CN100526330C - Fasciation naematoloma ligarine extraction, preparing method thereof and use in preparing pharmaceutical for treating tumour - Google Patents
Fasciation naematoloma ligarine extraction, preparing method thereof and use in preparing pharmaceutical for treating tumour Download PDFInfo
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- CN100526330C CN100526330C CNB2006101260919A CN200610126091A CN100526330C CN 100526330 C CN100526330 C CN 100526330C CN B2006101260919 A CNB2006101260919 A CN B2006101260919A CN 200610126091 A CN200610126091 A CN 200610126091A CN 100526330 C CN100526330 C CN 100526330C
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- ergosterol
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Abstract
The invention discloses a cluster naematolin ligarine extract, which separates ergosterin peroxidate and two monomer compounds of ergosterin. The invention also provides making method of extract from cluster naematolin fruiting body and mycelium for industrial manufacturing, which is fit for treat tumour drug.
Description
Technical field:
The invention discloses a kind of naematoloma fasciculare ligroin extraction, and further separate wherein two principal monomer compound ergosterol peroxides and ergosterol, their purposes in preparation medicine for treating tumor thing are provided simultaneously, have belonged to Chinese medicine extracts active ingredients preparation method and medicinal use applied technical field.
Background technology:
The naematoloma fasciculare (Naematoloma fasciculare) that the present invention is alleged claims again: the yellow mushroom of clustering, the tough black umbrella of poison, the yellow tough umbrella that clusters, bitter is the poisonous mushroom that after a kind of the eating the people is got killed.Through consulting domestic and foreign literature, the research of relevant naematoloma fasciculare is less, and particularly aspect antitumour drug usefulness, not seeing provides determining of its extraction process and pharmacologically active.
Summary of the invention:
The invention discloses a kind of naematoloma fasciculare ligroin extraction, have antineoplastic pharmaceutical use.
The present invention has also further isolated two monomeric compounds from the naematoloma fasciculare ligroin extraction:
1. ergosterol peroxide (ergosteroL peroxide), its molecular formula is: C28H44O3, molecular weight: M=428, structural formula is as follows:
2. ergosterol (ergosteroL), its molecular formula is: C
28H
44O, molecular weight: M=396, structural formula is as follows:
The invention provides the preparation method who from naematoloma fasciculare sporophore and mycelium, extracts above-mentioned substance, be applicable to suitability for industrialized production.
The present invention further provides the pharmaceutical use of naematoloma fasciculare ligroin extraction in the treatment tumour.
Naematoloma fasciculare ligroin extraction of the present invention, can be by a kind of preparing in following two kinds of methods:
Method one:
With naematoloma fasciculare sporophore or mycelium 30-40 ℃ oven dry, after the pulverizing, the sherwood oil refluxing extraction, sample size is 1-3: 3-5 with the quantity of solvent ratio, three times repeatedly, merges petroleum ether extract, concentrate, water-bath steaming petroleum ether solvent promptly gets naematoloma fasciculare ligroin extraction of the present invention.
Method two:
Naematoloma fasciculare sporophore or mycelium 30-40 ℃ of oven dry, after the pulverizing, are handled with hot methanol (40-60 ℃) lixiviate earlier, quantity of methyl alcohol is 1～2 times of drug powder volume, extract repeatedly 1～3 time, merge methanol extract liquid, concentrate, add 4-6 times of distilled water again and become suspension, the petroleum ether extraction three times that adds 1/2-1 multiple proportions example merges petroleum ether extraction liquid, concentrates, water-bath steaming petroleum ether solvent promptly gets naematoloma fasciculare ligroin extraction of the present invention.
The naematoloma fasciculare ligroin extraction is the yellow-green colour lotion.
To the naematoloma fasciculare ligroin extraction carry out gas chromatograph mass spectrometer analyze the collection of illustrative plates (see figure 1).
Its analytical results is seen sherwood oil makings analytical results table:
Sherwood oil gas chromatograph mass spectrometer analytical results table
| Retention value | Peak area | Peak area % | Peak height | Peak height % | Compound | Similarity % |
| 6.35 | 311142 | 0.57 | 219923 | 1.54 | The n-tetradecane hydrocarbon | 96 |
| 7.258 | 384500 | 0.7 | 240361 | 1.68 | 2, the 6-d-tert-butyl-p-cresol | 86 |
| 8.177 | 552326 | 1.01 | 361757 | 2.53 | The hexadecane hydrocarbon | 96 |
| 8.933 | 134949 | 0.25 | 85384 | 0.6 | The heptadecane hydrocarbon | 91 |
| 9.158 | 793076 | 1.45 | 475036 | 3.33 | CycLohexane，1，5-di isopropyL1-2， 3-dimethyL-C 14H 28 | 77 |
| 9.717 | 747382 | 1.36 | 467130 | 3.27 | The octodecane hydrocarbon | 96 |
| 9.983 | 540892 | 0.99 | 221514 | 1.55 | Dibutyl phthalate+15 |
92，89 |
| 10.533 | 230631 | 0.42 | 139080 | 0.97 | 16 methyl carbonates | 91 |
| 10.792 | 2415737 | 4.41 | 967010 | 6.77 | 16 |
95 |
| 11.175 | 780527 | 1.42 | 490421 | 3.44 | The |
95 |
| 11.7 | 1007101 | 1.84 | 665843 | 4.66 | 9，12-Octadecadienoic acid，methyL ester C 19H 34O 2 | 97 |
| 11.75 | 108307 | 0.2 | 84272 | 0.59 | 9-Otadecenoic acid(Z)-，methyL ester C 19H 36O 2 | 83 |
| 12.075 | 41237897 | 75.24 | 7820617 | 54.81 | 9，12-Octadecadienoic acid C 18H 32O 2 | 92 |
| 12.2 | 404148 | 0.74 | 249966 | 1.75 | Otadecenoic acid C 18H 36O 2 | 88 |
| 12.542 | 780954 | 1.43 | 476716 | 3.34 | The n- |
90 |
| 14.5 | 879181 | 1.6 | 433764 | 3.04 | Tetracosa |
92 |
| 16.008 | 832924 | 1.52 | 342509 | 2.4 | The |
92 |
| 18.808 | 901927 | 1.65 | 239344 | 1.68 | The Octacosane hydrocarbon | 91 |
| 23.042 | 1082943 | 1.98 | 209894 | 1.47 | Three |
90 |
| 29.05 | 668681 | 1.22 | 82984 | 0.58 | The n-dotriacontane hydrocarbon | 93 |
The further separation of naematoloma fasciculare ligroin extraction also can be got ergosterol peroxide and two monomeric compounds of ergosterol, obtain by following method:
With the naematoloma fasciculare extract, last 200-300 order silicagel column separates, be wet method dress post, with eluting solvent (hexanaphthene: ethyl acetate=6-8: 5-9) wash-out, with 1/10th column volumes is a cut, collect the cut of Rf value 0.49-0.52 and merge into ergosterol peroxide, collect the cut of Rf value 0.70-0.75 and merge into ergosterol.
The fusing point of gained monomeric compound ergosterol peroxide is 177-179 ℃, white needle; Fusing point: 178 ℃; Solvability: be soluble in sherwood oil, chloroform, ethyl acetate, acetone, be slightly soluble in ethanol, methyl alcohol, water insoluble, the aceticanhydride strong sulfuric acid response positive, its spectrogram is seen accompanying drawing 2～9.
The fusing point of monomeric compound ergosterol is 152-155 ℃, white needle; Solvability: be soluble in sherwood oil, chloroform, ethyl acetate, acetone, be slightly soluble in ethanol, methyl alcohol, water insoluble, the aceticanhydride strong sulfuric acid response positive, its spectrogram is seen accompanying drawing 10～17.
Through pharmacologically active screening, above-mentioned ligroin extraction and two pharmacologically actives that monomeric compound has antitumor (human breast carcinoma and liver cancer).
Press practice of pharmacy, naematoloma fasciculare ligroin extraction of the present invention or some monomeric compounds can be made the medicine of various clinical pharmaceutical dosage form as antitumor (human breast carcinoma and liver cancer), said medicament is a said formulation on any pharmaceutics.
Above-mentioned ligroin extraction or any monomeric compound that pharmaceutical composition of the present invention contains effective in cure significant quantity are activeconstituents, and contain one or more pharmaceutically acceptable carriers.
Carrier above is meant the pharmaceutical carrier of pharmaceutical field routine, comprises thinner, vehicle, weighting agent, tamanori, wetting agent, disintegrating agent, absorption enhancer, tensio-active agent, absorption carrier.
The present invention can composition form be applied to the patient of this treatment by oral, rectum, vein, intramuscular injection or parenteral admin mode.Conventional production method according to pharmaceutical field prepares various formulations such as tablet, granule, electuary, capsule, suppository, sprays, sustained release dosage and injection.Also can make its activeconstituents and one or more carriers or drug regimen, make required formulation.
Medicine of the present invention preferably contains the naematoloma fasciculare ligroin extraction of 1%-99% or the vehicle of some monomeric compounds and 99%-1% (comprising the medicine that other compatibilities are used), preferably contain the naematoloma fasciculare ligroin extraction of 30%-80% or the vehicle of some monomeric compounds and 70%-20% (comprising the medicine that other compatibilities are used), preferably contain the naematoloma fasciculare ligroin extraction of 60%-70% or the vehicle of some monomeric compounds and 40%-30% (comprising the medicine that other compatibilities are used).
Following pharmacological evaluation has confirmed the pharmacologically active that naematoloma fasciculare ligroin extraction and two principal monomer compounds wherein have antitumor (human breast carcinoma and liver cancer).
The antitumor action of naematoloma fasciculare PetroChina Company Limited. ether extract and monomeric compound ergosterol peroxide and ergosterol
Summary naematoloma fasciculare (N.fascicuLare) PetroChina Company Limited.'s ether extract and monomeric compound ergosterol peroxide and ergosterol, external application mtt assay has detected the growth-inhibiting effect to human breast cancer cell (MCF-7), has detected in the body lotus H
22The influence of knurl mouse tumor growth, experimental result shows that all it has favorable anti-tumor effect.
1 material
1.1 medicine: the naematoloma fasciculare ligroin extraction is the yellow-green colour lotion.
The monomeric compound ergosterol peroxide is white needle.
The monomeric compound ergosterol is white needle.
Injection 5-FU is Shanghai Xudong Hipu Medicine Co., Ltd's product
1.2 MCF-7 cell and lotus H
22The struma mouse provides by the institute of oncology, Jilin Province.
1.3 animal: Kunming mouse, body weight 20-22g, male, available from Changchun High-technology Medical Animal Experiment Research Center.
2 methods and result
2.1 the external growth-inhibiting effect of ligroin extraction to human breast cancer cell (MCF-7).
Getting concentration is 1 * 10
5The tumour cell suspension of individual/mL, every hole 100 μ L are inoculated in 96 orifice plates, add to be subjected to reagent thing, every hole to add dose 100 μ L 3 parallel holes of every kind of dosage next day.37 ℃, 5%CO
2Full closing after humidity cultivates 48h, centrifugal again abandon supernatant after every hole add MTT20 μ L, cultivate 4h after, every hole adds 100 μ L dimethyl sulfoxide (DMSO) (DMSO), micro oscillator vibration 5min puts and measures each hole on the microplate reader at 570nm wavelength place absorbance.
The results are shown in Table 1, the external growth to human breast cancer cell (MCF-7) of ligroin extraction has certain restraining effect, the amount effect relationship.
The external growth-inhibiting effect of table 1 ligroin extraction to human breast cancer cell (MCF-7)
Compare with control group
*P＜0.05,
*P＜0.01,
* *P＜0.01
2.2 ligroin extraction and two monomeric compound bodies are interior to lotus H
22The growth-inhibiting effect of knurl rat liver cancer.
Get the kind mouse ascites fluid cancer cells of inoculation 7d, making number of cells with physiological saline is 1 * 10
6The cell suspension of/mL, it is subcutaneous to be inoculated in the right armpit of mouse with every mouse 0.1mL, random packet behind the 24h, 8 every group, begin gastric infusion every day simultaneously, irritate that body of stomach is long-pending to be 0.2mL/kg.Control group is irritated stomach with equivalent physiological saline, and 7d put to death mouse on the 8th day continuously, won the knurl piece, after weighing respectively, calculated tumor control rate.
The results are shown in Table 2, ligroin extraction (250mg/kg, 100mg/kg), ergosterol peroxide (100mg/kg, 50mg/kg) and ergosterol (50mg/kg) are to lotus H
22The growth of knurl rat liver cancer has the obvious suppression effect, and inhibiting rate is respectively 68.7%, 29.8%, 12.8%, 57.5%, 63.8%.
Table 2 ligroin extraction and two monomeric compounds are to lotus H
22The influence of knurl rat liver cancer growth
Compare with control group
*P＜0.05,
*P＜0.01
2.3 ligroin extraction and two monomeric compound bodies are interior to lotus H
22The influence of knurl mouse immune system.
Get the kind mouse ascites fluid cancer cells of inoculation 7d, making number of cells with physiological saline is 1 * 10
6The cell suspension of/mL, it is subcutaneous to be inoculated in the right armpit of mouse with every mouse 0.1mL, random packet behind the 24h, 8 every group, begin gastric infusion every day simultaneously, irritate that body of stomach is long-pending to be 0.2mL/kg.Control group is irritated stomach with equivalent physiological saline, and 7d put to death mouse on the 8th day continuously, won spleen and thymus gland, after weighing respectively, calculated spleen index and thymus index.
The results are shown in Table 2, ligroin extraction (250mg/kg, 100mg/kg), ergosterol peroxide (100mg/kg, 50mg/kg) and ergosterol (50mg/kg) are to lotus H
22Knurl mouse immune system does not have negative effect, has significant difference with the contrast of 5-FU group.
Table 3 ligroin extraction and two monomeric compounds are to lotus H
22The influence of knurl mouse immune system
Compare with control group:
*: p＜0.05,
*: p＜0.01;
Compare with the 5-FU group:
△: p＜0.05,
△ △: p＜0.01
3 conclusions
Naematoloma fasciculare ligroin extraction and monomeric compound ergosterol peroxide and ergosterol have obvious antineoplastic, and immune organ and body weight are not had detrimentally affect.
Description of drawings
Fig. 1 is a sherwood oil component gas chromatograph mass spectrometer collection of illustrative plates.
Fig. 2 is the electron impact mass spectra figure of compound ergosterol peroxide.
Fig. 3 is the EFI material spectrogram of compound ergosterol peroxide.
Fig. 4 is the ultraviolet absorpting spectrum of compound ergosterol peroxide.
Fig. 5 is the infrared absorption pattern of compound ergosterol peroxide.
Fig. 6 is the 13C-NMR collection of illustrative plates of compound ergosterol peroxide.
Fig. 7 is the 1H-NMR collection of illustrative plates of compound ergosterol peroxide.
Fig. 8 is the DEPT-135 collection of illustrative plates of compound ergosterol peroxide.
Fig. 9 is the DEPT-90 collection of illustrative plates of compound ergosterol peroxide.
Figure 10 is the electron impact mass spectra figure of compound ergosterol.
Figure 11 is the electrospray ionization mass spectrum figure of compound ergosterol.
Figure 12 is the infrared absorption pattern of compound ergosterol.
Figure 13 is the ultraviolet absorpting spectrum of compound ergosterol.
Figure 14 is the 13C-NMR collection of illustrative plates of compound ergosterol.
Figure 15 is the 1H-NMR collection of illustrative plates of compound ergosterol.
Figure 16 is the DEPT-90 collection of illustrative plates of compound ergosterol.
Figure 17 is the DEPT-135 collection of illustrative plates of compound ergosterol.
Embodiment:
By following examples the present invention is described for example further, and do not limit the present invention in any way, under the prerequisite that does not deviate from technical solution of the present invention, any change or change that those of ordinary skills that the present invention did are realized easily all will fall within the claim scope of the present invention.
Naematoloma fasciculare sporophore 1kg 40 ℃ of oven dry, after the pulverizing, is handled with 50 ℃ of lixiviates of hot methanol earlier, quantity of methyl alcohol is 1.5 times of drug powder volume, extract repeatedly 2 times, merge methanol extract liquid 2500mL, be concentrated into 250mL, add 5 times of distilled water again and become suspension, the petroleum ether extraction three times that adds 1 multiple proportions example merges petroleum ether extraction liquid 3500mL, concentrates, water-bath steaming petroleum ether solvent promptly gets ligroin extraction 4.3g.Its gas chromatograph mass spectrometer is analyzed collection of illustrative plates and is seen Fig. 1.
