CN107320554A - A kind of Exocarpium Citri Grandis extract and its application in the medicine of disease for the treatment of APE1 mediations is prepared - Google Patents
A kind of Exocarpium Citri Grandis extract and its application in the medicine of disease for the treatment of APE1 mediations is prepared Download PDFInfo
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- CN107320554A CN107320554A CN201710653287.1A CN201710653287A CN107320554A CN 107320554 A CN107320554 A CN 107320554A CN 201710653287 A CN201710653287 A CN 201710653287A CN 107320554 A CN107320554 A CN 107320554A
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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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- 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
- 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
Abstract
The present invention relates to field of pharmaceutical chemistry technology, a kind of Exocarpium Citri Grandis extract and its application in the medicine of disease for the treatment of APE1 mediations is prepared are specifically disclosed.Described Exocarpium Citri Grandis extract includes following active ingredient：Nobiletin, Quercetin and naringin.Experiment shows that the extract can effectively suppress the expression of the APE1 in lung carcinoma cell, can be used as APE1 inhibitor, the disease for treating APE1 mediations；Embodiment experiment is it is also shown that described Exocarpium Citri Grandis extract has the external effect of anti-lung cancer of highly significant；In addition, Exocarpium Citri Grandis extract active ingredient and content that the present invention is provided understand, be conducive to quality control and the drug safety of extract.
Description
Technical field
The present invention relates to field of pharmaceutical chemistry technology, and in particular to a kind of Exocarpium Citri Grandis extract and its prepare treat APE1
Application in the medicine of the disease of mediation.
Background technology
Exocarpium Citri Grandis, i.e. Huajuhong, source this product are the prematurity or maturescent dry of rutaceae Citrus grandis or shaddock
Dry outside rind.Effect with preventing phlegm from forming and stopping coughing, treatment cough due to wind-cold evil.
Lung cancer is that morbidity and mortality growth is most fast, to one of population health and the maximum malignant tumour of life threat.
At present, the essential therapeutic arsenals of lung cancer are radiation and chemotherapy, and the therapeutic alliance of wherein radiation and chemotherapy is also common treatment side
Formula.
APE1 is depurination/apurinic nucleic acid restriction endonuclease, is a kind of large biological molecule functional complex, is that DNA base is cut
It is the weight that cell chemotherapeutics is caused injury with endonuclease and redox function except the crucial rate-limiting enzyme of the approach of reparation
Want reparative factor.Existing research (the quick .APE1 effect GAP-associated protein GAPs of Zhang Zhi and its Effect study [D] in tumour radiotherapy
Third Military Medical University, 2011.) show that APE1 expression can promote Nm23-H1 expression, APE1 and Nm23- in lung carcinoma cell
H1 collaborations can repair the DNA of lung carcinoma cell, so that lung carcinoma cell produces radiotherapy or chemoresistance.Therefore, develop a kind of
Both there is APE1 expression inhibiting functions, the medicine with anti-lung cancer function has wide market prospects again.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of Exocarpium Citri Grandis extract, described Exocarpium Citri Grandis extract energy
Suppress APE1 expression and there is extraordinary anti-lung cancer effect simultaneously.
Above-mentioned technical problem to be solved by this invention, is achieved by the following technical programs：
A kind of Exocarpium Citri Grandis extract, includes following active ingredient：Nobiletin, Quercetin and naringin.
Preferably, described Exocarpium Citri Grandis extract, it is characterised in that include the active ingredient of following percentage by weight：River
Hesperetin 20~30%；Quercetin 10~20%；Naringin 30~40%.
The preparation method of above-mentioned Exocarpium Citri Grandis extract, it is comprised the following steps：
(1) Exocarpium Citri Grandis is taken, ethanol heating and refluxing extraction is used, concentrated extracting solution obtains Exocarpium Citri Grandis ethanol extract；
(2) Exocarpium Citri Grandis ethanol extract is dissolved in water into suspension, first with petroleum ether extraction, discards petroleum ether extraction
Thing, then be extracted with ethyl acetate, concentration acetic acid ethyl ester extract obtains Exocarpium Citri Grandis extract；
(3) Exocarpium Citri Grandis extract is produced into Exocarpium Citri Grandis extract through silica gel column chromatography is active constituent-enriched；
The active constituent-enriched specific method of silica gel column chromatography is in step (3)：It is first by silicagel column on Exocarpium Citri Grandis extract
It is 85 with volume ratio:15~80:The mixed solvent system of 20 solvent orange 2 A and solvent B composition carries out elution removal of impurities；Then body is used again
Product is than being 75:25~72:The mixed solvent system of 28 solvent orange 2 A and solvent B composition is eluted and collects elution position, is produced
Exocarpium Citri Grandis active component；Described solvent orange 2 A is petroleum ether, and solvent B is ethyl acetate；
Volume ratio is 85:15~80:The consumption of the mixed solvent system of 20 solvent orange 2 A and solvent B composition is silicagel column post
1~3 times of volume；Volume ratio is 75:25~72:The consumption of the mixed solvent system of 28 solvent orange 2 A and solvent B composition is silica gel
3~5 times of post column volume.
