CN108514576B - Folium Mori extract prepared by ultrasonic extraction technology and its application - Google Patents

Folium Mori extract prepared by ultrasonic extraction technology and its application Download PDF

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CN108514576B
CN108514576B CN201810323488.XA CN201810323488A CN108514576B CN 108514576 B CN108514576 B CN 108514576B CN 201810323488 A CN201810323488 A CN 201810323488A CN 108514576 B CN108514576 B CN 108514576B
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ethanol solution
mulberry leaf
pharmaceutical composition
volume fraction
eluting
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丁邦东
钱语怡
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Shanghai Shizhuangyuan Biotechnology Co.,Ltd.
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    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
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    • A61K36/185—Magnoliopsida (dicotyledons)
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    • A—HUMAN NECESSITIES
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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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Abstract

The invention relates to a mulberry leaf extract prepared by utilizing an ultrasonic extraction technology and application thereof, wherein the preparation method of the mulberry leaf extract comprises the following steps: (1) crushing dried mulberry leaves, uniformly mixing with a proper amount of yeast powder and alpha-acetolactate decarboxylase, adding a proper amount of water, adjusting the pH value to 6.0, fermenting at the temperature of 30-40 ℃ for 24-48 hours, adding an ethanol solution with the volume fraction of 95%, performing ultrasonic extraction for 3-5 hours, filtering, and concentrating the filtrate to obtain a crude extract; (2) adsorbing the crude extract obtained in the step (1) by macroporous resin, eluting 2 column volumes (removing impurities) by using ethanol solution with the volume fraction of 5-10%, eluting 3-5 column volumes by using ethanol solution with the volume fraction of 40-60%, collecting eluent, decoloring by using activated carbon, concentrating and drying to obtain the mulberry leaf extract.

Description

Folium Mori extract prepared by ultrasonic extraction technology and its application
Technical Field
The invention belongs to the field of traditional Chinese medicine extraction, and particularly relates to a mulberry leaf extract prepared by an ultrasonic extraction technology and application thereof.
Background
Folium mori, also known as "shenxiancao", has the effects of nourishing yin, activating blood, dispelling wind, dissipating heat, clearing lung-heat and relieving cough according to the records of classical Chinese medicine works in China. Modern medicine shows that mulberry leaves have a plurality of pharmacological actions such as anti-aging, blood fat reducing, blood sugar reducing and the like. The mulberry leaf contains fat, polysaccharide, fiber and the like, and the chemical components comprise vitamins, amino acids, alkaloids, flavonoid compounds, phytosterol and the like.
Complement is a group of thermolabile, activated, enzymatically active proteins that mediate immune and inflammatory responses present in human and animal serum or tissue fluids. Normally, complement exists in the form of an enzyme element, and functions mainly to attack foreign pathogens and clear immune complexes, and to maintain the body balance. However, abnormal activation of the complement system can cause excessive reaction of the human immune system, resulting in damage to the normal tissues of the human body and inflammatory reaction, which are important mediators of autoimmune inflammatory reaction. Therefore, the development of an extract or a compound having complement inhibitory activity has been a hot point of research.
Disclosure of Invention
The invention provides a mulberry leaf flavone extract, which is characterized in that the preparation method of the mulberry leaf flavone extract comprises the following steps:
(1) crushing dried mulberry leaves, uniformly mixing with a proper amount of yeast powder and alpha-acetolactate decarboxylase, adding a proper amount of water, adjusting the pH value to 6.0, fermenting at the temperature of 30-40 ℃ for 24-48 hours, adding an ethanol solution with the volume fraction of 95%, performing ultrasonic extraction for 3-5 hours, filtering, and concentrating the filtrate to obtain a crude extract;
(2) adsorbing the crude extract obtained in the step (1) by macroporous resin, eluting 2 column volumes (removing impurities) by using ethanol solution with the volume fraction of 5-10%, eluting 3-5 column volumes by using ethanol solution with the volume fraction of 40-60%, collecting eluent, decoloring by using activated carbon, concentrating and drying to obtain the mulberry leaf flavone extract.
The crushing in the step (1) is preferably to 20-80 meshes, each kilogram of mulberry leaves uses 60-80 g of yeast powder and 8-10 g of alpha-acetolactate decarboxylase, each kilogram of mulberry leaves uses 1.2-1.5L of water and 2.0-3.0L of 95 percent ethanol solution, and the ultrasonic frequency is 30-50 kHz;
the model of the macroporous resin in the step (2) is preferably HPD-826, HPD-722, AB-8 or D101.
The content of the compound 1 in the mulberry leaf flavone extract is more than 11%, and the structure of the compound 1 is as follows:
Figure BDA0001624117940000021
another embodiment of the present invention provides a method for preparing a mulberry leaf flavone extract, which is characterized by comprising the steps of:
(1) crushing dried mulberry leaves, uniformly mixing with a proper amount of yeast powder and alpha-acetolactate decarboxylase, adding a proper amount of water, adjusting the pH value to 6.0, fermenting at the temperature of 30-40 ℃ for 24-48 hours, adding an ethanol solution with the volume fraction of 95%, performing ultrasonic extraction for 3-5 hours, filtering, and concentrating the filtrate to obtain a crude extract;
(2) adsorbing the crude extract obtained in the step (1) by macroporous resin, eluting 2 column volumes (removing impurities) by using ethanol solution with the volume fraction of 5-10%, eluting 3-5 column volumes by using ethanol solution with the volume fraction of 40-60%, collecting eluent, decoloring by using activated carbon, concentrating and drying to obtain the mulberry leaf flavone extract.
The crushing in the step (1) is preferably to 20-80 meshes, each kilogram of mulberry leaves uses 60-80 g of yeast powder and 8-10 g of alpha-acetolactate decarboxylase, each kilogram of mulberry leaves uses 1.2-1.5L of water and 2.0-3.0L of 95 percent ethanol solution, and the ultrasonic frequency is 30-50 kHz;
the model of the macroporous resin in the step (2) is preferably HPD-826, HPD-722, AB-8 or D101.
The total content of the compound 1 in the mulberry leaf flavone extract is more than 11%, and the structure of the compound 1 is as follows:
Figure BDA0001624117940000022
the other embodiment of the invention provides application of the mulberry leaf flavone extract in preparing anti-complement medicines.
Another embodiment of the present invention provides a pharmaceutical composition, which is characterized in that the pharmaceutical composition comprises the above mulberry leaf flavone 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 method for isolating Compound 1 from a mulberry leaf flavone extract, characterized by comprising the steps of:
dissolving the folium Mori flavone extract (prepared by the above method) with 1-2 times of methanol, performing Sephadex LH-20 gel column chromatography, and eluting with eluent at volume ratio of 1: 1 CH2Cl2and/MeOH mixed solvent, eluting 2 times of column volume, then starting to collect eluent, collecting 2 times of column volume eluent, then decompressing and concentrating, and then preparing by High Performance Liquid Chromatography (HPLC) to obtain the compound 1.
Chromatographic conditions for HPLC preparation were: the chromatographic column is Agilent C18, 9.4X 250mm, 7 μm, the flow rate is 2mL/min, and the mobile phase is MeOH: H2O＝70∶30。
Another embodiment of the present invention provides the above flavone compound 1 or a pharmaceutically acceptable salt thereof, characterized in that the structure of the compound 1 is as follows:
Figure BDA0001624117940000031
another embodiment of the present invention provides a method for preparing the above-mentioned flavone compound 1.
Another embodiment of the invention provides the use of the above-mentioned flavonoid compound 1 or a pharmaceutically acceptable salt thereof for the preparation of an anticomplementary drug.
Another embodiment of the present invention provides a pharmaceutical composition characterized in that the pharmaceutical composition comprises the above-mentioned flavone compound 1 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.
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 Mori (1.0kg) to 20-80 mesh, mixing with yeast powder (60g) and alpha-acetolactate decarboxylase (8g), adding water 1.2L, adjusting pH to 6.0, fermenting at 30 deg.C for 48 hr, adding 95% ethanol solution (3.0L), ultrasonic extracting for 3 hr (50kHz), filtering, and concentrating the filtrate to obtain crude extract;
(2) adsorbing the crude extract obtained in the step (1) by using D101 type macroporous resin, eluting 2 column volumes (removing impurities) by using ethanol solution with the volume fraction of 5%, eluting 5 column volumes by using ethanol solution with the volume fraction of 40%, collecting eluent with the volume of 5 column volumes, decoloring by using activated carbon, concentrating and drying to obtain the mulberry leaf flavone extract (752mg, hereinafter referred to as product A).
Example 2
(1) Pulverizing dried folium Mori (1.0kg) to 20-80 mesh, mixing with yeast powder (80g) and alpha-acetolactate decarboxylase (10g), adding water 1.5L, adjusting pH to 6.0, fermenting at 40 deg.C for 24 hr, adding 95% ethanol solution (2.0L), ultrasonic extracting for 5 hr (30kHz), filtering, and concentrating the filtrate to obtain crude extract;
(2) adsorbing the crude extract obtained in the step (1) by using HPD-826 type macroporous resin, eluting 2 column volumes (removing impurities) by using 10 volume percent ethanol solution, eluting 3 column volumes by using 60 volume percent ethanol solution, collecting 3 column volumes of eluent, decoloring by using activated carbon, concentrating and drying to obtain the mulberry leaf flavone extract (731mg, hereinafter referred to as a product B).
Example 3
Dissolving the folium Mori flavone extract (product A, 100mg) with 100mg methanol, loading, performing Sephadex LH-20 gel column chromatography, and eluting with eluent at volume ratio of 1: 1 CH2Cl2Eluting with MeOH mixed solvent 2 times column volume, collecting eluate 2 times column volume (3 BV and 4 BV), concentrating under reduced pressure, and performing High Performance Liquid Chromatography (HPLC) with Agilent C18,9.4 × 250mm, 7 μm, flow rate of 2mL/min, mobile phase MeOH: H2O70: 30 to give compound 1(11.2 mg).
Figure BDA0001624117940000041
Structure confirmation data: compound 1: ESIMS M/z 505.1[ M + H ]]+；1H,13The C NMR data are shown in the following table.
Process for preparation of Compound 11H,13C NMR data (Acetone-d)6，400/100MHz)
Figure BDA0001624117940000051
Example 4
Dissolving folium Mori flavone extract (product B, 100mg) with 200mg methanol, loading, performing Sephadex LH-20 gel column chromatography, and eluting with eluent at volume ratio of 1: 1 CH2Cl2Eluting with MeOH mixed solvent 2 times column volume, collecting eluate 2 times column volume (3 BV and 4 BV), concentrating under reduced pressure, and performing High Performance Liquid Chromatography (HPLC) with Agilent C18,9.4 × 250mm, 7 μm, flow rate of 2mL/min, mobile phase MeOH: H2O70: 30 to give compound 1(11.8 mg). The structure confirmation data for compound 1 is consistent with example 3.
Example 5
(1) Pulverizing dried folium Mori (1.0kg) to 20-80 mesh, adding 1.2L water, adjusting pH to 6.0, fermenting at 30 deg.C for 48 hr, adding 95% ethanol solution (3.0L), ultrasonic extracting for 3 hr (50kHz), filtering, and concentrating the filtrate to obtain crude extract;
(2) adsorbing the crude extract obtained in the step (1) by using D101 type macroporous resin, eluting 2 column volumes (removing impurities) by using ethanol solution with the volume fraction of 5%, eluting 5 column volumes by using ethanol solution with the volume fraction of 40%, collecting eluent with the volume of 5 column volumes, decoloring by using activated carbon, concentrating, and drying to obtain a product C (521 mg). And the product C contains a small amount of rutin and chlorogenic acid through HPLC analysis, and the compound 1 is not found.
The product A, B has consistent chromatographic peak by HPLC analysis, and the content of compound 1 is above 11%.
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)
Compound 1 0.121±0.020
Compound 5 >1.000
Product A 0.307±0.020
Product B 0.312±0.020
Product C >1.000
Heparin sodium 0.053±0.008
Compound 5 has the structure
Figure BDA0001624117940000061

Claims (5)

1. A mulberry leaf flavone extract is characterized in that the preparation method of the mulberry leaf flavone extract comprises the following steps:
(1) crushing dried mulberry leaves, uniformly mixing with a proper amount of yeast powder and alpha-acetolactate decarboxylase, adding a proper amount of water, adjusting the pH value to 6.0, fermenting at the temperature of 30-40 ℃ for 24-48 hours, adding an ethanol solution with the volume fraction of 95%, performing ultrasonic extraction for 3-5 hours, filtering, and concentrating the filtrate to obtain a crude extract;
(2) adsorbing the crude extract obtained in the step (1) by macroporous resin, eluting 2 column volumes by using ethanol solution with volume fraction of 5-10%, eluting 3-5 column volumes by using ethanol solution with volume fraction of 40-60%, collecting 40-60% ethanol solution eluent, decoloring by using activated carbon, concentrating and drying to obtain the mulberry leaf flavone extract; the pulverization in the step (1) is to pulverize to 20-80 meshes, and each kilogram of mulberry leaves uses 60-80 g of yeast powder and 8-10 g of alpha-acetolactate decarboxylase; per kilogram of mulberry leaves, 1.2-1.5L of water and 2.0-3.0L of 95% ethanol solution are used; the ultrasonic frequency is 30-50 kHz; the model of the macroporous resin in the step (2) is selected from HPD-826 and D101;
the total content of the compound 1 in the mulberry leaf flavone extract is more than 11%, and the structure of the compound 1 is as follows:
Figure 766674DEST_PATH_IMAGE001
。
2. the use of the mulberry leaf flavone extract of claim 1 in the preparation of an anticomplement medicament.
3. An anticomplementary pharmaceutical composition characterized in that the anticomplementary pharmaceutical composition comprises the mulberry leaf flavone extract of claim 1 as an active ingredient.
4. The pharmaceutical composition of claim 3, wherein the pharmaceutical composition further comprises a pharmaceutically acceptable excipient.
5. The pharmaceutical composition of any one of claims 3-4, wherein the pharmaceutical composition further comprises an additional anti-complement drug.
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