Method for treating plant-based products to reduce microbial growth and extend shelf life

Abstract

The present application relates to a method of inhibiting microbial growth in and / or on a surface of a plant-based product by treating the plant-based product with a composition containing one or more ascarosides. In one embodiment, the method of inhibiting microbial growth in and / or on a surface of a plant-based product comprises treating the plant-based product with a composition comprising one or more ascarosides, wherein the treated plant-based product is resistant to microbial growth. The microbial growth inhibited can be the growth of human pathogenic microorganisms. Other microbial growth that may be inhibited includes bacterial growth, fungal growth, and mold growth.

Description

[Technical field]

[0001] Claiming priority This application claims priority to U.S. Provisional Patent Application No. 63 / 328,596, entitled "Methods of Treating Plant-Based Products to Reduce Microbe Proliferation and Extension Shelf Life," filed April 7, 2022, the contents of which are incorporated herein by reference.

[0002] FIELD OF THEINVENTION This application relates generally to methods for reducing foodborne illness and / or extending the shelf life of plant-based products. More specifically, the present invention provides methods for treating fruits, vegetables, and other products derived from plants to reduce or prevent microbial growth and / or slow spoilage of these items. [Background technology]

[0003] Fruits, vegetables, and plants are subject to many different types of contamination that can occur at any time, from before harvest, through harvest, to when (and after) the produce is delivered to the consumer. Most fruits and vegetables are washed after harvest to remove dirt and pesticide residues. For some fruits and vegetables, dump tanks (containers filled with water) can be used to collect the produce during crop harvest. In these tanks, water is used to wash the produce while also preventing blemishes on the produce. Some fruits, vegetables, and plants can be washed after harvest using various spray washing techniques or washing tanks.

[0004] However, the potential for produce contamination is increased if improper harvesting or washing techniques are used. Many fruits and vegetables are harvested manually by harvesters, who may have poor hygiene practices or may be infected with infectious diseases, which can also be a source of bacterial contamination. Reusing water from dump tanks or improper water discharge can also lead to the accumulation of infectious disease pathogens in the water used to collect the produce.

[0005] To mitigate these potential problems, extensive post-harvest cleaning with various chemical treatments is typically performed to reduce microbial contamination. For example, treatments with electrolyzed water, organic acids, calcium hypochlorite or sodium hypochlorite (bleach) are routinely used to minimize microbial contamination. Although chemicals such as calcium hypochlorite and sodium hypochlorite are generally effective, they are toxic by oral and dermal routes, and these solutions can release harmful gases, potentially endangering workers. To make matters worse, these chemicals are strong oxidizing and halogenating agents that can reduce the nutritional value of the plant or contaminate the plant with residual chlorinated organic molecules formed during processing. It would be beneficial to provide additional methods to ensure the safety of fruits and vegetables. Summary of the Invention

[0006] Compositions and methods are provided for inhibiting microbial growth in and / or on plant-based products.

[0007] In one embodiment, a method of inhibiting microbial growth in and / or on a plant-based product comprises treating the plant-based product with a composition comprising one or more ascarosides, wherein the treated plant-based product is resistant to microbial growth. The microbial growth inhibited can be the growth of human pathogenic microorganisms. Other microbial growth that may be inhibited includes bacterial growth, fungal growth, and mold growth.

[0008] In one embodiment, the microbial growth that is inhibited is microbial growth associated with spoilage of plant-based products.

[0009] In one embodiment, a method for extending the shelf life of a plant-based product comprises treating the produce after harvest with a composition comprising one or more ascarosides.

[0010] In one embodiment, a method for increasing the shelf life of a plant-based product comprises treating the produce prior to harvest with a composition comprising one or more ascarosides.

[0011] In one embodiment, a method for extending the shelf life of vegetables comprises treating the vegetables with a composition comprising one or more ascarosides.

[0012] In one embodiment, a method for extending the shelf life of fruit comprises treating the fruit with a composition comprising one or more ascarosides.

[0013] In one embodiment, a method for extending the shelf life of a plant-based material includes continuously contacting the plant material with a composition comprising one or more ascarosides during transportation, sale, or use by the consumer, such as by continuously immersing cut flowers, ornamental leaves, or herb stems in an ascaroside-containing solution, or by continuously contacting the stems or other parts of cut flowers, ornamental leaves, or herbs with an absorbent material moistened with an ascaroside-containing solution. In another embodiment, the ascaroside composition may be provided packaged with the ornamental plant material for use by the consumer, such as by adding the ascaroside composition to vase water. In certain embodiments, ascarosides may be incorporated into nutritional compositions containing sugars or similar substances that are designed to extend the life of cut flowers and leaves after arranging them in a vase.

[0014] Methods of treating the plant-based product with a composition comprising one or more ascarosides include, for example, dipping the plant-based product, spraying the plant-based product, or dip-coating the plant-based product. Treating the plant-based product with a composition comprising one or more ascarosides prevents or inhibits microbial growth in and / or on the surface of the plant-based product.

[0015] Plant-based products include products produced by a plant (eg, fruits and vegetables) or products obtained by harvesting all or part of a plant (eg, lettuce, sprouts, flowers and grasses).

[0016] Exemplary vegetables that can be treated with the methods of the present disclosure include, but are not limited to, stem-feeding vegetables, leaf-feeding vegetables, flower-feeding vegetables, root / tuber-feeding vegetables, bulb-feeding vegetables, fruit-feeding vegetables, and seed-feeding vegetables.

[0017] Exemplary fruits that can be treated with the methods of the present disclosure include, but are not limited to, berries, citrus fruits, stone fruits, pome fruits, melons, and tropical fruits.

[0018] Exemplary non-food plant materials that can be treated with the methods of the present disclosure include, but are not limited to, cut flowers, garlands, ornamental foliage, Christmas trees, flower crowns, and the like.

[0019] In one embodiment, the one or more ascarosides have the formula (I): [ka] where Z is an optionally substituted C 2-40 is an aliphatic group, R a and R b Each of is independently -H or C 1-20 aliphatic, C 1-20 Achill, C 1-20Heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-bridged functional group, sulfur-bridged functional group, silicon-bridged functional group, C 2-20 Carbonates (e.g., -C(O)OR c part), C 2-20 Carbamates (e.g., -C(O)N(R c )2 parts), C 2-20 Thioesters (e.g., -C(S)R c part), C 2-20 Thiocarbonates (e.g., -C(S)OR c part), C 2-20 Dithiocarbonates (e.g., -C(S)SR c part), C 1-20 Thiocarbamates (e.g., -C(S)N(R c 2) an optionally substituted moiety selected from the group consisting of a linkage via a bond or a carbon-containing linker moiety to a sugar moiety, a peptide, a polymer chain, or another ascaroside molecule; R c represents independently at each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; R a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation.

[0020] In one embodiment, the one or more ascarosides conform to formula (I), where Z is: (i) -CH(CH3)-R 1 where R 1 is an optionally substituted C 1-40 is an aliphatic group; (ii) -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (iii) -CH(CH3)-(CH2) n -CH=CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (iv) -CH(CH3)-(CH2) n -CH(OH)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (v) -CH(CH3)-(CH2) n -C(O)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (vi)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (vii)-(CH2) n -CH=CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (viii)-(CH2) n -CH(OH)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; or (ix)-(CH2) n -C(O)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 A linkage via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule.

[0021] In one embodiment, the one or more ascarosides conform to formula (I), where R a and R b are -H, and Z is (x)-CH(CH3)-(CH2) n -CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xi) -CH(CH3)-(CH2) n -CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xii) -CH(CH3)-(CH2) n -CH(OH)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xiii) -CH(CH3)-(CH2) n -C(O)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xiv)-(CH2) n -CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xv)-(CH2) n -CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xvi)-(CH2) n-CH(OH)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; or (xvii)-(CH2) n -C(O)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 A linkage to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0022] In certain embodiments, for ascarosides of formula I, Z is -CH(CH3)-(CH2). n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide. A specific example of this type of ascaroside is ascr#18 shown below. [ka]

[0023] In certain embodiments, the one or more ascarosides have formula I, where Z is -CH(CH3)-(CH2). n -CH=CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide. A specific example of this type of ascaroside is ascr#7 shown below. [ka]

[0024] In one embodiment, the plant-based product is treated with an aqueous solution comprising one or more ascarosides. In one embodiment, the plant-based product is treated by immersion in a composition comprising one or more ascarosides. In a particular embodiment, the plant-based product is immersed in a tank containing a composition comprising one or more ascarosides during harvesting of the plant-based product. In another embodiment, the plant-based product is treated by spraying with a composition comprising one or more ascarosides.

[0025] In one embodiment, the plant-based product is soaked in the aqueous solution for about 1 minute to about 6 hours. The concentration of one or more ascarosides in the aqueous solution may be from about 1 ppb to about 100 ppm.

[0026] These and other features, aspects and advantages of the present disclosure will become apparent upon reading the following detailed description in conjunction with the accompanying drawings, which are briefly described below. The present invention includes any combination of two, three, four or more of the above-described embodiments, as well as any combination of two, three, four or more of the features or elements described in the present disclosure, regardless of whether such features or elements are explicitly combined in a particular embodiment herein. The present disclosure is intended to be read in its entirety such that it should be considered as intended that any separable features or elements of the disclosed invention can be combined in any of its various aspects and embodiments, unless the context clearly indicates otherwise. Other aspects and advantages of the present disclosure will become apparent from the following.

[0027] definition In order that this disclosure may be more readily understood, certain terms are first defined below. Further definitions of these terms, as well as other terms, are set forth throughout the specification.

