CN108997458A - Kaempferol-(4-O- methyl) glucoside compounds and its application in insecticide pesticide - Google Patents
Kaempferol-(4-O- methyl) glucoside compounds and its application in insecticide pesticide Download PDFInfo
- Publication number
- CN108997458A CN108997458A CN201810893981.5A CN201810893981A CN108997458A CN 108997458 A CN108997458 A CN 108997458A CN 201810893981 A CN201810893981 A CN 201810893981A CN 108997458 A CN108997458 A CN 108997458A
- Authority
- CN
- China
- Prior art keywords
- kaempferol
- methyl
- compound
- glucoside
- compounds
- 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
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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Saccharide Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to the methylated derivatives of two Kaempferol glucoside compounds, that is Kaempferol 3-O- β-D- (4-O- methyl) glucoside and Kaempferol 4'-O- β-D- (4-O- methyl) glucoside, two compound structure novelties have not been reported, in biological activity test, two compounds show different degrees of insecticidal activity, it is that its aglycon does not have, is with a wide range of applications.
Description
Technical field
The invention belongs to field of pesticides, and in particular to Kaempferol-(4-O- methyl) glucoside compounds and its kill
Purposes in worm drug.
Background technique
Kaempferol (kaempferol) is a kind of common natural flavonoid Secondary metabolites, is widely present in
In the roots of various plants, leaf and fruit.Kaempferol has anti-oxidant, anti-inflammatory, inhibits tumour growth and protection liver cell, inhibits
Platelet aggregation and adhesion isoreactivity, therefore get more and more people's extensive concerning.However, Kaempferol is only very slightly soluble in water, and
Metabolic stability in the mammalian body is poor, is easy to be influenced by from many factors of organism and the external world, leads to itself
Degradation, activity reduce, and greatly hinder its application.Glucosyl and methylation are that modification common in organism is anti-
It answers, thus it is possible to vary the physicochemical properties such as water solubility, stability of compound obtain more valuable to influence its biological effectiveness
Reactive compound.
The Kaempferol glycation product being currently known has glucoside, rhamnoside, lutinoside, rutinoside etc..According to
Research, glycoside Kaempferol are obviously reduced compared with its aglycon, oxidation resistant activity.Sannaphthol-3-O-rutinoside can obviously drop
Activity of cholinesterase in low blood and brain tissue, and excitatory amino acid mediator in hippocampus is reduced, improve acetyl in brain tissue
Choline and monoamine, inhibitory aminoacid neurotransmitter content, thus can be used for preparing the drug of prevention and treatment senile dementia disease.Mountain
How phenol -3-O- β-D-Glucose glycosides is to Escherichia coli, Pseudomonas aeruginosa, streptococcus lactis, staphylococcus aureus, bacillus subtilis
Certain inhibitory effect is all had, minimal inhibitory concentration (MIC) is respectively 250,250,250,125 and 125 μ g/mL.Some kaempferia galamgas
Phenose glycosides has the activity for inhibiting HDAC, such as Kaempferol -3-O- α-L- arabopyranose glycosides (54.46%), Kaempferol -3-O-
β-D- xylopyranose glucosides (45.86%), Kaempferol -3-O- β-D- glucopyranoside (43.01%), Kaempferol -3-O- β-D-
Acetyl group glucoside (39.61%) etc., activity are higher than its aglycon.But the rare report of the anti-insect activity of kaempferol derivative.Mountain
How glycosides is 3,7 rhamnosides (kaempferol-3,7-dirhamnoside) of Kaempferol, has anti-large white butterfly (Pieris
Brassicae activity).
Summary of the invention
The present invention carries glucosyltransferase heterologous expression vector PRS425m-IfUGT and oxygen transmethylase heterogenous expression
Body PXW06F-IfOMT is transferred to auxotrophic yeast receptor BJ5464 and carries out heterogenous expression, and carries out Kaempferol feeding, passes through
HPLC-HRMS detects kaempferol derivative.By increasing fermentation-scale, obtains and separated after enough extracts, purified, obtain
Kaempferol 7-O- β-D- (4-O- methyl) glucoside (compound 1), Kaempferol 3-O- β-D- (4-O- methyl) glucoside (are changed
Close object 2) and three kinds of Kaempferols of Kaempferol 4'-O- β-D- (4-O- methyl) glucoside (compound 3) (4-O- methyl) glucose
Glycoside derivates, wherein the structure of compound 2 and 3 has not been reported.
