CN104592330A - Kaempferol derivative separated from Sophora japonica as well as preparation method and application of kaempferol derivative - Google Patents

Kaempferol derivative separated from Sophora japonica as well as preparation method and application of kaempferol derivative Download PDF

Info

Publication number
CN104592330A
CN104592330A CN201510053365.5A CN201510053365A CN104592330A CN 104592330 A CN104592330 A CN 104592330A CN 201510053365 A CN201510053365 A CN 201510053365A CN 104592330 A CN104592330 A CN 104592330A
Authority
CN
China
Prior art keywords
kaempferol
galloyl
crude extract
preparation
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201510053365.5A
Other languages
Chinese (zh)
Other versions
CN104592330B (en
Inventor
司传领
陈晓倩
樊肃
杜海顺
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tianjin University of Science and Technology
Original Assignee
Tianjin University of Science and Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tianjin University of Science and Technology filed Critical Tianjin University of Science and Technology
Priority to CN201510053365.5A priority Critical patent/CN104592330B/en
Publication of CN104592330A publication Critical patent/CN104592330A/en
Application granted granted Critical
Publication of CN104592330B publication Critical patent/CN104592330B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/06—Benzopyran radicals
    • C07H17/065—Benzo[b]pyrans
    • C07H17/07—Benzo[b]pyran-4-ones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention belongs to the technical fields of forest chemistry and active ingredients of trees and in particular relates to a novel kaempferol derivative, namely kaempferol-3-O-(4''-galloyl)-alpha-L-rhamnopyranoside [kaempferol-3-O-(4''-galloyl)-alpha-L-rhamnopyranoside], a preparation method of the kaempferol derivative, and application of the kaempferol derivative in preparation of antibacterial products. The root and bark of Sophora japonica (Sophora japonica L.) are taken as raw materials, the preparation process is standardized and simple, and the experiment proves that the kaempferol-3-O-(4''-galloyl)-alpha-L-rhamnopyranoside has a strong effect of inhibiting strain growth.