[0028] In this application, unless otherwise clear from the context, the term "a" may be understood to mean "at least one." As used in this application, the term "or" may be understood to mean "and / or." As used in this application, the terms "comprising" and "including" may be understood to encompass the itemized recited components or steps, whether presented by themselves alone or together with one or more additional components or steps. As used in this application, the term "comprise," as well as variations of this term, such as "comprising" and "comprises," are not intended to exclude other additives, components, integers, or steps.

[0029] As used herein, the terms "about" and "approximately" are used as equivalents. Unless otherwise stated, the terms "about" and "approximately" can be understood to allow for standard variations that would be understood by one of ordinary skill in the art. When a range is provided herein, the endpoints are included. Any numbers used in this application with or without about / approximately are meant to encompass any typical variations that would be understood by a person of ordinary skill in the relevant art. In some embodiments, the term "about" or "approximately" refers to a range of values ​​that is included within 25%, 20%, 19%, 18%, 17%, 16%, 15%, 14%, 13%, 12%, 11%, 10%, 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, 1% or less in either direction (above or below) of the stated reference value, unless otherwise stated or otherwise evident from the context (except where such numbers may exceed 100% of the possible values).

[0030] Definitions of specific functional groups and chemical terms are described in more detail below. For purposes of the present invention, chemical elements are identified according to the endpapers of the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75th Ed., and specific functional groups are generally defined as described therein. In addition, general principles of organic chemistry, as well as specific functional moieties and reactivities, are described in Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999, Smith and March March's Advanced Organic Chemistry, 5th Ed. ... th Edition, John Wiley & Sons, Inc., New York, 2001, Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989, Carruthers, Some Modern Methods of Organic Synthesis, 3 rd Edition, Cambridge University Press, Cambridge, 1987, the entire contents of each of which are incorporated herein by reference.

[0031] Certain compounds provided herein may contain one or more asymmetric centers and therefore may exist in various stereoisomeric forms, such as enantiomers and / or diastereomers.Accordingly, the compounds of the present invention and their compositions may be in the form of individual enantiomers, diastereomers or geometric isomers, or may be in the form of a mixture of stereoisomers.In certain embodiments, the compounds of the present invention are enantiopure compounds.In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

[0032] Additionally, certain compounds described herein may have one or more double bonds that can exist as Z or E isomers, unless otherwise indicated. The compounds of the present invention can be provided as individual isomers substantially free of other isomers, or as mixtures of various isomers, e.g., racemic mixtures of enantiomers.

[0033] As used herein, the term "isomer" includes all geometric and stereoisomers. For example, "isomer" includes cis and trans isomers, E and Z isomers, R and S enantiomers, diastereomers, (D) isomers, (L) isomers, racemic mixtures thereof, and other mixtures thereof, as being within the scope of the present invention. For example, in some embodiments, a compound may be provided that is substantially free of one or more corresponding stereoisomers, and may be referred to as "stereochemically enriched."

[0034] In some embodiments, when a particular enantiomer is preferred, the enantiomer may be provided substantially free of the opposite enantiomer and may be referred to as "optically enriched". As used herein, "optically enriched" means that the compound of the present invention is made up of a significantly higher proportion of one enantiomer. In certain embodiments, the compound is made up of at least about 90% by weight of one enantiomer. In some embodiments, the compound is made up of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8% or 99.9% by weight of one enantiomer. In some embodiments, the enantiomeric excess of the provided compound is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8% or 99.9%. In some embodiments, enantiomers can be separated from racemic mixtures by any known method, such as chiral high performance liquid chromatography (HPLC) and the formation and crystallization of chiral salts, or can be prepared by asymmetric synthesis.See, for example, Jacques, et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, SH, et al., Tetrahedron 33:2725 (1977); Eliel, ELStereochemistry of Carbon Compounds (McGraw-Hill, NY, 1962); Wilen, SHTables of Resolving Agents and Optical Resolutions p.268 (EL Eliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0035] The terms "halo" and "halogen," as used herein, refer to an atom selected from fluorine (fluoro, -F), chlorine (chloro, -Cl), bromine (bromo, -Br), and iodine (iodo, -I).

[0036] The terms "aliphatic" or "aliphatic group," as used herein, refer to a hydrocarbon moiety that may be straight-chained (i.e., unbranched), branched, or cyclic (including fused, bridged, and spiro-fused polycyclic), and may be fully saturated or contain one or more units of unsaturation, but is not aromatic. Unless otherwise specified, an aliphatic group contains 1-30 carbon atoms. In certain embodiments, an aliphatic group contains 1-12 carbon atoms. In certain embodiments, an aliphatic group contains 1-8 carbon atoms. In certain embodiments, an aliphatic group contains 1-6 carbon atoms. In some embodiments, an aliphatic group contains 1-5 carbon atoms, in some embodiments, an aliphatic group contains 1-4 carbon atoms, in still other embodiments, an aliphatic group contains 1-3 carbon atoms, and in still other embodiments, an aliphatic group contains 1-2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear or branched alkyls, alkenyls, and alkynyls, as well as hybrids thereof, such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl, or (cycloalkyl)alkenyl.

[0037] The terms "heteroaliphatic" or "heteroaliphatic group," as used herein, refer to an aliphatic group in which one or more carbon or hydrogen atoms are replaced by a heteroatom (e.g., oxygen, nitrogen, sulfur, phosphorus, boron, etc.).

[0038] The term "unsaturated," as used herein, means that a moiety has one or more double or triple bonds.

[0039] The term "alkyl," as used herein, refers to a saturated, straight or branched chain hydrocarbon group obtained by removing one hydrogen atom from an aliphatic moiety containing 1-6 carbon atoms. Unless otherwise specified, an alkyl group contains 1-12 carbon atoms. In certain embodiments, an alkyl group contains 1-8 carbon atoms. In certain embodiments, an alkyl group contains 1-6 carbon atoms. In some embodiments, an alkyl group contains 1-5 carbon atoms, in some embodiments, an alkyl group contains 1-4 carbon atoms, in still other embodiments, an alkyl group contains 1-3 carbon atoms, and in still other embodiments, an alkyl group contains 1-2 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, sec-pentyl, isopentyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-decyl, n-undecyl, dodecyl, and the like.

[0040] The term "alkenyl" as used herein means a monovalent group obtained by removing one hydrogen atom from a straight or branched chain aliphatic moiety having at least one carbon-carbon double bond. Unless otherwise specified, an alkenyl group contains 2-12 carbon atoms. In certain embodiments, an alkenyl group contains 2-8 carbon atoms. In certain embodiments, an alkenyl group contains 2-6 carbon atoms. In some embodiments, an alkenyl group contains 2-5 carbon atoms, in some embodiments, an alkenyl group contains 2-4 carbon atoms, in still other embodiments, an alkenyl group contains 2-3 carbon atoms, and in still other embodiments, an alkenyl group contains 2 carbon atoms. Alkenyl groups include, for example, ethenyl, propenyl, butenyl, 1-methyl-2-buten-1-yl, and the like.

[0041] The term "aryl" used alone or as part of a larger moiety, such as in "aralkyl", "aralkoxy" or "aryloxyalkyl", refers to monocyclic and polycyclic ring systems having a total of 5 to 20 ring members, in which at least one ring of the system is aromatic, and in which each ring of the system contains 3 to 12 ring members. The term "aryl" may be used interchangeably with the term "aryl ring". In certain embodiments of the invention, "aryl" refers to aromatic ring systems, including but not limited to phenyl, biphenyl, naphthyl, anthracyl, and the like, which may bear one or more substituents. Also included within the scope of the term "aryl" as used herein are groups in which the aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthoimidyl, phenanthridinyl, or tetrahydronaphthyl.

[0042] As described herein, the compounds of the present invention may contain "optionally substituted" moieties. In general, the term "substituted", whether preceded by the term "optionally" or not, means that one or more hydrogens of the specified moiety may be replaced with a suitable substituent. Unless otherwise specified, an "optionally substituted" group may have a suitable substituent at each substitutable position of the group, and when more than one position in any given structure may be substituted with more than one substituent selected from a specified group, the substituents may be the same or different at each and every position. The combinations of substituents envisioned are preferably those that result in the formation of stable or chemically feasible compounds. As used herein, the term "stable" refers to a compound that is substantially unchanged when subjected to conditions that allow for production, detection, and, in certain embodiments, recovery, purification, and use for one or more of the purposes disclosed herein.