Therefore, the first purpose of the invention is to provide two kinds of Kaempferols (4-O- methyl) glucoside compounds (to change
Object 2 and 3) is closed, shown in chemical structure such as formula (1):
Correspondingly, the present invention provides above compound 2 and compound 3 as the application in insecticide.Thus also provide
Insecticide containing above-mentioned two compound.Preferably, desinsection, which refers to, kills bright and beautiful earworm or diamondback moth.
Experiments show that having beneficial technical effect.Specifically, mountain is had evaluated by hemocoel injection method
How phenol, Kaempferol glucoside compounds 4-6 and 1-3 pair of 4 age Mo of Kaempferol (4-O- methyl) glucoside compounds
The lethal and growth inhibition effect of phase bollworm.As the result is shown: compound 1-3 shows different degrees of under 20ng/g dosage
Insecticidal activity, lethality are up to 85% (p < 0.05)；Compound 1-3 is able to suppress Growth of The Cotton Bollworm under 2ng/g dosage, and leads
Bollworm is caused to generate food refusal effect.In addition, the present invention is dynamic by 1-3 pair of lactation of compound of in vitro cytotoxic effect experimental evaluation
The growth inhibition effect of object cell.As the result is shown: 1-3 pair of four kinds of source of people tumour cell of compound (A549, HepG2, HeLa and
MCF-7) and a kind of African green monkey kidney cell (Vero) does not show apparent growth inhibition effect (IC50>=25.0 μM), it says
1-3 pair of human body of bright compound has good safety.Therefore, compound 1-3 is expected to develop into environmentally protective, high-efficiency low-toxicity
Insecticide pesticide has broad application prospect.
Detailed description of the invention
Fig. 1 Kaempferol generates the chromatogram of 3 kinds of sugared methylated derivatives after bioconversion.
Fig. 2 Kaempferol generates the mass spectrogram of a kind of glycosylated derivative and 3 kinds of sugared methylated derivatives after bioconversion.
The cause of Fig. 3 Kaempferol and its glucoside analog derivative under 20ng/ (g body weight) dosage to bollworm
Dead effect.
Fig. 4 Kaempferol and its glucoside analog derivative are under 2ng/ (g body weight) dosage to bollworm weight
The influence of growth.
Fig. 5 Kaempferol and its glucoside analog derivative are under 20ng/ (g body weight) dosage to the shadow of bollworm
It rings.
The lethal effect of Fig. 6 Kaempferol and its glucoside analog derivative to 1 age diamondback moth.
The lethal work of Fig. 7 Kaempferol and its glucoside analog derivative to 3 age diamondback moths.
Fig. 8 Kaempferol and its glucoside analog derivative influence the weight of 3 age diamondback moths.
Specific embodiment
Come that the present invention is furture elucidated below by the detailed description of specific embodiment, but is not to limit of the invention
System, only illustrates.
The application glycosyl transferase recombinant vector PRS425m-IfUGT of embodiment 1 and O- transmethylase recombinant vector
PXW06F-IfOMT is realized to methylate to the glycosyl of Kaempferol and be modified
1.1 instruments and material
Bacterial strain uses therefor and carrier in experiment: fumosorosea bacterium Isaria fumosorosea ACCC37775 and yeast
Bacterium S.cerevisiae BJ5464-NpgA, Yeast expression carrier PRS425m-IfUGT and PXW06F-IfOMT, derive from
Biotechnology institute of Academy of Agricultural Sciences of state, is voluntarily saved by the present inventor laboratory.Testing agents useful for same is the pure production of domestic analysis
Product.Culture medium: Escherichia coli culture medium is LB culture medium (1% peptone, 0.5% yeast extract, 1%NaCl, pH7.0).
SC--Leu defect culture medium (1% glucose, 6.7%DifcoTM Yeast Nitrogen Base w/o Amino Acids、-
Leu/-Trp DO Supplement).YPD culture medium (1% yeast extract, 2%Peptone peptone, 2% glucose).YPD is low
2% agar powder is added if solid medium processed in sugar culture-medium (1% yeast extract, 2%Peptone peptone, 1% glucose).
High performance liquid chromatograph be Agilent 1290Infinity II, chromatographic column RRHD Eclipse Plus C18,
4.6x100mm。
Other test method without specific conditions in embodiment, conventionally carry out, and molecular cloning presses (New
York:Cold Spring Harbor Laboratory Press, 1989) condition described in laboratory manual, or according to system
Make condition proposed by manufacturer.