Preferably, the active constituent-enriched specific method of silica gel column chromatography is in step (3)：By silicon on Exocarpium Citri Grandis extract
Glue post, is first 80 with volume ratio:20 solvent orange 2 A：The mixed solvent system of solvent B compositions carries out elution removal of impurities；Then body is used again
Product is than being 72:28 solvent orange 2 A：The mixed solvent system of solvent B compositions is eluted and collects elution position, and producing Exocarpium Citri Grandis has
Imitate position；
Volume ratio is 80:The consumption of the mixed solvent system of 20 solvent orange 2 A and solvent B composition is the 3 of silicagel column column volume
Times；Volume ratio is 72:The consumption of the mixed solvent system of 28 solvent orange 2 A and solvent B composition is 5 times of silicagel column column volume.
The silicagel column column volume refers to after silica gel dress post, from post bottom to the volume of silica gel deposition surface.
Preferably, the weight of used silica gel is 20~40 times of Exocarpium Citri Grandis extract dry weight in step (3) silicagel column.
Preferably, the ethanol described in step (1) is the ethanol water that volume fraction is 80~100%；Described second
The consumption of alcohol and the amount ratio of Exocarpium Citri Grandis are 8~15mL:1g；The time of described heating and refluxing extraction is 1~3h；Step (2)
It is middle discard petroleum ether extract first with the petroleum ether extraction isometric with suspension 1~3 time, then with isometric with suspension
Ethyl acetate is extracted 1~3 time, and concentration acetic acid ethyl ester extract obtains Exocarpium Citri Grandis extract.
Application of the above-mentioned Exocarpium Citri Grandis extract in APE1 inhibitor is prepared.
Application of the above-mentioned Exocarpium Citri Grandis extract in the medicine of disease for the treatment of APE1 mediations is prepared；The APE1 mediations
Disease is the lung cancer that APE1 is mediated.
Application of the above-mentioned Exocarpium Citri Grandis extract in cancer therapy drug is prepared, described cancer therapy drug is anti-lung-cancer medicament.
The present invention a kind of anticancer pharmaceutical composition from Exocarpium Citri Grandis is also provided, its include Nobiletin, Quercetin with
And naringin, the weight ratio of described Nobiletin, Quercetin and naringin is 2~3：1~2：3~4；Described anticarcinogen
Thing is anti-lung-cancer medicament.
Beneficial effect：The invention provides a kind of brand-new Exocarpium Citri Grandis extract, described Exocarpium Citri Grandis extract can be effective
Suppress the expression of the APE1 in lung carcinoma cell, can be used as APE1 inhibitor, the disease for treating APE1 mediations；Implement
Example experiment is it is also shown that described Exocarpium Citri Grandis extract extract has the external effect of anti-lung cancer of highly significant；In addition, of the invention
The Exocarpium Citri Grandis extract active ingredient and content of offer understand, are conducive to quality control and the drug safety of extract.
Embodiment
The present invention is explained further below in conjunction with specific embodiment, but embodiment does not do any type of limit to the present invention
It is fixed.
The preparation of the Exocarpium Citri Grandis extract of embodiment 1
(1) Exocarpium Citri Grandis is taken, with the ethanol water heating and refluxing extraction 1.5h that volume fraction is 95%, concentrated extracting solution is obtained
Exocarpium Citri Grandis ethanol extract；
(2) Exocarpium Citri Grandis ethanol extract is dissolved in water into suspension, first with isometric petroleum ether extraction, repeats to extract
3 times, petroleum ether extract is discarded, then is extracted with isometric ethyl acetate, extraction 3 times is repeated, merges concentration ethyl acetate extraction
Thing is taken to obtain Exocarpium Citri Grandis extract；
(3) Exocarpium Citri Grandis extract is produced into Exocarpium Citri Grandis extract through silica gel column chromatography is active constituent-enriched；
The active constituent-enriched method of the silica gel column chromatography is：By (the institute in silicagel column of silicagel column on Exocarpium Citri Grandis extract
With 30 times that the weight of silica gel is Exocarpium Citri Grandis extract dry weight, the specification of silica gel is 200 mesh), it is first 80 with volume ratio:20 it is molten
Agent A：The mixed solvent system (consumption is 3 times of column volumes) of solvent B compositions carries out elution removal of impurities；Then volume ratio is used to be 72 again:
28 solvent orange 2 A：The mixed solvent system (consumption is 8 times of column volumes) of solvent B compositions is eluted and collects elution position, is produced
Exocarpium Citri Grandis active component；Described solvent orange 2 A is petroleum ether, and solvent B is ethyl acetate.
After testing, in the Exocarpium Citri Grandis extract containing percentage by weight for 28% Nobiletin, 19% Quercetin
And 37% naringin.
The content assaying method of mentioned component is (similarly hereinafter)：Using liquid chromatographic detection, with Nobiletin, Quercetin and
Naringin is measured as standard items using external standard method.
Described liquid phase chromatogram condition is：With Agilent Zorbax SB C18(column length 250mm, internal diameter 4.6mm, particle diameter 5
μm) it is chromatographic column；Using acetonitrile as mobile phase A, using 0.05% acetic acid solution as Mobile phase B, Detection wavelength is 330nm；Column temperature
25 DEG C, flow velocity is 1.0mL/min；Mobile phase A：Mobile phase B=15:85.Wherein the retention time of naringin is 5.1min, quercitrin
The retention time of element is 9.3min, and the retention time of Nobiletin is 14.4min.
The preparation of the Exocarpium Citri Grandis extract of embodiment 2
(1) Exocarpium Citri Grandis is taken, with the ethanol water heating and refluxing extraction 1.5h that volume fraction is 95%, concentrated extracting solution is obtained
Exocarpium Citri Grandis ethanol extract；
(2) Exocarpium Citri Grandis ethanol extract is dissolved in water into suspension, first with isometric petroleum ether extraction, repeats to extract
3 times, petroleum ether extract is discarded, then is extracted with isometric ethyl acetate, extraction 3 times is repeated, merges concentration ethyl acetate extraction
Thing is taken to obtain Exocarpium Citri Grandis extract；
(3) Exocarpium Citri Grandis extract is produced into Exocarpium Citri Grandis extract through silica gel column chromatography is active constituent-enriched；
The active constituent-enriched method of the silica gel column chromatography is：By (the institute in silicagel column of silicagel column on Exocarpium Citri Grandis extract
With 30 times that the weight of silica gel is Exocarpium Citri Grandis extract dry weight, the specification of silica gel is 200 mesh), it is first 85 with volume ratio:15 it is molten
Agent A：The mixed solvent system (consumption is 3 times of column volumes) of solvent B compositions carries out elution removal of impurities；Then volume ratio is used to be 75 again:
25 solvent orange 2 A：The mixed solvent system (consumption is 8 times of column volumes) of solvent B compositions is eluted and collects elution position, is produced
Exocarpium Citri Grandis active component；Described solvent orange 2 A is petroleum ether, and solvent B is ethyl acetate.
After testing, in the Exocarpium Citri Grandis extract containing percentage by weight for 26% Nobiletin, 16% Quercetin
And 34% naringin.
The preparation of the Exocarpium Citri Grandis extract of embodiment 3
(1) Exocarpium Citri Grandis is taken, with the ethanol water heating and refluxing extraction 1.5h that volume fraction is 95%, concentrated extracting solution is obtained
Exocarpium Citri Grandis ethanol extract；
(2) Exocarpium Citri Grandis ethanol extract is dissolved in water into suspension, first with isometric petroleum ether extraction, repeats to extract
3 times, petroleum ether extract is discarded, then is extracted with isometric ethyl acetate, extraction 3 times is repeated, merges concentration ethyl acetate extraction
Thing is taken to obtain Exocarpium Citri Grandis extract；
(3) Exocarpium Citri Grandis extract is produced into Exocarpium Citri Grandis extract through silica gel column chromatography is active constituent-enriched；
The active constituent-enriched method of the silica gel column chromatography is：By (the institute in silicagel column of silicagel column on Exocarpium Citri Grandis extract
With 30 times that the weight of silica gel is Exocarpium Citri Grandis extract dry weight, the specification of silica gel is 200 mesh), it is first 85 with volume ratio:15 it is molten
Agent A：The mixed solvent system (consumption is 3 times of column volumes) of solvent B compositions carries out elution removal of impurities；Then volume ratio is used to be 72 again:
28 solvent orange 2 A：The mixed solvent system (consumption is 8 times of column volumes) of solvent B compositions is eluted and collects elution position, is produced
Exocarpium Citri Grandis active component；Described solvent orange 2 A is petroleum ether, and solvent B is ethyl acetate.
After testing, in the Exocarpium Citri Grandis extract containing percentage by weight for 23% Nobiletin, 12% Quercetin
And 31% naringin.
The extract of embodiment 4 suppresses APE1 expression experiments
Build plasmid pcDNA3.0-APE1 and transfect human lung cancer cell A549, then put human lung cancer cell A549 respectively
Extracted in containing Exocarpium Citri Grandis described in Exocarpium Citri Grandis extract described in Exocarpium Citri Grandis extract described in embodiment 1, embodiment 2, embodiment 3
(composition is 3 by weight ratio for thing, pharmaceutical composition:2:3 Nobiletin, Quercetin and naringin composition) and without appointing
48h is cultivated in the cell culture fluid of what medicine, the expression of APE1 albumen in Western blotting detection cells is then utilized
Situation.Specific method is referring to " the quick .APE1 of Zhang Zhi acts on GAP-associated protein GAP and its Effect study [D] in tumour radiotherapy the
Three army medical universities, 2011. ".
Test result indicates that, cultivated in the cell culture fluid containing Exocarpium Citri Grandis extract of the present invention and pharmaceutical composition
Human lung cancer cell A549 in APE1 protein contents considerably less than the people's lung cultivated in the cell culture fluid without any medicine
Cancer cell A549.This explanation：Exocarpium Citri Grandis extract of the present invention and it is made up of Nobiletin, Quercetin and naringin
Pharmaceutical composition can significantly inhibit the expression of the APE1 in lung carcinoma cell, can be used as APE1 inhibitor, being capable of conduct
The medicine of the disease for the treatment of APE1 mediations is used.
The extract anti-lung cancer activity of embodiment 5 is tested
Human lung cancer cell A549 is taken to be placed in culture in culture medium (culture mediums of RPMI 1640), cancer cell is with 10 × 103Per hole
Add in 96 orifice plates, contain 5%CO at 37 DEG C2Incubator in culture 24 hours after it is adherent after suck original culture medium.Then
Blank group adds the culture mediums of RPMI 1640 containing 10% hyclone；Experimental group is separately added into containing 0.01~100 μ g/mL
The culture mediums of RPMI 1640 of medicine to be measured；Continue to cultivate after 48h, add concentration 5mg/mL MTT, continue to cultivate 4h, suck
Supernatant, adds 100 μ L DMSO, and dark place places 10min, extinction is determined under 570nm using ELIASA (Sunrise companies)
Value, and cell survival is calculated according to light absorption value, each processing sets 6 repeating holes.Cell survival rate (%)=Δ
ODDrug-treated group/ΔODBlank group×100.Cell 503nhibiting concentration (IC is calculated further according to dose-effect curve50), it the results are shown in Table 1.Experiment
The medicine difference of group is as follows：Experimental group 1 uses exclusive use Nobiletin；Quercetin is used alone in experimental group 2；Experimental group 3 is single
Solely use naringin；Experimental group 4 is 3 by weight using Nobiletin, Quercetin and naringin:2:The composition of 4 compositions
1；Experimental group 5 is 3 by weight using hesperetin, Quercetin and naringin:1:The composition 2 of 3 compositions；Experimental group 6 is used
Hesperetin, Quercetin and naringin are 2 by weight:1:The composition 2 of 3 compositions；Experimental group 7 is prepared into using embodiment 1
The Exocarpium Citri Grandis extract arrived；The Exocarpium Citri Grandis extract that experimental group 8 is prepared using embodiment 2；Experimental group 9 uses embodiment 3
The Exocarpium Citri Grandis extract prepared.
IC of the medicine of table 1. to human lung cancer cell A54950Test result
From the experimental group 1~6 in table 1 as can be seen that Nobiletin, Quercetin and naringin are used alone with certain
Anti-lung cancer effect, when Nobiletin, Quercetin and naringin three are mixed in ratio of the present invention, its anti-lung cancer
Effect is more notable, and collaboration effect of anti-lung cancer can be produced after this explanation Nobiletin, Quercetin and naringin three mixing.Cause
This, Nobiletin, Quercetin and naringin three combination can be used as anti-lung-cancer medicament.
From the experimental group 7~9 in table 1 as can be seen that Exocarpium Citri Grandis extract of the present invention has the anti-of highly significant
Lung cancer is acted on, and its effect of anti-lung cancer is better than the effect of anti-lung cancer of any of which monomer, and this is due to therein effective
Composition Nobiletin, Quercetin and naringin produce the effect of collaboration anti-lung cancer.