Description

One isolated kaempferol derivative and its production and use from Chinese scholar tree
Technical field
The invention belongs to chemistry of forest product and trees activeconstituents technical field, be specifically related to be separated from Chinese scholar tree (Sophora japonica L.) root skin and obtain a kind of new kaempferol derivative and kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides [kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranoside] and its production and use.
Background technology
The deciduous tree that Chinese scholar tree (Sophorajaponica L.) is pulse family (Leguminosae) Papillionoideae (Fabaceae) Sophora (SophoraL.), another name Chinese scholartree, middle Chinese scholar tree, family Chinese scholartree, house lizard Chinese scholartree, spire Chinese scholartree, sophora bud tree etc., it is extensively distributed in the most area of China.The Chinese scholar tree height of tree can reach 15-25m, has root nodule, is suitable for moistening fertile soil (Yang Xin, etc., northern gardening, 2011, (19): 175-178).Document is recorded and is shown, the Chinese scholartree leaf of Chinese scholar tree, sophora flower, Chinese scholartree glue, fruit, bark and tree root all can be used as medicine (Zhao Ken field, etc., plant research, 1999,19 (3): 281-285).Till now, researchist is from Chinese scholar tree all multiple locations extraction and isolation to multiple secondary metabolite, and wherein, flavonoid compound is its main component (Zhang LB, et a1., Fitoterapia, 2013,87:89-92).
In recent years, because of many reasons, Resistant strain continues to increase, and the resistance strengthen continuously of pathogenic bacterium in the bacterial strain such as bacterium and fungi, causes clinical infection case fatality rate to continue to increase.At present, food, the world of medicine scientific research personnel are just actively devoted to find the natural bacteriostatic agent of safety, efficient, wide spectrum.Plant is the natural treasure-house of Substance, and document shows, the whole world had been reported that kind more than 1600 had and suppressed the higher plant of harmful organism, and wherein mycostatic have 94 kinds, and that presses down bacterium has 11 kinds, anti-viral have 17 kinds.Separately there is made at least 1389 kind of plant will likely as sterilant (should to iron, etc., Southwest University for Nationalities journal (natural science edition), 31 (3): 402-409).Thus, in Secondary Metabolism of Plant natural component, find the important thinking (Liu Haiyan, etc., Hebei Agricultural Sciences, 2005,21 (4): 254-257,328) that the material with bacteriostatic activity has become exploitation efficient germicide.
Summary of the invention
The object of this invention is to provide a kind of new kaempferol derivative and kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides [kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranoside].
Another object of the present invention is to provide the method preparing kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides from the root skin of pulse family (Leguminosae) Papillionoideae (Fabaceae) Sophora (SophoraL.) trees Chinese scholar tree (Sophora japonica L.).
3rd object of the present invention is to provide bacteriostatic activity effect purposes of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides.
Technical scheme of the present invention is summarized as follows:
Kaempferol derivative provided by the invention is the compound of following structural formula:
Compound molecule formula of the present invention is C 28h 24o 14, chemistry kaempferol-3-O-by name (4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides, the English of its correspondence is called kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranoside.
From Chinese scholar tree root skin, prepare the method for kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides, comprise the steps:
(1) the Chinese scholar tree root skin plant material of pulverizing is got, be 1: 1 ~ 1: 15 aqueous acetone solutions adding that concentration expressed in percentage by volume is 1% ~ 99% in mass ratio, normal temperature or heating or microwave or ultrasonic extraction 1 ~ 6 time, each 1 ~ 48 hour, filter, filtrate reduced in volume, to 1% ~ 20% of original volume, obtains crude extract;
(2) water of crude extract quality 1 ~ 6 times is added, stir, add the n-hexane extraction 1 ~ 6 time of crude extract quality 1 ~ 6 times, be separated, residue water layer is added the chloroform extraction 1 ~ 6 time of crude extract quality 1 ~ 6 times, be separated, will again remain water layer and add the extraction into ethyl acetate 1 ~ 6 time of crude extract quality 1 ~ 6 times, separating ethyl acetate layer and last water layer, obtain extraction into ethyl acetate phase by ethyl acetate layer concentrating under reduced pressure;
(3) extraction into ethyl acetate prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through at least one of silica gel column chromatography and gel filtration chromatography.
This preparation method has that yield is high, production cost is low, the feature of technique simple specification.
Experiment confirms that kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides all has stronger restraining effect (being respectively 0.5 and 4.0 μ g/ml to the corresponding minimal inhibitory concentration of above-mentioned two kinds of bacterial strains) to the streptococcus aureus (Staphylococcus aureus) in gram-positive microorganism and the Klebsiella pneumonia (Klebsiella pneumonia) in Gram-negative bacteria, the fungistatic effect suitable (Liu Suanyan NEOMYCIN SULPHATE is respectively 0.5 and 2.0 μ g/ml to streptococcus aureus and Klebsiella pneumonia minimal inhibitory concentration) of its fungistatic effect and positive control group Liu Suanyan NEOMYCIN SULPHATE (neomycin).This shows that kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides can suppress the growth of common causative bacterial strain, can be used as efficient antiseptic-germicide and is applied to the fields such as food, healthcare products, pharmaceuticals, makeup.
Embodiment
With reference to the following example by easier, comprehend the present invention, providing embodiment is to illustrate the present invention, instead of limits the present invention by any way.
Embodiment 1:
The preparation of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides
(1) getting the Chinese scholar tree root skin plant material of pulverizing, is 1: 3 aqueous acetone solution adding that concentration expressed in percentage by volume is 70% in mass ratio, extract at room temperature 3 times, each 36 hours, and filter, filtrate reduced in volume, to 10% of original volume, obtains crude extract;
(2) water of crude extract quality 3 times is added, stir, add the n-hexane extraction 3 times of crude extract quality 3 times, be separated, residue water layer is added the chloroform extraction 3 times of crude extract quality 3 times, be separated, will again remain water layer and add the extraction into ethyl acetate 3 times of crude extract quality 3 times, separating ethyl acetate layer and last water layer, obtain extraction into ethyl acetate phase by ethyl acetate layer concentrating under reduced pressure;
(3) extraction into ethyl acetate prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through silica gel column chromatography.
The Structural Identification of this compound:
The m/z [M+Na] of this compound is shown by fast atom bombardment mass spectroscopy(FABMS) (FAB MS) +be 607, m/z [M+H] +be 585, in conjunction with 1h NMR and 13c NMR spectrum show that its molecular formula is C 28h 24o 14.
1h NMR composes proton peak [δ 8.01 (2H, d, J=8.5Hz in (data are in table 1), H-2 ', 6 ') and δ 6.90 (2H, d, J=8.5Hz, H-3 ', 5 ')] the B ring that shows this compound is typical AA ' BB ' formula proton aromatic nucleus.Proton signal [δ 6.20 (1H, d, J=2.3Hz, H-6) and δ 6.39 (1H, d, J=2.3Hz, H-8)] shows that its A ring is Phloroglucinol type.And 13it is typical flavonol that C NMR peak data [δ 159.4 (C-2), 134.8 (C-3), 179.4 (C-4)] discloses this compound.Therefore, the aglycon of this compound is confirmed as kaempferol.
? 1during H NMR composes, show in this compound containing α-L-rhamnopyranosyloxyhy glucosides [1 terminal hydrogen δ 5.29 (1H, br s, H-1 "), methyl δ 0.95 (3H, d; J=6.1Hz; H-6 ") and δ 3.52 ~ 5.03 (4H, H-2 ", 3 ", 4 ", 5 ")].
Proton signal δ 7.09 (2H, s, H-2 " ', 6 " ') combine 13c NMR data [δ 121.9 (C-1 " '), 110.1 (C-2 " ', 6 " '), 146.4 (C-3 " ', 5 " '), 139.9 (C-4 " ')] show in this compound, to comprise a galloyl.
(1H, br s, H-1 ") have Long-Range Correlation with the carbon signal δ 134.8 (C-3) on kaempferol to the rhamnosyl terminal hydrogen δ 5.29 of this compound of HMBC spectrum display, determine that α-L-rhamnopyranosyloxyhy glucosides is connected with the C-3 position of kaempferol.And proton peak δ 5.03 (1H on rhamnosyl; dd; J=10.3Hz; J=9.7Hz; carbon signal δ on H-4 ") and galloyl 168.3 (C-7 " ') there is Long-Range Correlation, then 7 " ' number position and α-L-rhamnopyranosyloxyhy glucosides 4 " number position determining galloyl is connected.
To sum up, the structure of this compound is confirmed as kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides.
Through retrieval, this compound is the new kaempferol derivative never reported before this.This compound is white amorphous powder, and fusing point is 191 ~ 193 DEG C, specific rotation this compound has uv-absorbing under ultraviolet lamp 254nm wavelength, and the color reaction of spraying of the iron trichloride ethanolic soln (mass percent) with 1% is deep green.In TLC test, when launching with the solvent systems of glacial acetic acid-water volume ratio 3: 47, the R of this compound fvalue is 0.49, and when launching with the solvent systems of the trimethyl carbinol-glacial acetic acid-water volume ratio 3: 1: 1, the R of this compound fvalue is 0.73.
Table 1. kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides 1h (400MHz) and 13c NMR (100MHz) modal data (CD 3oD)
Embodiment 2:
The preparation of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides
(1) getting the Chinese scholar tree root skin plant material of pulverizing, is 1: 4 aqueous acetone solution adding that concentration expressed in percentage by volume is 60% in mass ratio, microwave extraction 4 times, each 3 hours, and filter, filtrate reduced in volume, to 8% of original volume, obtains crude extract;
(2) water of crude extract quality 2 times is added, stir, add the n-hexane extraction 4 times of crude extract quality 2 times, be separated, residue water layer is added the chloroform extraction 4 times of crude extract quality 2 times, be separated, will again remain water layer and add the extraction into ethyl acetate 4 times of crude extract quality 2 times, separating ethyl acetate layer and last water layer, obtain extraction into ethyl acetate phase by ethyl acetate layer concentrating under reduced pressure;
(3) extraction into ethyl acetate prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through gel filtration chromatography.
Embodiment 3:
The preparation of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides
(1) getting the Chinese scholar tree root skin plant material of pulverizing, is 1: 2 aqueous acetone solution adding that concentration expressed in percentage by volume is 80% in mass ratio, supersound extraction 2 times, each 4 hours, and filter, filtrate reduced in volume, to 5% of original volume, obtains crude extract;
(2) water of crude extract quality 4 times is added, stir, add the n-hexane extraction 2 times of crude extract quality 4 times, be separated, residue water layer is added the chloroform extraction 2 times of crude extract quality 4 times, be separated, will again remain water layer and add the extraction into ethyl acetate 2 times of crude extract quality 4 times, separating ethyl acetate layer and last water layer, obtain extraction into ethyl acetate phase by ethyl acetate layer concentrating under reduced pressure;
(3) extraction into ethyl acetate prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through gel filtration chromatography and silica gel column chromatography.
Embodiment 4:
The bacteriostatic activity of kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides is evaluated with minimal inhibitory concentration method
1. experiment material
1.1 experimental strains: adopt the streptococcus aureus (Staphylococousaureus) in gram-positive microorganism and the Klebsiella pneumonia (Klebsiella pneumonia) in Gram-negative bacteria for examination bacterial classification in this experiment.Above two kinds of bacterial strains provide by Microbiological Lab of food engineering institute of University Of Science and Technology Of Tianjin.
1.2 experimental installations: isothermal vibration device, constant incubator, Bechtop etc.
1.3 candidate drug: above-mentioned kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides purity after HPLC measures is 99.9%, and the positive control group selected is the Liu Suanyan NEOMYCIN SULPHATE of broad-spectrum high efficacy.
2. operation steps: describe step in the minimal inhibitory concentration method reference literature that test adopts and carry out (Rabe T, van StadenJ, Journal of Ethnopharmacology, 2000,73,171-174).Each group of experiment all independently carries out three times, gets its mean value calculation.
Experimental result is as shown in table 2.Result shows, kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides all has stronger inhibit activities to streptococcus aureus and Klebsiella pneumonia, and its fungistatic effect is suitable with positive control group Liu Suanyan NEOMYCIN SULPHATE fungistatic effect.
Table 2. kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides and Liu Suanyan NEOMYCIN SULPHATE are to the minimal inhibitory concentration (μ g/ml) of experimental strain

Claims (3)

1. the compound of following structural formula:
Chemistry kaempferol-3-O-by name (4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides, the English of its correspondence is called kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranoside.
2. the preparation method of claim 1 compound, is characterized in that comprising the steps:
(1) the Chinese scholar tree root skin plant material of pulverizing is got, be 1: 1 ~ 1: 15 acetonitrile solutions adding that concentration expressed in percentage by volume is 70% ~ 99% in mass ratio, normal temperature or heating or ultrasonic or microwave radiation exaraction 1 ~ 6 time, each 1 ~ 48 hour, filter, filtrate reduced in volume, to 1% ~ 20% of original volume, obtains crude extract;
(2) add the water of crude extract quality 1 ~ 6 times, stir, add the n-hexane extraction 1 ~ 6 time of crude extract quality 1 ~ 6 times, be separated, residue water layer is added the petroleum ether extraction 1 ~ 6 time of crude extract quality 1 ~ 6 times, be separated, petroleum ether layer concentrating under reduced pressure is obtained petroleum ether extraction phase;
(3) petroleum ether extraction prepares kaempferol-3-O-(4 "-galloyl)-α-L-rhamnopyranosyloxyhy glucosides through at least one of silica gel column chromatography and gel filtration chromatography.
3. the application of claim 1 compound in the antibacterial product of preparation.
CN201510053365.5A 2015-02-03 2015-02-03 A kind of kaempferol derivative isolated from Chinese scholar tree and its production and use Expired - Fee Related CN104592330B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510053365.5A CN104592330B (en) 2015-02-03 2015-02-03 A kind of kaempferol derivative isolated from Chinese scholar tree and its production and use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510053365.5A CN104592330B (en) 2015-02-03 2015-02-03 A kind of kaempferol derivative isolated from Chinese scholar tree and its production and use

Publications (2)

Publication Number Publication Date
CN104592330A true CN104592330A (en) 2015-05-06
CN104592330B CN104592330B (en) 2017-06-13

Family

ID=53118424

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510053365.5A Expired - Fee Related CN104592330B (en) 2015-02-03 2015-02-03 A kind of kaempferol derivative isolated from Chinese scholar tree and its production and use

Country Status (1)

Country Link
CN (1) CN104592330B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104961779A (en) * 2015-05-25 2015-10-07 天津科技大学 Caffeoyl group-containing tannin derivative, and preparation technology and application thereof
CN105198943A (en) * 2015-09-24 2015-12-30 安徽农业大学 Acylation flavone glycoside named camellikaempferoside A and preparing method and application thereof
CN105237598A (en) * 2015-09-24 2016-01-13 安徽农业大学 Flavone oxygen glycoside compound named as camellikaempferoside B, and preparation method and applications thereof
CN106928289A (en) * 2017-02-22 2017-07-07 安徽农业大学 One kind is acylated the glucosides of flavones four and its extracting method and application
CN107312050A (en) * 2017-08-28 2017-11-03 天津科技大学 A kind of preparation technology of galloyl flavonol glycosides in katsura tree branch
CN113115798A (en) * 2021-04-23 2021-07-16 北京农学院 Application of Chinese scholartree in biological control, biological control medicament and preparation method thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012107205A1 (en) * 2011-02-08 2012-08-16 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Sweetener and/or a sweetness enhancer, sweetener compositions, methods of making the same and consumables containing the same
US20140271996A1 (en) * 2013-03-14 2014-09-18 Indra Prakash Beverages containing rare sugars

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012107205A1 (en) * 2011-02-08 2012-08-16 Nutrinova Nutrition Specialties & Food Ingredients Gmbh Sweetener and/or a sweetness enhancer, sweetener compositions, methods of making the same and consumables containing the same
US20140271996A1 (en) * 2013-03-14 2014-09-18 Indra Prakash Beverages containing rare sugars

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ELAINE WAN LING CHAN，等: "Galloylated flavonol rhamnosides from the leaves of Calliandra tergemina with antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA)", 《PHYTOCHEMISTRY》 *
HEIDI R. BOKESCH，等: "HIV-1 Ribonuclease H Inhibitory Phenolic Glycosides from Eugenia hyemalis", 《J. NAT. PROD.》 *
李瑞丽，等: "茶条槭叶乙酸乙酯部位化学成分研究", 《吉林农业大学学报》 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104961779A (en) * 2015-05-25 2015-10-07 天津科技大学 Caffeoyl group-containing tannin derivative, and preparation technology and application thereof
CN104961779B (en) * 2015-05-25 2017-09-29 天津科技大学 A kind of tannins derivative and its preparation technology and application containing coffee acyl
CN105198943A (en) * 2015-09-24 2015-12-30 安徽农业大学 Acylation flavone glycoside named camellikaempferoside A and preparing method and application thereof
CN105237598A (en) * 2015-09-24 2016-01-13 安徽农业大学 Flavone oxygen glycoside compound named as camellikaempferoside B, and preparation method and applications thereof
CN105198943B (en) * 2015-09-24 2017-12-22 安徽农业大学 A kind of entitled tea hill how glycosides A acylated flavonoids glucosides and its preparation method and application
CN105237598B (en) * 2015-09-24 2017-12-22 安徽农业大学 A kind of entitled tea hill how glycosides B flavones oxygen glycosides compound and its preparation method and application
CN106928289A (en) * 2017-02-22 2017-07-07 安徽农业大学 One kind is acylated the glucosides of flavones four and its extracting method and application
CN106928289B (en) * 2017-02-22 2019-09-20 安徽农业大学 A kind of four glucosides of acylation flavones and its extracting method and application
CN107312050A (en) * 2017-08-28 2017-11-03 天津科技大学 A kind of preparation technology of galloyl flavonol glycosides in katsura tree branch
CN107312050B (en) * 2017-08-28 2019-11-22 天津科技大学 A kind of preparation process of galloyl flavonol glycosides in katsura tree branch
CN113115798A (en) * 2021-04-23 2021-07-16 北京农学院 Application of Chinese scholartree in biological control, biological control medicament and preparation method thereof
CN113115798B (en) * 2021-04-23 2022-03-29 北京农学院 Application of Chinese scholartree in biological control, biological control medicament and preparation method thereof