1.2 experimental method
Two-step fermentation technology is taken, suitable yeast transformant thallus is seeded to corresponding 25-mL first-Leu/-
In Trp liquid defect culture medium, 30 DEG C, 200rmin-1 culture 16h or so add YPD low sugar culture medium 25ml, simultaneously
5mg Kaempferol sterling is separately added into continue to cultivate 48h；It is extracted with ethyl acetate tunning, the ratio of ethyl acetate and fermentation liquid
Example is 1:1, i.e., extracts tunning with the ethyl acetate of 50ml；Rotary Evaporators recycle ethyl acetate dry extract, 1ml first
Alcohol redissolves extract.
Above-mentioned gained tunning is used after high speed centrifugation and passes through efficient liquid phase (HPLC) chromatography and high resolution mass spectrum
(HRMS/MS) it detects.HPLC testing conditions are as follows: use acetonitrile-water to carry out gradient elution for mobile phase, condition of gradient elution:
Condition of gradient elution: 0~5min, acetonitrile is from 10% → 50%；5~10min, acetonitrile is from 50% → 95%；10~12min, second
Nitrile is 95%；12~12.5min, acetonitrile is from 95% → 10%；12.5~13min, acetonitrile 10%.Flow velocity 0.5mLmin-
1, Detection wavelength 300nm.HRMS/MS testing conditions are as follows: negative ion mode, collision energy 25V.
1.3 experimental results and analysis
HPLC is analyzed as the result is shown: feeding raw material Kaempferol is almost converted into obtain four kinds of derivatives.Pass through
HRMS analysis is found, in four after conversion peak, the molecular weight of 1 compound of peak has more 162amu than the molecular weight of Kaempferol, is pushed away
Surveying is glucosyl product, and the molecular weight of peak 2-4 compound has more 176amu than the molecular weight of Kaempferol, thus it is speculated that is methyl Portugal
Grape glycation product.It is found by HRMS/MS analysis, when collision energy is 15eV, the second order ms base peak of peak 2-4 compound
It is Kaempferol [M+H]+Molecular weight, find Kaempferol methylation after [M+H]+Molecular weight, illustrate that glycosyl is same with methyl
When fall off, therefore methyl modification is very likely on the hydroxyl of glycosyl, rather than on the hydroxyl of Kaempferol.
Recombinant bacterial strain tunning chromatogram and mass spectrogram are shown in Fig. 1 and Fig. 2.
The extraction separation of 2 compound 1-3 of embodiment and Structural Identification
2.1 instruments and material
Solvent for use chloroform, methanol, ethyl acetate are the production of Beijing chemical reagent factory in experiment, are that analysis is pure.Chromatography
Pure acetonitrile is the production of Fisher Chemical company.Column chromatography silica gel is that Haiyang Chemical Plant, Qingdao produces (200~300 mesh).It is thin
Layer silica gel column chromatography plate is the production of Yantai Huang business silica gel development experiments factory.BUCHI R-300 type Rotary Evaporators, BUCHI I-300
Type touch-control central control unit, BUCHI V-300 type PTFE film formula vacuum pump, BUCHI B-300 type electric-heated thermostatic water bath,
It is produced by BUCHI company of Switzerland.Low-temperature cooling fluid circulating pump knows that the reliable technical device Co., Ltd that tests produces by Shanghai.Half prepares
High performance liquid chromatograph be Agilent 1260Infinity II, C18 chromatographic column be Agilent ZORBAX RX-C18 (5 μm, 9.4
×250mm).HRESI-MS instrument is Agilent MS 6530Q-TOF type mass spectrograph, direct injected measurement.Nuclear magnetic resoance spectrum spectrum
It is measured with Bruker AVIII 400M type NMR spectrometer with superconducting magnet, is demarcated with deuterated dimethyl sulfoxide residual solvent peak, it is deuterated
Dimethyl sulfoxide is U.S. Cambridge company (CIL) production.
2.2 experimental method
The isometric ethyl acetate of 10L fermentation liquid extracts three times, and organic phase obtains total medicinal extract (1.9g) after being concentrated under reduced pressure.Always
Medicinal extract is successively eluted through normal-phase silica gel column chromatography with the chloroform-methanol that volume ratio is 100:0,98:2,95:5 and 90:10.
