# US 8,784,856 B2 · Meadowfoam-based bioherbicide products

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- Number: US 8,784,856 B2
- Document ID: US8784856B2
- Status: Granted
- Kind: B2
- Application number: 12/664,984
- Filed: 2008-07-21
- Published: 2010-12-16
- Granted: 2014-07-22
- Earliest claimed: 2007-07-19
- Assignees: The State of Oregon Acting by and Through the State Boad of Higher Education on Behalf of Oregon State University
- Applicants: Jan F. Stevens; Stephen Machado; Ralph Reed; Michael S. Martinez
- Inventors: Jan F. Stevens; Stephen Machado; Ralph Reed; Michael S. Martinez
- Web page: https://patentgrep.com/patent/US8784856B2

## CPC

- A01N 25/32: Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
- A01N 25/28: Microcapsules {or nanocapsules}
- A01N 51/00: Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
- A01N 65/00: Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof (containing compounds of determined constitution A01N27/00 - A01N59/00)
- A23B 2/762: Organic compounds containing nitrogen
- A23B 2/767: Organic compounds containing sulfur
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 17/06: Antipsoriatics
- A61P 31/04: Antibacterial agents
- A61P 35/00: Antineoplastic agents
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A23B: PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Particular aspects provide methods for converting glucosinolate in a glucosinolate-containing plant material to glucosinolate breakdown products (GBPs), comprising: providing an amount of processed glucosinolate-containing plant material, the processed material being depleted of oil and glucosinolate converting enzyme activity by virtue of said processing; providing an amount of glucosinolate converting enzyme activity; mixing the processed material with the amount enzyme activity; hydrating the mixture; and incubating the hydrated mixture, wherein the glucosinolates are enzymatically converted to GBPs. Preferably, the processed plant material comprises a oilseed-derived seedmeal material (e.g., meadowfoam seedmeal) from which the oil has been removed by the processing (e.g., solvent extraction and/or heat treatment). In particular embodiments, the glucosinolate converting enzyme activity comprises at least one of a myrosinase activity and a nitrile-forming activity. Additional aspects provide low-fat compositions (e.g., herbicide, fungicide, insecticide, bacteriostatic or bactericidal, cosmetic, cosmeceutical or pharmaceutical) comprising GBPs derived from a glucosinolate-containing plant material.

## Claims

### Claim 1

A method for converting glucosinolate in a glucosinolate-containing plant material to glucosinolate breakdown products (GBPs), comprising:
providing an amount of processed glucosinolate-containing plant material, the processed plant material being depleted of oil and glucosinolate converting enzyme activity by virtue of said processing;
providing an amount of exogenous glucosinolate converting enzyme activity comprising a thioglucosidase;
contacting or mixing the processed glucosinolate-containing plant material with the amount of exogenous glucosinolate converting enzyme activity comprising the thioglucosidase to provide a mixture;
hydrating the mixture; and
incubating the hydrated mixture, wherein the glucosinolates in the processed glucosinolate-containing plant material are enzymatically converted to glucosinolate breakdown products (GBPs) by the exogenously provided glucosinolate converting enzyme activity comprising the thioglucosidase.

### Claim 2 (depends on 1)

The method of claim 1, wherein the processed glucosinolate-containing plant material comprises a oilseed-derived seedmeal material from which the oil has been removed by the processing, and wherein the processing comprises at least one of solvent extraction and heat treatment.

### Claim 3 (depends on 1)

The method of claim 1, wherein the exogenous glucosinolate converting enzyme activity comprises at least one of a myrosinase activity and a nitrile-forming activity.

### Claim 4 (depends on 1)

The method of claim 1, wherein the exogenous glucosinolate converting enzyme activity comprises that of a heterologous plant relative to the processed glucosinolate-containing plant material.

### Claim 5 (depends on 1)

The method of claim 1, wherein providing the exogenous glucosinolate converting enzyme activity comprises providing a plant material having glucosinolate converting enzyme activity.

### Claim 6 (depends on 5)

The method of claim 5, wherein the plant material having glucosinolate converting enzyme activity comprises seed material of a seed oil plant.