Also Published As

Publication number Publication date
CN104592330B (en) 2017-06-13

Similar Documents

Publication Publication Date Title
CN104592330A (en) Kaempferol derivative separated from Sophora japonica as well as preparation method and application of kaempferol derivative
Hazni et al. Phytochemical constituents from Cassia alata with inhibition against methicillin-resistant Staphylococcus aureus (MRSA)
Ebrahim et al. Metabolites from the fungal endophyte Aspergillus austroafricanus in axenic culture and in fungal–bacterial mixed cultures
Wong et al. Chemical constituents and antibacterial activity of Melastoma malabathricum L.
EP1838862B1 (en) Manufacturing method of kaempferol
Hamdi et al. The phytochemical and bioactivity profiles of wild Asparagus albus L. plant
Akhavan et al. Studies on the antioxidant and antimicrobial activity and flavonoid derivatives from the fruit of Trigonosciadium brachytaenium (Boiss.) Alava
Alotaibi et al. Phytochemical contents and biological evaluation of Ruta chalepennsis L. growing in Saudi Arabia
Chen et al. Biological activities of flavonoids from pathogenic-infected Astragalus adsurgens
Ćirić et al. Antimicrobial activity of secondary metabolites isolated from Centaurea spruneri Boiss. & Heldr.
Rashid et al. Flavonoid glycosides from Prunus armeniaca and the antibacterial activity of a crude extract
JP5956439B2 (en) Antibacterial composition
Zhang et al. Isolation of new flavan-3-ol and lignan glucoside from Loropetalum chinense and their antimicrobial activities
CN105503804B (en) The synthesis and the application in anti-tumor aspect of the O acetic acid esters of Quercetin 3
Atta et al. Phytochemical studies on Diplotaxis harra growing in Sinai
CN103788157B (en) A kind of coumarin derivatives and preparation technology thereof and application in Fraxinus velutina
CN104274454B (en) A kind of anti-medicine resistant Staphylococcus aureus composition of medicine and purposes
Uddin et al. Antioxidant, antimicrobial activity and phytochemical investigation of Pterospermum acerifolium (Leaf petiole)
Hang et al. Four new N-phenethylbenzamide derivatives from the stems of piper betle and their antimicrobial activity
Muhammad et al. Potent microbial and tyrosinase inhibitors from stem bark of Bauhinia rufescens (Fabaceae)
CN107540532B (en) Diphenyl ether compound with antibacterial activity in honeysuckle and preparation method and application thereof
Xiao et al. Microbial transformation of quercetin and its prenylated derivatives
CN102887928B (en) Flavonoids from nervilia fordii and preparation method and use thereof
CN102659547B (en) Ophiobolin sesterterpene compound and preparation and application thereof
Manivannan et al. Anti-microbial and anti-inflammatory flavonoid constituents from the leaves of Lawsonia inermis

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20170613

Termination date: 20180203

CF01 Termination of patent right due to non-payment of annual fee