CN106727456B - A kind of chloro quinone is preparing the application in antibacterial agent or anti-tumor drug - Google Patents

A kind of chloro quinone is preparing the application in antibacterial agent or anti-tumor drug Download PDF

Info

Publication number
CN106727456B
CN106727456B CN201611089716.9A CN201611089716A CN106727456B CN 106727456 B CN106727456 B CN 106727456B CN 201611089716 A CN201611089716 A CN 201611089716A CN 106727456 B CN106727456 B CN 106727456B
Authority
CN
China
Prior art keywords
culture
chloro
quinone
aspergillus fumigatus
antibacterial agent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201611089716.9A
Other languages
Chinese (zh)
Other versions
CN106727456A (en
Inventor
章华伟
朱双双
王鸿
董梦连
赵自平
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Zhejiang University of Technology ZJUT
Original Assignee
Zhejiang University of Technology ZJUT
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zhejiang University of Technology ZJUT filed Critical Zhejiang University of Technology ZJUT
Priority to CN201611089716.9A priority Critical patent/CN106727456B/en
Publication of CN106727456A publication Critical patent/CN106727456A/en
Application granted granted Critical
Publication of CN106727456B publication Critical patent/CN106727456B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • 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
    • C12P15/00—Preparation of compounds containing at least three condensed carbocyclic rings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Biotechnology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention discloses a kind of chloro quinones to prepare the application in antibacterial agent or anti-tumor drug, chloro quinone of the invention has very strong inhibiting effect to Escherichia coli (Escherichia coli) and Candida albicans (Candida albicans), it can be used as new antibiotic, be expected to be applied to the drug of preparation treatment Escherichia coli or the microbial related disease of Candida albicans；The chloro quinone has significant inhibiting effect to Human Lung Cancer tumour cell A549, is expected to be applied to the drug of preparation treatment Human Lung Cancer.Chloro quinone of the invention is produced from aspergillus fumigatus SPS-02 liquid fermentation, and operating procedure is simple, and the period is short, and at low cost, source is guaranteed；The present invention is synthesized using bioanalysis, no pollution to the environment.

