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WO2004056792A1 - Extrait organique de ginkgo, son procede de preparation et son utilisation - Google Patents

Extrait organique de ginkgo, son procede de preparation et son utilisation Download PDF

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Publication number
WO2004056792A1
WO2004056792A1 PCT/CN2002/000802 CN0200802W WO2004056792A1 WO 2004056792 A1 WO2004056792 A1 WO 2004056792A1 CN 0200802 W CN0200802 W CN 0200802W WO 2004056792 A1 WO2004056792 A1 WO 2004056792A1
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WO
WIPO (PCT)
Prior art keywords
extract
ginkgo
water
ginkgo biloba
content
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/CN2002/000802
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English (en)
Chinese (zh)
Inventor
Yuanhui Fu
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PRO-HERB GmbH
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PRO-HERB GmbH
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Filing date
Publication date
Application filed by PRO-HERB GmbH filed Critical PRO-HERB GmbH
Priority to PCT/CN2002/000802 priority Critical patent/WO2004056792A1/fr
Priority to AU2002349731A priority patent/AU2002349731A1/en
Publication of WO2004056792A1 publication Critical patent/WO2004056792A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
    • 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
    • A61K36/16—Ginkgophyta, e.g. Ginkgoaceae (Ginkgo family)

Definitions

  • the present invention relates to ginkgo biloba extract, and more particularly, the present invention relates to a ginkgo biloba extract that conforms to the standards of organic products and has no residual organic solvents and metal ions, and a preparation method and application thereof. Background technique
  • Ginkgo biloba is the leaf of the Ginkgo biloba plant (Ginkgo biloba L.). In recent years, due to the discovery of its effect on cardiovascular and cerebrovascular diseases, it has caused widespread concern, and extensive research has been conducted on it worldwide.
  • Ginkgo biloba contains more than 70 active ingredients, among which Quercetin, Isorhamnetin, Kaempferol, Ginkgetin, and Isoflavone are identified.
  • Quercetin, Isorhamnetin, Kaempferol, Ginkgetin, and Isoflavone are identified.
  • Ginkgolides A, B, C Ginkgolides A, B, C
  • Bilobalide Billerobalide
  • the pharmacological activity of the above monomer components is similar to that of the ginkgo biloba described above, but their effects are not as good as those of the ginkgo biloba extract. This phenomenon is considered to be due to the synergy between the above active ingredients, and some of the components whose structure has not been determined may also play an important role.
  • Ginkgo biloba can also be applied directly, but because the content of the active ingredient is relatively low, and the content of the active ingredient may be changed directly, the effect is not stable.
  • Ginkgo biloba also contains ingredients such as Ginkgolic acids, which have a strong allergenicity. Therefore, considering the convenience, efficacy, cost, and reduction of adverse reactions, it is expected that the application of Ginkgo biloba extract in the form of extracts, and the active ingredients in the extracts should be close to the natural composition ratio, and the number of adverse reactions should be minimized. Ginkgo acid content. For a long time, a lot of research has been done to extract the effective ingredients of Ginkgo biloba. E.g:
  • DE 2117429A (1972) discloses a method for preparing a ginkgo biloba extract by extracting ginkgo biloba leaves with aqueous acetone, treating it with carbon tetrachloride, methyl ethyl ketone, and denatured ethanol, and then using Pb (OH) ⁇ t, and then An extract was obtained after work-up.
  • EP1163908A1 discloses a water-soluble ginkgo biloba extract complex, which is compounded with N-methylglucosamine and ginkgo biloba extract, thereby improving the water solubility of the complex.
  • WO00 / 01397 discloses a water-soluble ginkgo extract, which is obtained by dissolving a common ginkgo extract with alcohol-water and then using an ultrafiltration method. Its water solubility can reach more than 10% w / w (w / w).
  • the method disclosed in DE 2117429A can stably extract most of the active ingredients of Ginkgo biloba, but its operation steps are long, and the precipitation method of lead hydroxide is used.
  • the extract inevitably contains organic compounds such as ketones and the like. Residues of solvents, lead salts, etc. have long-term consequences for ginkgo extracts that require long-term use.
  • EP1163908A1 introduced N-methylglucamine in Ginkgo biloba extract. Although the purpose of improving water solubility was achieved, the original composition of Ginkgo biloba extract was lost, and N-methylglucamine accounted for more than 1/3. The content of active ingredients must be reduced.
  • the object of the present invention is to provide a ginkgo biloba extract and a preparation method thereof, which can remove toxic and harmful allergenic substances while keeping the activity of ginkgo biloba leaves as good as possible without the intervention and pollution of any organic solvents and heavy metals.
  • the inventors have conducted long-term research and found that the above objects can be achieved by adopting the following invention.
  • a ginkgo biloba extract whose total flavonoid content is more than 24% w / w, the ginkgolide content is more than 4% w / w, and the room temperature water solubility is 1.2 based on the active ingredient.
  • % w / w or more its ginkgo acid content is below 5 ppm, lead and other heavy metals content is below 3 ppm, and it does not contain organic solvents.
  • a first aspect of the present invention provides a method for preparing the ginkgo extract of the first aspect, which is extracted with water, and does not use organic solvents and heavy metal salts in the extraction process, and at least includes:
  • Another aspect of the present invention is a food or a medicine containing the above-mentioned extract of the present invention.
  • Another aspect of the present invention is a method for treating cardiovascular and cerebrovascular diseases by using the above-mentioned extract of the present invention, which comprises administering a therapeutically effective amount of the above-mentioned ginkgo extract to a patient in need of treatment.
  • Figure 1 is an HPLC chromatogram (fingerprint) of the flavonoid fraction of the extract of the example.
  • FIG. 2 is an HPLC chromatogram (fingerprint) of the lactone portion of the extract of the example.
  • Fig. 3 is an HPLC chromatogram (fingerprint) of the ginkgoic acid portion of the extract of the example.
  • a ginkgo biloba extract having a high content of effective ingredients and a very low content of undesirable components (allergenic substances, heavy metals, etc.) is provided.
  • the ginkgo extract refers to an extract obtained from fresh leaves or dried leaves of the plant Ginkgo biloba L.
  • Ginkgo biloba For Ginkgo biloba, it can be understood that the various components contained in Ginkgo biloba leaves will obviously have different composition, content, proportion, etc., depending on their growing season. Moreover, the climate and degree of each region will obviously have an impact. It is common knowledge in the art to determine the optimal harvesting time in various places through actual harvesting and determination of the content ratios of various components, which will not be described in detail here.
  • the ginkgo extract of the present invention obtained from the above raw materials has a total flavonoid content of 24% w / w or more and a ginkgolide content of 4% w / w or more based on the active ingredients.
  • Ginkgo acid content is below 5ppm, and lead and other heavy metals are below 3ppm.
  • the total flavonoid content refers to the flavonoid aglycone component in the ginkgo extract represented by Quercetin, Isorhamnetin, Kaempferol, etc. processed and measured according to the standard of EP2002, 2.2.29. Total content. This determination does not exclude the presence of other types of flavonoids in the extract of the present invention, nor does it mean that only aglycones are contained in the extract of the present invention. In fact, research shows that the flavonoid component is unique to Ginkgo and it is likely to have a unique effect on the pharmacological effects of Ginkgo.
  • the total flavonoid content is not less than 24% w / w, preferably above 26, and most preferably above 26.6%.
  • Total lactone content refers to ginkgo extracts represented by Ginkgolides A, B, C (Ginkgolides A, B, C), Bilobalide, etc., processed and measured according to EP2002, 2.2.29 standards.
  • the total content of lactone ingredients This determination does not exclude the presence of other types of lactone components in the extracts of the invention.
  • the inventors have found that the lactone components represented by ginkgolides and ginkgolides are important for improving the therapeutic effect.
  • the lactone component is 4% w / w or more, preferably Above 5% w / w, it can also reach 6% w / w or higher.
  • Ginkgo acid content refers to the total content of allergenic substances that must be controlled in ginkgo biloba extract such as ginkgo acid 1 (a, b) and ginkgo acid 2 treated and measured according to EP2002, 2.2.29 standard.
  • Ginkgo biloba acid is the main substance sensitized by Ginkgo biloba extract. In the present invention, its content should be controlled below 5 ppm (that is, the content per kilogram of the extract is not higher than 5 mg), preferably below 4 ppm.
  • the extract of the present invention is used clinically In 2900 cases, no allergic reaction occurred. In contrast, according to literature reports, 11080 cases of EGb761 clinical trials, 170 cases of allergic reactions occurred, the incidence rate was 1.53% w / w.
  • the content of heavy metals such as lead refers to the total content of lead (Pb), thorium (Cd), mercury (Hg), etc. contained in the extracts measured in accordance with ⁇ 35LMBG 00.00-19 / 3 and ⁇ 35LMBG 00.00-19 / 4.
  • the content of heavy metals such as lead is less than 1 ppm, and more preferably, it contains substantially no lead and heavy metals, that is, the content is 0.5 ppm or less, and more preferably 0.2 ppm or less.
  • the content of lead and heavy metals is not higher than the background content of local air and water without increasing its content.
  • the therapeutic effect can be improved, while the content of allergenic substances is low, and the content of heavy metals such as lead is reduced to a range below a trace amount, which is also significant for long-term use.
  • a second aspect of the present invention provides a method for efficiently and simply preparing the ginkgo extract of the first aspect.
  • the biggest feature of the extraction method of the present invention is that the extraction is performed with water, and organic solvents and heavy metal salts are not used in the extraction process.
  • the extraction method of the present invention includes the following steps:
  • the first step of the extraction method of the present invention is that the ginkgo biloba leaves are soaked with saturated lime water and then extracted with pure water.
  • the present invention it is important to soak the ginkgo leaves with saturated lime water. Its head The following are the first, which help rehydrate Ginkgo biloba. Because according to the method of the present invention, fresh leaves or dried leaves can usually be used, but from the production point of view, fresh leaves are difficult to be stored for a long time, so they are usually dried or dried to become dried leaves for preservation, Weight loss and weight loss. After fully immersed in saturated lime water, the cells can fully absorb water and swell, which can help extract the active substances. Soaking with lime water can also wash away the dust adsorbed on the surface of ginkgo leaves, thereby reducing the possibility of pollution.
  • the water used for extraction can also be tap water, preferably soft water, and more preferably water with a low ion concentration, such as purified water, including distilled water, deionized water, and the like.
  • purified water including distilled water, deionized water, and the like.
  • magnetic field treatment, electric field treatment, or boiling and cooling can also be used to reduce the association between water molecules, thereby improving the extraction efficiency.
  • the extraction can be performed at room temperature or with slight heating. From the standpoint of maintaining the activity of the extract and preventing hydrolysis of the active ingredient, it is preferable to lower the extraction temperature. From the viewpoint of accelerating the extraction speed, higher temperature is preferred. Therefore, in terms of the balance of the two, in order to speed up the extraction speed and prevent hydrolysis, it is preferably carried out under a slight heating, specifically the temperature range is between 40 ° C and 70 ° C.
  • the amount of water used in the extraction can be appropriately selected in accordance with the experience of those skilled in the art according to the dryness and wetness of the ginkgo leaves, the water content of the ginkgo leaves, and the like, and there is no particular limitation. but It should be understood that extraction with too little water is not easy, and post-treatment with too much water is difficult. Generally, it can be appropriately selected between 5 to 20 times the weight of dried ginkgo leaves, preferably about 5 to 15 times the weight, and most preferably about 8 to 10 times.
  • the extraction time is not particularly limited, but too short a time may cause insufficient extraction, too long time, and the active ingredients will not be further dissolved out, so it is generally between 0.5-5 hours, which can be selected according to the specific extraction situation.
  • step 2) After the extraction solution is obtained by extraction, the residue is separated and removed to obtain an extraction solution.
  • the extraction liquid is processed in step 2): a step of removing macromolecules by ultrafiltration and reverse osmosis.
  • the extraction liquid Before the second step), because the extraction liquid may also contain relatively large impurities such as suspended residues, cell wall fragments, etc., the extraction liquid must be filtered and micro-filtered. It is filtering through cotton yarn, filter paper, porcelain core funnel, etc., or with the aid of diatomaceous earth. This step is only for improving the efficiency of the subsequent ultrafiltration step, and is not necessary for extracting the extract of the present invention.
  • the above filtration can be performed under normal pressure, pressure or reduced pressure, for example, under 5 atmospheres.
  • the pre-treated extract was purified by ultrafiltration. Ultrafiltration is performed in stages to remove inactive materials of different molecular weights in order from large to small.
  • an ultrafiltration membrane such as a commercially available filter membrane such as polypropylene hollow fiber
  • the above ultrafiltration can be performed at, for example, not more than 5 atmospheres, for example, at 0.2 to 0.5 MPa.
  • the above steps can also be changed.
  • the above steps can also be simplified into two steps, and the first step can be set to 7,000 or 8, 000, step 2 is set at 2,000 or 3,000, etc.
  • the cut-off molecular weight of the first step is set at 8,000 or 9,000, the second step is set at 5,000 or 4,000, the third step is set at 1,000, and so on.
  • Reverse osmosis filtration can be performed through various semi-permeable membranes according to the conventional reverse osmosis method. For example, using cellulose acetate reverse osmosis membrane under 4.5MPa pressure. Reverse osmosis filtration can remove heavy metal plasma and small molecule sugars to facilitate subsequent operations. The reverse osmosis pressure can be selected according to actual needs.
  • Step 3) A step of removing the sensitized substance (such as alkylphenol) by passing the filtered extract through an adsorption column.
  • the sensitized substance such as alkylphenol
  • allergenic substances such as ginkgoic acid are removed by chromatography according to the present invention.
  • the ginkgo acid is adsorbed by chromatography, and a further purified extract is obtained. Therefore, as long as the adsorbent can adsorb ginkgoic acid and does not react with active substances such as flavonoids and terpene lactones in the extract, it can be used as a stationary phase. Specific examples include macroporous resins, activated carbon, and the like, and activated carbon is preferred. The present inventors have particularly found that it is most advantageous if activated carbon made from ginkgo husk (inner seed coat) can effectively adsorb ginkgo acid without introducing other components into the extract.
  • the chromatography may be performed by, for example, a method in which the extraction solution is passed through an adsorption column under normal pressure, pressure, or reduced pressure. From the point of view of continuous chromatography and economical considerations, radial flow chromatography is preferred. This can be achieved, for example, from the top to the bottom through gravity-filled columns filled with ginkgo shell activated carbon.
  • Step 4) A process of concentration as required. After filtration, microfiltration and ultrafiltration purification, The extraction liquid obtained through the steps of reverse osmosis filtration and adsorption extraction can be further concentrated by methods such as reverse osmosis, and then dried to obtain a solid product.
  • the extract of the present invention can be obtained by distilling off the water in the extract under reduced pressure, or the product can be obtained by freeze-drying. In addition, it can be further concentrated by reverse osmosis. Thereafter, a solid extract is obtained by a conventional method such as spray drying.
  • the extract of the present invention obtained according to the above method can itself be filled into capsules or made into tablets or the like, and used as medicines or quasi medicines, health products, etc. for treating or preventing diseases. Because the extract of the present invention has good water solubility, it can also be made into a drug or similar product for J31, which can be suitable for patients who have difficulty swallowing. In addition, the extract can also be used as an additive in foods, cosmetics, and combined with other drugs.
  • Another aspect of the present invention is a method for treating cardiovascular and cerebrovascular diseases by using the above-mentioned extract of the present invention, which comprises administering a therapeutically effective amount of the above-mentioned ginkgo extract, a preparation thereof, or a product containing the extract to a patient in need of treatment, because the present invention extracts
  • the product has good water solubility while maintaining the activity of the ginkgo extract, so it can be effectively used to treat various diseases known to the ginkgo extract.
  • Residual separation at 03 ⁇ 0.5MPa Under pressure, use cotton yarn filtration, ceramic microfiltration, ultrafiltration with 10,000 grade ultrafiltration membrane (polypropylene hollow fiber), and then ultrafiltration through ultrafiltration membranes with a molecular weight of 6,000 and 2,000. At a pressure of 4.5 MPa, the filtrate was passed through a reverse osmosis membrane of cellulose acetate reverse osmosis membrane (with a salt permeability of 95% w / w or more and a water permeability of 90 ⁇ 120L / m 2 h) for reverse osmosis filtration.
  • Flavonoids, lactones and ginkgoic acid were determined by HPLC.
  • HPLC conditions According to the method of EP2002, 2.2.29, the detection wavelength was 365nm.
  • Figure 1 is an HPLC chromatogram of the flavonoid fraction of the extract of the example.
  • the peak that appears at a retention time of about 5 minutes is quercetin, the peak at about 8.3 minutes is kaempferol, and about 9 minutes is isorhamnetin. ,
  • Figure 1 is an HPLC chromatogram of the lactone portion of the extract of the example.
  • the peak that appears at about 8 minutes of retention time is Ginkgolide C
  • the peak at about 10 minutes is ginkgolide
  • the peak at about 12 minutes is Ginkgolide Ester A
  • the peak at around 16 minutes was Ginkgolide B.
  • Figure 3 is an HPLC color chart of the ginkgo acid portion of the extract of the example.
  • the peak with a retention time of about 28.8 minutes is ginkgoic acid 1 (a), and the peak at about 29.4 minutes is ginkgo alcohol; 1 (b), no ginkgo is detected.
  • Acid 2
  • each component is as follows, total flavonoids: 26.695% w / w, of which quercetin 13.591% w / w, isorhamnetin 4.494% w / w, kaempferol 8.609% w / w; total terpene lactones: 6.12% w / w, where ginkgolides, B, C 3.54% w / w, ginkgolides 2.58% w / w; ginkgolic acid 1 (a, b) are 0.39ppm, 3.37ppm, and ginkgolic acid 2 ⁇ 0.3ppm; Determination of lead, cadmium, and mercury in heavy metals was less than 0.12, 0.10, and 0.08 mg / kg, respectively.

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Abstract

L'invention concerne un extrait organique de ginkgo avec un total de flavone dépassant 24 % en poids et de ginkgolide dépassant 4 % en poids, d'après les principes efficaces. L'hydrosolubilité de cette invention est supérieure à 1,2 g/100 ml. L'extrait est obtenu par extraction d'eau sans solvant organique ou métaux lourds.
PCT/CN2002/000802 2002-11-11 2002-11-11 Extrait organique de ginkgo, son procede de preparation et son utilisation Ceased WO2004056792A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/CN2002/000802 WO2004056792A1 (fr) 2002-11-11 2002-11-11 Extrait organique de ginkgo, son procede de preparation et son utilisation
AU2002349731A AU2002349731A1 (en) 2002-11-11 2002-11-11 An organic extract of ginkgo, and the preparation method and use thereof

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PCT/CN2002/000802 WO2004056792A1 (fr) 2002-11-11 2002-11-11 Extrait organique de ginkgo, son procede de preparation et son utilisation

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005105122A1 (fr) * 2004-04-29 2005-11-10 Goetect Gmbh Extrait de ginkgo biloba et procede pour le produire

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1129218A (zh) * 1995-11-15 1996-08-21 庚朋 一种从银杏叶中提取总黄酮的方法
CN1281856A (zh) * 2000-07-08 2001-01-31 刘征涛 微波提取银杏黄酮和银杏内酯类物质的方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1129218A (zh) * 1995-11-15 1996-08-21 庚朋 一种从银杏叶中提取总黄酮的方法
CN1281856A (zh) * 2000-07-08 2001-01-31 刘征涛 微波提取银杏黄酮和银杏内酯类物质的方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005105122A1 (fr) * 2004-04-29 2005-11-10 Goetect Gmbh Extrait de ginkgo biloba et procede pour le produire

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