basic skeleton of the following structure:

Catechins are a group of compounds which generally regarded as hydrated flavones or anthocyanidines. Catechins form the base substance of a series of natural oligo- or polymeric tannins, e.g. in tea. They occur together with other phenols in many types of fruit and are involved in the browning, catalyzed by phenol oxidases, of areas which have been subjected to pressure or have been cut. Exemplary catechins useful in the present invention include, but are not limited to, (-)-Catechin (Hydroxy Sites: 3, 5, 7, 3', 4'); (+)-Catechin (Hydroxy Sites: 3, 5, 7, 3', 4'); catechin gallate (CG); (+)- and (-)-epicatechin (EC), (-)-Gallocatechin (Hydroxy Sites: 3, 5, 7, 3', 4', 5'); epigallocatechin (EGC); epigallocatechin-3 -gallate (EGCG); and combinations thereof. In some embodiments, the xenohormetic compound is a catechin or a derivative thereof.

[0092] Examples of stilbenes, catechins and chaicones are further described in U.S. Pat. No. 8,846,724 to Sinclair et al.; U.S. Pat. No. 9,610,258 to McWherter et al.; and PCT Publication No. W010/095943 to Van Der Beek et al., which are hereby incorporated by reference in their entirety.

Tannins

[0093] Tannins are water-soluble phenol derivatives naturally synthesized and accumulated by higher plants as secondary metabolic products (Krzyzowska et al., Tannic Acid Modification of Metal Nanoparticles: Possibility for New Antiviral Applications. Nanostructures for Oral Medicine, (2017), which is hereby incorporated by reference in its entirety). From a chemical point of view, tannins are polyphenols with molecular weights between 500 and 3000 Da. Id. Condensed tannins (CTs) are present in many plants and are oligomers or polymers of flavonoid (flavan-3-ol) units. CTs are also commonly termed proanthocyanidins due to the red anthocyanidins that are produced upon heating in acidic alcohol solutions. CTs may contain from 2 to 50 or more flavonoid units. CT polymers have complex structures due to variations in the flavonoid units and the sites for interflavan bonds.

[0094] Hydrolysable tannins are simple phenols, for example mixtures of pyrogallol and eragic acid, and mixtures of glycans and diglycines with sugars, such as esters of glucose.

Hydrolysable tannins and condensed tannins may be extracted from starting materials, including, for example, trees and / or shrubs, using well established processes. A more detailed discussion of tannins can be found in Handbook of Adhesive Technology , Second Edition, CRC Publishing, 2003, Chapter 27, "Natural Phenolic Adhesives I: Tannin," and Monomers, Polymers and Composites from Renewable Resources , Elsevier, "Tannins: Major Sources, Properties and Applications."

Anthocyanidins

[0095] Anthocyanidins and anthocyanins (anthocyanidins including sugar groups) are a large family of naturally occurring pigments. The color of most fruits, flowers and berries is determined by their content of anthocyanidins and anthocyanins. Anthocyanidines, the aglyconic component of anthocyanins, have a basic structure as shown below:

[0096] Typical examples include: cyanidin (hydroxylated at positions 3, 5, 7, 3', 4'), delphinidin (hydroxylated at positions 3, 5, 7, 4', 5') and pelargonidin (hydroxylated at positions 3, 5, 7, 3'). The hydroxyl groups are usually glycosylated (e.g., an anthocyanin) and/or methoxylated (e.g. malvidin is substituted at the 3' and 5' hydroxyl groups and paeonidin and petunidin are substituted at the 3' hydroxyl group). Anthocyanidins can include a counter ion such as Cl", Br“, or I-. In some embodiments, the anthocyanidin is selected from the group consisting of pelargonidin chloride, cyanidin chloride, delphinidin chloride, and combinations thereof. In some embodiments, the xenohormetic compound is an anthocyanidin or a derivative thereof. In some embodiments, the anthocyanidin is selected form the group consisting of pelargonidin chloride, cyanidin chloride, delphinidin chloride, and combinations thereof.

[0097] Anthocyanins are water-soluble glycosides of polyhydroxyl and polymethoxyl derivatives of 2-phenylbenzopyrylium or flavylium salts. Individual anthocyanins differ in the number of hydroxyl groups present in the molecule, the degree of methylation of these hydroxyl groups, the nature, number and location of sugars attached to the molecule and the number and the nature of aliphatic or aromatic acids attached to the sugars in the molecule. Hundreds of anthocyanins have been isolated and chemically characterized by spectrometric tools.

[0098] Anthocyanins share a basic carbon skeleton in which hydrogen, hydroxyl or methoxyl groups can be found in differing positions. In fruits and vegetables, six basic anthocyanin compounds predominate, differing both in the number of hydroxyl groups present on the carbon ring and in the degree of methylation of these hydroxyl groups. The identity, number and position of the sugars attached to the carbon skeleton are also variable; the most common sugars that can be linked to carbon-3, carbon-5 and, sometimes, carbon-7, are glucose, arabinose, rhamnose or galactose. On this basis, it is possible to distinguish monosides, biosides and triosides.

[0099] Anthocyanidins and anthocyanins are known in the art, and can be isolated from natural sources, produced using commercially available starting materials, or synthesized using known organic, inorganic and/or enzymatic processes, for example, as described in U.S. Pat. No. 8,987,481 to Gupta; U.S. Pat. No. 10,786,522 to Burgos et al.; and U.S. Pat. No. 8,449,927 to Eidenberger, which are hereby incorporated by reference in their entirety.

Polyphenol Flavonoids

[0100] Many of the above identified classes of xenohometic compounds are commonly grouped together as polyphenol flavonoids. Suitable polyphenol flavonoids for use in the compositions of the present invention include curcumin; quercetin; fisetin; rutin; quercitrin; catechin; gallocatechin; catechin 3-gallate; gallocatechin 3-gallate; epicatechin; epigallocatechin; epicatechin 3-gallate; epigallocatechin3-gallate; theaflavin-3 -gallate; theaflavin-3'-gallate; theaflavin-3, 3'-digallate; kaempferol; myricetin; galangin; isorhamnetin; pachypodol; rhamnazin; a pyranoflavonol; furanoflavonol; luteolin; resveratrol; apigenin; tangeritin; hesperetin; naringenin; eriodictyol; homoeriodictyol; analogs and derivatives thereof; as well as a combination of two or more thereof.

[0101] Flavonoids, analogs, and derivatives thereof are known in the art and commercially available (e.g., Biomol, Sigma/ Aldrich, Indofine). Alternatively, they can be produced using commercially available starting materials using known organic, inorganic and/or enzymatic processes, for example, as described in AU 201112012 and U.S. Pat. No. 9,241,916 to Sinclair et al., which are hereby incorporated by reference in their entirety.

Phytoalexins and Phytoanticipins

[0102] Xenohormetic molecules may also be any phytoalexins and phytoanticipins.

Exemplary compounds are set forth in Dixon, R.A., "Natural products and plant disease resistance," Nature 411 :843-847 (2001) and Grayer, RJ. and Harbome, J.B., "A Survey of Antifungal Compounds from Higher Plants, 1982-1993," Phytochemistry, 37:19-42 (1994). Exemplary phytoalexins may include, but are not limited to, 5-hexylcyclopenta-l, 3-dione, 5- octylcyclopenta-1 ,3-dione, 4,5-methylenedioxy-6-hydroxyaurone, dianthalexins, dianthramides, N-p-hydroxybenzoyl-5-hydroxyanthranilic acid, magnolol, safynol, dehydrosafynol, cichoralexin, mycosinol, scopoletin, ayapin, costunolide, lettucenin A, sesquiterpenes Al and A2, glyceollins II and III, spirobrassinin, cyclobrassinin, oxymethoxybrassinin, methoxybrassinin, brassinin, dioxy brassinin, brassicanals A-C, cyclobrassinin sulphoxide, brassilexin, camalexin, methoxycamalexin, dihydropinosylvin, demethylbatatasin IV, batatasin IV, scopoletin, momilactones A and B, oryzalexins A-E, oryzalexin S, piceatannol, luteolinidin, apigenmidin 5- caffeylarabinoside, HDDBOA glucoside, medicarpin, isoneorautenol, demethylmedicarpin, desmocarpin, kievitone, diphysolone, ferrerein, nissicacpin, fruticarpin, nissolicarpin, furanodihydrokaempferol, dalbergiodin, phaseollidin, yerenolide, hemigossypol, sanguinarine, benzoic acid, aucuparin, T- and 4'-methoxyaucuparin, a- and P-cotonefuran, eriobofuran, a-, -, and y-pyrufuran, rhaphiolepsin, 2',6'-dihydroxyl-4'- methoxyacetophenone, puipurin 1 -methyl ether, seselin, scoparone, acteoside, galactosylacteoside, 7- hydroxycalamenene, mansonones A-F, psoralen, and bergapten. Other exemplary compounds may include, but are not limited to, sesquiterpene (rishitin, Nicotiana tabacum), diterpene (momilactone A, Oryza saliva), furanoacetylene (wyerone, Viciafaba), flavanone (sakuranetin, Oryza sativa), aurone {Cephalocereus senilis), pterocarpan (maackianin, Cicer arietinum), pterocarpan (medicarpin, Medicago sativa), biphenyl (aucuparin, Malus pumila), benzofuran (Cotoneaster spp.), benzophenanthridine alkaloid (sanguainarine, Papaver bracteatum), benzylisoquinoline alkaloid (berberine, Berberis spp.), indole (camalexin, Arabidopsis thaliana), indole (brassilexin, Brassica spp.), anthranilamide {Dianthus caryophyllus), and elemental sulphur (Theobroma cacao). Xenohormetic molecules may also include derivatives and analogs of these compounds.

