CN112778262B - Plant-derived quassin and preparation method and application thereof - Google Patents
Plant-derived quassin and preparation method and application thereof Download PDFInfo
- Publication number
- CN112778262B CN112778262B CN202110029779.XA CN202110029779A CN112778262B CN 112778262 B CN112778262 B CN 112778262B CN 202110029779 A CN202110029779 A CN 202110029779A CN 112778262 B CN112778262 B CN 112778262B
- Authority
- CN
- China
- Prior art keywords
- plant
- compound
- derived
- quassin
- fre
- 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.)
- Active
Links
Images
Classifications
-
- 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
-
- 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
-
- 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
- A01N43/24—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 two or more hetero atoms
- A01N43/26—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 two or more hetero atoms five-membered rings
- A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a plant source quassin and a preparation method and application thereof. The preparation method of the quassin comprises the following steps: soaking and extracting evergreen bitter tree leaves with ethanol, and concentrating under reduced pressure to obtain crude extract; separating the extract with macroporous resin, silica gel, gel and semi-prepared high performance liquid chromatography column to obtain the compound. The compound has obvious inhibition activity on rhizoctonia solani, fusarium oxysporum, fusarium graminearum, penicillium citrinum, phytophthora cucumis and the like. Therefore, the compound can be used as a novel botanical antibacterial candidate drug.
Description
Technical Field
The invention belongs to the technical field of biochemical engineering, and particularly relates to plant-derived quassin, and a preparation method and application thereof.
Background
The pesticide is an indispensable production data in agricultural production and agricultural economic development, and is a major strategic substance related to global grain safety, food safety and ecological safety. Has considerable effects on preventing and controlling crop diseases, insect pests and weeds, ensuring the yield and quality of agricultural products, ensuring food safety and the like. According to statistics, the use of the pesticide can recover 30 to 40 percent of the loss of the total crop production in the world every year. The ecological conditions of China are complex, the cultivation system is various, and the ecological environment-friendly cultivation method belongs to the countries with multiple pests, frequent pests and repeated pests. The total planting area of crops suffering from diseases, insect pests and weeds in China is up to 12190 million hectares every year. Therefore, in the past decades, chemical pesticides play an important role in controlling crop diseases, pests and weeds, guaranteeing and improving the yield and quality of grains, and guaranteeing food safety.
However, long-term unreasonable use of chemical pesticides causes a series of serious environmental and social problems, such as serious soil hardening acidification, enhanced drug resistance, serious exceeding of pesticide residue, ecological balance destruction, environmental pollution and other hidden dangers affecting human health. Particularly, the 'green technology barrier' caused by pesticide residues becomes a prominent problem for limiting the export trade of agricultural products in China at present. Therefore, the development of green pesticides with high biological activity, high selectivity, low residue, easy degradation and no pollution is urgent. The botanical pesticide has the advantages of natural active ingredients, no toxicity, no environmental pollution, difficult generation of drug resistance, safety to beneficial organisms and the like, and is an important research direction for green pesticides.
The botanical pesticides can be divided into: botanical insecticides, botanical fungicides, botanical antivirals, botanical herbicides, and the like. At present, botanical insecticides are a class of botanical pesticides which are relatively successfully researched, and mature commodities are sold on the market and applied to agricultural production. Such as azadirachtin, saponin nicotine soluble emulsion, rotenone emulsifiable concentrate, bisultrine aqueous solution, fennel artemisin aqueous solution, oleic acid nicotine, etc. However, statistics indicate that about 85% of plant diseases are caused by fungi, such as sclerotinia, fusarium, pseudosporium, brucella, phytophthora, pythium, and the like. Compared with botanical insecticides, the research on botanical fungicides is much less, and most research is limited to the antibacterial activity of plant extracts, and a botanical antibacterial agent really used in agricultural production is not available. Therefore, research and development of novel botanical antibacterial agents are urgent.
Evergreen quassia (Picrasmajavanica) is an evergreen tree of quassia of quassiaceae, and is mainly distributed in tropical regions of asia, such as indonesia, india and burma. The method is widely distributed in the places of Xishuangbanna, jingdong and the like in China. In folk, the decoction of the bark of the Chinese medicinal herb can be used as a substitute of quinine for treating malaria. The approximate amount of the tree leaves in Java and other places is also used for treating wounds by squeezing juice. The secondary metabolite of the plant is reported in literature to be mainly a quassin compound and has the activities of resisting tumor, inflammation, virus, neuroprotection and the like. However, no reports have been made on the activity of the quassinoids against phytopathogenic fungi.
