CN103864738A - Phellinus monomer component Phellinus igniarius E and inoscavin A and preparation method thereof as well as application of Phellinus igniarius E and inoscavin A in anticancer drugs - Google Patents
Phellinus monomer component Phellinus igniarius E and inoscavin A and preparation method thereof as well as application of Phellinus igniarius E and inoscavin A in anticancer drugs Download PDFInfo
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- CN103864738A CN103864738A CN201410023204.7A CN201410023204A CN103864738A CN 103864738 A CN103864738 A CN 103864738A CN 201410023204 A CN201410023204 A CN 201410023204A CN 103864738 A CN103864738 A CN 103864738A
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Abstract
The invention discloses Phellinus monomer component Phellinus igniarius E and inoscavin A and a preparation method thereof as well as an application of the Phellinus igniarius E and inoscavin A in anticancer drugs. The Phellinus igniarius E is yellow powder and is dissolved in chloroform, acetone and ethanol, the molecular formula is C24H20O9, and the molecular structure is as shown in the specification; the inoscavin A is yellow powder and is dissolved in chloroform, acetone and ethanol, the molecular formula is C25H18O9, and the molecular structure is as shown in the specification. The monomer component Phellinus igniarius E and inoscavin A extracted from Phellinus have obvious anticancer effect; the preparation method is simple, easy and convenient to operate, high in extraction efficiency and stable in product quality, so that the preparation method can be effectively used for preparation of anticancer drugs.
Description
Technical field
The present invention relates to a kind of Phellinus monomer component Boydii Phellinus rhzomorph E and fine pore fungi element A and preparation method thereof and application on antitumor drug, belong to medical technical field.
Background technology
Tumour is class common disease and a frequently-occurring disease, be body tissue cell under inside and outside various tumorigenesis factor long terms, producer sudden change loses the normal regulation to its growth and differentiation, causes true tumor or vegetation that clonal abnormality hyperplasia and differentiation form.Tumour is divided into innocent tumour and malignant tumour, and malignant tumour is subdivided into again and derives from the cancer of epithelium, the sarcoma that derives from mesenchymal tissue and sarcocarcinoma three classes.Conventionally people's said " cancer " are all malignant tumours of general reference.
Malignant tumour is to threaten one of topmost malignant disease of human health, first cause of the death of current population in the world, latest data statistics, 2007, the whole world 7,900,000 people that have an appointment die from all kinds of cancers, account for 13% of dead sum, have to exceed 1,200 ten thousand tumor cases and made a definite diagnosis, wherein 72% above tumour patient and lethal case all occur in under-developed country, and be the trend of continuous rising, estimate 2015, the lethal number of global tumour will increase to 9,000,000 people, and the year two thousand thirty will exceed 1,200 ten thousand people; At present, the annual pathogenesis of cancer number approximately 2,800,000 of China, death toll exceedes 400,000 people, ranks first of China's various diseases cause of death, and is continuous ascendant trend.Along with social life rhythm is accelerated, competitive pressure increases, and the mankind's mode of life and the change of environment, the positive increase year after year of tumor incidence and death toll, become common disease and the high morbidity of modern society, not only had a strong impact on patient's quality of life, and brought heavy economy and mental burden to family and society, also be the global Social Events of puzzlement, the treatment of cancer and prevention are one of the most urgent problem of global range class all the time.At present, chemotherapy is the Main Means of resisting tumour, in recent years, antitumor drug market, the whole world is rapid growth situation, according to U.S. FDA statistic data, global cancer therapy drug market sale total value, by 24,000,000,000 dollars in 2004, is increased sharply to 39,600,000,000 dollars of 2007.Although the whole world all constantly has new type antineoplastic medicine to come out every year, but the mankind still do not have a kind of effectively means beat cancer so far, constantly find new cancer species simultaneously, and generation and the enhancing of resist/resistance of tumour, make the needs to finding novel effective antitumor medicine seem particularly urgent.Make a general survey of the cancer therapy drug that the whole world was developed during 1981 to 2002, approximately 60% directly or indirectly comes from natural product, fully shows that nature is the most important source that the mankind obtain antitumor drug.In plant, extensively exist the activeconstituents with antitumor action, the priority of camptothecine, vincristine(VCR) and taxol etc. is found, indicate the major progress that natural anti-cancer drugs institute obtains, China's natural resources of Chinese medicinal materials is abundant, and from traditional medicine resource, screening searching anticancer natural activeconstituents or active lead compound are feasible.
