WO2012045400A1 - An extract of the fruit of the plant schisandra chinensis - Google Patents

An extract of the fruit of the plant schisandra chinensis Download PDF

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Publication number
WO2012045400A1
WO2012045400A1 PCT/EP2011/004761 EP2011004761W WO2012045400A1 WO 2012045400 A1 WO2012045400 A1 WO 2012045400A1 EP 2011004761 W EP2011004761 W EP 2011004761W WO 2012045400 A1 WO2012045400 A1 WO 2012045400A1
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Prior art keywords
extract
weight
organic phase
schisandra chinensis
fruits
Prior art date
Application number
PCT/EP2011/004761
Other languages
French (fr)
Inventor
Diana Polacek
Johannes Crotogino
Smail Alaoui Ismaili
Original Assignee
Cognis Ip Management Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis Ip Management Gmbh filed Critical Cognis Ip Management Gmbh
Publication of WO2012045400A1 publication Critical patent/WO2012045400A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
    • C07G1/00—Lignin; Lignin derivatives
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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)
    • A61K36/79—Schisandraceae (Schisandra family)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/50—Methods involving additional extraction steps
    • A61K2236/55—Liquid-liquid separation; Phase separation

Definitions

  • the present invention relates to a process for making an extract of the fruits of the plant Schisandra chinensis, it relates to the extract obtainable by this process and it relates to the therapeutic and to the non-therapeutic use of this extract, or of a functional food or a dietary supplement comprising the extract, for reducing the weight of a human or of an animal.
  • Extracts of the fruits of the plant Schisandra chinensis and their use for weight control are known.
  • WO 2005/044289 discloses an extract of the fruit of the plant Schisandra chinensis. Specifically, an extract obtained by extracting fruits of Schisandra chinensis with a mixture of 75 % by weight ethanol and 25 % by weight water and an extract obtained with supercritical carbon dioxide is disclosed. Furthermore the cosmetic use of this extracts is disclosed.
  • WO 2009/021622 discloses an extract of the fruit of the plant Schisandra chinensis and its use in weight control. Specifically, an extract obtained with 95 % ethanol and ethyl acetate (for extracting the remaining water phase after the ethanol has been removed from the extract obtained) is disclosed.
  • the international search report of WO 2009/021622 lists further documents that disclose extracts of the plant Schisandra chinensis and the use of theses extracts.
  • the problem underlying the present invention is to provide another process for making an extract of the fruits of the plant Schisandra chinensis, which extract is useful in weight reduction of a human or an animal. Furthermore the problem underlying the present invention is to provide the extract obtainable by this process.
  • Active schizandrins active with respect to weight reduction
  • the extract according to the present invention comprise 7-Tigloyl-gomisin P, Deoxyschizandrol A, Gomisin N and Schizandrin C.
  • the extracts according to the present invention may comprise schizandrins with little or no activity in weight reduction, namely Schizandrol A, Gomisin B and Gomisin G.
  • the process according to the present invention allows for making an extract with a high content of active schizandrins. It is possible to carry out the process according to the present invention in a way so that the resulting extract contains at least 20 % by weight, preferably 20 to 90 % by weight schizandrins calculated on the dry matter of the extract. Furthermore the process according to the present invention can be carried out with food-office solvents only so that the resulting extract can be used without toxicological, regulatory or other problems in food, functional food, dietary supplements etc.
  • the process according to the present invention can be carried out in a way that produces an extract that is essentially free of polycyclic aromatic hydrocarbons PAH.
  • Essentially free means less than 5 ppb, preferably less than 2 ppb PAH.
  • the extract contains less than 5 ppb, preferably less than 2 ppb benzo-a-pyrene.
  • the process according to the present invention comprises a defined cascade of liquid-liquid extractions using defined organic solvents.
  • this results in an extract having a total content of active shizandrins - calculated on the dried final product - of more than 20 and typically from 20 to 90 % by weight.
  • the weight ratio between dried plant material (fruits) and final extract typically is about 30-150.
  • the well balanced cascade of solvents avoids the use of non-food grade materials. Therefore, the extracts obtainable according to the present invention comply with the regulatory conditions for use in alimentation.
  • This step of the process is carried out in order to produce a first liquid extract from the fruits.
  • a suitable particle size 50 to 2000 um.
  • the Schisandra fruits show very small contents of active schizandrins (which belong to the group of compounds called lignans) of about 0.2 to 3 % b.w. - calculated on the dried plant material.
  • active schizandrins which belong to the group of compounds called lignans
  • lignans active schizandrins
  • the fruits are milled to small pieces.
  • aqueous Ci-C4 aliphatic alcohols especially aqueous methanol, ethanol, n-propanol, isopropylalcohol, butanol or their mixtures.
  • the water content of the alcohols can range between 1 and 50, preferably 2 and 20 and particularly between 3 and 15% w/w.
  • the preferred solvent is methanol comprising about 10 % water.
  • the amount of methanol used for the extraction can be chosen easily by the skilled person and should be sufficient to effect an extraction, which is preferably carried out in a percolator, continuous bed extractor or in a batch. A typical ratio would be 1 part by weight of dried plant material and 1 to 15 parts of solvent.
  • the extraction temperature is of course limited by the boiling point of the solvents. Typically this step is conducted at a temperature of 15 to 70, and preferably at about 25 °C.
  • the aqueous/alcoholic phase is preferably subjected to a filtration to remove the depleted plants, which are still useful as fuel for generating the heat to dry the starting material.
  • the filtrate is removed from the organic solvent to give the first extract E2, which has, after the removal of the alcohol, a water content of typically 10 to 40 % b.w.
  • the alcohol which is separated from the extract can be recycled.
  • Aqueous extract E2 that comprises the active lignans is subjected to a liquid-liquid extraction with lower paraffin hydrocarbons, in particular hexane, heptane or their mixtures.
  • the preferred solvent is heptane.
  • the extraction can be carried out at room temperature, however typically it is conducted between 20 and 50 °C. Since Schisandra comprises a number of different Schizandrins, one extraction may not be enough to transfer the total amount of lignans into the organic phase. Therefore it is particularly useful to repeat this step 2 to 10, preferably 3 to 5 times and to combine the organic phases thus obtained to give the extract Al . In the course of the repetition of this step it is not necessary to change the ratio of the solvents or the temperature.
  • extract Al may be subjected to further purification.
  • the extract is washed with water or an aqueous alkaline base and the organic phase thus obtained, A2, is subjected to concentration and drying to give the final product.
  • Schisandra may contain PAH which become enriched during the process.
  • the charcoal treatment is preferably conducted prior to the final drying of the product.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Food Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Polymers & Plastics (AREA)
  • Child & Adolescent Psychology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Obesity (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nutrition Science (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Hematology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Medical Informatics (AREA)
  • Microbiology (AREA)
  • Epidemiology (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Diabetes (AREA)

Abstract

The present invention relates to a process for making an extract of the fruits of the plant Schisandra chinensis, it relates to the extract obtainable by this process and it relates to the therapeutic and to the non-therapeutic use of this extract, or of a functional food or a dietary supplement comprising the extract, for reducing the weight of a human or of an animal.

Description

An Extract of the Fruit of the Plant Schisandra chinensis
The present invention relates to a process for making an extract of the fruits of the plant Schisandra chinensis, it relates to the extract obtainable by this process and it relates to the therapeutic and to the non-therapeutic use of this extract, or of a functional food or a dietary supplement comprising the extract, for reducing the weight of a human or of an animal.
Extracts of the fruits of the plant Schisandra chinensis and their use for weight control are known.
WO 2005/044289 (Cognis' internals file no. C 2892) discloses an extract of the fruit of the plant Schisandra chinensis. Specifically, an extract obtained by extracting fruits of Schisandra chinensis with a mixture of 75 % by weight ethanol and 25 % by weight water and an extract obtained with supercritical carbon dioxide is disclosed. Furthermore the cosmetic use of this extracts is disclosed.
WO 2009/021622 discloses an extract of the fruit of the plant Schisandra chinensis and its use in weight control. Specifically, an extract obtained with 95 % ethanol and ethyl acetate (for extracting the remaining water phase after the ethanol has been removed from the extract obtained) is disclosed. The international search report of WO 2009/021622 lists further documents that disclose extracts of the plant Schisandra chinensis and the use of theses extracts.
The problem underlying the present invention is to provide another process for making an extract of the fruits of the plant Schisandra chinensis, which extract is useful in weight reduction of a human or an animal. Furthermore the problem underlying the present invention is to provide the extract obtainable by this process.
The solution to this problem is the process according to the claims of the present patent application and the extract according to the claims of the present patent application. Both are subjects of the present invention. A further subject of the present invention is the use of the extract or the functional food or the dietary supplement according to the claims of the present patent application. Active schizandrins (active with respect to weight reduction) which are comprised in the extract according to the present invention comprise 7-Tigloyl-gomisin P, Deoxyschizandrol A, Gomisin N and Schizandrin C. Furthermore the extracts according to the present invention may comprise schizandrins with little or no activity in weight reduction, namely Schizandrol A, Gomisin B and Gomisin G.
The process according to the present invention, the extract according to the present invention and the use of this extract according to the present invention has numerous advantages. The process according to the present invention allows for making an extract with a high content of active schizandrins. It is possible to carry out the process according to the present invention in a way so that the resulting extract contains at least 20 % by weight, preferably 20 to 90 % by weight schizandrins calculated on the dry matter of the extract. Furthermore the process according to the present invention can be carried out with food-grand solvents only so that the resulting extract can be used without toxicological, regulatory or other problems in food, functional food, dietary supplements etc. Furthermore the process according to the present invention can be carried out in a way that produces an extract that is essentially free of polycyclic aromatic hydrocarbons PAH. Essentially free means less than 5 ppb, preferably less than 2 ppb PAH. In one embodiment of the present invention the extract contains less than 5 ppb, preferably less than 2 ppb benzo-a-pyrene.
The process according to the present invention comprises a defined cascade of liquid-liquid extractions using defined organic solvents. Preferably this results in an extract having a total content of active shizandrins - calculated on the dried final product - of more than 20 and typically from 20 to 90 % by weight. The weight ratio between dried plant material (fruits) and final extract typically is about 30-150. Preferably the well balanced cascade of solvents avoids the use of non-food grade materials. Therefore, the extracts obtainable according to the present invention comply with the regulatory conditions for use in alimentation.
