WO1999023889A2 - Use of lysophosphatidylethanolamine (18:1) and lysophosphatidylinositol to retard senescene and to enhance fruit ripening - Google Patents
Use of lysophosphatidylethanolamine (18:1) and lysophosphatidylinositol to retard senescene and to enhance fruit ripening Download PDFInfo
- Publication number
- WO1999023889A2 WO1999023889A2 PCT/US1998/023714 US9823714W WO9923889A2 WO 1999023889 A2 WO1999023889 A2 WO 1999023889A2 US 9823714 W US9823714 W US 9823714W WO 9923889 A2 WO9923889 A2 WO 9923889A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- lpe
- fruit
- pld
- lpi
- lysophospholipid
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3526—Organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
- A23B7/154—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/16—Coating with a protective layer; Compositions or apparatus therefor
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3553—Organic compounds containing phosphorus
Definitions
- composition 1000 mg per 1 liter of the composition, preferably from about 1 to about 500 mg per 1 liter of the composition, more preferably from about 5 to about 250 mg per 1 liter of the composition and even more preferably from about 5 to about 100 mg per 1 liter of the composition.
- the composition can be applied to the fruit or plant tissues as a spray or simply in liquid form.
- the composition can also contain one or more activating compounds.
- activating compounds refers to agents that enhance wettability uptake and effectiveness of the active ingredient, which is the lysophospholipid.
- activating compounds include ethanol, tergitol and sylgard 309 (available from Dow Corning Co., Midland, MI).
- the activating compounds are present in the .amount of from about 0.05 to about 2.0% v/v of the composition.
- the preferred lysophospholipid, LPE (18:1) is a species of LPE having an 18 carbon fatty acid containing a single double bond.
- Castor bean plants were grow ontaining a mixture of vermiculite and parlayed (1:1, at 22°C with Hoagland nutrient solution under cool-wh --rescent lights (150 ⁇ mol min 1 m 2 ) with a 14-h photoperiod (10). Cabbage was obtained from fresh market.
- the activity of partially purified cabbage PLD was assayed by measuring the phosphorus content contained in phosphatidylethanol (hereinafter referred to as "PEOH”) and phosphatidic acid (hereinafter referred to as "PA”) released from the substrate phosphatidylcholine (hereinafter referred to as "PC”)
- PEOH phosphatidylethanol
- PA phosphatidic acid
- PC substrate phosphatidylcholine
- LPEegg (extracted from egg yolk) had been found to delay fruit senescence as indicated by lowered rates of ethylene production when compared to the control (3). Since the inventors found that the inhibitory effectiveness of LPE on PLD was dependent on the length and unsaturation of acyl chain of LPE (Fig. 1), the effects of LPE with different acyl chains on fruit senescence were tested. Cranberry fruits were treated with LPE with 14:0, 16:0, 18:0 and 18:1 chain lengths, and ethylene production by these fruits was monitored. The inhibition of ethylene production increased with acyl chain length and the unsaturation of LPE (Table 2). LPE (18: 1) resulted in the most dramatic decrease (40%) in ethylene production 2 days after treatment.
- LPE Lysophosphatidylcholine
- LPG lysophosphatidylglycerol
- LPS lysophosphatidylserine
- EXAMPLE 2 Retarding Senescence and Enhancing the Shelf-Life of Flowers Flowering spikes of snapdragon (Antirrhinum majus L. cv.
- LPI and LPE (18:1) Flowers treated with LPI and LPE (18:1) remained marketable up to 13 days while water-treated flowers and LPEegg-treated flowers remained marketable for 4 days and 7 days, respectively.
- Leaf water content of LPE (18: l)-and LPI-treated spikes was higher than that of LPEegg and water-treated spikes at 18 days after treatment. This data is consistent with the improved shelf-life of flowers treated with LPE (18: 1) and LPI. This data support that LPE (18: 1) and LPI are superior to LPEegg.
- Ethephon also known as Ethrel, (Ethrel is a trademark of Rhone- Poulenc Ag. Co. (Research Triangle Park, NC)) is an aqueous formulation that decomposes to ethylene and is used widely to maximize the yield of ripe tomato fruits in once-over harvesting operations.
- NC Search Triangle Park
- LPE (18: 1) is superior to LPEegg and other lysophospholipids in protecting leaves from ethephon-induced leaf senescence.
- Tomato plants cv. H9144 were grown in a greenhouse for two and a half months to serve as sources of leaf samples. Plant were sprayed to runoff with ethephon at 1000 mg/L or with ethephon plus lysophospholipid mixtures as shown below in Table 6. Lysophospholipid solutions at 50 mg/L were prepared in 1 % (v/v) ethanol and mixed with ethephon (1000 mg/L). Control plants were sprayed with ethephon alone in 1% (v/v) ethanol. Senescence of treated leaves was quantified 10 to 14 days after treatment by measuring chlorophyll and protein content. Ethephon-sprayed leaf tissue showed dramatic loss in chlorophyll and protein content as shown in Table 6 below.
- LPEegg enhanced fruit ripening significantly compared to the control as previously disclosed in U.S. Patents 5,126,155 and 5,110,341 (see Table 7). However, LPI and LPE (18:1) were found to be more effective than LPEegg. LPI and LPE (18:1) also enhanced fruit stability by prolonging shelf life of post harvest fruits compared to control and LPEegg (see Table 7).
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Enzymes And Modification Thereof (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69814139T DE69814139T2 (en) | 1997-11-10 | 1998-11-09 | USE OF LYSOPHOSPHATIDYLETHANOLAMINE (18: 1) AND LYSOPHOSPHATIDYLINOSITOL TO DELAY SENESCENCE AND PROMOTE FRUIT MATURATION |
IL13604898A IL136048A0 (en) | 1997-11-10 | 1998-11-09 | Method for enhancing fruit ripening and stability using a composition containing a lysophospholipid |
US09/254,039 US6426105B1 (en) | 1997-11-10 | 1998-11-09 | Use of lysophosphatidylethanolamine (18.1) and lysophosphatidylinositol to retard senescence and to enhance fruit ripening |
CA002309665A CA2309665C (en) | 1997-11-10 | 1998-11-09 | Use of lysophosphatidylethanolamine (18:1) and lysophosphatidylinositol to retard senescence and to enhance fruit ripening |
BRPI9814027-2A BR9814027B1 (en) | 1997-11-10 | 1998-11-09 | use of lysophosphatidyl ethanolamine (18: 1) and lysophosphatidylinositol to retard senescence and to intensify fruit ripening. |
JP2000520004A JP2001522594A (en) | 1997-11-10 | 1998-11-09 | Use of lysophosphatidylethanolamine (18: 1) and lysophosphatidylinositol for delaying aging and improving fruit ripening |
EP98956657A EP1030563B1 (en) | 1997-11-10 | 1998-11-09 | Use of lysophosphatidylethanolamine (18:1) and lysophosphatidylinositol to retard senescence and to enhance fruit ripening |
AT98956657T ATE238678T1 (en) | 1997-11-10 | 1998-11-09 | USE OF LYSOPHOSPHATIDYLETHANOLAMINE (18:1) AND LYSOPHOSPHATIDYLINOSITOL TO DELAY SENSENCE AND PROMOTE FRUIT RIGATION |
KR1020007005090A KR100808416B1 (en) | 1997-11-10 | 1998-11-09 | Use of lysophosphatidylethanolamine 18:1 and lysophosphatidylinositol to retard senescene and to enhance fruit ripening |
AU13128/99A AU749333B2 (en) | 1997-11-10 | 1998-11-09 | Use of lysophosphatidylethanolamine (18:1) and lysophosphatidylinositol to retard senescene and to enhance fruit ripening |
NZ504432A NZ504432A (en) | 1997-11-10 | 1998-11-09 | Use of lysophosphatidylethanolamine (18:1) and lysophosphatidylinositol to retard senescene and to enhance fruit ripening |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6478497P | 1997-11-10 | 1997-11-10 | |
US60/064,784 | 1997-11-10 |
Publications (3)
Publication Number | Publication Date |
---|---|
WO1999023889A2 true WO1999023889A2 (en) | 1999-05-20 |
WO1999023889A3 WO1999023889A3 (en) | 1999-08-19 |
WO1999023889A9 WO1999023889A9 (en) | 2001-05-31 |
Family
ID=22058254
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/023714 WO1999023889A2 (en) | 1997-11-10 | 1998-11-09 | Use of lysophosphatidylethanolamine (18:1) and lysophosphatidylinositol to retard senescene and to enhance fruit ripening |
Country Status (15)
Country | Link |
---|---|
US (1) | US6426105B1 (en) |
EP (1) | EP1030563B1 (en) |
JP (1) | JP2001522594A (en) |
KR (1) | KR100808416B1 (en) |
CN (1) | CN1297329A (en) |
AT (1) | ATE238678T1 (en) |
AU (1) | AU749333B2 (en) |
BR (1) | BR9814027B1 (en) |
CA (1) | CA2309665C (en) |
DE (1) | DE69814139T2 (en) |
ES (1) | ES2198078T3 (en) |
IL (1) | IL136048A0 (en) |
NZ (1) | NZ504432A (en) |
TR (1) | TR200002113T2 (en) |
WO (1) | WO1999023889A2 (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001030143A2 (en) * | 1999-10-28 | 2001-05-03 | University Of North Texas | Methods for extending the freshness of cut flowers, ornamental trees, and plant cuttings |
KR20010062866A (en) * | 1999-12-17 | 2001-07-09 | 박관화 | A method for blanching of vegetables using phospholipase or galactolipase as an indicator enzyme |
WO2001064832A2 (en) * | 2000-02-28 | 2001-09-07 | Miklos Ghyczy | Composition for use on plants |
WO2001072130A2 (en) * | 2000-03-29 | 2001-10-04 | Wisconsin Alumni Research Foundation | Methods for enhancing plant health and protecting plants from stress |
WO2004014135A2 (en) * | 2002-08-09 | 2004-02-19 | Nutra-Park, Inc. | Use of certain n-acylethanolamines to achieve ethylene- and cytokinin-like effects in plants and fungi |
FR2857564A1 (en) * | 2003-07-15 | 2005-01-21 | Xeda International | Reducing phytotoxic effects, especially skin damage, caused by physical and chemical treatment of fruit and vegetables, by application of lecithins and their derivatives |
US7199082B1 (en) | 1999-10-28 | 2007-04-03 | University Of North Texas | Methods for extending the freshness of cut flowers, ornamental trees, and plant cuttings |
WO2019058211A1 (en) * | 2017-09-22 | 2019-03-28 | Decco Worldwide Post-Harvest Holdings B.V. | A method for treating and controlling post-harvest physiological disorders in fruit via edible coatings |
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KR100472297B1 (en) * | 2001-09-27 | 2005-03-07 | 주식회사 두산 | Lysophospholipids Composition with Water Solubility |
KR20050084521A (en) * | 2003-01-03 | 2005-08-26 | 뉴트라-박, 인코포레이티드. | Method for treating plants and plant parts |
US20050221987A1 (en) * | 2004-01-27 | 2005-10-06 | Keith Rowley | Use of certain phospholipids to deliver hormonal effects to plants |
US20060062865A1 (en) * | 2004-09-17 | 2006-03-23 | Nebojsa Ilic | Tyrosinase inhibitor and method for preparation |
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CN102634504B (en) | 2006-01-30 | 2015-05-13 | 佐治亚州立大学研究基金会 | Induction and stabilization of enzymatic activity in microorganisms |
WO2008089140A1 (en) * | 2007-01-17 | 2008-07-24 | Dow Agrosciences Llc | Delivery of ethylene blocking and/or promoting agents |
US7943549B2 (en) * | 2007-04-02 | 2011-05-17 | Georgia State University Research Foundation, Inc. | Biological-based catalyst to delay plant development processes |
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MX361278B (en) | 2013-03-14 | 2018-12-03 | Univ Georgia State Res Found | Inhibiting or reducing fungal growth. |
CA2903501A1 (en) | 2013-03-14 | 2014-10-02 | Georgia State University Research Foundation, Inc. | Preventing or delaying chill injury response in plants |
KR101661706B1 (en) | 2014-06-24 | 2016-10-04 | 한국생명공학연구원 | Method for producing lysophosphatidylethanolamine 18:1 from microorganisms |
CN106614741B (en) * | 2016-09-30 | 2019-06-25 | 鲁东大学 | A kind of promotion grape colours sweetened composition |
KR102343292B1 (en) * | 2019-10-21 | 2021-12-27 | 한국생명공학연구원 | Composition comprising lyso-phosphatidylethanolamine 18:2 to alleviate symptoms of plant virus diseases and uses thereof |
CN110840901A (en) * | 2019-12-12 | 2020-02-28 | 南京大学 | Application of lysophosphatidylethanolamine 18:1 in preparation of medicines for relieving and treating inflammatory bowel diseases |
US11793220B2 (en) | 2021-01-21 | 2023-10-24 | Jp Laboratories, Inc. | Materials and methods for extending shelf-life of foods |
WO2023077372A1 (en) * | 2021-11-04 | 2023-05-11 | 珠海市润农科技有限公司 | Application of higher aliphatic alcohol in inhibiting aging of solanaceae plants and increasing shelf life |
Citations (3)
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US5110341A (en) * | 1990-04-18 | 1992-05-05 | Wisconsin Alumni Research Foundation | Plant and fruit treatment with lysophosphatidylethanolamine |
US5126155A (en) * | 1990-04-18 | 1992-06-30 | Wisconsin Alumni Research Foundation | Plant and fruit treatment with lysophosphatidylethanolamine |
US5521223A (en) * | 1991-05-31 | 1996-05-28 | The Procter & Gamble Company | Methods of using lysophosphatidic acids for regulating skin wrinkles |
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-
1998
- 1998-11-09 BR BRPI9814027-2A patent/BR9814027B1/en not_active IP Right Cessation
- 1998-11-09 WO PCT/US1998/023714 patent/WO1999023889A2/en not_active Application Discontinuation
- 1998-11-09 EP EP98956657A patent/EP1030563B1/en not_active Expired - Lifetime
- 1998-11-09 TR TR2000/02113T patent/TR200002113T2/en unknown
- 1998-11-09 KR KR1020007005090A patent/KR100808416B1/en not_active IP Right Cessation
- 1998-11-09 IL IL13604898A patent/IL136048A0/en unknown
- 1998-11-09 ES ES98956657T patent/ES2198078T3/en not_active Expired - Lifetime
- 1998-11-09 AU AU13128/99A patent/AU749333B2/en not_active Ceased
- 1998-11-09 US US09/254,039 patent/US6426105B1/en not_active Expired - Lifetime
- 1998-11-09 CN CN98812021A patent/CN1297329A/en active Pending
- 1998-11-09 AT AT98956657T patent/ATE238678T1/en not_active IP Right Cessation
- 1998-11-09 JP JP2000520004A patent/JP2001522594A/en not_active Withdrawn
- 1998-11-09 DE DE69814139T patent/DE69814139T2/en not_active Expired - Lifetime
- 1998-11-09 CA CA002309665A patent/CA2309665C/en not_active Expired - Fee Related
- 1998-11-09 NZ NZ504432A patent/NZ504432A/en not_active IP Right Cessation
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US5110341A (en) * | 1990-04-18 | 1992-05-05 | Wisconsin Alumni Research Foundation | Plant and fruit treatment with lysophosphatidylethanolamine |
US5126155A (en) * | 1990-04-18 | 1992-06-30 | Wisconsin Alumni Research Foundation | Plant and fruit treatment with lysophosphatidylethanolamine |
US5521223A (en) * | 1991-05-31 | 1996-05-28 | The Procter & Gamble Company | Methods of using lysophosphatidic acids for regulating skin wrinkles |
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Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001030143A3 (en) * | 1999-10-28 | 2002-10-03 | Univ North Texas | Methods for extending the freshness of cut flowers, ornamental trees, and plant cuttings |
WO2001030143A2 (en) * | 1999-10-28 | 2001-05-03 | University Of North Texas | Methods for extending the freshness of cut flowers, ornamental trees, and plant cuttings |
US7199082B1 (en) | 1999-10-28 | 2007-04-03 | University Of North Texas | Methods for extending the freshness of cut flowers, ornamental trees, and plant cuttings |
KR20010062866A (en) * | 1999-12-17 | 2001-07-09 | 박관화 | A method for blanching of vegetables using phospholipase or galactolipase as an indicator enzyme |
WO2001064832A2 (en) * | 2000-02-28 | 2001-09-07 | Miklos Ghyczy | Composition for use on plants |
WO2001064832A3 (en) * | 2000-02-28 | 2002-05-23 | Miklos Ghyczy | Composition for use on plants |
WO2001072130A2 (en) * | 2000-03-29 | 2001-10-04 | Wisconsin Alumni Research Foundation | Methods for enhancing plant health and protecting plants from stress |
US6559099B1 (en) | 2000-03-29 | 2003-05-06 | Wisconsin Alumni Research Foundation | Methods for enhancing plant health, protecting plants from biotic and abiotic stress related injuries and enhancing the recovery of plants injured as a result of such stresses |
US7101828B2 (en) | 2000-03-29 | 2006-09-05 | Wisconsin Alumni Research Foundation | Methods for enhancing plant health, protecting plants from biotic and abiotic stress related injuries and enhancing the recovery of plants injured as a result of such stresses |
WO2001072130A3 (en) * | 2000-03-29 | 2002-03-28 | Wisconsin Alumni Res Found | Methods for enhancing plant health and protecting plants from stress |
WO2004014135A2 (en) * | 2002-08-09 | 2004-02-19 | Nutra-Park, Inc. | Use of certain n-acylethanolamines to achieve ethylene- and cytokinin-like effects in plants and fungi |
WO2004014135A3 (en) * | 2002-08-09 | 2004-07-08 | Nutra Park Inc | Use of certain n-acylethanolamines to achieve ethylene- and cytokinin-like effects in plants and fungi |
US7205261B2 (en) | 2002-08-09 | 2007-04-17 | Nutra-Park, Inc. | Use of certain N-acylethanolamines to achieve ethylene- and cytokinin-like effects in plants and fungi |
FR2857564A1 (en) * | 2003-07-15 | 2005-01-21 | Xeda International | Reducing phytotoxic effects, especially skin damage, caused by physical and chemical treatment of fruit and vegetables, by application of lecithins and their derivatives |
WO2019058211A1 (en) * | 2017-09-22 | 2019-03-28 | Decco Worldwide Post-Harvest Holdings B.V. | A method for treating and controlling post-harvest physiological disorders in fruit via edible coatings |
Also Published As
Publication number | Publication date |
---|---|
DE69814139T2 (en) | 2004-03-18 |
AU749333B2 (en) | 2002-06-27 |
AU1312899A (en) | 1999-05-31 |
NZ504432A (en) | 2002-10-25 |
ES2198078T3 (en) | 2004-01-16 |
KR20010031980A (en) | 2001-04-16 |
CA2309665C (en) | 2007-08-21 |
EP1030563B1 (en) | 2003-05-02 |
BR9814027A (en) | 2001-10-16 |
US6426105B1 (en) | 2002-07-30 |
ATE238678T1 (en) | 2003-05-15 |
TR200002113T2 (en) | 2001-01-22 |
EP1030563A2 (en) | 2000-08-30 |
BR9814027B1 (en) | 2010-11-30 |
IL136048A0 (en) | 2001-05-20 |
CA2309665A1 (en) | 1999-05-20 |
DE69814139D1 (en) | 2003-06-05 |
WO1999023889A3 (en) | 1999-08-19 |
WO1999023889A9 (en) | 2001-05-31 |
JP2001522594A (en) | 2001-11-20 |
CN1297329A (en) | 2001-05-30 |
KR100808416B1 (en) | 2008-02-29 |
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