CN107441110B - Exocarpium citri grandis extract and application thereof in preparing anti-cancer drugs - Google Patents
Exocarpium citri grandis extract and application thereof in preparing anti-cancer drugs Download PDFInfo
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- CN107441110B CN107441110B CN201710653288.6A CN201710653288A CN107441110B CN 107441110 B CN107441110 B CN 107441110B CN 201710653288 A CN201710653288 A CN 201710653288A CN 107441110 B CN107441110 B CN 107441110B
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
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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
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/75—Rutaceae (Rue family)
- A61K36/752—Citrus, e.g. lime, orange or lemon
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Abstract
The invention relates to the technical field of pharmaceutical chemistry, and particularly discloses a pummelo peel extract and application thereof in preparation of anti-cancer drugs. The extract comprises the following effective components: the composition comprises the following components in percentage by weight: 30-40% of nobiletin; 20-30% of kaempferol; 20-30% of rhoifolin. The pummelo peel extract has definite active ingredients and contents and obvious anti-liver cancer effect.
Description
Technical Field
The invention relates to the technical field of medicinal chemistry, in particular to a pummelo peel extract and application thereof in preparing anticancer drugs.
Background
Exocarpium Citri Grandis, namely exocarpium Citri Grandis, is prepared from immature or nearly mature dry outer pericarp of Citrus grandis or fructus Citri Grandis of Rutaceae. Has effects in eliminating phlegm, relieving cough, and treating cough due to wind-cold evil.
Liver cancer, a malignant tumor of the liver, can be divided into primary and secondary types. The primary liver malignant tumor originates from the epithelium or mesenchymal tissue of the liver, and the former is called primary liver cancer, which is a malignant tumor with high incidence and great harm in China.
In the existing anticancer reports, pummelo peel medicinal materials are mostly used as one of the medicinal materials to treat cancers, and no report that the effective parts of pummelo peel are used as anticancer medicaments independently exists. For example, a Chinese medicinal composition for treating lung cancer with application No. 201310669278.3 and a Chinese medicament for treating lung cancer with application No. 201510164588.9, wherein pummelo peel is used as one of the medicinal materials for treating cancer.
Therefore, the research on an anticancer drug with good anticancer effect based on pummelo peel has wide market prospect.
Disclosure of Invention
The invention aims to solve the technical problem of providing a pummelo peel extract for overcoming the defect of an anticancer component in pummelo peel in the prior art, wherein the pummelo peel extract has a very obvious anticancer effect.
The technical problem to be solved by the invention is realized by the following technical scheme:
an exocarpium Citri Grandis extract comprises the following effective components: nobiletin, kaempferol and rhoifolin.
Preferably, the pummelo peel extract comprises the following effective components in percentage by weight: 30-40% of nobiletin; 20-30% of kaempferol; 20-30% of rhoifolin.
The preparation method of the pummelo peel extract comprises the following steps:
(1) extracting exocarpium Citri Grandis with ethanol under reflux, and concentrating the extractive solution to obtain exocarpium Citri Grandis ethanol extract;
(2) dissolving the ethanol extract of exocarpium Citri Grandis in water to obtain suspension, extracting with petroleum ether, discarding the petroleum ether extract, extracting with ethyl acetate, and concentrating the ethyl acetate extract to obtain exocarpium Citri Grandis extract;
(3) and (3) enriching the effective components of the pummelo peel extract by silica gel column chromatography to obtain the pummelo peel extract.
Preferably, the ethanol in the step (1) is an ethanol aqueous solution with a volume fraction of 80-100%; the ratio of the amount of the ethanol to the amount of the pummelo peel is 8-15 mL:1 g; the heating reflux extraction time is 1-3 h.
Preferably, in the step (2), petroleum ether with the same volume as the suspension is used for extracting for 1-3 times, the petroleum ether extract is discarded, ethyl acetate with the same volume as the suspension is used for extracting for 1-3 times, and the ethyl acetate extract is concentrated to obtain the pummelo peel extract.
Preferably, the specific method for enriching the effective components by silica gel column chromatography in the step (3) comprises the following steps: putting the pummelo peel extract into a silica gel column, and eluting and removing impurities by using a mixed solvent system consisting of a solvent A and a solvent B in a volume ratio of 90: 10-87: 13; then, eluting by using a mixed solvent system consisting of a solvent A and a solvent B in a volume ratio of 82: 18-80: 20, and collecting an eluted part to obtain an effective part of the pummelo peel; the solvent A is chloroform, and the solvent B is methanol;
the dosage of a mixed solvent system consisting of the solvent A and the solvent B with the volume ratio of 90: 10-87: 13 is 3-5 times of the volume of the silica gel column; the dosage of a mixed solvent system consisting of the solvent A and the solvent B in a volume ratio of 82: 18-80: 20 is 5-8 times of the volume of the silica gel column.
