CN105037316A - Active ingredient extracted and separated from aspidistra typica baill and application of active ingredient - Google Patents
Active ingredient extracted and separated from aspidistra typica baill and application of active ingredient Download PDFInfo
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- CN105037316A CN105037316A CN201510404063.8A CN201510404063A CN105037316A CN 105037316 A CN105037316 A CN 105037316A CN 201510404063 A CN201510404063 A CN 201510404063A CN 105037316 A CN105037316 A CN 105037316A
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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
Abstract
The invention relates to a preparation method and an application of benzocoumarin compounds and simple plant source xanthone compounds. Aspidistra typica baill is adopted to produce the benzocoumarin compounds and the simple plant source xanthone compounds which are novel in structure. According to experiments, the compounds can be used as medical bacteriostatic preparations.
Description
Technical field
The present invention relates to ovum leaf Rhizome of Common Aspidistra (
aspidistratypicabaill.) (deposit number is: No.20140316-1) produces the method for simple plant-sourced xanthone compounds and novel benzene a pair of horses going side by side coumarin kind compound; The invention still further relates to this two compounds preparing the purposes in antibiotic preparation, belonging to pharmaceutical field.
Background technology
Ovum leaf Rhizome of Common Aspidistra (formal name used at school:
aspidistratypicabaill.) be Asparagaceae aspidistra, root stock is comparatively thick, closely cylindrical.Leaf 2-3 piece clusters, and oval shape lanceolar is to avette; Petiole is obvious, hard.Total bennet is often in a bunch extraction, very thin; Bract 3-5 piece, avette; Perianth urceolus, there is purple choice refreshments outside, inner face intense violet color; Sliver is avette, shorter; 6 pieces, stamen, several without filigree; Ovary is short, and style tubbiness, without joint; Column cap is large, circular, expands in peltate.Berry is spherical.The florescence 8-9 month.Produce the west and south such as Yunnan and the Northwest, be also distributed in Vietnam.Be born in remote, thickly forested mountains, mountain valley, moistening place, small stream limit.The pharmacologically active of ovum leaf Rhizome of Common Aspidistra and the research of activeconstituents thereof rarely have report, and existing research only obtains wherein steroidal soap saponin component from being wherein separated.And its extensively its rhizome medicinal among the people, claim it promoting blood circulation and removing blood stasis, removing toxic substances analgesic effect is good, cure mainly deficiency of the kidney, pain in the back, rheumatic pain, body wound etc., but its activeconstituents there is no systematic study.
The present inventor therefrom isolates benzene a pair of horses going side by side coumarin kind compound of novel structure and simple plant-sourced xanthone compounds first.Containing benzene a pair of horses going side by side coumarin kind compound and plant-sourced xanthone compounds, there is good anti-microbial activity shown in research finds, have not yet to see novel benzene a pair of horses going side by side structure of coumarin compound and the report of anti-microbial activity thereof, also have no the report of plant-sourced xanthone compounds against gram-negative bacteria activity, therefore also not yet there is medicine relevant therewith in market.
Summary of the invention
The present invention aims to provide a kind of new compound with good anti-microbial activity effect of structure uniqueness, and its structural formula is as follows:
Formula I
Its constitutional features is: R
1for amino, hydrogen, hydroxyl, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group; R
2for methyl; R
3for amino, hydrogen, hydroxyl, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group.
The preferred formula I of the present invention is R
1for hydroxyl, R
2for methyl, R
3for hydroxyl.
The present invention is intended to also provide a kind of simple plant-sourced xanthone compounds, and described compound has good anti-microbial activity effect, and its structural formula is as follows:
Formula II
Its constitutional features is: R
1for amino, hydrogen, hydroxyl, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group; R
2for methyl; R
3for amino, hydrogen, hydroxyl, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group.
The preferred formula II compound of the present invention is R
1for hydroxyl, R
2for methyl, R
3for hydroxyl.
C of the present invention
1-10the preferred C of alkoxyl group
1-6alkoxyl group, more preferably methoxyl group, oxyethyl group, propoxy-, butoxy, isopropoxy, pentyloxy, hexyloxy etc.;
C of the present invention
1-10the preferred C of acyloxy
1-6acyloxy, more preferably methanoyl, acetoxyl group, propionyloxy, butyryl acyloxy, isopropenoxy, penta acyloxy, hexylyloxy etc.;
C of the present invention
1-10the preferred C of amide group
1-6amide group, more preferably formamido-, acetamido, propionamido-, amide-based small, Isopropamide base, valeryl amido, hexanoyl amido etc.;
Part of compounds in formula I prepares by following methods:
, wherein R is amino, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group
Part of compounds in formula II prepares by following methods:
, wherein R is amino, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group
Part of compounds in formula I and II obtains the extract containing active compound component by extraction aspidistra rhizome, from extract, then adopt the method separation and purification such as silica gel column chromatography, Preparative TLC chromatography to obtain.
