CN103588783B - Table Resina garciniae alkyd and preparation method thereof and in application pharmaceutically - Google Patents
Table Resina garciniae alkyd and preparation method thereof and in application pharmaceutically Download PDFInfo
- Publication number
- CN103588783B CN103588783B CN201310294149.0A CN201310294149A CN103588783B CN 103588783 B CN103588783 B CN 103588783B CN 201310294149 A CN201310294149 A CN 201310294149A CN 103588783 B CN103588783 B CN 103588783B
- Authority
- CN
- China
- Prior art keywords
- alkyd
- resina garciniae
- acid
- preparation
- cell
- 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.)
- Expired - Fee Related
Links
- QSLJXTJWTKLAHB-LKGJPQIOSA-N CC(C)([C@@H](CC1)[C@H]2c(c(O)c(c(O[C@]3([C@@]4(C/C=C(/C)\C(O)=O)OC(C)(C)[C@@H]3C3)C5=C[C@H]3C4=O)c3CC=C(C)C)C5=O)c3O[C@]1(C)C2)O Chemical compound CC(C)([C@@H](CC1)[C@H]2c(c(O)c(c(O[C@]3([C@@]4(C/C=C(/C)\C(O)=O)OC(C)(C)[C@@H]3C3)C5=C[C@H]3C4=O)c3CC=C(C)C)C5=O)c3O[C@]1(C)C2)O QSLJXTJWTKLAHB-LKGJPQIOSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/20—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to a kind of cage poly-isopentene xanthones compound epigambogic alcohol acid, it has anti-tumor activity.The invention still further relates to the preparation method of table Resina garciniae alkyd: with gamlogic acid as raw material, heating, preparative liquid chromatography separates and get final product.The invention still further relates to the application in preparing antitumor drug of the table Resina garciniae alkyd.
Description
Technical field
The present invention relates to a kind of cage poly-isopentene xanthones compound and preparation method thereof and pharmaceutically
Application.
Background technology
Along with the impact of the factors such as living standard raising, increasing environmental pollution, the sickness rate of malignant tumor is the most year by year
Soaring.Existing antitumor drug kind is limited, and toxic and side effects is big, can not meet the most far away the medication demand of clinic.
Resina garciniae is the trunk of Guttiferae (Guttifera) plant gamboge tree (Garcinia hanburyi Hook F.G.)
The colloidal resin gone out secreted by after hurting.In reddish yellow or orange red, main product Cambodia, Thailand and Vietnam, Guangdong Province of China
Cultivation is had with Hainan Province.Resina garciniae is resin 70%-80%, the mixture of natural gum 15%-25% etc..Wherein containing gamlogic acid
(gambogic acid) 22.75%-36.59%, neogambogic acid (neogambogic acid), allogambogic acid
Compositions such as (allogambogic acid).The traditional Chinese medical science is used for counteracting toxic substances, detumescence, putrefaction removing sore, hemostasis, parasite killing.Cure mainly swollen ulcer drug,
Ulcer, eczema, tumor, stubborn dermatitis, traumatic injury, wound hemorrhage and scald.The external diuretic that is used as, when treatment edema and cerebral hemorrhage
Blood pressure lowering etc., record in American Pharmacopeia the tenth edition.Over nearly more than 20 years, Resina garciniae and activity thereof are become by the most particularly Chinese scholar
Gamlogic acid etc. is divided to do substantial amounts of research work.Resina garciniae and gamlogic acid etc. are used for treating tumor efficiency significantly, and toxic and side effects is little, lives
Property constitutive property stable, caused extensive concern.
Health product Resina garciniae is very toxic, and severe patient is acutely suffered from diarrhoea, suffered from abdominal pain, and is even dehydrated, suffers a shock, therefore typically can not take orally, mainly
It is external curing swollen ulcer drug, stubborn dermatitis.Health product Resina garciniae, after concocting, not only ensures the cleanliness of medicine, and after making, toxicity reduces,
Being available for taking orally, for traumatic injury, incised wound toxic swelling, tumor, such as multitude's cave ball.