Preferably, the specific method for enriching the effective components by silica gel column chromatography in the step (3) comprises the following steps: subjecting exocarpium Citri Grandis extract to silica gel column, dissolving in solvent A at volume ratio of 87: 13: eluting a mixed solvent system consisting of the solvent B to remove impurities; then adding solvent A with the volume ratio of 82: 18: eluting with a mixed solvent system consisting of the solvent B and collecting the eluted part to obtain the effective part of the pummelo peel; the solvent A is chloroform, and the solvent B is methanol;
the dosage of a mixed solvent system consisting of the solvent A and the solvent B with the volume ratio of 87:13 is 3 times of the volume of the silica gel column; the dosage of the mixed solvent system consisting of the solvent A and the solvent B with the volume ratio of 82:18 is 8 times of the volume of the silica gel column.
The volume of the silica gel column is the volume from the column bottom to the silica gel deposition surface after the silica gel is filled into the column.
Preferably, the weight of the silica gel used in the silica gel column is 20-40 times of the dry weight of the exocarpium citri grandis extract.
The exocarpium Citri Grandis extract can be used for preparing anticancer drugs; the anti-cancer drug is an anti-liver cancer drug.
The invention also provides an anticancer medicinal composition derived from pummelo peel, which comprises the following effective components in percentage by weight: the weight ratio of the nobiletin to the kaempferol to the rhoifolin is 3-4: 2-3: 2-3; the anti-cancer drug is an anti-liver cancer drug.
Has the advantages that: the invention develops a brand new pummelo peel extract which has very obvious anti-liver cancer effect and overcomes the defect of the prior art in researching anti-cancer parts of pummelo peel; in addition, the exocarpium citri grandis extract has definite active ingredients and content, and when the exocarpium citri grandis extract is used as an anti-liver cancer drug, the quality control and the medication safety of the drug are facilitated.
Detailed Description
The present invention is further explained below with reference to specific examples, which are not intended to limit the present invention in any way.
Example 1 preparation of exocarpium Citri Grandis extract
(1) Heating and refluxing exocarpium Citri Grandis with 95% ethanol water solution by volume for 1.5 hr, and concentrating the extractive solution to obtain exocarpium Citri Grandis ethanol extract;
(2) dissolving exocarpium Citri Grandis ethanol extract in water to obtain suspension, extracting with petroleum ether of the same volume for 3 times, discarding petroleum ether extract, extracting with ethyl acetate of the same volume for 3 times, mixing the ethyl acetate extracts, and concentrating to obtain exocarpium Citri Grandis extract;
(3) subjecting exocarpium Citri Grandis extract to silica gel column chromatography to enrich effective components to obtain exocarpium Citri Grandis extract;
the method for enriching the effective components by silica gel column chromatography comprises the following steps: passing the exocarpium Citri Grandis extract through silica gel column (the weight of silica gel in silica gel column is 30 times of the dry weight of exocarpium Citri Grandis extract, and the specification of silica gel is 200 mesh), dissolving in solvent A with volume ratio of 87: 13: eluting and removing impurities in a mixed solvent system (the dosage is 3 times of the column volume) consisting of the solvent B; then adding solvent A with the volume ratio of 82: 18: eluting with a mixed solvent system (8 times of column volume) composed of solvent B, and collecting the eluted part to obtain exocarpium Citri Grandis effective part; the solvent A is chloroform, and the solvent B is methanol.
Through detection, the pummelo peel extract contains 37% of nobiletin, 28% of kaempferol and 26% of rhoifolin in percentage by weight.
The content determination method of the components comprises the following steps: detecting by liquid chromatography, and detecting by external standard method with nobiletin, kaempferol and rhoifolin as standard substances.
The liquid chromatogram conditions are as follows: with Agilent Zorbax SB C18(column length 250mm, inner diameter 4.6mm, particle size 5 μm) as chromatographic column; acetonitrile is used as a mobile phase A, 0.05% acetic acid solution is used as a mobile phase B, and the detection wavelength is 330 nm; the column temperature is 25 ℃, and the flow rate is 1.0 mL/min; mobile phase A: mobile phase B15: 85. Wherein the retention time of rhoifolin is 6.3min, the retention time of kaempferol is 8.8min, and the retention time of nobiletin is14.4min。
Example 2 preparation of exocarpium Citri Grandis extract
(1) Heating and refluxing exocarpium Citri Grandis with 95% ethanol water solution by volume for 1.5 hr, and concentrating the extractive solution to obtain exocarpium Citri Grandis ethanol extract;
(2) dissolving exocarpium Citri Grandis ethanol extract in water to obtain suspension, extracting with petroleum ether of the same volume for 3 times, discarding petroleum ether extract, extracting with ethyl acetate of the same volume for 3 times, mixing the ethyl acetate extracts, and concentrating to obtain exocarpium Citri Grandis extract;
(3) subjecting exocarpium Citri Grandis extract to silica gel column chromatography to enrich effective components to obtain exocarpium Citri Grandis extract;
the method for enriching the effective components by silica gel column chromatography comprises the following steps: passing the exocarpium Citri Grandis extract through silica gel column (the weight of silica gel in silica gel column is 30 times of the dry weight of exocarpium Citri Grandis extract, and the specification of silica gel is 200 meshes), mixing the above extracts at a volume ratio of 90:10 with solvent A: eluting and removing impurities in a mixed solvent system (the dosage is 3 times of the column volume) consisting of the solvent B; then adding solvent A with the volume ratio of 82: 18: eluting with a mixed solvent system (8 times of column volume) composed of solvent B, and collecting the eluted part to obtain exocarpium Citri Grandis effective part; the solvent A is chloroform, and the solvent B is methanol.
Through detection, the pummelo peel extract contains 35% of nobiletin, 24% of kaempferol and 25% of rhoifolin by weight percentage.
Example 3 preparation of exocarpium Citri Grandis extract
(1) Heating and refluxing exocarpium Citri Grandis with 95% ethanol water solution by volume for 1.5 hr, and concentrating the extractive solution to obtain exocarpium Citri Grandis ethanol extract;
(2) dissolving exocarpium Citri Grandis ethanol extract in water to obtain suspension, extracting with petroleum ether of the same volume for 3 times, discarding petroleum ether extract, extracting with ethyl acetate of the same volume for 3 times, mixing the ethyl acetate extracts, and concentrating to obtain exocarpium Citri Grandis extract;
(3) subjecting exocarpium Citri Grandis extract to silica gel column chromatography to enrich effective components to obtain exocarpium Citri Grandis extract;
the method for enriching the effective components by silica gel column chromatography comprises the following steps: passing the exocarpium Citri Grandis extract through silica gel column (the weight of silica gel in silica gel column is 30 times of the dry weight of exocarpium Citri Grandis extract, and the specification of silica gel is 200 meshes), mixing the above extracts at a volume ratio of 90:10 with solvent A: eluting and removing impurities in a mixed solvent system (the dosage is 3 times of the column volume) consisting of the solvent B; then adding a solvent A with a volume ratio of 80: 20: eluting with a mixed solvent system (8 times of column volume) composed of solvent B, and collecting the eluted part to obtain exocarpium Citri Grandis effective part; the solvent A is chloroform, and the solvent B is methanol.
Through detection, the pummelo peel extract contains 32 weight percent of nobiletin, 21 weight percent of kaempferol and 22 weight percent of rhoifolin.
Example 4 extract anticancer Activity assay
Culturing human liver cancer cell BEL-7404 in culture medium (RPMI 1640 culture medium) at a ratio of 10 × 103Each well was placed in a 96 well plate containing 5% CO at 37 deg.C2The original culture medium is sucked off after the wall is attached after the culture for 24 hours in the incubator. Then adding RPMI 1640 culture medium containing 10% fetal bovine serum into the blank group; the experimental groups are respectively added into RPMI 1640 culture media containing 0.01-100 mug/mL of drugs to be detected; after further culturing for 48 hours, MTT was added at a concentration of 5mg/mL, further culturing was carried out for 4 hours, the supernatant was aspirated, 100. mu.L of DMSO was added, the mixture was left in the dark for 10 minutes, the absorbance was measured at 570nm using a microplate reader (Sunrise), and the survival of the cells was calculated from the absorbance, with 6 duplicate wells for each treatment. Cell survival rate (%). DELTA.ODDrug treatment group/ΔODBlank groupX 100. The semi-Inhibitory Concentration (IC) of the cells was then calculated from the dose-response curve50) The results are shown in Table 1. The drugs in the experimental groups were as follows: experimental group 1 used nobiletin alone; experimental group 2 kaempferol alone; experiment group 3 used rhoifolin alone; experiment group 4 used composition 1 consisting of nobiletin, kaempferol and rhoifolin in a weight ratio of 3:2: 2; experiment group 5 used composition 2 consisting of nobiletin, kaempferol and rhoifolin in a weight ratio of 4:2: 2; in experimental group 6, nobiletin, kaempferol and rhoifolin were used in a weight ratio of 4:3:3, composition 2; experimental group 7 the pummelo peel extract prepared in example 1 was used; experimental group 8 the pummelo peel extract prepared in example 2 was used; experimental group 9 the pummelo peel extract prepared in example 3 was used.
