AU2003269064C1 - Method for producing an avocado leaf extract rich in furanic lipids - Google Patents
Method for producing an avocado leaf extract rich in furanic lipids Download PDFInfo
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- AU2003269064C1 AU2003269064C1 AU2003269064A AU2003269064A AU2003269064C1 AU 2003269064 C1 AU2003269064 C1 AU 2003269064C1 AU 2003269064 A AU2003269064 A AU 2003269064A AU 2003269064 A AU2003269064 A AU 2003269064A AU 2003269064 C1 AU2003269064 C1 AU 2003269064C1
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- 244000025272 Persea americana Species 0.000 title claims description 38
- 235000008673 Persea americana Nutrition 0.000 title claims description 29
- 150000002632 lipids Chemical class 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000000284 extract Substances 0.000 title description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 43
- 239000000419 plant extract Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 230000018044 dehydration Effects 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 11
- 238000001172 liquid--solid extraction Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 230000003204 osmotic effect Effects 0.000 claims description 4
- 241000091577 Mexicana Species 0.000 claims description 3
- GVBNSPFBYXGREE-CXWAGAITSA-N Visnadin Chemical compound C1=CC(=O)OC2=C1C=CC1=C2[C@@H](OC(C)=O)[C@@H](OC(=O)[C@H](C)CC)C(C)(C)O1 GVBNSPFBYXGREE-CXWAGAITSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 235000015241 bacon Nutrition 0.000 claims description 2
- 238000004320 controlled atmosphere Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- 244000264897 Persea americana var. americana Species 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 201000001245 periodontitis Diseases 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/54—Lauraceae (Laurel family), e.g. cinnamon or sassafras
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/02—Pretreatment
- C11B1/04—Pretreatment of vegetable raw material
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medical Informatics (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Mycology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Microbiology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Medicines Containing Plant Substances (AREA)
- Extraction Or Liquid Replacement (AREA)
- Fats And Perfumes (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
Description
r 4i IN THE MATTER OF AN AUSTRALIAN Application corresponding to PCT Application PCT/FR2003/ 002377 I, Francis AHNER, c/o CABINET REGIMBEAU, of 20 rue de Chazelles, F-75847 PARIS CEDEX 17, FRANCE, do solemnly and sincerely declare that I am conversant with the English and French languages and that to the best of my knowledge and belief the following is a true and correct translation of the PCT Application filed under No. PCT/ FR2003/ 002377.
Date February 10, 2004 Francis AHNER 004920303 1 0 METHOD FOR PRODUCING AN AVOCADO LEAF EXTRACT c RICH IN FURANIC LIPIDS ct The present invention relates to a method for producing an avocado leaf plant extract rich in furanic lipids.
5 Avocado comprises, in a known manner, particular lipids of the furan type, 0 whose main component is a linoleic furan: Thus, the expression "avocado furanic lipids" is understood to mean according to the invention the components corresponding to the formula:
IR
0 in which R is a linear C 11
-C
19 preferably C 13
-C
17 hydrocarbon chain which is saturated or which comprises one or more ethylenic or acetylenic unsaturations. These avocado furanic lipids have been described in particular in Farines, M et al, 1995, J. of Am. Oil Chem. Soc. 72, 473.
Currently, the known routes of synthesis for producing furanic lipids and the routes commonly used starting from avocados in the form of fruits as raw material.
Given the therapeutic value of avocado furanic lipids for their beneficial and curative action on the connective tissue, in particular in inflammatory pathologies such as osteoarthritis, periodontitis and scleroderma, and their high cost in general, a strong interest therefore exists in finding alternative routes for preparing these avocado furanic lipids.
The Applicant has thus developed a method which makes it possible to obtain an avocado leaf plant extract rich in furanic lipids, namely having a content ranging from to 80%, and preferably 30 to 004920303 2 O This method, in which the raw material consists of avocado leaves, comprises cI the following steps: a liquid-solid extraction step followed by evaporation under vacuum, and a heat treatment step between 80 and 120 0
C.
5 These two steps may be carried out in this order or in the reverse order.
NO The avocado leaves may be obtained from avocado plants belonging to the following varieties: Hass, Fuerte, Ettinger, Bacon, Nabal, Anaheim, Lula, Reed, Zutano, Queen, Criola Selva, Mexicana Canta, Region Dschang, Hall, Booth, Peterson, Collinson Red or Alpha Krome and more particularly to the varieties Hass, Fuerte and 0 Reed.