Formula I and the preferred following methods of II compound prepare: the rhizome that (1) chooses ovum leaf Rhizome of Common Aspidistra is raw material, and use ethanol (preferably 70%) to carry out supersound extraction, filter, the elimination dregs of a decoction, filtrate merging is evaporated to medicinal extract, without alcohol taste; Then enriched material is scattered in water, extracts successively with sherwood oil (boiling range 30 ~ 60 DEG C), chloroform, ethyl acetate and propyl carbinol, after extraction, difference concentrating under reduced pressure, obtains the medicinal extract of each solvent; (2) choosing ovum leaf Rhizome of Common Aspidistra chloroform medicinal extract is sample, through silica gel column chromatography, and uses the mixed solvent of chloroform and methyl alcohol for eluting solvent, is detection means, elutriant concentrates, merges and to obtain Fr.A1 ~ Fr.A5 five parts with thin-layer chromatography; (3) choose Fr.A2 part for sample, and use silica gel mixed sample, carry out silica gel column chromatography, with chloroform: methyl alcohol (300:1 ~ 10:1) system carries out gradient elution, gained sample separation is divided into Fr.A2-1, Fr.A2-2 and Fr.A2-3 tri-part; (4) choosing Fr.A2-2 is sample, through silica gel column chromatography, and sherwood oil: ethyl acetate (200:1 ~ 3:1) carries out purifying for eluent, obtains compound
iI(ovum leaf tonka bean camphor first); (5) choosing Fr.A2-1 is sample, through silica gel column chromatography purifying again, obtains Compound I ovum leaf xanthone first.List in following example of the present invention utilize ovum leaf Rhizome of Common Aspidistra (
aspidistratypicabaill.) (deposit number is: No.20140316-1) rhizome, the example of preparation invention formula Compound I and II.
Accompanying drawing explanation
Fig. 1 ovum leaf Rhizome of Common Aspidistra root polar fraction extracts flow process.
The 2D-NMR data of Fig. 2 Compound I (
1h:600MHz;
13c:150MHz).
The 2D-NMR data of Fig. 3 Compound II per (
1h:600MHz;
13c:150MHz).
The minimum inhibitory concentration to gram-positive microorganism (MIC value) of Fig. 4 ovum leaf tonka bean camphor first, ovum leaf xanthone first and derivative thereof.
Fig. 5 ovum leaf tonka bean camphor first, ovum leaf xanthone first and derivative thereof are to the minimum inhibitory concentration (MIC value) of Gram-negative bacteria.
The minimal bactericidal concentration (MBC value) of Fig. 6 ovum leaf tonka bean camphor first, ovum leaf xanthone first and derivative thereof.
specific embodiments:
embodiment 1:the structural formula of the Compound I of indication in following embodiment:
Compound I
The preparation of 1 medicinal extract
The dry sliced 5.55Kg of ovum leaf Rhizome of Common Aspidistra rhizome, 70% ethanol ultrasonic extraction 3 times (mass volume ratio is 1:30), ultrasonic 1 hour at every turn.The elimination dregs of a decoction, filtrate merging is evaporated to medicinal extract, without alcohol taste; Then enriched material is scattered in water, extracts 3 times respectively successively with sherwood oil (boiling range 30 ~ 60 DEG C), chloroform, ethyl acetate and propyl carbinol, 50 DEG C of concentrating under reduced pressure, obtain each several part medicinal extract respectively.Combined chloroform position concentrate drying obtains 21.14g, ethyl acetate extract 13.43g (see figure 1).
The separation and purification of 2 compounds
Ovum leaf Rhizome of Common Aspidistra chloroform portion 21.14g, through silica gel column chromatography (silica gel H, 200 ~ 300 orders, 420g, chloroform: methyl alcohol 500:1 ~ 10:1 wash-out), thin-layer chromatography (TLC) detects, and elutriant concentrates and merges to obtain Fr.A1 ~ Fr.A5 five parts.
Fr.A2 part is light yellow powder, about 5.4g, mixes sample, air-dryly carry out H silica gel column chromatography with silica gel (100-200 order), with chloroform: methyl alcohol (300:1 ~ 10:1) system carries out gradient elution, and every 75ml connects one bottle.Obtain three parts, Fr.A2-2 through H silica gel column chromatography, sherwood oil: ethyl acetate (200:1 ~ 3:1) system wash-out, obtains
compound 2(ovum leaf tonka bean camphor first),about 12mg.
White amorphous powder, molecular formula C
14h
10o
4, fusing point 182 ~ 183 ° of C, specific rotation-1.658 (c1.00, MeOH), IR (KBr) cm
-1: 3468,1638; HR-ESI-MS
m/z: measured value 241.0500 [M-H]
+; Be calculated as C
14h
9o
4, 241.0477;
1hNMRand
13cNMR (400Hz, CDCl
3): see Fig. 2.
embodiment 2:the structural formula of the Compound II per of indication in following embodiment:
Compound II per
The preparation of 1 medicinal extract
With embodiment 1.
The separation and purification of 2 compounds
Ovum leaf Rhizome of Common Aspidistra chloroform portion 21.14g, through silica gel column chromatography (silica gel H, 200 ~ 300 orders, 420g, chloroform: methyl alcohol 500:1 ~ 10:1 wash-out), thin-layer chromatography (TLC) detects, and elutriant concentrates and merges to obtain Fr.A1 ~ Fr.A5 five parts.
Fr.A2 part is light yellow powder, about 5.4g, mixes sample, air-dryly carry out H silica gel column chromatography with silica gel (100-200 order), with chloroform: methyl alcohol (300:1 ~ 10:1) system carries out gradient elution, and every 75ml connects one bottle.Obtain three parts, Fr.A2-1, again through H silica gel column chromatography, after its purity is known in TLC inspection, obtains
compound Iovum leaf xanthone first, about 35mg.
Yellow amorphous powder, molecular formula C
16h
11fO
6, fusing point 149 ~ 150 ° of C, specific rotation-0.1773 (c1.00, MeOH), IR (KBr) cm
-1: 3422,1602,1477; ESI-MS
m/z(%): 318 [M+H
+] (100); HR-ESI-MS
m/z: measured value 318.3004 [M+H]
+; Be calculated as C
16h
11fO
6, 318.2933.
1hNMRand
13cNMR (600Hz, CDCl
3): see Fig. 3.
embodiment 3:the synthesis of ovum leaf tonka bean camphor first and second acylated derivatives
1
By ovum leaf tonka bean camphor first I (10mg, 0.03mmol) and DMAP(3g, 0.02mmol) be placed in 25ml round-bottomed flask, after dissolving with 5mlTHF, drip two aceticanhydrides (about 10mg, 0.06mmol), in 40 DEG C of reaction 5h, evaporated under reduced pressure solvent obtains residue 1a.Resistates 1a is through silica gel (0.1g) column chromatography for separation, and chloroform-methanol (220:1) wash-out, obtains compound
1(white amorphous powder, 4.3mg, productive rate 43%).Compound
1: ESIMS
m/z285 [M+H]
+.
embodiment 4:the synthesis of ovum leaf tonka bean camphor first methyl-etherified derivative
2
By ovum leaf tonka bean camphor first I (20mg, 0.06mmol) be placed in 25ml round-bottomed flask, after dissolving with 5mlDMF, cryosel bath is lower drips 15mg methyl iodide (about 0.15mmol), be placed in 25 DEG C of reaction 15min, add Sulfothiorine solid and stir 5min cancellation methyl iodide a little, evaporated under reduced pressure solvent obtains residue 2a.Resistates 1a is through silica gel (0.2g) column chromatography for separation, and chloroform-methanol (200:1) wash-out, obtains compound
2(white amorphous powder, 12mg, productive rate 60%).Compound
2: ESIMS
m/z271 [M+H]
+.
embodiment 5:the synthesis of ovum leaf xanthone first and second acylated derivatives
34
By ovum leaf xanthone first II (10mg, 0.03mmol) and DMAP(3g, 0.02mmol) be placed in 25ml round-bottomed flask, after dissolving with 5mlTHF, drip two aceticanhydrides (about 10mg, 0.06mmol), in 40 DEG C of reaction 5h, evaporated under reduced pressure solvent obtains residue 3a.Resistates 3a is through silica gel (0.1g) column chromatography for separation, and chloroform-methanol (220:1) wash-out, obtains compound
3(white amorphous powder, 8.3mg, productive rate 83%), compound
4(white amorphous powder, 2.4mg, productive rate 24%).Compound
3: ESIMS
m/z285 [M+H]
+; Compound
4: ESIMS
m/z327 [M+H]
+.
embodiment 6:the synthesis of ovum leaf xanthone methyl-etherified derivative
6
By ovum leaf xanthone first II (10mg, 0.03mmol) be placed in 25ml round-bottomed flask, after dissolving with 5mlDMF, cryosel bath is lower drips 8mg methyl iodide (1, about 0.07mmol), react 15min under being placed in ice bath, add Sulfothiorine solid and stir 5min cancellation methyl iodide a little, evaporated under reduced pressure solvent obtains residue 4a.Resistates 1a is through silica gel (0.2g) column chromatography for separation, and chloroform-methanol (200:1) wash-out, obtains compound
7(white amorphous powder, 7.8mg, productive rate 78%).Compound
6: ESIMS
m/z271 [M+H]
+.
embodiment 7:
The test of antibacterial activity in vitro
A. the mensuration of minimum inhibitory concentration (MIC)
1 laboratory sample and experimental technique
Adopt embodiment
1-4in prepared each compound carry out activity experiment.
Adopt micro-broth dilution method (BicroMrothDilution, BMD) to do positive control with berberine hydrochloride, measure the MIC value of Compound I and II.
The preparation of sample solution: precision takes appropriate above-mentioned purified compound I and II in right amount respectively, is mixed with the solution of desired concn with DMSO, active for survey.
2 experimentations
Bacterium solution preparation
Glycerine standard bacteria 100ul is inoculated in 3mLLB meat soup, be placed in 37 DEG C of thermostat containers and cultivate 24h, then by streptococcus aureus streak inoculation on yolk height salt agar plate, by intestinal bacteria streak inoculation on maconkey agar flat board, by Sarcina lutea and Pseudomonas aeruginosa streak inoculation on MH agar plate.Be placed in 37 DEG C of thermostat containers and cultivate 12 ~ 16h, its single colony inoculation of picking is cultivated in the LB meat soup of 3mL respectively, stand-by.
Prepared by medicine Microdilution susceptibility box
MH meat soup 100uL is added at each Kong Zhongxian of 96 hole enzyme plate, then in the first hole, add concentration is 4mg/mL medicine dimethyl sulfoxide solution 100uL, serial dilution is carried out according to 2 times of dilution methods, first to octal dosing, 12 hole not dosing is as growth control, make the first hole be divided into 1mg/mL, 0.5mg/mL, 0.25mg/mL, 0.125mg/mL, 0.0625mg/mL, 0.0313mg/mL, 0.0156mg/mL to the drug level that octal is final, make Microdilution susceptibility box.
Microbionation
The concentration standby by direct bacterium liquid legal system is equivalent to the bacteria suspension of 0.50 Maxwell than turbid standard, adds 50uL in each hole of Microdilution susceptibility box, makes not have the whole bacterial concentration of Kongzui to be 5 × 10
5cFU/mL, dilution bacterium liquid is inoculated complete in 15min, and 16 ~ 18h cultivated by 37 DEG C of thermostat containers, 4 kinds of bacterium, are cooked three repetitions at every turn, establish 3 positive drug control groups simultaneously, positive for bacteria control group (only having bacterium not have liquid), negative control group (not containing liquid and bacterium liquid).With substratum clarification, visual inspection is designated as MIC value without the minimum compound concentration contained by bacterial growth hole.
B. the mensuration of minimal bactericidal concentration (MBC)
On the basis of MIC result, get 100uL sample from naked eyes are visible without muddy culture hole, be spread evenly across in nutrient agar medium solid culture plate.Continue to cultivate after 24h according to MIC culture condition, with kill 99.9% bacterial number Cmin or on substratum, have no obvious colony growth be designated as MBC.Experiment repetition 3 times.
3. experimental result
A. minimum inhibitory concentration (MIC)
Compound I, II and derivative thereof all have certain bacteriostatic action to streptococcus aureus, Sarcina lutea, Pseudomonas aeruginosa and intestinal bacteria, its MIC as shown in table 3, table 4, wherein Compound I, II and the acylated derivatives of the two
1,
3,
4the MIC of above-mentioned four kinds of bacteriums is respectively: 250ug/mL, 250ug/mL, 125ug/mL, 125ug/mL; And its etherification derivative
2,
5with
6about have reduction to the bacteriostatic action of above-mentioned four kinds of bacteriums, MIC is respectively 500ug/mL, 500ug/mL, 250ug/mL, 250ug/mL(and sees Fig. 4, Fig. 5).The xanthone compounds of visible general formula to be benzene a pair of horses going side by side coumarin kind compound of formula I and general formula be formula II all has certain restraining effect to G+ bacterium and G-bacterium generally, it is to G-bacterium as Pseudomonas aeruginosa, colibacillary bacteriostatic action are better than the effect of G+ as streptococcus aureus, Sarcina lutea, and it is better than berberine hydrochloride or suitable with berberine hydrochloride to the effect of G-bacterium.
B. minimal bactericidal concentration (MBC)
As shown in table 5, Compound I, II and the acylated derivatives of the two
1,
3,
4500ug/mL, 250ug/mL, 500ug/mL and 125ug/mL are respectively to streptococcus aureus, Sarcina lutea, Pseudomonas aeruginosa and intestinal bacteria MBC; And its etherification derivative
2,
5with
6about have reduction to the bacteriostatic action of above-mentioned four kinds of bacteriums, MIC is respectively 1000ug/mL, 500ug/mL, 500ug/mL, 250ug/mL(and sees Fig. 6).It is better than berberine hydrochloride to the sterilization effect of Gram-negative bacteria.
Conclusion
General formula is benzene a pair of horses going side by side coumarin kind compound of formula I and general formula is that the xanthone compounds of formula II has obvious bacteriostatic action, can be used as fungistat for antibacterial research.
[0035]
Claims (10)
1. compound of Formula I:
I
It is characterized in that: R
1for amino, hydrogen, hydroxyl, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group; R
2for methyl; R
3for hydrogen, hydroxyl, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group.
2. compound according to claim 1, wherein said formula I is preferred: R
1for hydroxyl, R
2for methyl, R
3for hydroxyl.
3. Compounds of formula II:
II
It is characterized in that: R
1for amino, hydrogen, hydroxyl, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group; R
2for methyl; R
3for amino, hydrogen, hydroxyl, C
1-10alkoxyl group, C
1-10acyloxy or C
1-10amide group.
4. compound according to claim 3, wherein said formula II compound is preferred: R
1for hydroxyl, R
2for methyl, R
3for hydroxyl.
5. the preparation method of formula I according to claim 2, it is characterized in that with aspidistra rhizome for raw material, adopt solvent extraction to obtain the extract containing active compound component, then use silica gel column chromatography to carry out separating for several times purifying, prepare formula I.
6. the preparation method of formula II compound according to claim 4, it is characterized in that with aspidistra rhizome for raw material, adopt solvent extraction to obtain the extract containing active compound component, then adopt silica gel column chromatography to carry out repeatedly, prepare formula II compound.
7. preparation method according to claim 5, wherein by described extract through silica gel column chromatography, be that solvent carries out gradient elution with chloroform-methanol, 5 are divided into flow part, wherein the 2nd wash-out stream part is through silica gel column chromatography repeatedly, chloroform: methyl alcohol, sherwood oil: ethyl acetate carries out gradient elution, separation and purification obtains formula I.
8. preparation method according to claim 6, wherein by described extract through silica gel column chromatography, be that solvent carries out gradient elution with chloroform-methanol, 5 are divided into flow part, wherein the 2nd wash-out stream part is through silica gel column chromatography repeatedly, chloroform: methyl alcohol, sherwood oil: ethyl acetate carries out gradient elution, separation and purification obtains formula II compound.
9. claim
1the purposes in the pharmaceuticals of anti-bacteria is being prepared, wherein the preferred streptococcus aureus of bacterium, Sarcina lutea, Pseudomonas aeruginosa and intestinal bacteria with described formula I.
10. claim
3the purposes in the pharmaceuticals of anti-bacteria is being prepared, wherein the preferred streptococcus aureus of bacterium, Sarcina lutea, Pseudomonas aeruginosa and intestinal bacteria with described formula II compound.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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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Cited By (2)
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| CN109928963A (en) * | 2019-04-02 | 2019-06-25 | 武汉大学 | The synthetic method and application of a kind of three carbochain methyl piperidine urolithin B of antibacterials and its hydrochloride |
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| CN109498619B (en) * | 2019-01-08 | 2021-02-09 | 云南大学 | Use of a compound for the preparation of a medicament for the treatment and/or prophylaxis of bacterial diseases |
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| NADIA FONTENEAU等: "Synthesis of quinone and xanthone analogs of rhein", 《TETRAHEDRON》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109928963A (en) * | 2019-04-02 | 2019-06-25 | 武汉大学 | The synthetic method and application of a kind of three carbochain methyl piperidine urolithin B of antibacterials and its hydrochloride |
| CN111122763A (en) * | 2019-12-30 | 2020-05-08 | 贵州医科大学 | Quality control method of nine-Dragon-disk |
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| CN106496177A (en) | 2017-03-15 |
| CN105037316B (en) | 2017-07-04 |
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