Disclosure of Invention
One of the purposes of the present invention is to provide a novel plant-derived quassin compound Pj-1, the structural formula of which is shown as the following formula:
the second purpose of the invention is to provide a method for preparing a novel quassin compound Pj-1, which is characterized in that the compound is obtained from leaves of evergreen quassia, and specifically, the leaves of evergreen quassia are crushed and soaked by ethanol (95%) to obtain leachate, the leachate is decompressed and distilled to remove a solvent to obtain a crude extract, the crude extract is dissolved in hot water at 50 ℃, then ethyl acetate is used for extraction to obtain an ethyl acetate extract, and then macroporous resin, silica gel, gel and semi-prepared high performance liquid chromatography columns are used for separation to obtain the compound. The method comprises the following steps:
s1, crushing the leaves of evergreen bitter trees, and soaking the leaves in ethanol (95%) for 3 times, wherein 7 days are taken for each time, so as to obtain a leaching solution.
S2, distilling the leachate under reduced pressure to remove the solvent, thereby obtaining a crude extract.
And S3, dissolving the crude extract in hot water at 50 ℃, and extracting with ethyl acetate to obtain an ethyl acetate extract.
And S4, separating the ethyl acetate extract by using macroporous resin, performing gradient elution by using 30%, 50%, 80% and 95% ethanol as mobile phases respectively, and finally obtaining 4 components Fre-1-Fre-4 by TLC analysis.
S5, isolating Fre-2 by normal phase silica gel column chromatography, gradient elution with petroleum ether/acetone mixed solvent as mobile phase, and detecting by TLC, wherein the volume ratio is 50.
S6, isolating Fre-2.4 using Sephadex LH-20, isocratically eluting with methanol/chloroform =1 as a mobile phase, then separating with normal phase silica gel column chromatography, and performing gradient elution with a chloroform/methanol mixed solvent as a mobile phase at a volume ratio of 20.
S7, separation of Fre-2.4.4 using Sephadex LH-20, isocratic washing with methanol/chloroform =1 as mobile phaseAnd then purified by high performance liquid chromatography, and isocratic eluted with methanol/water =43 as a mobile phase at a flow rate of 2.0 mL/min to obtain the target compound Pj-1,t R ＝35.4min。
The liquid chromatograph of the semi-preparative liquid chromatogram in the S7 is Waters 1525, the mobile phase is methanol-water, the flow rate is 2mL/min, the detector is a Waters 2998 photodiode array detector, the detection wavelength is 200-400nm, the chromatographic column is a Waters Sunfire C18 semi-preparative column, and the specification is 10 multiplied by 250mm.
The invention also aims to provide the compound Pj-1 with good effect of inhibiting plant pathogenic fungi and application in preparing antibacterial drugs.
The invention has the beneficial effects that: a quassinoid is isolated from the leaves of the evergreen quassia (Picrasmajavanica). The compound has obvious inhibition activity on Rhizoctonia solani (Rhizoctonia solani), fusarium oxysporum (Fusarium oxysporum f.sp.niveum), fusarium graminearum (Fusarium graminearum), penicillium citrinum (Penicillium citrinum), phytophthora cucumerinum (Phytophthora melonis) and the like. Therefore, the compound can be used as a novel plant source antibacterial candidate drug and provides scientific basis for reasonable development and utilization of evergreen bitter tree resources.
Drawings
FIG. 1 is a drawing of compound Pj-1 1 HNMR spectra;
FIG. 2 is a drawing of compound Pj-1 13 A CNMR spectrum;
FIG. 3 is an HMBC spectrum of compound Pj-1;
FIG. 4 is an IR spectrum of the compound Pj-1;
FIG. 5 is an HRESIMS spectrum of compound Pj-1;
Detailed Description
The technical solution of the present invention will be further specifically described below by way of specific examples.
In the present invention, the raw materials and equipment used are commercially available or commonly used in the art, unless otherwise specified. The methods in the following examples are conventional in the art unless otherwise specified.
