CN103896755A - Chalcone compound and preparation method and application thereof - Google Patents
Chalcone compound and preparation method and application thereof Download PDFInfo
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- CN103896755A CN103896755A CN201410139049.5A CN201410139049A CN103896755A CN 103896755 A CN103896755 A CN 103896755A CN 201410139049 A CN201410139049 A CN 201410139049A CN 103896755 A CN103896755 A CN 103896755A
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- silica gel
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Abstract
The invention discloses a chalcone compound in a higher plant desmodium renifolium and a preparation method and an application thereof. The chalcone compound is separated from desmodium renifolium, and the molecular formula is C21H24O6. The chalcone compound has the following structure as shown in the specification. The preparation method comprises the following steps: by taking a complete stool of desmodium renifolium as a raw material, carrying out extract extraction, column chromatography on silica gel and high-performance liquid chromatography separation, namely smashing the complete stool of desmodium renifolium, and fractionally carrying out ultrasonic treatment, filtering and reduced-pressure concentrating to form an extract; carrying out column chromatography on silica gel on the extract by a silica gel dry column-packing method; carrying out gradient eluting on a chloroform-acetone solution in a volume ratio of 1:0-1:2; and further carrying out separation and purification of high-performance liquid chromatography on an 8:2 part of the eluant to obtain the chalcone compound. Tests verify that the compound has good cell viability to the tobacco mosaic virus. The compound disclosed by the invention is simple in structure, easy to realize artificial synthesis and good in activity, and can be used as a guiding compound for resisting the tobacco mosaic virus.
Description
Technical field
The invention belongs to natural product chemistry field, be specifically related to a kind of chalcone compounds that separation obtains from higher plant renal lobe beggarweed, and the application of this chalcone compounds.
Background technology
Renal lobe beggarweed is pulse family undershrub, is mainly distributed in Yunnan, Shaanxi, Sichuan, Hubei, Hunan, Jiangxi, Fujian, Zhejiang, Jiangsu; In Korea, also there is distribution in Japan.Renal lobe beggarweed is China's conventional Chinese medicinal materials among the people, and root and over-ground part complete stool are medicinal, have the effects such as expelling wind and activating blood circulation, diuresis, desinsection.Study and show both at home and abroad, renal lobe beggarweed main active ingredient is flavonoid compound, comprises flavones, isoflavones, cinnamophenone etc.Cinnamophenone refers to the compound that contains 1,3-diphenylprop ketenes structure in molecule.They are distributed in root, leaf and the skin of multiple medicinal plant in a large number.Because its molecular structure has larger flexibility, can with multiple receptors bind, present biological activity widely, as antitumor, suppress and remove oxyradical, antibacterial, parasiticide, antiviral, antiulcer agent etc.Existing studies confirm that simultaneously, its pharmacological action and chemical structure are closely related, can further research and develop more chalcone compounds, therefrom find effective lead compound and active group.The present invention separates and has obtained a kind of new chalcone compounds with activity of resisting tobacco mosaic virus from renal lobe beggarweed, and this compound it is not yet seen relevant report.
Summary of the invention
The first object of the present invention is to provide a kind of chalcone compounds; The second object is to provide the preparation method of described chalcone compounds; The 3rd object is to provide described chalcone compounds in the application of preparing in resisting tobacco mosaic disease medicine.
The first object of the present invention is achieved in that described compound is to separate and obtain from renal lobe beggarweed, and its molecular formula is C
21h
24o
6, there is following structure:
The second object of the present invention is achieved in that the preparation method of described chalcone compounds is taking renal lobe beggarweed as raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get renal lobe beggarweed sample complete stool, be crushed to 20 ~ 40 orders, and by 90 ~ 99% methyl alcohol supersound extraction 3 ~ 5 times, each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract carries out silica gel column chromatography with 160 ~ 200 order silica gel dry column-packings of 2. ~ 3 times of amounts of weight ratio; Chloroform-acetone solution taking volume proportion as 1:0 ~ 1:2 is carried out gradient elution, merges identical part, collects each several part elutriant concentrated;
C, high pressure liquid chromatography separate: the 8:2 part of B step elutriant further obtains described chalcone compounds with high pressure liquid chromatography separation and purification.