Collect 95:5 elution fraction, upper half preparative high-performance liquid chromatographic, using volume ratio for 23:77 acetonitrile-aqueous solution as mobile phase,
Isolated compound 1 (20mg, tR=12.2min), compound 2 (32mg, tR=10.1min) and compound 3 (50mg, tR=
14.2min)。
2.3 experimental results and analysis
By parsing high resolution mass spectrum, a peacekeeping ID NMR speetna, the structure such as formula (1) of compound 1-3 is identified
It is shown.Wherein, compound 1 is reported Kaempferol 7-O- β-D- (4-O- methyl) glucoside, and compound 2 and 3 is respectively
Kaempferol 3-O- β-D- (4-O- methyl) glucoside and Kaempferol 4'-O- β-D- (4-O- methyl) glucoside, the structure is not
It appears in the newspapers.The Structural Identification data of compound 1-3 are as follows:
Compound 1: high resolution mass spectrum m/z 461.1009 [M-H]-, calcd.461.1089, molecular formula C22H22O11；1H
NMR (400MHz) and13C NMR (400MHz) attribution data is as shown in table 1.
Compound 2: high resolution mass spectrum m/z 461.1114 [M-H]-, calcd.461.1089, molecular formula C22H22O11；1H
NMR (400MHz) and13C NMR (400MHz) attribution data is as shown in table 1.
Compound 3: high resolution mass spectrum m/z 461.1106 [M-H]-, calcd.461.1089, molecular formula C22H22O11；1H
NMR (400MHz) and13C NMR (400MHz) attribution data is as shown in table 1.
The nuclear magnetic resonance data of 1. compound 1-3 of table (test solvent is deuterated dimethyl sulfoxide)
The cytotoxic activity of 3 Kaempferol of embodiment and its glucoside compound
3.1 instruments and material
Microplate reader is Genois microplate reader (Tecan GENios, Swizerland)；Four kinds of source of people are swollen
Tumor cell strain, that is, typeⅡ pneumocyte, human hepatoma HepG2 cell, HeLa Cells, MCF-7 Human Breast Cancer Cells with
And African green monkey kidney epidermis Vero cell is purchased from Kunming Institute of Zoology, Chinese Academy of Sciences；Fetal calf serum FBS, RPMI1640 training
Nutrient solution, DMEM culture solution are purchased from Gibco, USA；3- (4,5- dimethylthiazole -2) -2,5- diphenyltetrazolium bromide bromide (MTT) purchase
From Amresco, USA.
3.2 experimental method
TypeⅡ pneumocyte, human hepatoma HepG2 cell, HeLa Cells, the human milk gland of logarithmic growth phase
Cancer MCF-7 cell, African green monkey kidney epidermis Vero cell are added in 96 orifice plates, and about 5000 cells are contained in every hole.It adds not
With the Kaempferol and compound 1-6 of concentration, and using adriamycin as positive control, not to be loaded the cell holes of product as a control group,
Every group sets 4 parallel holes, is placed in carbon dioxide incubator and cultivates 72 hours for 37 DEG C, experiment terminates first 4 hours 20 μ L of addition
MTT (5mg/mL) solution, is further cultured for 4 hours, 150 μ L DMSO is added after discarding culture solution, in enzyme-linked detection after dissolution to be crystallized
The OD value in every hole under 570nm wavelength is detected on instrument.Growth inhibition ratio is found out by following equation, then is found out by SPSS (17.0) software
Half-inhibitory concentration (IC50Value).It the results are shown in Table 2, wherein IC50It is indicated with Mean ± S.E.M.
3.2 experimental results and analysis
By the result in table 2 as it can be seen that 1-3 pair of mammalian cell of compound does not show apparent cytotoxicity.
Growth of tumour cell inhibitory activity (the IC of 2. Kaempferol of table and its glycosides derivative50,μM)
4 Kaempferol of embodiment and its glucoside compound test bollworm killing ability
4.1 experiment purpose
By hemocoel injection method, Kaempferol and its 6 kinds of glucoside compounds are tested and compared to Growth of The Cotton Bollworm
It influences, shows the insecticidal activity of compound 1-6.
4.2 experimental method
First with methanol by six kinds of diluted chemical compounds at the mother liquor of 100 μ g/mL, be diluted with water to 10 μ g/mL (20ng/ later
(g body weight)) and the solution of 1 μ g/mL (2ng/ (g body weight)) handled.Select the cotton boll in 4 latter stages in age
Worm carries out injection treatment, and every cephalont injects 2 μ L, compared with 10% methanol.10 cephalonts, 3 repetitions are injected in every processing.After 5d
Statistical result simultaneously samples.