With the naematoloma fasciculare ligroin extraction 3.0g of embodiment 1 gained, last silicagel column separates.Wherein, silicagel column is a 200-300 order silica gel, wet method dress post; Eluting solvent is a hexanaphthene: ethyl acetate=7: 5.Can get monomeric compound ergosterol peroxide 230mg and ergosterol 14mg; Fusing point is respectively 177-179 ℃ and 152-155 ℃.
The fusing point of gained monomeric compound ergosterol peroxide is 177-179 ℃, white needle; Fusing point: 178 ℃; Solvability: be soluble in sherwood oil, chloroform, ethyl acetate, acetone, be slightly soluble in ethanol, methyl alcohol, water insoluble, the aceticanhydride strong sulfuric acid response positive, its spectrogram is seen accompanying drawing 2～9.
The fusing point of monomeric compound ergosterol is 152-155 ℃, white needle; Solvability: be soluble in sherwood oil, chloroform, ethyl acetate, acetone, be slightly soluble in ethanol, methyl alcohol, water insoluble, the aceticanhydride strong sulfuric acid response positive, its spectrogram is seen accompanying drawing 10～17.
With 30 ℃ of oven dry of naematoloma fasciculare sporophore 1kg, after the pulverizing,, extract repeatedly three times with 2 times of quantity of methyl alcohol with 60 ℃ of hot methanol lixiviates, merge methanol extract liquid 3000mL, concentrate 300mL, add 5 times of distilled water again and become suspension, add the petroleum ether extraction three times of 1 multiple proportions example, merge petroleum ether extraction liquid 5000mL, concentrate, the water-bath steaming petroleum ether promptly gets naematoloma fasciculare ligroin extraction 5.6g.Its gas chromatograph mass spectrometer is analyzed collection of illustrative plates and is seen Fig. 1.
With embodiment 3 gained naematoloma fasciculare ligroin extraction 3.0g, last silicagel column separates.Wherein, silicagel column is a 200-300 order silica gel, wet method dress post; Eluting solvent is a hexanaphthene: ethyl acetate=6: 5.Can get monomeric compound ergosterol peroxide 257mg and ergosterol 18mg; Fusing point is respectively 177-179 ℃ and 152-155 ℃.
The fusing point of gained monomeric compound ergosterol peroxide is 177-179 ℃, white needle; Fusing point: 178 ℃; Solvability: be soluble in sherwood oil, chloroform, ethyl acetate, acetone, be slightly soluble in ethanol, methyl alcohol, water insoluble, the aceticanhydride strong sulfuric acid response positive, its spectrogram is seen accompanying drawing 2～9.
The fusing point of monomeric compound ergosterol is 152-155 ℃, white needle; Solvability: be soluble in sherwood oil, chloroform, ethyl acetate, acetone, be slightly soluble in ethanol, methyl alcohol, water insoluble, the aceticanhydride strong sulfuric acid response positive, its spectrogram is seen accompanying drawing 10～17.
With G after naematoloma fasciculare ligroin extraction, monomeric compound ergosterol peroxide and the dosing of ergosterol difference
4Funnel filters, and injection is made in filtrate packing sterilization, and other project should meet requirement under Pharmacopoeia of People's Republic of China version injection liquid in 2005 item.
Naematoloma fasciculare mycelium 1000g 45 ℃ of oven dry, after the pulverizing, is handled with 55 ℃ of lixiviates of hot methanol earlier, quantity of methyl alcohol is 1.5 times of drug powder volume, extracts repeatedly 2 times, merges methanol extract liquid 3000mL, be concentrated into 300mL, add 5 times of distilled water again and become suspension, add the petroleum ether extraction three times of 1 multiple proportions example, merge petroleum ether extraction liquid 5000mL, concentrate, water-bath steaming petroleum ether solvent promptly gets ligroin extraction, and yield is 2.4g.Its gas chromatograph mass spectrometer is analyzed collection of illustrative plates and is seen Fig. 1.
Embodiment 7
With embodiment 6 gained naematoloma fasciculare ligroin extraction 2.0g, last silicagel column separates.Wherein, silicagel column is a 200-300 order silica gel, wet method dress post; Eluting solvent is a hexanaphthene: ethyl acetate=7: 5.Can get monomeric compound ergosterol peroxide 94mg and ergosterol 8mg; Fusing point is respectively 177-179 ℃ and 152-155 ℃.