The structure of the chalcone compounds of preparing with aforesaid method is to measure out by the following method:
The compounds of this invention is yellow jelly; Specific rotatory power
be 0.84 (solvent is methyl alcohol, and concentration is 0.18) UV spectrum (solvent is methyl alcohol),
λ max(log ε) 210 (4.59), 220 (4.28), 285 (4.18); Infrared spectra (pressing potassium bromide troche)
ν max3405,3152,3065,2946,2857,1656,1604,1568,1492,1458,1326,1175,1062,868 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak
m/z 395.1476 [M+Na]
+(calculated value 395.1471).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
21h
24o
6, degree of unsaturation is 10.From
1h and
13cNMR spectrum (attribution data is in Table-1) signal can find out in compound have one 1,2,3, the quaternary phenyl ring of 4-and one 1 ', 2 ', 3 '-trisubstituted phenyl ring, has three hydroxyls and 1 methoxy substitution on phenyl ring; In addition, in compound, also have two methylene radical, two methynes, two methyl, the quaternary carbon of an oxidation and a ketone carbonyl signal.These data show that this compound is three ring cinnamophenone structures, common cinnamophenone phenyl ring 2-position replace isopentyl on 2 ' ' position and
β-carbon has formed five yuan of carbocyclic rings.H
3-5 ' ' and H
2-4 ' with C-2 ' ' and C-3 ' '; H-2 ' ' and C-1, C-1 ' ', C-2, C-4 ' ', C-5 ' ', C-
αwith
c-β; H
2-
αwith C-1 ', C-
β, C-1, C=O, and C-2 ' '; H-
βwith C-1, C-1 ' ', C-
α, C-2, and C-2 ' '; H-1 ' ' and C-1, C-2, C-2 ' ', C-
β, and between C-3 ' ', there is HMBC be correlated with (Fig. 7); In addition H,
2-
α/ H-
β/ H-2 ' '/H
2-1 ' ' between exist
1h-
1h COSY, these data also confirm the structure of this cinnamophenone.Further HMBC correlation analysis confirms that in this compound, methoxy substitution is in C-3 position, and three hydroxyls are substituted in C-4, C-2 ' and C-4 ' position.Its steric configuration is determined by coupling constant and the known compound contrast of ROESY Correlated Spectroscopy, specific rotation and hydrogen spectrum.
table-1. compound
1
h NMR and
13
c NMR data (CD
3
)
2
cO)
The 3rd object of the present invention is achieved in that by described chalcone compounds and is applied to the preparation in tobacco mosaic disease medicine.
The compounds of this invention is separated first, has determined for chalcone compounds, and characterized its concrete structure by nucleus magnetic resonance and measuring method of mass spectrum.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches 68.4%, has good activity of resisting tobacco mosaic virus, than the relative inhibition of positive reference substance Nanning mycin (30.5%) height.Above result has disclosed compound of the present invention has good application prospect preparing in resisting tobacco mosaic virus medicine.The compounds of this invention activity simple in structure is good, can be used as the guiding compound of resisting tobacco mosaic virus medicine.
Brief description of the drawings
Fig. 1 is the carbon-13 nmr spectra of compound;
Fig. 2 is the proton nmr spectra of compound;
The HSQC Correlated Spectroscopy of Fig. 3 compound;
The HMBC Correlated Spectroscopy of Fig. 4 compound;
Fig. 5 compound
1h-
1h COSY Correlated Spectroscopy;
The ROESY Correlated Spectroscopy of Fig. 6 compound;
Fig. 7 is the main of compound
1h-
1h COSY is relevant with HMBC.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is further illustrated, but never in any form the present invention is limited, and any conversion or the improvement done based on training centre of the present invention, all fall into protection scope of the present invention.
Except as otherwise noted, the percentage ratio adopting in the present invention is mass percent.
Chalcone compounds C of the present invention
21h
24naO
6preparation method comprise medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, specifically comprise:
A, medicinal extract extract: get renal lobe beggarweed sample, be crushed to 20 ~ 40 orders, and by 90 ~ 99% methyl alcohol supersound extraction 3 ~ 5 times, each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract carries out silica gel column chromatography with 160 ~ 200 order silica gel dry column-packings of 2 ~ 3 times of amounts of weight ratio; Chloroform-acetone solution taking volume proportion as 1:0 ~ 1:2 is carried out gradient elution, merges identical part, collects each several part elutriant concentrated;
C, high pressure liquid chromatography separate: the 8:2 part of B step elutriant further obtains described chalcone compounds with high pressure liquid chromatography separation and purification.
The solvent methanol concentration of described A step is 95%.
The medicinal extract of described B step is before silica gel column chromatography rough segmentation, with 80 ~ 100 order silica gel mixed samples by 0.8 ~ 1.2 times of weight ratio after the pure dissolve with methanol of 1.5 ~ 3 times of amounts of weight ratio.
The chloroform-acetone solution volume proportion of described B step is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2.
Described C step mesohigh liquid chromatography separation and purification is to adopt 21.2 mm × 250 mm, 5
μthe C of m
18chromatographic column, flow velocity is 20 mL/min, the methyl alcohol that moving phase is 58%, it is 390 nm that UV-detector detects wavelength, each sample introduction 200
μl, the chromatographic peak of collection 17.9 min, repeatedly cumulative rear evaporate to dryness.
Material after the separation and purification of described C step mesohigh liquid phase chromatography is used pure dissolve with methanol again, then taking pure methyl alcohol as moving phase, with gel filtration chromatography separation, with further separation and purification.
Chalcone compounds of the present invention is in the application of preparing in resisting tobacco mosaic virus medicine.
Raw materials used area and the kind of not being subject to of the present invention limits, and all can realize the present invention, and to derive from the renal lobe beggarweed sample of Yunnan Yuxi, the present invention will be further described below:
embodiment 1
Renal lobe beggarweed sample source is in In Xishuangbanna of Yunnan.Renal lobe beggarweed is sampled to 2.2 kg and be crushed to 30 orders, 30min is extracted in supersound extraction 3 times of the methyl alcohol with 95% at every turn, and extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 88.5 g.The thick silica gel mixed sample of 100 order with 120 g after the pure dissolve with methanol of 2.5 times of amounts of weight ratio for medicinal extract, the 160 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography, with volume proportion be 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, chloroform-acetone wash-out part that wherein volume proportion is 8:2 separates with prompt logical sequence 1,100 half preparative high-performance liquid chromatographics of peace, methyl alcohol taking 58% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μ m) preparative column are stationary phase, flow velocity is 20 ml/min, it is 285 nm that UV-detector detects wavelength, each sample introduction 200 μ L, collect the chromatographic peak of 17.9 min, repeatedly cumulative rear evaporate to dryness, products therefrom is used pure dissolve with methanol again, then taking pure methyl alcohol as moving phase, with the separation of Sephadex LH-20 gel filtration chromatography, obtains this new compound.
Renal lobe beggarweed sample source is beautiful Dehong in Yunnan, and renal lobe beggarweed sampling 3.5kg is crushed to 40 orders, and 45 min are extracted in supersound extraction 5 times of the methyl alcohol with 90% at every turn, and extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 158 g.The thick silica gel mixed sample of 80 order with 300 g after the pure dissolve with methanol of 2.0 times of amounts of weight ratio for medicinal extract, the 200 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography, with volume proportion be 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, chloroform-acetone wash-out part that wherein volume proportion is 8:2 separates with prompt logical sequence 1,100 half preparative high-performance liquid chromatographics of peace, methyl alcohol taking 58% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μ m) preparative column are stationary phase, flow velocity is 20 ml/min, it is 285 nm that UV-detector detects wavelength, each sample introduction 200 μ L, collect the chromatographic peak of 17.9 min, repeatedly cumulative rear evaporate to dryness, products therefrom is used pure dissolve with methanol again, then taking pure methyl alcohol as moving phase, with the separation of Sephadex LH-20 gel filtration chromatography, obtains this new compound.
embodiment 3
Renal lobe beggarweed sample source, in Honghe, Yunnan, samples 5 kg by renal lobe beggarweed and is crushed to 60 orders, and 60 min are extracted in supersound extraction 3 times of the methyl alcohol with 99% at every turn, and extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 350 g.The thick silica gel mixed sample of 90 order with 500 g after the pure dissolve with methanol of 1.6 times of amounts of weight ratio for medicinal extract, the 180 order silica gel dress posts of 1.8 kg carry out silica gel column chromatography, with volume proportion be 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, chloroform-acetone wash-out part that wherein volume proportion is 8:2 separates with prompt logical sequence 1,100 half preparative high-performance liquid chromatographics of peace, methyl alcohol taking 58% is moving phase, Zorbax SB-C18 (21.2 × 250 mm, 5 μ m) preparative column are stationary phase, flow velocity is 20 ml/min, it is 285 nm that UV-detector detects wavelength, each sample introduction 200 μ L, collect the chromatographic peak of 17.9 min, repeatedly cumulative rear evaporate to dryness, products therefrom is used pure dissolve with methanol again, then taking pure methyl alcohol as moving phase, with the separation of Sephadex LH-20 gel filtration chromatography, obtains this new compound.
Getting compound prepared by embodiment 1, is yellow jelly.
Measuring method is: with nucleus magnetic resonance, in conjunction with other spectroscopic technique qualification structure.
The compounds of this invention is yellow jelly; Specific rotatory power
be 0.84 (solvent is methyl alcohol, and concentration is 0.18) UV spectrum (solvent is methyl alcohol),
λ max(log ε) 210 (4.59), 220 (4.28), 285 (4.18); Infrared spectra (pressing potassium bromide troche)
ν max3405,3152,3065,2946,2857,1656,1604,1568,1492,1458,1326,1175,1062,868 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak
m/z 395.1476 [M+Na]
+(calculated value 395.1471).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
21h
24o
6, degree of unsaturation is 10.From
1h and
13cNMR spectrum (attribution data is in Table-1) signal can find out in compound have one 1,2,3, the quaternary phenyl ring of 4-and one 1 ', 2 ', 3 '-trisubstituted phenyl ring, has three hydroxyls and 1 methoxy substitution on phenyl ring; In addition, in compound, also have two methylene radical, two methynes, two methyl, the quaternary carbon of an oxidation and a ketone carbonyl signal.These data show that this compound is three ring cinnamophenone structures, common cinnamophenone phenyl ring 2-position replace isopentyl on 2 ' ' position and
β-carbon has formed five yuan of carbocyclic rings.H
3-5 ' ' and H
2-4 ' with C-2 ' ' and C-3 ' '; H-2 ' ' and C-1, C-1 ' ', C-2, C-4 ' ', C-5 ' ', C-
αwith
c-β; H
2-
αwith C-1 ', C-
β, C-1, C=O, and C-2 ' '; H-
βwith C-1, C-1 ' ', C-
α, C-2, and C-2 ' '; H-1 ' ' and C-1, C-2, C-2 ' ', C-
β, and between C-3 ' ', there is HMBC be correlated with (Fig. 7); In addition H,
2-
α/ H-
β/ H-2 ' '/H
2-1 ' ' between exist
1h-
1h COSY, these data also confirm the structure of this cinnamophenone.Further HMBC correlation analysis confirms that in this compound, methoxy substitution is in C-3 position, and three hydroxyls are substituted in C-4, C-2 ' and C-4 ' position.Its steric configuration is determined by coupling constant and the known compound contrast of ROESY Correlated Spectroscopy, specific rotation and hydrogen spectrum.
Getting compound prepared by embodiment 2, is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 2 is described chalcone compounds---beggarweed cinnamophenone B.
Getting compound prepared by embodiment 3, is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 3 is described chalcone compounds---beggarweed cinnamophenone B.
Arbitrary chalcone compounds of getting embodiment 1 ~ 3 preparation carries out activity of resisting tobacco mosaic virus test, and test situation is as follows:
Adopt half leaf method, in the time that the mass concentration of medicament is 50 mg/L, the compounds of this invention is carried out to activity of resisting tobacco mosaic virus mensuration.5～6 age flue-cured tobacco plant on, choose be applicable to test blade (leaf is capable normal, anosis without worm), first blade is evenly sprinkled to fine emery powder, tobacco mosaic virus (TMV) source (3.0 × 10-3) for subsequent use is evenly put on the blade sprinkled with silicon carbide with writing brush, after all blades of choosing connect poison and finish, be placed on immediately and in the culture dish that fills liquid, process 20 min, take out, wipe the globule and about liquid on blade, two and half leaves are restored and are emitted in the Enamel jar that is covered with toilet paper moisturizing and add cover glass, temperature control (23 ± 2) DEG C, be placed on greenhouse natural light irradiation, 2～3 d are visible withered spot. each processing is established second half leaf for contrast, be provided with in addition 1 group be commodity Ningnanmycin processing as a comparison, press formula and calculate relative inhibition.
XI％=(CK-T)／CK×100％
X: relative inhibition (%), CK: be soaked in half sheet in clear water and connect the withered spot number (individual) of malicious leaf, T is soaked in half sheet in liquid and connects the withered spot number (individual) of malicious leaf.
The relative inhibition of bright compound of result is 68.4%, far above the relative inhibition 30.5% of contrast Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (8)
1. a chalcone compounds, is characterized in that described compound is to separate and obtain from higher plant renal lobe beggarweed, and its molecular formula is C
21h
24o
6, there is following structure:
2. a preparation method for chalcone compounds claimed in claim 1, is characterized in that, with renal lobe beggarweed complete stool raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, being specially:
A, medicinal extract extract: get renal lobe beggarweed sample, be crushed to 20 ~ 40 orders, and by 90 ~ 99% methyl alcohol supersound extraction 3 ~ 5 times, each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract carries out silica gel column chromatography with 160 ~ 200 order silica gel dry column-packings of 2 ~ 3 times of amounts of weight ratio; Chloroform-acetone solution taking volume proportion as 1:0 ~ 1:2 is carried out gradient elution, merges identical part, collects each several part elutriant concentrated;
C, high pressure liquid chromatography separate: the 8:2 part of B step elutriant further obtains described chalcone compounds with high pressure liquid chromatography separation and purification.
3. the preparation method of chalcone compounds as claimed in claim 2, is characterized in that in described A step, methanol concentration is 95%.
4. the preparation method of chalcone compounds as claimed in claim 2, is characterized in that in described B step that medicinal extract is before silica gel column chromatography rough segmentation, with 80 ~ 100 order silica gel mixed samples by 0.8 ~ 1.2 times of weight ratio after the pure dissolve with methanol of 1.5 ~ 3 times of amounts of weight ratio.
5. the preparation method of chalcone compounds as claimed in claim 2, is characterized in that in described B step, chloroform-acetone solution volume proportion is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2.
6. the preparation method of chalcone compounds as claimed in claim 2, is characterized in that: described C step mesohigh liquid chromatography separation and purification is to adopt 21.2 mm × 250 mm, 5
μthe C of m
18chromatographic column, flow velocity is 20 mL/min, the methyl alcohol that moving phase is 58%, it is 285 nm that UV-detector detects wavelength, each sample introduction 200
μl, the chromatographic peak of collection 17.9 min, repeatedly cumulative rear evaporate to dryness.
7. the preparation method of chalcone compounds as claimed in claim 2, it is characterized in that the material after the separation and purification of described C step mesohigh liquid chromatography uses pure dissolve with methanol again, again taking pure methyl alcohol as moving phase, with gel filtration chromatography separation, with further separation and purification.
8. a chalcone compounds claimed in claim 1 is in the application of preparing in resisting tobacco mosaic virus medicine.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105085193A (en) * | 2015-07-28 | 2015-11-25 | 云南中烟工业有限责任公司 | Novel sesquiterpenoids and preparing method and application of novel sesquiterpenoids |
| CN108888652A (en) * | 2018-07-09 | 2018-11-27 | 云南中医学院 | A kind of renal lobe beggarweed alcohol extract and its application |
| CN110123797A (en) * | 2019-06-06 | 2019-08-16 | 云南中医药大学 | The new application of dihydrochalcone-type compound R enifolin F |
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| CN102304114A (en) * | 2011-08-08 | 2012-01-04 | 云南省烟草农业科学研究院 | Flavanone compound and application thereof |
| CN102942466A (en) * | 2012-10-27 | 2013-02-27 | 青岛农业大学 | Chalcone compound as well as preparation method and application of chalcone compound |
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2014
- 2014-04-09 CN CN201410139049.5A patent/CN103896755B/en active Active
- 2014-04-09 CN CN201510109412.3A patent/CN104817448B/en active Active
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| CN102304114A (en) * | 2011-08-08 | 2012-01-04 | 云南省烟草农业科学研究院 | Flavanone compound and application thereof |
| CN102942466A (en) * | 2012-10-27 | 2013-02-27 | 青岛农业大学 | Chalcone compound as well as preparation method and application of chalcone compound |
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| YAN-PING LI, ET AL.: "Five new prenylated chalcones from Desmodium renifolium", 《FITOTERAPIA》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105085193A (en) * | 2015-07-28 | 2015-11-25 | 云南中烟工业有限责任公司 | Novel sesquiterpenoids and preparing method and application of novel sesquiterpenoids |
| CN108888652A (en) * | 2018-07-09 | 2018-11-27 | 云南中医学院 | A kind of renal lobe beggarweed alcohol extract and its application |
| CN110123797A (en) * | 2019-06-06 | 2019-08-16 | 云南中医药大学 | The new application of dihydrochalcone-type compound R enifolin F |
| CN110123797B (en) * | 2019-06-06 | 2022-04-01 | 云南中医药大学 | New application of dihydrochalcone compound Renifolin F |
Also Published As
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| CN104817448A (en) | 2015-08-05 |
| CN103896755B (en) | 2015-08-19 |
| CN104817448B (en) | 2016-09-07 |
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