TABLE 1 IC of drugs on human hepatoma cells BEL-740450Test results
As can be seen from experimental groups 1-6 in Table 1, nobiletin, kaempferol and rhoifolin have certain anti-liver cancer effects when used alone, and when the nobiletin, kaempferol and rhoifolin are mixed according to the proportion of the invention, the anti-liver cancer effects are more remarkable, which shows that the nobiletin, kaempferol and rhoifolin can generate synergistic anti-cancer effects after being mixed. Therefore, the combination of nobiletin, kaempferol and rhoifolin can be used as an anti-liver cancer drug.
As can be seen from experimental groups 7-9 in Table 1, the exocarpium citri grandis extract has a very significant anti-liver cancer effect, which is stronger than that of any monomer, and the effective components of the exocarpium citri grandis extract, namely nobiletin, kaempferol and rhoifolin generate a synergistic anti-liver cancer effect. Therefore, the invention develops the pummelo peel extract with very excellent anti-liver cancer effect and definite effective components for the first time, and the extract can be used as an anti-liver cancer medicament.
Claims (9)
1. The pummelo peel extract is characterized by comprising the following effective components in percentage by weight: 30-40% of nobiletin; 20-30% of kaempferol; 20-30% of rhoifolin.
2. The method of producing an exocarpium Citri Grandis extract according to claim 1, comprising the steps of:
(1) extracting exocarpium Citri Grandis with ethanol under reflux, and concentrating the extractive solution to obtain exocarpium Citri Grandis ethanol extract;
(2) dissolving the ethanol extract of exocarpium Citri Grandis in water to obtain suspension, extracting with petroleum ether, discarding the petroleum ether extract, extracting with ethyl acetate, and concentrating the ethyl acetate extract to obtain exocarpium Citri Grandis extract;
(3) and (3) enriching the effective components of the pummelo peel extract by silica gel column chromatography to obtain the pummelo peel extract.
3. The preparation method according to claim 2, wherein the ethanol in the step (1) is an aqueous ethanol solution with a volume fraction of 80-100%; the ratio of the amount of the ethanol to the amount of the pummelo peel is 8-15 mL:1 g; the heating reflux extraction time is 1-3 h.
4. The preparation method according to claim 2, wherein in the step (2), petroleum ether with the volume equal to that of the suspension is used for extraction for 1-3 times, the petroleum ether extract is discarded, ethyl acetate with the volume equal to that of the suspension is used for extraction for 1-3 times, and the ethyl acetate extract is concentrated to obtain the pummelo peel extract.
5. The preparation method according to claim 2, wherein the specific method for enriching the effective components by silica gel column chromatography in the step (3) comprises the following steps: putting the pummelo peel extract into a silica gel column, and eluting and removing impurities by using a mixed solvent system consisting of a solvent A and a solvent B in a volume ratio of 90: 10-87: 13; then, eluting by using a mixed solvent system consisting of a solvent A and a solvent B in a volume ratio of 82: 18-80: 20, and collecting an eluted part to obtain an effective part of the pummelo peel; the solvent A is chloroform, and the solvent B is methanol;
the dosage of a mixed solvent system consisting of the solvent A and the solvent B with the volume ratio of 90: 10-87: 13 is 3-5 times of the volume of the silica gel column; the dosage of a mixed solvent system consisting of the solvent A and the solvent B in a volume ratio of 82: 18-80: 20 is 5-8 times of the volume of the silica gel column.
6. The preparation method according to claim 5, wherein the specific method for enriching the effective components by silica gel column chromatography in the step (3) comprises the following steps: subjecting exocarpium Citri Grandis extract to silica gel column, dissolving in solvent A at volume ratio of 87: 13: eluting a mixed solvent system consisting of the solvent B to remove impurities; then adding solvent A with the volume ratio of 82: 18: eluting with a mixed solvent system consisting of the solvent B and collecting the eluted part to obtain the effective part of the pummelo peel; the solvent A is chloroform, and the solvent B is methanol;
the dosage of a mixed solvent system consisting of the solvent A and the solvent B with the volume ratio of 87:13 is 3 times of the volume of the silica gel column; the dosage of the mixed solvent system consisting of the solvent A and the solvent B with the volume ratio of 82:18 is 8 times of the volume of the silica gel column.
7. The method according to claim 5, wherein the silica gel used in the silica gel column is 20 to 40 times the dry weight of the exocarpium Citri Grandis extract.
8. Use of the exocarpium Citri Grandis extract of claim 1 in the preparation of anticancer drugs; the anti-cancer drug is an anti-liver cancer drug.
9. An anticancer medicinal composition derived from pummelo peel is characterized by comprising the following effective components in percentage by weight: the weight ratio of the nobiletin to the kaempferol to the rhoifolin is 3-4: 2-3: 2-3; the anti-cancer drug is an anti-liver cancer drug.
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