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CN104402898A - Citrinin compound penicitrinol M derived from Penicillium citrinum, preparation method and application of citrinin compound penicitrinol M - Google Patents

Citrinin compound penicitrinol M derived from Penicillium citrinum, preparation method and application of citrinin compound penicitrinol M Download PDF

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Publication number
CN104402898A
CN104402898A CN201410782066.0A CN201410782066A CN104402898A CN 104402898 A CN104402898 A CN 104402898A CN 201410782066 A CN201410782066 A CN 201410782066A CN 104402898 A CN104402898 A CN 104402898A
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penicillium citrinum
citrinin
penicitrinol
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CN104402898B (en
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陈立
周彤
毕延雪
张其清
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Fuzhou University
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Fuzhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/181—Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention relates to a citrinin compound penicitrinol M derived from Penicillium citrinum, a preparation method and application of the citrinin compound penicitrinol M. The compound has the effects of inhibiting tumor cell proliferation and has antineoplastic activity. The structural formula of the citrinin compound is shown in the formula (refer to the Specification). Through performing fermental cultivation on Penicillium citrinum ((i)Penicillium citrinum (/i)) IBPT-5 to obtain a yeast and conducting separation and purification on the yeast, the compound is obtained. The experiment confirms that the compound has a better antineoplastic activity to human cervical carcinoma cell line hela, so that the citrinin compound penicitrinol M can be used for preparing cell proliferation suppressing drugs or antineoplastic drugs and used in antineoplastic researches.

Description

Citrinin compounds penicitrinol M coming from Penicillium citrinum and its preparation method and application
Technical field
The present invention relates to a kind of citrinin compounds penicitrinol M coming from Penicillium citrinum and its preparation method and application.
Background technology
Fungi is relatively high in microorganism.Fungi natural product is the important sources of active diversity and structure diversity, has developed many chemicalses with good therapeutic action.Such as, antibiotics penicillin (penicillin) series, immunosuppressor cyclosporin A (cyclosporin A), hypolipidemic mevastatin (mevastatin), lovastatin (lovastatin) and antifungal drug grisovin (griseofulvin) etc., these all illustrate that fungi is the important treasure-house of natural drug.Citrinin is a kind of famous polyketone class fungal secondary meta-bolites, is be separated to obtain from the secondary metabolite of a strain penicillium citrinum the earliest.Find in research in recent years, citrinin compounds shows gratifying antitumor, antibacterial, anti-oxidant, the biologic activity such as fouling resistance, enzyme level.
The present inventor's research is learnt, Penicillium citrinum ( penicillium citrinum) IBPT-5, (be deposited in China typical culture collection center on December 25th, 2013, address: Wuhan Wuhan University, deposit number is: CCTCC NO:M 2013713) the crude extract of tunning have good cell inhibitory effect active, then its activeconstituents is studied.Shown in research finds, citrinin compounds has anti-tumor activity, has not yet to see the report of this compound on tumor cell inhibitory effect activity, therefore market also there is not yet medicine related to this.
Summary of the invention
The object of the present invention is to provide a kind of citrinin compounds penicitrinol M coming from Penicillium citrinum and its preparation method and application.This compound has inhibition tumor cell proliferation function, has anti-tumor activity.Its structural formula is:
。
The preparation method of this compound, be by fermentation culture Penicillium citrinum ( penicillium citrinum) IBPT-5, obtain fermented product, then from fermented product, separation and purification goes out this compound, described Penicillium citrinum ( penicillium citrinum) IBPT-5, be deposited in China typical culture collection center, address on December 25th, 2013: Wuhan Wuhan University, deposit number is: CCTCC NO:M 2013713.Concrete steps are as follows:
1 fermentative production
The ordinary method of culturing micro-organisms, get Penicillium citrinum ( penicillium citrinum) IBPT-5 to be inoculated on PDA solid slant culture base and to cultivate 4 days in 28 DEG C of incubators, be then inoculated in nutrient solution, 28 DEG C of static gas wave refrigerator, after 30 days, obtain mycelium and fermented liquid; Described nutrient solution composition: every premium on currency is containing N.F,USP MANNITOL 20.0g, yeast extract paste 3.0 g, maltose 20.0 g, monosodium glutamate 10.0 g, glucose 10.0 g, KH 2pO 40.5 g, MgSO 40.3 g, NaCl 30.0 g;
The acquisition of 2 medicinal extract
With gauze by mycelium and separation of fermentative broth.By the extraction into ethyl acetate twice of fermented liquid with 2 times of volumes, extraction liquid underpressure distillation, to dry, obtains the ethyl acetate extract of fermented liquid.
The separation and purification of 3 compounds
This ethyl acetate extract is by after 100-200 order silica gel mixed sample, with sherwood oil: methylene dichloride: methyl alcohol is elutriant decompression silica gel chromatographic column gradient elution, collect the eluate of methylene dichloride, with methylene dichloride: methyl alcohol is elutriant, further by pressurized silica gel column chromatography gradient elution, obtain methylene dichloride: the eluate of methyl alcohol v/v=100:1, again by semi-preparative liquid chromatography 1010 type ODS-A, 10 × 250 mm, 5 μm: being separated flow velocity is 5 mL/min, moving phase is that 70% acetonitrile contains 0.1% TFA, obtains described compound t r7.7 min.
The present invention also protects described compound and is preparing the purposes in Cytostatic to tumor cell medicine, and this compound is preparing the purposes in antitumor drug.Described tumour cell is hela cell.
Remarkable advantage of the present invention: shown in research, this Citrinin compound is comparatively rare, described citrinin compounds has significant anti-tumor activity to Human cervical cancer cell lines hela, can be used as and prepares cytostatic thing or antitumor drug for antineoplastic research.Have not yet to see the report of this compound on tumor cell inhibitory effect activity, therefore market also there is not yet medicine related to this.
Accompanying drawing explanation
Fig. 1 is the main COSY of compound penicitrinol M, HMBC and NOE signal.
Embodiment
The chemical structure of the compound of indication in following embodiment:
。
The fermentative production of this compound of embodiment 1 and separation and purification