[0103] Additional exemplary xenohormetic molecules include: Hinokitiol (b-Thujaplicin; 2- hydroxy-4-isopropyl-2,4,6-cycloheptatrien-l-one); L-(+)-Ergothioneine ((S)-a-Carboxy-2,3- dihydro-N,N,N-trimethyl-2-thioxo-lH-imidazole-4-ethanaminium inner salt); Caffeic Acid Phenyl Ester; MCI-186 (3 -Methyl- l-phenyl-2-pyrazolin-5 -one); HBED (N,N'-Di-(2- hydroxybenzyl)ethylenediamine-N,N'-diacetic acid»HCI»H2O); Ambroxol (trans-4-(2-Amino- 3, 5 -dibromobenzylamino) cyclohexane»HCl); U-83836E ((-)-2-((4-(2,6-di-l-Pyrrolidinyl-4- pyrimidinyl)-l-piperazinyl)methyl)-3,4-dihydro-2,5,7,8-tetramethyl-2H-l-benzopyran-6- ol»2HCI); Dipyridamole; Nicotinamide; ZM 336372 (3-(dimethylamino)-N-(3-(4- hydroxybenzamido)-4-methylphenyl)benzamide); Camptothecin; Coumestrol;

Nordihydroguaiaretic acid (NDGA); Esculetin; 2-[l-(2-hydroxyphenyl) ethylidene]hydrazine-l- carbothioamide; prop-2-ynyl 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylate; 4-{3- [(3,5-dichloro-2-hydroxybenzylidene)amino]propyl}-4,5-dihydro-lH-pyrazol-5-one; 6- (phenylthio)-2-[2-(2-pyridyl)ethyl]-2,3-dihydro-lH-benzo[de]isoquinoline-l, 3-dione; 5-[(4- chloroanilino)methylene]-3-(4-chlorophenyl)-l lambda-6-, 3-thiazolane-l, 1,4-trione; and 2-(4- chlorophenyI)-7-methylimidazo[l,2-a]pyridine-3-carbaldehyde O-(3-fluorobenzyl)oxime.

[0104] In some embodiments, the xenohormetic compound is a mixture of xenohormetic compounds comprising one or more flavone, flavanone, isoflavone, isoflavanone, stilbene, catechin, chaicone, tannin, anthocyanidin, polyphenol, or a derivative thereof. In some embodiments, the mixture of xenohormetic compounds comprises two or more of flavones, isoflavones stilbenes, flavanones, isoflavones, catechins, chaicones, tannins, and/or anthocyanidins. For example the mixture may comprise stilbenes and flavones; stilbenes and isoflavones; stilbenes and flavanones; stilbenes and isoflavanones; stilbenes and catechins; stilbenes and chaicones, stilbenes and tannins; stilbenes and anthocyanidins; flavones and isoflavones; flavones and flavanones; flavones and isoflavanones; flavones and catechins; flavones and chaicones, flavones and tannins; flavones and anthocyanidins; flavanones and isoflavone; flavanones and isoflavanones; flavanones and catechins; flavanones and chaicones; flavanones and tannins; flavanones and anthocyanidins; isoflavones and isoflavanones; isoflavones and catechins; isoflavones and chaicones, isoflavones and tannins; isoflavones and anthocyanidins; isoflavanones and catechins; isoflavanones and chaicones, isoflavanones and tannins; isoflavanones and anthocyanidins; catechins and chaicones, catechins and tannins; catechins and anthocyanidins; chaicones and tannins; chaicones and anthocyanidins; or tannins and anthocyanidins. In some embodiments, the mixture of xenohormetic compounds comprises three or more of flavones, isoflavones stilbenes, flavanones, isoflavones, catechins, chaicones, tannins, and/or anthocyanidins. In some embodiments, the mixture of xenohormetic compounds comprises four or more of flavones, isoflavones stilbenes, flavanones, isoflavones, catechins, chaicones, tannins, and/or anthocyanidins. In some embodiments, the mixture of xenohormetic compounds comprises stilbenes and flavones. In some embodiments, the mixture of xenohormetic compounds comprises resveratrol, quercetin and fisetin.

[0105] In some embodiments, the cutin-derived monomers, oligomers, or combinations thereof are chemically bonded to the polyphenolic or xenohormetic compounds or derivatives.

Nicotinamide Adenine Dinucleotide Increasing Compounds

[0106] In certain embodiments, the compositions of the present invention include one or more nicotinamide adenine dinucleotide increasing compounds. Nicotinamide adenine dinucleotide (NAD) is an enzyme co-factor that is essential for the function of several enzymes related to reduction-oxidation reactions and energy metabolism. NAD+ functions as an electron carrier in the energy metabolism of amino acids, fatty acids and carbohydrates (Bogan & Brenner, 2008). NAD+ is critical for redox reactions and as a substrate for signaling by the PARPs (poly adenoside diphophosphate-ribose polymerases) and the sirtuins (SIRT1 to SIRT7), in the regulation of DNA repair, energy metabolism, cell survival, and circadian rhythms (Bronkowski, M.S. & Sinclair, D., Nat. Rev. Mole. Cell Bio., 17, 679-690, 2016)). Raising NAD+ concentrations delays aging in yeast, files and mice (Mouchiroud et al. Cell 154, 464- 471, 2014). It has recently also been demonstrated that NAD+ directly regulates protein- protein interactions, the modulation of which may protect against cancer and radiation exposure as well as having a direct impact on aging (Li et al., Science 355, 1312-1317, 2017). Increasing bodies of evidence support the idea that interventions using NAD+ intermediates, such as NMN and NR, can restore the available NAD+.

[0107] The classic role of NAD⁺ is a co-enzyme that catalyzes cellular redox reactions, becoming reduced to NADH, in many fundamental metabolic processes. There are five major precursors and intermediates to synthesize NAD+: tryptophan, nicotinamide, nicotinic acid (NA), nicotinamide riboside (NR), and nicotinamide mononucleotide (NMN). NAD can be synthesized de novo by the conversion of the amino acid tryptophan through multiple enzymatic steps to nicotinic acid mononucleotide (NaMN). NaMN is converted to nicotinic acid dinucleotide (NaAD+) by NMN/NaMN adenylyltransferases (NMNATs) and then amidated to NAD+ by NAD+ synthetase. In some embodiments, the nicotinamide adenine dinucleotide increasing compound is selected from the group consisting of Nicotinamide ribose (NR), nicotinic acid riboside (NaR), ester derivatives of nicotinic acid riboside, nicotinic acid (niacin), ester derivatives of nicotinic acid, Nicotinic mononucleotide (NMN), Nicotinic acid mononucleotide (NaMN), nicotinic acid dinucleotide (NaAD+), ester derivatives of nicotinic acid mononucleotide, nicotinic acid adenine dinucleotide (NaAD), nicotinic acid adenine dinucleotide (NAAD), and combinations thereof. In some embodiments the nicotinamide adenine dinucleotide increasing compound is nicotinic acid riboside.

[0108] NAD+ precursors and derivatives thereof are known in the art and can be produced using commercially available starting materials or synthesized using known organic, inorganic and/or enzymatic processes, for example, as described in U.S Pat. No. 8,106,184 to Sauve et al.; US Patent No. 10,654,883 to Wathier et al.; U.S. Pat. No. 10,183,036 to Dellinger et al.; PCT Publication Nos. WO19/221813, WO19/222368, WO20/028682, WO20/028684, WO19/222360, and WO19/226755 Wathier et al., as well as PCT Publication No. WO19/023748 to Wu et al., which are hereby incorporated by reference in their entirety. Emulsifiers and Solubilizers

[0109] Many flavonoids are poorly soluble in water and other solvents suitable for pharmaceutical, nutraceutical (fortified foods and dietary supplements), cosmeceutical and food applications. Emulsifiers and solubilizer (also referred to as surfactants) can be used to increase the solubility of the compositions herein. In certain embodiments, the compositions of the present invention include one or more emulsifier and/or solubilizer. Examples of solubilizers include, but are not limited to, fatty acids, fatty acid esters or amides or ether analogs, or hydrophilic derivatives thereof, including, for example, oleic acid and/or olive oil dried powder. [0110] The emulsifier may be an edible emulsifier selected from non-ionic emulsifier, anionic emulsifier, and mixtures thereof. The emulsifier may allow the composition to be in liquid form at room temperature and/or to increase the solubility of the composition in a solvent (e.g., water). The emulsifier can additionally serve as a pH modifier of the composition. Nonlimiting examples of suitable emulsifiers include morpholine, ammonia, lecithin, ethylene glycol monostearate, ammonium lauryl sulfate, sodium steroyl-2-lactylate, potassium oleate, propylene glycol monostearate, sodium alkyl sulfate, polyglycol, polysorbate surfactants (or TWEEN surfactants), e.g., polyoxyethylene (20) sorbitan monolaurate, also referred to as “TWEEN 20,” or polyoxyethylene (80) sorbitan monolaurate, also referred to as “Tween 80”; sorbitan surfactants (or SPAN surfactants), e.g., sorbitan monolaurate, also referred to as “SPAN 20,” or sorbitan monooleate, also referred to as “SPAN 80”; and combinations thereof.