Example 1:
the compound Pj-1 is separated and extracted from the leaves of evergreen picrasma quassioides (Picrasmajavanica), and the extraction process is as follows:
crushing 10kg of evergreen bitter tree leaves collected from Xishuangbanna, soaking and extracting for 3 times at room temperature by using 95% ethanol for 7 days each time, concentrating under reduced pressure to obtain 380g of total extract, dissolving the total extract in hot water of 500 ℃, and extracting by using ethyl acetate to obtain an ethyl acetate extract. Separating the ethyl acetate extract with macroporous resin, gradient eluting with 30%, 50%, 80%, and 95% ethanol as mobile phase, and analyzing by TLC to obtain 4 fractions Fre-1-Fre-4. Fre-2 was separated by normal phase silica gel column chromatography, gradient elution was performed using a petroleum ether/acetone mixed solvent as a mobile phase, and the volume ratio was 50. The procedure of separation by Sephadex LH-20, isocratic elution with methanol/chloroform =1 as a mobile phase, separation by normal phase silica gel column chromatography, gradient elution with chloroform/methanol mixed solvent as a mobile phase at a volume ratio of 20. Fre-2.4.4 was separated using Sephadex LH-20, isocratic eluted with methanol/chloroform =1 as the mobile phase, then purified by high performance liquid chromatography, isocratic eluted with methanol/water =43 as the mobile phase at a flow rate of 2.0 mL/min to give the target compound, t R And =35.4min. The compound was identified as Pj-1 by integrated spectroscopic analysis.
Example 2
The plant-derived quassin compound can also be obtained from leaf, stem, bark, root, etc. of evergreen quassia. Meanwhile, other lignin molecules with antibacterial effect, namely the compounds Pj-2-Pj-5 can be provided, but the experimental comparison shows that Pj-1 is the optimized compound, and the structural formula of the compounds Pj-2-Pj-5 is as follows:
other compounds were prepared by the following method:
crushing 10kg of evergreen bitter tree stems (or bark, root and leaves are the most preferred) collected from Xishuangbanna, soaking and extracting with 95% ethanol at room temperature for 3 times, each time for 7 days, concentrating under reduced pressure to obtain 380g of total extract, dissolving in hot water of 50 ℃, and extracting with ethyl acetate to obtain an ethyl acetate extract. Separating the ethyl acetate extract with macroporous resin, gradient eluting with 30%, 50%, 80%, and 95% ethanol as mobile phase, and analyzing by TLC to obtain 4 fractions Fre-1-Fre-4. Fre-2 was separated by normal phase silica gel column chromatography, gradient elution was performed using a petroleum ether/acetone mixed solvent as a mobile phase, and the volume ratio was 50. The procedure of separation by Sephadex LH-20, isocratic elution with methanol/chloroform =1 as a mobile phase, separation by normal phase silica gel column chromatography, gradient elution with chloroform/methanol mixed solvent as a mobile phase at a volume ratio of 20. After separation by Sephadex LH-20 using methanol/chloroform =1 as a mobile phase, fre-2.4.4 was subjected to isocratic elution by high performance liquid chromatography using methanol/water =43 as a mobile phase at a flow rate of 2.0 mL/min to obtain the target compound Pj-1,t R And =35.4min. Fre-2.4.2 was purified by high performance liquid chromatography, and isocratic elution was performed using methanol/water =35 as a mobile phase at a flow rate of 2.0 mL/min, to obtain the objective compound Pj-3 (t R =42.1 min) and Pj-4 (t) R =41.2 min). Fre-2.4.3 was purified by high performance liquid chromatography, and isocratic elution was performed using methanol/water =40 as a mobile phase at a flow rate of 2.0 mL/min, to obtain the target compound Pj-2 (t R =35.4 min) and Pj-5 (t) R =37.32 min). The structure of the compound is determined by comprehensive spectrum analysis.
Example 3 Activity test
And (3) carrying out in-vitro antifungal activity detection on the target compound by adopting a mycelium growth inhibition method. The specific method comprises the following steps: the 5 plant pathogenic fungi used for the test were inoculated on Potato Dextrose Agar (PDA) and cultured in an incubator at 28 ℃ for 4 days to obtain a vigorously growing hypha. Respectively dissolving the compound Pj-1-Pj-5 and carbendazim (positive control) in DMSO-H 2 O (v: v = 1), and then mixed with Potato Dextrose Agar (PDA) medium to finally obtain a mixture of 50 μ g/mL. The above mixture was poured into 6cm sterile petri dishes, and 6mL of each dish was poured to prepare a PDA plate containing the test compound Pj-1-Pj-5 or carbendazim. The cultured hyphae of each pathogen were cut into small pieces of 5mm in diameter and placed in the center of each PDA plate containing the test compound Pj-1-Pj-5 or carbendazim, while 5mm different hyphae small pieces were also placed in the center of the PDA plate without any drug as blank controls, with three replicates per experiment. All the hypha-containing PDA plates were incubated in an incubator at 28 ℃ for 48 hours. The diameter (mm) of each colony was measured by the cross method in the (T) and blank (C) culture dishes treated with the test compounds Pj-1 to Pj-5 or carbendazim, respectively, and the inhibition ratio (I) was calculated using the following formula: i (%) = [ (C-T)/C]×100。
TABLE 1 inhibitory Activity of Compound Pj-1-Pj-5 against 5 plant pathogenic fungi at 50. Mu.g/mL
TABLE 2 NMR data for Compound Pj-1 (600M, CDCl 3 )
Compound Pj-1 other physicochemical data: a colorless oil.