Phellinus, base was the sporophore of polyporaceae phellinus originally, Latin formal name used at school: phellinus igniarius(L.ex Fr.) Quel.Have another name called: phelliuns igniarius, sporophore stockless, the flat semisphere of cap or the shape of a hoof.Modern study finds that Phellinus has immunomodulatory, many-sided pharmacologically active such as antitumor, and therefore, it is feasible from Phellinus, finding antitumor activity component.
So far, in prior art, contain the plain A of formula (I) and formula (II) compound Boydii Phellinus rhzomorph E and fine pore fungi and report at the pharmacology aspect the inhibition of various tumor cell strains system as effective constituent.
Summary of the invention
An object of the present invention is to provide a kind of anticancer effect remarkable, can be used to treat tumour patient Phellinus monomer component Boydii Phellinus rhzomorph E and fine pore fungi element A.
Another object of the present invention is to provide the preparation method of a kind of simple, Phellinus monomer component Boydii Phellinus rhzomorph E that extraction efficiency is high and fine pore fungi element A.
Of the present invention also have an object to be to provide Phellinus monomer component Boydii Phellinus rhzomorph E and the application of fine pore fungi element A on antitumor drug.
For achieving the above object, the technical solution used in the present invention is as follows:
Phellinus monomer component Boydii Phellinus rhzomorph E and fine pore fungi element A, is characterized in that, Boydii Phellinus rhzomorph E is yellow powder, is dissolved in chloroform, acetone and ethanol; UV λ max MeOH (nm) (log ε): 383 (4.10); IR (KBr) ν maxcm-13423,1734,1660; Mass spectrum ESI-MS:m/z452; Molecular formula is C
24h
20o
9; Molecular structure is as shown in figure (I):
Fine pore fungi element A is yellow powder, is dissolved in chloroform, acetone and ethanol; UV spectrum UV λ maxMeOH (nm) (log ε): 388 (4.40), 271 (4.22); Infrared spectra IR (KBr) ν max cm-13430,1702; Mass spectrum ESI-MS:m/z462; Molecular formula is C
25h
18o
9; Molecular structure is as shown in figure (II):
The preparation method of Phellinus monomer component Boydii Phellinus rhzomorph E and fine pore fungi element A, comprises the following steps:
(1) dry Phellinus sporophore is pulverized rear with 95% alcohol heating reflux extraction, filter, after filtrate recycling ethanol, concentrating under reduced pressure gained medicinal extract suspends with distilled water, use successively again sherwood oil, ethyl acetate, n-butanol extraction, obtain respectively petroleum ether extract, acetic acid ethyl ester extract, n-butyl alcohol extract;
(2) 200-300 order silica gel mixed sample for acetic acid ethyl ester extract, then makes eluent by 2:1,1:1,1:3 and pure methyl alcohol successively with the volume ratio of chloroform and ethyl ester, carries out silicagel column gradient elution and obtains successively F1, F2, F3, F4 totally four parts;
(3) ODS post in F3 part, press successively the gradient elution of 1:4,1:0 with the volume ratio of methyl alcohol and water, silica-gel plate colour developing merging obtains F3-1, F3-2, F3-3, F3-4, F3-5, wherein, the methyl alcohol that F3-1, F3-2, F3-3 tri-parts are is 1:4 by volume ratio and the mixing solutions wash-out of water obtain, and F3-4, F3-5 two portions are obtained by pure methanol-eluted fractions; The upper Sephadex LH-20 of F3-4, pure methanol-eluted fractions obtains Boydii Phellinus rhzomorph E;
(4) silicagel column in F4 part, take the volume ratio of chloroform and methyl alcohol successively by 1:0,0:1 as eluent, wash-out obtains F4-1, F4-2, F4-3, F4-4 tetra-parts, wherein, F4-1, F4-2 two portions are to be obtained by pure chloroform wash-out, and F4-3, F4-4 two portions are to be obtained by pure methanol-eluted fractions; The upper MCI post of F4-3, be 20%, 40%, 60%, 90% methanol aqueous solution system gradient elution successively by concentration, obtain respectively four part F4-3-1, F4-3-2, F4-3-3, F4-3-4, the upper ODS post of F4-3-3, concentration is the methanol aqueous solution system wash-out of 20%-100%, the merging of silica-gel plate point sample obtains one and under ultraviolet lamp 365nm, shows very strong yellow fluorescence, and further Sephadex LH-20 methyl alcohol purifying obtains fine pore fungi element A.
The Phellinus monomer component Boydii Phellinus rhzomorph E that the present invention makes and fine pore fungi element A have in the application of preparing in antitumor drug.
Beneficial effect of the present invention:
The monomer component Boydii Phellinus rhzomorph E that the present invention extracts from Phellinus and fine pore fungi element A have significant anticancer effect; and preparation method of the present invention is simple, easy to operate, and extraction efficiency is high; constant product quality, thus can be effectively for the preparation of anti-tumor drug.
Accompanying drawing explanation
Fig. 1 is that Boydii Phellinus rhzomorph E, fine pore fungi element A and positive control drug 5 FU 5 fluorouracil (5-FU) suppress dose-effect curve to the increment of liver cancer (HepG2) cell.
Fig. 2 is that Boydii Phellinus rhzomorph E, fine pore fungi element A and positive control drug 5 FU 5 fluorouracil (5-FU) suppress dose-effect curve to the increment of cancer of the stomach (MG80-3) cell.
Fig. 3 is that Boydii Phellinus rhzomorph E, fine pore fungi element A and positive control drug 5 FU 5 fluorouracil (5-FU) suppress dose-effect curve to the increment of colorectal carcinoma (HCT-116) cell.
Fig. 4 is that Boydii Phellinus rhzomorph E, fine pore fungi element A and positive control drug 5 FU 5 fluorouracil (5-FU) suppress dose-effect curve to the increment of cervical cancer (HeLa) cell.
Fig. 5 is that Boydii Phellinus rhzomorph E, fine pore fungi element A and positive control drug 5 FU 5 fluorouracil (5-FU) suppress dose-effect curve to the increment of mammary cancer (MCF-7) cell.
Embodiment
Below essentiality content of the present invention is described in conjunction with specific embodiments in further detail, but do not limit in any form the present invention.
Embodiment
The preparation method of Phellinus monomer component Boydii Phellinus rhzomorph E and fine pore fungi element A, comprises the following steps:
(1) get dry Phellinus sporophore 10kg, pulverize, by 3 times (6 times of amounts, 5 times of amounts, 4 times of amounts) of 95% alcohol heating reflux extraction, extract 2 hours at every turn, extracting temperature is 80 ℃, filters, and merges No. three extracting solutions and obtains total extracting solution; Reclaim after ethanol and be evaporated to medicinal extract shape, adding distil water is made suspension, then use sherwood oil successively, ethyl acetate, n-butanol extraction, obtain respectively petroleum ether extract 65g, acetic acid ethyl ester extract 462g, n-butyl alcohol extract 308g;
(2) 200-300 order silica gel mixed sample for 462g acetic acid ethyl ester extract, then makes eluent by 2:1,1:1,1:3 and pure methyl alcohol successively with the volume ratio of chloroform and ethyl ester, carries out silicagel column gradient elution and obtains successively F1, F2, F3, F4 totally four parts;
(3) ODS in F3 part, press successively the gradient elution of 1:4,1:0 with the volume ratio of methyl alcohol and water, silica-gel plate colour developing merging obtains F3-1, F3-2, F3-3, F3-4, F3-5, wherein, the methyl alcohol that F3-1, F3-2, F3-3 tri-parts are is 1:4 by volume ratio and the mixing solutions wash-out of water obtain, and F3-4, F3-5 two portions are obtained by pure methanol-eluted fractions; The upper SephadexLH-20 of F3-4, pure methanol-eluted fractions obtains Boydii Phellinus rhzomorph E120mg; UV λ max MeOH (nm) (log ε): 383 (4.10); IR (KBr) ν maxcm-13423,1734,1660; Mass spectrum ESI-MS:m/z452;
1h with
13c nuclear magnetic data is in table 1;
(4) silicagel column in F4 part, take the volume ratio of chloroform and methyl alcohol successively by 1:0,0:1 as eluent, wash-out obtains F4-1, F4-2, F4-3, F4-4 tetra-parts, wherein, F4-1, F4-2 two portions are to be obtained by pure chloroform wash-out, and F4-3, F4-4 two portions are to be obtained by pure methanol-eluted fractions; The upper MCI post of F4-3, be 20%, 40%, 60%, 90% methanol aqueous solution system gradient elution successively by concentration, obtain respectively four part F4-3-1, F4-3-2, F4-3-3, F4-3-4, the upper ODS of F4-3-3, concentration is the methanol aqueous solution system wash-out of 20%-100%, the merging of silica-gel plate point sample obtains one and under ultraviolet lamp 365nm, shows very strong yellow fluorescence, and further SephadexLH-20 methyl alcohol purifying obtains fine pore fungi element A67mg; UV spectrum UV λ maxMeOH (nm) (log ε): 388 (4.40), 271 (4.22); Infrared spectra IR (KBr) ν max cm-13430,1702; Mass spectrum ESI-MS:m/z462;
1h with
13c nuclear magnetic data is in table 1.
Table 1 Boydii Phellinus rhzomorph E and fine pore fungi element A
1h and
13c nmr spectrum data (in DMSO, J in Hzand in ppm)
Below by the anti-tumor activity of evidence Phellinus monomer component of the present invention Boydii Phellinus rhzomorph E and fine pore fungi element A.
One, the configuration of experiment material and solution
1. the configuration of nutrient solution: the Gibco powder dissolution of one bag of DMEM is in 1L distilled water, with the filter filtration of 0.22 μ m;
2. foetal calf serum: buy in Hangzhou folium ilicis chinensis company limited, be placed in-20 ℃ of preservations, use after 56 ℃ of water-bath deactivation 30min;
3. dual anti-: penicillin streptomycin is according to the proportional arrangement of 1:1, with 0.22 μ m ,-20 ℃ of preservations;
4. tetrazolium bromide (MTT): with PBS configuration, with the filter filtration of 0.22 μ m, concentration is 5mg/ml, preserves for-20 ℃ long-term, preserves 2 weeks for 4 ℃; Buy the Sigma company in the U.S..
5. dimethyl sulfoxide (DMSO) (Dimethyl sulfoxide, DMSO): buy the Sigma company in the U.S.;
6.50mm2 Tissue Culture Flask, 96 porocyte culturing bottles: buy the company in Costar.
Two, instrument and equipment
Electronic balance: BT253 type, Sartorius AG's product;
Automatic dual pure water distiller: SZ-93, Jintan Jing Bo company product;
Ultrapure water equipment: Rios83ol PE, U.S. Mi Libo;
Ultralow Temperature Freezer: MDF-U40865, SANYO GS;
Ultrasonic Cleaners: SB25-12DTD, the new sesame in Ningbo;
Electric heating constant-temperature blowing drying box: DHG-9243BS-III, Shanghai new talent;
Vertical pressure steam sterilizer: LDZX-40KB, Shenan Medical Appliances Factory, Shanghai;
CO2 incubator: 2306-Z, SHELLAB company of the U.S.;
Clean work station: SW-CJ-1F type, Suzhou purifies;
Inverted microscope: NIB-100, Ningbo Yongxin;
Pipettor: French PIPETMAN company;
Spectrophotometer: 722S, Shanghai Precision Scientific Apparatus Co., Ltd;
Ice-making machine: AF100, SCOTSMAN company;
Refrigerated centrifuge: 3-16K, SIGMA company
Supercentrifuge: 16K, Zhuhai unexpected rival;
High speed freezing centrifuge: 5415R, German Eppendorf company;
Thermostat water bath: HH-6, Jie Ruier Electrical Appliances Co., Ltd of Jintan City;
Microscope: eclipse te300, nilon company;
Microplate reader: MULISKAN MK3, Thermo forma Instrument Ltd..
Three, experimental technique
3.1 cell cultures
This tests liver cancer HepG2 used, Gastric Cancer MGC 80-3, colorectal carcinoma HCT-116, cervical cancer HeLa, MCF-7 Breast Cancer Cell is adherent growth cell strain, the DMEM nutrient solution that employing contains 10% foetal calf serum (FBS), and add the culture system of penicillin 100IU/mL and Streptomycin sulphate 100 μ g/mL to cultivate.Culture environment is 37 ℃, and 5% CO2 incubator is changed nutrient solution once, within every 3 days, gone down to posterity once, get in the cell of logarithmic phase and test for every 2 days.
3.2MTT method detects cell proliferation situation
Succinodehydrogenase in viable cell plastosome can make exogenous MTT be reduced to water-insoluble bluish voilet Jie Jing formazan (Formazan) and be deposited in cell, and dead cell is without this function.Formazan in dimethyl sulfoxide (DMSO) (DMSO) energy dissolved cell, measures its absorbance value by microplate reader at 490nm wavelength place, and within the scope of certain cell count, the amount that MTT crystallization forms is directly proportional to cell count.According to the absorbance A recording, judge viable cell quantity, A value is larger, and cytoactive is stronger.
Above-mentioned 5 kinds of tumour cells are inoculated in 96 well culture plates with the concentration of 5000/ml, and every hole inoculum size is 100 μ L.After cell attachment, be divided into blank group (adding DMEM nutrient solution 100 μ L), solvent control group (containing 0.05%DMSO), positive controls Fluracil (50 μ g/mL) and medication group (25,50,100,200,400 μ g/ml)), establish 6 multiple holes for every group, the cumulative volume in every hole is 200 μ L.Respectively at being replaced by serum-free medium 180 μ L after 48h, and add MTT (concentration is 5mg/mL) 20 μ L, continue to cultivate after 4h, the centrifugal supernatant of abandoning, every hole adds the DMSO of 150 μ L, and concussion 10min shakes up, and first a ceremonial jade-ladle, used in libation particle is fully dissolved.On enzyme-linked immunosorbent assay instrument, with wavelength 490nm, the zeroing of reagent control group, surveys absorbancy (A490) value, repeats 3 times, gets its mean value.Calculate cell IC50 value by SPSS method, calculate inhibitory rate of cell growth by following formula:
Inhibitory rate of cell growth=((be worth-experimental group of control group average A 490 average A 490 is worth)/control group average A 490 is worth) × 100%.
Four, experimental result
Table 2 Boydii Phellinus rhzomorph E and fine pore fungi element A are to supplying examination tumor cell line half growth inhibitory concentration (IC
50, μ M)
Claims (3)
1. Phellinus monomer component Boydii Phellinus rhzomorph E and fine pore fungi element A, is characterized in that, Boydii Phellinus rhzomorph E is yellow powder, is dissolved in chloroform, acetone and ethanol; UV λ max MeOH (nm) (log ε): 383 (4.10); IR (KBr) ν maxcm-13423,1734,1660; Mass spectrum ESI-MS:m/z452; Molecular formula is C
24h
20o
9; Molecular structure is as shown in figure (I):
Fine pore fungi element A is yellow powder, is dissolved in chloroform, acetone and ethanol; UV spectrum UV λ maxMeOH (nm) (log ε): 388 (4.40), 271 (4.22); Infrared spectra IR (KBr) ν max cm-13430,1702; Mass spectrum ESI-MS:m/z462; Molecular formula is C
25h
18o
9; Molecular structure is as shown in figure (II):
2. the preparation method of Phellinus monomer component Boydii Phellinus rhzomorph E as claimed in claim 1 and fine pore fungi element A, is characterized in that comprising the following steps:
(1) dry Phellinus sporophore is pulverized rear with 95% alcohol heating reflux extraction, filter, after filtrate recycling ethanol, concentrating under reduced pressure gained medicinal extract suspends with distilled water, use successively again sherwood oil, ethyl acetate, n-butanol extraction, obtain respectively petroleum ether extract, acetic acid ethyl ester extract, n-butyl alcohol extract;
(2) 200-300 order silica gel mixed sample for acetic acid ethyl ester extract, then makes eluent by 2:1,1:1,1:3 and pure methyl alcohol successively with the volume ratio of chloroform and ethyl ester, carries out silicagel column gradient elution and obtains successively F1, F2, F3, F4 totally four parts;
(3) ODS post in F3 part, press successively the gradient elution of 1:4,1:0 with the volume ratio of methyl alcohol and water, silica-gel plate colour developing merging obtains F3-1, F3-2, F3-3, F3-4, F3-5, wherein, the methyl alcohol that F3-1, F3-2, F3-3 tri-parts are is 1:4 by volume ratio and the mixing solutions wash-out of water obtain, and F3-4, F3-5 two portions are obtained by pure methanol-eluted fractions; The upper Sephadex LH-20 of F3-4, pure methanol-eluted fractions obtains Boydii Phellinus rhzomorph E;
(4) silicagel column in F4 part, take the volume ratio of chloroform and methyl alcohol successively by 1:0,0:1 as eluent, wash-out obtains F4-1, F4-2, F4-3, F4-4 tetra-parts, wherein, F4-1, F4-2 two portions are to be obtained by pure chloroform wash-out, and F4-3, F4-4 two portions are to be obtained by pure methanol-eluted fractions; The upper MCI post of F4-3, be 20%, 40%, 60%, 90% methanol aqueous solution system gradient elution successively by concentration, obtain respectively four part F4-3-1, F4-3-2, F4-3-3, F4-3-4, the upper ODS post of F4-3-3, concentration is the methanol aqueous solution system wash-out of 20%-100%, the merging of silica-gel plate point sample obtains one and under ultraviolet lamp 365nm, shows very strong yellow fluorescence, and further Sephadex LH-20 methyl alcohol purifying obtains fine pore fungi element A.
3. Phellinus monomer component Boydii Phellinus rhzomorph E as claimed in claim 1 or 2 and the application of fine pore fungi element A on antitumor drug.
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| CN112574893A (en) * | 2020-12-16 | 2021-03-30 | 广东省微生物研究所（广东省微生物分析检测中心） | Phellinus baumii, and preparation method and application of fermentation product thereof |
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| CN102977114A (en) * | 2012-11-20 | 2013-03-20 | 浙江省中医药研究院 | Inoscavin A as a monomeric component in phellinus as well as prepearation method and application thereof |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102977114A (en) * | 2012-11-20 | 2013-03-20 | 浙江省中医药研究院 | Inoscavin A as a monomeric component in phellinus as well as prepearation method and application thereof |
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| CHANG-SHENG WU ET AL.: "Phenolic compounds with NF-κB inhibitory effects from fungus Phellinus baumii", 《BIOORG. MED. CHEM. LETT.》 * |
| CHANG-SHENG WU ET AL.: "Phenolic compounds with NF-κB inhibitory effects from fungus Phellinus baumii", 《BIOORG. MED. CHEM. LETT.》, vol. 21, 13 April 2011 (2011-04-13), pages 3261 - 3267 * |
| IN-KYOUNG LEE ET AL.: "Styrylpyrones from the medicinal fungus Phellinus baumii", 《BIOORG. MED. CHEM. LETT.》 * |
| IN-KYOUNG LEE ET AL.: "Styrylpyrones from the medicinal fungus Phellinus baumii", 《BIOORG. MED. CHEM. LETT.》, vol. 20, 25 July 2010 (2010-07-25), pages 5459 - 5461 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112574893A (en) * | 2020-12-16 | 2021-03-30 | 广东省微生物研究所（广东省微生物分析检测中心） | Phellinus baumii, and preparation method and application of fermentation product thereof |
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