CN104892714A - 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 and a kind ofly isolatedly from glossy ganoderma there is antitumor action and can the new compound of multi-drug resistant (MDR) of inhibition tumor cell.
The invention still further relates to the preparation method of this compound.
The invention still further relates to and preparing the application in antitumor drug with this compound.
Background technology
Malignant tumour often claims cancer, is the common disease of serious threat human health, frequently-occurring disease.Three large main method of current treatment malignant tumour comprise chemotherapy, surgical operation and radiotherapy.Wherein chemotherapy still occupies very consequence in the complex therapy of tumour, but still fails at present to reach satisfied curative effect to the treatment of the solid tumor accounting for malignant tumour more than 90%, and it exists two large major obstacles: the generation of the resistance of medicine and toxic reaction.Cell toxicant class antitumour drug is while killing tumor cell, normal tissue cell also produces damaging action in various degree, that is because it lacks enough selectivity to tumour cell, the key factor that when therefore toxic reaction becomes chemotherapy of tumors, drug dose is limited.In chemotherapy process, tumour cell produces to medicine the major reason that insensitive phenomenon and resistance are chemotherapy of tumors failures, is also chemotherapy of tumors urgent need to solve the problem.Therefore how to improve chemotherapeutic treatment index, how to break through the focus that the large obstacle of chemotherapy two has become research at present.From herbal medicine, find toxicity is low, curative effect is high antitumor activity component become one of main points in current antitumor drug development strategy.Natural compounds contained by plant has wide material sources, cheap, low toxin, therefore from herbal medicine, finds high-efficiency low-toxicity, and acting on single-minded antitumor drug has vast potential for future development.
Ganoderma lucidum is the dry sporophore of the red sesame of polyporaceae Ganoderma Mycophyta [Ganoderma lucidum (Leyss.ex Fr.) Karst] or purple sesame [Ganoderma japonicum (Fr.) Lloyd].Warm in nature, taste is sweet, there is invigorating the spleen and replenishing QI, strengthening by means of tonics, the effect of strengthening the body resistance to consolidate the constitution, be usually used in treatment or the assisting therapy of tumour clinically.For the research of the antitumor effective constituent of glossy ganoderma, mainly for ganoderan and Ganoderma lucidum triterpenes components.Antitumor result of study shows, Ganoderma triterpenoids has restraining effect to the growth of kinds of tumor cells and transfer.To the research of Ganoderma lucidum triterpenes components 20th century the eighties reach climax, there is more than the 150 kind of separated qualification of Ganoderma lucidum triterpenes components at present, we are in the effective constituent research of glossy ganoderma antitumor action, the triterpene compound that isolation identification one is new, called after 5 α-lanosta-7,9,25-triene-24 α, 26-dihydroxy-3-one.Pharmacological experiment shows, this compound has anti-tumor activity.For this compound through overtesting, determine rational preparation method.
Summary of the invention
The object of this invention is to provide a kind of from glossy ganoderma the isolated new compound with antitumor action---Ganoderma triterpenoids (5 α-lanosta-7,9,25-triene-24 α, 26-dihydroxy-3-one).
Another object of the present invention is to provide preparation this compound method.
Another object of the present invention is to provide the application of this compound in preparation tumor.
The object of the present invention is achieved like this, the compound of a kind of structure formula I of the present invention, and its chemical structural formula is as follows:
（Ⅰ）。
The preparation method of the compound that the present invention is above-mentioned, comprises the following steps:
A) glossy ganoderma alcohol or alcoholic solution are extracted more than once or 2 times, filter, collect filtrate, then concentrating under reduced pressure is dry, obtain alcohol extract;
B) added water by alcohol extract, after petroleum ether extraction degreasing, then with extraction into ethyl acetate, the acetic acid ethyl acetate extract of acquisition, again with the extraction of pH 8-12 alkaline aqueous solution, is got ethyl acetate phase evaporate to dryness, is obtained crude product;
C) crude product of acquisition is carried out chromatographic separation and purification, obtain pure formula I compound.
Above-mentioned steps C) the crude product step of carrying out chromatographic separation and purification comprise as follows: 1) crude product is carried out column chromatography on silica gel, use petroleum ether-ethyl acetate gradient elution, the volume ratio obtaining petroleum ether-ethyl acetate is the eluate of 1:1; 2) volume ratio of getting petroleum ether-ethyl acetate is that the eluate of 1:1 is separated through preparative high performance liquid chromatography, and methanol-water gradient elution, obtains pure compound (1) from the wash-out position that the volume ratio of methanol-water is 85:15.