Description

A kind of chloro quinone is preparing the application in antibacterial agent or anti-tumor drug
(1) technical field
The present invention relates to a kind of quinone derivative and metabolism bacterial strain, in particular to a kind of chloro quinone and its biological preparation side Method and purposes.
(2) background technique
Quinone (perylenequinone, PQ) is a kind of phytochrome being distributed in nature biotechnology.It sends out in recent years Existing, they have the function of good photosensitive killing tumor cell and inhibit AIDS virus, and PQ compound or novel light Electric transition material, as a kind of emerging photosensitive activity pesticide by the attention of scientific workers.
Endophyte of plant is the microorganism in a kind of special border, lives between health plant histocyte or in tissue, does not have Cause any obvious Disease symptoms of host plant, is endophytic normal flora.A large number of studies show that endophyte of plant is distributed Extensively, type is more, has important physiology and Ecology Action.Endophyte of plant has Chemical Diversity abundant, being capable of metabolic chemistry Unique structure, the significant substance of activity.Up to the present, there is not yet from aspergillus fumigatus (Aspergillus fumigatusus) The report of metabolite discovery chloro quinone.
(3) summary of the invention
It is an object of the present invention to provide a kind of chloro quinone and biological preparation method and applications, and the chloro quinone is for the first time from cigarette song Mould discovery solves and carrys out source problem, and preparation method is simple, efficient, can be used in preparing antibacterial agent or anti-tumor drug.
The technical solution adopted by the present invention is that:
The present invention provides a kind of shown chlorine for deriving from aspergillus fumigatus (Aspergillus fumigatus) SPS-02 of formula (I) The application in antibacterial agent or anti-tumor drug is being prepared for quinone,
Further, the preferably described antibacterial agent is Candida albicans (Candida albicans) antibacterial agent or Escherichia coli (Escherichia coli) antibacterial agent.Chloro quinone is to the effective concentration of Candida albicans (Candida albicans) 1.56 μM, chloro quinone is 0.78 μM to the effective concentration of Escherichia coli (Escherichia coli).
Further, the preferably described anti-tumor drug is the active drug of anti-lung cancer cell A549.Chloro quinone is to anti-lung cancer The IC of cell A54950Value is 12.79 μM.
The present invention also provides a kind of preparation method of chloro quinone, the methods are as follows: by aspergillus fumigatus The filtering fermentation liquor or centrifugation that the fermented culture of (Aspergillus fumigatus) SPS-02 obtains, take filtrate or supernatant It is extracted with ethyl acetate, organic layer is taken to be concentrated into no liquid outflow, the inverted high performance liquid chromatography separation purifying of concentrate is collected 11st minute peak removes solvent, obtains the chloro quinone.
Further, the purification condition are as follows: liquid phase instrument UV-VIS, detector are Shimadzu SPD-10AV, efficient liquid Phase infusion pump is Shimadzu LC-10AD；Chromatographic condition: C18250 × 4.6mm of chromatographic column, flow velocity 1.0mL/min, 30 DEG C of column temperature, detection Wavelength 256nm；Flow the distilled water of phase composition volume ratio 7:3: acetonitrile.
Further, the fermentation liquid is prepared as follows:
(1) inclined-plane culture: being seeded to slant medium for aspergillus fumigatus (Aspergillus fumigatus) SPS-02, and 30 DEG C moisturizing culture 3-5 days, obtain thallus inclined-plane；The slant medium final concentration composition are as follows: sodium chloride 70g/L, sucrose 20g/ L, potato 200g/L, solvent are distilled water, and pH is natural；
(2) seed culture: being seeded to Czapek seed culture medium with high salt from one oese thallus of thallus inclined-plane picking, 200rpm, shaking table culture 3-4 days under the conditions of 30 DEG C, seed liquor is obtained；The Czapek seed culture medium final concentration composition with high salt Are as follows: sucrose 30g/L, dipotassium hydrogen phosphate 1g/L, sodium nitrate 2g/L, magnesium sulfate 0.5g/L, potassium chloride 0.5g/L, ferrous sulfate 0.01g/L, sodium chloride 70g/L, solvent are distilled water, and pH is natural；
(3) seed liquor that step (2) obtain fermented and cultured: is seeded to fermented and cultured with the inoculum concentration of volume ratio 1:10 Base obtains fermentation liquid shaking table culture 9-10 days under the conditions of 200rpm, 30 DEG C, and fermentation medium final concentration is formed with high salt Czapek seed culture medium.
Aspergillus fumigatus (Aspergillus fumigatus) SPS-02 of the present invention is preserved in Chinese Typical Representative culture guarantor Hiding center, the deposit date is on January 13rd, 2013, deposit number was CCTCC No:M2013014, and address: China, Wuhan are military Chinese university, postcode 430072 disclose in patent application CN103113376A.
Compared with prior art, the beneficial effects are mainly reflected as follows:
(1) present invention provides a kind of method for producing chloro quinone using aspergillus fumigatus SPS-02；
(2) chloro quinone (I) of the invention is to Escherichia coli (Escherichia coli) and Candida albicans (Candida albicans) has very strong inhibiting effect, can be used as new antibiotic, is expected to be applied to preparation treatment large intestine bar The drug of bacterium or the microbial related disease of Candida albicans；
(3) the invention further relates to the chloro quinones (I) to have significant inhibiting effect to Human Lung Cancer tumour cell A549, It is expected to be applied to the drug of preparation treatment Human Lung Cancer.
(4) chloro quinone (I) of the invention is produced from aspergillus fumigatus SPS-02 liquid fermentation, and operating procedure is simple, week Phase is short, at low cost, and source is guaranteed；
(5) present invention is synthesized using bioanalysis, no pollution to the environment.
(4) specific embodiment
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in This:
Embodiment 1: the preparation of aspergillus fumigatus SPS-02 fermentation culture
(1) inclined-plane culture: being seeded to slant medium for aspergillus fumigatus SPS-02,30 DEG C incubator moisturizing culture 3-5 days, obtain Obtain thallus inclined-plane；Slant medium final concentration composition are as follows: sodium chloride 70g/L, sucrose 20g/L, potato 200g/L, solvent are to steam Distilled water, natural ph.
(2) seed culture: being seeded to Czapek seed culture medium with high salt from one oese thallus of thallus inclined-plane picking, 200rpm, shaking table culture 3-4 days under the conditions of 30 DEG C, seed liquor is obtained；Czapek seed culture medium final concentration composition with high salt are as follows: sugarcane Sugared 30g/L, dipotassium hydrogen phosphate 1g/L, sodium nitrate 2g/L, magnesium sulfate 0.5g/L, potassium chloride 0.5g/L, ferrous sulfate 0.01g/L, Sodium chloride 70g/L, solvent are distilled water, natural ph.
(3) seed liquor that step (2) obtain fermented and cultured: is seeded to fermented and cultured with the inoculum concentration of volume ratio 1:10 Base obtains fermentation culture, fermentation medium final concentration composition is the same as high shaking table culture 9-10 days under the conditions of 200rpm, 30 DEG C Salt Czapek seed culture medium.
Embodiment 2: the extraction of chloro quinone with separate, identify
1, the extraction of chloro quinone with separate
By 1 gained fermentation liquid of embodiment after being centrifuged, supernatant ethyl acetate (volume ratio 1:1) room temperature is taken to extract 3 times, Cryogenic vacuum is concentrated into no liquid outflow, obtains brown coarse extract F；The inverted high performance liquid chromatography of coarse extract F (RP-HPLC) point From the peak of collection the 11st minute, cryogenic vacuum removal mobile phase obtains compound I.Liquid phase instrument: UV-VIS, detector: Shimadzu SPD-10AV；Efficient liquid phase infusion pump: Shimadzu LC-10AD；Chromatographic condition: C18250 × 4.6mm of chromatographic column, flow velocity 1.0mL/ Min, 30 DEG C of column temperature, Detection wavelength 256nm；It flows phase composition distilled water (A): acetonitrile (B)=7:3 (volume ratio).
2, the Structural Identification of chloro quinone (I)
The purpose compound I of acquisition is subjected to mass spectrum (Agilent 6210LC/TOF, negative source) and nuclear magnetic resonance (Bruker Avance III Unity Plus 500MHz, in DMSO-d) spectrum measurement.
(1) mass spectrometric data are as follows: HRESI-MS m/z 385.0459 [M-H]-；Determine molecular formula C20H15O6Cl；1H and13C NMR data is shown in Table 1.
Table 1: compound (I)1H spectrum and13C modal data (500MHz, CD3SOCD3)
Note: s- is unimodal, and d- is bimodal, t- triplet.
In conclusion target product is chloro quinone, structural formula is shown in formula (I):
Wherein 1,2,3a, 4,5,6,6a, 6b, 7,8,9,9a, 9b, 10,11,12,12a, 12b, 12c are carbon atom serial number, The system of compounds is named as 8-chloro-3,6a, 7,9,10-pentahydroxy-9,8,7,6a- Tetrahydroperylen-4 (6aH)-one, i.e. 8- chloro- 3,6a, 7,9,10- penta hydroxy groups -9,8,7,6a- tetra- quinhydrones -4 (6aH) ketone.
Embodiment 3: chloro quinone bacteriostatic activity evaluation
Chloro quinone activity rating uses concentration gradient dilution method, and measurement is repeated 6 times every time, and test pathogenic bacteria include white Candida albicans (Canidia albicans ATCC10231) and coli strain (Escherichia coli ATCC25922).
The specific method is as follows:
1. testing bacterium solution preparation:
Pathogenic bacteria Candida albicans is forwarded in the triangular flask containing PDB culture solution after plate activation culture, 200rpm, shake culture 48h under the conditions of 30 ± 1 DEG C pass through and sterile PDB culture solution is added adjusts OD570To 0.2.PDB culture solution Composition are as follows: potato 200g/L, sucrose 20g/L, solvent are distilled water, natural ph.
Pathogenic bacteria Escherichia coli are forwarded in the triangular flask containing LB culture solution after plate activation culture, 200rpm, Shake culture for 24 hours, adjusts OD by the way that LB aseptic culture fluid is added under the conditions of 30 ± 1 DEG C570To 0.2.LB culture solution composition are as follows: ferment The old 10g/L of female extract 5g/L, tryptose, NaCl 10g/L, solvent are distilled water, pH7.4.
2. prepared by test sample: chloro quinone (I) being dissolved in dimethyl sulfoxide (DMSO), is matched using doubling dilution The solution of 10 concentration is made, it is respectively 100,50,25,12.5,6.25,3.13,1.56,0.78,0.39,0.20 μM, positive right According to for amphotericin B and Amoxicillin, the solution of 10 concentration, the concentration gradient of amphotericin B are prepared using doubling dilution Be 100,50,25,12.5,6.25,3.13,1.56,0.78,0.39,0.20 μM, the concentration gradient of Amoxicillin is 150,75, 37.5、18.75、9.38、4.69、2.34、1.17μM。
3. drug sensitive test: being separately added into culture solution (i.e. PDB culture solution and LB needed for indicator bacteria grows in sterile 96 orifice plate Culture solution), and it is inoculated with two plants of indicator bacterias (i.e. Candida albicans and Escherichia coli), bacterial concentration OD respectively570Value is 0.2, then It is separately added into the test sample solution of step 2 preparation, 100 μ L are added in every hole, and amphotericin B and Amoxicillin are as positive control Test sample solution is substituted, bacterium is cultivated for 24 hours at 37 ± 1 DEG C, and fungi cultivates 48h, microplate reader detection at 28 ± 1 DEG C OD value under 570nm wavelength, every group of experiment do 6 groups it is parallel, data are averaged, inhibit indicator bacteria growth minimum concentration be exactly chemical combination Minimal inhibitory concentration, that is, MIC value of object.The results are shown in Table 2.
Table 2: the antibacterial MIC value (μM) of chloro quinone (I) and positive control
Bacteriostatic activity evaluation result shows that chloro quinone (I) has than positive control medicine (amphotericin B and A Moxi Woods) stronger bacteriostasis, inhibiting the MIC value of source of people pathogenic bacteria Candida albicans and Escherichia coli is respectively 1.56,0.78 μM.
Embodiment 4: chloro quinone (I) in vitro cytotoxic effect evaluation
The evaluation of chloro quinone (I) cytotoxic activity uses concentration gradient dilution method, and measurement is repeated 5 times every time, test cell System is lung cancer cell types cell.
The specific method is as follows:
1. prepared by cell line: 1. experimental group: lung cancer cell types cell (the Tissue Culture Flask A-7- of logarithmic growth phase 1) it, is cleaned twice with PBS, with the digestion of 0.25% pancreatin, is counted, adjustment cell density is 1 × 104A/mL is inoculated in the training of 96 holes It supports in plate, every hole adds 180 μ L.2. control group: the same experimental group of inoculation step.3. blank group: every hole adds 180 μ L containing 10% tire ox blood Clear RPMI-1640 culture solution.Cultivate in 37 DEG C of constant incubators makes cell adherent for 24 hours.
2. prepared by test sample: precision weighs chloro quinone (I) 0.0013g, and 1mL DMSO is added and sufficiently dissolves, with 0.22 μm membrane filtration, be made into 3.36 μM of mother liquor.Mother liquor is taken to use the RPMI-1640 culture solution gradient containing 10% fetal calf serum dilute It releases, concentration is from low to high successively are as follows: 12.5,25.0,37.5,50.0,75.0,100.0,150.0 μM.Control is that 5-F- urine is phonetic Pyridine, DMSO are configured to consistent with sample concentration.
3. drug sensitive test: 1. experimental group: 20 μ L chloro quinone (I) gradient liquid are added in every hole, and (each gradient liquid does four respectively A parallel hole), so that its final concentration is respectively as follows: 1.25,2.50,3.75,5.00,7.50,10.00,15.00 μM.2. blank group: every The RPMI-1640 culture solution that 20 μ L contain 10% fetal calf serum is added in hole.3. positive controls: 20 μ L5-F- uracils are added in every hole Gradient liquid makes its final concentration be respectively as follows: 1.25,2.50,5.00,7.50,10.00,15.00 μM.Training in 37 DEG C of constant incubators Support 48h.After 48h, 96 orifice plates are taken out, every hole is separately added into 20 μ L MTT reagents, continues after cultivating 4h, every hole is drawn on 100 μ L 100 μ L DMSO are added in clear liquid, and concussion 10min is protected from light on shaking table, measures OD value under 570nm wavelength in microplate reader.Often Group experiment does 5 times in parallel, and data are averaged, and is computed the IC for obtaining sample and compareing (5-F- uracil)50Value.As a result such as table Shown in 3.
Table 3: chloro quinone (I) A549 cytotoxic activity
Cytotoxic activity result of study shows that chloro quinone (I) has with control drug (5-F- uracil) similar body The outer ability for inhibiting Human Lung Cancer tumour cell A549, IC50Value is 12.79 μM.

Claims (4)

1. preparing answering in antibacterial agent or anti-tumor drug from the chloro quinone of aspergillus fumigatus SPS-02 shown in a kind of formula (I) With, it is characterised in that the antibacterial agent is Candida albicans (Candida albicans) antibacterial agent or Escherichia coli (Escherichia coli) antibacterial agent, the anti-tumor drug are the active drug of anti-lung cancer cell A549；
2. application as described in claim 1, it is characterised in that the chloro quinone is prepared as follows: by aspergillus fumigatus The filtering fermentation liquor or centrifugation that the fermented culture of (Aspergillus fumigatus) SPS-02 obtains, take filtrate or supernatant It is extracted with ethyl acetate, organic layer is taken to be concentrated into no liquid outflow, the inverted high performance liquid chromatography separation purifying of concentrate is collected 11st minute peak removes solvent, obtains chloro quinone shown in the formula (I).
3. application as claimed in claim 2, it is characterised in that the purification condition are as follows: liquid phase instrument UV-VIS, detection Device is Shimadzu SPD-10AV, and efficient liquid phase infusion pump is Shimadzu LC-10AD；Chromatographic condition: C18250 × 4.6mm of chromatographic column, flow velocity 1.0mL/min, 30 DEG C of column temperature, Detection wavelength 256nm；Flow the distilled water of phase composition volume ratio 7:3: acetonitrile.
4. application as claimed in claim 2, it is characterised in that the fermentation liquid is prepared as follows:
(1) aspergillus fumigatus (Aspergillus fumigatus) SPS-02 inclined-plane culture: is seeded to slant medium, 30 DEG C of guarantors Wet culture 3-5 days obtains thallus inclined-plane；The slant medium final concentration composition are as follows: sodium chloride 70g/L, sucrose 20g/L, horse Bell potato 200g/L, solvent are distilled water, and pH is natural；
(2) seed culture: being seeded to Czapek seed culture medium with high salt from one oese thallus of thallus inclined-plane picking, 200rpm, shaking table culture 3-4 days under the conditions of 30 DEG C, seed liquor is obtained；The Czapek seed culture medium final concentration composition with high salt Are as follows: sucrose 30g/L, dipotassium hydrogen phosphate 1g/L, sodium nitrate 2g/L, magnesium sulfate 0.5g/L, potassium chloride 0.5g/L, ferrous sulfate 0.01g/L, sodium chloride 70g/L, solvent are distilled water, and pH is natural；
(3) fermented and cultured: being seeded to fermentation medium for the seed liquor that step (2) obtain with the inoculum concentration of volume ratio 1:10, 200rpm, shaking table culture 9-10 days under the conditions of 30 DEG C, fermentation liquid is obtained, fermentation medium final concentration is formed with Czapek kind with high salt Sub- culture medium.
CN201611089716.9A 2016-12-01 2016-12-01 A kind of chloro quinone is preparing the application in antibacterial agent or anti-tumor drug Active CN106727456B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201611089716.9A CN106727456B (en) 2016-12-01 2016-12-01 A kind of chloro quinone is preparing the application in antibacterial agent or anti-tumor drug

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201611089716.9A CN106727456B (en) 2016-12-01 2016-12-01 A kind of chloro quinone is preparing the application in antibacterial agent or anti-tumor drug

Publications (2)

Publication Number Publication Date
CN106727456A CN106727456A (en) 2017-05-31
CN106727456B true CN106727456B (en) 2019-04-09

Family

ID=58915368

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201611089716.9A Active CN106727456B (en) 2016-12-01 2016-12-01 A kind of chloro quinone is preparing the application in antibacterial agent or anti-tumor drug

Country Status (1)

Country Link
CN (1) CN106727456B (en)

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
A new perylenequinone from a halotolerant fungus, Alternaria sp M6;Zhang SY等;《Chinese Journal of Natural Medicines》;20120131;第10卷(第1期);第68-71页 *
Hypocrellin D, a cytotoxic fungal pigment from fruiting bodies of the ascomycete Shiraia bambusicola;Fang LZ等;《Journal of Antibiotics》;20060630;第59卷(第6期);第351-354页 *
Photodynamic antimicrobial activity of hypocrellin A;Su YJ等;《Journal of Photochemistry and Photobiology B: Biology》;20110119;第103卷(第1期);第29-34页 *

Also Published As

Publication number Publication date
CN106727456A (en) 2017-05-31

Similar Documents

Publication Publication Date Title
CN107298671A (en) Come from the secalonic acid H of penicillium oxalicum and prepare the application of anti-human colon cancer drug
CN106434783B (en) A kind of chromone compound and preparation method thereof and the application in preparation antibacterials
CN107298672B (en) Application of seclenic acid I derived from penicillium oxalicum in preparation of anti-human colon cancer drugs
CN103880808B (en) A kind of xanthone compounds and application thereof
CN104877910B (en) A kind of plant endogenesis epiphyte mine-laying penicillium bacterium F4a and its application
CN103255061B (en) Penicillium griseofulvum, antibacterial active compound generated thereby and application
CN109232493A (en) A kind of sesquiterpenoid and its preparation method and application
CN108315264A (en) A kind of polyketide in sea paint endogenetic fungus source and its application in preparing anti-inflammatory drug
CN100494189C (en) Benzofurantone compound, its production and use
CN101628931B (en) Antitumor antibiotics, pharmaceutically acceptable salts thereof, preparation method thereof and use thereof
CN107298670A (en) Come from penicillium oxalicum secalonic acid H and prepare anti-human oral cavity epidermoid carcinoma medicinal application
CN106727456B (en) A kind of chloro quinone is preparing the application in antibacterial agent or anti-tumor drug
CN107603922B (en) The methods and applications of sponge symbiotic streptomycete and its fermenting and producing staurosporin
CN104804020B (en) Sulfodionepiperazine compound, and preparation method and use thereof
CN110357788A (en) A kind of polyketides and its preparation method and application
KR100398677B1 (en) Cultivation Method of mushroom mycelium using citrus juice and mushroom mycelium thereof
CN109134416A (en) Secalonic acid H derived from penicillium oxalicum is in the application for preparing human cervical cancer 1 cancer drug
CN107226800A (en) A kind of xanthone classes compound and its preparation method of monocrystalline and the application as anti-Mycobacterium marinum medicine
CN102070598B (en) Norsesquiterpenoid peroxides and preparation method thereof
CN103058846B (en) Benzoquinone derivative from aspergillus aculeatus and application of benzoquinone derivative
CN108794502A (en) A kind of trichothecene compounds and its preparation method and application
CN104211670A (en) Alkyl pyranone compound and preparation process and application
CN104447475B (en) Preparation method and application of penicillenol D1 derived from penicillium citrinum
CN113402453B (en) Pyridone piericin, preparation method thereof and application thereof in preparation of anti-cancer drugs
CN104211780A (en) Cyclic depsipeptides compound, preparation method and purpose thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20170531

Assignee: QINGYUAN ZUISANGONG WINE INDUSTRY Co.,Ltd.

Assignor: JIANG University OF TECHNOLOGY

Contract record no.: X2023980037301

Denomination of invention: Application of a chloroperylene quinone in the preparation of antibacterial or anti-tumor drugs

Granted publication date: 20190409

License type: Common License

Record date: 20230703

EE01 Entry into force of recordation of patent licensing contract