1 fermentative production
Produce the fermentation culture of bacterium: by the ordinary method of culturing micro-organisms, get Penicillium citrinum ( penicillium citrinum) IBPT-5 (is deposited in China typical culture collection center on December 25th, 2013, address: Wuhan Wuhan University, deposit number is: CCTCC NO:M 2013713) appropriate, be inoculated on PDA solid slant culture base and cultivate 4 days in 28 DEG C of incubators.
Get the slant culture Penicillium citrinum of 4 days ( penicillium citrinum) IBPT-5 is appropriate, be inoculated into and 400mL nutrient solution [nutrient solution composition (grams per liter): N.F,USP MANNITOL 20.0, yeast extract paste 3.0, maltose 20.0, monosodium glutamate 10.0, glucose 10.0, KH is housed 2pO 40.5, MgSO 40.3, NaCl 30.0 constant volume] 1000mL Erlenmeyer flask in, 28 DEG C of static gas wave refrigerator are after 30 days, obtain mycelium and fermented liquid.
The acquisition of 2 medicinal extract
With gauze by mycelium and separation of fermentative broth.By fermented liquid ethyl acetate 1:2 (v/v) extracting twice, extraction liquid underpressure distillation, to dry, obtains the ethyl acetate extract 32g of fermented liquid.
The separation and purification of 3 compounds
After this medicinal extract passes through 100-200 order silica gel mixed sample, with sherwood oil: methylene dichloride: methyl alcohol is elutriant decompression silica gel chromatographic column gradient elution, obtains 11 components.Component 3 (1.8 g) (eluate of methylene dichloride) with methylene dichloride: methyl alcohol is elutriant, further by pressurized silica gel column chromatography gradient elution, the subfraction 3-1 (350 mg) (methylene dichloride: the eluate of methyl alcohol v/v=100:1) obtained, again by semi-preparative liquid chromatography (1010 type ODS-A, 10 × 250 mm, 5 μm): being separated flow velocity is 5 mL/min, moving phase is that 70% acetonitrile is containing 0.1% TFA, obtain shown compound (2.8 mg t r7.7 min).
Compound as white powder, high resolution mass spectrum HRESI-MS exists m/z347.1510 places provide molecular ion peak [M – H] –, (calcd. for C 19h 23o 6, 347.1500), prompting molecular weight is 348, infers that molecular formula is C in conjunction with spectral information 19h 24o 6. 1h and 13c-NMR data are in table 1, and main COSY, HMBC and NOE signal is shown in Fig. 1.
Table 1 compound 1h and 13c-NMR data (500MHz 1h and 125MHz 13c, in CDCl 3)
The test of embodiment 2 anti tumor activity in vitro
1 laboratory sample and experimental technique
The preparation test sample of sample solution is the pure compounds of separation and purification in above-mentioned enforcement 1.Precision takes appropriate amount of sample, is mixed with the solution of desired concn with methyl alcohol, active for survey.
The succeeding transfer culture of clone and cell adopts tumor cell line, and the DMEM substratum of tumour cell containing 10% FBS, at 37 DEG C of succeeding transfer culture in the incubator passing into 5% carbonic acid gas.
Cell inhibitory effect activity test method
The tumour cell that tetrazolium (MTT) method is taken the logarithm vegetative period, is adjusted to every milliliter 2 × 10 by cell density 5individual cell, is inoculated in 96 porocyte culture plates by every hole 200 microlitre, passes into 5% CO in 37 DEG C 2incubator in cultivate 4 hours.Every hole adds 2 microliters of sample liquid or blank solutions, cultivates after 24 hours, and every hole adds MTT liquid (every milliliter of 5 milligrams of normal saline solutions of MTT) 10 microlitres, continues cultivation 4 hours, 37 DEG C, 2000 revs/min centrifugal 8 minutes, suck supernatant.Every hole adds each 100 microlitres of DMSO, and micro oscillator vibrates 15 minutes, after dissolving completely, utilizes MD company to produce SPECTRAMAX Plus type microplate reader and measures light absorption value (OD) value of every hole at 570nm place to crystallization.In same 96 orifice plate, each concentration of sample all arranges three holes, separately establishes three hole blanks and acellular zeroing hole (if medicine has color will do the acellular zeroing of relative medicine concentration).Each hole OD value first does corresponding acellular zeroing, then gets three hole mean OD value by IR (%)=(OD blank-OD sample)/OD blank× 100% formula calculates cell proliferation inhibition rate (IR%) under each concentration.
2. experimental result
Cell inhibitory effect active testing result
In mtt assay test, according to the Cytostatic to tumor cell rate of this compound of different concns, application SPSS16.0 software carries out data processing and calculation of half inhibitory concentration IC 50value.The results are shown in Table 2.
The inhibit activities that table 2 compound is bred human tumor cells
3. conclusion
Compound on tumor cell hela has stronger inhibited proliferation, can be used as preparation hela inhibition of cell proliferation or antineoplastic agent for antineoplastic research.

Claims (6)

1. compound .
2. the preparation method of compound as claimed in claim 1, is characterized in that: fermentation culture Penicillium citrinum ( penicillium citrinum) IBPT-5, obtain fermented product, then from fermented product, separation and purification goes out this compound, described Penicillium citrinum ( penicillium citrinum) IBPT-5, be deposited in China typical culture collection center, address on December 25th, 2013: Wuhan Wuhan University, deposit number is: CCTCC NO:M 2013713.
3. the preparation method of compound according to claim 2, is characterized in that: the concrete steps of described preparation method are as follows:
(1) fermentative production
The ordinary method of culturing micro-organisms, get Penicillium citrinum ( penicillium citrinum) IBPT-5 to be inoculated on PDA solid slant culture base and to cultivate 4 days in 28 DEG C of incubators, be then inoculated in nutrient solution, 28 DEG C of static gas wave refrigerator, after 30 days, obtain mycelium and fermented liquid; Described nutrient solution composition: every premium on currency is containing N.F,USP MANNITOL 20.0g, yeast extract paste 3.0 g, maltose 20.0 g, monosodium glutamate 10.0 g, glucose 10.0 g, KH 2pO 40.5 g, MgSO 40.3 g, NaCl 30.0 g;
(2) acquisition of medicinal extract
With gauze by mycelium and separation of fermentative broth;
By the extraction into ethyl acetate twice of fermented liquid with 2 times of volumes, extraction liquid underpressure distillation, to dry, obtains the ethyl acetate extract of fermented liquid;
(3) separation and purification of compound
This ethyl acetate extract is by after 100-200 order silica gel mixed sample, with sherwood oil: methylene dichloride: methyl alcohol is elutriant decompression silica gel chromatographic column gradient elution, collect the eluate of methylene dichloride, with methylene dichloride: methyl alcohol is elutriant, further by pressurized silica gel column chromatography gradient elution, obtain methylene dichloride: the eluate of methyl alcohol v/v=100:1, again by semi-preparative liquid chromatography 1010 type ODS-A, 10 × 250 mm, 5 μm: being separated flow velocity is 5 mL/min, moving phase is that 70% acetonitrile contains 0.1% TFA, obtains described compound t r7.7 min.
4. compound according to claim 1 is preparing the purposes in Cytostatic to tumor cell medicine.
5. compound according to claim 1 is preparing the purposes in antitumor drug.
6. purposes according to claim 4, is characterized in that: described tumour cell is hela cell.
CN201410782066.0A 2014-12-18 2014-12-18 Citrinin compounds penicitrinol M coming from Aspergillus citrimum and its preparation method and application Expired - Fee Related CN104402898B (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107325085A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D preparation methods and its application in terms of lymph cancer
CN107325087A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D and its application in terms of malignant mela noma
CN107325081A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D preparation methods and its application in terms of lung cancer
CN107325088A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D preparation methods and the application in terms of nasopharyngeal carcinoma
CN107325086A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D preparation methods and its application in terms of colon cancer
CN115703788A (en) * 2021-08-13 2023-02-17 中国药科大学 Cinnamon streptomycin and application thereof
CN115850049A (en) * 2022-12-26 2023-03-28 中国海洋大学 Separation method and application of terpenoid with anti-tumor activity
CN116199695A (en) * 2022-08-30 2023-06-02 浙江大学 Citrinin derivative, and preparation method and application thereof

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107325087B (en) * 2016-05-27 2019-07-09 福州大学 Citrinin compounds dicitrinone D and its application in terms of malignant mela noma
CN107325081B (en) * 2016-05-27 2019-07-09 福州大学 Citrinin compounds dicitrinone D preparation method and its application in terms of lung cancer
CN107325081A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D preparation methods and its application in terms of lung cancer
CN107325088A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D preparation methods and the application in terms of nasopharyngeal carcinoma
CN107325085A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D preparation methods and its application in terms of lymph cancer
CN107325085B (en) * 2016-05-27 2019-07-09 福州大学 Citrinin compounds dicitrinone D preparation method and its application in terms of lymph cancer
CN107325087A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D and its application in terms of malignant mela noma
CN107325088B (en) * 2016-05-27 2019-07-09 福州大学 Citrinin compounds dicitrinone D preparation method and the application in terms of nasopharyngeal carcinoma
CN107325086A (en) * 2016-05-27 2017-11-07 福州大学 Citrinin compounds dicitrinone D preparation methods and its application in terms of colon cancer
CN107325086B (en) * 2016-05-27 2019-07-09 福州大学 Citrinin compounds dicitrinone D preparation method and its application in terms of colon cancer
CN115703788A (en) * 2021-08-13 2023-02-17 中国药科大学 Cinnamon streptomycin and application thereof
CN115703788B (en) * 2021-08-13 2023-12-08 中国药科大学 Cinnamyl streptomycin and application thereof
CN116199695A (en) * 2022-08-30 2023-06-02 浙江大学 Citrinin derivative, and preparation method and application thereof
CN116199695B (en) * 2022-08-30 2024-05-28 浙江大学 Citrinin derivative, and preparation method and application thereof
CN115850049A (en) * 2022-12-26 2023-03-28 中国海洋大学 Separation method and application of terpenoid with anti-tumor activity
CN115850049B (en) * 2022-12-26 2024-02-13 中国海洋大学 Separation method of terpenoid with anti-tumor activity and application thereof

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