Several solvents may be used during the step of liquid-solid extraction of the leaves, having previously been optionally subjected to dehydration. The solvents may be chosen from the group consisting of alkanes, halogenated alkanes, ethers, esters, alcohols, aromatic compounds and supercritical fluids. Hexane, ethanol, methanol, chloroform, dichloromethane and ethyl acetate are preferred, alone or in the form of a mixture.
The heat treatment step, whether it takes place directly on the leaves or at the plant extract stage, is carried out at temperatures of between 80 and 120 0 C. This heat treatment may last from 5 to 72 hours.
According to the method of the invention, the heat treatment step may be performed in the presence or otherwise of an acid catalyst.
The expression acid catalysts is understood to mean in a broad sense socalled homogeneous inorganic or organic catalysts such as hydrochloric, sulphuric, acetic or para-toluenesulphonic acids, but also, and preferably, heterogeneous solid catalysts such as silica, alumina, silicas-aluminas, zirconias, zeolites and acidic resins.
Acidic aluminas with large specific surface areas, that is to say at least equal to 200 m2/g, will be chosen in particular.
004920303 3 The method may also comprise a step, prior to the liquid-solid extraction, of dehydration of avocado leaves.
The expression dehydration of the avocado leaves is understood to mean more generally all the techniques known to persons skilled in the art which make it possible to extract water from a compound. Among these techniques, there may be mentioned drying under a hot air stream or under a controlled atmosphere (e.g.
nitrogen) at atmospheric pressure or under vacuum, in a thick layer or in a thin layer, but also microwave drying, spray-drying, freeze-drying and osmotic dehydration in solution (direct osmosis) or in solid phase drying in osmotic bags).
0 In general, the temperature during this dehydration step will be preferably maintained, whatever the technique used, at less than or equal to 80 0
C.
Moreover, it is preferable, in the context of the present invention, to stop the dehydration when the residual moisture reaches the level of In the context of the present invention, for the sake of ease of industrial implementation and for cost considerations, drying in ventilated dryers, in a thin layer and under a hot air stream, at a temperature of between 70 and 750C. is preferred. The duration of the operation may vary from 5 to 72 hours.
According to a first variant, the method is carried out according to the succession of steps below: Step 1: heat treatment of the avocado leaves, Step 2: liquid-solid extraction of the avocado leaves, Step 3: vacuum evaporation of the solvent until a solvent-free plant extract is obtained.
According to a second variant, the method is carried out according to the succession of steps below: Step 1: liquid-solid extraction of the avocado leaves, 004920303 4 O Step 2: vacuum evaporation of the solvent until a solvent-free plant extract is N' obtained, Step 3: heat treatment of the plant extract.
According to final variant, the method is carried out according to the 5 succession of steps below: Step 1: dehydration of the avocado leaves,
NO
C Step 2: liquid-solid extraction of the avocado leaves, Step 3: vacuum evaporation of the solvent until a plant extract is obtained, Step 4: heat treatment of the plant extract.
The leaves are advantageously ground before any operation performed in the context of the method according to the invention.
The present invention finally relates to an avocado leaf plant extract which can be obtained by the method according to the invention, including according to all its variants.
The following non-limiting examples illustrate the invention.
EXAMPLE 1 One kilogram of leaves of avocado plant of the Hass variety is carefully ground. The ground product obtained (320 g) is brought into contact with 2 liters of ethanol and then heated under reflux for 5 hours. Once cool, the mixture is filtered on a Buchner funnel and the cake is washed with three times 100 ml of ethanol. The solvent is then evaporated under vacuum using a rotary evaporator, and then drawn off under vacuum for a further one hour after complete removal of the solvent. The extract obtained is then placed in an oven at 100 0 C for 24 hours, and then analysed. 23 g of extract are obtained according to this method.
The physicochemical and chromatographic analyses of this extract gave the following results: 004920303 incineration residue: <0.1% Scontent of volatile compounds: <0.1% content of furanic lipids: 42% EXAMPLE 2 .O 5 One kilogram of leaves of avocado plant of the Fuerte variety is carefully ground. The ground product obtained (305 g) is brought into contact with 2 liters of N hexane and then heated under reflux for 5 hours. Once cool, the mixture is filtered on a Buchner funnel and the cake is washed with three times 100 ml of hexane. Once assembled, the hexane-containing phases are dried in the presence of Na 2
SO
4 The 0 hexane is then evaporated under vacuum using a rotary evaporator, and then drawn off under vacuum for a further one hour after complete removal of the solvent. The extract obtained is then placed in an oven at 100'C. for 24 hours, and then analysed. 26 g of extract are obtained according to this method.
The physicochemical and chromatographic analyses of this extract gave the following results: incineration residue: <0.1% content of volatile compounds: <0.1% content of furanic lipids: 46% EXAMPLE 3 One kilogram of leaves of avocado plant of the Hass variety is carefully ground. The ground product is brought into contact, with stirring, for 5 hours, with liters of methanol, 10 liters of chloroform and 10 liters of salt water (containing 1% of NaCI). The mixture is then centrifuged and the solid pellet removed. The bottom liquid phase is recovered and then dried over Na 2
SO
4 The solvents are then evaporated under vacuum using a rotary evaporator, and then drawn off under vacuum for a further one hour after complete removal of the solvents. The extract obtained is then placed in an oven at 100 0 C for 24 hours, and then analysed. 21 g of extract are obtained according to this method.
004920303 6 The physicochemical and chromatographic analyses of this extract gave the following results: incineration residue: <0.1% Scontent of volatile compounds: <0.1% content of furanic lipids: 46% EXAMPLE 4 One kilogram of leaves of avocado plant of the Hass variety is carefully ground. The ground product is then dried in an oven, under a hot air stream, at 110°C for 24 hours. 302 g of dry matter are then recovered. The latter is then brought into 0 contact with 2 liters of hexane and then heated under reflux for 5 hours. Once cool, the mixture is filtered on a Buchner funnel and the cake is washed with three times 100 ml of hexane. The hexane is then evaporated under vacuum using a rotary evaporator, and then drawn off under vacuum for a further one hour after complete removal of the solvent. 31 g of extract are obtained according to this method.
The physicochemical and chromatographic analyses of this extract gave the following results: incineration residue: <0.1% content of volatile compounds: <0.1% content of furanic lipids: 41% EXAMPLE One kilogram of leaves of avocado plant of the Hass variety is carefully ground. The ground product is then dried in an oven, under a hot air stream, at 70 0 C for 72 hours. 315 g of dry matter are then recovered. The residual moisture present in the leaves is then This dehydrated material is then brought into contact with 2 liters of hexane and then heated under reflux for 5 hours. Once cool, the mixture is filtered on a Buchner funnel and the cake is washed with three times 100 ml of hexane. The hexane is then evaporated under vacuum using a rotary evaporator, and then drawn off under vacuum for a further one hour after complete removal of the solvent. The extract 004920303 7 obtained is then placed in an oven at 100'C for 24 hours, and then analysed. 23 g of extract are thus obtained according to this method.
The physicochemical and chromatographic analyses of this extract gave the following results: incineration residue: <0.1% content of volatile compounds: <0.1% content of furanic lipids: 38% COMPARATIVE EXAMPLE METHOD WITHOUT EXCESSIVE HEATING OF THE LEAVES Example: one kilogram of leaves of avocado plant of the Hass variety is carefully ground. The ground product is then dried in an oven, under a hot air stream, at for 96 hours. 307 g of dry matter are then recovered. The latter is then brought into contact with 2 liters of hexane and then heated under reflux for 5 hours. Once cool, the mixture is filtered on a Buchner funnel and the cake is washed with three times 100 ml of hexane. The hexane is then evaporated under vacuum using a rotary evaporator, at 60°C, and then drawn off under vacuum for a further one hour after complete removal of the solvent. 27 g of extract are obtained according to this method.
The physicochemical and chromatographic analyses of this extract gave the following results: incineration residue: <0.1% content of volatile compounds: <0.1% content of furanic lipids: 2% Conclusion: in the absence of extensive heating of the leaves, or of the plant extract obtained from the fresh or dehydrated leaves by a solvent extraction, the final extract obtained contains practically no furanic lipids (content considerably less than 005161596 7a 00 oO As used herein, except where the context requires otherwise, the term "comprise" and variations of the term, such as "comprising", "comprises" and "comprised", are not intended to exclude other additives, components, integers or steps.
Reference to any prior art in the specification is not, and should not be taken as, ,0 5 an acknowledgment, or any form of suggestion, that this prior art forms part of the 0 common general knowledge in Australia or any other jurisdiction or that this prior art c could reasonably be expected to be ascertained, understood and regarded as relevant 0 by a person skilled in the art.
Claims (18)
1. A method for producing a plant extract comprising 20 to 80% furanic Slipids, wherein the raw material consists of avocado leaves and the method comprising: \exposing leaves to a solvent in a liquid-solid extraction step followed by 01 5 evaporation under vacuum, and ICN 0a heat treatment step between 80°C. and 1200C. for a period of time, it being c possible for these two steps to be carried out in this order or in the reverse order.
2. The method of claim 1 for producing a plant extract comprising 20 to furanic lipids, wherein the avocado leaves are obtained from avocado plants belonging to the following varieties: Hass, Fuerte, Ettinger, Bacon, Nabal, Anaheim, Lula, Reed, Zutano, Queen, Criola Selva, Mexicana Canta, Region Dschang, Hall, Booth, Peterson, Collinson Red or Alpha Krome.
3. The method of claim 1 or 2 for producing a plant extract comprising to 80% furanic lipids, wherein the heat treatment is carried for a period varying between 5 and 72 hours.
4. The method according to any one of claims 1 to 3 for producing a plant extract comprising 20 to 80% furanic lipids, wherein the appropriate solvent or solvents during the liquid-solid extraction step are chosen from the group consisting of alkanes, halogenated alkanes, ethers, esters, alcohols, aromatic compounds and supercritical fluids. The method according to any one of claims 1 to 3 for producing a plant extract comprising 20 to 80% furanic lipids, wherein the appropriate solvent or solvents during the liquid-solid extraction step are selected from the group consisting of hexane, ethanol, methanol, chloroform, dichloromethane, and ethyl acetate, taken alone or in the form of a mixture. 005161596 00 9
6. A method for producing a plant extract comprising 20 to 80% furanic lipids, the method comprising: Step 1: dehydrating avocado leaves, Step 2: liquid-solid extracting of said avocado leaves using a solvent, ,O 5 Step 3: vacuum evaporating said solvent until a plant extract is obtained, 0 Step 4: heat treating said plant extract at a temperature between 80 0 C and q 120 0 C.
7. Plant extract of avocado leaves which is obtained by the method according to any one of claims 1 to
8. The method according to any one of claims 1 to 5 wherein said heat treating step is performed in the presence of an acid catalyst.
9. The method according to any one of claims 1 to 5 where said leaves are ground before any step in the described method is performed. The method of claim 6 where said dehydrating step is performed at a temperature that is less than or equal to
11. The method of claim 6 or 10 where said dehydrating step is stopped when the residual moisture reaches the level of
12. The method according to any one of claims 6, 10 or 11 where said leaves are ground before any step in the described method is performed.
13. The method according to any one of claims 6, 10, 11 or 12 where said heat treating step is performed in the presence of an acid catalyst.
14. The method according to any one of claims 6 or 10 to 13 for producing a plant extract comprising 20 to 80% furanic lipids, wherein the avocado leaves are obtained from avocado plants belonging to the following varieties: Hass, Fuerte, 00516159E 00 Ettinger, Bacon, Nabal, Anaheim, Lula, Reed, Zutano, Queen, Criola Selva, Mexicana S Canta, Region Dschang, Hall, Booth, Peterson, Collinson Red or Alpha Krome. The method according to any one of claims 6 or 10 to 14 for producing a plant extract comprising 20 to 80% furanic lipids, wherein the heat treatment is carried 3 for a period varying between 5 and 72 hours. N16. The method according to any one of claims 6 or 10 to 15 for producing a (Ni plant extract comprising 20 to 80% furanic lipids, wherein the appropriate solvent or Ssolvents during the liquid-solid extraction step are chosen from the group consisting of alkanes, halogenated alkanes, ethers, esters, alcohols, aromatic compounds and supercritical fluids.
17. The method according to any one of claims 6 or 10 to 15 for producing a plant extract comprising 20 to 80% furanic lipids, wherein the appropriate solvent or solvents during the liquid-solid extraction step are chosen from the group consisting of hexane, ethanol, methanol, chloroform, dichloromethane, and ethyl acetate, taken alone or in the form of a mixture.
18. The method according to any one of claims 6 or 10 to 17 for producing a plant extract comprising 20 to 80% furanic lipids, wherein the dehydration is selected from the group consisting of drying under a heated air stream, drying under a controlled atmosphere, drying at atmospheric pressure under vacuum, drying the avacado leaves in a layer, microwave drying, spray-drying, freeze-drying, and osmotic dehydration in solution and osmotic dehydration in solid phase.
19. The method according to any one of claims 6 or 10 to 17 for producing a plant extract comprising 20 to 80% furanic lipids, wherein the dehydration consists in drying the avocado leaves in ventilated dryers, in a layer of the avocado leaves and under a hot air stream, at a temperature between 70'C and Plant extract of avocado leaves which is obtained by the method according to according to any one of claims 6 or 10 to 19. S005161596 00 O (N \O O 5 ^D (N
21. A method according to claim 1, substantially as hereinbefore described with reference to any one of Examples 1 to
22. A method according to claim 6, substantially as hereinbefore described with reference to any one of Examples 1 to
23. A plant extract according to claims 7 or 20, substantially as hereinbefore described.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/206,995 | 2002-07-30 | ||
| FR02/09666 | 2002-07-30 | ||
| FR0209666A FR2843027B1 (en) | 2002-07-30 | 2002-07-30 | PROCESS FOR OBTAINING AN EXTRACT OF AVOCADO LEAVES RICH IN FURNA LIPIDS |
| US10/206,995 US6733795B2 (en) | 2002-07-30 | 2002-07-30 | Method for producing an avocado leaf extract rich in furanic lipids |
| PCT/FR2003/002377 WO2004012752A2 (en) | 2002-07-30 | 2003-07-28 | Method for producing avocado leaves extract rich in furan lipids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2003269064A1 AU2003269064A1 (en) | 2004-02-23 |
| AU2003269064B2 AU2003269064B2 (en) | 2008-06-05 |
| AU2003269064C1 true AU2003269064C1 (en) | 2009-01-08 |
Family
ID=31497206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003269064A Ceased AU2003269064C1 (en) | 2002-07-30 | 2003-07-28 | Method for producing an avocado leaf extract rich in furanic lipids |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1526861B1 (en) |
| JP (1) | JP2006505515A (en) |
| KR (1) | KR100944059B1 (en) |
| AR (1) | AR040738A1 (en) |
| AU (1) | AU2003269064C1 (en) |
| BR (1) | BRPI0313419B8 (en) |
| CA (1) | CA2493981C (en) |
| DE (1) | DE60317679T2 (en) |
| ES (1) | ES2295624T3 (en) |
| IL (1) | IL166568A0 (en) |
| MX (1) | MXPA05001237A (en) |
| WO (1) | WO2004012752A2 (en) |
| ZA (1) | ZA200501528B (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050158294A1 (en) | 2003-12-19 | 2005-07-21 | The Procter & Gamble Company | Canine probiotic Bifidobacteria pseudolongum |
| US9089576B2 (en) | 2004-04-30 | 2015-07-28 | Laboratoires Expanscience | Medicament comprising a peptide extract of avocado, which is intended for the treatment and prevention of illnesses that are linked to an immune system deficiency or oxidative stress or skin ageing or dry skin |
