CN110172410A - A kind of aphthopyrans ketone compound in marine fungi source, preparation method and applications - Google Patents
A kind of aphthopyrans ketone compound in marine fungi source, preparation method and applications Download PDFInfo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
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- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
- C12R2001/80—Penicillium
- C12R2001/82—Penicillium chrysogenum
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Abstract
The present invention relates to a kind of aphthopyrans ketone compound in marine fungi source, preparation method and applications, the aphthopyrans ketone compound has structure shown in compound 1-3:
Description
Technical field
The invention belongs to marine fungi secondary metabolite fields, and in particular to a kind of aphthopyrans in marine fungi source
Ketone compounds, preparation method and applications.
Background technique
Naphthopyrone skeleton structure is a kind of important compound in fungal secondary metabolite, shows a variety of biologies
Activity, such as the inhibition of cell toxicant, enzyme etc..The present invention provides a kind of utilization marine fungi Penicillium sp.HK1-22 preparation
Serial aphthopyrans ketone compound and its dimer are obtained, and has carried out overriding resistance pathogenic bacteria and antifungal activity test to it.
Summary of the invention
The culture presevation information of marine fungi Penicillium sp.HK1-22 of the present invention: depositary institution's title: in
State's Microbiological Culture Collection administration committee common micro-organisms center；Depositary institution address: BeiChen West Road, Chaoyang District, BeiJing City 1
Institute 3, Institute of Microorganism, Academia Sinica；Preservation date: on June 11st, 2018；Deposit number: CGMCC No.15865；
Classification naming: mould Penicillium sp..
The present invention provides a kind of aphthopyrans ketone compound or its pharmaceutically acceptable salt, it is characterised in that the naphtho-
Pyranone compounds have structure shown in compound 1-3:
Another embodiment of the present invention provides one kind by marine fungi Penicillium sp.HK1-22 prepare compound
The method of 1-5, it is characterised in that include the following steps:
(1) Spawn incubation first is carried out to marine fungi Penicillium sp.HK1-22 in bacterium culture medium；
(2) it ferments in the fermentation medium to the marine fungi Penicillium sp.HK1-22 in step (1) again
Culture；
(3) by the fermentation material obtained after step (2) fermented and cultured fermentation liquid and thallus separate, fermentation liquid is with organic molten
Agent A is extracted 2~4 times, and fermentation liquid medicinal extract is concentrated under reduced pressure to give after combining extraction liquid；Thallus is extracted 2~4 times with organic solvent B, is closed
And thallus medicinal extract is concentrated under reduced pressure to give after leaching liquor；Merge fermentation liquid medicinal extract and thallus medicinal extract, through chromatographic isolation and/or recrystallization
Obtain compound 1-5；
The structure of compound 1-5 is as follows:
Eluant, eluent involved in preparation method of the present invention, flowing equal proportion refer both to volume ratio；The chromatographic isolation is this
The chromatographic separation technology of field routine, preferably normal-phase silica gel column chromatography, reversed silica gel column chromatography, LH-20 gel filtration chromatography, efficiently
One or more of liquid phase HPLC preparation combines；The recrystallization is the recrystallization technology of this field routine.
Wherein contain glucose, yeast extract, peptone, agar, coarse sea salt, water, fermented and cultured in the bacterium culture medium
Contain glucose, yeast extract, peptone, coarse sea salt, water in base.
In the above-mentioned preparation method of the present invention, organic solvent A ethyl acetate, methylene chloride, chloroform or the ether
One or more of；One or more of the preferred methanol of the organic solvent B, ethyl alcohol, THF or acetone.
Bacterium culture medium preferably comprises glucose 0.1%-10.0%, yeast extract in the above-mentioned preparation method of the present invention
0.01%-5%, peptone 0.01%-5%, agar 0.1%-6.0%, coarse sea salt 0.05%-10%, suitable water；Further
Preferably comprise glucose 0.1%-5.0%, yeast extract 0.01%-2%, peptone 0.01%-2%, agar 0.1%-3.0%,
Coarse sea salt 0.05%-5%；Above-mentioned percentage is weight percentage；Cultivation temperature is preferably 0-45 DEG C, further preferred 5-30
DEG C, still more preferably 15-25 DEG C；Incubation time is preferably 2-10 days, and further preferably 3,5,7 days.Fermentation medium is excellent
Choosing contains glucose 0.1%-10.0%, yeast extract 0.01%-5%, peptone 0.01%-5%, coarse sea salt 0.05%-10%,
Suitable water；It is further preferably glucose 0.1%-5.0%, yeast extract 0.01%-2%, peptone 0.01%-2%, thick
Sea salt 0.05%-5%；Above-mentioned percentage is weight percentage；Cultivation temperature is preferably 0-45 DEG C, further preferred 5-30
DEG C, still more preferably 10-25 DEG C；Incubation time is preferably 20-40 days, and further preferred 21,24,28,30,32,35 days.