[0043] Suitable monovalent substituents on a substitutable carbon atom of an "optionally substituted" group are independently halogen; -(CH) 0-4 R o ;-(CH2) 0-4 ORo ;-O-(CH2) 0-4 C(O)OR o ;-(CH2) 0-4 CH(OR o )2;-(CH2) 0-4 S.R. o ;-(CH2) 0-4 Ph, which is R o may be substituted with; R o may be substituted with -(CH2) 0-4 O(CH2) 0-1 Ph;-CH=CHPh, which is R o may be substituted with; -NO2; -CN; -N3; ​​-(CH2) 0-4 N(R o )2;-(CH2) 0-4 N(R o )C(O)R o ;-N(R o )C(S)R o ;-(CH2) 0-4 N(R o )C(O)NR o 2;-N(R o )C(S)NR o 2;-(CH2) 0-4 N(R o )C(O)OR o ;-N(R o )N(R°)C(O)R o ;-N(R°)N(R°)C(O)NR o 2;-N(R o )N(R o )C(O)OR o ;-(CH2) 0-4 C(O)R°;-C(S)R°;-(CH2) 0-4 C(O)OR o ;-(CH2) 0-4 C(O)N(R o )2;-(CH2) 0-4 C(O)SR o ;-(CH2) 0-4 C(O)OSiR o 3;-(CH2) 0-4 O.C.(O)R o ;-OC(O)(CH2) 0-4 SR-;SC(S)SR o ;-(CH2)0-4 SC(O)R o ;-(CH2) 0-4 C(O)NR o 2;-C(S)NR o 2;-C(S)SR o ;-SC(S)SR o ;-(CH2) 0-4 OC(O)NR o 2;-C(O)N(OR o )R o ;-C(O)C(O)R o ;-C(O)CH2C(O)R o ;-C(NOR o )R o ;-(CH2) 0-4 SSR o ;-(CH2) 0-4 S(O)2R o ;-(CH2) 0-4 S(O)2OR o ;-(CH2) 0-4 OS(O)2R o ;-S(O)2NR o 2;-(CH2) 0-4 S(O)R o ;-N(R o )S(O)NR o 2;-N(R o )S(O)2R o ;-N(OR o )R o ;-C(NH)NR o 2;-P(O)2R o ;-P(O)R o 2;-OP(O)R o 2;-OP(O)(OR o )2;SiR o 3;-(C 1-4 Linear or branched alkylene)ON(R o )2; or -(C 1-4 Linear or branched alkylene)C(O)ON(R o )2, and each R o are optionally substituted as defined below and independently represent hydrogen, C 1-8 Aliphatic, -CH2Ph, -O(CH2) 0-1Ph, or a 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; or, notwithstanding the above definition, two independently occurring R o together with their intervening atom(s) form a 3-12 membered saturated, partially unsaturated, or aryl monocyclic or polycyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, which may be optionally substituted as defined below.

[0044] R o (or two independently occurring R o Preferred monovalent substituents on the ring (formed by any of the intervening atoms) are independently halogen, -(CH) 0-2 R ● , -(Halo R ● ), -(CH2) 0-2 OH, -(CH2) 0-2 OR ● , -(CH2) 0-2 CH(OR ● )2;-O(HaloR ● ), -CN, -N3, -(CH2) 0-2 C(O)R ● , -(CH2) 0-2 C(O)OH, -(CH2) 0-2 C(O)OR ● , -(CH2) 0-4 C(O)N(R o )2;-(CH2) 0-2 S.R. ● , -(CH2) 0-2 SH, -(CH2) 0-2 NH2, -(CH2) 0-2 NHR ● , -(CH2) 0-2 NR ● 2, -NO2, -SiR ● 3. -OSiR ● 3. -C(O)SR ● , -(C 1-4 Linear or branched alkylene)C(O)OR ● Or -SSR ● And each R ●is unsubstituted or, if preceded by "halo", is substituted only by one or more halogens, C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 R is independently selected from Ph, or a 5-6 membered saturated ring, a partially unsaturated ring, or an aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. o Suitable divalent substituents on a saturated carbon atom of include ═O and ═S.

[0045] Suitable divalent substituents on a saturated carbon atom of an "optionally substituted" group include the following: =O, =S, =NNR * 2, =NNHC(O)R * , =NNHC(O)OR * , =NNHS(O)2R * , =NR * , =NOR * , -O(C(R * 2)) 2-3 O- or -S(C(R * 2)) 2-3 S- is listed, and each R * is hydrogen, optionally substituted as defined below, 1-6 An aliphatic or unsubstituted 5-6 membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. A preferred divalent substituent attached to a vicinal substitutable carbon of an "optionally substituted" group is -O(CR * 2) 2-3 O-, and each independently occurring R * is hydrogen, optionally substituted as defined below 1-6 It is selected from an aliphatic or unsubstituted 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0046] R * Suitable substituents on the aliphatic group include halogen, -R ● , -(Halo R ●), -OH, -OR ● , -O(HaloR ● ), -CN, -C(O)OH, -C(O)OR ● , -NH2, -NHR ● , -NR ● 2 or -NO2, where each R ● is unsubstituted or, if preceded by "halo", is substituted only by one or more halogens, independently C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 Ph, or a 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0047] Suitable substituents on a substitutable nitrogen of an "optionally substituted" group include -R†, -NR†2, -C(O)R†, -C(O)OR†, -C(O)C(O)R†, -C(O)CH2C(O)R†, -S(O)2R†, -S(O)2NR†2, -C(S)NR†2, -C(NH)NR†2 or -N(R†)S(O)2R†, where each R† is independently hydrogen, C which may be substituted as defined below. 1-6 aliphatic, unsubstituted -OPh, or an unsubstituted 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; or, notwithstanding the above definitions, two independent occurrences of R† taken together with their intervening atom(s) form an unsubstituted 3-12 membered saturated ring, partially unsaturated ring, or aryl monocyclic or bicyclic ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0048] Suitable substituents on the aliphatic groups of R† are independently halogen, -R ● , -(Halo R ● ), -OH, -OR ● , -O(HaloR ● ), -CN, -C(O)OH, -C(O)OR ● , -NH2, -NHR ● , -NR ● 2 or -NO2, and each R● is unsubstituted or, if preceded by "halo", is substituted only by one or more halogens, independently C 1-4 Aliphatic, -CH2Ph, -O(CH2) 0-1 Ph, or a 5-6 membered saturated ring, partially unsaturated ring, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0049] As used herein, the term "substantially" refers to the qualitative state of being entirely or nearly entirely to the extent or degree of a feature or characteristic of interest.

[0050] A nomenclature for ascarosides is sometimes used that includes several prefix letters followed by a pound sign (#) and a number (e.g., ascr#18). This convention is used in the scientific literature, and one of skill in the art will understand that each such name is associated with a specific chemical structure of a known composition and will readily understand the structure of a molecule depicted using this nomenclature. Unless otherwise specified, all compound identifiers of this form used herein follow the definitions set forth in the C. elegans Small Molecule Identifier Database (SMID-DB), maintained at http: / / www.smid-db.org.

[0051] In the drawings, features are not necessarily drawn to scale, emphasis instead generally being placed upon illustrating principles of the disclosed compositions and methods, and not intended to be limiting. For clarity, not every component may be labeled in the drawings. In the following description, various embodiments are described with reference to the following drawings: [Brief description of the drawings]

[0052] [Figure 1A] 1 is a graph showing the weight change between strawberries treated with an ascaroside composition and untreated strawberries. [Figure 1B]1 is a photograph showing the change in appearance of strawberries treated with an ascaroside composition compared to untreated strawberries. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0053] Spoilage of many plant-based products can be due to damage caused by microorganisms such as bacteria, fungi, molds and viruses, but also other processes such as excessive ripening or blemishes. Microorganisms accelerate the deterioration of plant-based products through structural breakdown. As they grow, microorganisms such as bacteria, fungi and molds release enzymes that accelerate the spoilage process. Furthermore, some microbial growth in and / or on plant-based products can cause food poisoning in people who consume the contaminated plant-based products.

[0054] As used herein, the term "microorganism" refers to bacteria, fungi, viruses, parasites and / or oomycetes. As used herein, the term "microbial growth" refers to the growth of microorganisms in and / or on the surface of a plant-based product. As used herein, the term "pathogen" refers to a disease-causing microorganism. As used herein, the term "human pathogen" refers to a pathogen that causes disease in humans.

[0055] Compositions and methods are provided for inhibiting microbial growth in and / or on a surface of a plant-based product. The compositions include at least one ascaroside. Additional ingredients may include agriculturally acceptable carriers and components for inhibiting microbial growth or reproduction. Methods for treating a plant-based product with a composition comprising one or more ascarosides include dipping the plant-based product, spraying the plant-based product, or dip-coating the plant-based product. Treating the plant-based product with a composition comprising one or more ascarosides prevents or inhibits microbial growth in and / or on a surface of the plant-based product.

[0056] As used herein, the term "plant-based product" refers to a product produced by a plant (e.g., fruits) or a product obtained by harvesting all or part of a plant (e.g., vegetables, sprouts, flowers, and grasses). As used herein, the term "produce" refers to an edible product obtained from a plant. Exemplary produces include fruits and vegetables.

[0057] The compositions and methods of the present invention inhibit the growth and / or reproduction of microorganisms, particularly food-borne human pathogens, on plant-based products. In some embodiments, the microorganisms include human pathogens such as viruses, bacteria, fungi, parasites and / or oomycetes. Exemplary food pathogens include disease-causing bacteria such as Salmonella, Clostridium perfringens, Campylobacter, Staphylococcus aureus (Staph), Escherichia coli, Listeria, etc. In some embodiments, the microorganisms include bacteria, fungi and / or oomycetes that cause food spoilage.

[0058] Plant-based products that can be treated with a composition comprising at least one ascaroside include, but are not limited to, fruits, vegetables, lettuce, sprouts, flowers, grasses, and products made from these items.

[0059] Exemplary vegetables that can be treated with the methods of the present disclosure include, but are not limited to, stem-feeding vegetables (e.g., asparagus, kohlrabi), leaf-feeding vegetables (e.g., spinach, lettuce, kale, cabbage), flower or sprout-feeding vegetables (e.g., cauliflower, broccoli, artichoke), root / tuber-feeding vegetables (e.g., carrots, radishes, turnips, beets, potatoes, sweet potatoes), bulb-feeding vegetables (e.g., onion, garlic, leeks, fennel), fruit-feeding vegetables (e.g., tomatoes, cucumbers, eggplant, zucchini, squash, pumpkin), and seed-feeding vegetables (e.g., green beans, string beans, kidney beans, peas, corn). Exemplary fruits that can be treated with the methods of the present disclosure include, but are not limited to, berries (e.g., blueberries, raspberries, blackberries, strawberries, grapes), citrus fruits (e.g., oranges, lemons, limes, grapefruit, mandarins, kumquats), stone fruits (e.g., peaches, avocados, cherries, mangoes, plums, nectarines), pome fruits (e.g., apples, pears), melons (e.g., watermelon, cantaloupe, casaba melon, honeydew melon), and tropical fruits (e.g., bananas, guavas, papayas, pomegranates, kiwi, pineapple).