Resina garciniae medication starts from the Tang Dynasty, and its process of preparing Chinese medicine starts from the Qing Dynasty, and traditional concocting method of Resina garciniae mainly has clear water system (to be loaded in
Supplementary Amplifications of the Compendium of Materia Medica), Folium Nelumbinis system (being loaded in Golden Mirror of Medicine), bean curd system and Sanguis Naemorhedi system (are loaded in that " surgery card is controlled complete raw
Collection ").The modern process of preparing Chinese medicine to Resina garciniae is mainly intended to two kinds of methods: clear water system and high pressure steaming, has adjuvant and is easy to get, operation
The features such as convenience.
The structural formula of gamlogic acid (Gambogic acid) is as follows:
In prior art, table Resina garciniae olefin(e) acid (epigambogellic acid) is known compound, and its structural formula is as follows:
Research shows, human hepatocellular carcinoma SMMC-7721 cell strain and QGY-7701 cell strain are had substantially by gamlogic acid
Inhibited proliferation, and in dose dependent, and relatively weak to normal person's hepatic tissue L-02 cell strain effect.The master of gamlogic acid
Wanting toxicity is liver function injury, pain.
In sum, in view of in prior art, tumor kind is limited and toxic and side effects big, invention is safely and effectively
Noval chemical compound the most necessary.
Summary of the invention
One of the technical problem to be solved is to provide a kind of compound with anti-tumor activity.
Another technical problem to be solved by this invention is to provide a kind of method preparing above-claimed cpd.
The technical problem of present invention technology to be solved also resides in above-claimed cpd and can be used for preparing antitumor drug.
In order to solve above-mentioned technical problem, the present invention proposes following technical proposal:
The table Resina garciniae alkyd (Epigambogollic acid) that following formula represents, its structural formula is:
The preparation method of described table Resina garciniae alkyd, it is characterised in that described method is made up of the following step:
(1) taking gamlogic acid, add the water of its quality 80-120 times amount, oil bath is heated to reflux 24-60h, and concentrating under reduced pressure is evaporated,
Obtain residue；
(2) liquid phase separation is prepared:
Chromatographic condition is as follows: be 10 μm with specification, and the μ Bondapark C18 post of 19mm × 300mm is chromatographic column；With body
Long-pending is flowing phase than methanol-1% glacial acetic acid being 85: 15, and flow velocity is 16mL/min, and detection wavelength is 360nm, and column temperature is 30
℃；
Step gained residue before taking, with flowing phased soln, filters, injects preparative liquid chromatograph, collects appearance time and is
Fraction between 14-16min, merges, is evaporated to do, to obtain final product.
The application in preparing antitumor drug of the described table Resina garciniae alkyd.
The preparation of table Resina garciniae alkyd and the data of structure elucidation are shown in test one.
Test one, the preparation of table Resina garciniae alkyd and structure elucidation.
1 preparation method: prepare by embodiment 3.
2 Structural Identification data are as follows:
The spectral data of 2.1 reference compounds table Resina garciniae olefin(e) acid (epigambogellic acid)
Table Resina garciniae olefin(e) acid (epigambogellic acid) is dissolved in deuterochloroform, with TMS as internal standard, detects, its
NMR data is shown in Table 1:
The nuclear-magnetism related data of table 1 table Resina garciniae olefin(e) acid
The Structural Identification of 2.2 table Resina garciniae alkyd
2.2.1UV identify
Take appropriate compound, with methanol as solvent, make the solution that concentration is 0.01mg/mL, (25 DEG C) detection under room temperature,
The absorption spectrum of ultraviolet is shown in Figure of description 1, and obtained the maximum absorption is at 215nm, 360nm, compared with gamlogic acid, has lacked 280nm
The uv absorption at place.
2.2.2MS identify
Take appropriate compound, with methanol as solvent, make the solution that concentration is 0.01mg/mL, with methanol-1% acetic acid be
Flowing phase, wriggling sample introduction 5 μ L.Result is shown in Figure of description 2, and high resolution mass spectrum provides compound [M+H]+Quasi-molecular ion peak
M/z647.3228, determines that the molecular formula of this compound is C38H46O9, m/z629 is its [M-H2O]+Peak, m/z573 is its [M-
H2O-C4H7]+Peak, m/z679 is its [M+Na]+Peak.