IR(KBr)ν max 3376, 2924,1721,1602,1383,1095,1044,792cm -1 ；HRESIMS m/z 417.1878[M+Na] + (calcd for C 21 H 30 O 7 Na,417.1884)。
The experimental result shows that the compound Pj-1-Pj-5 has certain inhibition effect on 5 tested plant pathogenic fungi. Wherein, the compound Pj-1 has the most obvious inhibition effect on 5 tested plant pathogenic fungi, and the inhibition rate ranges from 70.6 percent to 82.9 percent. In particular, pj-1 has higher inhibitory activity against Fusarium oxysporum (sp. Niveum) and Fusarium graminearum (Fusarium graminearum) than that of the positive control drug carbendazim. Meanwhile, the inhibitory activity of Pj-1 on Rhizoctonia solani (Rhizoctonia solani), penicillium citrinum (Penicillium citrinum) and Phytophthora cucumerinum (Phytophtora melonis) is equivalent to that of a positive control medicament, carbendazim. These results indicate that Pj-1 has the potential to be deeply developed into botanical antibacterial drugs.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, improvement and the like made within the content and principle of the present invention shall be included in the protection scope of the present invention.
Claims (7)
1. A preparation method of a plant-derived medicament for inhibiting plant pathogenic fungi is characterized in that the plant-derived quassin is used as a candidate molecule, and the structural formula of the plant-derived quassin is as follows:
2. the method for preparing a plant pathogenic fungus inhibiting medicine according to claim 1, wherein said quassin compound is obtained from the leaves of quassia virescens.
3. The preparation method of the plant-derived medicament for inhibiting plant pathogenic fungi according to claim 1, is characterized by comprising the following steps: soaking the leaves of evergreen tape tree in 95% ethanol, and concentrating under reduced pressure to obtain crude extract; separating the extract with macroporous resin, silica gel, gel and high performance liquid chromatography to obtain the compound.
4. The preparation method of the plant-derived drug for inhibiting plant pathogenic fungi according to claim 3, is characterized by comprising the following steps:
s1, crushing leaves of evergreen tape trees, and soaking the leaves in 95% ethanol for 3 times, wherein 7 days are taken for each time to obtain a leaching solution;
s2, distilling the leachate under reduced pressure to remove the solvent, thereby obtaining a crude extract;
s3, dissolving the crude extract in hot water at 50 ℃, and extracting with ethyl acetate to obtain an ethyl acetate extract;
s4, separating the ethyl acetate extract by using macroporous resin, performing gradient elution by using 30%, 50%, 80% and 95% ethanol as mobile phases respectively, and finally obtaining 4 components Fre-1-Fre-4 by TLC analysis;
s5, separating Fre-2 by using normal-phase silica gel column chromatography, performing gradient elution by using a petroleum ether/acetone mixed solvent as a mobile phase, wherein the volume ratio is 50;
s6, separating Fre-2.4 by using Sephadex LH-20, performing isocratic elution by using a mixed solvent of methanol/chloroform with the volume ratio of 1 as a mobile phase, then performing separation by using normal-phase silica gel column chromatography, performing gradient elution by using a mixed solvent of chloroform/methanol as a mobile phase, wherein the volume ratio is 20;
s7, separating Fre-2.4.4 by using Sephadex LH-20, performing isocratic elution by using a mixed solvent with a methanol/chloroform volume ratio of 1 R ＝35.4min。
5. The method according to claim 4, wherein the HPLC of S7 is Waters 1525, the mobile phase is methanol-water, the flow rate is 2mL/min, the detector is a Waters 2998 photodiode array detector, the detection wavelength is 200-400nm, and the chromatographic column is a Waters Sunfire C18 semi-preparative column with a specification of 10X 250mm.
6. Use of a plant-derived medicament for the inhibition of phytopathogenic fungi, obtained by the process according to claim 1, and for the preparation of a medicament against phytopathogenic fungi.
7. A plant-derived quassin compound characterized by: the formula is Pj-1 in claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110029779.XA CN112778262B (en) | 2021-01-11 | 2021-01-11 | Plant-derived quassin and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110029779.XA CN112778262B (en) | 2021-01-11 | 2021-01-11 | Plant-derived quassin and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112778262A CN112778262A (en) | 2021-05-11 |
| CN112778262B true CN112778262B (en) | 2023-03-21 |
Family
ID=75756412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110029779.XA Active CN112778262B (en) | 2021-01-11 | 2021-01-11 | Plant-derived quassin and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112778262B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110818721A (en) * | 2019-11-29 | 2020-02-21 | 广西师范大学 | Lignin compound and preparation method and application thereof |
-
2021
- 2021-01-11 CN CN202110029779.XA patent/CN112778262B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110818721A (en) * | 2019-11-29 | 2020-02-21 | 广西师范大学 | Lignin compound and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 《苦树中苦木素类化学成分的研究》;贺翠等;《中国化学会第十二届全国天然有机化学学术会议论文摘要集》;20180731;第306页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112778262A (en) | 2021-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Matasyoh et al. | Larvicidal activity of metabolites from the endophytic Podospora sp. against the malaria vector Anopheles gambiae | |
| Chanprapai et al. | Antimicrobial activity from Piper sarmentosum Roxb. against rice pathogenic bacteria and fungi | |
| Javaid et al. | Bioassays guided fractionation of Senna occidentalis for identification of natural antifungal constituents against Macrophomina phaseolina | |
| Singh et al. | Activity of neem (Azadirachta indica A. Juss) seed kernel extracts against the mustard aphid, Lipaphis erysimi | |
| Nsangou et al. | Chemical composition and synergistic antimicrobial effects of a vegetatively propagated cameroonian lemon, citrus x limon (l.) osbeck | |
| Jurzysta et al. | Antifungal and hemolytic activity of aerial parts of alfalfa (Medicago) species in relation to saponin composition | |
| Li et al. | Identification of mellein as a pathogenic substance of Botryosphaeria dothidea by UPLC-MS/MS analysis and phytotoxic bioassay | |
| KR100920486B1 (en) | Composition for controlling plant diseases which comprises neolignan compounds or magnolia spp. plant extract containing them, and method for controlling plant diseases using the same | |
| aziz Balah | Chemical and biological characterization of Conyza dioscoridis (L.) desf. family (Compositae) in some perennial weeds control | |
| Jabeen et al. | Management of causal organism of collar rot of bell pepper (Sclerotium rolfsii) by organic solvents extracts of Datura metel fruit | |
| CN112778262B (en) | Plant-derived quassin and preparation method and application thereof | |
| Rajesh et al. | Antifungal metabolite from Muntingia calabura root against early leaf blight of tomato | |
| Rani et al. | Allelopathic effects of Sterculia foetida (L.) against four major weeds | |
| Kaur et al. | Antifungal potential of dill (Anethum graveolens L.) seed essential oil, its extracts and components against phytopathogenic maize fungi | |
| CN114794115B (en) | Application of Penicillium poland extract in preparing herbicide | |
| WO2023019821A1 (en) | Azaphilone polymer compound, and preparation method therefor and use thereof | |
| CN105622686B (en) | Alkaloid compound and preparation method and application thereof | |
| Barrera-Necha et al. | Antifungal activity against postharvest fungi by extracts and compounds of Pithecellobium dulce seeds (huamuchil) | |
| Ma et al. | Phytotoxic phenols from the needles of Cedrus deodara | |
| Akbar et al. | Isolation and characterization of natural herbicidal compound from Drechslera rostrata | |
| KR100760444B1 (en) | Composition for Control AnthracnoseColletotrichum gloeosporioides with extracts and isolated compound from leaves of Anemarrhena asphodeloides | |
| Naik et al. | In vitro evaluation of red rot toxin influence on sugarcane (Saccharum officinarum L.) var. CoC 671 | |
| CN111116535A (en) | Pseudo-osbeckia chinensis flower extract and application thereof | |
| CN113200903B (en) | Pyrrole alkaloid compound with antifeedant and defensive functions on coccinella twenty-eight star in Solanum septemlobum and separation and extraction method thereof | |
| Al-Hashumi et al. | Investigation of some Carboxylic Acids and Phenolic Compounds of Ailanthus altissima Leaves and their its Effect on Italian Cupressus Seedlings Root Rot Fungi |
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 |