| FR2869541B1 (en) | 2004-04-30 | 2007-12-28 | Expanscience Sa Lab | USE OF A COMPOSITION COMPRISING D-MANNOHEPTULOSE AND / OR PERSEITOL FOR THE TREATMENT AND PREVENTION OF DISEASES ASSOCIATED WITH A CHANGE IN INITIATED IMMUNITY |
| EP2124966B1 (en) * | 2007-02-01 | 2015-09-09 | IAMS Europe B.V. | Method for decreasing inflammation and stress in a mammal using glucose antimetabolites, avocado or avocado extracts |
| WO2008093302A2 (en) * | 2007-02-01 | 2008-08-07 | The Iams Company | Method for decreasing inflammation and oxidative stress in mammals |
| FR2948565B1 (en) | 2009-07-30 | 2011-10-28 | Expanscience Lab | COSMETIC COMPOSITION FOR THE TREATMENT OF ACNE COMPRISING A PETIDIC EXTRACT FROM SCHIZANDRA |
| FR2948566B1 (en) | 2009-07-30 | 2012-08-10 | Expanscience Lab | EXTRACT OF SCHIZANDRA SPHENANTHERA FRUIT AND COSMETIC, DERMATOLOGICAL AND NUTRACEUTICAL COMPOSITIONS COMPRISING SAME |
| FR2953136B1 (en) | 2009-11-30 | 2012-05-11 | Expanscience Lab | EXTRACT OF VIGNA UNGUICULATA SEEDS AND COSMETIC, PHARMACEUTICAL, DERMATOLOGICAL, NUTRACEUTICAL OR FOOD COMPOSITIONS COMPRISING THE SAME |
| FR2953135B1 (en) | 2009-11-30 | 2012-05-11 | Expanscience Lab | MACROSTACHYA ACACIA SEED EXTRACT AND COSMETIC, PHARMACEUTICAL, DERMATOLOGICAL, NUTRACEUTICAL OR FOOD COMPOSITIONS COMPRISING THE SAME |
| FR2953722B1 (en) | 2009-12-16 | 2012-03-09 | Expanscience Lab | COMPOSITION COMPRISING AT LEAST ONE C7 SUGAR FOR THE TREATMENT OF ALOPECIA, FOR THE COSMETIC TREATMENT OF PHANES, AND FOR THE CARE OF HAIR, CILES OR NAILS |
| FR2969495B1 (en) | 2010-12-22 | 2013-10-11 | Expanscience Lab | EXTRACT OF MACA-RICH AERIAL PARTS OF POLYPHENOLS AND COMPOSITION COMPRISING THE SAME |
| FR2969496B1 (en) | 2010-12-22 | 2013-11-08 | Expanscience Lab | EXTRACT OF PULP AND / OR AVOCADO SKIN RICH IN POLYPHENOLS AND COSMETIC, DERMATOLOGICAL AND NUTRACEUTICAL COMPOSITIONS COMPRISING SAME |
| FR2975004B1 (en) | 2011-05-13 | 2013-06-28 | Expanscience Lab | NEW ANTI-REDNESS ACTIVE INGREDIENTS AND COSMETIC COMPOSITIONS COMPRISING THE SAME |
| FR2999429B1 (en) | 2012-12-18 | 2015-01-02 | Expanscience Lab | EXTRACT OF PASSIFLORE SEEDS AND COSMETIC, PHARMACEUTICAL, DERMATOLOGICAL OR NUTRACEUTICAL COMPOSITIONS COMPRISING SAME |
| FR3001889B1 (en) | 2013-02-11 | 2021-02-12 | Expanscience Lab | USE OF A COMPOSITION CONTAINING AVOCADO PERSEOSE IN THE PROTECTION OF EPIDERMAL STEM CELLS. |
| FR3011008B1 (en) | 2013-09-24 | 2017-12-29 | Expanscience Lab | METHODS OF EVALUATING DELETER EFFECTS OF UV ON CHILD'S SKIN |
| FR3010906B1 (en) | 2013-09-25 | 2016-12-23 | Expanscience Lab | LIPID EXTRACT OF PASSIFLOWER SEEDS |
| FR3016373B1 (en) | 2014-01-10 | 2018-01-19 | Laboratoires Expanscience | MAMMELON SKIN MODEL RECONSTITUTES |
| FR3028764B1 (en) | 2014-11-26 | 2016-12-09 | Expanscience Lab | PEPTIDE AND OSIDIC FRUIT EXTRACT OF SCHIZANDRA AND IMPROVEMENT OF THE NEUROSENSORY SKIN SYSTEM RESPONSE |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262163A (en) * | 1991-07-03 | 1993-11-16 | Laboratoires Pharmascience | Process for preparing the nonsaponifiable matter of avocado enabling in one of its fractions termed H to be improved |
| US6133313A (en) * | 1998-04-27 | 2000-10-17 | The Regents Of The University Of California | Insecticidal avocadofurans and triolein |