Above-mentioned pH 8-12 alkaline aqueous solution adopts saturated NaHCO
3the aqueous solution.
The application of compound or derivatives thereof in preparation tumor of said structure formula I of the present invention.
Described tumour is human chronic polymorpho nuclear leukemia cells strain K562, human myeloid leukemia cell strain HL60, human oral 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 for the treatment of significant quantity.
Wherein the compound of structure formula I and/or the content of its derivative are greater than more than 50%, and especially more than 90%.
The present invention contains the application of pharmaceutical composition in preparation tumor of the compound or derivatives thereof of the structure formula I for the treatment of significant quantity.
Specifically, the invention provides the preparation method of compound, compound of the present invention can synthetic, but preferably separation and Extraction from natural phant, to obtain naturally occurring, hypotoxic natural compounds.In a preferred embodiment of the invention, separation and purification compound of the present invention from the Chinese traditional Chinese medicine glossy ganoderma, its preparation process comprises:
A) glossy ganoderma alcohol or alcoholic solution are extracted one or many, filter, collect filtrate, then concentrating under reduced pressure is dry, obtain alcohol extract;
B) added water by alcohol extract, after petroleum ether extraction degreasing, then with extraction into ethyl acetate, the acetic acid ethyl acetate extract of acquisition is again with saturated NaHCO
3aqueous solution extraction, gets ethyl acetate phase evaporate to dryness, obtains crude product.
C) crude product of acquisition is carried out chromatographic separation and purification, obtain pure formula I compound.
Above-mentioned steps C) the crude product step of carrying out chromatographic separation and purification comprise as follows: 1) crude product is carried out column chromatography on silica gel, uses petroleum ether-ethyl acetate gradient elution, obtain petroleum ether-ethyl acetate (volume ratio 1:1) eluate; 2) get petroleum ether-ethyl acetate (volume ratio 1:1) eluate to be separated through preparative high performance liquid chromatography, methanol-water gradient elution, obtain pure compound (1) from methanol-water (volume ratio 85:15) wash-out position.
In accordance with a further aspect of the present invention, provide the pharmaceutical composition containing the compounds of this invention, can by the compounds of this invention being added pharmaceutically acceptable carrier or excipient or optional other compositions and make the pharmaceutical composition being suitable for Clinical practice.
In accordance with a further aspect of the present invention, the application of the compounds of this invention in preparation tumor is provided, there is the effect of killing tumor cell.
Described tumour is preferably human chronic polymorpho nuclear leukemia cells strain K562, human myeloid leukemia cell strain HL60, human oral epidermoid carcinoma cell strain KB, human esophagus cancer cell strain OE-19, human colon cancer cell strain SW620.
Experiment shows that wherein the compound of structure formula I and/or the content of its derivative are greater than more than 50% in the pharmaceutical composition of the compound containing structure formula I and/or its derivative, especially more than 90%, and result for the treatment of is better.
The invention has the beneficial effects as follows:
the restraining effect of tumor cell proliferation,5 α-lanosta-7 of the present invention, 9,25-triene-24 α, 26-dihydroxy-3-one have significant restraining effect to SW620 and OE-19 cell proliferation, all show obvious dose-effect relationship (see Fig. 1, Fig. 2).Drug effect is in the IC of SW620 and OE-19 cell 48 h
50value is 3.71 μ g/ml and 6.25 μ g/ml respectively.Act on the IC of K562, HL60 and KB cell 48 h
50value is 34.38 μ g/ml, 21.46 μ g/ml and 14.04 μ g/ml respectively.Experimental result shows, compound of the present invention has anti-tumor activity.As from the foregoing, compound of the present invention (1)---5 α-lanosta-7,9,25-triene-24 α, 26-dihydroxy-3-one preparation method is easy, and processing condition are gentle, compound (1) is white crystal, experiment proves to adopt present invention process step, and the product purity of acquisition can reach 98%, apparently higher than the step of prior art.Compound of the present invention can as the medicine for the treatment of tumour, and it has the effect of killing tumor cell, especially has good curative effect to human colon carcinoma.
Accompanying drawing explanation
Fig. 1 is the compounds of this invention (1) (effect 48h) the amount effect relation curve figure to the effect of SW620 cell inhibitory effect.
Fig. 2 is the compounds of this invention (1) (effect 48h) the amount effect relation curve figure to the effect of OE-19 cell inhibitory effect.
Embodiment
Below by the description to the embodiment of the present invention, describe in detail but do not limit the present invention.
the preparation of embodiment 1 compound (1)
material sourceglossy ganoderma (
ganoderma lucidum(Leys.ex Fr.) Karst) purchased from Fujian China Xian Zhi building bio tech ltd, the sample sample of this glossy ganoderma is deposited in pharmaceutical college of Medical University Of Fujian.
extraction and separationby dry with the glossy ganoderma of pulverizing by dehydrated alcohol refluxing extraction 3 times, each 2h, extracting solution No. 2 filter paper filterings, remove ethanol acquisition alcohol-extracted extract with rotatory evaporator.After alcohol-extracted extract adds suitable quantity of water, use sherwood oil successively, extraction into ethyl acetate, the acetic acid ethyl acetate extract obtained extracts with saturated sodium bicarbonate aqueous solution again, take out ethyl acetate phase concentrating under reduced pressure evaporate to dryness and obtain crude product, crude product is carried out column chromatography on silica gel, with the petroleum ether-ethyl acetate wash-out of volume ratio 1:1, get petroleum ether-ethyl acetate (volume ratio 1:1) eluate to be separated through preparative high performance liquid chromatography (water generation Pre-150B preparative high performance liquid chromatography instrument), adopt the methanol-water wash-out of volume ratio 85:15, pure compound (1) is obtained from methanol-water (volume ratio 85:15) wash-out position.Compound (1) is white crystal, and purity reaches 98% after tested.
the determination of chemical structure of embodiment 2 compound (1)
structure determinationby Shimadzu-3100 spectrophotometric determination UV spectrum, at CDCl
3with BRUKER nuclear magnetic resonance spectrometer record NMR spectrum in solution, measure mass spectrum with Agilent 6210 time-of-flight mass spectrometer.
the physico-chemical property of compound (1)the compounds of this invention (1) is white crystal, fusing point 183 – 185 DEG C, UV(EtOH) λ max 254nm, Liebermann-Burchard reacting positive,
1h-NMR(CDCl
3, 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 '), δ 1.42 (1H, m, H-15), δ 1.72 (1H, m, H-15 '), δ 1.35 (1H, m, H-16), 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 '), and 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(CDCl
3, 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 in conjunction with above-mentioned physicochemical data, confirm this compound
(1)structural formula as follows:
the biological experiment of embodiment 3 compound (1) antitumous effect and analysis
1, materials and methods
clone and reagenthuman chronic polymorpho nuclear leukemia cells strain K562, human myeloid leukemia cell strain HL60, human oral epidermoid carcinoma cell strain KB, human esophagus cancer cell strain OE-19 and human colon cancer cell strain SW620.These cells are cultivated in containing the RPMI RPMI-1640 of 10% calf serum, puts 37 DEG C, the CO of 5% saturated humidity
2cultivate in incubator.Above-mentioned
compound (1)---ganoderma triterpenoids
chemistry is by name5 α-lanosta-7,9,25-triene-24 α, 26-dihydroxy-3-one, come from
the preparation of embodiment 1 obtains.
analysis of cell proliferationk562, HL60, KB, OE-19 and SW620 cell of taking the logarithm vegetative period, is inoculated in 96 well culture plates according to cell strain difference by certain density, every hole 190 μ l.Dosing immediately after inoculating cell.Experimental group adds different concns medicine 10 μ l/ hole, and cell controls group adds the serum-free medium containing equivalent concentration DMSO, and blank group is that 190 μ l RPMI 1640 add 10 μ l without medicine solvent, often organizes 3 multiple holes.After K562, HL60, KB, OE-19 and SW620 hatch 48 h, add the MTT 20 μ l/ hole of 5 mg/ml, 37 DEG C hatch 4 h after centrifugal (2000 rpm, 10 minutes), carefully suck supernatant, add 150 μ l/ hole DMSO and mix, each group all measures the OD value in each hole in 570 nm wavelength places, calculate inhibitory rate of cell growth, inhibiting rate=(1-drug treating hole mean OD value/cell control well mean OD value) × 100%.Take drug level as transverse axis, inhibiting rate value is that the longitudinal axis draws cell inhibitory effect amount effect relation curve.The IC of drug level when calculating 48 h by Logit method
50value, experiment repetition 3 times, averages.
, result
the restraining effect result of tumor cell proliferationabove-mentioned
compound (1)ganoderma triterpenoids (5 α-lanosta-7,9,25-triene-24 α, 26-dihydroxy-3-one) has significant restraining effect to SW620 and OE-19 cell proliferation, all shows obvious dose-effect relationship (see Fig. 1, Fig. 2).Drug effect is in the IC of SW620 and OE-19 cell 48 h
50value is 3.71 μ g/ml and 6.25 μ g/ml respectively.Act on the IC of K562, HL60 and KB cell 48 h
50value is 34.38 μ g/ml, 21.46 μ g/ml and 14.04 μ g/ml respectively.Experimental result shows, compound of the present invention has anti-tumor activity.
Claims (9)
1. a compound for structure formula I, its chemical structural formula is as follows:
（Ⅰ）。
2. the preparation method of the described compound of claim 1, comprises the following steps:
A) glossy ganoderma alcohol or alcoholic solution are extracted more than once or 2 times, filter, collect filtrate, then concentrating under reduced pressure is dry, obtain alcohol extract;
B) added water by alcohol extract, after petroleum ether extraction degreasing, then with extraction into ethyl acetate, the acetic acid ethyl acetate extract of acquisition, again with the extraction of pH 8-12 alkaline aqueous solution, is got ethyl acetate phase evaporate to dryness, is obtained crude product;
C) crude product of acquisition is carried out chromatographic separation and purification, obtain pure formula I compound.
3. the preparation method of compound according to claim 2, it is characterized in that step C) the crude product step of carrying out chromatographic separation and purification comprise as follows: 1) crude product is carried out column chromatography on silica gel, use petroleum ether-ethyl acetate gradient elution, the volume ratio obtaining petroleum ether-ethyl acetate is the eluate of 1:1; 2) volume ratio of getting petroleum ether-ethyl acetate is that the eluate of 1:1 is separated through preparative high performance liquid chromatography, and methanol-water gradient elution, obtains pure compound (1) from the wash-out position that the volume ratio of methanol-water is 85:15.
4. the preparation method of compound according to claim 1 and 2, is characterized in that pH 8-12 alkaline aqueous solution adopts saturated NaHCO
3the aqueous solution.
5. the application of compound or derivatives thereof in preparation tumor of structure formula I according to claim 1.
6. application according to claim 5, is characterized in that described tumour is human chronic polymorpho nuclear leukemia cells strain K562, human myeloid leukemia cell strain HL60, human oral epidermoid carcinoma cell strain KB, human esophagus cancer cell strain OE-19 or human colon cancer cell strain SW620.
7. the pharmaceutical composition of the compound or derivatives thereof of the structure formula I according to claim 1 containing treatment significant quantity.
8. pharmaceutical composition according to claim 7, is characterized in that wherein the compound of structure formula I and/or the content of its derivative are greater than more than 50%, especially more than 90%.
9. the application of pharmaceutical composition in preparation tumor of the compound or derivatives thereof of the structure formula I according to claim 1 containing treatment significant quantity.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| JP2021519745A (en) * | 2019-03-25 | 2021-08-12 | 広州白雲山漢方現代薬業有限公司Ｇｕａｎｇｚｈｏｕ Ｈａｎｆａｎｇ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．，Ｌｔｄ． | Methods and Drugs to Reverse Drug Resistance of Tumor Cells to Antineoplastic Drugs |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2021519745A (en) * | 2019-03-25 | 2021-08-12 | 広州白雲山漢方現代薬業有限公司Ｇｕａｎｇｚｈｏｕ Ｈａｎｆａｎｇ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．，Ｌｔｄ． | Methods and Drugs to Reverse Drug Resistance of Tumor Cells to Antineoplastic Drugs |
| JP7064589B2 (en) | 2019-03-25 | 2022-05-10 | 広州白雲山漢方現代薬業有限公司 | Methods and drugs to reverse drug resistance of tumor cells to antitumor drugs |
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Effective date of registration: 20220120 Address after: No.6, Chuangxin Road, high tech Zone, Fuzhou City, Fujian Province, 350108 Patentee after: FUJIAN XIANZHILOU BIOLOGICAL SCIENCE & TECHNOLOGY CO.,LTD. Address before: 350108, No. 1 School Road, Fuzhou Town, Minhou County, Fujian, China Patentee before: FUJIAN MEDICAL University |