CN103910746B - The Berkeleyones compound in one class marine fungi source and its preparation method and application - Google Patents
The Berkeleyones compound in one class marine fungi source and its preparation method and application Download PDFInfo
- Publication number
- CN103910746B CN103910746B CN201410072112.8A CN201410072112A CN103910746B CN 103910746 B CN103910746 B CN 103910746B CN 201410072112 A CN201410072112 A CN 201410072112A CN 103910746 B CN103910746 B CN 103910746B
- Authority
- CN
- China
- Prior art keywords
- compound
- berkeleyones
- methanol
- formula
- ethyl acetate
- 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.)
- Expired - Fee Related
Links
Classifications
-
- 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
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- 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
Abstract
The invention belongs to medical compounds technical field, be specifically related to the Berkeleyones compound in a kind of marine fungi source and its preparation method and application.As shown in the formula (I), this noval chemical compound has the effect of anticancer propagation to the structure of described Berkeleyones compound, can be used for preparing cancer therapy drug.Berkeleyones compound of the present invention is from a kind of marine fungi sclerotium penicillium sp<i>penicillium sclerotiorum</i>.SJ isolated in 0167, Marine Microbial Kinds is various, substantial amounts, and the method extracted from microorganism is simple, and step is easy so that Berkeleyones compound abundance, with low cost；High to cancer cell suppression activity, have a extensive future.。
Description
Technical field
The invention belongs to medical compounds technical field, be specifically related to the Berkeleyones compound in a class marine fungi source and its preparation method and application.
Background technology
Rhizophora apiculata Blume is distinctive evergreen shrubs and dungarunga group on the torrid zone, bay, subtropical zone, estuary mud bar, has pneumathodium or prop root, the Intertidal zone being typically distributed about between high-water mark and subtidal line.In China, Rhizophora apiculata Blume is mainly distributed on Hainan Island, Guangxi, Guangdong and Fujian.As the second largest monoid in marine fungi, mangrove fungi is unique due to growth conditions, and active metabolite is the abundantest, has great significance in terms of marine resources development.Isolating at present a lot of novel structure scientist's various endogenous fungus metabolites inside it, have the compound of remarkable activity, many has been enter into clinical experimental stage.
Berkeleyones compound is originally derived from the penicillium separated from the mine lake of Berkeley, this bacterial strain still can be survived under rugged environment, its metabolite is likely to have active substance, therefore research worker conducts in-depth research and is found that the Berkeleyones compound of new construction, and think that this compounds plays an important role (DonaldB.Stierle, etal.Org.Lett., 2004 in fungus body, 6,1049-1052).Only 15 (DonaldB.Stierle, etal.J.Nat.Prod., the 2007,70,1820-1823 that the compound of this class formation has been reported at present;DonaldB.Stierle,etal.J.Nat.Prod.,2011,74,2273-2277;Motoolida,etal.Org.Lett.,2008,10,845-848;YiZhang, etal.J.Nat.Prod., 2012,75,1888-1895).
Cancer is commonly encountered diseases and the frequently-occurring disease of serious threat human life.The important directions that research and development are efficient, the new type anticancer medicine of low toxicity, high specificity is the research of current antitumor drug.Marine natural products is as one of the important sources of lead compound, and the research and development to newtype drug have important effect.
Summary of the invention
It is an object of the invention to provide the Berkeleyones compound in the new marine fungi source of a class.Described Berkeleyones compound is isolated from a kind of South Sea mangrove endophytic fungus sclerotium penicillium sp Penicilliumsclerotiorum.SJ0167, this compound all shows preferable active anticancer to breast cancer cell (MDA-MB-435), hepatoma carcinoma cell (HepG2), colon cancer cell (HCT-116) and lung adenocarcinoma cell (A549), can be applicable to prepare cancer therapy drug.
It is a further object to provide the preparation method of above-mentioned Berkeleyones compound.
It is a still further object of the present invention to provide the application of above-mentioned Berkeleyones compound.
The above-mentioned purpose of the present invention is achieved by following technical solution:
One class Berkeleyones compound, its structural formula as shown in the formula (I):
。
Fungi sclerotium penicillium sp Penicilliumsclerotiorum.SJ0167 used by the present invention is isolated a kind of endogenetic fungus in the Rhizophora apiculata Blume of the South Sea, Classification And Nomenclature is sclerotium penicillium sp Penicilliumsclerotiorum, this bacterial strain is in China Committee for Culture Collection of Microorganisms's common micro-organisms center (CGMCC) preservation, preservation date is December in 2013 23, and preserving number is CGMCCNO:8628；Depositary institution address is: Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3 Institute of Microorganism, Academia Sinica.