### Claim 7 (depends on 6)

The method of claim 6, wherein amount of plant material having glucosinolate converting enzyme activity is present in an amount less than 2 wt %, less than 5 wt %, or less than 10 wt %, relative to the amount of processed glucosinolate-containing plant material.

### Claim 8 (depends on 1)

The method of claim 1, wherein the glucosinolate breakdown products (GBPs), comprise at least one product selected from the group consisting of a glucosinolate-derived isothiocyanate, a glucosinolate-derived nitrile and an acetamide derivative of a glucosinolate-derived nitrile.

### Claim 9 (depends on 8)

The method of claim 8, wherein incubating the hydrated mixture is in the presence of an enzymatic co-factor or agent that promotes formation of the glucosinolate-derived nitrile or acetamide derivative of a glucosinolate-derived nitrile, relative to formation of the glucosinolate-derived isothiocyante.

### Claim 10 (depends on 9)

The method of claim 9, wherein the enzymatic co-factor or agent comprises a metal ion.

### Claim 11 (depends on 10)

The method of claim 10, wherein the metal is at least one selected from the group consisting of Fe2+, Zn2+, Ca2+, Mg2+, Cu2+, and Mn2+.

### Claim 12 (depends on 1)

The method of claim 1, further comprising drying or freeze drying the incubated hydrated mixture.

### Claim 13 (depends on 1)

The method of claim 1, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from at least one plant selected from the group consisting of: Crambe (Crambe abysinnica); Black Mustard; Yellow Mustard (Sinapis alba); Oriental Mustard (Brassica juncea); Broccoli (Brassica oleracea italica); Rapeseed (Brassica napus); Meadowfoam (Limnanthes alba), Radish (Raphanus sativus); Wasabi (Wasabia japonica); Horseradish (Cochlearia Armoracia); Cauliflower; Garden cress (Lepidium sativum); Watercress (Nasturtium officinalis); and Papaya (Carica papaya).

### Claim 14 (depends on 13)

The method of claim 13, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from Meadowfoam (Limnanthes alba).

### Claim 15 (depends on 1)

The method of claim 1, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from the genus Brassicas.

### Claim 16

A method for providing a low-fat composition comprising glucosinolate breakdown products (GBPs) derived from a glucosinolate-containing plant material, comprising:
providing an amount of processed glucosinolate-containing plant material, the processed plant material being depleted of oil and glucosinolate converting enzyme activity by virtue of said processing;
providing an amount of exogenous glucosinolate converting enzyme activity comprising a thioglucosidase;
contacting or mixing the processed glucosinolate-containing plant material with the amount of exogenous glucosinolate converting enzyme activity comprising the thioglucosidase to provide a mixture;
hydrating the mixture; and
incubating the hydrated mixture, wherein the glucosinolates in the processed glucosinolate-containing plant material are enzymatically converted to glucosinolate breakdown products (GBPs) by the exogenously provided glucosinolate converting enzyme activity comprising the thioglucosidase to provide for a low-fat composition comprising glucosinolate breakdown products (GBPs) derived from a glucosinolate-containing plant material.

### Claim 17 (depends on 16)

The method of claim 16, further comprising drying or freeze drying the incubated hydrated mixture to provide for a dried composition comprising glucosinolate breakdown products (GBPs).

### Claim 18 (depends on 16)

The method of claim 16, further comprising grinding, crushing, pulverizing, mincing, milling or otherwise breaking up the dried or freeze dried material to provide a dried or freeze dried material having increased surface area.

### Claim 19 (depends on 18)

The method of claim 18, further comprising extracting the dried or freeze dried material having increased surface area with a suitable solvent to provide for partitioning of one or more glucosinolate breakdown products (GBPs) from the extracted dried or freeze dried material into the solvent.

### Claim 20 (depends on 19)

The method of claim 19, further comprising segregating the extract-bearing solvent from the extracted dried or freeze dried material, and desolventizing the extract-bearing solvent to provide an extract composition comprising glucosinolate breakdown products (GBPs).