| WO2001021605A2 (en) * | 1999-09-22 | 2001-03-29 | Laboratoires Pharmascience | Method for extracting compounds of furan lipids and polyhydroxylated fatty alcohols of avocado, composition based on said compounds and use of said compounds in therapy, cosmetics and food |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3906994B2 (en) * | 2003-05-07 | 2007-04-18 | ソニー株式会社 | Information processing apparatus and method, recording medium, and program |
-
2003
- 2003-07-28 KR KR1020057001721A patent/KR100944059B1/en not_active Expired - Lifetime
- 2003-07-28 BR BRPI0313419A patent/BRPI0313419B8/en not_active IP Right Cessation
- 2003-07-28 WO PCT/FR2003/002377 patent/WO2004012752A2/en not_active Ceased
- 2003-07-28 CA CA2493981A patent/CA2493981C/en not_active Expired - Fee Related
- 2003-07-28 AU AU2003269064A patent/AU2003269064C1/en not_active Ceased
- 2003-07-28 MX MXPA05001237A patent/MXPA05001237A/en active IP Right Grant
- 2003-07-28 JP JP2004525476A patent/JP2006505515A/en active Pending
- 2003-07-28 DE DE60317679T patent/DE60317679T2/en not_active Expired - Lifetime
- 2003-07-28 ES ES03750850T patent/ES2295624T3/en not_active Expired - Lifetime
- 2003-07-28 EP EP03750850A patent/EP1526861B1/en not_active Expired - Lifetime
- 2003-07-30 AR AR20030102742A patent/AR040738A1/en active IP Right Grant
-
2005
- 2005-01-30 IL IL16656805A patent/IL166568A0/en active IP Right Grant
- 2005-02-22 ZA ZA2005/01528A patent/ZA200501528B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262163A (en) * | 1991-07-03 | 1993-11-16 | Laboratoires Pharmascience | Process for preparing the nonsaponifiable matter of avocado enabling in one of its fractions termed H to be improved |
| US6133313A (en) * | 1998-04-27 | 2000-10-17 | The Regents Of The University Of California | Insecticidal avocadofurans and triolein |
| WO2001021605A2 (en) * | 1999-09-22 | 2001-03-29 | Laboratoires Pharmascience | Method for extracting compounds of furan lipids and polyhydroxylated fatty alcohols of avocado, composition based on said compounds and use of said compounds in therapy, cosmetics and food |
Non-Patent Citations (2)
| Title |
|---|
| FARINES et al. J of American Oil Chemists' Society, vol. 72 (4), 1995, p.p. 473-476 * |
| PICCARDI N. et al. J Invest. Dermatol., vol. 117 (2), 2001, p.p. 398 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006505515A (en) | 2006-02-16 |
| WO2004012752A2 (en) | 2004-02-12 |
| IL166568A0 (en) | 2006-01-15 |
| ES2295624T3 (en) | 2008-04-16 |
| BR0313419A (en) | 2005-07-19 |
| EP1526861B1 (en) | 2007-11-21 |
| CA2493981A1 (en) | 2004-02-12 |
| EP1526861A2 (en) | 2005-05-04 |
| AR040738A1 (en) | 2005-04-20 |
| AU2003269064A1 (en) | 2004-02-23 |
| MXPA05001237A (en) | 2005-06-08 |
| KR20050038612A (en) | 2005-04-27 |
| AU2003269064B2 (en) | 2008-06-05 |
| ZA200501528B (en) | 2005-11-30 |
| CA2493981C (en) | 2012-06-26 |
| BRPI0313419B8 (en) | 2021-05-25 |
| BRPI0313419B1 (en) | 2015-06-09 |
| DE60317679T2 (en) | 2008-10-30 |
| DE60317679D1 (en) | 2008-01-03 |
| KR100944059B1 (en) | 2010-02-24 |
| WO2004012752A3 (en) | 2004-04-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE INVENTION TITLE TO READ METHOD FOR PRODUCING AN AVOCADO LEAF EXTRACT RICH IN FURANIC LIPIDS |
|
| DA2 | Applications for amendment section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN TH E STATEMENT(S) FILED 14 AUG 2008. |
|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 14 AUG 2008 |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |