CN104892714B - New ganoderma lucidum triterpene, preparation method and medicinal uses thereof - Google Patents
New ganoderma lucidum triterpene, preparation method and medicinal uses thereof Download PDFInfo
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Abstract
The present invention discloses a new ganoderma lucidum triterpene, a preparation method and medicinal uses thereof, wherein the new ganoderma lucidum triterpene is a compound having the following structure formula (I). The preparation method comprises: extracting ganoderma lucidum one time or more than or equal to 2 times with an alcohol or an alcohol solution, filtering, collecting the filtrate, and carrying out pressure reducing concentration drying to obtain an alcohol extract; adding water to the alcohol extract, carrying out extraction degreasing with petroleum ether, extracting with ethyl acetate, extracting the obtained ethyl acetate extraction solution with an alkaline aqueous solution with the pH value of 8-12, taking the ethyl acetate phase, and evaporating to achieve a dry state so as to obtain a crude product; and carrying out chromatography separation purification on the obtained crude product so as to obtain the pure compound represented by the formula (I). The invention further provides the applications of the new ganoderma lucidum triterpene in preparation of tumor treating drugs.
Description
Technical field
The present invention relates to a kind of isolated from Ganoderma to there is antitumor action and the multiple resistance to of tumor cell can be suppressed
The noval chemical compound of the property of medicine (MDR).
The invention still further relates to the preparation method of this compound.
The invention still further relates to the application in preparing antitumor drug of this compound.
Background technology
Malignant tumor often claims cancer, is the commonly encountered diseases of serious threat human health, frequently-occurring disease.Treat malignant tumor at present
Three big main method include chemotherapy, surgical operation and radiotherapy.Wherein chemotherapy is still occupied in the Comprehensive Treatment of tumor
Particularly important status, but the treatment to the solid tumor accounting for malignant tumor more than 90% still fails to reach the curative effect of satisfaction at present,
There are two big major obstacles in it: the generation of the drug resistance of medicine and toxic reaction.Cell toxicant class antineoplastic agent is at killing tumor cell
While, normal tissue cell also produces damaging action in various degree, and tumor cell is lacked enough due to it by that
Selectivity, the key factor that when therefore toxic reaction becomes chemotherapy of tumors, drug dose is limited.Tumor cell pair in chemotherapy process
Medicine generation insensitive phenomenon i.e. drug resistance is the major reason that chemotherapy of tumors is failed, is also the difficulty of chemotherapy of tumors urgent need solution
Topic.The most how to improve chemotherapeutic treatment index, how breaking through the big obstacle of chemotherapy two has become the focus of research at present.From Chinese herbal medicine
The anti-tumor active ingredient that middle searching toxicity is low, curative effect is high becomes one of main points in current antitumor drug development strategy.By
In the native compound contained by plant, there is wide material sources, cheap, low toxin, from Chinese herbal medicine, therefore find height
Effect low toxicity, acting on single-minded antitumor drug has vast potential for future development.
Ganoderma lucidum is Polyporaceae Ganoderma Mycophyta Ganoderma lucidum (Leyss. Ex Fr.) Karst. [Ganoderma lucidum (Leyss.ex Fr.)
Karst] or the dry sporophore of Ganoderma [Ganoderma japonicum (Fr.) Lloyd].Warm in nature, sweet in the mouth, has invigorating middle warmer benefit
Gas, strengthening by means of tonics, effect of strengthening the body resistance, be usually used in treatment or the auxiliary treatment of tumor clinically.Ganoderma antitumor is had
The research of effect composition, mainly for ganoderan and Ganoderma lucidum triterpenes components.Antitumor result of study shows, Ganoderma triterpenoids is to many
Growth and the transfer of planting tumor cell have inhibitory action.To the research of Ganoderma lucidum triterpenes components 20th century the eighties reach
Climax, has had more than 150 kind of Ganoderma lucidum triterpenes components by isolation identification, and we are having for Ganoderma antitumor action
In effect composition Study, one new triterpenoid compound of isolation identification, named 5 α-lanosta-7,9,25-triene-24
α, 26-dihydroxy-3-one.Pharmacological experiment shows, this compound has anti-tumor activity.Pass through for this compound
Test, it is determined that reasonably preparation method.
Summary of the invention
It is an object of the invention to provide a kind of isolated noval chemical compound spirit with antitumor action from Ganoderma
Sesame triterpene (5 α-lanosta-7,9,25-triene-24 α, 26-dihydroxy-3-one).
Further object is that this compound method is prepared in offer.
It is still another object of the present invention to provide the application in preparation tumor of this compound.
The object of the present invention is achieved like this, the compound of a kind of structure formula I of the present invention, its chemical constitution
Formula is as follows:
(I).
The preparation method of the compound that the present invention is above-mentioned, comprises the following steps:
A) Ganoderma alcohol or alcoholic solution are extracted more than once or 2 times, filter, collect filtrate, then concentrating under reduced pressure is dried, and obtains
Obtain alcohol extraction thing；
B) alcohol extraction thing is added water, after petroleum ether extraction defat, then with ethyl acetate extract, it is thus achieved that ethyl acetate extraction
Take liquid to extract with pH 8-12 alkaline aqueous solution again, take ethyl acetate and be evaporated mutually, it is thus achieved that crude product；
C) crude product of acquisition is carried out chromatographic separation and purification, obtain pure formula I compound.
Above-mentioned steps C) crude product carry out the step of chromatographic separation and purification and include the following: 1) crude product is carried out on silica gel post
Chromatography, uses petroleum ether-ethyl acetate gradient elution, it is thus achieved that the volume ratio of petroleum ether-ethyl acetate is the eluate of 1:1；2) take
The volume ratio of petroleum ether-ethyl acetate is that the eluate of 1:1 separates through preparative high performance liquid chromatography, methanol-water gradient elution,
Pure compound (1) is obtained from the eluting position that the volume ratio of methanol-water is 85:15.
Above-mentioned pH 8-12 alkaline aqueous solution uses saturated NaHCO3Aqueous solution.
The application in preparation tumor of the compound or derivatives thereof of said structure formula I of the present invention.
Described tumor is human chronic polymorpho nuclear leukemia cells strain K562, human myeloid leukemia cell strain HL60, population
Chamber epidermoid carcinoma cell strain KB, human esophagus cancer cell strain OE-19 or human colon cancer cell strain SW620.
The present invention contains the pharmaceutical composition of the compound or derivatives thereof of the structure formula I of therapeutically effective amount.
Wherein the compound of structure formula I and/or the content of its derivant are more than more than 50%, and especially more than 90%.
The pharmaceutical composition of the compound or derivatives thereof of the structure formula I that the present invention contains therapeutically effective amount is controlled in preparation
Treat the application in tumour medicine.
Specifically, the present invention provides the preparation method of compound, and the compound of the present invention can be with synthetic, but preferably
Be separation and Extraction from natural plants, to obtain native compound naturally occurring, hypotoxic.Excellent of the present invention
Select in embodiment, the isolated and purified compound of the present invention from China Chinese medicine Ganoderma, its preparation process includes:
A) Ganoderma alcohol or alcoholic solution are extracted one or many, filter, collect filtrate, then concentrating under reduced pressure is dried, it is thus achieved that
Alcohol extraction thing；
B) alcohol extraction thing is added water, after petroleum ether extraction defat, then with ethyl acetate extract, it is thus achieved that ethyl acetate extraction
Take liquid again with saturated NaHCO3Aqueous solution extraction, takes ethyl acetate and is evaporated mutually, it is thus achieved that crude product.
C) crude product of acquisition is carried out chromatographic separation and purification, obtain pure formula I compound.
Above-mentioned steps C) crude product carry out the step of chromatographic separation and purification and include the following: 1) crude product is carried out on silica gel post
Chromatography, uses petroleum ether-ethyl acetate gradient elution, it is thus achieved that petroleum ether-ethyl acetate (volume ratio 1:1) eluate；2) oil is taken
Ether-ethyl acetate (volume ratio 1:1) eluate through preparative high performance liquid chromatography separate, methanol-water gradient elution, from methanol-
Water (volume ratio 85:15) eluting position obtains pure compound (1).