2.2.3NMR identify
Compound being dissolved in deuterochloroform, with TMS as internal standard, detects, result is shown in Figure of description 3-8.Compound
NMR data be shown in Table 2:
The nuclear-magnetism related data of table 2 table Resina garciniae alkyd
2.2.4 the structure elucidation of compound
Yellow oily compound, is soluble in chloroform, and after 10% ethanol solution of sulfuric acid colour developing, yellow is deepened, and prompting may be
Xanthone compounds.1In H-NMR spectrum, be given one with the hydroxyl proton signal δ 13.93 of carbonyl association (1H, s), two
Alkene Hydrogen Proton signal on typical isopentene group, δ 4.98 and δ 6.25 (each, 1H, m), it addition, visible 8 methyl singlets matter
Subsignal, lay respectively at δ 1.14, δ 1.26, δ 1.36, δ 1.56, δ 1.63, δ 1.69, δ 1.72 and δ 1.72 (each, 3H, s).13In C-NMR spectrum, providing 38 carbon signals altogether, wherein, δ c203.7 is ketone carbonyl signals, and δ c179.0 is beta-unsaturated ketone carbonyl letter
Number, δ c167.8 is carboxyl signal.1In H-NMR spectrum, 63.46 (1H, dd, J=4.5,6.9Hz, H-11), δ 2.29 (1H, dd, J
=4.5,9.2Hz, Ha-21) and δ 2.49 (1H, d, J=9.2Hz, Ha-22) be on dicyclo [2,2,2] octane diagnostic protons letter
Number.Three occurred in composing in conjunction with carbon even oxygen carbon signal δ c91.1, δ c84.3, δ c83.9, can speculate that this compound is a caged
Many isopentene groups xanthones compounds.Compared with known compound table Resina garciniae olefin(e) acid (epigambogellic acid),
Many methyl singlets proton signals, have lacked terminal double bond proton signal, it is judged that the double bond for C-38, C-40 position is sent out with water
Raw additive reaction.Meanwhile, in its ROESY spectrum, have not seen the locus coherent signal of H-37 Yu H-19, prompting 19-methyl and
37-H is at the heteropleural of hexatomic ring.Through retrieval, compound is a noval chemical compound having no that document is reported, named table Resina garciniae alkyd
epigambogollic acid.Its structural formula is shown in Figure of description 9.
Table Resina garciniae alkyd antineoplastic pharmacologically active can be embodied by following test.
Test example two table Resina garciniae alkyd is to Hepatocellular carcinoma cell line, the inhibitory action research of Human normal hepatocyte L-02
1 experiment material
1.1 medicine
Table Resina garciniae alkyd, is prepared by embodiment 3.Gamlogic acid, self-control.
1.2 main agents, consumptive material
New-born calf serum (FBS): Hangzhou Sijiqing Biological Engineering Material Co., Ltd.；
RPMI Medium1640 culture medium: GIBCOTMInvitrogen Corporation, Cat.No.31800-
014.Lot No.1279327；
Costar96 orifice plate, Tissue Culture Flask, Corning company of the U.S.；
Dimethyl sulfoxide (DMSO), Biosharp company, Lot:2010/10；
Tetrazolium bromide (MTT): Biosharp, Lot:2010/08；
NaCl: Shantou Xilong Chemical Factory Co., Ltd, analytical pure, lot number: 080916；
KCl: Nanjing chemical reagent factory, analytical pure, lot number: 830602；
KH2PO4: Shanghai reagent two factory, analytical pure；Lot number: 950215；
Na2HPO4-12H2O: Shanghai Ling Feng chemical reagent company limited, analytical pure；Lot number: 080102；
Water is ultra-pure water, and other reagent is analytical pure.
1.3 key instrument
Microplate reader: Power Wave X340, BIO-TEK INTRUMENTS, Inc
Superclean bench: cleaning equipment company limited of Suzhou City；
LDZ5-2 low speed autobalancing centrifuge: Beijing Medical Centrifugal Machine Factory；
Serious II water jacketed CO2Incubator:Thermo Electron Corporation；
Olympus CKX31 microscope
Electronic balance: FA2004N upper Nereid section (ten thousand/), Sartorius BT125D (100,000/)
Portable pressure steam sterilizing device YXQ.SG41.280, Shanghai Huaxian Medical Nuclear Instruments Co., Ltd.
1.4 cell strain
Human liver cancer cells Hep G2, people normal cell lines of human liver L-02, is concocted research emphasis laboratory and clinic by Jiangsu Province
Pharmacological evaluation room provides.
2 methods and result
The preparation of 2.1 main agents
2.1.1PBS the preparation of solution
Precision weighs NaCl4g, KCl0.1g, Na2HPO41.74g, KH2PO40.1g, adds ultra-pure water 500mL, continuous stirring
15min is to being completely dissolved.
2.1.2RPMI1640 culture medium
Take RPMI Medium1640 culture medium powder, separately add NaHCO31.70g, adds ultra-pure water 1000mL, continuous stirring
30min is to being completely dissolved.
2.1.3 the preparation of trypsin solution
Precision weighs trypsin 0.25g, adds PBS solution 100mL, mixing.
Above-mentioned solution, in super-clean bench, with aseptic injection filter (the 0.22 aseptic microporous filter membrane of μm) filtration sterilization, is distributed into
Bottle, 4 DEG C save backup.
2.1.4MTT the preparation of liquid
Weighing MTT powder, add appropriate PBS solution, vortex dissolves, and makes into the solution that concentration is 5mg/mL.
The configuration of 2.2 test liquids
2.2.1 the preparation of sample solution
Accurate Weigh Compound table Resina garciniae alkyd 1.08mg, gamlogic acid 1.14mg, add appropriate DMSO respectively, ultrasonic to complete
CL.
Before administration, it is diluted to 0.25 μm ol/L, 0.5 μm ol/L, 1 μm ol/L, 2 μm ol/L, 4 μ by RPMI1640 culture medium
Mol/L, 8 μm ol/L, a series of concentration such as 16 μm ol/L, 4 DEG C save backup.
2.2.2 Western medicine positive drug solution
Take the mother solution (1mg/mL) of DDP (trade name: cisplatin), before being administered, be diluted to 2 μ g/mL by RPMI1640 culture medium.
2.2.3 the preparation of blank group solution
Draw the DMSO of certain volume, be diluted to the concentration needed by RPMI1640 culture medium, the highest be less than 5 ‰.
3 Related Components are to Normocellular toxicity test
The cultivation of 3.1 normal cell lines of human liver L-02
Normal cell lines of human liver L-02 cellar culture is in the RPMI1640 culture medium containing 15% calf serum.Be placed in 37 DEG C, 5%
CO2Cultivate in incubator, cultivate to 70%-80% merge time, 0.25% trypsinization, pass on, maintain suitable cell
Concentration.
3.2MTT method measures cell proliferation inhibition rate
Take the logarithm the normal cell lines of human liver L-02 of trophophase, PBS 2-3 time, adds 0.25% trypsin solution digestion, treats cell
Retraction, becomes round, and incline pancreatin in time, adds the RPMI1640 culture medium containing 15% calf serum, on piping and druming bottle wall in cell bottle
Cell, make cell be dispersed in culture medium.Drawing a small amount of cell suspension, in counted under microscope, regulation cell concentration is 5
×104/mL.It is inoculated in 96 porocyte culture plates, every hole 100 μ L.After cell attachment after (about 24h), inhale gently and abandon in hole
Medium supernatant, adds RPMI1640 culture medium hunger 24h.Inhale gently and abandon medium supernatant in hole, be separately added into not
With sample solution 200 μ L:0.25 μm ol/L of concentration, 0.5 μm ol/L, 1 μm ol/L, 2 μm ol/L, 4 μm ol/L, 8 μm ol/L, 16
μm ol/L ... each concentration sets 6 multiple holes, and sets the blank group without sample and Western medicine positive drug control group.Cultivate 44h
After, after every hole adds the MTT solution 20 μ L effect 4h of 5mg/mL, to inhale gently and abandon culture supernatant in hole, it is molten that every hole adds DMSO
Liquid 150 μ L shakes 10min gently, makes crystal fully dissolve, withered with blank well.At enzyme-linked immunosorbent assay instrument 490nm wavelength
Place measures each hole optical density value (OD value), seeks its meansigma methods.It is designated as 100% with blank group cellular control unit survival rate.
3.3 experimental result
Calculate by following equation: experimental group cell inhibitory rate %=(1-experimental group OD value/matched group OD value) × 100%,
Do linear regression with drug level (μm ol/L) and suppression ratio (%), calculate this medicine and the half of normal cell lines of human liver L-02 is suppressed dense
Degree IC50。
Table 3 compound IC to normal cell lines of human liver L-0250Result of calculation
The antineoplastic agent effect card of 4 Related Components
The cultivation of 4.1 Hepatocellular carcinoma cell line
Hepatocellular carcinoma cell line cellar culture is in the RPMI1640 culture medium containing 10% calf serum.Be placed in 37 DEG C,
5%CO2Cultivate in incubator, cultivate to 70%-80% merge time, 0.25% trypsinization, pass on, remain suitable thin
Born of the same parents' concentration.
4.2MTT method measures cell proliferation inhibition rate
Take the logarithm the Hepatocellular carcinoma cell line of trophophase, PBS 2-3 time, add 0.25% trypsin solution digestion, treat
Cell bounces back, and becomes round, and incline pancreatin in time, adds the RPMI1640 culture medium containing 10% calf serum in cell bottle, blows and beats bottle
Cell on wall, makes cell be dispersed in culture medium.Drawing a small amount of cell suspension, in counted under microscope, regulation cell is dense
Degree is 5 × 104/mL.It is inoculated in 96 porocyte culture plates, every hole 100 μ L.After cell attachment after (about 24h), inhale gently and abandon
Medium supernatant in hole, adds RPMI1640 culture medium hunger 24h.Inhale gently and abandon medium supernatant in hole, be separately added into
By sample solution 200 μ L:0.25 μm ol/L of variable concentrations, 0.5 μm ol/L, 1 μm ol/L, 2 μm ol/L, 4 μm ol/L, 8 μm ol/
L ... each concentration sets 6 multiple holes, and sets the blank group without sample and Western medicine positive drug control group.After cultivating 44h, often
After hole adds the MTT solution 20 μ L effect 4h of 5mg/mL, inhaling gently and abandon culture supernatant in hole, every hole adds DMSO solution 150 μ
L shakes 10min gently, makes crystal fully dissolve, withered with blank well.Measure at enzyme-linked immunosorbent assay instrument 490nm wavelength
Each hole optical density value (OD value), seeks its meansigma methods.It is designated as 100% with blank group cell survival rate.
4.3 experimental result
Calculate by following equation: experimental group cell inhibitory rate %=(1-experimental group OD value/matched group OD value) × 100%,
Do linear regression with drug level (μm ol/L) and suppression ratio (%), calculate this medicine and the half of Hepatocellular carcinoma cell line is pressed down
Concentration IC processed50。
The IC of table 4 compound on tumor cell SMMC-772150Result of calculation
5 conclusions
If it is single from IC50Analyzing, compound table Resina garciniae alkyd is to the inhibition of Hepatocellular carcinoma cell line and gamlogic acid
Quite, and it is lower than gamlogic acid to the toxicity of normal cell lines of human liver L-02.
Table Resina garciniae alkyd is in time preparing the application in antitumor drug, and its oral or non-oral administration is all safe and effective
's.Oral administration can make any regular dosage form, such as: powder, granule, capsule, sheet, oral cavity disintegration tablet, drop pill, soft capsule etc.；Non-
Oral administration, can be made into various regular dosage form, such as injection etc..
When table Resina garciniae alkyd is used for preparing antitumor drug, its adjuvant and preparation method can be selected for any pharmaceutically acceptable
Form.
The dosage of table Resina garciniae alkyd can change according to taking the factors such as mode, the age of patient, coincident with severity degree of condition, becomes
Human oral dosage form is 1-200mg/ day, and adult injection dosage is 1-50mg/ day.
Accompanying drawing explanation
Below in conjunction with embodiment, the present invention is further illustrated:
The ultra-violet absorption spectrum of Fig. 1 table Resina garciniae alkyd；
The mass spectrum of Fig. 2 table Resina garciniae alkyd；
Fig. 3 table Resina garciniae alkyd1H-NMR spectrum
Fig. 4 table Resina garciniae alkyd13C-NMR collection of illustrative plates
The H-H COSY collection of illustrative plates of Fig. 5 table Resina garciniae alkyd
The HSQC collection of illustrative plates of Fig. 6 table Resina garciniae alkyd
The HMBC collection of illustrative plates of Fig. 7 table Resina garciniae alkyd
The ROESY collection of illustrative plates of Fig. 8 table Resina garciniae alkyd
The structural formula of Fig. 9 table Resina garciniae alkyd
Detailed description of the invention
Following embodiment can better illustrate the present invention, and it limits protection model of the presently claimed invention the most in any form
Enclose.
The preparation of embodiment 1 table Resina garciniae alkyd
(1) taking gamlogic acid 100mg, add the water of its quality 80 times amount, oil bath is heated to reflux 24h, and concentrating under reduced pressure is evaporated, i.e.