[0060] In one aspect, the disclosure provides a method for inhibiting microbial growth in and / or on a vegetable, the method comprising treating the vegetable with a composition comprising one or more ascarosides. In certain embodiments, the vegetable treated with the composition comprising one or more ascarosides is characterized as being more resistant to microbial growth on and / or in the tissue of the vegetable as compared to an untreated vegetable.

[0061] In one aspect, the disclosure provides a method of inhibiting microbial growth in and / or on a fruit, the method comprising treating the fruit with a composition comprising one or more ascarosides. In certain embodiments, the fruit treated with the composition comprising one or more ascarosides is characterized as being more resistant to microbial growth on and / or in the tissue of the fruit compared to untreated fruit.

[0062] Ascarosides are secondary metabolites produced by nematodes. Numerous structurally diverse ascaroside structures have been identified in nature, and these molecules are believed to function as an evolutionarily conserved chemical language that nematodes use to control many aspects of their development. Ascarosides are also perceived by other organisms and have been shown to have a variety of effects on many organisms, including bacteria, fungi, plants, and mammals, including humans. In the present disclosure, application of ascarosides to plant-based products is shown to activate and prime the plant's defenses to provide protection against colonization and / or proliferation by non-plant microorganisms. Such protection includes preventing the proliferation of microorganisms in plant tissues and plant products (e.g., fruits and vegetables). The disclosed method of stimulating the plant's innate defense system is a unique tool, for example, to combat microorganisms that invade the plant. When stimulated by the disclosed composition, the defense response of the treated plants and plant products provides protection against pathogens for a period of time, such as weeks.

[0063] Ascarosides are derivatives of the sugar ascarylose, a dideoxy sugar lacking hydroxy groups at positions 3 and 6. Ascarosides have the formula I: [ka] wherein Z is an optionally substituted C 2-40 is an aliphatic group, R a and R b Each of is independently -H or C 1-20 aliphatic, C 1-20 Achill, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-bridged functional group, sulfur-bridged functional group, silicon-bridged functional group, C 2-20 Carbonates (e.g., -C(O)OR c part), C 2-20 Carbamates (e.g., -C(O)N(R c )2 parts), C 2-20 Thioesters (e.g., -C(S)Rc part), C 2-20 Thiocarbonates (e.g., -C(S)OR c part), C 2-20 Dithiocarbonates (e.g., -C(S)SR c part), C 1-20 Thiocarbamates (e.g., -C(S)N(R c 2) an optionally substituted moiety selected from the group consisting of a linkage via a bond or a carbon-containing linker moiety to a sugar moiety, a peptide, a polymer chain, or another ascaroside molecule; R c represents independently at each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; R a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation. In certain embodiments, Z is (i) -CH(CH3)-R 1 where R 1 is an optionally substituted C 1-40 is an aliphatic group; (ii) -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (iii) -CH(CH3)-(CH2) n -CH=CH-COR 2In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (iv) -CH(CH3)-(CH2) n -CH(OH)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (v) -CH(CH3)-(CH2) n -C(O)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (vi)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (vii)-(CH2) n -CH=CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (viii)-(CH2) n -CH(OH)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; or (ix)-(CH2) n -C(O)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 A linkage via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule. In certain embodiments, Z is (x)-CH(CH3)-(CH2) n -CON(R3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xi) -CH(CH3)-(CH2) n -CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xii) -CH(CH3)-(CH2) n -CH(OH)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xiii) -CH(CH3)-(CH2) n -C(O)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xiv)-(CH2) n -CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xv)-(CH2) n -CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xvi)-(CH2) n -CH(OH)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; or (xvii)-(CH2) n -C(O)-CH-CON(R 3)2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 A linkage to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0064] In certain embodiments, R a is -H.

[0065] In certain embodiments, R b is -H.

[0066] In certain embodiments, R a and R b are identical. In certain embodiments, R a and R b are both -H.

[0067] In certain embodiments, R a and R b are different. In certain embodiments, R a is -H, R b is other than -H. In certain embodiments, R a is other than -H, and R b is -H. In certain embodiments, R a is -H, R b is a paraoxybenzoate ester. In certain embodiments, R a is -H, R b is an indole-3-carboxylic acid ester. In certain embodiments, R a is -H, R b is (E)-2-methyl-2-butenoic acid ester. In certain embodiments, R a is -H, R b is a picolinic acid ester. In certain embodiments, R a is -H, R bis a nicotinate ester. In certain embodiments, R a is -H, R b is (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4-oxobutanoic acid ester. In certain embodiments, R a is -H, R b is 4-((4-hydroxyphenethyl)amino)-4-oxobutanoic acid ester.

[0068] In certain embodiments, R a and R b are both -H and Z is selected from the formulas defined in (i) to (ix) above. a and R b are both -H and Z is according to formula (i) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (ii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (iii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (iv) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (v) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (vi) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (vii) above. a and R b are both -H and Z conforms to formula (viii) above. a and R b are both -H and Z conforms to formula (ix) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (x) above. In certain embodiments, Ra and R b are both -H and Z conforms to formula (xi) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xii) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xiii) above. a and R b are both -H and Z is according to formula (xiv) above. a and R b are both -H and Z conforms to formula (xv) above. In certain embodiments, R a and R b are both -H and Z conforms to formula (xvi) above. In certain embodiments, R a and R b are both -H and Z is according to formula (xvii) above.

[0069] In certain embodiments, R 2 is -H. In certain embodiments, R 2 is a metal cation. In certain embodiments, R 2 is an organic cation (e.g., a nitrogen- or phosphorus-centered cationic group). In certain embodiments, R 2 is an optionally substituted C 1-20 In certain embodiments, R 2 is an optionally substituted C 1-12 In certain embodiments, R 2 is an optionally substituted C 1-8 In certain embodiments, R 2 is an optionally substituted C 1-6 In certain embodiments, R 2 is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. 2 is an optionally substituted aromatic group. In certain embodiments, R 2is a glycoside. In certain embodiments, R 2 comprises an amino acid. In certain embodiments, R 2 comprises a peptide. In certain embodiments, R 2 contains nucleotides.

[0070] In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; a , R b and R 2 Each of the above is defined as a genus and subgenera herein.

[0071] In certain embodiments, the ascaroside is [ka] wherein x, R a and R b Each of the above is defined as a genus and subgenera herein.

[0072] In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; a , R b and R 2 Each of the above is defined as a genus and subgenera herein.

[0073] In certain embodiments, the ascaroside is [ka] wherein y, R a and R b Each of the above is defined as a genus and subgenera herein.

[0074] In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; 2 are defined above and are of genus and subgenera herein.

[0075] In certain embodiments, the ascaroside is [ka] where x is as defined above and in the genera and subgenera herein.

[0076] In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; 2 are defined above and are of genus and subgenera herein.

[0077] In certain embodiments, the ascaroside is [ka] where y is as defined above and in the genera and subgenera herein.

[0078] In certain embodiments, the ascaroside is [ka] wherein x is an integer from 1 to 22; a , R b and R 3 Each of the above is defined as a genus and subgenera herein.

[0079] In certain embodiments, the ascaroside is [ka] wherein x and R 3 Each of the above is defined as a genus and subgenera herein.

[0080] In certain embodiments, the ascaroside is [ka] wherein y is an integer from 1 to 20; a , R b and R 3 Each of the above is defined as a genus and subgenera herein.

[0081] In certain embodiments, the ascaroside is [ka] wherein y and R 3 Each of the above is defined as a genus and subgenera herein.

[0082] In one embodiment, ascarosides useful in the context of the present disclosure have the general structure (I), where Z is -CH(CH)-(CH). n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 They are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides and can be used to inhibit the growth of human pathogens in or on the surface of plants.

[0083] In one embodiment, ascarosides useful in the context of the present disclosure have the general structure (I), where Z is -CH(CH)-(CH). n -CH=CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0084] In certain embodiments, x in any of the structures herein is an integer between 2 and 18, inclusive. In certain embodiments, x in any of the structures herein is an integer between 4 and 10, inclusive. In certain embodiments, x in any of the structures herein is an integer between 6 and 12, inclusive. In certain embodiments, x in any of the structures herein is an integer between 5 and 9, inclusive. In certain embodiments, x in any of the structures herein is 7, 8, or 9. In certain embodiments, x in any of the structures herein is 6. In certain embodiments, x in any of the structures herein is 7. In certain embodiments, x in any of the structures herein is 8. In certain embodiments, x in any of the structures herein is 9. In certain embodiments, x in any of the structures herein is 10. In certain embodiments, x in any of the structures herein is 11. In certain embodiments, x in any of the structures herein is 12.

[0085] In certain embodiments, x in any of the structures herein is an integer greater than 5. In certain embodiments, x in any of the structures herein is an integer greater than 6, greater than 7, greater than 9, or greater than 10. In certain embodiments, x in any of the structures herein is an integer between 10 and 20.

[0086] In certain embodiments, provided ascaroside compositions comprise a mixture of ascarosides that differ only in the value of x (i.e., the composition comprises a mixture of analogs having side chains of different lengths). In certain embodiments, such compositions are characterized in that the average value of x in the composition is from about 2 to about 20. In certain embodiments, such compositions are characterized in that the average value of x in the composition is from about 3 to about 10, from about 4 to about 12, from about 6 to about 10, or from about 7 to about 9. In certain embodiments, such compositions are characterized in that the average value of x in the composition is greater than about 4, greater than about 5, greater than about 6, greater than about 7, or greater than about 8. The average value of x in such compositions is 1 This can be determined by a variety of methods well known in the art, including, but not limited to, analyzing the mixture by 1 H NMR spectroscopy, mass spectrometry, high performance liquid chromatography, and the like.

