CN107226801A - A kind of xanthone classes compound and its preparation method of monocrystalline and the application as alpha-glucosidase restrainer - Google Patents
A kind of xanthone classes compound and its preparation method of monocrystalline and the application as alpha-glucosidase restrainer Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07B2200/13—Crystalline forms, e.g. polymorphs
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Abstract
A kind of xanthone classes compound and its preparation method of monocrystalline and the application as α glucosidase inhibitors, first to fungi during preparationPenicillium Sp. (TA33 1) carries out Spawn incubation, then carries out fermented and cultured to the fungi, by gained mycelium chloroform methanol mixed liquor (1:1) extract after being concentrated under reduced pressure for 3 times, coarse extract is extracted with ethyl acetate 3 times to obtain；Ethyl acetate coarse extract carries out normal-phase silica gel column chromatography, the gel filtration chromatographies of Sephadex LH 20, HPLC high performance liquid chromatography successively, produces compound of formula I 1 and 2.The present invention provides a kind of application as α glucosidase inhibitors, it is characterised in that using type I compound 1 and 2 or its pharmaceutically acceptable salt as active ingredient, be used as the application of α glucosidase inhibitors.
Description
Technical field
The present invention relates to preparation method and the application of a kind of xanthone classes compound and its monocrystalline, more particularly to α-
Glucuroide has the xanthone classes compound of extremely strong inhibitory action and its preparation method and the application of monocrystalline.
Background technology
Diabetes are the clinical syndromes as caused by inherent cause and environmental factor, and performance characteristic is hyperglycaemia.In the past
Several years in, the incidence of disease of diabetes increases sharply, and the treatments of diabetes turns into a global health problem.Research shows,
Diabetic more than 85% suffers from type-II diabetes（DM2）, type-II diabetes（DM2）It is that clinical manifestation is the chronic of hyperglycaemia
Disease, the ability of regulation blood glucose is lost mainly due to insulin.Alpha-glucosidase restrainer, such as acarbose, voigelibo
Sugar, Miglitol can hinder the absorption of dietary carbohydrate, achieve and significantly control in the clinical practice for the treatment of diabetes
Therapeutic effect.However, most of said medicines mostly have side effect, such as flatulence, Nausea and vomiting and diarrhoea.Therefore, develop more
Safely and effectively new alpha-glucosidase restrainer is the active demand for treating diabetes.The unique existence ring of marine microorganism
Border (high pressure, high salt, anoxic, lucifuge etc.), promotes marine microorganism metabolism to produce a large amount of structures novelties, activity chemical combination well
Thing, important sources are provided to develop new alpha-glucosidase restrainer or potential treatment diabetes medicament.But close
The report of the microbe-derived compound with alpha-glucosidase restrainer activity of Yu Haiyang is relatively fewer, especially has
The potential report for being developed into treating the marine-derived compound of diabetes medicament.(Wild, S.; Roglic, G., et
al. Diabetes Care (2004) 27, 1047–1053. Campo, V. L.; Aragão-Leoneti, V. et
al. Carbohydr. Chem. (2013) 39, 181–203. Sou, S. et al. Bioorg. Med. Chem.
Lett. (2000) 10, 1081–1084. Crepaldi, G. et al. J. Endocrinol. Invest.（2007）
30, 610–614.。
The content of the invention
It is an object of the invention to provide a kind of xanthone classes compound and its system of monocrystalline from marine fungi
Preparation Method and the application as alpha-glucosidase restrainer, it can meet the demand of prior art.Culture presevation information：
Depositary institution's title：China Committee for Culture Collection of Microorganisms's common micro-organisms center；Depositary institution address：Court of Beijing
Institute of Microorganism, Academia Sinica of the positive institute 3 of area's North Star West Road 1；Preservation date：On April 3rd, 2014；Preservation is compiled
Number：CGMCC No.8994；Classification And Nomenclature：Penicillium sp.
The present invention provides compound of formula I 1 and 2 or its pharmaceutically acceptable salt：
Or its pharmaceutically acceptable salt.