4.3 experimental results and analysis
Under the dosage of 20ng/ (g body weight), Kaempferol and its glucosyl derivative (compound 4-6)
Significant insecticidal activity is not shown, bollworm lethality is suitable with blank control；And the compound after the modification that methylates unexpectedly
1-3 then shows different degrees of insecticidal action.
Under the dosage of 2ng/ (g body weight), Kaempferol and its glucoside compounds (1-6) are not showed
Apparent lethal effect out, but compound 1-6 causes insect growth slow to varying degrees, and compound 1-3 makes insect
Show food refusal effect.
Kaempferol and its glucoside analog derivative are under 20ng/ (g body weight) dosage to the lethal of bollworm
Fig. 3 is shown in effect.
Kaempferol and its glucoside analog derivative are under 2ng/ (g body weight) dosage to bollworm body weight increase
Effect see Fig. 4.
What Kaempferol and its glucoside analog derivative influenced bollworm under 20ng/ (g body weight) dosage
Picture is shown in Fig. 5.
5 Kaempferol of embodiment and its glucoside compound test diamondback moth killing ability
5.1 experiment purpose
Blade and feeding are smeared by compound, tests and compare Kaempferol and its 6 kinds of glucoside compounds to small
The influence of diamond-back moth growth, shows the insecticidal activity of compound 1-6.
5.2 experimental method
Kaempferol and its 6 kinds of derivatives are dissolved in DMSO, the solution of 10mM is configured to.The solution of 10 μ l is added to
In the Triton X-100 aqueous solution of 990 μ l 1mL 0.1%, then ultimate density 0.1mM is evenly coated on cabbage leaves,
It is put into after drying in the culture dish for being lined with filter paper, accesses 1 age or 3 age diamondback moth larvaes.The death of test worm is checked after 72h
Rate.15 test insects of each processing, 3 repetitions.
5.3 experimental results and analysis
In addition to compound 5, other 5 kinds of glycosylated derivatives are all remarkably higher than control group to the insecticidal activity of 1 age diamondback moth
(Kaempferol) (p < 0.05).
For 3 age diamondback moths, the lower diamondback moth death rate of compound 1-6 processing be increased, but difference is not compared with the control
Significantly；Compound 1 and compound 2 cause diamondback moth weight to significantly reduce (p < 0.05)
Kaempferol and its glucoside analog derivative are shown in Fig. 6 to the lethal effect of 1 age diamondback moth.
Kaempferol and its glucoside analog derivative are shown in Fig. 7 to the lethal effect of 3 age diamondback moths.
Kaempferol and its glucoside analog derivative are shown in Fig. 8 to the influence of the weight of 3 age diamondback moths.
Claims (6)
1. a kind of Kaempferol (4-O- methyl) glucoside compounds are Kaempferol 3-O- β-D- (4-O- methyl) glucose
Glycosides, structural formula are as follows:
2. a kind of Kaempferol (4-O- methyl) glucoside compounds are Kaempferol 4'-O- β-D- (4-O- methyl) grapes
Glucosides, structure are as follows:
3. Kaempferol (4-O- methyl) glucoside compounds as claimed in claim 1 or 2 are as answering in insecticide
With.
4. application as claimed in claim 3, which is characterized in that desinsection, which refers to, kills bright and beautiful earworm or diamondback moth.
5. containing the insecticide of Kaempferol as claimed in claim 1 or 2 (4-O- methyl) glucoside compounds.