Another embodiment of the present invention provides a kind of crystal form of compound 3, it is characterised in that the crystal form is monoclinic crystal
System, cell parameter areα=90 °, β=91.827
(5) °, γ=90 °,Space group P21/ c, Z=4, Dx=1.344mg/mm3, F (000)=640, μ (Mo
K α)=0.103mm-1, 2634 considerable measuring points [2 σ of I > (I)], considerable measuring point refine final discrepancy factor R=0.0987, wR2
=0.2363.
Another embodiment of the present invention provides above-mentioned marine fungi Penicillium sp.HK1-22 and is preparing above-mentionedization
Close the application in object 1-5 and/or 3 crystal form of compound.
Another embodiment of the present invention provide above-mentioned aphthopyrans ketone compound or its pharmaceutically acceptable salt and/or
3 crystal form of compound is preventing and/or is treating the application in agricultural fungal diseases.The agricultural fungal diseases preferably by
Rhizoctonia solania、Rhizoctonia cerealis、Gaeumannomyces graminis、Alternaria
Agricultural fungal diseases caused by one or more in alternate.
Another embodiment of the present invention provides above-mentioned aphthopyrans ketone compound or its pharmaceutically acceptable salt or change
Close application of 3 crystal form of object in preparation prevention and/or treatment agricultural fungal diseases drug.
Another embodiment of the present invention provide above-mentioned aphthopyrans ketone compound or its pharmaceutically acceptable salt and/or
3 crystal form of compound is preparing the purposes in drug-resistance bacteria medicine.The drug-fast bacteria is selected from the drug resistant golden yellow Portugal of methicillin-resistant
Grape coccus (preferably S.aureus ATCC43300, S.aureus ATCC33591).
A kind of drug-resistance bacteria medicine, it is characterised in that comprising above-mentioned aphthopyrans ketone compound or its is pharmaceutically acceptable
Salt or 3 crystal form of compound are as active constituent.The drug-fast bacteria is selected from the drug resistant staphylococcus aureus of methicillin-resistant (preferably
S.aureus ATCC43300、S.aureus ATCC33591)。
The present invention provides a kind of pharmaceutical composition, it is characterised in that comprising above-mentioned aphthopyrans ketone compound or its pharmaceutically
3 crystal form of acceptable salt or compound, and other at least one antibacterials and pharmaceutically acceptable carrier, diluent
Or excipient.Pharmaceutical composition optimizing injection, oral preparation, freeze drying powder injection, the suspending agent etc..Described pharmaceutical composition is used
In prevention and/or treat by the drug resistant staphylococcus aureus of methicillin-resistant (preferably S.aureus ATCC43300,
S.aureus ATCC33591)。
Term " pharmaceutically acceptable salt " refers to the addition of atoxic inorganic or organic acid and/or alkali in the present invention
Salt, reference can be made to " Salt selection for basic drugs ", Int.J.Pharm. (1986), 33,201-217.
It should be understood that within the scope of the present invention, above-mentioned each technical characteristic of the invention and in below (eg embodiment) specifically
Each technical characteristic of description can be combined with each other, to form a new or preferred technical solution.As space is limited, not another herein
One tired states.
Detailed description of the invention
Fig. 1 is compound 11H-1H COSY (600MHz, acetone-d6) figure；
Fig. 2 is HSQC (600MHz, the acetone-d of compound 16) figure；
Fig. 3 is HMBC (600MHz, the acetone-d of compound 16) figure；
Fig. 4 is the ECD figure of compound 1；
Fig. 5 is compound 21H-1H COSY (600MHz, acetone-d6) figure；
Fig. 6 is HSQC (600MHz, the acetone-d of compound 26) figure；
Fig. 7 is HMBC (600MHz, the acetone-d of compound 26) figure；
Fig. 8 is the ECD figure of compound 2；
Fig. 9 is HSQC (600MHz, the acetone-d of compound 36) figure；
Figure 10 is HMBC (600MHz, the acetone-d of compound 36) figure；
Figure 11 is the ECD figure of compound 4 and 5；
Figure 12 is the colony characteristics figure of marine fungi Penicillium sp.IIK1-22.
Specific embodiment
For the ease of a further understanding of the present invention, examples provided below has done more detailed description to it.But
It is that these embodiments are only not supposed to be a limitation to the present invention or implementation principle for better understanding invention, reality of the invention
The mode of applying is not limited to the following contents.
Embodiment 1
(1) culture of marine fungi Penicillium sp.HK1-22 strain
Culture medium used in the Spawn incubation of fungi Penicillium sp.HK1-22 is to be added in every 1000mL water: horse
Bell potato 200g, which boils, takes juice, glucose 20g, coarse sea salt 30g, agar 15g；It is poured into glass culture dish when use, culture is made
Base plate.Fungal bacterial strain is inoculated in culture medium flat plate, shaking table culture 3 days at 25 DEG C.
(2) fermentation of marine fungi Penicillium sp.HK1-22
Fermentation medium used in the fermented and cultured of fungi Penicillium sp.HK1-22 is to add in every 1000mL water
Enter: potato 200g, which boils, takes juice, glucose 20g, coarse sea salt 30g；It is sub-packed in conical flask when use.Fungal bacterial strain is inoculated in
In the culture medium of conical flask, in 20~25 DEG C stationary culture 28 days.
(3) compound 1-5 is isolated and purified
The fermentation material (30L) obtained after step (2) fermented and cultured is taken, fermentation liquid and thallus are separated, fermentation liquid acetic acid
Ethyl ester extracts 3 times, and extract liquor is concentrated under reduced pressure to give fermentation liquid medicinal extract；Thallus is extracted 3 times with methanol, is concentrated under reduced pressure to give thallus leaching
Cream；Merge fermentation liquid medicinal extract and thallus medicinal extract, by depressurizing silica gel column chromatography, eluant, eluent successively uses petroleum ether: ethyl acetate
=100: 0 to 0: 100, ethyl acetate: methanol=100: 0 to 0: 100 gradient is eluted, and by it according to polarity size point
At 5 component Fr.1~Fr.5；Take component Fr.3 through Sephadex LH-20 gel filtration chromatography, eluant, eluent CHCl3: MeOH=
1:1；Tri- components of Fr.3-1~Fr.3-3 are obtained, wherein Fr.3-2 group lease making high-efficient liquid phase chromatogram HPLC prepares (chromatography used
Column is Agilent C18,9.4 × 250mm, 7 μm, flow velocity 2mL/min, mobile phase MeOH: H2O=70: 30), chemical combination is obtained
Object 1 (50.0mg) and 2 (40.0mg)；Fr.3-2 group lease making recrystallizing methanol obtains 3 crystal of compound (20.0mg)；Take component Fr.5
First through normal-phase silica gel column chromatography, (eluant, eluent is methanol: methylene chloride=1: 25 to 1: 15), again through reversed ODS silica gel column chromatography
(MeOH∶H2O=60: 40), through high-efficient liquid phase chromatogram HPLC prepare that (chromatographic column used is Agilent C18,9.4 × 250mm, 7
μm, flow velocity 2mL/min, mobile phase MeOH: H2O=70: 30) compound 4 (2.0mg) and 5 (3.0mgs) are obtained,.Structural identification
Data are as follows:
Compound 1:
[α]20 D+ 89 (c, 0.05, MeOH)；UV(MeOH)λmax332 (0.5) (log ε), 282 (2.5), 232 (1.8) nm；
ECD (1.24mM, MeOH) λmax(Δ ε) 339 (- 2.35), 325 (+0.04), 313 (- 2.10), 296 (+2.73), 280 (-
11.67), 247 (+4.51), 231 (- 2.07) nm；IR(KBr)vmax3379,2948,2843,1642,1454,1361,1054,
1032cm-1；1H and13C NMR is shown in Table 1；HRESIMS m/z 275.0857[M+H]+(calcd for C15H15O5,
275.0860).
Compound 2:
[α]20 D+ 86 (c, 0.06, MeOH)；UV(MeOH)λmax328 (0.4) (log ε), 280 (2.2), 232 (1.5) nm；
ECD (1.24mM, MeOH) λmax(Δ ε) 336 (- 1.69), 325 (- 0.21), 294 (- 11.81), 256 (5.01), 237 (-
3.34)nm；IR(KBr)vmax3377,2948,2833,1641,1455,1419,1032cm-1；1H and13C NMR is shown in Table 1；
HRESIMS m/z 275.0907[M+H]+(calcd for C15H15O5, 275.0914) and
Compound 3:
UV(MeOH)λmax310 (0.05) (log ε), 278 (0.3), 216 (0.11) nm；IR(KBr)vmax3382,2948,
2843,1641,1454,1054,1032cm-1；1H and13C NMR is shown in Table 1；HRESIMS m/z 273.0747[M+H]+
(calcd for C15H13O5, 273.0757) and crystal structure tested by test center, Yangzhou University, with polycrystal X ray diffractometer
(Bruker D8 Advance) uses Mo K alpha rayDiffraction data is collected in scanning at 296K.Crystal form is
Monoclinic system, cell parameter are α=90 °, β
=91.827 (5) °, γ=90 °,Space group P21/ c, Z=4, Dx=1.344mg/mm3, F (000)=
640, μ (MoK α)=0.103mm-1, 2634 considerable measuring points [2 σ of I > (I)], the considerable final discrepancy factor R=of measuring point refine
0.0987, wR2=0.2363.
Compound 4 and 5:
The structural identification data of compound 4 and 51H NMR, ESIMS and report are consistent, and ECD spectrogram is shown in Figure of description
11。
1 compound 1-3 of table NMR data (1H, 600MHz,13C 150Hz, acetone-d6)
Embodiment 2
The compound of the present invention 1-5 according to the previous method of applicant (Journal of Natural Products,
2017,80 (4), 1081-1086), test 6 plants of gram-positive bacterias: 2 plants of the staphylococcus aureus of methicillin resistance:
S.aureus ATCC43300 and S.aureus ATCC33591, responsive type staphylococcus aureus 2 plants: S.aureus
ATCC25923 and S.aureus ATCC29213,1 plant: the E.faecalis ATCC51299 of enterococcus faecalis of drug resistance of vancomycin,
1 plant: E.faecium ATCC35667 of responsive type enterococcus faecium；1 plant of Gram-negative bacteria: E. coli
ATCC25922 the results are shown in Table 2.
Table 2
aData are expressed in MIC values
bO=Oxacillin sodium
cV=VancomycinHCl
dC=Ciprofloxacin
Embodiment 3
According to the band poison culture introduced in document " 74 (2001) 89-96 of Journal of Ethnopharmacology "
Base antifungal activity test method, test 3 crystal form of compound is when concentration is 2,10,50 μ g/mL, to agriculture pathogenic bacteria
(Rhizoctonia solania、Rhizoctonia cerealis、Gaeumannomyces graminis、Alternaria
Alternate inhibitory activity (inhibiting rate %)), the results are shown in Table 3.
Table 3
All references mentioned in the present invention is incorporated herein by reference document, just as each document quilt
It is individually recited as with reference to such.The abbreviation of Chinese and English used in the present invention, code name etc. can be in bibliography or existing skills
The technical manual of art, textbook are found in reference book.In addition, it should also be understood that, after having read above content of the invention, ability
The technical staff in domain can make various changes or modifications the present invention, and such equivalent forms equally fall within right appended by the application and want
Seek book limited range.
Claims (10)
1. a kind of marine fungi Penicillium sp.HK1-22, it is characterised in that its culture presevation information is as follows: depositary institution
Title: China Committee for Culture Collection of Microorganisms's common micro-organisms center；Depositary institution address: the Chaoyang District, Beijing City North Star
The institute 3 of West Road 1, Institute of Microorganism, Academia Sinica；Preservation date: on June 11st, 2018；Deposit number: CGMCC
No.15865；Classification naming: mould Penicillium sp..
2. a kind of aphthopyrans ketone compound or its pharmaceutically acceptable salt, it is characterised in that the aphthopyrans ketone compound
With structure shown in compound 1-3:
3. the method for marine fungi Penicillium sp.HK1-22 prepare compound 1-5 described in claim 1, feature
It is to include the following steps:
(1) Spawn incubation first is carried out to marine fungi Penicillium sp.HK1-22 in bacterium culture medium；
(2) fermentation training is carried out to the marine fungi Penicillium sp.IIK1-22 in step (1) in the fermentation medium again
It supports；
(3) by the fermentation material obtained after step (2) fermented and cultured fermentation liquid and thallus separate, fermentation liquid organic solvent A
Extraction 2~4 times, is concentrated under reduced pressure to give fermentation liquid medicinal extract after combining extraction liquid；Thallus is extracted 2~4 times with organic solvent B, is merged
Thallus medicinal extract is concentrated under reduced pressure to give after leaching liquor；Merge fermentation liquid medicinal extract and thallus medicinal extract, through chromatographic isolation and/or recrystallizes
To compound 1-5；
The structure of compound 1-5 is as follows:
4. a kind of crystal form of compound 3, it is characterised in that the crystal form is monoclinic system, and cell parameter is α=90 °, β=91.827 (5) °, γ=90 °,Space group P21/ c, Z=4, Dx=1.344mg/mm3, F (000)=640, μ (Mo K α)=0.103mm-1, 2634 considerable measuring points [2 σ of I > (I)], considerable measuring point refine final discrepancy factor R=0.0987, wR2=0.2363.
5. marine fungi Penicillium sp.HK1-22 described in claim 1 is preparing compound as claimed in claim 3
Application in 3 crystal form of 1-5 and/or compound as claimed in claim 4.
6. compound 1-5 as claimed in claim 3 or its pharmaceutically acceptable salt and/or compound as claimed in claim 43
Crystal form is preventing and/or is treating the application in agricultural fungal diseases.The agricultural fungal diseases are preferably by Rhizoctonia
Solania, Rhizoctonia cerealis, Gaeumannomyces graminis, one in Alternaria alternate
Kind or several caused agricultural fungal diseases.
7. compound 1-5 as claimed in claim 3 or its pharmaceutically acceptable salt and/or compound as claimed in claim 43
Application of the crystal form in preparation prevention and/or treatment agricultural fungal diseases drug.
8. compound 1-5 as claimed in claim 3 or its pharmaceutically acceptable salt and/or compound as claimed in claim 43
Crystal form is preparing the purposes in drug-resistance bacteria medicine.The drug-fast bacteria is selected from the drug resistant staphylococcus aureus of methicillin-resistant
(preferably S.aureus ATCC43300, S.aureus ATCC33591).
9. a kind of drug-resistance bacteria medicine, it is characterised in that comprising compound 1-5 as claimed in claim 3 or its is pharmaceutically acceptable
Salt and/or 3 crystal form of compound as claimed in claim 4 as active constituent.The drug-fast bacteria is selected from methicillin-resistant drug resistance
Staphylococcus aureus (preferably S.aureus ATCC43300, S.aureus ATCC33591).
10. a kind of pharmaceutical composition, it is characterised in that comprising compound 1-5 as claimed in claim 3 or its is pharmaceutically acceptable
3 crystal form of salt and/or compound as claimed in claim 4, and other at least one antibacterials and pharmaceutically acceptable
Carrier, diluent or excipient.Pharmaceutical composition optimizing injection, oral preparation, freeze drying powder injection, the suspending agent etc..It is described
Pharmaceutical composition is for preventing and/or treating by drug resistant staphylococcus aureus (the preferably S.aureus of methicillin-resistant
ATCC43300、S.aureus ATCC33591)。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114848628A (en) * | 2020-03-26 | 2022-08-05 | 暨南大学 | Application of naphtho-gamma-pyrone compounds in preparation of anti-helicobacter pylori medicines or prevention health-care products |
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| CN102268395A (en) * | 2011-07-22 | 2011-12-07 | 浙江大学 | Marine Penicillium strain and application thereof |
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2019
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102268395A (en) * | 2011-07-22 | 2011-12-07 | 浙江大学 | Marine Penicillium strain and application thereof |
Non-Patent Citations (1)
| Title |
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| SHIQIONG LU: "Bioactive Bis-naphtho-γ-pyrones from Rice False Smut Pathogen Ustilaginoidea virens", 《J. AGRIC. FOOD CHEM.》, vol. 63, pages 3501 - 3508, XP093048697, DOI: 10.1021/acs.jafc.5b00694 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114848628A (en) * | 2020-03-26 | 2022-08-05 | 暨南大学 | Application of naphtho-gamma-pyrone compounds in preparation of anti-helicobacter pylori medicines or prevention health-care products |
| CN114848628B (en) * | 2020-03-26 | 2023-07-25 | 暨南大学 | Application of naphtho gamma-pyrone compounds in preparation of anti-helicobacter pylori medicines or health care products |
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