[0111] In some embodiments, the emulsifier may be present in the composition in an amount ranging from about 0.01 wt% to 15 wt%, from about 0.1 wt% to 10 wt%, from about 0.1 wt% to 5 wt%, or from about 0.1 wt% to 3 wt%. The amount of emulsifier may be less than 2 wt% of the total composition. In some embodiments, the emulsifier is present at a concentration ranging from 0.01 wt%, 0.1 wt%, 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, or 10 wt% up to 0.1 wt%, 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 10 wt%, or 15 wt%.

[0112] The use of emulsifiers in edible coating compositions is known in the art, including for example, U.S. Pat. No. 11,046,858 to Zhao et al.; U.S. Pat. No. 9,648,890 to Nussinovitch et al.; US Pat. No. 1,943,468 to Bridgeman et al.; U.S. Pat. No. 2,213,557 to Tisdale et al.; PCT Publication No. WO11/084759 to Elejalde et al; and PCT Publication No. W004/083310 to Hassan et al., which are hereby incorporated by reference in their entirety.

UV-Inhibiting Compounds

[0113] Exposure to high levels of UV light can damage produce creating visibly damaged and discolored tissues, destroying native healthful phytochemical compounds, stimulating production of undesirable and harmful compounds like ethylene gas, and providing a foothold for spoilage organisms to grow. Such produce suffers a loss of perceived quality, reduced health benefits and is generally deemed unsuitable for the fresh market. In certain embodiments, the compositions of the present invention include one or more UV-inhibiting compounds.

Stabilizing Agents

[0114] Stabilizing agents can be added to the composition to improve the material properties, particularly mechanical properties of the films/coatings formed from the composition of the present invention. In certain embodiments, the compositions of the present invention include one or more stabilizing agents. The stabilizing agent may be a natural stabilizing agent, such as a plant-derived leachate. For example, tragacanth, karaya and acacia gum; and extracts such as carrageenan, locust bean gum, guar gum and pectin; or pure culture fermentation products such as xanthan gum may all be useful in the present invention. Chemically, these materials are all salts of complex anionic polysaccharides. Applicable synthetic natural-based stabilizing agents are cellulose derivatives that provide a family of substances in which free hydroxyl groups on a linear anhydroglucose polymer are etherified or esterified and dissolve in water to provide a viscous solution. This group of materials includes alkyl and hydroxyl alkyl celluloses, specifically methyl cellulose, hydroxyethyl methyl cellulose, hydroxypropyl methyl cellulose, hydroxybutyl methyl cellulose, hydroxyethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose and carboxymethyl cellulose. Another group of stabilizing agents include polyacrylates such as patented Acusol thickeners (eg, Acusol 823, Rohm and Haas, Philadelphia, PA, USA), and Carbopol thickeners such as Carbopol 934, or Carbopol Aqua-30 Polymer (BF Goodrich, Cleveland, Ohio, USA). Other potential stabilizing agents that may be used include dextrin, corn starch and hydrous magnesium silicates such as Laponite XLG (Southern Clay Products, Inc., Gonzales, Texas, USA).

[0115] Stabilizing agents can be used at concentrations ranging from 0.1 wt% up to about 30 wt% (e.g., from 0.1 wt% up to about 20 wt%, from 0.1 wt% up to about 10 wt%, from 0.1 wt% up to about 5 wt%, or from 0.1 wt% up to about 3 wt%) of the composition. In some embodiments, the stabilizing agent is present at a concentration ranging from 0.1 wt%, 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt%, or 25 wt% up to 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, or 30 wt%. In some embodiments, the stabilizing agent is present at a concentration ranging from 0.1 wt% up to 5 wt% (e.g., 0.1 wt%, 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt% or 5 wt%). It is also possible to utilize a mixture of stabilizing agents in the compositions of the invention. Crosslinking Agents

[0116] The compositions of the present invention may include one or more crosslinking agents. The use of cross-linking agents in the coating compositions can impart improvements to the mechanical coating properties such as tack, mechanical strength (e.g., durability) and coating solubility. Cross-linked film and coating are generally mechanically much stronger than their non-crosslinked counterparts. Furthermore, crosslinking may reduce any stickiness and can help prevent soil and microorganisms from physically adhering to the coating, which may be desirable for some applications. The degree of crosslinking may be adjusted to achieve the desired combination of properties.

[0117] The concentration of the cross-linking agent in the composition can range from zero to an upper limit determined by the stability limit of the formulation (i.e., where precipitation begins to occur, or the resulting coating cannot be efficiently applied). The preferred crosslinker concentration can vary depending on the type of crosslinker used, but it is typically less than 25 wt% of the composition. The crosslinker concentration may be less than 10 wt%, less than 5 wt%, less than 3 wt%, less than 2 wt%, less than 1 wt%, less than 0.5 wt%, or less than 0.1 wt% of the composition. In some embodiments, the crosslinker is present in a concentration ranging from 0.1 wt%, 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, or 19 wt%, up to 0.5 wt%, 1 wt%, 2 wt%, 3 wt%, 4 wt%, 5 wt%, 6 wt%, 7 wt%, 8 wt%, 9 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, 19 wt%, or 20 wt%.

[0118] Examples of the crosslinking agents that may be utilized in the inventive compositions include, but are not limited to, phenolics, acids, metal ions, and combinations thereof. In other embodiments, the crosslinking agent can be an inorganic crosslinking agent, such as sodium trimetaphosphate, calcium acetate, calcium chloride, zinc chloride, magnesium chloride, ferric chloride, manganese, and the like. Organic crosslinking agents may also be used, such as polysaccharides, pyruvic acid, glutaraldehyde, glyceraldehyde, formaldehyde, magnesium and zinc salts of acetic acid, or combinations thereof.

[0119] Examples of phenolic compounds that can be used include, but are not limited to, tannic acid, salicylic acid, vanillin, ethyl vanillin, gallic acid, ellagic acid, methyl parabens, propyl parabens, ethyl parabens, butyl parabens, vanillin, butylated hydroxyanisole, butylated hydroxytoluene, tocopherols, a-tocopherol, and the like.

[0120] Examples of suitable acids include, but are not limited to, formic acid, citric acid, acetic acid, fumaric acid, lactic acid, malic acid, phosphoric acid, tartaric acid, propionic acid, and the like. In some embodiments, the acid compound may be the same as a stabilizing agent disclosed herein.

Compositions

[0121] In some embodiments, the composition includes one or more UV inhibitor, emulsifier, solubilizer, stabilizing agent, crosslinking agent, and combinations thereof. The composition of the present invention may further contain additional substances selected from the group consisting of antifoaming agents, preservatives, adhesive agents, plasticizers and agents reducing surface tension. Exemplary substances of these types are known in the art and include, but are not limited to, polydimethylsiloxane (PDMS), potassium carbonate, sodium bisulfite, sodium benzoate, sodium propionate, calcium propionate, benzoic acid, potassium sorbate, polyethylene glycol, glycerol, propylene glycol, sorbitol, mannitol, and rapeseed oil high in laurate (laurical ™).

[0122] In humans, the combination of resveratrol and quercetin is degraded slower than resveratrol or quercetin individually. The mixture of different xenohormetic compounds may be beneficial and improve the stability and effectiveness of the composition. For example, the use of a mixture of resveratrol, quercetin, and fisetin may produce a coating with improved properties when compared to a mixture comprising only resveratrol.

[0123] Without wishing to be bound by theory, the compositions and conjugates of the present invention are an improvement over the coatings of the prior art as the cutin protects and slow releases the xenohormetic compounds into the plant and/or plant part (e.g., produce). The xenohormetic compound in turn may protect the cutin from oxidation and degradation due to their antioxidant activity. The coating stops the xenohormetic compounds form oxidizing or otherwise degrading, acting as a slow release delivery system of the xenohormetic compounds to the plant and/or plant part. This slow release of the xenohormetic compounds further protects and extends the shelf-life of the coated plant and/or plant part (e.g., produce).

