IP Library Granted Patent US 8,784,856
Granted Patent B2
US 8,784,856 · App. 12/664,984 · Granted Jul 22, 2014

Meadowfoam-based bioherbicide products

Inventors: Jan F. Stevens (Corvallis, OR); Stephen Machado (Pendelton, OR); Ralph Reed (Philomath, OR); Michael S. Martinez (Salem, OR)
Assignee: The State of Oregon Acting by and Through the State Boad of Higher Education on Behalf of Oregon State University
A01N25/32A01N25/28A01N65/00
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Quick Facts
Patent No.
US 8,784,856
App. No.
12/664,984
Granted
Jul 22, 2014
Kind
B2
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 (66)

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.

2. 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.

3. 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.

4. 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.

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

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

7. 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.

8. 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.

9. 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.

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

11. The method of claim 10 , wherein the metal is at least one selected from the group consisting of Fe 2+ , Zn 2+ , Ca 2+ , Mg 2+ , Cu 2+ , and Mn 2+ .

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

13. 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 ).

14. 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 ).

15. 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.

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.

17. 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).

18. 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.

19. 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.

20. 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).

21. 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).

22. 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.

23. 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.

24. 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.

25. 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.

26. 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.

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

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

29. 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.

30. 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.

31. 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.

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

33. The method of claim 32 , wherein the metal is at least one selected from the group consisting of Fe 2+ , Zn 2+ , Ca 2+ , Mg 2+ , CU 2+ , and Mn 2+ .

34. 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 ).

35. 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 ).

36. 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.

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.

38. 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).

39. 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.

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

41. 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.

42. 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.

43. 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.

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

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

46. 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.

47. 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.

48. 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.

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

50. The method of claim 49 , wherein the metal is at least one selected from the group consisting of Fe 2+ , Zn 2+ , Ca 2+ , Mg 2+ , Cu 2+ , and Mn 2+ .

51. 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 ).

52. 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 ).

53. 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.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE 11/664,984 PREVIOUSLY RECORDED ON REEL 033106 FRAME 0003. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT OF ASSIGNOR'S INTEREST. Recorded Jun 26, 2014
From: STEVENS, JAN F.; MACHADO, STEPHEN; REED, RALPH; MARTINEZ, MICHAEL S.
To: THE STATE OF OREGON ACTING BY AND THROUGH THE STATE BOARD OF HIGHER EDUCATION ON BEHALF OF OREGON STATE UNIVERSITY
Reel/Frame 033244/0530 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2014
From: STEVENS, JAN F.; MACHADO, STEPHEN; REED, RALPH; MARTINEZ, MICHAEL S.
To: THE STATE OF OREGON ACTING BY AND THROUGH THE STATE BOARD OF HIGHER EDUCATION ON BEHALF OF OREGON STATE UNIVERSITY
Reel/Frame 033106/0003 →
Continuity (2)
Provisional Application 60961323 · Jul 19, 2007
Related Publication 20100317518A1 · Dec 16, 2010