6. application as claimed in claim 5, which is characterized in that desinsection, which refers to, kills bright and beautiful earworm or diamondback moth.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810893981.5A CN108997458B (en) | 2018-08-08 | 2018-08-08 | Kaempferol- (4-O-methyl) glucoside compound and application thereof in pesticide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810893981.5A CN108997458B (en) | 2018-08-08 | 2018-08-08 | Kaempferol- (4-O-methyl) glucoside compound and application thereof in pesticide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108997458A true CN108997458A (en) | 2018-12-14 |
| CN108997458B CN108997458B (en) | 2020-12-18 |
Family
ID=64595674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810893981.5A Active CN108997458B (en) | 2018-08-08 | 2018-08-08 | Kaempferol- (4-O-methyl) glucoside compound and application thereof in pesticide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108997458B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109939100A (en) * | 2019-04-22 | 2019-06-28 | 井冈山大学 | Utilize the acetylcholine enzyme inhibitor of close plumage rhizome of cyrtomium preparation, preparation method and application |
| CN113068697A (en) * | 2021-04-07 | 2021-07-06 | 中国林业科学研究院森林生态环境与保护研究所 | Application of sinapine aldehyde glucoside in preparation of narrow-leaved Croton wax product and insect-resistant breeding |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107094813A (en) * | 2017-03-09 | 2017-08-29 | 海门市琴键农产品有限公司 | A kind of insecticide |
-
2018
- 2018-08-08 CN CN201810893981.5A patent/CN108997458B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107094813A (en) * | 2017-03-09 | 2017-08-29 | 海门市琴键农产品有限公司 | A kind of insecticide |
Non-Patent Citations (2)
| Title |
|---|
| 张雷红: "《天然药物化学》", 31 January 2017 * |
| 黄继光，等: "从羽裂蟹甲草分离的 9 种化合物的杀虫活性", 《华南农业大学学报》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109939100A (en) * | 2019-04-22 | 2019-06-28 | 井冈山大学 | Utilize the acetylcholine enzyme inhibitor of close plumage rhizome of cyrtomium preparation, preparation method and application |
| CN109939100B (en) * | 2019-04-22 | 2022-04-19 | 井冈山大学 | Acetylcholine enzyme inhibitor prepared from Cyrtomium fortunei, preparation method and application |
| CN113068697A (en) * | 2021-04-07 | 2021-07-06 | 中国林业科学研究院森林生态环境与保护研究所 | Application of sinapine aldehyde glucoside in preparation of narrow-leaved Croton wax product and insect-resistant breeding |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108997458B (en) | 2020-12-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Negi et al. | In vitro antimicrobial activity of Acacia catechu and its phytochemical analysis | |
| Djoukeng et al. | Antibacterial triterpenes from Syzygium guineense (Myrtaceae) | |
| Park et al. | Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides | |
| Hazni et al. | Phytochemical constituents from Cassia alata with inhibition against methicillin-resistant Staphylococcus aureus (MRSA) | |
| CN104761565B (en) | Myrtle ketone compound and application thereof in preparation of antibacterial medicines | |
| Abdel-Wahab et al. | Induction of secondary metabolites from the marine-derived fungus Aspergillus versicolor through co-cultivation with Bacillus subtilis | |
| Joshi et al. | In vitro cytotoxicity, antimicrobial, and metal-chelating activity of triterpene saponins from tea seed grown in Kangra valley, India | |
| Ebrahim et al. | Embellicines A and B: Absolute configuration and NF-κB transcriptional inhibitory activity | |
| Heng et al. | Analysis of the bioactive components of Sapindus saponins | |
| Zhang et al. | Purification and partial characterization of bacillomycin L produced by Bacillus amyloliquefaciens K103 from lemon | |
| Menezes et al. | Pigment production by Fusarium solani BRM054066 and determination of antioxidant and anti-inflammatory properties | |
| Qiu et al. | Kaempferol separated from Camellia oleifera meal by high-speed countercurrent chromatography for antibacterial application | |
| CN108997458A (en) | Kaempferol-(4-O- methyl) glucoside compounds and its application in insecticide pesticide | |
| Kapoor et al. | Enhanced Production of Phenolic Compounds in Compact Callus Aggregate Suspension Cultures of Rhodiola imbricata Edgew. | |
| Abdou et al. | Terezine E, bioactive prenylated tryptophan analogue from an endophyte of Centaurea stoebe | |
| Gir6nb et al. | An antifungal compound from zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJ Solanum nigrescens | |
| Nakashima et al. | Nanaomycin H: A new nanaomycin analog | |
| Rajendran et al. | Isolation and quantification of antimalarial N-alkylamides from flower-head derived in vitro callus cultures of Spilanthes paniculata | |
| CN105504021B (en) | A kind of Peptaibol antibacterial peptide compounds and its preparation method and application | |
| Leal et al. | Ceanothane and lupane type triterpenes from Zizyphus joazeiro–an anti-staphylococcal evaluation | |
| Kekuda et al. | Characterization and antibacterial activity of a glycoside antibiotic from Streptomyces variabilis PO-178 | |
| Abrol et al. | Mutation, chemoprofiling, dereplication, and isolation of natural products from Penicillium oxalicum | |
| CN106632230B (en) | A kind of marine fungi pawl aspergillus bromo contracting phenol naphthenic acid ether compound and its preparation method and application | |
| US20230313247A1 (en) | Kind of antimycin compound and methods of making and using it | |
| CN109090115A (en) | A kind of application of Kaempferol (4-O- methyl) glucoside compounds in pest-resistant agent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |