CN108272790A - A kind of medicinal usage of xanthones compound A - Google Patents
A kind of medicinal usage of xanthones compound A Download PDFInfo
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- CN108272790A CN108272790A CN201810046218.9A CN201810046218A CN108272790A CN 108272790 A CN108272790 A CN 108272790A CN 201810046218 A CN201810046218 A CN 201810046218A CN 108272790 A CN108272790 A CN 108272790A
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- 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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- 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
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07B2200/07—Optical isomers
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Abstract
The invention discloses a kind of medicinal usage of xanthones compound A, the xanthones compound A has chemical constitution shown in Formulas I：
Description
Technical field
The present invention relates to a kind of medicinal usages of xanthones compound A, belong to pharmaceutical technology field.
Background technology
Malignant tumour is one of main fatal disease in the world, seriously threatens human health and life.Middle traditional Chinese medical science
Tumour hospital of subject institute, National Cancer Center He Jie academician, national tumour Register director professor Chen Wanqing are equal in CA:A
The Cancer in China statistical data in 2015 delivered on Cancer Journal for Clinicians magazines showed in 2015
There are about 429.2 ten thousand new tumor cases and 281.4 ten thousand deaths for state.The aggravation of problem with the aging of population, China
The incidence of cancer is in rising trend, causes great burden, cancer control to have become existing China's health resources and national economy
The emphasis of modern China's health strategy.National science and technology key special subjects " great new drug initiative " project is classified as clinic, and there is an urgent need for drugs to grind
One of 10 classes (kind) major disease of hair.
The therapy of tumour includes surgical operation and chemicotherapy.The outstanding problem of the antitumor drug of Present clinical application
It is efficient low, poor selectivity (toxicity is big) and to the insensitive of resistant tumors.In addition, recurrence and transfer are also oncotherapy
Difficult point.Therefore, research selectivity is good, and curative effect is high, and target spot is clear, and the antitumor drug without side-effects to non-target organ is pharmacy
The great research topic of worker.
Natural products for new drug discovery and design, synthesis has very important significance and bioactive substance
With the important sources of original new drug.According to the literature：Since 1940, the anticancer chemotherapeutic agent of sale available worldwide
In, 42% is to be derived directly from natural products, such as：Taxol (Taxol), Xi Tasai (Docetaxel), vinorelbine
(Vinorelbine), Hydroxycamptothecin (camptothecin), qinghaosu (Artemisinin) etc., 30% is spreading out for natural products
Biology or its analog.Natural products is advantageous in that as medicament sources exploitation：The natural products small molecule of source of students synthesis
SMNPs has the biocompatibility (biocompatibility) being preferably combined with enzyme and receptor, it is easier to or be suitble into
For the lead compound of medicine.The traditional Chinese medicine and pharmacy in China is of long standing and well established, of extensive knowledge and profound scholarship, be traditional Chinese culture representative with
The rarity of traditional culture.Therefore, lead compound with anti-tumor activity is found from traditional Chinese medicine and medicinal plant, is studied
Its mechanism of action, to develop the hot spot that antineoplaston drug is current research.
Big bud gamboge (Garcinia bracteata) is the plant of Guttiferae Garcinia, is distributed mainly on China's cloud at present
South-South portion to the southeast and south Guangxi, it is domestic at present that the chemical composition of big luxuriant gamboge and the research of pharmacological action are reported both at home and abroad
Road is few.
Invention content
In view of the above-mentioned problems existing in the prior art, the object of the present invention is to provide one kind is detached by big luxuriant gamboge extraction
Medicinal usages of the xanthones compound A arrived in anti-tumor aspect.
Xanthones compound A of the present invention has chemical constitution shown in Formulas I：Chemical name
For：12R-isobractatin；The medicinal usage refers to the xanthones compound A or its hydrate, pharmacy
At least one of upper acceptable salt, tautomer, stereoisomer, precursor compound are used to prepare as active constituent
Antitumor drug.
Preferably, the antitumor drug is to treat appointing in cervix cancer, prostate cancer, adenocarcinoma of lung, intestinal cancer
The drug of the one or more kinds of tumours of meaning.
The xanthones compound A can be extracted by chemical synthesis or from plant and be obtained；Preferably, institute
The xanthones compound A stated be extracted from big luxuriant gamboge it is isolated.
A kind of embodiment, the method from the big luxuriant gamboge extraction separation xanthones compound A include following step
Suddenly：
A) big luxuriant gamboge leaf is extracted substantially colorless to percolate with 95wt% ethanol percolations, percolate is concentrated under reduced pressure, obtains
Extract；
B) extract obtained by step a) is suspended in water, with petroleum ether extraction, obtains the stone of big luxuriant Resina garciniae extract
Oily ether extracts position；
C) by the petroleum ether extraction position of big luxuriant Resina garciniae extract obtained by step b) by silica gel post separation, with petroleum ether and
Ethyl acetate is according to 100：0~20：Gradient elution, every part of eluent are evaporated under reduced pressure the mixed solution that 80 volume ratio is formed successively
By TLC tlc analysis, it will show that the eluent of identical main point merges on TLC lamellaes, 19 obtained by eluting order
Component；
D) the obtained in step c) the 4th component is detached with high speed adverse current chromatogram, collects the stream containing target compound
Part, it is concentrated under reduced pressure, obtains crude product；
E) purify gained crude product preparative liquid chromatography to get to the xanthones compound A.
Preferably, in step d), when high speed adverse current chromatogram purifies, n-hexane is used：Ethyl acetate：95wt% second
Alcohol：Water is according to (6.5-7.5)：(2.5-3.5)：(6.5-8.5)：The mixed solution that the volume ratio of (1.5-3.5) is formed is flowing
It is mutually detached, UV detector is monitored under 340nm wavelength, collects target fraction.
As further preferred scheme, n-hexane is used：Ethyl acetate：95wt% ethyl alcohol：Water is according to 7：3：7：3 volume ratio
The mixed solution of formation is that mobile phase is detached.
Preferably, in step e), when being purified with preparative liquid chromatography, use acetonitrile and water according to volume ratio for
60:40 mixed solution carries out isocratic elution as eluent, and UV detector is monitored under 340nm wavelength, collects mesh
Mark fraction.
Drug of the present invention can give patient with various administration routes, including but not limited to oral, transdermal, muscle, skin
Lower and intravenous injection.
The dosage form of drug of the present invention is unlimited, all may be used as long as active constituent can be made effectively to reach internal dosage form
With, including：Tablet, sugar coated tablet, film coated tablet, enteric coated tablet, capsule, hard capsule, soft capsule, oral solution,
Mouth containing agent, granule, electuary, pill, powder, paste, sublimed preparation, suspension, pulvis, solution, injection, suppository, ointment,
Emplastrum, creme, spray, drops, patch etc.；It is preferred that peroral dosage form, such as：Capsule, tablet, oral solution, granule, ball
Agent, powder, sublimed preparation, paste etc..
Drug of the present invention can be used alone, and can also be used in the form of pharmaceutical composition, the medicine group
It refers to other than containing main active, also containing time that be a small amount of and not influencing active ingredient in drug to close object
Want auxiliary material etc. necessary to ingredient and/or pharmaceutically acceptable carrier and various preparations.For example, the drug is oral agents
When type, can contain common excipient, such as adhesive, filler, diluent, tablet agent, lubricant, disintegrant, colorant,
Flavoring agent and wetting agent when necessary can be coated tablet.Suitable filler include cellulose, mannitol, lactose and
Other similar fillers；Suitable disintegrant includes starch, polyvinylpyrrolidone and starch derivatives, such as hydroxyacetic acid
Sodium starch；Suitable lubricant includes, such as magnesium stearate；Suitable pharmaceutically acceptable wetting agent includes dodecyl sulphate
Sodium.
Effective administration dosage of active constituent of the present invention can be with drug used, the pattern of administration and disease to be treated
Disease severity and change.
Heretofore described term is defined as follows：
Term " pharmaceutically acceptable salt " refers to by part (for example, amido) positively charged in the compound and tool
Have opposite-sign it is negatively charged (for example, trifluoracetic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, formic acid, acetic acid, propionic acid,
Succinic acid, 1,5- naphthalenedisulfonic acids, asiatic acid, oxalic acid, tartaric acid, lactic acid, salicylic acid, benzoic acid, valeric acid, diethacetic acid,
It is malonic acid, succinic acid, fumaric acid, pimelic acid, adipic acid, maleic acid, malic acid, sulfamic acid, benzenpropanoic acid, gluconic acid, anti-bad
Hematic acid, niacin, isonicotinic acid, methanesulfonic acid, p-methyl benzenesulfonic acid, citric acid, amino acid) salt that is formed, or it is negative by band in compound
The salt that the part (for example, carboxyl) of charge is formed with positive charge (for example, sodium, potassium, calcium, magnesium).Described is " pharmaceutically acceptable
" refer to having rational benefit/risk suitable for people and without excessive bad side reaction (such as toxicity, stimulation and allergy)
The substance of ratio.
Term " tautomer " refers to because of a certain atom is generated in the rapid movement in two positions in molecule functional group
Isomers, such as：Enol and corresponding ketone.
Term " stereoisomer " refers to the isomers caused by atom in molecule spatially arrangement mode difference, example
Such as：Cis-trans-isomer, enantiomter, rotamer etc..
Term " precursor compound " refers to inactive in vitro, but can be metabolized or be chemically reacted in vivo and turned
The active constituent for turning to the present invention, to play the compound of its pharmacological action.
Compared with prior art, the present invention has following conspicuousness advantageous effect：
The present invention result of study show, xanthones compound A of the present invention：12R-isobractatin is to people
Prostate gland cancer cell PC-3, human cervical carcinoma cell HeLa, Non-small cell lung carcinoma cell A549 and human colon cancer cell HT-29 are equal
With stronger cytotoxicity, IC50 is at 10 μM hereinafter, can obviously inhibit Human Prostate Cancer Cells PC-3, human cervical carcinoma cell
The proliferation of HeLa, Non-small cell lung carcinoma cell A549 and human colon cancer cell HT-29 illustrate xanthones of the present invention
Compound A：12R-isobractatin has the function of inhibiting tumor cell proliferation, it is expected to is used to prepare as active constituent anti-
Tumour medicine has prospect in medicine.
Specific implementation mode
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In the following examples, the experimental methods for specific conditions are not specified, usually according to conventional strip
Part or according to the normal condition proposed by manufacturer.Unless otherwise stated, otherwise percentage and number are calculated by weight.
In following implementation, big bud gamboge picks up from Guangxi province, Song Zhi of the plant through Guangxi medical herb institute in October, 2012
Army researcher identifies that plant sample is stored in Shanghai Univ. of Traditional Chinese Medicine's Innovative TCMs laboratory；
Silica gel column chromatography selects Qingdao Marine Chemical Co., Ltd.'s column chromatography silica gel (200-300 mesh)；
TLC tlc analysis selects Yantai Jiang You silica gel development corporation, Ltd. HSGF254 tlc silica gel plates；
It prepares liquid phase column and selects Xbridge Prep C18OBD column (19 × 250mm, 5 μm).
Embodiment 1：The preparation of 12R-isobractatin
A) the big luxuriant gamboge leaves of 7.6kg are extracted into, reduced pressure diacolation substantially colorless to percolate with 95wt% ethanol percolations
Liquid obtains extract (2.6kg)；
B) extract obtained by step a) is suspended in water, with petroleum ether extraction, obtains the stone of big luxuriant Resina garciniae extract
Oily ether extracts position (700g)；
C) by the petroleum ether extraction position of big luxuriant Resina garciniae extract obtained by step b) by silica gel post separation, with petroleum ether and
Ethyl acetate is according to 100：0~20：Gradient elution, every part of eluent are evaporated under reduced pressure the mixed solution that 80 volume ratio is formed successively
By TLC tlc analysis, it will show that the eluent of identical main point merges on TLC lamellaes, 19 obtained by eluting order
Component；
D) the obtained in step c) the 4th component is detached with high speed adverse current chromatogram, using n-hexane：Ethyl acetate：
95wt% ethyl alcohol：Water is according to 7：3：7：The mixed solution that 3 volume ratio is formed is that mobile phase is detached, rotating speed：850rpm, stream
Speed：2mL/min, UV detector are monitored under 340nm wavelength, collect the target stream containing 12R-isobractatin
Part, merge, is concentrated under reduced pressure, obtains crude product；
E) purified with preparative liquid chromatography to gained crude product, according to volume ratio be 60 with acetonitrile and water:40 mixed solution
Isocratic elution is carried out as eluent, can contain the formic acid of 0.1vol%, flow velocity 15mL/min, ultraviolet inspection in mixed solution
Device is surveyed to be monitored under 340nm wavelength to get to the xanthones compound A：(HPLC is pure by 12R-isobractatin
Degree is 98%).