The fusing point of gained monomeric compound ergosterol peroxide is 177-179 ℃, white needle; Fusing point: 178 ℃; Solvability: be soluble in sherwood oil, chloroform, ethyl acetate, acetone, be slightly soluble in ethanol, methyl alcohol, water insoluble, the aceticanhydride strong sulfuric acid response positive, its spectrogram is seen accompanying drawing 2～9.
The fusing point of monomeric compound ergosterol is 152-155 ℃, white needle; Solvability: be soluble in sherwood oil, chloroform, ethyl acetate, acetone, be slightly soluble in ethanol, methyl alcohol, water insoluble, the aceticanhydride strong sulfuric acid response positive, its spectrogram is seen accompanying drawing 10～17.
Naematoloma fasciculare ligroin extraction or monomeric compound ergosterol peroxide or ergosterol or two monomeric mixture 1kg, medical starch 0.5kg, with the ethanol wet granulation of 80% concentration, whole grain, drying, dress 1# capsule, every 0.2g.Other project should meet requirement under Pharmacopoeia of People's Republic of China version capsule in 2005 item.
Naematoloma fasciculare ligroin extraction or monomeric compound ergosterol peroxide or ergosterol or two monomeric mixture 1kg, medical starch 0.5kg, dextrin 1kg, 50% concentration ethanol is an amount of, granulates, whole grain, drying, compressing tablet, every 0.2g.Other project should meet requirement under Pharmacopoeia of People's Republic of China version tablet in 2005 item.
Claims (2)
1, a kind of naematoloma fasciculare ligroin extraction obtains in order to following method:
After naematoloma fasciculare oven dry, the pulverizing, handle with 40-60 ℃ of hot methanol lixiviate earlier, quantity of methyl alcohol is 1～2 times of drug powder volume, extract repeatedly 1～3 time, merge methanol extract liquid, concentrate, add 4-6 times of distilled water again and become suspension, add the petroleum ether extraction of 1/2-1 multiple proportions example, concentrated, water-bath steaming petroleum ether solvent, promptly get extract.
2, the purposes of the described naematoloma fasciculare ligroin extraction of claim 1 in preparation medicine for treating tumor thing.
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| TWI580689B (en) * | 2012-02-02 | 2017-05-01 | 北京北大維信生物科技有限公司 | A sterol derivatives, preparation method and use thereof |
| CN102764263A (en) * | 2012-07-06 | 2012-11-07 | 广东粤微食用菌技术有限公司 | Application of 5alpha-8alpha-ergosterol peroxide-6,22(E)-diene-3beta-alcohol to preparation of anti-tumor drug |
| CN104327147B (en) * | 2014-06-04 | 2016-11-23 | 正源堂（天津滨海新区）生物科技有限公司 | A kind of ergosterol compounds and preparation method and application |
| CN104083382B (en) * | 2014-07-02 | 2016-06-08 | 内蒙古大学 | Ergosterol peroxide and taxol are killing and wounding the synergy in Hela cancer cells and application thereof |
| CN105693804B (en) * | 2014-11-28 | 2017-08-01 | 天津耀宇生物技术有限公司 | The method and its application of ergosterol are extracted from Armillaria luteo-virens |
| CN104694401B (en) * | 2015-04-09 | 2017-09-22 | 临沂大学 | Penicillium viridicatum strain and the method that ergosterol peroxide is produced with it |
| CN105131077B (en) * | 2015-08-20 | 2016-09-14 | 广州普立森生物科技有限公司 | The method extracting peroxy-ergosterol from Ganoderma spore powder with cellular wall broken |
| CN105055428A (en) * | 2015-09-14 | 2015-11-18 | 广州普立森生物科技有限公司 | Application of peroxy-ergosterol in preparation of medicament for treating primary liver cancer |
| CN109971651B (en) * | 2017-12-27 | 2021-04-16 | 中国农业科学院烟草研究所 | Tobacco endophytic fungus and application thereof in preparation of ergosterol 5,8 peroxide |
| CN108707180A (en) * | 2018-08-08 | 2018-10-26 | 齐齐哈尔医学院 | 3 beta-hydroxy -5 α, 8 α-peroxide androstane -6- alkene -17- (isatin substitution) hydazone derivatives and preparation and application |
| CN110840900A (en) * | 2019-11-18 | 2020-02-28 | 青海民族大学 | Application of ergosterol peroxide in agaricus verticillata to CDC25 phosphoprotease |
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