WO1996020595B1 - Modulating toxic metabolite levels in consumable products - Google Patents
Modulating toxic metabolite levels in consumable productsInfo
- Publication number
- WO1996020595B1 WO1996020595B1 PCT/US1995/017049 US9517049W WO9620595B1 WO 1996020595 B1 WO1996020595 B1 WO 1996020595B1 US 9517049 W US9517049 W US 9517049W WO 9620595 B1 WO9620595 B1 WO 9620595B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- organic substituent
- mycotoxin
- producing
- cho
- Prior art date
Links
- 239000002207 metabolite Substances 0.000 title 1
- 231100000331 toxic Toxicity 0.000 title 1
- 230000002588 toxic effect Effects 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 16
- 125000001424 substituent group Chemical group 0.000 claims abstract 16
- 238000000034 method Methods 0.000 claims abstract 12
- 239000000203 mixture Substances 0.000 claims abstract 12
- 231100000678 Mycotoxin Toxicity 0.000 claims abstract 11
- 239000002636 mycotoxin Substances 0.000 claims abstract 11
- 241000233866 Fungi Species 0.000 claims abstract 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 4
- 244000005700 microbiome Species 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims 6
- 230000009885 systemic effect Effects 0.000 claims 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims 2
- 208000035240 Disease Resistance Diseases 0.000 claims 2
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 claims 2
- 229940117916 cinnamic aldehyde Drugs 0.000 claims 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims 2
- DKZBBWMURDFHNE-NSCUHMNNSA-N coniferyl aldehyde Chemical compound COC1=CC(\C=C\C=O)=CC=C1O DKZBBWMURDFHNE-NSCUHMNNSA-N 0.000 claims 2
- 230000001939 inductive effect Effects 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 230000001988 toxicity Effects 0.000 claims 2
- 231100000419 toxicity Toxicity 0.000 claims 2
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 claims 2
- -1 R2 represents -H Chemical group 0.000 claims 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 claims 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 claims 1
- 230000000443 biocontrol Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- 230000017066 negative regulation of growth Effects 0.000 claims 1
- 238000012794 pre-harvesting Methods 0.000 claims 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims 1
- 229930182490 saponin Natural products 0.000 claims 1
- 150000007949 saponins Chemical group 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 abstract 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 239000003053 toxin Substances 0.000 abstract 2
- 241000196324 Embryophyta Species 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 abstract 1
- 244000061176 Nicotiana tabacum Species 0.000 abstract 1
- 240000008042 Zea mays Species 0.000 abstract 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract 1
- 238000010171 animal model Methods 0.000 abstract 1
- 239000004464 cereal grain Substances 0.000 abstract 1
- 235000020971 citrus fruits Nutrition 0.000 abstract 1
- 235000005822 corn Nutrition 0.000 abstract 1
- 235000013399 edible fruits Nutrition 0.000 abstract 1
- 235000011868 grain product Nutrition 0.000 abstract 1
- 238000003306 harvesting Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 238000012956 testing procedure Methods 0.000 abstract 1
- 231100000765 toxin Toxicity 0.000 abstract 1
Abstract
Methods and compositions are provided for controlling the level of toxic metabolites in plants before, during and/or after harvest and/or processing. The invention finds use for reducing the health risk associated with the consumption products such as tobacco, cereal grain feeds, processed grain products such as corn syrup, citrus fruits, underground vegetables, fruit vegetables, flower, leafy and stem vegetables, and cut flowers, and for improving laboratory animal testing procedures by controlling the level of mycotoxins associated with the materials that colonize toxin producing microorganisms. Compositions for controlling mycotoxin-producing fungi comprise cinnemaic aldehyde, conferyl aldehyde or derivatives thereof having formula (I) wherein R1 represents -CHO, R2 represents -OH or an organic substituent comprising 1-10 carbon atoms, R3 represents -OCH3 or an organic substituent comprising 1-10 carbon atoms and R4 represents -H or an organic substituent comprising 1-10 carbon atoms.
Claims
1. A method for biocontrol of mycotoxin-producing microorganisms on a harvested plant part, said method comprising: providing a plant part with an effective microbial growth modulating amount of a formulation comprising at least one of the compounds of formula
2. A method according to claim 1, wherein R, represents -CHO, R3 represents ■ OH or an organic substituent comprising 1-10 carbon atoms, R2 represents -O-CH3 or an organic substituent comprising 1-10 carbon atoms and R, represents -H or an organic substituent comprising 1-10 carbon atoms.
3. A method according to claim 1 , wherein at least one compound is cinnamic aldehyde, coniferyl aldehyde or α-hexyl cinnamic aldehyde.
4. A method according to any of claim 1-3, wherein said growth modulating amount provides a mean disease resistance of about 70% or higher.
5. A method according to any of claims 1-4, wherein said providing is preharvesting of said plant part.
6. A method according to any one of claims 1-5, wherein inhibition of growth of said mycotoxin producing microorganisms is for a period greater than one month.
7. A composition comprising a growth modulating amount of one or more compounds of the formula
2
43 wherein R, represent -CHO, R3 represents -H, -OH or an organic substituent comprising 1- 10 carbon atoms, R2 represents -H, -OCH3 or an organic substituent comprising 1-10 carbon atoms and R, represents -H or an organic substituent comprising 1-10 carbon atoms, in an anti-oxidant-free agriculturally compatible carrier, wherein said composition provides a mean disease resistant of about 70% or higher against a myctoxin-producing fungi which colonizes one or more plant surface when applied to said plant surface.
8. A composition according to claim 7, wherein said growth modulating amount produces a phy toxicity rating of 1 or less.
9. A composition according to claim 7 or 8, wherein one or more compounds are cinnamic aldehyde or coniferyl aldehyde.
10. Use of a composition according to claim 7, 8 or 9 in providing a mean disease resistance of about 70% or higher against a mycotoxin-producing fungus.
11. Use according to claim 10, producing a phy toxicity rating or 1 or less.
12. Harvested plants or plant parts substantially free of mycotoxin-producing fungi obtained according to the method of any one of claims 1-6.
13. A method for inducing resistance to mycotoxin-producing fungi, said method comprising: providing said plants with a sufficient amount of a compound of the formula
wherein R, represents -CHO, R3 represents -OH or an organic substituent comprising 1-10 carbon atoms, R2 represents -OCH3 or an orgamc substituent comprising 1-10 carbon atoms and R4 represents -H or an organic substituent comprising 1-10 carbon atoms to induce systemic resistance to said mycotoxin-producing fungi.
44
14. Composition for use in a method according to claim 13 comprising a sufficient amount of a compound according to the formula
wherein R, represents -CHO, R3 represents -OH or an organic substituent comprising 1-10 carbon atoms, R2 represents -OCH3 or an organic substituent comprising 1-10 carbon atoms and R, represents -H or an organic substituent comprising 1-10 carbon atoms to induce systemic resistance to mycotoxin-producing fungi and a suitable carrier.
15. The composition according to claim 14, wherein said suitable carrier comprises a surfactant.
16. The composition according to claim 15, wherein said surfactant is a saponin.
17. Use of a composition according to any one of claims 14-16 in inducing systemic resistance in plants against mycotoxin-producing fungi.
45
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69526251T DE69526251T2 (en) | 1994-12-30 | 1995-12-29 | REGULATING THE CONTENT OF TOXIC METABOLITES IN FOOD |
| AT95944684T ATE215307T1 (en) | 1994-12-30 | 1995-12-29 | REGULATION OF THE CONTENT OF TOXIC METABOLITES IN FOODS |
| EP95944684A EP0800345B1 (en) | 1994-12-30 | 1995-12-29 | Toxic metabolite modulation in consumable products |
| BR9510180A BR9510180A (en) | 1994-12-30 | 1995-12-29 | Process to control the growth of fungi produced by mycotoxins in a plant part composition use of the same plants or parts of plants substantially free of fungi using microtoxin and process to induce resins of fungi producing a mycotoxin |
| JP8521176A JPH11501295A (en) | 1994-12-30 | 1995-12-29 | Regulation of toxic metabolite levels in consumable products |
| NZ301911A NZ301911A (en) | 1994-12-30 | 1995-12-29 | Biocontrol of mycotoxin-producing micro-organisms |
| AU47442/96A AU4744296A (en) | 1994-12-30 | 1995-12-29 | Modulating toxic metabolite levels in consumable products |
| MXPA/A/1997/004964A MXPA97004964A (en) | 1994-12-30 | 1997-06-30 | Modulation of the levels of toxic metabolites in consumib products |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36708294A | 1994-12-30 | 1994-12-30 | |
| US48503595A | 1995-06-07 | 1995-06-07 | |
| US08/485,035 | 1995-06-07 | ||
| US08/367,082 | 1995-06-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996020595A1 WO1996020595A1 (en) | 1996-07-11 |
| WO1996020595B1 true WO1996020595B1 (en) | 1996-09-26 |
Family
ID=33302708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1995/017049 WO1996020595A1 (en) | 1994-12-30 | 1995-12-29 | Modulating toxic metabolite levels in consumable products |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0800345B1 (en) |
| JP (1) | JPH11501295A (en) |
| AT (1) | ATE215307T1 (en) |
| AU (1) | AU4744296A (en) |
| BR (1) | BR9510180A (en) |
| CA (1) | CA2208753A1 (en) |
| DE (1) | DE69526251T2 (en) |
| NZ (1) | NZ301911A (en) |
| PL (1) | PL321179A1 (en) |
| WO (1) | WO1996020595A1 (en) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6410718B1 (en) | 1996-09-11 | 2002-06-25 | Genesis Research & Development Corporation Ltd. | Materials and methods for the modification of plant lignin content |
| US7087426B2 (en) | 1996-09-11 | 2006-08-08 | Agrigenesis Biosciences Ltd. | Materials and methods for the modification of plant lignin content |
| US5850020A (en) * | 1996-09-11 | 1998-12-15 | Genesis Research & Development Corporation, Ltd. | Materials and method for the modification of plant lignin content |
| US6204434B1 (en) | 1996-09-11 | 2001-03-20 | Genesis Research & Development Corporation Limited | Materials and methods for the modification of plant lignin content |
| US5798255A (en) * | 1996-11-22 | 1998-08-25 | Pioneer Hi-Bred International, Inc. | Beauvericin detoxification compositions and methods |
| US5846812A (en) * | 1996-11-22 | 1998-12-08 | Pioneer Hi-Bred International, Inc. | Zearalenone detoxification compositions and methods |
| BR9713389A (en) * | 1996-11-22 | 2002-05-14 | Pioneer Hi Bred Int | Moniliformin detoxification methods and compositions |
| WO2001028367A1 (en) * | 1997-04-21 | 2001-04-26 | Kerry Scott Lane | Method and system for assay and removal of harmful toxins during processing of tobacco products |
| CA2295989A1 (en) * | 1997-06-20 | 1998-12-30 | Applied Phytologics, Inc. | Pathogen-resistant monocot plants and method |
| US6060646A (en) * | 1997-08-12 | 2000-05-09 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture | Tolerance of trichothecene mycotoxins in plants and animals through the modification of the peptidyl transferase gene |
| US6855872B2 (en) | 1997-08-12 | 2005-02-15 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture And Agri-Food | Tolerance of trichothecene mycotoxins in plants through the modification of the ribosomal protein L3 gene |
| WO1999010514A1 (en) * | 1997-08-26 | 1999-03-04 | North Carolina State University | Fumonosin resistance |
| JP2002520058A (en) * | 1998-07-15 | 2002-07-09 | パイオニア ハイ−ブレッド インターナショナル， インコーポレイテッド | Aminopolyolamine oxidase polynucleotides and related polypeptides and methods of use |
| US6943279B1 (en) | 1999-07-12 | 2005-09-13 | Pioneer Hi-Bred International, Inc. | Amino polyol amine oxidase polynucleotides and related polypeptides and methods of use |
| US6538177B1 (en) * | 1998-07-15 | 2003-03-25 | Pioneer Hi-Bred International, Inc. | Compositions and methods for fumonisin detoxification |
| WO2000004160A1 (en) | 1998-07-15 | 2000-01-27 | Pioneer Hi-Bred International, Inc. | Amino polyol amine oxidase polynucleotides and related polypeptides and methods of use |
| NZ510940A (en) | 1998-10-09 | 2004-01-30 | Genesis Res & Dev Corp Ltd | Materials and methods for the modification of plant lignin content |
| US7129393B1 (en) | 1999-02-22 | 2006-10-31 | Yissum Research Development Company Of The Hebrew University | Transgenic plants and method for transforming carnations |
| AU2687000A (en) * | 1999-02-22 | 2000-09-14 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Transgenic plants and method for transforming carnations |
| US6074838A (en) * | 1999-05-20 | 2000-06-13 | Pioneer Hi-Bred International, Inc. | Zearalenone detoxification compositions and methods |
| US6388171B1 (en) | 1999-07-12 | 2002-05-14 | Pioneer Hi-Bred International, Inc. | Compositions and methods for fumonisin detoxification |
| EP1196601A1 (en) * | 1999-07-14 | 2002-04-17 | Pioneer Hi-Bred International Inc. | Compositions and methods for fumonisin detoxification |
| ES2163999B1 (en) * | 1999-11-11 | 2003-03-01 | Inabonos Sa | COMPOSITION OF NATURAL ORIGIN TO CONTROL THE POST-HARVEST PATHOLOGY OF FRUIT AND VEGETABLES AND APPLICATION METHOD. |
| US6812380B2 (en) | 2001-03-27 | 2004-11-02 | Pioneer Hi-Bred International, Inc. | Compositions and methods of zearalenone detoxification |
| CA2596049A1 (en) * | 2005-01-26 | 2006-08-03 | Emma Kvitnitsky | Compositions and methods for protection of harvested fruits from decay |
| CA2951435A1 (en) | 2014-06-06 | 2015-12-10 | Board Of Trustees Of Michigan State University | Compounds for inhibition of fungal toxin production |
| KR101797713B1 (en) | 2015-05-14 | 2017-11-16 | 한국과학기술원 | A method for production of cinnamaldehyde |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR8206283A (en) * | 1982-07-06 | 1984-04-17 | Kiyoshi Saotome | CROP PROTECTION PROCESS |
| JPS6165802A (en) * | 1984-09-10 | 1986-04-04 | Maruzen Kasei Kk | Preservative |
| JP2621114B2 (en) * | 1987-04-13 | 1997-06-18 | 清 五月女 | How to protect crops with non-toxic compositions |
| US5149715A (en) * | 1989-02-09 | 1992-09-22 | Monterey Mushroom, Inc. | Control of fungal diseases in the production of mushrooms |
| JPH05139924A (en) * | 1991-11-25 | 1993-06-08 | Itouen:Kk | Plant disease control agent containing natural ingredients as active ingredients |
-
1995
- 1995-12-29 NZ NZ301911A patent/NZ301911A/en not_active IP Right Cessation
- 1995-12-29 DE DE69526251T patent/DE69526251T2/en not_active Expired - Lifetime
- 1995-12-29 AU AU47442/96A patent/AU4744296A/en not_active Abandoned
- 1995-12-29 WO PCT/US1995/017049 patent/WO1996020595A1/en active IP Right Grant
- 1995-12-29 BR BR9510180A patent/BR9510180A/en not_active Application Discontinuation
- 1995-12-29 EP EP95944684A patent/EP0800345B1/en not_active Expired - Lifetime
- 1995-12-29 PL PL95321179A patent/PL321179A1/en unknown
- 1995-12-29 AT AT95944684T patent/ATE215307T1/en not_active IP Right Cessation
- 1995-12-29 CA CA002208753A patent/CA2208753A1/en not_active Abandoned
- 1995-12-29 JP JP8521176A patent/JPH11501295A/en active Pending
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