Analysis obtains after tested：Molecular formula is C28H32O6；ESI-MS：m/z[M+1]+=465；1HNMR (600MHz,
DMSO-d6) and13CNMR (151MHz, DMSO-d6) data be shown in Table 1.
1 12R-isobractatin's of table1HNMR、13CNMR data
Embodiment 2：12R-isobractatin inhibits human tumor cells proliferation test
2.1 experiment material
The xanthones compound A：12R-isobractatin is to extract to obtain from big luxuriant gamboge, purity
98%；Human Prostate Cancer Cells PC-3, human cervical carcinoma cell HeLa are purchased from ATCC companies of the U.S.；Non-small cell lung carcinoma cell
A549, Hong Kong Chinese University pigeon professor grant；Human colon cancer cell HT-29, Tsinghua University professor Xu Naihan grant；People is normal
Prostate gland stroma immortalized cells WPMY-1 is purchased from Chinese Academy of Sciences's cell bank；RPMI1640, fetal calf serum, penicillin and streptomysin,
Purchased from Invitrogen companies of the U.S., Taxol is purchased from Tao Su companies of the U.S.；Propidium iodide (Propidium Iodide, PI) and
RNase A are purchased from Sigma Co., USA.
2.2 test method
Non-small cell lung carcinoma cell A549 and human cervical carcinoma cell HeLa, with containing 10% fetal calf serum, 100U/ml moulds
The DMEM of element and 100 μ g/ml streptomysins trains liquid-based；Human Prostate Cancer Cells PC-3, human colon cancer cell HT-29, with containing 10%
The RPMI1640 of fetal calf serum, 100U/ml penicillin and 100 μ g/ml streptomysins trains liquid-based, in 37 DEG C, 5%CO2And saturation is wet
It cultivates in the incubator of degree, is passed on 0.25% trypsin digestion, logarithmic growth phase cell is for testing.
Human Prostate Cancer Cells PC-3, Non-small cell lung carcinoma cell A549, human cervical carcinoma cell HeLa and people's colon
Cancer cell HT-29 (3*104/ml) is inoculated in 96 orifice plates.Be separately added into final concentration gradient be 1.25 μM, 2.5 μM, 5 μM, 10
μM compound 12R-isobractatin in 96 orifice plates, blank is arranged as positive drug control group in 5-FU, Etoposide
After cultivating 72h, 10ul CCK-8 are added per hole for reagent wells, Normal group, are protected from light incubation 1-4h and are dyed.Use enzyme mark
Instrument detects absorbance value at 450 nm, calculates the growth inhibition ratio of various concentration, growth inhibition ratio %=be (control groups
The average value of average value-treatment group)/control average value × 100%.When the growth inhibition ratio of cell reaches 50%, change
The concentration for closing object is IC50 values.Experimental data uses mean+/-standard error (x-± s) to indicate, is counted using SPSS16.0
Software is analyzed.
2.3 experimental result
The xanthones compound A：12R-isobractatin acts on 72 hours IC of a variety of human tumor cells50
As shown in table 2.
2 xanthones compound A of table：12R-isobractatin inhibits IC50/ μM of (x-± s) value of growth of tumour cell
As can be seen from Table 2, xanthones compound A of the present invention：12R-isobractatin has stronger cell
Toxicity, IC50 is at 10 μM hereinafter, can obviously inhibit Human Prostate Cancer Cells PC-3, Non-small cell lung carcinoma cell A549, Ren Gong
The proliferation of neck cancer cell HeLa and human colon cancer cell HT-29, it is seen that xanthones compound A of the present invention：12R-
Isobractatin can inhibit to concentration dependent the proliferation of tumour cell, have potential antitumor action, it is expected to as
Active constituent is used to prepare antitumor drug, has prospect in medicine.