### Claim 21 (depends on 20)

The method of claim 20, further comprising desolventizing the extracted dried or freeze dried material to provide a re-extracted plant material depleted of oil, glucosinolates and glucosinolate breakdown products (GBPs).

### Claim 22 (depends on 16)

The method of claim 16, wherein the processed glucosinolate-containing plant material comprises a oilseed-derived seedmeal material from which the oil has been removed by the processing, and wherein the processing comprises at least one of solvent extraction and heat treatment.

### Claim 23 (depends on 16)

The method of claim 16, wherein the low-fat composition comprises a glucosinolate breakdown product (GBP) to fat (free fatty acid (FFA) plus triacylglycerol (TAG)) ratio, in terms of wt %, in the range of about 1:1 to about 1:3.

### Claim 24 (depends on 20)

The method of claim 20, wherein the extract composition comprises a glucosinolate breakdown product (GBP) to fat (free fatty acid (FFA) plus triacylglycerol (TAG)) ratio, in terms of wt %, in the range of about 1:1 to about 1:3.

### Claim 25 (depends on 16)

The method of claim 16, wherein the exogenous glucosinolate converting enzyme activity comprises at least one of a myrosinase activity and a nitrile-forming activity.

### Claim 26 (depends on 16)

The method of claim 16, wherein the exogenous glucosinolate converting enzyme activity comprises that of a heterologous plant relative to the processed glucosinolate-containing plant material.

### Claim 27 (depends on 16)

The method of claim 16, wherein providing the exogenous glucosinolate converting enzyme activity comprises providing a plant material having glucosinolate converting enzyme activity.

### Claim 28 (depends on 27)

The method of claim 27, wherein the plant material having glucosinolate converting enzyme activity comprises seed material of a seed oil plant.

### Claim 29 (depends on 28)

The method of claim 28, wherein the amount of plant material having glucosinolate converting enzyme activity is present in an amount less than 2 wt %, less than 5 wt %, or less than 10 wt %, relative to the amount of processed glucosinolate-containing plant material.

### Claim 30 (depends on 16)

The method of claim 16, wherein the glucosinolate breakdown products (GBPs) comprise at least one product selected from the group consisting of a glucosinolate-derived isothiocyante, a glucosinolate-derived nitrile and an acetamide derivative of a glucosinolate-derived nitrile.

### Claim 31 (depends on 30)

The method of claim 30, wherein incubating the hydrated mixture is in the presence of an enzymatic co-factor or agent that promotes formation of the glucosinolate-derived nitrile or acetamide derivative of a glucosinolate-derived nitrile, relative to formation of the glucosinolate-derived isothiocyante.

### Claim 32 (depends on 31)

The method of claim 31, wherein the enzymatic co-factor or agent comprises a metal ion.

### Claim 33 (depends on 32)

The method of claim 32, wherein the metal is at least one selected from the group consisting of Fe2+, Zn2+, Ca2+, Mg2+, CU2+, and Mn2+.

### Claim 34 (depends on 16)

The method claim 16, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from at least one plant selected from the group consisting of: Crambe (Crambe abysinnica); Black Mustard; Yellow Mustard (Sinapis alba); Oriental Mustard (Brassica juncea); Broccoli (Brassica oleracea italica); Rapeseed (Brassica napus); Meadowfoam (Limnanthes alba), Radish (Raphanus sativus); Wasabi (Wasabia japonica); Horseradish (Cochlearia Armoracia); Cauliflower; Garden cress (Lepidium sativum); Watercress (Nasturtium officinalis); and Papaya (Carica papaya).

### Claim 35 (depends on 34)

The method of claim 34, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from Meadowfoam (Limnanthes alba).

### Claim 36 (depends on 16)

The method of claim 16, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from the genus Brassicas.

### Claim 37

A method for providing a low-fat composition comprising a glucosinolate-containing plant material, comprising:
providing an amount of processed glucosinolate-containing plant material, the processed plant material being depleted of oil and glucosinolate converting enzyme activity by virtue of said processing;
providing an amount of exogenous glucosinolate converting enzyme activity comprising a thioglucosidase; and
mixing the processed glucosinolate-containing plant material with the amount of exogenous glucosinolate converting enzyme activity comprising the thioglucosidase to provide a low-fat composition comprising a processed glucosinolate-containing plant material.