[0087] In certain embodiments, y in any of the structures herein is an integer between 2 and 18, inclusive. In certain embodiments, y in any of the structures herein is an integer between 4 and 10, inclusive. In certain embodiments, y in any of the structures herein is an integer between 6 and 12, inclusive. In certain embodiments, y in any of the structures herein is an integer between 5 and 9, inclusive. In certain embodiments, y in any of the structures herein is 7, 8, or 9. In certain embodiments, y in any of the structures herein is 6. In certain embodiments, y in any of the structures herein is 7. In certain embodiments, y in any of the structures herein is 8. In certain embodiments, y in any of the structures herein is 9. In certain embodiments, y in any of the structures herein is 10. In certain embodiments, y in any of the structures herein is 11. In certain embodiments, y in any of the structures herein is 12.

[0088] In certain embodiments, y in any of the structures herein is an integer greater than 5. In certain embodiments, y in any of the structures herein is an integer greater than 6, greater than 7, greater than 9, or greater than 10. In certain embodiments, y in any of the structures herein is an integer between 10 and 20.

[0089] In certain embodiments, provided ascaroside compositions comprise a mixture of ascarosides that differ only in the value of y (i.e., the composition comprises a mixture of analogs having side chains of different lengths). In certain embodiments, such compositions are characterized in that the average value of y for the compositions is from about 2 to about 20. In certain embodiments, such compositions are characterized in that the average value of y for the compositions is from about 3 to about 10, from about 4 to about 12, from about 6 to about 10, or from about 7 to about 9. In certain embodiments, such compositions are characterized in that the average value of y for the compositions is greater than about 4, greater than about 5, greater than about 6, greater than about 7, or greater than about 8. The average value of y for such compositions is 1 This can be determined by a variety of methods well known in the art, including, but not limited to, analyzing the mixture by 1 H NMR spectroscopy, mass spectrometry, high performance liquid chromatography, and the like.

[0090] In one embodiment, ascarosides useful for the present disclosure have the general structure (I), where Z is -CH(CH)-(CH). n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 They are aliphatic groups, optionally substituted aromatic groups, glycosides, amino acids, peptides or nucleotides and can be used to inhibit the growth of human pathogens in or on the surface of plants.

[0091] In one embodiment, ascarosides useful for the present disclosure have the general structure (I), where Z is -CH(CH)-(CH). n -CH=CH-COR 2In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 It may be an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0092] Particular ascarosides useful in the present disclosure include, but are not limited to, ascr#7 and ascr#18. [ka]

[0093] In certain embodiments, the ascarosides used in the provided methods and compositions are selected from the group consisting of ascr#9, ascr#12, ascr#14, ascr#1, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, the ascarosides used in the provided methods are selected from the group consisting of ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, the ascarosides used in the provided methods are selected from the group consisting of ascr#9, ascr#14, ascr#10, and ascr#18.

[0094] In certain embodiments, the ascaroside used in the provided methods and compositions is selected from the group consisting of ascr#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of bhas#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, the ascaroside used in the provided methods is selected from the group consisting of oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0095] In certain embodiments, the ascaroside used in the methods and compositions provided is selected from the group consisting of bhas#9, bhas#10, bhas#16, bhas#18, bhas#22, bhas#24, bhas#26, bhas#28, bhas#30, bhas#32, bhas#34, bhas#36, bhas#38, bhas#40, and bhas#42.

[0096] In certain embodiments, the ascaroside used in the methods and compositions provided is selected from the group consisting of bhos#10, bhos#16, bhos#18, bhos#22, bhos#24, bhos#26, bhos#28, bhos#30, bhos#32, bhos#34, bhos#36, bhos#38, bhos#40, and bhos#42.

[0097] In certain embodiments, the ascarosides used in the methods and compositions provided are selected from the group consisting of ascr#18, oscr#16, oscr#17, oscr#15, bhas#18, bhos#16, glas#18, dhas#18, ibha#18, ibho#16, icas#18, icos#15, icos#16, and any combination of two or more thereof.

[0098] Ascarosides can be obtained from natural sources (e.g., nematodes) or can be synthetically prepared. Ascarosides can be synthetically prepared, for example, by converting 1-O-substituted rhamnose to 1-O-substituted ascarylose. An exemplary method for preparing ascarosides includes providing 1-O-substituted rhamnose as a raw material, forming a mono-sulfonate ester at the 3-OH group of the raw material, and treating the mono-sulfonate ester with a hydride source to form 1-O-substituted ascarylose. In certain embodiments, the formation of the mono-sulfonate ester is carried out at the 2- or 4-position of the rhamnose raw material without the use of a hydroxy protecting group on the substrate. In certain embodiments, such methods include contacting the raw material with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride, or similar reagent) in the presence of a Lewis acid. Specific details regarding the synthesis of 1-O-substituted ascarylose can be found in PCT Application No. PCT / US2021 / 056981, which is incorporated herein by reference.

[0099] According to certain embodiments, microbial growth in and / or on the surface of a plant-based product can be inhibited by treating the plant-based product with an ascaroside of structure (I).

[0100] The method of treating the plant-based product with the ascaroside is not particularly limited. The plant-based product can be treated at any stage from pre-harvest to harvest to post-harvest. The plant-based product can be treated with the ascaroside prepared as a solid or via the ascaroside prepared as a liquid (e.g., a suspension, emulsion, or solution, such as an aqueous solution). The ascaroside formulation can consist / essentially of the ascaroside (e.g., together with a solvent or solvent / co-solvent mixture) or can include any number of additional components.

[0101] Prior to use, the ascarosides used in the compositions of the present disclosure may be dissolved in water to form an aqueous solution of the ascaroside. However, some types of ascarosides have limited solubility in water. Therefore, it may be necessary to first dissolve the ascaroside in a co-solvent that is water-miscible and acceptable for use in plant-based products intended for human consumption. A variety of water-miscible solvents are known and can be used for this purpose. Preferred co-solvents include ethanol and propylene glycol. In one embodiment, a stock solution of the ascaroside in ethanol can be prepared. In one embodiment, a stock solution of the ascaroside in propylene glycol can be prepared. This stock solution is added to a suitable amount of water to prepare an aqueous solution of the ascaroside. As used herein, "aqueous solution" includes solutions that primarily contain water as the solvent and optionally contain one or more co-solvents in amounts up to about 45%, up to about 40%, up to about 35%, up to about 30%, up to about 25%, up to about 20%, up to about 15%, up to about 10%, up to about 5%, up to about 1%, or up to about 0.1% by volume.

[0102] In one embodiment, a plant-based product can be treated with an ascaroside composition (e.g., an aqueous solution of one or more ascarosides) by immersing the plant-based product in the ascaroside composition. The plant-based product can be simply immersed or immersed with gentle agitation (e.g., in circulation of the liquid via a pump or rotating drum such that the plant-based product is in contact with the ascaroside solution). The plant-based product is immersed in the ascaroside solution for a time sufficient to allow the ascarosides to enter the product. Typically, the plant-based product is immersed for about 1 minute to about 12 hours (e.g., about 5 minutes to about 6 hours, or about 30 minutes to about 3 hours, or about 6 hours to about 12 hours), although such times are not intended to be limiting and longer or shorter time ranges can be used in some embodiments. In certain embodiments, the plant-based product is immersed in a solution containing one or more ascarosides for about 1 minute, about 5 minutes, about 10 minutes, about 20 minutes, about 30 minutes, about 45 minutes, about 1 hour, about 2 hours, about 3 hours, about 4 hours, about 5 hours, about 6 hours, about 7 hours, about 8 hours, about 9 hours, about 10 hours, about 11 hours, or about 12 hours. In some embodiments, the plant-based product is washed with a solution containing one or more ascarosides. During the washing process, the plant-based product can be contacted with the ascaroside solution for up to about 0.5 seconds, up to about 1 second, up to about 5 seconds, up to about 10 seconds, up to about 30 seconds, or up to about 60 seconds.

[0103] The plant-based product can be soaked during harvest or after harvest. If during harvest, a dump tank (container filled with water) can be used while collecting the plant-based product. In this tank, water is used to wash the plant-based product while simultaneously inhibiting blemishes on the product. In one embodiment, the water in the dump tank contains one or more ascarosides. Alternatively, if after harvest, the plant-based product can be placed in a container with a composition containing one or more ascarosides. Thus, soaking can be performed at various times after harvest, such as immediately after an item is harvested (e.g., by adding directly to a dump tank containing one or more ascarosides) or immediately after harvest (e.g., when the crop is removed from the field (or greenhouse) where it is grown, the individual items can be transferred to a container containing a composition containing one or more ascarosides (or such a composition can be added to a container containing the harvested plant-based product)). After harvest, the timing can be varied and in some embodiments, the plant-based product can be treated shortly after harvest (e.g., within 24 hours after harvest). In further embodiments, the treatment may be delayed such that the plant-based product is soaked at a later point in time, for example after transport to a processing center or after transport to a retail store.

[0104] The ascaroside solution, when used to soak a plant-based product, has an ascaroside concentration ranging from 1 nM to about 1 mM. Exemplary concentrations of the ascaroside solution include 1 nM, 10 nM, 50 nM, 100 nM, 500 nM, 1 μM, 2 μM, 3 μM, 4 μM, 5 μM, and 10 μM. Exemplary ranges of ascaroside concentrations of the ascaroside solution include 1 nm to 10 μm, 10 nM to 5 μm, 50 nM to 3 μm, and 100 nM to 1 μm. When the ascaroside solution contains more than one ascaroside, the term "ascaroside concentration" refers to the total concentration of all ascarosides in the solution.

[0105] In one embodiment, the plant-based product may be treated with an ascaroside coating formulation (e.g., a liquid or powder composition containing one or more ascarosides) via a spraying method. Such spraying methods can be performed pre-harvest (e.g., within about one week or within one to two days prior to harvest), during harvest, or post-harvest (up to six weeks after harvest).

[0106] In the pre-harvest case, the ascaroside coating formulation can be applied to the plant-based product before the product is ready for harvest. For example, the ascaroside coating formulation can be applied to the plant-based product shortly after the product emerges on the relevant plant or tree. Alternatively, or in addition, the ascaroside coating formulation can be applied to the plant or tree that produces the plant-based product before the product is grown. Application of the ascaroside coating formulation to the plant that produces the plant-based product can provide protection from microorganisms on the plant surface. This protection can also be provided to the plant-based product obtained from the treated plant.

[0107] In some embodiments, when the plant-based product is harvested, the plant-based product may be passed through a sprayer containing a composition containing one or more ascarosides, and the plant-based product may be contacted with a spray or composition containing one or more ascarosides after it is removed from the field (or greenhouse) in which it is grown. After harvest, the timing may be varied, and in some embodiments, the plant-based product may be sprayed shortly after harvest (e.g., within 24 hours after harvest). In further embodiments, the treatment may be delayed so that the plant-based product is sprayed at a later time, for example, after transportation to a processing center or after transportation to a retail store. In still further embodiments, the plant-based product may be sprayed (e.g., continuously / periodically) at the time of sale, for example, by a mister. Again, during such spray treatment methods, the plant-based product may remain primarily stationary or may be agitated.

[0108] Coating of the plant-based product can be accomplished by any known means of spraying a composition onto the plant-based product. In contrast to dipping, spraying methods typically use a smaller (e.g., minimal) amount of liquid to provide a protected product that is stable during storage and transportation. The ascaroside solution used for spraying the plant-based product has a concentration ranging from about 1 ppb to about 500 ppm. For example, the concentration of ascaroside used for spraying the plant-based product can be 1 ppb, 10 ppb, 50 ppb, 100 ppb, 250 ppb, 500 ppb, 1 ppm, 2 ppm, 3 ppm, 5 ppm, 10 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 40 ppm, 50 ppm, 100 ppm, 200 ppm, or 500 ppm.

[0109] The dipping and spraying methods provided herein are not intended to be limiting. Rather, any method of contacting a plant-based product with an ascaroside in solid or liquid (e.g., solution) form can be used and is intended to be encompassed by the present disclosure. For example, in some embodiments, packaging materials, stickers, or adhesives can be treated or formulated to include an ascaroside and then contacted with the plant-based product being treated, for example, by applying the packaging material or sticker to the individual product. In some embodiments, coatings can be applied periodically to certain plant-based products, and ascarosides can be incorporated into such coatings. As an example, edible waxes and oils are commonly applied to fruits, such as apples, citrus fruits, and root vegetables, and ascarosides can be applied to these, for example, via incorporation into the wax or oil formulation.

[0110] In one embodiment, the method provided includes continuously contacting the plant-based product with a composition comprising one or more ascarosides during transportation, sale or thereafter, or during use by the consumer, such as by continuously immersing cut flowers, ornamental leaves, or stems of fresh herbs in an ascaroside-containing solution, or by continuously contacting the stems or other parts of cut flowers, ornamental leaves, or fresh herbs with an absorbent material moistened with an ascaroside-containing solution. In another embodiment, the ascaroside composition may be provided packaged with ornamental plant material intended for use by the consumer, such as by adding the ascaroside composition to vase water. In certain embodiments, the ascarosides may be incorporated into nutritional compositions containing sugars or similar substances that are typically provided in bouquets and intended to be added to vase water to make cut flowers and leaves last longer.

[0111] The ascarosides used in the compositions of the present disclosure may be blended with other materials for application to plant materials prior to use. Examples include waxes, oils, latex, shellac, polymeric films, adhesives, or coatings that are coated on or placed in contact with the produce to enhance appearance, extend shelf life, control moisture loss, attach labels, etc. In certain embodiments, the methods provided herein may include adding the ascaroside to such compositions or formulations. If the ascaroside is not directly soluble or miscible in such formulations, it may be necessary to first dissolve the ascaroside in a co-solvent that is miscible with the formulation and acceptable for use in plant-based products intended for human consumption. A variety of food-safe solvents are known and can be used for this purpose. Preferred co-solvents include ethanol and propylene glycol. In one embodiment, a stock solution of the ascaroside in ethanol can be prepared. In one embodiment, a stock solution of the ascaroside in propylene glycol can be prepared. The stock solution is added to a suitable amount of the coating formulation to prepare the ascaroside-containing formulation. In one embodiment, a mixture of one or more ascarosides in a food-safe oil is provided. In one embodiment, a mixture of one or more ascarosides in a food-safe wax is provided. In one embodiment, a mixture of one or more ascarosides in a food-safe adhesive is provided. In one embodiment, a mixture of one or more ascarosides in a food-safe paint or stain is provided.

[0112] According to the present disclosure, the treatment of the plant-based product is applied at a rate that provides the treated plant-based product with an ascaroside content of about 0.0001 ppm to about 100 ppm by weight. In certain embodiments, such plant-based products are treated to contain about 0.001 to about 10 ppm of ascarosides. In certain embodiments, such fruits or vegetables are treated to contain about 0.01 to about 1 ppm of ascarosides. In certain embodiments, such fruits or vegetables are treated to contain about 0.1 to about 5 ppm of ascarosides. In certain embodiments, such fruits or vegetables are treated to contain about 0.0001 to about 0.001 ppm of ascarosides. In certain embodiments, such fruits or vegetables are treated to contain about 0.001 to about 0.01 ppm of ascarosides. In certain embodiments, such fruits or vegetables are treated to contain about 0.01 to about 0.1 ppm of ascarosides. In certain embodiments, such plant-based products contain from about 0.2 to about 5 ppm of ascarosides. In certain embodiments, such plant-based products contain from about 1 to about 10 ppm of ascarosides. In certain embodiments, such plant-based products contain from about 2 to about 5 ppm of ascarosides. In certain embodiments, such plant-based products contain from about 0.1 to about 1 ppm of ascarosides. In certain embodiments, such plant-based products contain from about 0.5 to about 2.5 ppm of ascarosides. In certain embodiments, the method includes treating the plant-based product, drying the plant-based product, storing the plant-based product, and optionally transporting the plant-based product to a retail store. In some embodiments, such ascaroside effects are exhibited in the plant-based product immediately after treatment and may persist for a period of time after treatment, such as at least about 1 day, at least about 2 days, at least about 3 days, at least about 4 days, at least about 5 days, at least about 6 days, at least about 1 week, at least about 2 weeks, at least about 3 weeks, or at least about 4 weeks.

[0113] In one embodiment of the present disclosure, it has been found that contacting a plant-based product with an ascaroside solution can inhibit microbial growth in and / or on the surface of the product. In some embodiments, such inhibition can provide a longer shelf life for the treated plant-based product. Without wishing to be bound by any particular theory, it is believed that the protective effect of ascaroside treatment is due to the upregulation of plant defense genes in the presence of ascarosides.

[0114] Biofilm formation is one of the main defense strategies used by bacteria against hostile environmental conditions. Biofilm formation by bacteria on or within plant-based products can provide a protected environment in which pathogens can colonize and multiply. Without wishing to be bound by any particular theory, it is believed that ascarosides can affect the ability of bacteria to form biofilms. By inhibiting biofilm formation, ascarosides can remove one of the main defense mechanisms of bacteria.

[0115] Treatment of plant-based products with an ascaroside solution can control a variety of human pathogens, including, but not limited to, Salmonella enterica, Salmonella serovar Muenchen, Salmonella Saintpaul, Escherichia coli O157:H7, Escherichia coli O157:NM, Escherichia coli 0121, Escherichia coli O104:H4, and Listeria monocytogenes.

[0116] It is theorized that after immersion in the ascaroside solution, the plant-based product absorbs about 0.01 to about 100 ppm of ascarosides. The amount of ascaroside absorbed in the plant-based product is a function of, for example, the concentration of ascarosides in the ascaroside solution, the immersion time, and the type of product. Thus, the amount of ascarosides present in the treated plant-based product can be varied by adjusting these parameters. Typically, the plant-based product is treated with the ascaroside (e.g., ascaroside solution) at ambient temperature and pressure. In some embodiments, the plant-based product is treated with the ascaroside (e.g., ascaroside solution) at a temperature and / or pressure greater than ambient temperature and / or pressure. Treatment of the plant-based product at a temperature and / or pressure greater than ambient temperature and / or pressure may kill some or all human pathogens that may be present in and / or on the surface of the plant-based product.

[0117] The plant-based product treatments provided herein have been shown to reduce or prevent microbial contamination without the need for additional types of treatment. While the plant-based product treatments provided herein may be the only microbial reduction treatments performed, in other embodiments, these treatments can be used simultaneously with one or more known methods for reducing or eliminating microbial contamination, including, but not limited to, treatment with acidic electrolyzed water, ozonated water, chlorine dioxide, trisodium phosphate, calcium hypochlorite (bleaching powder), and sodium hypochlorite (bleach).

[0118] According to the present disclosure, the shelf life of a plant-based product can be extended by contacting the product with a composition comprising an ascaroside after harvesting. The harvested product can be treated with the ascaroside composition. Treatment of the harvested product with the ascaroside composition extends the shelf life of the ascaroside-treated product compared to the corresponding untreated vegetable.

[0119] Embodiments of the present invention include the following.

[0120] Embodiment 1: A method of inhibiting the spread of microbial growth in and / or on a plant-based product, the method comprising treating the plant-based product with a composition comprising one or more ascarosides.

[0121] Embodiment 2: The method of embodiment 1, wherein the microbial growth that is inhibited is microbial growth that is pathogenic to humans.

[0122] Embodiment 3: The method of embodiment 1, wherein the microbial growth that is inhibited is an enteric pathogen.

[0123] Embodiment 4: The method of embodiment 1, wherein the microbial growth that is inhibited is bacterial growth.

[0124] Embodiment 5: The method of embodiment 1, wherein the microbial growth that is inhibited is fungal growth.

[0125] Embodiment 6: The method of embodiment 1, wherein the microorganism belongs to a genus selected from the group consisting of Salmonella, Listeria, and Escherichia, Clostridium, and Campylobacter.

[0126] Embodiment 7: The method of embodiment 1, wherein the microbial growth that is inhibited is microbial growth associated with spoilage of the plant-based product.

[0127]

[0023] Embodiment 8: The method of embodiment 1, wherein the microorganism comprises a mold.

[0128] Embodiment 9: A method of extending the shelf life of a plant-based product, comprising contacting the plant-based product with a composition comprising one or more ascarosides.

[0129] Embodiment 10: The method of any of the preceding embodiments, wherein the plant-based product is a vegetable.

[0130] Embodiment 11: The method of embodiment 10, wherein the vegetables are selected from the group consisting of stem-eating vegetables, leaf-eating vegetables, flower-eating vegetables, root / tuber-eating vegetables, bulb-eating vegetables, fruit-eating vegetables, and seed-eating vegetables.

[0131] Embodiment 12: The method according to any one of embodiments 1 to 9, wherein the plant-based product is a fruit.

[0132] Embodiment 13: The method of embodiment 12, wherein the fruit is selected from the group consisting of berries, citrus fruits, stone fruits, pome fruits, melons, and tropical fruits.

[0133] Embodiment 14: The one or more ascarosides has structure (I): [ka] wherein Z is an optionally substituted C 2-40 is an aliphatic group, R a and R b Each of is independently -H or C 1-20 aliphatic, C 1-20 Achill, C 1-20 Heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus-bridged functional group, sulfur-bridged functional group, silicon-bridged functional group, C 2-20 Carbonates (e.g., -C(O)OR c part), C 2-20 Carbamates (e.g., -C(O)N(R c )2 parts), C 2-20 Thioesters (e.g., -C(S)R c part), C 2-20 Thiocarbonates (e.g., -C(S)OR c part), C 2-20 Dithiocarbonates (e.g., -C(S)SR c part), C 1-20 Thiocarbamates (e.g., -C(S)N(R c2) an optionally substituted moiety selected from the group consisting of a linkage via a bond or a carbon-containing linker moiety to a sugar moiety, a peptide, a polymer chain, or another ascaroside molecule; R c represents independently at each occurrence -H, optionally substituted C 1-12 Aliphatic, optionally substituted C 1-12 is selected from heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymeric chain, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety; R a and R b may be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, optionally containing one or more sites of unsaturation.

[0134] Embodiment 15: Z is (i) -CH(CH3)-R 1 where R 1 is an optionally substituted C 1-40 is an aliphatic group; (ii) -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (iii) -CH(CH3)-(CH2) n -CH=CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (iv) -CH(CH3)-(CH2) n -CH(OH)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (v) -CH(CH3)-(CH2) n -C(O)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (vi)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (vii)-(CH2) n -CH=CH-COR 2In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (viii)-(CH2) n -CH(OH)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; or (ix)-(CH2) n -C(O)-CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 15. The method of embodiment 14, wherein the amino acid is selected from the group consisting of a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0135] Embodiment 16: Z is (x)-CH(CH3)-(CH2) n -CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xi) -CH(CH3)-(CH2) n -CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xii) -CH(CH3)-(CH2) n -CH(OH)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xiii) -CH(CH3)-(CH2) n -C(O)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xiv)-(CH2) n -CON(R3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xv)-(CH2) n -CH=CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; (xvi)-(CH2) n -CH(OH)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-20 is linked via a bond or a carbon-containing linker moiety to a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or another ascaroside molecule; or (xvii)-(CH2) n -C(O)-CH-CON(R 3 )2, wherein n is an integer from 1 to 40, and each R 3 are independently -H, optionally substituted C 1-20 Aliphatic groups, optionally substituted C 1-2015. The method of embodiment 14, wherein the ascaroside is selected from the group consisting of a heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascaroside molecule via a bond or a carbon-containing linker moiety.

[0136] Embodiment 17: R a and R b The method of any one of embodiments 14 to 16, wherein each is -H.

[0137] Embodiment 18: Z is -CH(CH3)-(CH2) n -CO2R 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 The method according to any one of embodiments 14 to 17, wherein the aryl group is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0138] Embodiment 19: The method of embodiment 18, wherein at least one of the one or more ascarosides is ascr#18.

[0139] Embodiment 20: Z is -CH(CH3)-(CH2) n -CH=CH-COR 2 In the formula, n is an integer from 1 to 40, and R 2 is -H, a metal cation, an optionally substituted C 1-20 The method according to any one of embodiments 14 to 17, wherein the aryl group is an aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide or a nucleotide.

[0140] Embodiment 21: The method of embodiment 20, wherein at least one of the one or more ascarosides is ascr#7.

[0141] Embodiment 22: The method of any one of embodiments 1 to 21, wherein the composition comprising one or more ascarosides is an aqueous soluble composition.

[0142] Embodiment 23: The method according to any one of embodiments 1 to 22, wherein the plant-based product is treated by soaking in a composition comprising one or more ascarosides.

[0143] Embodiment 24: The method of embodiment 23, wherein the plant-based product is immersed in a tank containing a composition comprising the one or more ascarosides during harvest of the plant-based product's crop.

[0144] Embodiment 25: The method of any one of embodiments 23 or 24, wherein the plant-based product is immersed in the composition for about 1 minute to about 6 hours.

[0145] Embodiment 26: The method according to any one of embodiments 1 to 22, wherein the plant-based product is treated by spraying with a composition comprising the one or more ascarosides.

[0146] Embodiment 27: The method of any one of embodiments 1 to 26, wherein the concentration of the one or more ascarosides in the composition is from about 1 ppb to about 50 ppm.

[0147] Embodiment 28: A plant-based product which is protected against microbial growth by treatment with a method according to any one of embodiments 1 to 27.

[0148] Embodiment 29: A plant-based product that has been treated by the method of any one of embodiments 1 to 27, wherein the treated plant-based product has a substantially longer shelf life than a corresponding untreated plant-based product. EXAMPLES

[0149] The following examples illustrate certain embodiments of the invention and are not intended to be limiting.

[0150] Example 1: Treating fruit with ascarosides extends shelf life / delays spoilage Commercially available strawberries were treated with the ascaroside (ascr#18) by immersion in a 100 nM aqueous solution of the ascaroside or a mock solution without the ascaroside. Five strawberries from each treatment group were placed in a glass dish and left uncovered on a bench indoors at ambient temperature and observed for one week. Weights were measured on days 0, 1, 3, 4, 5, 6, and 7 after treatment. A plot of the normalized mass of the two treatment groups over the seven days is shown in Figure 1A. The ascaroside-treated strawberries retained approximately 25% more of their original mass than the untreated group, suggesting a possible slower rate of spoilage and an extended shelf life. Figure 1B shows photographs of the two treatment groups taken on days 0, 3, and 5 after treatment. Both treatment groups spoiled during the study, but it was qualitatively clear that the treated fruits retained a higher quality than the untreated fruits. Similar results were obtained when the fruits were treated by spraying with the ascaroside solution. Example 2: Treatment of Fruit with an Ascaroside-Containing Coating Composition Fresh, uncoated apples were purchased from a supermarket. The apples were washed and the test coatings were applied. The test coatings were prepared as follows:

[0151] Polyethylene: 18.6% oxidized polyethylene (AC680 from Allied Signal, Inc., Morristown, NJ), 3.4% food grade oleic acid (Emersol 6321, Henkel, Cincinnati, OH), 2.8% morpholine, 0.01% polydimethylsiloxane antifoam (SE21, Wacker Silicones Co., Adrian, MI), and the balance was either water (control) or a 1 uM aqueous solution of ascr#18 (ascaroside treatment).

[0152] Candelilla Coating: 18.3% candelilla wax (SP 75, Strahl & Pitsch, Inc., West Babylon, NY), 2.1% oleic acid, 2.4% morpholine, 0.02% polydimethylsiloxane antifoamant, balance is either water (control) or a 1 uM solution of ascr#18 in water.

[0153] Carnauba-shellac coating: 9.5% shellac (R52, Mantrose Haeuser Co., Attleboro, MA), 8.3% carnauba wax (No. 1, Strahl & Pitsch, Inc.), 3.3% morpholine, 1.7% oleic acid, 0.17% NH3, 0.01% polydimethylsiloxane defoamer, balance was either water (control) or a 1uM solution of ascr#18 in water.

[0154] Shellac Coating: 19% shellac, 1.0% oleic acid, 4.4% morpholine, 0.3% NH3, 0.01% polydimethylsiloxane antifoamant, balance is either water (control) or a 1 uM solution of ascr#18 in water.

[0155] Shellac-WPI coating: 13.3% shellac, 3.0% whey protein isolate (BiPRO, Davisco Foods International, Inc., Le Sueur, MN), 3.1% morpholine, 0.7% oleic acid, 0.2% NH3, 0.01% polydimethylsiloxane antifoam, balance was either water (control) or a 1 uM aqueous solution of ascr#18 (ascaroside treatment).

[0156] For coating application, a 1.0 ml aliquot of each coating is spread evenly over the surface of each apple with a latex gloved hand. The effective amount of material applied is 0.6 g per apple. Sixty fruit groups are treated with each formulation described above. The fruits (including the control group) are dried using a pilot plant scale conveyor dryer at 50° C. for 5 minutes. After coating application, the apples are stored at 20° C. and approximately 70% relative humidity for 4 weeks.

[0157] Twenty fruits per treatment were measured for gloss, weight loss and flesh firmness. Five fruits per treatment were used to determine internal O2, CO2 and ethylene. Measurements were performed initially, followed by storage at 20°C for 2 and 4 weeks. The first measurement was performed one day after coating, to allow the fruits to recover from the hot air drying process and to allow the coating to dry completely.

[0158] The compositions, systems, devices, methods, and processes of the present application are contemplated to encompass variations and adaptations developed using information from the embodiments described in this disclosure. Adaptations or modifications of the methods and processes described herein may be made by one of ordinary skill in the relevant art.

[0159] It will be understood that the use of headings in this disclosure is provided for the convenience of the reader. The presence and / or placement of headings is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of this application apply to other embodiments, both alone and in combination, throughout this application.

[0160] Throughout this specification, when compositions, compounds, or products are described as having, including, or comprising certain components, or processes and methods are described as having, including, or comprising certain steps, it is contemplated that there are additionally articles, devices, and systems of the present application that consist essentially of or consist of the recited components, and processes and methods according to the present application that consist essentially of or consist of the recited processing steps.

[0161] It should be understood that the order of steps or order for performing certain actions is immaterial so long as the method described remains operable. Moreover, two or more steps or actions may be performed simultaneously.

[0162] All publications and patent applications mentioned in this specification are indicative of the level of those skilled in the art to which this invention pertains. All publications and patent applications are herein incorporated by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference.

[0163] Although the foregoing invention has been described in some detail by way of illustration and example, for purposes of clarity of understanding, it will be apparent that certain changes and modifications may be practiced which are within the scope of the appended claims.

Claims

1. A method for suppressing the spread of microbial growth in and / or on the surface of a plant-based product, comprising treating the plant-based product with a composition containing one or more ascalosides.

2. The method according to claim 1, wherein the suppressed microbial growth is the growth of a human pathogenic microbial organism.

3. The method according to claim 1, wherein the microbial growth that is suppressed is an intestinal pathogen.

4. The method according to claim 1, wherein the microbial growth to be suppressed is bacterial growth.

5. The method according to claim 1, wherein the microbial growth that is suppressed is fungal growth.

6. The method according to claim 1, wherein the microorganism belongs to a genus selected from the group consisting of Salmonella, Listeria, Escherichia, Clostridium, and Campylobacter.

7. The method according to claim 1, wherein the microbial growth to be suppressed is microbial growth associated with the spoilage of the plant-based product.

8. The method according to claim 1, wherein the microorganism includes mold.

9. A method for extending the shelf life of a plant-based product, comprising contacting the plant-based product with a composition containing one or more ascalosides.

10. The method according to claim 1, wherein the plant-based product is a vegetable.

11. The method according to claim 10, wherein the vegetable is selected from the group consisting of vegetables whose stems are eaten, vegetables whose leaves are eaten, vegetables whose flowers are eaten, vegetables whose roots / tubers are eaten, vegetables whose bulbs are eaten, vegetables whose fruits are eaten, and vegetables whose seeds are eaten.

12. The method according to claim 1, wherein the plant-based product is a fruit.

13. The method according to claim 12, wherein the fruit is selected from the group consisting of berries, citrus fruits, stone fruits, pears, melons, and tropical fruits.

14. The one or more ascalosides mentioned above have structure (I): 【Chemistry 19】 having, wherein Z is optionally substituted C １－２０ , ｃ , ２－２０ , １－２０ , ２－２０ , ２－２０ , ａ , ｃ , １－１２ , ２ , ２－２０ , ２－２０ , ｃ , ｃ , ｂ , ｃ , １－１２ , ｃ , ｃ , ２ is an aliphatic group, R ａ and R ｂ each is, independently, -H, or C １－２０ aliphatic, C １－２０ acyl, C １－２０ heteroaliphatic, aryl, heteroaryl, hydroxy protecting group, phosphorus cross-linked functional group, sulfur cross-linked functional group, silicon cross-linked functional group, C ２－２０ carbonate ester (e.g., -C(O)OR ｃ moiety), C ２－２０ carbamate ester (e.g., -C(O)N(R ｃ ) ２ moiety), C ２－２０ thioester (e.g., -C(S)R ｃ moiety), C ２－２０ thiocarbonate ester (e.g., -C(S)OR ｃ moiety), C ２－２０ dithiocarbonate ester (e.g., -C(S)SR ｃ moiety), C １－２０ thiocarbamide ester (e.g., -C(S)N(R ｃ ) ２ moiety), a sugar moiety, a peptide, a polymer chain, or a moiety selected from the group consisting of a bond or a linkage via a carbon-containing linker moiety to another ascarylose molecule, which is an optionally substituted moiety, R ｃ is, independently, at each occurrence, -H, optionally substituted C １－１２ aliphatic, optionally substituted C １－１２ heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascarylose molecule, selected, R ａ and R ｂ may together form an optionally substituted ring optionally containing one or more heteroatoms and optionally containing one or more unsaturated sites, the method according to any one of claims 1 to 13.

15. Z is (i) - CH(CH ３ )-R １ And in the formula, R １ C is replaced as desired. １－４０ It is an aliphatic group; (ii) -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (iii)-CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (iv)-CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH-CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (v)-CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH-CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (vi)-(CH ２ ) ｎ -CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (vii) - (CH ２ ) ｎ -CH=CH-CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (viii)-(CH ２ ) ｎ -CH(OH)-CH-CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or another ascaloside molecule, either via a bond or a carbon-containing linker moiety; or, (ix) - (CH ２ ) ｎ -C(O)-CH-CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ Aliphatic group, optionally substituted C １－２０ This involves bonding to or linking via a carbon-containing linker moiety to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, glycoside, amino acid, peptide, nucleotide, or another ascaloside molecule. The method according to claim 14, selected from the group consisting of the following.

16. Z is (x)-CH(CH ３ )-(CH ２ ) ｎ -CON(R ３ ) ２ wherein n is an integer from 1 to 40, and each R ３ is independently -H, an optionally substituted C １－２０ aliphatic group, an optionally substituted C １－２０ heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage to another ascarylose molecule via a bond or a carbon-containing linker moiety; (xi)-CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ In the formula, n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (xii)-CH(CH ３ )-(CH ２ ) ｎ -CH(OH)-CH-CON(R ３ ) ２ In the formula, n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (xiii)-CH(CH ３ )-(CH ２ ) ｎ -C(O)-CH-CON(R ３ ) ２ In the formula, n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (xiv)-(CH ２ ) ｎ -CON(R ３ ) ２ In the formula, n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (xv) - (CH ２ ) ｎ -CH=CH-CON(R ３ ) ２ In the formula, n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or another ascaloside molecule, either through bonding or via a carbon-containing linker moiety; (xvi) - (CH ２ ) ｎ -CH(OH)-CH-CON(R ３ ) ２ In the formula, n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ This involves linking to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or another ascaloside molecule, either via bonding or a carbon-containing linker moiety; or (xvii)-(CH ２ ) ｎ -C(O)-CH-CON(R ３ ) ２ In the formula, n is an integer from 1 to 40, and each R ３ These are independently -H, and C as desired. １－２０ Aliphatic group, optionally substituted C １－２０ The linkage is to a heteroaliphatic group, optionally substituted aromatic group, optionally substituted heteroaryl group, polymer chain, amino acid, peptide, nucleotide, or another ascaloside molecule, either by bonding or via a carbon-containing linker moiety. The method according to claim 14, selected from the group consisting of the following.

17. R ａ and R ｂ The method according to claim 14, wherein each of them is -H.

18. Z is -CH(CH ３ )-(CH ２ ) ｎ -CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ The method according to claim 14, wherein the aliphatic group is, optionally, a substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

19. The method according to claim 18, wherein at least one of the one or more ascalosides is ascr#18.

20. Z is -CH(CH ３ )-(CH ２ ) ｎ -CH=CH-CO ２ R ２ In the formula, n is an integer from 1 to 40, and R ２ C is -H, a metal cation, or optionally substituted C １－２０ The method according to claim 14, wherein the aliphatic group is, optionally, a substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

21. The method according to claim 20, wherein at least one of the one or more ascalosides is ascr#7.

22. The method according to claim 14, wherein the composition containing one or more ascalosides is a water-soluble composition.

23. The method according to claim 14, wherein the plant-based product is treated by immersion in a composition containing one or more ascalosides.

24. The method according to claim 23, wherein the plant-based product is immersed in a tank containing a composition comprising one or more ascalosides during the harvesting of the crop of the plant-based product.

25. The method according to claim 14, wherein the plant-based product is immersed in the composition for about 1 minute to about 6 hours.

26. The method according to claim 14, wherein the plant-based product is treated by spraying a composition containing one or more ascalosides.

27. The method according to claim 14, wherein the concentration of one or more ascalosides in the composition is about 1 ppb to about 50 ppm.

28. A plant-based product protected from microbial growth by treatment according to claim 14.

29. A plant-based product processed by the method described in claim 14, wherein the processed plant-based product has a substantially longer shelf life than the corresponding untreated plant-based product.

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