Preferred Embodiments of the first extraction step (extracting fruits of the plant Schisandra chinensis with an aqueous CI to C4-alcohol to provide a first extract El)
This step of the process is carried out in order to produce a first liquid extract from the fruits. In order to achieve this complete fruits are first dried and milled to a suitable particle size of 50 to 2000 um. Depending on their origin the Schisandra fruits show very small contents of active schizandrins (which belong to the group of compounds called lignans) of about 0.2 to 3 % b.w. - calculated on the dried plant material. Although even plants low in lignans content can be used for the present invention it is preferred to start with raw materials having at least 0.5 % b.w. active molecules. The fruits are milled to small pieces. They are subjected to an extraction using aqueous Ci-C4 aliphatic alcohols, especially aqueous methanol, ethanol, n-propanol, isopropylalcohol, butanol or their mixtures. The water content of the alcohols can range between 1 and 50, preferably 2 and 20 and particularly between 3 and 15% w/w. The preferred solvent, however, is methanol comprising about 10 % water. The amount of methanol used for the extraction can be chosen easily by the skilled person and should be sufficient to effect an extraction, which is preferably carried out in a percolator, continuous bed extractor or in a batch. A typical ratio would be 1 part by weight of dried plant material and 1 to 15 parts of solvent. The extraction temperature is of course limited by the boiling point of the solvents. Typically this step is conducted at a temperature of 15 to 70, and preferably at about 25 °C. Once the extraction has been completed the aqueous/alcoholic phase is preferably subjected to a filtration to remove the depleted plants, which are still useful as fuel for generating the heat to dry the starting material. In a further preferred embodiment the filtrate is removed from the organic solvent to give the first extract E2, which has, after the removal of the alcohol, a water content of typically 10 to 40 % b.w. The alcohol which is separated from the extract can be recycled.
Preferred Embodiments of the liquid-liquid extraction with a hydrocarbon
Aqueous extract E2 that comprises the active lignans is subjected to a liquid-liquid extraction with lower paraffin hydrocarbons, in particular hexane, heptane or their mixtures. The preferred solvent, however, is heptane. The extraction can be carried out at room temperature, however typically it is conducted between 20 and 50 °C. Since Schisandra comprises a number of different Schizandrins, one extraction may not be enough to transfer the total amount of lignans into the organic phase. Therefore it is particularly useful to repeat this step 2 to 10, preferably 3 to 5 times and to combine the organic phases thus obtained to give the extract Al . In the course of the repetition of this step it is not necessary to change the ratio of the solvents or the temperature. Due to the fact that during the cascade of repetitions the amount of lignans in the aqueous phase is reduced the polarity changes by itself and allows extracting the next type of lignans. By means of this operation it is safeguarded that all types of required lignans being present in the extract E2 are transferred into extract Al obtaining a typical lignans profile for weight management product where for instance Gomisin N is almost totally transferred while Schizandrol A, which is not necessarily required, only a small part is transferred.
Preferred Embodiments of the purification of extract Al
Once extract Al is obtained by optionally combining all organic phases of the previous step extract Al may be subjected to further purification. Preferably, the extract is washed with water or an aqueous alkaline base and the organic phase thus obtained, A2, is subjected to concentration and drying to give the final product. Depending on the origin of the plant materials, Schisandra may contain PAH which become enriched during the process. In this case it is desirous to treat the extract with activated charcoal to adsorb PAH and/or with chelating agents such as e.g. EDTA to eliminate heavy metals by forming complexes. The charcoal treatment is preferably conducted prior to the final drying of the product.
Examples
An extract obtained from fruits of the plant Schisandra chinensis according to the preferred embodiments of the process according to the present invention as described in the previous paragraphs had the following composition:
7-Tigloyl-gomisin P 2.2 weight-%
Deoxyschizandrol A 4.6 weight-%
Gomisin N 22.4 weight-%
Schizandrin C 3.8 weight-%
Schizandrol A 2.9 weight-%
Gomisin B 4.7 weight-%
Gomisin G 2.7 weight-%
Other compounds remainder

