CN105037316B - Active component and its application of separation are extracted in a kind of leaf aspidistra plant from ovum - Google Patents
Active component and its application of separation are extracted in a kind of leaf aspidistra plant from ovum Download PDFInfo
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- CN105037316B CN105037316B CN201510404063.8A CN201510404063A CN105037316B CN 105037316 B CN105037316 B CN 105037316B CN 201510404063 A CN201510404063 A CN 201510404063A CN 105037316 B CN105037316 B CN 105037316B
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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
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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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- 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
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Abstract
The present invention relates to a kind of benzene a pair of horses going side by side coumarin kind compound and the preparation method and purposes of simple plant source xanthone compound.The present invention uses ovum leaf aspidistra（Aspidistra typicaBaill.）Produce structure novel benzene a pair of horses going side by side coumarin kind compound and simple plant source xanthone compound.It is verified by experiments, above-claimed cpd can be used as medical inhibiting-bacteria preparation.
Description
Technical field
The present invention relates to use ovum leaf aspidistra（Aspidistra typicaBaill.）（Deposit number is：No.
20140316-1）The method for producing simple plant source xanthone compound and new benzene a pair of horses going side by side coumarin kind compound；This hair
It is bright to further relate to this purposes of two classes compound in antibiotic preparation is prepared, belong to pharmaceutical field.
Background technology
Ovum leaf aspidistra（Scientific name：Aspidistra typica Baill.）It is Asparagaceae aspidistra,
Root-like stock is thicker, nearly cylinder.2-3 pieces of fasciation of leaf, oval shape lanceolar is to avette；Petiole is substantially, hard.Total bennet is in often cluster
Extract out, it is very thin；3-5 pieces of bract, it is avette；There are purple choice refreshments, inner face darkviolet in perianth urceolus, outside；Sliver is avette, shorter；It is male
6 pieces of stamen, it is several without filigree；Ovary is short, style tubbiness, without joint；Column cap is big, circular, is expanded in peltate.Berry is spherical.Florescence 8-9
Month.Are produced from the west and south such as Yunnan and the Northwest, Vietnam is also distributed in.Be born in remote, thickly forested mountains, mountain valley, at the moistening of small stream side.Ovum leaf spider
The research of the pharmacological activity and its active component hatched is rarely reported, existing research only isolated wherein steroidal soap soap therefrom
Methods of glycosides.And its medicinal its rhizome extensively among the people, claim its promoting blood circulation and removing blood stasis, removing toxic substances analgesic effect is good, cures mainly deficiency of the kidney, pain in the back,
Rheumatic pain, body traumatic injury etc., but its active component has no system research.
The present inventor therefrom isolates the novel benzene a pair of horses going side by side coumarin kind compound and simple plant source xanthene of structure first
Ketone compounds.Research find shown in containing benzene a pair of horses going side by side coumarin kind compound and plant source xanthone compound have it is good
Antibacterial activity, has not yet to see the structure and its report of antibacterial activity to new benzene a pair of horses going side by side coumarin compound, also has no plant
The report of the anti-Gram-negative bacteria activity of source xanthone compound, therefore in the market also not yet has the medicine relevant with this.
The content of the invention
The present invention is intended to provide a kind of noval chemical compound with the effect of good antibacterial activity of unique structure, its structural formula is such as
Under：
Formulas I
Its architectural feature is： R1It is amino, hydrogen, hydroxyl, C1-10Alkoxy, C1-10Acyloxy or C1-10Amide groups；R2For
Methyl；R3It is amino, hydrogen, hydroxyl, C1-10Alkoxy, C1-10Acyloxy or C1-10Amide groups.
Currently preferred compound of formula I is R1It is hydroxyl, R2It is methyl, R3It is hydroxyl.
It is contemplated that also providing a kind of simple plant source xanthone compound, the compound has good antibacterial
Active function, its structural formula is as follows：
Formula II
Its architectural feature is： R1It is amino, hydrogen, hydroxyl, C1-10Alkoxy, C1-10Acyloxy or C1-10Amide groups；R2For
Methyl； R3It is amino, hydrogen, hydroxyl, C1-10Alkoxy, C1-10Acyloxy or C1-10Amide groups.
Currently preferred Formula II compound is R1It is hydroxyl, R2It is methyl, R3It is hydroxyl.
C of the present invention1-10The preferred C of alkoxy1-6Alkoxy, more preferably methoxyl group, ethyoxyl, propoxyl group, fourth oxygen
Base, isopropoxy, amoxy, hexyloxy etc.；
C of the present invention1-10The preferred C of acyloxy1-6Acyloxy, more preferably formyloxy, acetoxyl group, propionyloxy,
Butyryl acyloxy, isopropenoxy, valeryl epoxide, hexylyloxy etc.；
C of the present invention1-10The preferred C of amide groups1-6Amide groups, more preferably formamido, acetamido, propionamido-,
Amide-based small, Isopropamide base, valeryl amido, hexanoyl amido etc.；
Part of compounds in formula I can be prepared by the following method and obtain：
,
Wherein R is amino, C1-10Alkoxy, C1-10Acyloxy or C1-10Amide groups
Part of compounds in Formula II of the present invention can be prepared by the following method and obtain：
,
Wherein R is amino, C1-10Alkoxy, C1-10Acyloxy or C1-10Amide groups
Part of compounds in formula I and II can be obtained containing activity by extracting aspidistra rhizome
The extract of component cpd, then from extract using silica gel column chromatography, prepare the methods such as thin-layer chromatography and isolate and purify
Arrive.
The preferred following methods of formula I and II compound are prepared：（1）It is original to choose the rhizome of ovum leaf aspidistra
Material, uses ethanol（It is preferred that 70%）Ultrasonic extraction is carried out, is filtered, filter off the dregs of a decoction, filtrate merging is concentrated under reduced pressure into medicinal extract, without alcohol taste；
Then concentrate is dispersed in water, uses petroleum ether（30 ~ 60 DEG C of boiling range）, chloroform, ethyl acetate and n-butanol extract successively, extract
It is concentrated under reduced pressure respectively after taking, obtains the medicinal extract of each solvent；（2）It is sample to choose ovum leaf aspidistra chloroform medicinal extract, through silica gel column layer
Analysis, and the use of the mixed solvent of chloroform and methyl alcohol is eluting solvent, with thin-layer chromatography as detection means, eluent concentration, merges
Obtain five parts of Fr.A1~Fr.A5；（3）It is sample to choose Fr.A2 parts, and uses silica gel mixed sample, carries out silica gel column chromatography,
Use chloroform：Methyl alcohol（300:1~10:1）System carries out gradient elution, gained separate sample be divided into Fr.A2-1, Fr.A2-2 and
The parts of Fr.A2-3 tri-；（4）Selection Fr.A2-2 is sample, through silica gel column chromatography, petroleum ether：Ethyl acetate（200:1~3:1）For
Eluant, eluent is purified, and obtains compound II（Ovum leaf cumarin first）；（5）Selection Fr.A2-1 is sample, through silica gel column chromatography again
Secondary purifying, obtains compound I ovum leaf xanthone first.Listed in following examples of the invention using ovum leaf aspidistra
（Aspidistra typicaBaill.）（Deposit number is：No. 20140316-1）Rhizome, prepare invention formula compound I and
The example of II.
Brief description of the drawings
Fig. 1 ovum leaf aspidistra roots polar fraction extracts flow.
Fig. 2 compounds I 2D-NMR data (1H:600MHz; 13C:150MHz)。
Fig. 3 compounds II 2D-NMR data (1H:600MHz; 13C:150MHz)。
Fig. 4 ovum leaf cumarin first, ovum leaf xanthone first and its derivative to the minimum antibacterial dense of gram-positive bacteria
Degree（MIC value）.
The minimum inhibitory concentration of Fig. 5 ovum leaf cumarin first, ovum leaf xanthone first and its derivative to Gram-negative bacteria
（MIC value）.
The MBC of Fig. 6 ovum leaf cumarin first, ovum leaf xanthone first and its derivative（MBC values）.
Specific embodiment：
Embodiment 1：The structural formula of signified compound I in examples below：
Compound I
The preparation of 1 medicinal extract
The ovum leaf dry sliced 5.55Kg of aspidistra rhizome, 70% EtOH Sonicate is extracted 3 times（Mass volume ratio is 1：30）,
It is ultrasonic 1 hour every time.The dregs of a decoction are filtered off, filtrate merging is concentrated under reduced pressure into medicinal extract, without alcohol taste；Then concentrate is dispersed in water,
Use petroleum ether（30 ~ 60 DEG C of boiling range）, chloroform, ethyl acetate and n-butanol extract 3 times respectively successively, 50 DEG C are concentrated under reduced pressure respectively,
Obtain each several part medicinal extract.Merge chloroform extract concentrate drying and obtain 21.14 g, the g of ethyl acetate extract 13.43 is (see Fig. 1）.
The separation and purification of 2 compounds
The g of ovum leaf aspidistra chloroform portion 21.14, through silica gel column chromatography (silica gel H, 200~300 mesh, 420g, chloroform：
Methyl alcohol 500:1~10:1 wash-out), thin-layer chromatography（TLC）Detection, eluent concentrates and merges and to obtain five portions of Fr.A1~Fr.A5
Point.
Fr.A2 parts are light yellow powder, about 5.4g, with silica gel（100-200 mesh）Sample is mixed, air-drying carries out H silicagel columns
Chromatography, uses chloroform：Methyl alcohol（300:1~10:1）System carries out gradient elution, and one bottle is connect per 75ml.Three parts are obtained,
Fr.A2-2 is through H silica gel column chromatographies, petroleum ether：Ethyl acetate（200:1~3:1）System is eluted, and obtains compound 2（Ovum leaf tonka-bean
Plain first）, about 12mg.
White amorphous powder, molecular formula C14H10O4, 182~183 °C of fusing point, optical activity -1.658 (c1.00,
MeOH), IR (KBr) cm-1：3468, 1638；HR-ESI-MSm/z ：Measured value 241.0500 [M-H]+；It is calculated as
C14H9O4, 241.0477；1H NMR and 13C NMR (400 Hz, CDCl3)：See Fig. 2.
Embodiment 2：The structural formula of signified compound II in examples below：
Compound II
The preparation of 1 medicinal extract
With embodiment 1.
The separation and purification of 2 compounds
The g of ovum leaf aspidistra chloroform portion 21.14, through silica gel column chromatography (silica gel H, 200~300 mesh, 420g, chloroform：
Methyl alcohol 500:1~10:1 wash-out), thin-layer chromatography（TLC）Detection, eluent concentrates and merges and to obtain five portions of Fr.A1~Fr.A5
Point.
Fr.A2 parts are light yellow powder, about 5.4g, with silica gel（100-200 mesh）Sample is mixed, air-drying carries out H silicagel columns
Chromatography, uses chloroform：Methyl alcohol（300:1~10:1）System carries out gradient elution, and one bottle is connect per 75ml.Three parts are obtained,
Fr.A2-1 through H silica gel column chromatographies, after its purity is known in TLC inspections, obtains compound I ovum leaf xanthone first, about 35mg again.
Yellow amorphous powder, molecular formula C16H11FO6, 149~150 °C of fusing point, optical activity -0.1773 (c1.00,
MeOH), IR (KBr) cm-1：3422, 1602, 1477；ESI-MSm/z (%)：318[M+H+] (100)；HR-ESI-
MSm/z ：Measured value 318.3004 [M+H]+；It is calculated as C16H11FO6, 318.2933.1H NMR and 13C NMR (600
Hz, CDCl3)：See Fig. 3.
Embodiment 3:The synthesis of ovum leaf the first and second acylated derivatives of cumarin
1
By ovum leaf cumarin first I (10 mg, 0.03 mmol) and DMAP（3 g, 0.02 mmol）It is placed in 25 ml round bottoms
In flask, after being dissolved with 5 ml THF, it is added dropwise two and drips aceticanhydride（About 10 mg, 0.06 mmol), 5 h are reacted in 40 DEG C, decompression is steamed
Dry solvent obtains residue 1a.Residue 1a is through silica gel（0.1 g) column chromatography for separation, chloroform-methanol (220:1) elute, obtain
Compound 1（White amorphous powder, 4.3 mg, yield 43%）.Compound 1：ESIMSm/z 285 [M +H]+。
Embodiment 4:The synthesis of ovum leaf cumarin first methyl-etherified derivative
2
Ovum leaf cumarin first I (20 mg, 0.06 mmol) is placed in 25 ml round-bottomed flasks, is dissolved with 5 ml DMF
Afterwards, 15 mg iodomethane are added dropwise under ice salt bath（About 0.15 mmol）, it is placed in 25 DEG C of 15 min of reaction, plus sodium thiosulfate solid
5 min of a little stirring are quenched iodomethane, and evaporated under reduced pressure solvent obtains residue 2a.Residue 2a is through silica gel（0.2 g) column chromatography
Separate, chloroform-methanol (200:1) elute, obtain compound 2（White amorphous powder, 12 mg, yield 60%）.Compound 2：
ESIMS m/z 271 [M +H]+。
Embodiment 5:The synthesis of ovum leaf the first and second acylated derivatives of xanthone
3 4
By ovum leaf xanthone first II (10 mg, 0.03 mmol) and DMAP（3 g, 0.02 mmol）It is placed in 25 ml
In round-bottomed flask, after being dissolved with 5 ml THF, it is added dropwise two and drips aceticanhydride（About 10 mg, 0.06 mmol), 5 h are reacted in 40 DEG C, subtract
Pressure solvent evaporated obtains residue 3a.Residue 3a is through silica gel（0.1 g) column chromatography for separation, chloroform-methanol (220:1) elute,
Obtain compound 3（White amorphous powder, 8.3 mg, yield 83%）, compound 4（White amorphous powder, 2.4 mg are produced
The % of rate 24）.Compound 3：ESIMSm/z 285 [M +H]+；Compound 4：ESIMSm/z 327 [M +H]+。
Embodiment 6:The synthesis of ovum leaf xanthone methyl-etherified derivative
6
Ovum leaf xanthone first II (10 mg, 0.03 mmol) is placed in 25 ml round-bottomed flasks, it is molten with 5 ml DMF
8 mg iodomethane are added dropwise under Xie Hou, ice salt bath（1 drop, about 0.07 mmol）, it is placed under ice bath and reacts 15 min, plus thiosulfuric acid
5 min of stirring are quenched iodomethane to sodium solid a little, and evaporated under reduced pressure solvent obtains residue 4a.Residue 4a is through silica gel（0.2 g)
Column chromatography for separation, chloroform-methanol (200:1) elute, obtain compound 6（White amorphous powder, 7.8 mg, yield 78%）.
Compound 6：ESIMSm/z 271 [M +H]+。
Embodiment 7：
The test of antibacterial activity in vitro
A. minimum inhibitory concentration（MIC）Measure
1 laboratory sample and experimental technique
Activity experiment is carried out using prepared each compound in embodiment 1-4.
Using micro broth dilution method（Bicro Mroth Dilution, BMD）Positive control is done with Berberine hydrochloride, is surveyed
Determine the MIC value of compound I and II.
The preparation of sample solution：Precision weighs appropriate above-mentioned purified compound I and appropriate II respectively, is prepared with DMSO
Into the solution of required concentration, for surveying activity.
2 experimentations
It is prepared by bacterium solution
The ul of glycerine standard bacteria 100 is inoculated in 3 mL LB meat soups, 37 DEG C of insulating box culture 24h is placed in, then by gold
Staphylococcus aureus streak inoculation on yolk salt agar plate high, by Escherichia coli streak inoculation in maconkey agar flat board
On, by Sarcina lutea and Pseudomonas aeruginosa streak inoculation on MH agar plates.37 DEG C of insulating box 12 ~ 16h of culture are placed in, point
Other its single bacterium colony of picking is cultivated in being inoculated in the LB meat soups of 3 mL, stand-by.
It is prepared by medicine Microdilution susceptibility box
The uL of MH meat soups 100 is added in each Kong Zhongxian of 96 hole elisa Plates, is then 4 mg/mL to concentration is added in the first hole
The uL of medicine dimethyl sulfoxide solution 100, is serially diluted according to 2 times of dilution methods, and first to octal dosing, and the 12nd hole is not
Dosing is used as growth control so that the first hole to the final drug concentration of octal is divided into 1 mg/mL, 0.5 mg/mL, 0.25
Mg/mL, 0.125 mg/mL, 0.0625 mg/mL, 0.0313 mg/mL, 0.0156 mg/mL, are made Microdilution susceptibility box.
Microbionation
Bacteria suspension of the concentration equivalent to 0.50 Maxwell than turbid standard prepared with direct bacterium solution method, plus 50 uL are to micro dilute
Release the drug in each hole of quick box so that it is 5 × 10 not have the final bacterial concentration in hole5 CFU/mL, dilution bacterium solution is finished in inoculation in 15 min,
37 DEG C of 16 ~ 18h of insulating box culture, 4 kinds of bacterium are cooked three repetitions every time, while setting 3 positive drug control groups, positive for bacteria pair
According to group（Only bacterium does not have liquid）, negative control group（Without liquid and bacterium solution）.Clarified with culture medium, visually observed without bacterium
Minimum compound concentration contained by growth hole is designated as MIC value.
B. MBC（MBC）Measure
It is visible without 100uL samples are taken in muddy culture hole from naked eyes on the basis of MIC results, it is spread evenly across battalion
In foster agar solid culture plate.After continuing to cultivate 24h according to MIC condition of culture, to kill the Cmin of 99.9% bacterial number
Or have no obvious colony growth on culture medium be designated as MBC.Experiment is repeated 3 times.
3. experimental result
A. minimum inhibitory concentration（MIC）
Compound I, II and its derivative are to staphylococcus aureus, Sarcina lutea, Pseudomonas aeruginosa and Escherichia coli
Have certain bacteriostasis, its MIC as shown in table 3, table 4, on wherein compound I, II and the acylated derivatives of the two 1,3,4 pairs
The MIC for stating four kinds of bacteriums is respectively：250 ug/mL、250 ug/mL、125 ug/mL、125ug/mL；And its etherification derivative 2
The bacteriostasis of four kinds of bacteriums above-mentioned with 6 pairs there are about reduce, MIC be respectively 500 ug/mL, 500 ug/mL, 250 ug/mL,
250 ug/mL（See Fig. 4, Fig. 5）.Generally visible formula is the oxygen of Formula II for benzene a pair of horses going side by side coumarin kind compound and formula of Formulas I
Miscellaneous anthracene ketone compounds have certain inhibitory action to G+ bacterium and G- bacterium, its suppression to G- bacterium such as Pseudomonas aeruginosa, Escherichia coli
Bacterium effect is better than the effect to G+ such as staphylococcus aureus, Sarcina lutea, and its effect to G- bacterium is small better than hydrochloric acid
Bark of a cork tree alkali is suitable with Berberine hydrochloride.
B. MBC（MBC）
As shown in table 5,1,3,4 pairs of staphylococcus aureuses of compound I, II and the acylated derivatives of the two, gamboge eight are folded
Coccus, Pseudomonas aeruginosa and Escherichia coli MBC are respectively 500 ug/mL, 250 ug/mL, 500 ug/mL and 125 ug/mL；And its
The bacteriostasis of etherification derivative 2 and 6 pairs of above-mentioned four kinds of bacteriums there are about reduce, MIC be respectively 1000 ug/mL, 500 ug/mL,
500 ug/mL、250ug/mL（See Fig. 6）.Its bactericidal effect to Gram-negative bacteria is better than Berberine hydrochloride.
Conclusion
Formula is more apparent for the xanthone compound of Formula II has for benzene a pair of horses going side by side coumarin kind compound and formula of Formulas I
Bacteriostasis, can as bacteriostatic agent be used for antibacterial research.
Claims (3)
1. compound of Formula I：
I
It is characterized in that：R1It is hydroxyl, R2It is methyl, R3It is hydroxyl; R1It is acetoxyl group, R2It is methyl, R3It is hydroxyl；
Or R1It is methoxyl group, R2It is methyl, R3It is methoxyl group.
2. compound according to claim 1, wherein the compound of formula I is preferably：R1It is hydroxyl, R2It is methyl, R3
It is hydroxyl.
3. purposes of any described compound of formula I of claim 1-2 in terms of the pharmaceuticals for suppressing bacterium are prepared, wherein described
Bacterium is staphylococcus aureus, Sarcina lutea, Pseudomonas aeruginosa and Escherichia coli.
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| CN201610931411.1A CN106496177A (en) | 2015-07-13 | 2015-07-13 | One kind extracts detached active component and its application from ovum leaf Rhizoma aspidistrae elatioriss plant |
| CN201510404063.8A CN105037316B (en) | 2015-07-13 | 2015-07-13 | Active component and its application of separation are extracted in a kind of leaf aspidistra plant from ovum |
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| CN109928963B (en) * | 2019-04-02 | 2020-08-25 | 武汉大学 | Antibacterial drug three-carbon-chain methyl piperidine urolithin B and synthesis method and application of hydrochloride thereof |
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