Finally need indicated herein be：The part preferred embodiment that the above is only the present invention, should not be understood as to this hair
The limitation of bright protection domain, those skilled in the art's the above according to the present invention make some it is nonessential improvement and
Adjustment all belongs to the scope of protection of the present invention.
Claims (6)
1. a kind of medicinal usage of xanthones compound A, the xanthones compound A has chemical constitution shown in Formulas I：Chemistry is entitled：12R-isobractatin；It is characterized in that：The medicinal usage refers to described
In xanthones compound A or its hydrate, pharmaceutically acceptable salt, tautomer, stereoisomer, precursor compound
At least one be used to prepare antitumor drug as active constituent.
2. medicinal usage according to claim 1, it is characterised in that：The antitumor drug is treatment cervix cancer, preceding
The drug of any one or two or more tumours in row gland cancer, adenocarcinoma of lung, intestinal cancer.
3. medicinal usage according to claim 1, it is characterised in that：The xanthones compound A is from big luxuriant rattan
It is extracted in Huang isolated.
4. medicinal usage according to claim 3, it is characterised in that：The xanthones described from big luxuriant gamboge extraction separation
The method of compound A includes the following steps：
A) big luxuriant gamboge leaf is extracted substantially colorless to percolate with 95wt% ethanol percolations, percolate is concentrated under reduced pressure, must extract
Object；
B) extract obtained by step a) is suspended in water, with petroleum ether extraction, obtains the petroleum ether of big luxuriant Resina garciniae extract
Extract position；
C) by the petroleum ether extraction position of big luxuriant Resina garciniae extract obtained by step b) by silica gel post separation, with petroleum ether and acetic acid
Ethyl ester is according to 100：0~20：Gradient elution, every part of eluent pass through the mixed solution that 80 volume ratio is formed after being evaporated under reduced pressure successively
TLC tlc analysis will show that the eluent of identical main point merges, 19 components obtained by eluting order on TLC lamellaes；
D) the obtained in step c) the 4th component is detached with high speed adverse current chromatogram, collects the fraction containing target compound,
It is concentrated under reduced pressure, obtains crude product；
E) purify gained crude product preparative liquid chromatography to get to the xanthones compound A.
5. medicinal usage according to claim 4, it is characterised in that：In step d), when high speed adverse current chromatogram purifies, with just
Hexane：Ethyl acetate：95wt% ethyl alcohol：Water is according to (6.5-7.5)：(2.5-3.5)：(6.5-8.5)：The volume of (1.5-3.5)
Mixed solution than formation is that mobile phase is detached, and UV detector is monitored under 340nm wavelength, collects target stream
Part.
6. medicinal usage according to claim 4, it is characterised in that：In step e), when being purified with preparative liquid chromatography,
Use acetonitrile and water according to volume ratio for 60:40 mixed solution carries out isocratic elution as eluent, and UV detector exists
It is monitored under 340nm wavelength, collects target fraction.
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| CN201810046218.9A CN108272790A (en) | 2018-01-17 | 2018-01-17 | A kind of medicinal usage of xanthones compound A |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1368973A (en) * | 1999-07-01 | 2002-09-11 | 赞塔里斯股份公司 | Novel xanthone compounds, their preparation and use as medicament |
-
2018
- 2018-01-17 CN CN201810046218.9A patent/CN108272790A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1368973A (en) * | 1999-07-01 | 2002-09-11 | 赞塔里斯股份公司 | Novel xanthone compounds, their preparation and use as medicament |
Non-Patent Citations (3)
| Title |
|---|
| BAO-JUN ZHANG ET AL.: "Bioactive scalemic caged xanthones from the leaves of Garcinia bracteata", 《BIOORGANIC CHEMISTRY》 * |
| SRI HARTATI ET AL.: "CYTOTOXIC ISOBRACTATIN (PRENYLATED XANTHONE) EPIMER MIXTURE OF Garcinia eugenifolia", 《INDO. J. CHEM》 * |
| 牛生吏: "大苞藤黄的化学成分及其抗肿瘤活性研究", 《中国博士学位论文全文数据库 医药卫生科技辑》 * |
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