Claims

Claims
A process for making an extract of the fruits of the plant Schisandra chinensis, wherein this process comprises
• extracting fruits of the plant Schisandra chinensis with an aqueous CI to C4- alcohol having a water content of 1 to 50 % by weight (preferably methanol containing about 10 % by weight water) to provide a first extract El,
• removing the CI to C4-alcohol from the first extract El until a water content of 10 to 50 % by weight, preferably 15 and 30 % by weight, is obtained so that a second extract E2 is obtained,
• subjecting the second extract E2 to a liquid-liquid extraction with a hydrocarbon having 5 to 10 C-atoms so that an organic phase Al and an aqueous phase E3 are obtained,
• optionally subjecting the organic phase Al to at least one liquid-liquid extraction with water so that an aqueous phase E4 and a second organic phase A2 are obtained,
• optionally submitting the organic phase Al/the second organic phase A2 to a charcoal treatment to remove PAH,
• removing the solvent from the organic phase Al/the second organic phase A2 so that the extract of the fruits of the plant Schisandra chinensis is obtained.
The process according to claim 1 , wherein the extract contains at least 20 % by weight, preferably at least 30 % by weight, more preferably at least 40 % by weight, active schizandrins calculated on the dry matter of the extract, wherein active schizandrins are compounds selected from the group consisting of 7-Tigloyl-gomisin P, Deoxyschizandrol A, Gomisin N and Schizandrin C.
The process according to claim 1 or 2, wherein the extract contains at least 10 % by weight, preferably at least 15 % by weight, more preferably at least 20 % by weight Gomisin N.
The process according to any of claims 1 to 3, wherein the extract contains at most 10 % by weight, preferably at most 5 % by weight, more preferably at most 3 % by weight Schizandrol A.
5. The process according to any of claims 1 to 4, wherein the extract is essentially free of polycyclic aromatic hydrocarbons PAH.
6. An extract obtainable by the process according to any of claims 1 to 5.
7. A functional food or a dietary supplement comprising the extract according to claim.
8. The non-therapeutic use of the extract according to claim 6 or of the functional food or of the dietary supplement according to claim 7 for reducing the weight of a human or of an animal.
9. The extract according to claim 6 or the functional food or the dietary supplement according to claim 7 for use in a method for treatment of the human or animal body by therapy, including prophylaxis.
10. The extract according to claim 6 or the functional food or the dietary supplement according to claim 7 for use in a method for treatment of the human or animal body by therapy, including prophylaxis, wherein this method a method for reducing the weight of the human or animal.
PCT/EP2011/004761 2010-10-05 2011-09-23 An extract of the fruit of the plant schisandra chinensis WO2012045400A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108339024A (en) * 2017-02-21 2018-07-31 湖南诺泽生物科技有限公司 A kind of method of harmful substance in removal plant extracts