The preparation method of above-mentioned Berkeleyones compound, comprises the steps:
S1. fungus Penicilliumsclerotiorum.SJ0167 bacterial strain accesses seed culture medium, and shaking table is cultivated, and obtains seed culture fluid；
S2. accessing in fermentation medium by seed culture fluid, quiescent culture obtains fermented product；
S3., fermented product is used methanol soak extraction, and methanol extract liquid extracts through ethyl acetate after concentrating, concentrates, and obtains extractum, then through chromatography, obtains Berkeleyones compound shown in formula (I) 1 and compound 2.
Seed culture medium described in step S1 uses the GYT culture medium that this area is conventional, incubated at room temperature 5 ~ 7 days；The composition of conventional GYT culture medium is by weight: glucose 18 ~ 23g, peptone 4 ~ 5g, yeast extract 1 ~ 2g, sea salt 55 ~ 65g, water 1.5 ~ 2L.It is under room temperature that shaking table described in step S1 is cultivated, and shaking speed 100 ~ 150rpm, incubation time is 5 ~ 7 days.
As a kind of preferred version, in above-mentioned preparation method, fermentation medium described in step S2 is solid rice medium, and its component is: rice 50 ~ 70g, sea salt 1.5 ~ 2g, water 50 ~ 70mL.The time of quiescent culture described in step S2 is 1 ~ 2 month, and the temperature of quiescent culture is room temperature.
As a kind of preferred version, in above-mentioned preparation method, the consumption of methanol described in step S3 is and fermented product equal-volume, and the consumption of ethyl acetate is the 1/3 of methanol usage；Described extractum silicagel column carries out chromatography, uses the petroleum ether-ethyl acetate gradient elution of 10:0,9:1,8:2,7:3,6:4,5:5,4:6,3:7,2:8,1:9 and 0:10 when silicagel column carries out chromatography respectively.The petroleum ether-ethyl acetate elution fraction of 7:3,6:4 and 5:5 is merged, chromatograph through polydextran gel SephadexLH-20, it is the further eluting of eluant with petroleum ether-methylene chloride-methanol that volume ratio is 2:1:1, again through HPLC, it is eluent with the methanol-water that volume ratio is 6:4, obtains compound 1 shown in formula (I) and compound 2.
Described silicagel column is the silicagel column that this area is conventional, and mesh number is about 200 ~ 300 mesh.
The Berkeleyones compound of isolated of the present invention has the effect of anticancer propagation, therefore can be used for preparing cancer therapy drug.
Described anticancer include anti-breast cancer, anti-liver cancer and anti-, inhibitor against colon carcinoma cells or Antilung gland cancer.
There is advantages that
The new skeleton Berkeleyones compound of the present invention is isolated from a kind of marine fungi, and Marine Microbial Kinds is various, substantial amounts, the method extracting compound from microorganism is simple, step is easy so that Berkeleyones compound abundance, with low cost；Described new skeleton Berkeleyones compound has the effect of anticancer propagation, can be used for preparing cancer therapy drug, has a extensive future.
Accompanying drawing explanation
Fig. 1 is the proton nmr spectra of Berkeleyones compound 1 of the present invention.
Fig. 2 is the carbon-13 nmr spectra of Berkeleyones compound 1 of the present invention.
Fig. 3 is nuclear magnetic resonance, NMR H, the H-cosy two-dimensional spectrum of Berkeleyones compound 1 of the present invention.
Fig. 4 is the nuclear magnetic resonance, NMR HSQC two-dimensional spectrum of Berkeleyones compound 1 of the present invention.
Fig. 5 is the nuclear magnetic resonance, NMR HMBC two-dimensional spectrum of Berkeleyones compound 1 of the present invention.
Fig. 6 is the nuclear magnetic resonance, NMR NOE two-dimensional spectrum of Berkeleyones compound 1 of the present invention.
Fig. 7 is the proton nmr spectra of Berkeleyones compound 2 of the present invention.
Fig. 8 is the carbon-13 nmr spectra of Berkeleyones compound 2 of the present invention.
Fig. 9 is nuclear magnetic resonance, NMR H, the H-cosy two-dimensional spectrum of Berkeleyones compound 2 of the present invention.
Figure 10 is the nuclear magnetic resonance, NMR HSQC two-dimensional spectrum of Berkeleyones compound 2 of the present invention.
Figure 11 is the nuclear magnetic resonance, NMR HMBC two-dimensional spectrum of Berkeleyones compound 2 of the present invention.
Figure 12 is the nuclear magnetic resonance, NMR NOE two-dimensional spectrum of Berkeleyones compound 2 of the present invention.
Detailed description of the invention
Below in conjunction with Figure of description and specific embodiment, the present invention is further explained, but embodiments of the present invention is not limited in any way.Unless stated otherwise, involved in embodiment reagent, method are reagent commonly used in the art and method.
The extraction of embodiment 1 compound and sign
The compound of the present invention, can from the mangrove endophytic fungus sclerotium penicillium sp Penicilliumsclerotiorum.SJ0167 of the South Sea isolated, marine fungi sclerotium penicillium sp Penicilliumsclerotiorum.SJ0167 is isolated from the Hai Sang of Shenzhen.This bacterial strain is in China Committee for Culture Collection of Microorganisms's common micro-organisms center (CGMCC) preservation, preservation date is December in 2013 23, preserving number is CGMCCNO:8628, and depositary institution address is: Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3 Institute of Microorganism, Academia Sinica.
The concrete preparation process of compound is as follows:
S1. the acquisition of seed culture fluid:
S11. seed culture medium is prepared: glucose 20g, peptone 4g, yeast extract 2g, sea salt 60g, tap water 2000mL, average mark is loaded on 8 500mL conical flasks, and 121 DEG C go out 25 minutes.
S12. the cultivation of seed: the bacterial strain of marine fungi Penicilliumsclerotiorum.SJ0167 is accessed seed culture medium, at a temperature of 28 DEG C, puts the rotating speed with 120rpm on shaking table, cultivates 72 hours to obtain seed culture fluid.
S2. fermentation culture: 1000mL triangular flask built-in 60g rice, 2g sea salt, 60mL water, seed culture fluid 5mL step S1 obtained under superclean bench sterile working after 121 DEG C of (0.1MPa) high temperature sterilize 25min accesses equipped with in the conical flask of fermentation medium, inoculation 90 bottles altogether, obtains fermented product in 30 days in room temperature quiescent culture.
The extraction of S3.Berkeleyones compound separates: by cultured for step S2 fermented product with every bottle of 150mL methanol extraction three times, obtain methanolic extract；Methanolic extract is through being concentrated to give concentrate, and concentrate ethyl acetate carries out extracting 3 times, and each consumption is 50mL every bottle, is concentrated to give crude extract extractum 67g.This crude extract extractum silicagel column of 200 ~ 300 mesh carries out chromatography, is specially respectively with the petroleum ether-ethyl acetate gradient elution of 10:0,9:1,8:2,7:3,6:4,5:5,4:6,3:7,2:8,1:9 and 0:10.The petroleum ether-ethyl acetate elution fraction of 7:3,6:4 and 5:5 is merged, chromatograph through polydextran gel SephadexLH-20, it is the further eluting of eluant with petroleum ether-methylene chloride-methanol that volume ratio is 2:1:1, again through HPLC, it is eluent with the methanol-water that volume ratio is 6:4, obtains formula (I) Berkeleyones compound 1(20mg) and 2(10mg).
The compound 1 of separation and Extraction is white solid, and it is carried out the spectrogram of nuclear magnetic resonance spectroscopy detection as shown in Fig. 1 ~ 6.
The physicochemical property data of compound 1 structural analysis test are as follows:
ESIMSm/z489.2[M+H]+,487.2[M-H]-,HRESIMSm/z488.2048(calcdforC26H32O9488.2041)。1HNMR(500MHz,CDCl3)δ6.50(s,1H),6.11(s,1H),5.85(s,1H),5.53(d,J=7.5Hz,1H),4.54(s,1H),3.82(s,3H),3.63(q,J=6.1Hz,1H),3.03(d,J=7.6Hz,1H),2.79(m,1H),1.79(d,J=12.5Hz,1H),1.71(d,J=13.2Hz,1H),1.65(d,J=12.7Hz,1H),1.63(s,3H),1.48(s,6H),1.35(d,J=6.1Hz,3H),1.16(d,J=7.6Hz,3H),0.99(s,3H)；13CNMR(126MHz,CDCl3)δ180.3(C),175.3(C),163.3(C),157.6(C),134.7(C),129.5(CH),120.5(CH),102.7(C),99.0(CH),82.2(C),80.7(CH),77.6(CH),61.0(C),52.7(CH3),49.1(C),46.6(C),45.0(CH),43.7(CH),43.4(CH),34.70(CH2),27.2(CH3),26.6(CH3),26.1(CH3),18.6(CH3),17.4(CH3),13.6(CH3)。
The compound 2 of separation and Extraction is white solid, and it is carried out the spectrogram of nuclear magnetic resonance spectroscopy detection as shown in Fig. 7 ~ 12.
The physicochemical property data of compound 2 structural analysis test are as follows:
ESIMSm/z489.2[M+H]+,487.1[M-H]-,HRESIMSm/z488.2048(calcdforC26H32O9488.2041)。1HNMR(500MHz,CDCl3)δ5.91(d,J=7.2Hz,1H),5.85(s,1H),4.24(dd,J=10.2,6.2Hz,1H),3.90(s,3H),3.78(q,J=6.2Hz,1H),3.36(dt,J=19.8,2.7Hz,1H),3.06(d,J=2.4Hz,1H),3.04(d,J=9.8Hz,1H),2.99(d,J=14.6Hz,1H),2.85(d,J=19.1Hz,1H),2.44(d,J=6.8Hz,1H),2.40(d,J=8.7Hz,1H),1.91(s,3H),1.52(s,3H),1.50(s,3H),1.46(s,3H),1.42(d,J=6.2Hz,3H),1.16(s,3H)；13CNMR(126MHz,CDCl3)δ177.4(C),175.0(C),170.6(C),134.8(C),132.5(C),128.3(C),126.1(C),100.7(C),98.4(CH),84.3(C),79.4(CH),73.2(CH),62.1(C),53.3(CH3),50.5(C),46.2(C),44.8(CH),35.0(CH2),34.1(CH2),34.0(CH2),26.8(CH3),26.3(CH3),26.2(CH3),19.1(CH3),14.9(CH3),13.7(CH3)。
The molecular formula that can determine that compound 1 from the structural analysis testing result of nuclear magnetic resonance, NMR is C26H32O9, the molecular formula of compound 2 is C26H32O9, structural formula as shown in the formula (I):
。
The active anticancer test of embodiment 2 compound
The active anticancer test of compound uses mtt assay (T.Mosmann.Rapidcolorimetricassayforcellulargrowthandsurv ival:applicationtoproliferationandcytotoxicityassays.Jou rnalofimmunologicalmethods.JournalofImmunologicalMethods 1983,65,55-63.).
(1) material
Four Cuo salt (MTT): dissolve MTT (3-4,5-dimethythiazol-z-yl) 2,5-diphenytetrazoliumbromide with the phosphate buffer (PBS) of 0.01mol/L, SIGMA), ultimate density 5mg/ml, filtration sterilization, after subpackage, 4 DEG C keep in Dark Place.
The dodecyl sodium sulfate of the preparation of MTT lysate: 80g is dissolved in the N-N-dimethylformamide of 200ml, heating in water bath hydrotropy, adds 200ml distilled water, mixes with 1N hydrochloric acid (1:1) with 80% acetic acid and adjusts pH to 4.7.
Cell strain is selected: MDA-MB-435, HepG2, HCT-116, A549 tumor cell line.The CO of 5% at 37 DEG C2Preservation in the air of content.
(2) operating procedure
The above four kinds of tumor cells being in exponential phase are inoculated in 96 orifice plates respectively, with Dulbecco ' smodifiedEagle ' smedium (DMEM) complete medium, cell are diluted to 1 × 104Individual/ml, every hole adds the cell that 200 μ L have diluted, and often five Duplicate Samples of group, separately set blank well and control wells, and described blank well is the hole of non-inoculating cell, and described control wells is the culture fluid of not drug containing.At 5%CO2In, cultivate 24 hours under 37 DEG C of room temperatures and saturated humidity.Remove culture medium, (compound method of the cancer therapy drug solution of described variable concentrations prepares mother liquid medicine for first dissolving medicine with a small amount of DMSO to the cancer therapy drug solution of addition variable concentrations, with DMEM complete medium, mother liquid medicine is diluted to medicine final concentration of 0 again, 0.1, 0.5, 1, 5, 10, 20, 30, 40, the solution of the Azaphilone class dimer compound of the present invention of 50 μMs, in drug solution after dilution, the percent by volume of DMSO is not higher than the 0.1% of cumulative volume), every hole 200 μ L, cultivate 48 hours, every hole adds the MTT(Sigma of 2mg/ml) 20 μ L, hatch 4 hours.Culture fluid in sucking-off hole the most completely, adds DMSO liquid (150 μ L/ hole), vibrates 10 minutes, make crystal fully dissolve.Under 570nm wavelength, each hole OD value is measured by microplate reader；With absorbance, drug level logarithm is mapped, obtain IC50Value, result meansigma methods ± standard deviation represents.
Compound of the present invention carries out all showing the inhibitory action to cancerous cell in 4 kinds of tumor cell viability tests, and test result is as shown in table 1 below.
Table 1
| IC50 (μg/mL) | Breast carcinoma MDA-MB-435 | Hepatocarcinoma HepG2 | Colon cancer HCT-116 | Adenocarcinoma of lung A549 |
| Compound 1 | 34.250±1.59 | 24.565±2.74 | 33.719±3.21 | 37.819±0.39 |
| Compound 2 | 31.316±2.63 | 23.869±1.79 | 29.190±2.37 | 34.0573±1.17 |
Claims (3)
1. a Berkeleyones compound, it is characterised in that its structural formula as shown in the formula (I):
。
2. the preparation method of Berkeleyones compound described in claim 1, it is characterised in that comprise the steps:
S1. marine fungi sclerotium penicillium sp Penicilliumsclerotiorum.SJ0167 bacterial strain being accessed seed culture medium, shaking table 100 ~ 150rpm cultivates 5 ~ 7 days, obtains seed culture fluid；
S2. accessing in fermentation medium by seed culture fluid, room temperature quiescent culture obtains fermented product 1 ~ February；
S3., fermented product is used methanol soak extraction, and methanol extract liquid extracts through ethyl acetate after concentrating, concentrates, and obtains extractum, and extractum through chromatography, obtains the compound 1 shown in formula (I) and compound 2 again；
Wherein, described sclerotium penicillium sp Penicilliumsclerotiorum.SJ0167 bacterial strain is in China Committee for Culture Collection of Microorganisms's common micro-organisms center (CGMCC) preservation, and preservation date is December in 2013 23, and preserving number is CGMCCNO:8628；
The component of seed culture medium described in step S1 is: glucose 18 ~ 23g, peptone 4 ~ 5g, yeast extract 1 ~ 2g, sea salt 55 ~ 65g, water 1.5 ~ 2L；
The component of fermentation medium described in step S2 is: rice 50 ~ 70g, sea salt 1.5 ~ 2g, water 50 ~ 70mL；
The consumption of methanol described in step S3 is and fermented product equal-volume；The consumption of ethyl acetate is the 1/3 of methanol usage；Described extractum silica gel column chromatography separates, 10:0 is used respectively when silicagel column carries out chromatography, 9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8, the petroleum ether-ethyl acetate gradient elution of 1:9 and 0:10, by 7:3, the petroleum ether-ethyl acetate elution fraction of 6:4 and 5:5 merges, chromatograph through polydextran gel SephadexLH-20, it is the further eluting of eluant with petroleum ether-methylene chloride-methanol that volume ratio is 2:1:1, again through HPLC, it is eluent with the methanol-water that volume ratio is 6:4, obtain the compound 1 shown in formula (I) and compound 2.
3. Berkeleyones compound application in preparing cancer therapy drug described in claim 1, it is characterised in that described anticancer for anti-breast cancer, anti-liver cancer and anti-, inhibitor against colon carcinoma cells or Antilung gland cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410072112.8A CN103910746B (en) | 2014-02-28 | 2014-02-28 | The Berkeleyones compound in one class marine fungi source and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410072112.8A CN103910746B (en) | 2014-02-28 | 2014-02-28 | The Berkeleyones compound in one class marine fungi source and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103910746A CN103910746A (en) | 2014-07-09 |
| CN103910746B true CN103910746B (en) | 2016-08-03 |
Family
ID=51036796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410072112.8A Expired - Fee Related CN103910746B (en) | 2014-02-28 | 2014-02-28 | The Berkeleyones compound in one class marine fungi source and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103910746B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3129380B1 (en) | 2014-04-11 | 2018-11-28 | Boehringer Ingelheim International Gmbh | Spiro[3h-indole-3,2'-pyrrolidin]-2(1h)-one derivatives and their use as mdm2-p53 inhibitors |
| US10576064B2 (en) | 2014-07-03 | 2020-03-03 | Boehringer Ingelheim International Gmbh | Spiro[3H-indole-3,2′-pyrrolidin]-2(1H)-one compounds and derivatives as MDM2-P53 inhibitors |
| NZ728685A (en) | 2014-08-21 | 2024-01-26 | Boehringer Ingelheim Int | New spiro[3h-indole-3,2´-pyrrolidin]-2(1h)-one compounds and derivatives as mdm2-p53 inhibitors |
| CN113214270A (en) | 2015-10-09 | 2021-08-06 | 勃林格殷格翰国际有限公司 | Compounds and derivatives thereof as MDM2-P53 inhibitors |
| CN106188084B (en) * | 2016-06-24 | 2018-07-03 | 中山大学 | The naphthalene Spiroketals class compound in marine fungi source and its preparation method and application |
| CN107721990B (en) * | 2017-08-25 | 2020-10-20 | 中山大学 | Marine fungus-derived isoindolinone compounds, preparation method thereof and application thereof in preparation of anti-inflammatory drugs |
| CN115806881A (en) * | 2022-12-09 | 2023-03-17 | 济南大学 | Penicillium fungus and application thereof in preparation of antibacterial drugs |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3233476B2 (en) * | 1992-10-22 | 2001-11-26 | 社団法人北里研究所 | FO-1289 substance and method for producing the same |
| CN102936252B (en) * | 2012-10-22 | 2015-03-04 | 中山大学 | Sesterterpine compounds, and preparation method and application thereof |
-
2014
- 2014-02-28 CN CN201410072112.8A patent/CN103910746B/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN103910746A (en) | 2014-07-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103910746B (en) | The Berkeleyones compound in one class marine fungi source and its preparation method and application | |
| CN103910708B (en) | The Azaphilones compound in a kind of thalassiomycetes source and its preparation method and application | |
| CN102311981B (en) | Method for preparing and purifying prodigiosin | |
| CN106085868B (en) | One plant of Aspergillus and its application | |
| CN103911407B (en) | The preparation method of the Azaphilone class dimer compound in a kind of marine fungi source and application | |
| Song et al. | Microbial transformation of ginsenosides extracted from Panax ginseng adventitious roots in an airlift bioreactor | |
| CN103910701B (en) | The naphthoquinone compound in a kind of thalassiomycetes source and its preparation method and application | |
| CN102127511B (en) | Penicillium decumbens, culture method thereof, and application thereof in transforming steroid medicines | |
| CN110862371B (en) | Polycyclic polyketone compound, preparation method thereof and application thereof in preparation of antibacterial drugs | |
| CN108570025A (en) | The oxygen-containing pentacyclic pimarane diterpene-kind compound of one kind, preparation method and applications | |
| CN104628680A (en) | Sesquiterpene lactone compounds with antibacterial activity and application thereof | |
| Wang et al. | The selective anti-fungal metabolites from Irpex lacteus and applications in the chemical interaction of Gastrodia elata, Armillaria sp., and endophytes | |
| Dasanayaka et al. | New dibenzodioxocinone and pyran-3, 5-dione derivatives from the deep-sea-derived fungus Penicillium canescens SCSIO z053 | |
| CN107954839A (en) | A kind of antiinflammatory active compound peniroquesine A and its preparation method and application | |
| CN102757443B (en) | Sulfur-substituted podophyllum derivative and bioconversion, separation and purification method thereof | |
| CN111808015B (en) | Phenylalanine-derived cytochalasin as well as preparation method and application thereof | |
| CN108558606A (en) | A kind of Dimeric sesquiterpene compound peniroquesines and its preparation method and application | |
| CN114621092A (en) | Phenolic compound in mangrove plant-derived fungi and preparation method thereof | |
| CN103360329B (en) | One class compound phenazine and preparing the application in antitumor drug | |
| CN102234669B (en) | Biotransformation and purification method of 4-(2,3,5,6-tetramethylpyrazine-1-group)-4'-demethylepipodophyllotoxin | |
| CN102329829B (en) | Method for converting daidzein into 8-hydroxydaidzein by utilizing penicillium | |
| CN102452916B (en) | New aromatic polyketones, extraction method and application thereof | |
| Hoang et al. | Steroid components of marine-derived fungal strain Penicillium levitum N33. 2 and their biological activities | |
| CN104673676A (en) | Harmful mycogone perniciosa and ergot sterane type triterpenoid prepared by fermentation as well as method | |
| CN114469908B (en) | Preparation method and application of acinetobacter baumanii-resistant compound stephol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160803 Termination date: 20210228 |