Obtain residue；
(2) liquid phase separation is prepared:
Chromatographic condition is as follows: be 10 μm with specification, and the μ Bondapark C18 post of 19mm × 300mm is chromatographic column；With body
Long-pending is flowing phase than methanol-1% glacial acetic acid being 85: 15, and flow velocity is 16mL/min, and detection wavelength is 360nm, and column temperature is 30
℃；
Step gained residue before taking, with flowing phased soln, filters, injects preparative liquid chromatograph, collects appearance time and is
Fraction between 14-16min, merges, is evaporated to do, obtains yellow oily compound 8.6mg, examines through HPLC normalization method
Surveying, purity is 96.7%, and its spectral data is consistent with the content recorded above.
The preparation of embodiment 2 table Resina garciniae alkyd
(1) taking gamlogic acid 100mg, add the water of its quality 120 times amount, oil bath is heated to reflux 60h, and concentrating under reduced pressure is evaporated,
Obtain residue；
(2) liquid phase separation is prepared:
Chromatographic condition is as follows: be 10 μm with specification, and the μ Bondapark C18 post of 19mm × 300mm is chromatographic column；With body
Long-pending is flowing phase than methanol-1% glacial acetic acid being 85: 15, and flow velocity is 16mL/min, and detection wavelength is 360nm, and column temperature is 30
℃；
Step gained residue before taking, with flowing phased soln, filters, injects preparative liquid chromatograph, collects appearance time and is
Fraction between 14-16min, merges, is evaporated to do, obtains yellow oily compound 10.6mg, through HPLC normalization method
Detection, purity is 96.3%, and its spectral data is consistent with the content recorded above.
The preparation of embodiment 3 table Resina garciniae alkyd
(1) taking gamlogic acid 100mg, add the water of its quality 100 times amount, oil bath is heated to reflux 48h, and concentrating under reduced pressure is evaporated,
Obtain residue；
(2) liquid phase separation is prepared:
Chromatographic condition is as follows: be 10 μm with specification, and the μ Bondapark C18 post of 19mm × 300mm is chromatographic column；With body
Long-pending is flowing phase than methanol-1% glacial acetic acid being 85: 15, and flow velocity is 16mL/min, and detection wavelength is 360nm, and column temperature is 30
℃；
Step gained residue before taking, with flowing phased soln, filters, injects preparative liquid chromatograph, collects appearance time and is
Fraction between 14-16min, merge, concentrating under reduced pressure as, obtain yellow oily compound 10.2mg, through HPLC normalization method
Detection, purity is 96.4%.
The preparation of embodiment 4 table Resina garciniae alkyd sheet
Tablet: table Resina garciniae alkyd 20mg, starch 180g, pelletizes, and tabletting makes 1000.Instructions of taking: be grown up one time 1
Sheet, 3 times on the one.
Claims (1)
1. the preparation method of a table Resina garciniae alkyd, it is characterised in that described method is made up of the following step:
(1) taking gamlogic acid, add the water of its quality 80-120 times amount, oil bath is heated to reflux 24-60h, and concentrating under reduced pressure is evaporated, and to obtain final product
Residue；
(2) liquid phase separation is prepared:
Chromatographic condition is as follows: be 10 μm with specification, and the μ Bondapark C18 post of 19mm × 300mm is chromatographic column；With volume ratio
Be 85: 15 methanol-1% glacial acetic acid for flowing phase, flow velocity is 16mL/min, and detection wavelength is 360nm, and column temperature is 30 DEG C；
Step gained residue before taking, with flowing phased soln, filters, injects preparative liquid chromatograph, and collection appearance time is 14-
Fraction between 16min, merges, is evaporated to do, to obtain final product；
The structural formula of described table Resina garciniae alkyd is as follows:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310294149.0A CN103588783B (en) | 2013-07-15 | 2013-07-15 | Table Resina garciniae alkyd and preparation method thereof and in application pharmaceutically |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310294149.0A CN103588783B (en) | 2013-07-15 | 2013-07-15 | Table Resina garciniae alkyd and preparation method thereof and in application pharmaceutically |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103588783A CN103588783A (en) | 2014-02-19 |
| CN103588783B true CN103588783B (en) | 2016-08-10 |