Citations (7)

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Publication number Priority date Publication date Assignee Title
WO2002032417A1 (en) * 2000-10-19 2002-04-25 Elcom Bio Technology, Co., Ltd. Pharmaceutical preparations containing a dibenzocyclooctane lignan derivative for prevention and treatment of neurodegenerative disease
KR20040009188A (en) * 2002-07-22 2004-01-31 나도선 Inhibitor for transcription of NFAT isolated from Schisandra chinensis
WO2005044289A2 (en) 2003-11-07 2005-05-19 Cognis France, S.A.S. An extract of the fruit of schisandra chinensis and its pharmaceutical and cosmetic use
KR20060001877A (en) * 2003-07-30 2006-01-06 학교법인 인하학원 Composition comprising schizandrae fructus extract as an effective component for preventing and treating arthritis
WO2008075888A1 (en) * 2006-12-20 2008-06-26 Jung Sik Lee A composition comprising the extract of combined herbs for preventing and treating liver disease
EP2025335A1 (en) * 2007-08-16 2009-02-18 InterMed Discovery GmbH Extracts with liver-X-receptor modulators, compounds and their use in weight control and treatment of disorders of lipid metabolism
KR20090065031A (en) * 2007-12-17 2009-06-22 이정식 Composition comprising the extract of mixed herb suppressing lipid generation for preventing and treating fatty liver disease

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002032417A1 (en) * 2000-10-19 2002-04-25 Elcom Bio Technology, Co., Ltd. Pharmaceutical preparations containing a dibenzocyclooctane lignan derivative for prevention and treatment of neurodegenerative disease
KR20040009188A (en) * 2002-07-22 2004-01-31 나도선 Inhibitor for transcription of NFAT isolated from Schisandra chinensis
KR20060001877A (en) * 2003-07-30 2006-01-06 학교법인 인하학원 Composition comprising schizandrae fructus extract as an effective component for preventing and treating arthritis
WO2005044289A2 (en) 2003-11-07 2005-05-19 Cognis France, S.A.S. An extract of the fruit of schisandra chinensis and its pharmaceutical and cosmetic use
WO2008075888A1 (en) * 2006-12-20 2008-06-26 Jung Sik Lee A composition comprising the extract of combined herbs for preventing and treating liver disease
EP2025335A1 (en) * 2007-08-16 2009-02-18 InterMed Discovery GmbH Extracts with liver-X-receptor modulators, compounds and their use in weight control and treatment of disorders of lipid metabolism
WO2009021622A1 (en) 2007-08-16 2009-02-19 Intermed Discovery Gmbh Extracts with liver-x-receptor modulators, compounds and their use especially in weight control
KR20090065031A (en) * 2007-12-17 2009-06-22 이정식 Composition comprising the extract of mixed herb suppressing lipid generation for preventing and treating fatty liver disease

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DATABASE WPI Week 200436, Derwent World Patents Index; AN 2004-386444, XP002612688 *
DATABASE WPI Week 200666, Derwent World Patents Index; AN 2006-632986, XP002612687 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108339024A (en) * 2017-02-21 2018-07-31 湖南诺泽生物科技有限公司 A kind of method of harmful substance in removal plant extracts

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