CN108125995B - Ginkgo leaf flavone extract and application thereof - Google Patents

Ginkgo leaf flavone extract and application thereof Download PDF

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CN108125995B
CN108125995B CN201810081276.5A CN201810081276A CN108125995B CN 108125995 B CN108125995 B CN 108125995B CN 201810081276 A CN201810081276 A CN 201810081276A CN 108125995 B CN108125995 B CN 108125995B
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沈发治
谢伟
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ACETAR BIO-TECH Inc
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    • 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)
    • A—HUMAN NECESSITIES
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    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
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    • A61K2236/19—Preparation or pretreatment of starting material involving fermentation using yeast, bacteria or both; enzymatic treatment
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    • 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
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    • A61K2236/50—Methods involving additional extraction steps
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    • 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

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Abstract

The invention relates to a ginkgo leaf flavone extract and application thereof, and the preparation method comprises the following steps: (1) crushing dried ginkgo leaves, adding a proper amount of beta-glucosaccharase aqueous solution with the mass fraction of 6-8%, soaking for 6-8h, and then adding a mixture of beta-glucosaccharase aqueous solution and beta-glucosaccharase aqueous solution in a volume ratio of 1: 1 Anhydrous ethanol and Na2CO3Reflux-extracting the mixed solution of the solutions for 10-12h, filtering, and concentrating the filtrate to obtain crude extract; (2) dispersing the crude extract obtained in the step (1) with a proper amount of water, adjusting the pH value to 4-5 with acid, extracting with ethyl acetate, and concentrating an ethyl acetate layer to obtain an extract; (3) adsorbing the extract obtained in the step (2) by macroporous resin, eluting 3-5 column volumes by using ethanol with the volume fraction of 95%, concentrating the eluent, and drying to obtain the ginkgo leaf flavone extract.

Description

Ginkgo leaf flavone extract and application thereof
Technical Field
The invention belongs to the field of plant extraction, and particularly relates to a ginkgo leaf flavone extract and application thereof.
Background
Folium Ginkgo has mild nature, sweet, bitter and astringent taste, and has effects of astringing lung, relieving asthma, promoting blood circulation, removing blood stasis, and relieving pain. The chemical components in folium Ginkgo are complex, and the main bioactive components include flavonoids, bilobalide, organic acids, etc. The flavonoid has high content, has antioxidant, antiaging, antibacterial and antiviral effects, is safe and reliable, is healthy, and can be used for processing medicine and health food.
The research on flavonoids in ginkgo leaves is always a hotspot in the field, and the invention discloses a novel ginkgo leaf flavonoid extract.
Disclosure of Invention
The invention provides a ginkgo leaf flavone extract which is characterized by comprising the following steps:
(1) crushing dried ginkgo leaves, adding a proper amount of beta-glucosaccharase aqueous solution with the mass fraction of 6-8%, soaking for 6-8h, and then adding a mixture of beta-glucosaccharase aqueous solution and beta-glucosaccharase aqueous solution in a volume ratio of 1: 1 Anhydrous ethanol and Na2CO3Reflux-extracting the mixed solution of the solutions for 10-12h, filtering, and concentrating the filtrate to obtain crude extract;
(2) dispersing the crude extract obtained in the step (1) with a proper amount of water, adjusting the pH value to 4-5 with acid, extracting with ethyl acetate, and concentrating an ethyl acetate layer to obtain an extract;
(3) adsorbing the extract obtained in the step (2) by macroporous resin, eluting 3-5 column volumes by using ethanol with the volume fraction of 95%, concentrating the eluent, and drying to obtain the ginkgo leaf flavone extract.
Pulverizing preferably to 20-80 mesh, wherein each kg of folium Ginkgo uses beta-glucosaccharase water solution 2.0-2.5L, and each kg of folium Ginkgo uses anhydrous ethanol 4.0-5.0L, and Na2CO3The mass fraction of the solution is 3-5%;
the amount of water used in the step (2) is preferably 10-15mL of water per gram of crude extract, the acid is preferably one or two of dilute hydrochloric acid and acetic acid, the ethyl acetate is preferably extracted for 2-3 times, and the volume of the ethyl acetate used in each extraction is preferably 2-3 times of the volume of the water;
the model of the macroporous resin in the step (3) is preferably AB-8 or D101;
the content of the compounds in the formula I and the formula II in the ginkgo leaf flavone extract is more than 25 percent, and the structures of the formula I and the formula II are as follows:
Figure BDA0001559572740000021
another embodiment of the present invention provides the use of the above ginkgo biloba leaf flavonoid extract in the preparation of an anti-complement medicament.
Another embodiment of the present invention provides a pharmaceutical composition, wherein the pharmaceutical composition comprises the above ginkgo biloba leaf flavonoid extract as an active ingredient. The pharmaceutical composition also optionally comprises pharmaceutically acceptable pharmaceutic adjuvants (preferably diluents, excipients and carriers); optionally also including other anti-complement drugs; the dosage form of the pharmaceutical composition is preferably a solid preparation or a liquid preparation.
Another embodiment of the present invention provides a flavonoid compound or a pharmaceutically acceptable salt thereof, wherein the flavonoid compound has a structure represented by formula I or formula II below:
Figure BDA0001559572740000022
another embodiment of the present invention provides a process for the preparation of a compound of formula I or formula II as described above, characterized by the steps of:
(1) drying semen GinkgoCrushing leaves, adding a proper amount of beta-glucosaccharase aqueous solution with the mass fraction of 6-8%, soaking for 6-8h, and then adding a mixture of the beta-glucosaccharase aqueous solution and the beta-glucosaccharase aqueous solution in a volume ratio of 1: 1 Anhydrous ethanol and Na2CO3Reflux-extracting the mixed solution of the solutions for 10-12h, filtering, and concentrating the filtrate to obtain crude extract;
(2) dispersing the crude extract obtained in the step (1) with a proper amount of water, adjusting the pH value to 4-5 with acid, extracting with ethyl acetate, and concentrating an ethyl acetate layer to obtain an extract;
(3) adsorbing the extract obtained in the step (2) by macroporous resin, eluting 3-5 column volumes by using ethanol with the volume fraction of 95%, concentrating and drying the eluent to obtain the ginkgo leaf flavone extract;
(4) subjecting the ginkgo biloba leaf flavone extract obtained in the step (3) to Sephadex LH-20 gel column chromatography, wherein the eluent is CH2Cl2: MeOH ═ 1: 1, and preparing the compound shown in the formula I and the compound shown in the formula II by High Performance Liquid Chromatography (HPLC).
Pulverizing preferably to 20-80 mesh, wherein each kg of folium Ginkgo uses beta-glucosaccharase water solution 2.0-2.5L, and each kg of folium Ginkgo uses anhydrous ethanol 4.0-5.0L, and Na2CO3The mass fraction of the solution is 3-5%; the amount of water used in the step (2) is preferably 10-15mL of water per gram of crude extract, the acid is preferably one or two of dilute hydrochloric acid and acetic acid, the ethyl acetate is preferably extracted for 2-3 times, and the volume of the ethyl acetate used in each extraction is preferably 2-3 times of the volume of the water; the model of the macroporous resin in the step (3) is preferably AB-8 or D101; the preferred chromatographic conditions of the high performance liquid chromatography in the step (4) are that a chromatographic column is Hypersil 300A C18, 10X 250mm, 10 mu m, the flow rate is 2mL/min, and the mobile phase is MeOH: H2O＝55∶45。
In another embodiment of the invention, there is provided the use of a compound of formula I or formula II, or a pharmaceutically acceptable salt thereof, as described above, in the preparation of an anti-complement medicament.
Another embodiment of the present invention provides a pharmaceutical composition, wherein the pharmaceutical composition comprises the compound of formula I or formula II, or a pharmaceutically acceptable salt thereof, as an active ingredient. The pharmaceutical composition also optionally comprises pharmaceutically acceptable pharmaceutic adjuvants (preferably diluents, excipients and carriers); optionally also including other anti-complement drugs; the dosage form of the pharmaceutical composition is preferably a solid preparation or a liquid preparation.
The term "pharmaceutically acceptable salts" as used herein refers to non-toxic inorganic or organic acid and/or base addition salts, as described in "Salt selection for basic drugs", int.J.pharm. (1986),33, 201-217.
Compared with the prior art, the invention obtains a flavone extract by using methods of enzymolysis, alkaline alcohol extraction, acid regulation, ethyl acetate extraction and macroporous resin adsorption, wherein the extract contains two new flavone components (formula I and formula II), and the total content of the formula I and the formula II is more than 25 percent.
Drawings
FIG. 1 is an HPLC analysis chart of Ginkgo biloba leaf flavone extract product A.
Detailed Description
In order to facilitate a further understanding of the invention, the following examples are provided to illustrate it in more detail. However, these examples are only for better understanding of the present invention and are not intended to limit the scope or the principle of the present invention, and the embodiments of the present invention are not limited to the following.
Example 1
(1) Pulverizing dried folium Ginkgo (1.0kg) to 20-80 mesh, adding 6% beta-glucosidase water solution (2.5L) by mass, soaking for 8h, and adding the mixture at a volume ratio of 1: 1 Anhydrous ethanol and 3% Na2CO3Reflux-extracting the mixed solution (10L) for 12h, filtering, and concentrating the filtrate to obtain 11.2g crude extract;
(2) dispersing 10g of the crude extract obtained in the step (1) with 150mL of water, adjusting the pH to 4.0-5.0 with dilute hydrochloric acid, extracting for 2 times with ethyl acetate, combining organic phases, and concentrating to obtain 1.80g of extract;
(3) adsorbing the extract (1.80g) obtained in the step (2) by AB-8 type macroporous resin, eluting 3 column volumes by using ethanol with the volume fraction of 95%, concentrating and drying the eluent to obtain 865mg of the ginkgo leaf flavone extract, which is hereinafter referred to as a product A.
Example 2
(1) Taking dry silverCrushing apricot leaves (1.0kg) to 20-80 meshes, adding 8% of beta-glucosaccharase aqueous solution (2.0L) for soaking for 6 hours, and then adding a mixture of the components in a volume ratio of 1: 1 Anhydrous ethanol and 5% Na2CO3Reflux-extracting the mixed solution (8L) for 10h, filtering, and concentrating the filtrate to obtain 11.8g crude extract;
(2) dispersing 10g of the crude extract obtained in the step (1) with 100mL of water, adjusting the pH value to 4.0-5.0 with acetic acid, extracting with ethyl acetate for 3 times, combining organic phases, and concentrating to obtain 1.82g of extract;
(3) adsorbing the extract (1.82g) obtained in the step (2) by using D101 type macroporous resin, eluting 5 column volumes by using ethanol with the volume fraction of 95%, concentrating and drying the eluent to obtain 881mg of the ginkgo leaf flavone extract, which is hereinafter referred to as a product B.
Example 3
Subjecting product A (50mg) to Sephadex LH-20 gel column chromatography with eluent CH2Cl2: MeOH ═ 1: 1, and preparing by HPLC with Hypersil 300A C18, 10 × 250mm, 10 μm, flow rate of 2mL/min, and mobile phase of MeOH: H2O55: 45 gave compound of formula I (7.3mg) and compound of formula II (5.2mg), respectively.
Figure BDA0001559572740000041
Structural validation data for compounds of formula I: ESIMS M/z 371.1[ M + H ]]+,1H,13C NMR data are shown in the following table; data for structure confirmation of compounds of formula II: ESIMS M/z 413.1[ M + H ]]+,1H,13The C NMR data are shown in the following table.
Of formula I, II1H,13C NMR data (Acetone-d)6，400/100MHz)
Figure BDA0001559572740000051
Example 4
Subjecting product B (50mg) to Sephadex LH-20 gel column chromatography, eluting with CH2Cl2: MeOH ═ 1: 1, and preparing by HPLC with Hypersil 300A C18, 10 × 250mm, 10 μm, flow rate of 2mL/min, and mobile phase of MeOH: H2O55: 45 gave compound of formula I (7.9mg) and compound of formula II (5.0mg), respectively, with the structure confirmation data being consistent with example 3.
Example 5
And respectively taking a proper amount of product A, B for HPLC analysis, wherein the total content of the compounds of formula I and formula II is 26-28%.
Example 6
The test was performed according to the classical pathway complement inhibition assay disclosed in Chinese patent application No. 201610384844.X, which gave a 50% Concentration (CH) of the test sample required to inhibit hemolysis50) See table below.
Compound (I) CH50(mg/mL)
Formula I 0.106±0.012
Formula II 0.182±0.019
Product A 0.203±0.023
Product B 0.218±0.025
Heparin sodium 0.053±0.008

Claims (3)

1. A ginkgo biloba leaf flavone extract is characterized by comprising the following steps:
(1) crushing dried ginkgo leaves, adding a beta-glucosaccharase aqueous solution with the mass fraction of 6-8%, soaking for 6-8h, and then adding a mixture of the beta-glucosaccharase aqueous solution and the beta-glucosaccharase aqueous solution in a volume ratio of 1: 1 Anhydrous ethanol and Na2CO3Reflux-extracting the mixed solution of the solutions for 10-12h, filtering, and concentrating the filtrate to obtain crude extract;
(2) dispersing the crude extract obtained in the step (1) with water, adjusting the pH value to 4-5 with acid, extracting with ethyl acetate, and concentrating an ethyl acetate layer to obtain an extract;
(3) adsorbing the extract obtained in the step (2) by macroporous resin, eluting 3-5 column volumes by using ethanol with the volume fraction of 95%, concentrating and drying the eluent to obtain the ginkgo leaf flavone extract; the content of the compounds in the formula I and the formula II in the ginkgo leaf flavone extract is more than 25 percent, and the structures of the formula I and the formula II are as follows:
Figure FDA0002864877420000011
the pulverization in the step (1) is to pulverize to 20-80 meshes, 2.0-2.5L of beta-glucosaccharase aqueous solution is used for each kilogram of ginkgo leaves, and 4.0-5.0L of absolute ethyl alcohol and Na are used for each kilogram of ginkgo leaves2CO3The mass fraction of the solution is 3-5%; the dosage of water in the step (2) is 10-15mL of water per gram of crude extract, acid is selected from one or two of dilute hydrochloric acid and acetic acid, and ethyl acetate is used for extraction for 2-3 times; the model of the macroporous resin in the step (3) is selected from AB-8 or D101.
2. The use of the ginkgo biloba leaf flavonoid extract of claim 1 in the preparation of an anti-complement medicament.
3. A pharmaceutical composition, characterized in that the pharmaceutical composition comprises the ginkgo biloba leaf flavonoid extract of claim 1 as an active ingredient.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000234A1 (en) * 2000-06-26 2002-01-03 Xinan Zhao A pharmaceutical preparation of chinese herbs for preventing and treating cardiovascular and cerebrovascular disease and the use thereof
CN101347424A (en) * 2007-07-20 2009-01-21 复旦大学 Use of luteolin in preparing anticomplement medicament
CN102285951A (en) * 2011-09-13 2011-12-21 辽宁亿灵科创生物医药科技有限公司 Luteolin derivative and application thereof to preventing and treating cardiovascular disease
CN104906153A (en) * 2015-06-09 2015-09-16 邳州鑫源生物制品有限公司 Technological method for efficiently extracting ginkgo flavone
CN107050072A (en) * 2017-03-30 2017-08-18 辽宁吉瑞生物科技有限公司 A kind of ginkgo extract

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000234A1 (en) * 2000-06-26 2002-01-03 Xinan Zhao A pharmaceutical preparation of chinese herbs for preventing and treating cardiovascular and cerebrovascular disease and the use thereof
CN101347424A (en) * 2007-07-20 2009-01-21 复旦大学 Use of luteolin in preparing anticomplement medicament
CN102285951A (en) * 2011-09-13 2011-12-21 辽宁亿灵科创生物医药科技有限公司 Luteolin derivative and application thereof to preventing and treating cardiovascular disease
CN104906153A (en) * 2015-06-09 2015-09-16 邳州鑫源生物制品有限公司 Technological method for efficiently extracting ginkgo flavone
CN107050072A (en) * 2017-03-30 2017-08-18 辽宁吉瑞生物科技有限公司 A kind of ginkgo extract

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