II. Methods of Making the Compositions

[0124] A further aspect of the present invention relates to a method of preparing a composition of xenohormetic compounds and cutin-derived monomers, oligomers, or combinations thereof. The method includes providing cutin-derived monomers, oligomers, or combinations thereof; providing xenohormetic compounds; and combining the xenohormetic compounds and cutin-derived monomers, oligomers, or combinations thereof in a solvent to form a first mixture.

[0125] In some embodiments, the ratio of cutin-derived monomers, oligomers, and combinations thereof and the xenohormetic compounds or derivatives thereof ranges from 10:90 wt ratio to 90:10 wt ratio. For example, the ratio of the cutin-derived monomers, oligomers, and combinations thereof and the xenohormetic compounds or derivatives thereof may be about 10:90 wt ratio, about 20:80 wt ratio, about 30:70 wt ratio, about 40:60 wt ratio, about 50:50 wt ratio (i.e., about 1:1 wt ratio), about 60:40 wt ratio, about 70:30 wt ratio, about 80:20 wt ratio, or about 90:10 wt ratio. In some embodiments, the ratio of cutin-derived monomers, oligomers, and combinations thereof and the xenohormetic compounds or derivatives thereof is about 1 : 1 wt ratio. When the compositions include a nicotinamide adenine dinucleotide increasing compound, the ratio of cutin-derived monomers, oligomers, and combinations thereof to the xenohormetic compounds or derivatives thereof to nicotinamide adenine dinucleotide increasing compound may be about 1:1:1 wt ratio.

[0126] In some embodiments, the compositions described herein include a solvent. Exemplary solvents include, but are not limited to, water, ethanol, and combinations thereof. In some embodiments, the cutin-derived monomers, oligomers, and combinations thereof and the xenohormetic compounds or derivatives are present in a centration ranging from about 0.1 mg/mL to 100 mg/mL.

[0127] In some embodiments, the xenohormetic compounds or derivatives are present in the composition ranging in concentration from about IxlO^-5 M to IxlO^-3 M. In some embodiments, the xenohormetic compounds or derivatives are present in the composition ranging in

III. Xenhormetin Conjugates

Conjugate structure

[0128] Another aspect of the present invention relates to a xenhormetin conjugate of Formula (IV) for coating or forming a film on a plant and/or plant part:

wherein:

Q is a xenhormetin moiety;

X is O, or N; R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², and R¹³ are independently selected at each occurrence from — H, —OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, halogen, — Ci-C₆ alkyl, — C₂-C₆ alkenyl, — C₂- Ce alkynyl, — C3-C7 cycloalkyl, aryl, and heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen;

R¹⁴ and R¹⁵ are independently selected at each occurrence from — H, — C₁-C₆ alkyl, — C₂-Ce alkenyl, and — C₂-Ce alkynyl;

= represents a single bond or a cis or trans double bond; a is 0 or 1 ;

g

[0129] In some embodiments of the xenhormetin conjugate, Q is a moiety selected from the group consisting of flavones, isoflavones, stilbenes, flavanones, isoflavanones, catechins, chaicones, tannins, and anthocyanidins.

[0130] In some embodiments of the xenhormetin conjugate, Q is a stilbene or chaicone moiety of Formula (V):

wherein

Ri, R2, R3, R4, Rs, R'i, R'2, R'3, R'4, and R'5 are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of Ri, R2, R3, R4, Rs, R'i, R'2, R'3, R'4, or R's comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

M represents O, NR, or S;

A-B represents a bivalent alkyl, alkenyl, alkynyl, amido, sulfonamide, diazo, ether, alkylamino, alkylsulfide, hydroxylamine, or hydrazine group; and n is 0 or 1.

[0131] In some embodiments of the xenhormetin conjugate, Q is a flavanone moiety of Formula (VI):

wherein

Ri, R2, R3, R4, R'i, R'2, R'3, R'4, R's and R" are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of Ri, R2, R3, R4, R'i, R'2, R'3, R'4, R's or R" comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

M represents H2, O, NR, or S;

Z represents CR, O, NR, or S;

X represents CR or N; and

Y represents CR or N.

[0132] In some embodiments of the xenhormetin conjugate, Q is an isoflavanone moiety of Formula (VII):

wherein

Ri, R2, R3, R4, R'i, R'2, R'3, R'4, R'5 and R"i are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of Ri, R2, R3, R4, R'I, R'2, R'3, R'4, R's or R"i comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

M represents H2, O, NR, or S;

Z represents C(R)2, O, NR, or S;

X represents CR or N; and

Y represents CR or N.

[0133] In some embodiments of the xenhormetin conjugate, Q is a flavone moiety of Formula (VIII):

wherein

Ri, R2, R3, R4, R'i, R'2, R'3, R'4, and R'5 are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of Ri, R2, R3, R4, R'i, R'2, R'3, R'4, or R'5 comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl; R" is H, alkyl, aryl, heteroaryl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, or carboxyl;

M represents H2, O, NR, or S;

Z represents CR, O, NR, or S; and

X represents CR" or N.

[0134] In some embodiments of the xenhormetin conjugate, Q is an isoflavone moiety of Formula (IX):

wherein

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

R" is H, alkyl, aryl, heteroaryl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, or carboxyl;

M represents H2, O, NR, or S;

Z represents C(R)2, O, NR, or S; and

Y represents CR" or N.

[0135] In some embodiments of the xenhormetin conjugate, Q is an anthocyanidin moiety of Formula (X):

wherein

R3, R4, Rs, Re, R7, Rs, R'2, R'3, R'4, R's, and R'e are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of R3, R4, Rs, Re, R7, Rs, R'2, R'3, R'4, R's, or R'e comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl; and

A- represents an anion selected from the following: Cl", Br“, or I-.

[0136] Without being bound by theory, the conjugates of Formula (IV) when used as a coating for a plant and/or plant part can act as a slow release delivery system of the xenohormetic compounds to the plant and/or plant part. The ester and/or ether bond connecting the xenohormetic moiety to the cutin derived monomer and/or oligomer can be cleaved through oxidative process to release the xenohormetic compound, which is then absorbed by the plant and/or plant part. The oxidative cleavage of the xenohormetic compound not only protects the plant and/or plant part by reacting with the oxidative stressor, but also by slowly releasing xenohormetic compounds to the plant and/or plant part.

Reactions

[0137] A further aspect of the present invention relates to a method of forming a xenhormetin conjugate of Formula (IV): wherein:

Q is a xenhormetin moiety;

X is O, or N; R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², and R¹³ are independently selected at each occurrence from — H, — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, halogen, — C1-C6 alkyl, — C2- C6 alkenyl, — C2-C6 alkynyl, — C3-C7 cycloalkyl, aryl, and heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen;

R³, R⁴, R⁷, and R⁸ are independently selected at each occurrence from — H, — OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, halogen, — Ci-C₆ alkyl, — C₂-C₆ alkenyl, — C₂-C₆ alkenyl, — C2-C6 alkynyl, — C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen; or

R¹⁴ and R¹⁵ are independently selected at each occurrence from — H, — Ci-

Ce alkyl, — C2-C6 alkenyl, and — C2-C6 alkynyl;

= represents a single bond or a cis or trans double bond; a is 0 or 1 ; b is 0, 1, 2, 3, 4, 5, 6, 7 or 8; c is 0 or 1 , d is 0, 1, 2 or 3; e is 0 or 1 ; f is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and g is 0, 1, 2, 3, 4 or 5.

The method includes: providing a xenohormetin compound; obtaining cutin from cutin-containing plant matter; adding the xenohormetin compound and cutin to a solvent to form a first mixture, the solvent having a boiling point at a first temperature at a pressure of one atmosphere; and heating the first mixture to a second temperature and second pressure, the second temperature being higher than the first temperature and the second pressure being higher than one atmosphere, to form a second mixture comprising the xenohormetin-conjugate of formula (IV). In some embodiments, the solvent is a nucleophilic solvent (e.g., water, glycerol, methanol, and ethanol), liquid CO2, supercritical CO2, or combinations thereof. In some embodiments, the solvent is a non-nucleophilic solvent. In some embodiments, the first temperature may be sufficient to dissolve the cutin and/or the xenohormetin compound. For example, the first temperature may range from 15 °C to 50°C.

[0138] In some embodiments, the second pressure is sufficiently high to maintain at least a portion of the solvent in a liquid phase at the second temperature. In some embodiments, the second pressure may range from about 5 atm up to about 1000 atm. In some embodiments, the second pressure may be about 5 atm, about 10 atm, about 20 atm, about 30 atm, about 40 atm, about 50 atm, about 60 atm, about 70 atm, about 80 atm, about 90 atm, about 100 atm, about 110 atm, about 120 atm, about 130 atm, about 140 atm, about 150 atm, about 160 atm, about 170 atm, about 180 atm, about 190 atm, about 200 atm, about 250 atm, about 300 atm, about 350 atm, about 400 atm, about 450 atm, about 500 atm, about 550 atm, about 600 atm, about 650 atm, about 700 atm, about 750 atm, about 800 atm, about 850 atm, about 900 atm, about 950 atm, or about 1000 atm.

[0139] In some embodiments, the second temperature is lower than 85 °C. For example, the second temperature may range from about 45°C to about 85°C. In some embodiments, the method is run in low light (e.g., 5 lumens per sq ft up to 70 lumens per sq ft).

[0140] In some embodiments, the cutin from cutin-containing plant matter comprises compounds of Formula (I) and/or Formula (II), and/or Formula (III) as described above.

[0141] The xenhormetin conjugates of the invention may be formed via known reaction conditions to form esters and/or ethers. For example, in one embodiment of the method of the invention, a carboxylic acid from the cutin-derived monomers, oligomers, or combinations thereof may be reacted with an alcohol (e.g., an alcohol of a xenohormetic compound, or derivative thereof) and, optionally, an acid to form esters.

[0142] A proven and widely used method for the preparation of esters is the condensation of carboxylic acids with alcohols in the presence of a catalyst. It is known that esterification can be carried out autocatalytically or with catalysis, for example by Brpnsted acids or by Lewis acids. Processes of this type are described in Lorz et al., “Phthalic Acid and Derivatives,” Ullmann's Encyclopedia of Industrial Chemistry, p 131-180 (2007), which is hereby incorporated by reference in its entirety.

[0143] In the process of esterification, the reaction mixture including the carboxylic acid (e.g., from the cutin-derived monomers and/or oligomers) and alcohol (e.g., from a xenohormetic compound) is usually heated for several hours and the water that is formed is removed. Methods are also known in which the esterification is carried out in a closed system under pressure and high temperatures. For example, WO 2007/126166 discloses a conventionally thermal esterification of fatty acids with alcohols at temperatures ranging from 200 to 350° C and pressures of up to 10 bar. Water formed during the reaction is continuously removed with excess alcohol. Some examples of the formation of esters from carboxylic acids are disclosed in U.S. Pat. Nos.: 10,106,486 to Keller et al.; 7,186,856 to Meng et al.; and 8,293,935 to Orjueal et al, which are hereby incorporated by reference in their entirety. A further example of esters formed from the condensation reaction of carboxylic acids with alcohols is disclosed in Amore et al., Macromol. Rapid Commim, 28(4):473-477 (2007), which is hereby incorporated by reference in its entirety. Amore teaches a microwave-assisted method for producing propionic esters, in which the esterification is completed by water removal.

[0144] Alternatively, the carboxylic acids of the cutin-derived monomers and/or oligomers may be converted to an acid chloride prior to reacting with the xenohormetic compound to form an ester linkage. This may be accomplished by reacting the carboxylic acid of the cutin-derived monomers and/or oligomers with thionyl chloride, oxalyl chloride, phosphorus oxychloride, etc., in an inert solvent such as toluene or dichloromethane in the presence of a catalytic amount of N,N-dimethylformamide. Thereafter, the acid chloride or active ester may be reacted with the xenohormetic compound. As for the method of activating carboxylic acid, examples thereof include a method of converting into an acid chloride by treatment with thionyl chloride, oxalyl chloride, phosphorus oxychloride, etc., in an inert solvent such as toluene or dichloromethane in the presence of a catalytic amount of N,N-dimethylformamide.

[0145] Furthermore, the carboxylic acids of the cutin-derived monomers and/or oligomers may be converted to an alcohol prior to coupling to the xenohormetic compound to form an ether linkage. Reduction reactions of this type are well known in the art and may utilize hydride donors such as (LiAIFU); BH3 or its complexes such as picoline borane and borane-pyridine, and 9-BBN, optionally, with an acid catalyst. The alcohol group present of the cutin-derived monomers and/or oligomers may be converted to an alkyl halide using a strong acid (e.g., HC1, HBr, or HI), or with treatment of thionyl chloride, both of which are well known in the art. The alkyl halide can react with a phenol of the xenohormetic compound to form an ether linkage.

IV. Uses and Applications

[0146] The compositions disclosed herein can be used to prevent pre- and post-harvest damage to plants, or parts thereof, thus extending shelf-life and increasing marketability of fresh produce.

[0147] A further aspect of the invention relates to a method for preserving a plant and/or plant part. The method includes providing a plant and/or plant part; applying to the surface of the plant and/or plant part the compositions and/or conjugates described herein thereby forming a coating on the plant and/or plant part, before or after harvest.

[0148] The compositions of the present invention can be applied as a dispersion, a solution, or an emulsion to any of the objects disclosed herein (e.g., plant and/or plant part (e.g., produce)). Techniques known to those of ordinary skill in the art may be used to apply the coating compositions. For example, the object may be dipped into a dispersion, a solution, or an emulsion of the composition. In other embodiments, a dispersion, solution, or emulsion of the composition may be dripped onto the object. In yet other embodiments, the object may be coated (partially or wholly) by spray-coating a dispersion, a solution, or an emulsion of the composition onto the object. The object may also be enrobed (partially or wholly) using a mechanical applicator to apply a dispersion, solution, or emulsion of the composition to the object. In embodiments concerning compositions that are used to coat plants and/or plant parts, such as fruits and/or vegetables, the composition can be added to the object prior to being harvested or after harvesting. Suitable sprayers and enrobers would be recognized by those of ordinary skill in the art. In some embodiments, the coating method may be chosen based on the viscosity of the coating composition. For example, if the coating composition is viscous and the object being coated is a post-harvest product (e.g., fruit or vegetable), then dipping or dripping methods of application are typically used. Pre-harvest application typically involves applying the coating to the plant and/or plant part thereof using a spraying method. Following application of the coating composition to post harvest produce, the coating may be dried either in ambient air or a forced air-drying tunnel.

[0149] In some embodiments, the plant and/or plant part is substantially coated with the composition by spraying, dipping, enrobing, or a combination of two or more thereof. The drying plant and/or plant part after it has been coated to may involve heating the plant and/or plant part at a temperature of about 20°C to about 50°C. In some embodiments, a hot air-drying technique can be used to dry (at least partially) the plant part. Such hot air-drying techniques can use temperatures ranging from 60°C to 90°C for a time period ranging from about 2 minutes to about 10 minutes.

[0150] In some embodiments, the coating ranges in thickness from 0.01mm to 1mm. For example, the coating can range from about 0.01 mm, 0.02 mm, 0.03 mm, 0.04 mm, 0.05 mm, 0.06 mm, 0.07 mm, 0.08 mm, 0.09 mm, 0.1 mm, 0.2 mm, 0.3 mm, 0.4 mm, 0.5 mm, 0.6 mm, 0.7 mm, 0.8 mm, or 0.9 mm up to about 0.02 mm, 0.03 mm, 0.04 mm, 0.05 mm, 0.06 mm, 0.07 mm, 0.08 mm, 0.09 mm, 0.1 mm, 0.2 mm, 0.3 mm, 0.4 mm, 0.5 mm, 0.6 mm, 0.7 mm, 0.8 mm, 0.9 mm, or 1 mm.

[0151] A protective coating can be formed from the compositions described herein by dissolving the cutin-derived monomer and/or oligomer, and xenohormetic compounds, and/or the xenhormetin conjugate described herein to form the coating composition in a solvent (e.g., water, ethanol, or combinations thereof). The concentration of the mixture of cutin-derived monomer and/or oligomer, and xenohormetic compounds, and/or the xenhormetin conjugate described herein in the solvent can, for example, be in a range of about 0.1 to 100 mg/mL. Next, the solution is applied over the surface of the substrate to be coated (e.g., a plant and/or plant part (e.g., produce, such as a fruit or vegetable)), for example by spray coating the substrate or by dipping the substrate in the solution. In the case of spray coating, the solution can, for example, be placed in a spray bottle which generates a fine mist spray. The spray bottle head can then be held approximately six to twelve inches from the substrate, and the substrate then sprayed. In the case of dip coating, the substrate can, for example, be placed in a bag, the solution containing the composition poured into the bag, and the bag then sealed and lightly agitated until the entire surface of the substrate is wet. After applying the solution to the substrate, the substrate is allowed to dry until all of the solvent has evaporated, thereby allowing a coating composed of the cutin-derived monomer and/or oligomer, and xenohormetic compounds, and/or the xenhormetin conjugate described herein to form over the surface of the substrate.

[0152] The compositions of the present invention may be applied using any method known in the art for application of coatings to plants materials. Exemplary methods are disclosed in U.S. Pat. No. 11,046,858 to Zhao et al.; U.S. Pat. No. 10,239,069 to Rodgers; U.S. Pat. No. 7,935,375 to Patcavich; U.S. Pat. No. 3,818,859 to Kalmar; U.S. Pat. No 4,946,694 to Gunnerson et al.; PCT Publication No. W008/061003 to Borsinger et al.; PCT Publication No. W087/004070 to Bagaria et al.; PCT Publication No. WO13/144961 to Nussinovitch et al.; which are hereby incorporated by reference in their entirety.

[0153] The coatings and methods described herein offer a number of distinct features and advantages over current methods of maintaining freshness of agricultural products and food. For instance, the coatings can prevent water loss and shield agricultural products (e.g. plants and/or plant parts) from threats and spoilage caused by bacteria, fungi, viruses and the like. The addition of xenohormetic compounds and/or the xenhormetin conjugates described herein to the coatings afford additional protection to coated plant and/or plant part compared to use of coatings containing only cutin and/or cutin-derivatives.

[0154] The coatings can also protect, for instance, plants and/or plant parts from physical damage (e.g., bruising), water loss, oxidation, and photodamage. Accordingly, the compositions, solutions, and coatings can be used to help store plants and/or plant parts (e.g., produce including fruits and vegetables) for extended periods of time without spoiling. In some instances, the compositions and coatings allow for produce to be kept fresh in the absence of refrigeration. The compositions and coatings described herein can also be edible (i.e., the coatings can be non-toxic for human and/or animal consumption). The methods for forming the coatings described herein can be entirely organic. In some implementations, the coatings are tasteless, colorless, and/or odorless. The coatings can be made from the same chemical feedstocks that are naturally found in the plant cuticle, (e.g., hydroxy and/or dihydroxy palmitic acids, and/or hydroxy oleic and stearic acids) and can thus be organic and all-natural, applied as a mixture, extracts, or a pure compound.

[0155] The compositions and conjugates may be formed from cutin of a first plant species (e.g., utilizing thermal depolymerization), and then deposited over plant matter of the same plant species. Such a coating can, for example, reinforce the cuticle layer that naturally exists over the plant matter. Alternatively, the compositions and conjugates may be formed from cutin of a first plant species, and then disposed over plant matter of a second plant species which is different from the first plant species. The protective coatings that are formed from the compositions and conjugates herein can provide protection against biotic and abiotic stressors for which the native cuticle layer of the second plant species is inherently incapable of providing. For example, the protective coatings deposited over the substrates can provide superior protection against water loss and oxidation than can be inherently provided by the native cuticle layer.

[0156] In some embodiments, the method of the invention provides an extension of the shelflife of a plant and/or plant part by reducing the degree of weight loss during storage. The weight loss of a plant and/or plant part coated with the composition of the invention can be reduced by at least 20%, preferably at least 30%; preferably at least 40%; and more preferably at about 50% compared to an uncoated plant material under the same storage conditions. The method of the present invention also provides the extension of the shelf-life of the plant material between several days and several weeks beyond the shelf-life of the plant material without coating under the same storage conditions. For example, the shelf-life of a plant material (e.g., plant and/or plant part) coated with the formulation of the invention can be doubled compared to the shelflife of a plant material not coated under the same storage conditions. The shelf-life of the plant and/or plant part may be increased up to about 25%, about 30%, about 35%, about 40%, about 50%, about 60%, about 70%, about 80%, about 90%, or more, compared to an uncoated plant and/or plant part. EXAMPLES

[0157] The following examples are merely illustrative and should not be construed as limiting the scope of this disclosure in any way as many variations and equivalents will become apparent to those skilled in the art upon reading the present disclosure.

Example 1. Shelf-life stability Coating

[0158] A mixture of cutin-derived monomers and oligomers is dissolved in water to form a first solution at concentration of approximately 1 mg/mL. An avocado is submerged in this solution for 5 seconds. The avocado is then removed and allowed to air dry.

[0159] A second aqueous solution including quercetin and resveratrol at a concentration of approximately 1 mg/mL is prepared. An avocado is submerged in this solution for 5 seconds. The avocado is then removed and allowed to air dry.

[0160] A third solution of cutin-derived monomers and oligomers in water is prepared at concentration of approximately 1 mg/mL. Quercetin and resveratrol are added to the solution in an amount sufficient to form a concentration of approximately 1 mg/mL. An avocado is submerged in this solution for 5 seconds. The avocado is then removed and allowed to air dry. [0161] The three avocados, as well as a control avocado which has not been subjected to the coating procedures, are stored in ambient conditions (e.g., approximately 15-25 °C and approximately 30-45% relative humidity).

[0162] The avocado treated with the first solution including only the cutin-derived monomers and oligomers has an extended shelf-life of approximately 50% in comparison to the control avocado. Similarly, the avocado treated with the second solution of quercetin and resveratrol also displays an extended shelf-life of approximately 50% in comparison to the control avocado. The avocado treated with the third solution containing both the cutin-derived monomers and oligomers, quercetin and resveratrol has an extended the shelf-life of about 50% beyond the avocados treated with either the first or second solutions.

V. Equivalents and Scope

[0163] Those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments in accordance with the Detailed Description provided herein. The scope of the present disclosure is not intended to be limited to the above Detailed Description, but rather is as set forth in the appended claims.

[0164] In the claims, articles such as “a,” “an,” and “the” may mean one or more than one unless indicated to the contrary or otherwise evident from the context. Claims or descriptions that include “or” between one or more members of a group are considered satisfied if one, more than one, or all of the group members are present in, employed in, or otherwise relevant to a given product or process unless indicated to the contrary or otherwise evident from the context. The disclosure includes embodiments in which exactly one member of the group is present in, employed in, or otherwise relevant to a given product or process. The disclosure includes embodiments in which more than one, or the entire group members are present in, employed in, or otherwise relevant to a given product or process.

[0165] It is also noted that the term “comprising” is intended to be open and permits but does not require the inclusion of additional elements or steps. When the term “comprising” is used herein, the term “consisting of’ is thus also encompassed and disclosed.

[0166] Where ranges are given, endpoints are included. Furthermore, it is to be understood that unless otherwise indicated or otherwise evident from the context and understanding of one of ordinary skill in the art, values that are expressed as ranges can assume any specific value or subrange within the stated ranges in different embodiments of the disclosure, to the tenth of the unit of the lower limit of the range, unless the context clearly dictates otherwise.

[0167] In addition, it is to be understood that any particular embodiment of the present disclosure that falls within the prior art may be explicitly excluded from any one or more of the claims. Since such embodiments are deemed to be known to one of ordinary skill in the art, they may be excluded even if the exclusion is not set forth explicitly herein. Any particular embodiment of the compositions of the disclosure (e.g., any, composition, therapeutic or active ingredient; any method of production; any method of use; etc.) can be excluded from any one or more claims, for any reason, whether or not related to the existence of prior art.

[0168] It is to be understood that the words which have been used are words of description rather than limitation, and that changes may be made within the purview of the appended claims without departing from the true scope and spirit of the disclosure in its broader aspects.

[0169] While the present disclosure has been described at some length and with some particularity with respect to the several described embodiments, it is not intended that it should be limited to any such particulars or embodiments or any particular embodiment, but it is to be construed with references to the appended claims so as to provide the broadest possible interpretation of such claims in view of the prior art and, therefore, to effectively encompass the intended scope of the disclosure.

[0170] All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will control. In addition, section headings, the materials, methods, and examples are illustrative only and not intended to be limiting.

Claims

We Claim:

1. A composition for coating or forming a film on a plant and/or plant part comprising: one or more cutin-derived monomers, oligomers, or combinations thereof; and one or more xenohormetic compounds or derivatives thereof.

2. The composition of claim 1, wherein the xenohormetic compound is a flavone, flavanone, isoflavone, isoflavanone, stilbene, catechin, chaicone, tannin, anthocyanidin, polyphenol, or a derivative thereof.

3. The composition of claim 1 or 2, wherein the xenohormetic compound is a flavone or a derivative thereof.

4. The composition of claim 3, wherein the flavone is selected from the group consisting of fisetin (3,7,3',4'-Tetrahydroxyflavone); quercetin (3, 5, 7,3', 4'- Pentahydroxyflavone); 7,8,3',4'-Tetrahydroxyflavone; 3,6,2',3'-Tetrahydroxyflavone; 4'-Hydroxyflavone; 5,4'-Dihydroxyflavone; 5,7-Dihydroxyflavone; Morin (3,5,7,2',4'-Pentahydroxyflavone); Flavone; 5-Hydroxyflavone; Myricetin (3,5,7,3',4',5'-hexahydroxyflavone); 3,7,3',4',5'-pentahydroxyflavone; 5, 7,3', 4', 5'- pentahydroxyflavone; Gossypetin (3,5,7,8,3',4'-hexahydroxyflavone); Luteolin (5,7,3',4'-Tetrahydroxyflavone); 3,6,3',4'-Tetrahydroxyflavone; 7,3',4',5'- Tetrahydroxyflavone; Kaempferol (3,5,7,4'-Tetrahydroxyflavone); 6- Hydroxyapigenin (5,6,7,4'-Tetrahydroxyflavone); Scutellarein (5, 6,7,4’- Tetrahydroxyflavone); Apigenin (5,7,4'-Trihydroxyflavone); 3, 6,2', 4'- Tetrahydroxyflavone; 7, 4 ’-Dihydroxyflavone, and combinations thereof.

5. The composition of claim 1 or 2, wherein the xenohormetic compound is a flavanone or a derivative thereof.

6. The composition of claim 5, wherein the flavanone is selected from the group consisting of flavanone, hesperidin, naringenin, 3,5,7,3',4'-pentahydroxyflavanone, naringin, eriocitrin, taxifolin, and combinations thereof. The composition of claim 1 or 2, wherein the xenohormetic compound is an isoflavone, an isoflavanone, or a derivative thereof. The composition of claim 7, wherein the isoflavone or isoflavanone is selected from the group consisting of daidzein; daidzin; 6-0-malonyl daidzein; 6-O-acetyl daidzein; genistein; 6-0-malonyl genistein; 6-O-acetyl genistein; glycitein; 6-0- malonyl glycitein; 6-O-acetyl glycitein; Biochanin A; formononetin; irilone; prunetin; pratensein; glycitinn; dihydrodaidzein; equol; O-desmethylangolensin; daidzein 7,4'-di-O-sulfate; daidzein 7-O-beta-D-glucuronide; daidzein 4'-O-sulfate; 6,7,5'-trihydroxyisoflavone; 6,7,3',4'-tetrahydroxyisoflavone; 7,8,4'- trihydroxy isoflavone; 5,6,7,4'-tetrahydroxyisoflavone; dihydrogenistein; p- ethylphenol; 3', 4', 5, 7-tetrahydroxyisoflavone; genistein 4'-O-sulfate; genistein 7-O- beta-D-glucuronide; genistein 4'-O-sulfate; 4',5,7-trihydroxyisoflavanone, and combinations thereof. The composition of claim 1 or 2, wherein the xenohormetic compound is a stilbene or a derivative thereof. The composition of claim 9, wherein the stilbene is selected from the group consisting of resveratrol, trans-stilbene, cis-stilbene, pterostilbene, piceatannol, rhapontigenin, pinosylvin, rhapontin, deoxyrhapontin, and combinations thereof. The composition of claim 1 or 2, wherein the xenohormetic compound is a chaicone or a derivative thereof. The composition of claim 11, wherein the chaicone is selected from the group consisting of isoliquiritigenin (4,2',4'-Trihydroxychalcone), Butein (3, 4,2', d'Tetrahydroxy chaicone); chaicone; 3,4,2'4'6'-Pentahydroxychalcone; and mixtures thereof. The composition of claim 1 or 2, wherein the xenohormetic compound is a catechin or a derivative thereof. The composition of claim 13, wherein the catechin is selected form the group consisting of (+)-catechin, (-)-catechin, catechin gallate (CG), (+)- and (-)- epicatechin (EC), (-)-gallocatechin, epigallocatechin (EGC), epigallocatechin-3- gallate, and combinations thereof. The composition of claim 1 or 2, wherein the xenohormetic compound is an anthocyanidin or derivative thereof. The composition of claim 13, wherein the anthocyanidin is selected form the group consisting of pelargonidin chloride, cyanidin chloride, delphinidin chloride, and combinations thereof. The composition of claim 1 or 2, wherein the xenohormetic compound is a polyphenol or derivative thereof. The composition of claim 17, wherein the polyphenol is selected from the group consisting of curcumin; quercetin; fisetin; rutin; quercitrin; catechin; gallocatechin; catechin 3-gallate; gallocatechin 3-gallate; epicatechin; epigallocatechin; epicatechin 3-gallate; epigallocatechin3-gallate (ECGC); theaflavin-3-gallate; theaflavin-3'- gallate; theaflavin-3,3'-digallate; kaempferol; myricetin; galangin; isorhamnetin; pachypodol; rhamnazin; a pyranoflavonol; furanoflavonol; luteolin; resveratrol; apigenin; tangeritin; hesperetin; naringenin; eriodictyol; homoeriodictyol; and derivatives thereof. The composition of claims 1-18, further comprising one or more nicotinamide adenine dinucleotide increasing compounds. The composition of claim 19, wherein the nicotinamide adenine dinucleotide increasing compound is selected from the group consisting of nicotinamide ribose (NR), nicotinic acid riboside (NaR), ester derivatives of nicotinic acid riboside, nicotinic acid (niacin), ester derivatives of nicotinic acid, nicotinic mononucleotide (NMN), nicotinic acid mononucleotide (NaMN), nicotinic acid dinucleotide (NaAD+), ester derivatives of nicotinic acid mononucleotide, nicotinic acid adenine dinucleotide (NaAD), nicotinic acid adenine dinucleotide (NAAD), and combinations thereof.

21. The composition of claim 19 or 20, wherein the nicotinamide adenine dinucleotide increasing compound is nicotinic acid riboside.

22. The composition of any of the above claims, wherein the xenohormetic compounds are a mixture of xenohormetic compounds comprising one or more flavone, flavanone, isoflavone, isoflavanone, stilbene, catechin, chaicone, tannin, polyphenol, and/or anthocyanidin.

23. The composition of claim 22, wherein the mixture of xenohormetic compounds comprises stilbenes and flavones.

24. The composition of claim 22 or 23, wherein the mixture of xenohormetic compounds comprises resveratrol, quercetin and fisetin.

25. The composition of any of the above claims, wherein the ratio of cutin-derived monomers, oligomers, and combinations thereof and the xenohormetic compounds or derivatives thereof ranges from 10:90 wt ratio to 90:10 wt ratio.

26. The composition of claim 25, wherein the ratio of cutin-derived monomers, oligomers, and combinations thereof and the xenohormetic compounds or derivatives thereof is about 1 : 1 wt ratio.

27. The composition of claim 26, wherein the ratio of cutin-derived monomers, oligomers, and combinations thereof, the xenohormetic compounds or derivatives thereof, and nicotinamide adenine dinucleotide increasing compound is about 1:1:1.

28. The composition of any of the above claims further comprising a solvent.

29. The composition of claim 28, wherein the solvent is selected from water, ethanol, and combinations thereof.

30. The composition of claim 28 or 29, wherein the cutin-derived monomers, oligomers, and combinations thereof and the xenohormetic compounds or derivatives are present in a centration ranging from about 0.1 mg/mL to 100 mg/mL.

31. The composition of any of the above claims further comprising one or more UV inhibitor, emulsifier, solubilizer, stabilizing agent, crosslinking agent, and combinations thereof.

32. The composition of claim 31, wherein the composition comprises an oleic acid and/or olive oil dried powder solubilizer.

33. The composition of any of the above claims wherein the cutin-derived monomers, oligomers, or combinations thereof comprises compounds of Formula (I), Formula (II), and/or Formula (III):

wherein for Formula (I):

R¹¹ is — H, — glyceryl, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, — C₁-C₆ alkynyl, — C3- C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹³, — NR¹³R¹⁴, — SR¹³, or halogen;

R¹² is —OH, — H, — Ci-C₆ alkyl, — C₁-C₆ alkenyl, — Ci-C₆ alkynyl, — C3- C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹³, — NR¹³R¹⁴, — SR¹³, halogen, — COOH, or — COOR¹¹; and m, n, and o are each independently an integer in the range of 0 to 30, and 0<m+n+o<30; wherein for Formula II:

R¹, R², R⁴ and R⁵ are each independently — H, — OR¹¹, — NR¹¹R¹², — SR¹¹, halogen, — C₁-C₆ alkyl, — C₁-C₆ alkenyl, — C₁-C₆ alkynyl, — C3-C7 cycloalkyl, aryl, or 5- to 10-membered ring heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with — OR¹¹, — NR¹¹R¹², — SR¹¹, or halogen;

0<m+n<25; wherein for Formula III:

R³, R⁴, R⁷, and R⁸ are each independently, at each occurrence, — H, — OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, halogen, — Ci-C₆ alkyl, — C₂-C₆ alkenyl, — C₂-C₆ alkenyl, — C₂- C₆ alkynyl, — C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen; or

R¹⁴ and R¹⁵ are each independently, at each occurrence, — H, — C₁-C₆ alkyl, — C₂-C₆ alkenyl, or — C₂-C₆ alkynyl; the symbol represents a single bond or a cis or trans double bond; the symbol = represents a cis or trans double bond; n is 0, 1, 2, 3, 4, 5, 6, 7 or 8; m is 0, 1, 2 or 3; q is 0, 1, 2, 3, 4 or 5; r is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and

R is selected from — H, — C₁-C₆ alkyl, — C₂-Ce alkenyl, — C₂-Ce alkynyl, — C3- C7 cycloalkyl, aryl, 1-glyceryl, 2-glyceryl, or heteroaryl.

34. The composition of claim 33, wherein the cutin-derived monomers, oligomers, or combinations thereof comprises compounds of Formula (I).