Claims (10)
1. a kind of Exocarpium Citri Grandis extract, it is characterised in that include following active ingredient：Nobiletin, Quercetin and naringin.
2. Exocarpium Citri Grandis extract according to claim 1, it is characterised in that comprising following percentage by weight it is effective into
Point：Nobiletin 20~30%；Quercetin 10~20%；Naringin 30~40%.
3. the preparation method of the Exocarpium Citri Grandis extract described in claim 1 or 2, it is characterised in that comprise the following steps：
(1) Exocarpium Citri Grandis is taken, ethanol heating and refluxing extraction is used, concentrated extracting solution obtains Exocarpium Citri Grandis ethanol extract；
(2) Exocarpium Citri Grandis ethanol extract is dissolved in water into suspension, first with petroleum ether extraction, discards petroleum ether extract, then
It is extracted with ethyl acetate, concentration acetic acid ethyl ester extract obtains Exocarpium Citri Grandis extract；
(3) Exocarpium Citri Grandis extract is produced into Exocarpium Citri Grandis extract through silica gel column chromatography is active constituent-enriched；
The active constituent-enriched specific method of silica gel column chromatography is in step (3)：By silicagel column on Exocarpium Citri Grandis extract, body is first used
Product is than being 85:15~80:The mixed solvent system of 20 solvent orange 2 A and solvent B composition carries out elution removal of impurities；Then volume ratio is used again
For 75:25~72:The mixed solvent system of 28 solvent orange 2 A and solvent B composition is eluted and collects elution position, producing tangerine
Red active component；Described solvent orange 2 A is petroleum ether, and solvent B is ethyl acetate；
Volume ratio is 85:15~80:The consumption of the mixed solvent system of 20 solvent orange 2 A and solvent B composition is silicagel column column volume
1~3 times；Volume ratio is 75:25~72:The consumption of the mixed solvent system of 28 solvent orange 2 A and solvent B composition is silicagel column post
3~5 times of volume.
4. preparation method according to claim 3, it is characterised in that silica gel column chromatography is active constituent-enriched in step (3)
Specific method be：It is first 80 with volume ratio by silicagel column on Exocarpium Citri Grandis extract:20 solvent orange 2 A：The mixing of solvent B compositions
Dicyandiamide solution carries out elution removal of impurities；Then volume ratio is used to be 72 again:28 solvent orange 2 A：The mixed solvent system of solvent B compositions is carried out
Elute and collect elution position, produce Exocarpium Citri Grandis active component；
Volume ratio is 80:The consumption of the mixed solvent system of 20 solvent orange 2 A and solvent B composition is 3 times of silicagel column column volume；Body
Product is than being 72:The consumption of the mixed solvent system of 28 solvent orange 2 A and solvent B composition is 5 times of silicagel column column volume.
5. preparation method according to claim 3, it is characterised in that the weight of used silica gel is in step (3) silicagel column
20~40 times of Exocarpium Citri Grandis extract dry weight.
6. preparation method according to claim 3, it is characterised in that the ethanol described in step (1) is that volume fraction is
80~100% ethanol water；The consumption of described ethanol and the amount ratio of Exocarpium Citri Grandis are 8~15mL:1g；Described heating
The time of refluxing extraction is 1~3h；First oil is discarded in step (2) with the petroleum ether extraction isometric with suspension 1~3 time
Ether extract, then extracted 1~3 time with the isometric ethyl acetate of suspension, concentration acetic acid ethyl ester extract obtains Exocarpium Citri Grandis extraction
Take thing.
7. application of the Exocarpium Citri Grandis extract in APE1 inhibitor is prepared described in claim 1 or 2.
8. application of the Exocarpium Citri Grandis extract in the medicine of disease for the treatment of APE1 mediations is prepared described in claim 1 or 2；Institute
The disease for stating APE1 mediations is the lung cancer that APE1 is mediated.
9. application of the Exocarpium Citri Grandis extract described in claim 1 or 2 in cancer therapy drug is prepared, described cancer therapy drug is anti-
Lung-cancer medicament.
10. a kind of anticancer pharmaceutical composition from Exocarpium Citri Grandis, it is characterised in that include Nobiletin, Quercetin and shaddock
Skin glucoside, the weight ratio of described Nobiletin, Quercetin and naringin is 2~3：1~2：3~4；Described cancer therapy drug is
Anti-lung-cancer medicament.
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