In accordance with a further aspect of the present invention, it is provided that containing the pharmaceutical composition of the compounds of this invention, can be by by this
Bright compound add pharmaceutically acceptable carrier or excipient or optionally other compositions and make the medicine that is suitable to Clinical practice
Compositions.
In accordance with a further aspect of the present invention, it is provided that the compounds of this invention application in preparation tumor, have
The effect of killing tumor cell.
Described tumor be preferably human chronic polymorpho nuclear leukemia cells strain K562, human myeloid leukemia cell strain HL60,
Human mouth epidermoid carcinoma cell strain KB, human esophagus cancer cell strain OE-19, human colon cancer cell strain SW620.
Experiment shows in the pharmaceutical composition of the compound containing structure formula I and/or its derivant, wherein structural formula
(I) compound and/or the content of its derivant are more than more than 50%, especially more than 90%, and therapeutic effect is preferable.
The invention has the beneficial effects as follows: the inhibitory action of tumor cell proliferation, the 5 α-lanosta-7 of the present invention, 9,25-
Triene-24 α, 26-dihydroxy-3-one have significant inhibitory action to SW620 and OE-19 cell proliferation, all show
Significantly dose-effect relationship (see Fig. 1, Fig. 2).Medicine acts on the IC of SW620 and OE-19 cell 48 h50Value is 3.71 μ g/ respectively
Ml and 6.25 μ g/ml.Act on the IC of K562, HL60 and KB cell 48 h50Value is 34.38 μ g/ml, 21.46 μ g/ml respectively
With 14.04 μ g/ml.Test result indicate that, the compound of the present invention has anti-tumor activity.From the foregoing, it will be observed that the chemical combination of the present invention
Thing (1) 5 α-lanosta-7,9,25-triene-24 α, 26-dihydroxy-3-one preparation method is easy, technique bar
Part is gentle, and compound (1) is white crystal, and experiment proves to use present invention process step, it is thus achieved that product purity up to 98%,
Step apparently higher than prior art.The compound of the present invention can be as the medicine for the treatment of tumor, and it has killing tumor cell
Effect, especially human colon carcinoma is had preferable curative effect.
Accompanying drawing explanation
Fig. 1 is the compounds of this invention (1) (effect 48h) the amount effect relation curve figure to SW620 cell inhibitory effect effect.
Fig. 2 is the compounds of this invention (1) (effect 48h) the amount effect relation curve figure to OE-19 cell inhibitory effect effect.
Detailed description of the invention
Below by the description to the embodiment of the present invention, describe in detail but be not intended to the present invention.
The preparation of embodiment 1 compound (1)
Material source Ganoderma (Ganoderma lucidum(Leys.ex Fr.) Karst) purchased from Fujian China Xian Zhi building
Bio tech ltd, the specimen sample of this Ganoderma is deposited in pharmaceutical college of Medical University Of Fujian.
Extracting Ganoderma dehydrated alcohol reflux, extract, that is dry and that pulverize 3 times and separate, each 2h, extracting solution is with 2
Number filter paper filtering, removes ethanol by rotary evaporator and obtains alcohol-extracted extract.After alcohol-extracted extract adds suitable quantity of water, successively with petroleum ether,
Ethyl acetate extract, it is thus achieved that acetic acid ethyl acetate extract again with saturated sodium bicarbonate aqueous solution extract, take out ethyl acetate subtract each other
Pressure concentration is evaporated to obtain crude product, crude product carries out on silica gel column chromatography, with the petroleum ether-ethyl acetate eluting of volume ratio 1:1, takes
Through preparative high performance liquid chromatography, (water generation Pre-150B preparative is efficient in petroleum ether-ethyl acetate (volume ratio 1:1) eluate
Chromatograph of liquid) separate, use the methanol-water eluting of volume ratio 85:15, obtain from methanol-water (volume ratio 85:15) eluting position
To pure compound (1).Compound (1) is white crystal, and purity reaches 98% after tested.
The determination of chemical structure of embodiment 2 compound (1)
Structure determination Shimadzu-3100 spectrophotometric determination ultraviolet spectra, at CDCl3Solution is used BRUKER
Nuclear magnetic resonance chemical analyser record NMR spectra, measures mass spectrum with Agilent 6210 time of-flight mass spectrometer.
The physicochemical property the compounds of this invention (1) of compound (1) is white crystal, fusing point 183 185 DEG C, UV(EtOH)
λmax 254nm；Liebermann-Burchard reacting positive； 1H-NMR(CDCl3, 500MHz): δ 1.78 (1H, m, H-1), δ
2.29 (1H, m, H-1 '), δ 2.38 (1H, m, H-2), δ 2.80 (1H, m, H-2 '), δ 1.54 (1H, m, H-5), δ 2.05 (1H, m,
H-6), δ 2.14 (1H, m, H-6 '), δ 5.53 (1H, d,J=6.5Hz, H-7), δ 5.41 (1H, d,J=5.5Hz, H-11), δ
2.10 (1H, m, H-12), δ 2.29 (1H, m, H-12 '), and δ 1.42 (1H, m, H-15), δ 1.72 (1H, m, H-15 '), δ 1.35
(1H, m, H-16), and δ 2.02 (1H, m, H-16 '), δ 1.59 (1H, m, H-17), δ 0.61 (3H, s, H-18), δ 1.11 (3H, s, H-
19), δ 1.46 (1H, m, H-20), δ 0.95 (3H, d,J=5.0Hz, H-21), δ 1.01 (1H, m, H-22), δ 1.54 (1H, m, H-
22 '), δ 1.57 (1H, m, H-23), δ 1.75 (1H, m, H-23 '), δ 4.23 (1H, m, H-24), δ 4.20 (1H, d,J =
13.0Hz, H-26), δ 4.35 (1H, d,J=13.0Hz, H-26 '), δ 5.13 (1H, s, H-27), δ 5.17 (1H, s, H-27 '),
δ 0.90 (3H, s, H-28), δ 1.15 (3H, s, H-29), δ 1.22 (3H, s, H-30)；13C-NMR(CDCl3, 125MHz): δ
36.63 (C-1), 34.86 (C-2), 216.94 (C-3), 47.49 (C-4), 50.31 (C-5), 23.68 (C-6), 119.94 (C-
7), 142.85 (C-8), 144.52 (C-9), 37.21 (C-10), 117.27 (C-11), 37.82 (C-12), 43.76 (C-13),
50.73 (C-14), 31.46 (C-15), 27.86 (C-16), 50.85 (C-17), 15.72 (C-18), 22.47 (C-19), 36.13
(C-20), 18.55 (C-21), 32.08 (C-22), 32.41 (C-23), 75.58 (C-24), 149.62 (C-25), 64.00 (C-
26), 112.89 (C-27), 25.37 (C-28), 25.44 (C-29), 22.06 (C-30)；ESI-MS:m/z 453.4 [M-H]-1。
From HMBC spectrogram and hsqc spectrum diagram data, and combine above-mentioned physicochemical data, confirm the structural formula of this compound (1) such as
Under:
The biological experiment of embodiment 3 compound (1) antitumaous effect and analysis
1, material and method
Cell line and reagent human chronic polymorpho nuclear leukemia cells strain K562, human myeloid leukemia cell strain HL60, people
Oral cavity epidermoid carcinoma cell strain KB, human esophagus cancer cell strain OE-19 and human colon cancer cell strain SW620.These cells are being contained
The RPMI RPMI-1640 of 10% calf serum is cultivated, puts 37 DEG C, the CO of 5% saturated humidity2Incubator is cultivated.Above-mentioned
Compound (1) Ganoderma triterpenoids chemistry entitled 5 α-lanosta-7,9,25-triene-24 α, 26-dihydroxy-3-
One, comes from the preparation of embodiment 1 and obtains.