35. The composition of claim 33, wherein the cutin-derived monomers, oligomers, or combinations thereof comprises compounds of Formula (II).

36. The composition of claim 33, wherein the cutin-derived monomers, oligomers, or combinations thereof comprises compounds of Formula (III).

37. The composition of clams 33-36, wherein the cutin-derived monomers, oligomers, or combinations thereof comprises a mixture of compounds of Formula (I), and/or Formula (II), and/or Formula (III).

38. The composition of any of the above claims, wherein the cutin-derived monomers, oligomers, or combinations thereof are chemically bonded to the polyphenolic or xenohormetic compounds or derivatives.

39. A method of preparing a composition comprising xenohormetic compounds and cutin-derived monomers, oligomers, or combinations thereof, said method comprising: providing cutin-derived monomers, oligomers, or combinations thereof; providing xenohormetic compounds; and combining the xenohormetic compounds and cutin-derived monomers, oligomers, or combinations thereof in a solvent to form a first mixture.

40. The method of claim 39, wherein the cutin-derived monomers, oligomers, and combinations thereof, and the xenohormetic compounds or derivatives thereof, are in a weight ration ranging from 10:90 to 90:10.

41. The method of claim 40, wherein the weight ratio of the cutin-derived monomers, oligomers, and combinations thereof, and the xenohormetic compounds or derivatives thereof is 1:1.

42. The method of claims 39-41, wherein the solvent is water, ethanol, or a combination thereof.

43. The method of claims 39-42, wherein the first mixture has a concentration ranging from about IxlO^-5 M to IxlO^-3 M.

44. A xenhormetin conjugate of Formula (IV) for coating or forming a film on a plant and/or plant part:

wherein:

Q is a xenhormetin moiety; X is O, or N;

R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², and R¹³ are independently selected at each occurrence from — H, —OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, halogen, — Ci-C₆ alkyl, — C₂-C₆ alkenyl, — C₂- Ce alkynyl, — C3-C7 cycloalkyl, aryl, and heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen;

R³ and R⁴ can combine with the carbon atoms to which they are attached to form a C3- C₆ cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or

R⁷ and R⁸ can combine with the carbon atoms to which they are attached to form a C3- C₆ cycloalkyl, a C4-C6 cycloalkenyl, or 3- to 6-membered ring heterocycle;

R¹⁴ and R¹⁵ are independently selected at each occurrence from — H, — C₁-C₆ alkyl, — C₂-C₆ alkenyl, and — C₂-C₆ alkynyl;

45. The xenhormetin conjugate of claim 41, wherein

Q is a moiety selected from the group consisting of flavones, isoflavones, stilbenes, flavanones, isoflavanones, catechins, chaicones, tannins, and anthocyanidins.

46. The xenhormetin conjugate of claim 45, wherein

Q is a stilbene or chaicone moiety of Formula (V): wherein

Ri, R2, R3, R4, R5, R'1, R'2, R'3, R'4, and R'5 are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of Ri, R2, R3, R4, R5, R'1, R'2, R'3, R'4, or R's comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

M represents O, NR, or S;

47. The xenhormetin conjugate of claim 45, wherein Q is a flavanone moiety of Formula (VI):

wherein

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

M represents H2, O, NR, or S; Z represents CR, O, NR, or S;

X represents CR or N; and

Y represents CR or N.

48. The xenhormetin conjugate of claim 45, wherein

Q is an isoflavanone moiety of Formula (VII):

wherein

Ri, R₂, R₃, R4, R'i, R'2, R'3, R'4, R'S and R"i are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of Ri, R2, R3, R4, R'I, R'2, R'3, R'4, R's or R"i comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

M represents H2, O, NR, or S;

Z represents C(R)2, O, NR, or S;

X represents CR or N; and

Y represents CR or N.

49. The xenhormetin conjugate of claim 45, wherein

Q is a flavone moiety of Formula (VIII):

wherein Ri, R2, R3, R4, R'i, R'2, R'3, R'4, and R'5 are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of Ri, R2, R3, R4, R'i, R'2, R'3, R'4, or R'5 comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

M represents H2, O, NR, or S;

Z represents CR, O, NR, or S; and

X represents CR" or N.

50. The xenhormetin conjugate of claim 45, wherein

Q is an isoflavone moiety of Formula (IX):

wherein

R represents H, alkyl, aryl, heteroaryl, or aralkyl;

M represents H2, O, NR, or S;

Z represents C(R)2, O, NR, or S; and

Y represents CR" or N.

51. The xenhormetin conjugate of claim 45, wherein Q is an anthocyanidin moiety of Formula (X):

wherein

R3, R4, R5, R6, R7, Rs, R'2, R'3, R'4, R'5, and R'e are independently selected from H, alkyl, aryl, heteroaryl, aralkyl, alkaryl, heteroaralkyl, halide, NO2, SR, OR, N(R)2, carboxyl, or a bond to the compound of Formula (IV), wherein each alkyl is optionally substituted with a bond to the compound of Formula (IV), wherein at least one of R3, R4, R5, Re, R7, Rs, R'2, R'3, R'4, R's, or R'e comprises a bond to the compound of Formula (IV);

R represents H, alkyl, aryl, heteroaryl, or aralkyl; and

A- represents an anion selected from the following: Cl", Br“, or I-.

52. A method of forming the xenhormetin conjugate of Formula (IV)

wherein:

Q is a xenhormetin moiety;

X is O, or N;

R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², and R¹³ are independently selected at each occurrence from — H, — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, halogen, — C₁-C₆ alkyl, — C2- Ce alkenyl, — C2-C6 alkynyl, — C3-C7 cycloalkyl, aryl, and heteroaryl, wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, — NR¹⁴R¹⁵, — SR¹⁴, or halogen;

R³, R⁴, R⁷, and R⁸ are independently selected at each occurrence from — H, — OR¹⁴, — NR¹⁴R¹⁵, —SR¹⁴, halogen, — Ci-C₆ alkyl, — C₂-C₆ alkenyl, — C₂-C₆ alkenyl, — C2-C6 alkynyl, — C3-C7 cycloalkyl, aryl, or heteroaryl wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted with one or more — OR¹⁴, —

NR¹⁴R¹⁵, — SR¹⁴, or halogen; or

R¹⁴ and R¹⁵ are independently selected at each occurrence from — H, — C₁-

C₆ alkyl, — C2-C6 alkenyl, and — C2-C6 alkynyl;

= represents a single bond or a cis or trans double bond; a is 0 or 1 ; b is 0, 1, 2, 3, 4, 5, 6, 7 or 8; c is 0 or 1 , d is 0, 1, 2 or 3; e is 0 or 1 ; f is 0, 1, 2, 3, 4, 5, 6, 7 or 8; and g is 0, 1, 2, 3, 4 or 5; comprising: providing a xenohormetin compound; obtaining cutin from cutin-containing plant matter; adding the xenohormetin compound and cutin to a solvent to form a first mixture, the solvent having a boiling point at a first temperature at a pressure of one atmosphere; and heating the first mixture to a second temperature and second pressure, the second temperature being higher than the first temperature and the second pressure being higher than one atmosphere, to form a second mixture comprising the xenohormetin-conjugate of Formula (IV).

53. The method of claim 52, wherein the solvent is a nucleophilic solvent.

54. The method of claim 53, wherein the nucleophilic solvent is selected from the group consisting of water, glycerol, methanol, ethanol, and combinations thereof.

55. The method of claims 52-54, wherein the first temperature ranges from 15 °C to 50°C.

56. The method of claims 52-55, wherein the second temperature ranges from 45°C to 85°C.

57. The method of claims 52-56, wherein the second pressure ranges from about 5 atm up to about 1000 atm.

58. The method of claims 52-57, wherein the method is run in low light, wherein the low light ranges from 5 lumens per sq ft up to 70 lumens per sq ft.

59. Method for preserving a plant and/or plant part comprising: providing a plant and/or plant part; applying to the surface of the plant and/or plant part the composition of any one of claims 1-38, or the conjugate of any one of claims 44-51, thereby forming a coating on the plant and/or plant part.

60. The method of claim 59, wherein the composition of any one of claims 1-38, or the conjugate of any one of claims 44-51, further comprises a solvent selected from water, ethanol, and combinations thereof.

61. The method of claim 59, wherein the plant and/or plant part is coated with the composition of any one of claims 1-38, or the conjugate of any one of claims 44-51, by spraying, dipping, enrobing, or a combination of two or more thereof.

62. The method of claims 59-61, further comprising drying the coating on the plant and/or plant part at a temperature ranging from 20°C to 50°C.

63. The method of claims 59-62, wherein the coating ranges in thickness from 0.01mm to 1mm.

64. The method of claims 59-63, wherein the coating preserves the plant and/or plant part for a period of time at least 20% longer, at least 30% longer, at least 40% longer, or at least 50% longer than an uncoated plant and/or plant part.