Family
ID=50079135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310294149.0A Expired - Fee Related CN103588783B (en) | 2013-07-15 | 2013-07-15 | Table Resina garciniae alkyd and preparation method thereof and in application pharmaceutically |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103588783B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1563014A (en) * | 2004-04-16 | 2005-01-12 | 杭州民生药业集团有限公司 | New compound ramification of garcinia acid |
| CN102276621A (en) * | 2010-06-11 | 2011-12-14 | 台湾森本生物科技开发股份有限公司 | Compound separated from gamboge resin and derivative thereof and pharmaceutical composition comprising compound and derivative |
-
2013
- 2013-07-15 CN CN201310294149.0A patent/CN103588783B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1563014A (en) * | 2004-04-16 | 2005-01-12 | 杭州民生药业集团有限公司 | New compound ramification of garcinia acid |
| CN102276621A (en) * | 2010-06-11 | 2011-12-14 | 台湾森本生物科技开发股份有限公司 | Compound separated from gamboge resin and derivative thereof and pharmaceutical composition comprising compound and derivative |
Non-Patent Citations (2)
| Title |
|---|
| 藤黄科植物中具有桥环结构的天然产物全合成研究进展;林昌军等;《有机化学》;20081231;第28卷(第2期);218-277 * |
| 藤黄酸及其类似物抗肿瘤的定量构效关系;冯锋等;《中国医科大学学报》;20071231;第38卷(第4期);第312、314页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103588783A (en) | 2014-02-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wong et al. | Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity | |
| WO2005037200A2 (en) | Composition comprising xanthoceras sorbifolia extracts, compounds isolated from same, methods for preparing same and uses thereof | |
| Pan et al. | Daphnane diterpenoids from Daphne genkwa inhibit PI3K/Akt/mTOR signaling and induce cell cycle arrest and apoptosis in human colon cancer cells | |
| CN107488204A (en) | Dammarane type ginsenoside（Member）And its antiphlogistic use of ocotillol type derivatives | |
| Yan et al. | Neuroprotective effects of rutaecarpine on cerebral ischemia reperfusion injury | |
| CN103880910A (en) | Preparation method and application of cycloastragenol | |
| Lu et al. | Chronic toxicity of ginsenoside Re on Sprague-Dawley rats | |
| Huang et al. | Cucurbitane-type triterpenoids from the vines of Momordica charantia and their anti-inflammatory activities | |
| Du et al. | Oxypeucedanin relieves LPS-induced acute lung injury by inhibiting the inflammation and maintaining the integrity of the lung air-blood barrier | |
| CN103588782B (en) | Resina garciniae alkyd and preparation method thereof and in application pharmaceutically | |
| CN101732440B (en) | Raspberry extract and raspberry element obtain by separation thereof and application thereof | |
| CN103588783B (en) | Table Resina garciniae alkyd and preparation method thereof and in application pharmaceutically | |
| Yu et al. | Resveratrol improves urinary dysfunction in rats with chronic prostatitis and suppresses the activity of the stem cell factor/c-Kit signaling pathway | |
| CN106496245A (en) | The pharmaceutical composition of lisinopril and its application in biological medicine | |
| Chen et al. | Fraction of macroporous resin from Smilax china L. inhibits testosterone propionate–induced prostatic hyperplasia in castrated rats | |
| CN114748516A (en) | Application of Coptis japonica root in preparing medicament for treating osteoarthritis | |
| CN105560308B (en) | Flower of JINHUAKUI is preparing the application in the product for preventing and treating prostatic disorders | |
| CN104693121B (en) | One class has pyrazole compound, preparation method and the application of anti-senile dementia activity | |
| CN104274437B (en) | A kind of medicinal usage of A type trimerization OPC class polyphenol | |
| CN102626407A (en) | Application of isodaphnetin compound in preparation of antidiabetic medicines | |
| CN101665489A (en) | Dehydrosilybin trialky ether and preparation method and medical application thereof | |
| CN105732736B (en) | A kind of preparation method of phenylpropanoids | |
| Xiong et al. | A detailed overview of quercetin: implications for cell death and liver fibrosis mechanisms | |
| CN105708845B (en) | A kind of application of phenylpropanoids and its pharmaceutically acceptable salt in the drug for preparing treatment diseases associated with inflammation | |
| CN105884841B (en) | A kind of preparation method of phenylpropanoids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160810 Termination date: 20170715 |