The present invention provides the preparation method of compound of formula I 1 and 2, it is characterised in that first to fungi in bacterium culture medium
Penicilliumsp. (TA33-1) carries out Spawn incubation, then carries out fermented and cultured to the fungi in the fermentation medium, by institute
Obtain mycelium chloroform-methanol mixed liquor (1:1) extract after being concentrated under reduced pressure for 3 times, coarse extract is extracted with ethyl acetate 3 times to obtain；
Ethyl acetate coarse extract is carried out after normal-phase silica gel column chromatography, Sephadex LH-20 gel filtration chromatographies respectively, then high through HPLC
Liquid phantom preparing chromatogram is imitated, gained eluent is concentrated, as compound 1 and 2.
Bacterium culture medium preferably comprises glucose 0.1% -5.0% (percentage by weight, similarly hereinafter), yeast in above-mentioned preparation method
Cream 0.01% -1%, peptone 0.01% -1%, agar 0.1% -3.0%, sodium chloride 0.05% -5%, remaining is water, and cultivation temperature is preferred
For 0-30 °C, incubation time is preferably 3-15 days；Fermentation medium preferably comprise rice 1.0% -80.0% (percentage by weight, under
Together), sodium chloride 0.05%-5%, remaining is water, and cultivation temperature is preferably 0-30 °C, and incubation time is preferably 20-100 days；It is described
Normal-phase silica gel column chromatography use stationary phase preferably 200-300 mesh silica gel, mobile phase preferred volume ratio be 20%-100% second
Acetoacetic ester-petroleum ether mixed solvent；The mobile phase preferred volume ratio that the Sephadex LH-20 gel filtration chromatographies are used is chlorine
It is imitative:Methanol=1:1 mixed solvent；The chromatographic column used in the HPLC high performance liquid preparative chromatographies：Conventional ODS C18 posts, it is excellent
Elect the mm of Kromasil 10 × 250 as, 5 μm, flow velocity is preferably 1.0-5.0 mL/min, mobile phase preferred volume ratio is 20%-
70% Methanol+Water.
Another embodiment of the present invention provides the crystal of type I compound 1, crystal data：Space group is P-1, structure cell ginseng
Number be a=7.123 (4), b=8.069 (4), c=11.596 (6), α=93.86 (3) o, β=93.56 (3) o,
γ= 102.58(3)º, V = 646.99 (505) Å3, Z = 2, Dc = 1.593 g/cm3, F(000) = 324, μ
= 1.144 mm–1。
Another embodiment of the present invention provides the preparation method of the above-mentioned crystal of compound of formula I 1, it is characterised in that by Formulas I
Compound 1 is dissolved in any of methanol, ethanol, water, tetrahydrofuran or acetone or several, stands slow crystallization and can obtain formula
The crystal of I 1.
The condition slowly crystallized is stood in the preparation method of above-mentioned crystal preferably 0-30oUnder C, 1-30 day is stood.
Brief description of the drawings
Figure of description 1 is the XRD of compound of formula I 1.
The present invention obtains xanthone classes compound from marine fungi has strong inhibitory activity to alpha-glucosidase,
It can be used as treating the medicine of diabetes, have a extensive future.
A kind of application as alpha-glucosidase restrainer is provided in another embodiment of the present invention, it is characterised in that
Active ingredient is used as including type I compound 1 and 2 or its pharmaceutically acceptable salt.
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.
A kind of above-mentioned xanthone classes compound as alpha-glucosidase restrainer application.
Embodiment
For the ease of a further understanding of the present invention, examples provided below has done more detailed description to it.But this
A little embodiments only are not used for limiting the scope of the present invention or implementation principle, embodiment party of the invention for more fully understanding invention
Formula is not limited to herein below.
Embodiment 1
(1) flower gorgonian endogenetic fungus Penicillium sp. (TA33-1) Spawn incubation
Culture medium used in Spawn incubation contains glucose 1.0% (percentage by weight, similarly hereinafter), yeast extract 0.2%, peptone
0.2%th, agar 1.0%, sodium chloride 3.0%, remaining is water, and test tube slant is made when using, and fungal bacterial strain is cultivated 3 days under 30 °C.
(2) flower gorgonian endogenetic fungus Penicilliumsp. (TA33-1) fermentation
Culture medium used in fermented and cultured contains rice 40.0% (percentage by weight, similarly hereinafter), sodium chloride 3.0%, and remaining is water；Very
Bacteria strain is cultivated 90 days in 28 °C.
(3) the extraction separation of compound of formula I 1 and 2
The mycelium for taking 60 bottles of steps (2) to obtain, with chloroform-methanol mixed liquor (1:1) extract after being concentrated under reduced pressure for 3 times, use second
Acetoacetic ester extracts 3 times to obtain coarse extract；Ethyl acetate coarse extract carries out normal-phase silica gel column chromatography respectively, and (stationary phase is 200-300
Mesh silica gel；Mobile phase be 100% ethyl acetate solvent), Sephadex LH-20 gel filtration chromatography (chloroforms：Methanol=1：1 it is mixed
Bonding solvent, volume ratio) after, then (chromatographic column is Kromasil 10 × 250 mm, 5 μ through the separation of HPLC high performance liquid preparative chromatographies
M, flow velocity is 2.0 mL/min, and mobile phase is 35% Methanol+Water, volume ratio), gained eluent is concentrated, obtained
Yellow crystal, as compound of formula I 1 and 2.
The structural identification data of compound of formula I 1 and 2：
Compound 1:Yellow crystals；1H NMR (500 MHz, acetone-d6, δ, ppm, J/Hz): 13.60 (1H,
s, H-8), 6.80 (1H, s, H-4), 6.28 (1H, d, J = 1.5 Hz, H-5), 6.17 (1H, d, J =
1.5 Hz, H-7), 2.78 (3H, s, H-11). 13C NMR (125 MHz, acetone-d6, δ, ppm, J/Hz)
183.5 (C, C-9), 165.1 (C, C-6), 164.8 (C, C-8), 158.1 (C, C-10a), 153.5 (C,
C-4a), 152.6 (C, C-3), 141.8 (C, C-2), 125.7 (C, C-1), 112.5 (C, C-1a), 103.9
(C, C-9a), 100.9 (CH, C-4), 98.5 (CH, C-7), 93.6 (CH, C-5), 13.9 (CH3, C-11).
Compound 2:Yellow crystals；1H NMR (500 MHz, acetone-d6, δ, ppm, J/Hz):13.58 (1H,
s, H-8), 6.32 (1H, d, J = 2.0 Hz, H-5), 6.16 (1H, d, J = 2.0 Hz, H-7), 2.73
(1H, s, H-1), 13C NMR (125 MHz, acetone-d6, δ, ppm, J/Hz): 183.1 (C, C-9),
164.1 (C, C-8), 163.8 (C, C-6), 157.1 (C, C-10a), 141.7 (C, C-2), 115.4 (C,
C-1a), 111.2 (C, C-1), 103.1 (C, C-9a), 97.6 (CH, C-7), 92.9 (CH, C-5), 12.3
(CH3, C-11).
Embodiment 2
(1) flower gorgonian endogenetic fungus Penicilliumsp. (TA33-1) Spawn incubation
Culture medium used in Spawn incubation contain glucose 0.1% -5.0% (percentage by weight, similarly hereinafter), yeast extract 0.01% -1%,
Peptone 0.01% -1%, agar 0.1% -3.0%, sodium chloride 0.05% -5%, remaining is water, and test tube slant, fungi are made when using
Bacterial strain is cultivated 3-15 days under 0-30 °C.
(2) flower gorgonian endogenetic fungus Penicilliumsp. (TA33-1) fermentation
Culture medium used in fermented and cultured contains rice 1.0% -80.0% (percentage by weight, similarly hereinafter), sodium chloride 0.05% -5%, its
Yu Weishui, fungal bacterial strain is cultivated 20-100 days in 0-30 °C.
(3) the extraction separation of compound of formula I 1 and 2
Take obtained by 10-60 bottles of steps (2) by gained mycelium chloroform-methanol mixed liquor (1:1) 3 decompressions are extracted dense
After contracting, coarse extract is extracted with ethyl acetate 3 times to obtain；Normal-phase silica gel column chromatography is carried out respectively after the concentration of ethyl acetate coarse extract
(stationary phase is the conventional purification on normal-phase silica gel in this area, and mobile phase is 50% -100% ethyl acetate-light petrol mixed solvent, volume
Than), (mobile phase is chloroform to Sephadex LH-20 gel filtration chromatographies:Methanol=1:1 mixed solvent, volume ratio) after, then pass through
(chromatographic column is this area routine ODS C18 posts to HPLC high performance liquid preparative chromatographies, and flow velocity is 1.0-5.0 mL/min, mobile phase
For 20% -70% Methanol+Water, volume ratio), gained eluent is concentrated, yellow crystal, as compound of formula I 1 is obtained
With 2.
Wherein the structural identification data of type I compound 1 and 2 is consistent with corresponding data in embodiment 1.
Other Spawn incubations, the fermentation condition not particularly pointed out in embodiment 1-2, and normal phase silica gel column chromatography separation,
Other experimental operating conditions such as the separation of Sephadex LH-20 gel filtration chromatographies, high performance liquid chromatography separation are that this area is normal
The experimental operating conditions of rule, those skilled in the art can reasonably be selected according to actual needs.
Embodiment 3
The mg of type I compound 1 1.5 is taken to be dissolved in equipped with any in 500 μ L methanol, ethanol, water, tetrahydrofuran or acetone
In bottle, after standing 30 days under 0 °C, slow crystallization produces the crystal of compound of formula I 1.
Embodiment 4
The mg of type I compound 13 is taken to be dissolved in equipped with any one or several in 1000 μ L methanol, ethanol, tetrahydrofuran or acetone
Bottle in, after standing 1 day under 30 °C, slow crystallization produces the crystal of type I compound 1.
The crystal data of above-mentioned crystal：Space group is P-1, and cell parameter is a=7.123 (4), b=8.069 (4)
Å, c = 11.596(6)Å, α=93.86(3)º,β= 93.56(3)º, γ= 102.58(3)º, V = 646.99 (505)
Å3, Z = 2, Dc = 1.593 g/cm3, F(000) = 324, μ = 1.144 mm–1。
Embodiment 5
Spawn incubation is carried out to marine fungi Penicilliumsp. (TA33-1) in bacterium culture medium, then in fermented and cultured
Fermented and cultured is carried out to the fungi in base, by gained filtering fermentation liquor, thalline is removed, after filtrate is concentrated, is extracted with ethyl acetate
Take；Carried out respectively after normal-phase silica gel column chromatography, Sephadex LH-20 gel filtration chromatographies after extract concentration, then it is high through HPLC
Imitate liquid phantom preparing chromatogram, gained eluent concentrated, obtain yellow crystals, as type I compound 1 and 2, its structural identification data with
Corresponding data is consistent in embodiment 1.Contain glucose, yeast extract, peptone, agar, thick sea in wherein described bacterium culture medium
Contain rice, coarse sea salt, peptone, water in salt, water, the fermentation medium；Described chromatographic isolation is normal phase silicagel column color
Spectrum separation, Sephadex LH-20 gel filtration chromatographies and high performance liquid chromatography separation.
Trained to explore strain in the method for being widely applied to prepare type I compound 1 and 2 of the present invention, the present embodiment
The addition of each composition in base, fermentation medium is supported, is added or is added in any proportion, chromatogram point in conventional ratio in this area
From when the specification of used silica gel, the specification of Sephadex LH-20 gels, the model of chromatographic column and eluting solvent selection,
For the conventional selection of this area.Test result indicates that, the preparation method of above-mentioned conventional selection, the yellow that can be invented is brilliant
Body, i.e. type I compound 1 and 2, its structural identification data are consistent with corresponding data in embodiment 1, only exist individual compound and exist
Fine difference in terms of purity and yield.
The result of embodiment 1-3 shows, according to the conventional Spawn incubation in this area, fermentation condition, conventional purification on normal-phase silica gel
Pillar layer separation, the separation of Sephadex LH-20 gel column chromatographies, the condition of high performance liquid chromatography separation are to marine fungi
Penicilliumsp. (TA33-1) carries out Spawn incubation, ferments, isolates and purifies, and can obtain the chemical combination of structure shown in formula I of the present invention
Thing 1 and 2.The preparation method of type I compound 1 and 2 of the present invention, the method described in preferred embodiment 1-2.
Embodiment 6
The activity experiment of the suppression alpha-glucosidase of type I compound 1 and 2 of the present invention is tested according to following literature method：
Nampoothiri, S. V., Prathapanet A., Cherian O. L., Raghu K.G., Venugopalan V.
V., Sundaresan A., In vitro antioxidant and inhibitory potential of
Terminalia bellerica and Emblica officinalis fruits against LDL oxidation and
key enzymes linked to type 2 diabetes. Food Chem. Toxicol. 2011 49, 125–131.
Experimental result shows that compound of formula I 1 and 2 pairs of α glucuroides prepared by the present invention has very strong inhibitory action, its
IC50Respectively 17.13 μM and 63.79 μM, much stronger than the activity of positive drug acarbose（IC50For 101.45 μM）.
Experiment shows that there is xanthone classes compound 1 and 2 pairs of alpha-glucosidases of the invention very strong suppression to live
Property, treatment hypoglycemic drug can be made into, or even treat the medicine of diabetes, and flower gorgonian endogenetic fungus
Penicilliumsp. large scale fermentation production can be carried out, it is ensured that the natural origin of compound of formula I 1 and 2, should with wide
Use prospect.
Claims (11)
1. the xanthone class compounds of a kind of Formulas I structure, it is characterised in that first to fungi in bacterium culture medium
Penicilliumsp. (TA33-1) carries out Spawn incubation, then carries out fermented and cultured to the fungi in the fermentation medium, by institute
It is 1 to obtain mycelium volume ratio:1 chloroform-methanol mixed liquor is extracted be concentrated under reduced pressure for 3 times after, be extracted with ethyl acetate 3 times slightly
Medicinal extract；Ethyl acetate coarse extract is carried out after normal-phase silica gel column chromatography, Sephadex LH-20 gel filtration chromatographies respectively, then is passed through
HPLC high performance liquid preparative chromatographies, gained eluent is concentrated, and obtains compound of formula I 1 and 2, and its structure is respectively；In wherein described bacterium culture medium containing glucose, yeast extract, peptone,
Agar, coarse sea salt, water；Contain rice, coarse sea salt, water in described fermentation medium；Described chromatographic isolation is purification on normal-phase silica gel
Pillar layer separation, gel filtration chromatography separation and high performance liquid chromatography separation.
2. preparation method as claimed in claim 1, it is characterised in that the bacterium culture medium preferably comprise glucose 0.1%-
5.0%th, yeast extract 0.01% -1%, peptone 0.01% -1%, agar 0.1% -3.0%, sodium chloride 0.05% -5%, remaining is water, above-mentioned
Percentage composition is weight percentage, and cultivation temperature is preferably 0-30 °C, and incubation time is preferably 3-15 days.
3. preparation method as claimed in claim 1, it is characterised in that the fermentation medium preferably comprise rice 1.0%-
80.0% (percentage by weight, similarly hereinafter), sodium chloride 0.05%-5%, remaining is water, and cultivation temperature is preferably 0-30 °C, incubation time
Preferably 20-100 days.
4. the preparation method as described in any one of claim 1-3, it is characterised in that what described normal-phase silica gel column chromatography was used
Stationary phase is 200-300 mesh silica gel, and mobile phase is the ethyl acetate-light petrol mixed solvent that volume ratio is 50%-100%；It is described
The mobile phase that Sephadex LH-20 gel filtration chromatographies are used is chloroform for volume ratio:Methanol=1:1 mixed solvent；It is described
The chromatographic column used in HPLC high performance liquid preparative chromatographies is the mm of Kromasil 10 × 250,5 μm, and flow velocity is 1.0-5.0
ML/min, mobile phase is the Methanol+Water of volume ratio 20% -70%.
5. the compound of formula I 1 described in claim 1 is crystal, it is characterised in that the space group of the crystal is P-1, cell parameter
For a=7.123 (4), b=8.069 (4), c=11.596 (6), α=93.86 (3) o, β=93.56 (3) o, γ=
102.58(3)º, V = 646.99 (505) Å3, Z = 2, Dc = 1.593 g/cm3, F(000) = 324, μ =
1.144 mm–1。
6. the preparation method of crystal described in claim 5, it is characterised in that compound of formula I 1 is dissolved in methanol, ethanol, water, tetrahydrochysene
Any of furans or acetone are several, stand the crystal that slow crystallization can obtain compound of formula I 1.
7. preparation method as claimed in claim 6, it is characterised in that stand the condition slowly crystallized be at 0 30 DEG C, it is quiet
Put 1 30 days.
8. a kind of alpha-glucosidase restrainer, it is characterised in that its contain compound of formula I 1 and 2 described in claim 1 or its
Pharmaceutically acceptable salt is used as active ingredient.
9. a kind of alpha-glucosidase restrainer, it is characterised in that it contains crystal described in claim 5 as active ingredient.
10. the compound of formula I 1 and 2 or its pharmaceutically acceptable salt described in claim 1 are being used as alpha-glucosaccharase enzyme level
The application of agent.
11. the crystal described in claim 7 is in the application as alpha-glucosidase restrainer.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111728964A (en) * | 2020-07-09 | 2020-10-02 | 济南大学 | Application of flavonoid compounds derived from marine fungi |
| CN114774390A (en) * | 2022-01-23 | 2022-07-22 | 中南大学 | Three-dimensional structure of alpha-glucosidase QsGH13 from deep-sea bacteria, and crystal preparation and application thereof |
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| CN103012356A (en) * | 2012-12-24 | 2013-04-03 | 暨南大学 | Compound with alpha-glycosidase inhibitory activity, as well as preparation method and application of compound |
| CN104059044A (en) * | 2014-07-02 | 2014-09-24 | 华南农业大学 | Xanthone derivative and preparation method and application of xanthone derivative |
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2016
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103012356A (en) * | 2012-12-24 | 2013-04-03 | 暨南大学 | Compound with alpha-glycosidase inhibitory activity, as well as preparation method and application of compound |
| CN104059044A (en) * | 2014-07-02 | 2014-09-24 | 华南农业大学 | Xanthone derivative and preparation method and application of xanthone derivative |
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| Title |
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| AHMED ABDEL-LATEFF ET AL.: "Two New Xanthone Derivatives from the Algicolous Marine Fungus Wardomyces anomalus", 《J. NAT. PROD.》 * |
| YI-BIN ZHUANG ET AL.: "Three New Xanthones from the Fungus Penicillium sp. NH-7-1", 《HELVETICA CHIMICA ACTA》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111728964A (en) * | 2020-07-09 | 2020-10-02 | 济南大学 | Application of flavonoid compounds derived from marine fungi |
| CN111728964B (en) * | 2020-07-09 | 2022-02-25 | 济南大学 | Application of flavonoid compounds derived from marine fungi |
| CN114774390A (en) * | 2022-01-23 | 2022-07-22 | 中南大学 | Three-dimensional structure of alpha-glucosidase QsGH13 from deep-sea bacteria, and crystal preparation and application thereof |
| CN114774390B (en) * | 2022-01-23 | 2023-09-22 | 中南大学 | Three-dimensional structure of alpha-glucosidase QsGH13 from deep sea bacteria, and crystal preparation and application thereof |
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