Analysis of cell proliferation is taken the logarithm K562, HL60, KB, OE-19 and SW620 cell of trophophase, according to cell strain
Difference is inoculated in 96 well culture plates by certain density, every hole 190 μ l.Dosing immediately after inoculating cell.Experimental group adds not
With acute drug 10 μ l/ hole, cell controls group adds the serum-free medium containing equivalent concentration DMSO, and blank group is 190 μ
L RPMI 1640 adds 10 μ l without medicine solvent, often the multiple holes of group 3.After K562, HL60, KB, OE-19 and SW620 hatch 48 h, add
Enter the MTT 20 μ l/ hole of 5 mg/ml, hatch after 4 h centrifugal (2000 rpm, 10 minutes), carefully suck supernatant, add 150 for 37 DEG C
μ l/ hole DMSO mixes, each group all OD values in each hole of mensuration at 570 nm wavelength, calculating inhibitory rate of cell growth, and suppression ratio=
(1-drug treating hole mean OD value/cell control well mean OD value) × 100%.With drug level as transverse axis, suppression ratio value is vertical
Axle draws cell inhibitory effect amount effect relation curve.The IC of drug level when calculating 48 h by Logit method50Value, tests repetition 3
Secondary, average.
, result
Above-mentioned compound (1) Ganoderma triterpenoids of the inhibitory action result of tumor cell proliferation (5 α-lanosta-7,9,
25-triene-24 α, 26-dihydroxy-3-one) SW620 and OE-19 cell proliferation had significant inhibitory action, equal table
Reveal obvious dose-effect relationship (see Fig. 1, Fig. 2).Medicine acts on the IC of SW620 and OE-19 cell 48 h50Value is 3.71 respectively
μ g/ml and 6.25 μ g/ml.Act on the IC of K562, HL60 and KB cell 48 h50Value is 34.38 μ g/ml, 21.46 μ g/ respectively
Ml and 14.04 μ g/ml.Test result indicate that, the compound of the present invention has anti-tumor activity.
Claims (2)
1. a preparation method for Ganoderma triterpenoids, comprises the following steps:
A) Ganoderma alcohol or alcoholic solution are extracted more than once or 2 times, filter, collect filtrate, then concentrating under reduced pressure is dried, it is thus achieved that alcohol
Extract；
B) alcohol extraction thing is added water, after petroleum ether extraction defat, then with ethyl acetate extract, it is thus achieved that acetic acid ethyl acetate extract
Extract with pH 8-12 alkaline aqueous solution again, take ethyl acetate and be evaporated mutually, it is thus achieved that crude product；
C) crude product of acquisition is carried out chromatographic separation and purification, obtain pure compound (1)
；
Step C) crude product carry out the step of chromatographic separation and purification and include the following: 1) crude product is carried out on silica gel column chromatography, use
Petroleum ether-ethyl acetate gradient elution, it is thus achieved that the volume ratio of petroleum ether-ethyl acetate is the eluate of 1:1；2) take petroleum ether-
The volume ratio of ethyl acetate be 1:1 eluate through preparative high performance liquid chromatography separate, methanol-water gradient elution, from methanol-
The volume ratio of water is that the eluting position of 85:15 obtains pure compound (1).
The preparation method of compound the most according to claim 1, it is characterised in that pH 8-12 alkaline aqueous solution uses saturated
NaHCO3Aqueous solution.
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| CN108299536A (en) * | 2018-04-10 | 2018-07-20 | 福建医科大学 | A kind of triterpene and preparation method thereof with reverse multiple drug resistance of tumor effect |
| CN109464473A (en) * | 2018-11-29 | 2019-03-15 | 杨凌萃健生物工程技术有限公司 | A kind of residual ganodenic acid extract of low agriculture and preparation method thereof |
| CN109758486A (en) * | 2019-03-25 | 2019-05-17 | 广州白云山汉方现代药业有限公司 | Ganodenna Lucidum P.E is preparing the application in artitumor multi-medicine-resistant medicine |
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| CN101747400B (en) * | 2008-12-17 | 2012-09-05 | 湖北工业大学 | Lanostane type triterpenoid with anti-tumor activity, preparation method and application |
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