### Claim 38 (depends on 37)

The method of claim 37, further comprising drying or freeze drying the low-fat composition to provide for a dried low-fat composition comprising glucosinolate breakdown products (GBPs).

### Claim 39 (depends on 37)

The method of claim 37, further comprising grinding, crushing, pulverizing, mincing, milling or otherwise breaking up the dried or freeze dried material to provide a dried or freeze dried low-fat material having increased surface area.

### Claim 40 (depends on 37)

The method of claim 37, further comprising pelletizing, compressing, or otherwise consolidating the low-fat composition comprising a glucosinolate-containing plant material.

### Claim 41 (depends on 37)

The method of claim 37, wherein the processed glucosinolate-containing plant material comprises a oilseed-derived seedmeal material from which the oil has been removed by the processing, and wherein the processing comprises at least one of solvent extraction and heat treatment.

### Claim 42 (depends on 37)

The method of claim 37, wherein the exogenous glucosinolate converting enzyme activity comprises at least one of a myrosinase activity and a nitrile-forming activity.

### Claim 43 (depends on 37)

The method of claim 37, wherein the exogenous glucosinolate converting enzyme activity comprises that of a heterologous plant relative to the processed glucosinolate-containing plant material.

### Claim 44 (depends on 37)

The method of claim 37, wherein providing the exogenous glucosinolate converting enzyme activity comprises providing a plant material having glucosinolate converting enzyme activity.

### Claim 45 (depends on 44)

The method of claim 44, wherein the plant material having glucosinolate converting enzyme activity comprises seed material of a seed oil plant.

### Claim 46 (depends on 45)

The method of claim 45, wherein amount of plant material having glucosinolate converting enzyme activity is present in an amount less than 2 wt %, less than 5 wt %, or less than 10 wt %, relative to the amount of processed glucosinolate-containing plant material.

### Claim 47 (depends on 37)

The method of claim 37, wherein the glucosinolate breakdown products (GBPs), comprise at least one product selected from the group consisting of a glucosinolate-derived isothiocyante, a glucosinolate-derived nitrile and an acetamide derivative of a glucosinolate-derived nitrile.

### Claim 48 (depends on 37)

The method of claim 37, further comprising providing an enzymatic co-factor or agent that promotes formation of the glucosinolate-derived nitrile or acetamide derivative of a glucosinolate-derived nitrile, relative to formation of the glucosinolate-derived isothiocyante, and mixing the enzymatic co-factor or agent with the processed glucosinolate-containing plant material and the glucosinolate converting enzyme activity.

### Claim 49 (depends on 48)

The method of claim 48, wherein the enzymatic co-factor or agent comprises a metal ion.

### Claim 50 (depends on 49)

The method of claim 49, wherein the metal is at least one selected from the group consisting of Fe2+, Zn2+, Ca2+, Mg2+, Cu2+, and Mn2+.

### Claim 51 (depends on 37)

The method of claim 37, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from at least one plant selected from the group consisting of: Crambe (Crambe abysinnica); Black Mustard; Yellow Mustard (Sinapis alba); Oriental Mustard (Brassica juncea); Broccoli (Brassica oleracea italica); Rapeseed (Brassica napus); Meadowfoam (Limnanthes alba), Radish (Raphanus sativus); Wasabi (Wasabia japonica); Horseradish (Cochlearia Armoracia); Cauliflower; Garden cress (Lepidium sativum); Watercress (Nasturtium officinalis); and Papaya (Carica papaya).

### Claim 52 (depends on 51)

The method of claim 51, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from Meadowfoam (Limnanthes alba).

### Claim 53 (depends on 37)

The method of claim 37, wherein at least one of the processed glucosinolate-containing plant material and the exogenous glucosinolate converting enzyme activity comprises material from the genus Brassicas.