CN108531526B - Folium artemisiae argyi extract and preparation method and application thereof - Google Patents

Folium artemisiae argyi extract and preparation method and application thereof Download PDF

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CN108531526B
CN108531526B CN201810461118.2A CN201810461118A CN108531526B CN 108531526 B CN108531526 B CN 108531526B CN 201810461118 A CN201810461118 A CN 201810461118A CN 108531526 B CN108531526 B CN 108531526B
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folium artemisiae
artemisiae argyi
extract
argyi extract
concentrating
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CN108531526A (en
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周培
束影
蒋泽慧
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HUBEI AIAITIE HEALTH TECHNOLOGY CO.,LTD.
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Yangzhou Polytechnic Institute
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
    • C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
    • C12P19/626—Natamycin; Pimaricin; Tennecetin
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms

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  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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Abstract

The invention relates to a folium artemisiae argyi extract and a preparation method and application thereof, wherein the preparation method of the folium artemisiae argyi extract comprises the following steps: (1) pulverizing dried folium Artemisiae Argyi, sterilizing, placing in sterile fermentation tank, adding glucose and yeast powder, mixing, sealing the fermentation tank, and naturally fermenting at 20-25 deg.C for 20-25 days to obtain fermented product; (2) soaking the fermented product obtained in the step (1) in acetone, filtering, concentrating the filtrate, adsorbing by macroporous resin, eluting with 60-70% ethanol solution by volume fraction, collecting eluate with 5-6 times column volume, decolorizing with active carbon, concentrating, and drying to obtain folium Artemisiae Argyi extract.

Description

Folium artemisiae argyi extract and preparation method and application thereof
Technical Field
The invention belongs to the field of extraction, and particularly relates to a folium artemisiae argyi extract and a preparation method and application thereof.
Background
The folium artemisiae argyi is a dry leaf of Artemisia argyi (Artemisia argyi levl. etvant.) belonging to Artemisia of the Compositae, and more than 100 compounds are separated from the folium artemisiae argyi at present and comprise chemical components such as terpenes, flavones, phenylpropanoids, aromatic acids (aldehydes), steroids and fatty acids. Exhibit a wide range of biological activities such as analgesia, anti-inflammatory, anti-coagulation, anti-tumor, etc.; the folium Artemisiae Argyi volatile oil also has certain mite removing effect. However, there have been no reports of the killing of agricultural pests (e.g. aphids, armyworms) by artemisia argyi extracts or active compounds. The invention provides an application of folium artemisiae argyi fermentation extract and active ingredients thereof in the aspect of preventing and controlling agricultural pests.
Disclosure of Invention
The invention provides a folium artemisiae argyi extract which is characterized in that a preparation method of the folium artemisiae argyi extract comprises the following steps:
(1) pulverizing dried folium Artemisiae Argyi, sterilizing, placing in sterile fermentation tank, adding glucose and yeast powder, mixing, sealing the fermentation tank, and naturally fermenting at 20-25 deg.C for 20-25 days to obtain fermented product;
(2) soaking the fermented product obtained in the step (1) in acetone, filtering, concentrating the filtrate, adsorbing by macroporous resin, eluting with 60-70% ethanol solution by volume fraction, collecting eluate with 5-6 times column volume, decolorizing with active carbon, concentrating, and drying to obtain folium Artemisiae Argyi extract.
In the step (1), the dosage of the glucose is 10-15% of the mass of the folium artemisiae argyi, and the dosage of the yeast powder is 3-5% of the mass of the folium artemisiae argyi;
in the step (2), the dosage of acetone is 8-10L per kg of folium artemisiae argyi; the acetone soaking time is preferably 20-24 hours; the model of the macroporous resin is selected from one of AB-8 and D101.
Another embodiment of the present invention provides a method for preparing the above artemisia leaf extract, which is characterized by comprising the steps of:
(1) pulverizing dried folium Artemisiae Argyi, sterilizing, placing in sterile fermentation tank, adding glucose and yeast powder, mixing, sealing the fermentation tank, and naturally fermenting at 20-25 deg.C for 20-25 days to obtain fermented product;
(2) soaking the fermented product obtained in the step (1) in acetone, filtering, concentrating the filtrate, adsorbing by macroporous resin, eluting with 60-70% ethanol solution by volume fraction, collecting eluate with 5-6 times column volume, decolorizing with active carbon, concentrating, and drying to obtain folium Artemisiae Argyi extract.
In the step (1), the dosage of the glucose is 10-15% of the mass of the folium artemisiae argyi, and the dosage of the yeast powder is 3-5% of the mass of the folium artemisiae argyi;
in the step (2), the dosage of acetone is 8-10L per kg of folium artemisiae argyi; the acetone soaking time is preferably 20-24 hours; the model of the macroporous resin is selected from one of AB-8 and D101.
Another embodiment of the invention provides an application of the folium artemisiae argyi extract in controlling agricultural pests. The agricultural pests are preferably aphids and armyworms.
Another embodiment of the present invention provides an application of the above folium artemisiae argyi extract in preparing an insecticide. The pesticide preferably kills aphids and armyworms.
Another embodiment of the present invention provides an insecticide, characterized in that the insecticide comprises the above artemisia argyi extract as an active ingredient. The pesticide preferably kills aphids and armyworms.
Another embodiment of the present invention provides a compound of formula I or a salt thereof, characterized in that the formula I has the structure:
Figure BDA0001659653830000021
another embodiment of the present invention provides a method for preparing a compound having the structure of formula I above, characterized by the steps of:
subjecting the folium Artemisiae Argyi extract to normal phase silica gel column chromatography to obtain compound with structure of formula I.
The normal phase silica gel column chromatography is carried out, the mesh number of the silica gel is preferably 200-300 meshes, and the eluent is preferably an ethyl acetate/petroleum ether mixed solvent with the volume ratio of 1: 10-12.
The preparation method of the folium artemisiae argyi extract comprises the following steps:
(1) pulverizing dried folium Artemisiae Argyi, sterilizing, placing in sterile fermentation tank, adding glucose and yeast powder, mixing, sealing the fermentation tank, and naturally fermenting at 20-25 deg.C for 20-25 days to obtain fermented product;
(2) soaking the fermented product obtained in the step (1) in acetone, filtering, concentrating the filtrate, adsorbing by macroporous resin, eluting with 60-70% ethanol solution by volume fraction, collecting eluate with 5-6 times column volume, decolorizing with active carbon, concentrating, and drying to obtain folium Artemisiae Argyi extract.
In the step (1), the dosage of the glucose is 10-15% of the mass of the folium artemisiae argyi, and the dosage of the yeast powder is 3-5% of the mass of the folium artemisiae argyi;
in the step (2), the dosage of acetone is 8-10L per kg of folium artemisiae argyi; the acetone soaking time is preferably 20-24 hours; the model of the macroporous resin is selected from one of AB-8 and D101.
Another embodiment of the present invention provides the use of a compound of the structure of formula I or a salt thereof as described above for controlling an agricultural pest. The agricultural pests are preferably aphids and armyworms.
In another embodiment of the invention, there is provided the use of a compound of the structure of formula I, or a salt thereof, as described above, in the preparation of a pesticide. The pesticide preferably kills aphids and armyworms.
Another embodiment of the present invention provides a pesticide characterized in that the pesticide has a compound of the structure of formula I or a salt thereof as an active ingredient. The pesticide preferably kills aphids and armyworms.
Detailed Description
In order to facilitate a further understanding of the invention, the following examples are provided to illustrate it in more detail. However, these examples are only for better understanding of the present invention and are not intended to limit the scope or the principle of the present invention, and the embodiments of the present invention are not limited to the following.
Example 1
(1) Pulverizing dried folium Artemisiae Argyi (1.0kg), sterilizing, placing in sterile fermentation tank, adding glucose (100g) and yeast powder (30g), mixing, sealing the fermentation tank, and naturally fermenting at 20-25 deg.C for 20 days to obtain fermented product;
(2) soaking the fermented product obtained in the step (1) in acetone (8L) for 24 hours, filtering, concentrating the filtrate, adsorbing by AB-8 type macroporous resin, eluting by using 60% ethanol solution, collecting eluent with 6 times of column volume, decoloring by using active carbon, concentrating and drying to obtain the folium artemisiae argyi extract (hereinafter referred to as a product A).
Example 2
(1) Pulverizing dried folium Artemisiae Argyi (1.0kg), sterilizing, placing in sterile fermentation tank, adding glucose (150g) and yeast powder (50g), mixing, sealing the fermentation tank, and naturally fermenting at 20-25 deg.C for 25 days to obtain fermented product;
(2) soaking the fermented product obtained in the step (1) in acetone (10L) for 20 hours, filtering, concentrating the filtrate, adsorbing by using D101 type macroporous resin, eluting by using an ethanol solution with the volume fraction of 70%, collecting eluent with the volume of 5 times of the column volume, decoloring by using active carbon, concentrating and drying to obtain the folium artemisiae argyi extract (hereinafter referred to as a product B).
Example 3
(1) Pulverizing dried folium Artemisiae Argyi (1.0kg), soaking in acetone (8L) for 24 hr, filtering, concentrating the filtrate, adsorbing with AB-8 type macroporous resin, eluting with 60% ethanol solution, collecting eluate 6 times of column volume, decolorizing with active carbon, concentrating, and drying to obtain product C (no compound of formula I detected by TLC).
Example 4
And (3) carrying out normal-phase silica gel column chromatography on the product A (1.0g), wherein the mesh number of the silica gel is 200-300 meshes, and the eluent is ethyl acetate/petroleum ether which is 1/10-1/12, so that the compound (382mg) with the structure shown in the formula I is obtained, and the HPLC purity is 98.0%.
MS, one-dimensional, two-dimensional NMR data gives formula I having the following structure:
Figure BDA0001659653830000041
ESIMS and ESIMS of formula I only1H,13C NMR data. Structure confirmation data: ESIMS M/z 154.09[ M + H ]]+；1H,13The C NMR data are shown in the following table.
TABLE 11H,13C NMR data (CDCl)3，600/150MHz)
Figure BDA0001659653830000042
Example 5
Subjecting product B (1.0g) to normal phase silica gel column chromatography with mesh number of 200-300, and eluting with ethyl acetate/petroleum ether 1/10-1/12 to obtain compound (398mg) with HPLC purity of 97.5%,1H,13the C NMR data agree with those of example 4.
Example 6
The insecticidal activity of the compounds of formula I, product a, product B, product C of the present invention against aphids and armyworms at a concentration of 300 μ g/mL was tested according to the test method for insecticidal activity against aphids and armyworms described in example 14 of chinese patent application publication No. CN101875653A, and the results are shown in the following table.
Test article Aphid (mortality%) Armyworm (mortality%)
A compound of formula I 100 100
Product A 52 61
Product B 56 62
Product C 0 8

Claims (7)

1. The folium artemisiae argyi extract is characterized in that the preparation method of the folium artemisiae argyi extract comprises the following steps:
(1) pulverizing dried folium Artemisiae Argyi, sterilizing, placing in sterile fermentation tank, adding glucose and yeast powder, mixing, sealing the fermentation tank, and naturally fermenting at 20-25 deg.C for 20-25 days to obtain fermented product;
(2) soaking the fermented product obtained in the step (1) in acetone, filtering, concentrating the filtrate, adsorbing by macroporous resin, eluting with 60-70% ethanol solution by volume fraction, collecting eluate with 5-6 times column volume, decolorizing with active carbon, concentrating, and drying to obtain folium Artemisiae Argyi extract.
2. The folium artemisiae argyi extract of claim 1, wherein the amount of the glucose in the step (1) is 10% -15% of the mass of the folium artemisiae argyi, and the amount of the yeast powder is 3% -5% of the mass of the folium artemisiae argyi.
3. The mugwort extract according to any one of claims 1-2, wherein the amount of acetone used in step (2) is 8-10L per kg of mugwort; the acetone soaking time is 20-24 hours; the model of the macroporous resin is selected from one of AB-8 and D101.
4. Use of the artemisia argyi extract as claimed in any one of claims 1 to 3 for controlling agricultural pests.
5. Use according to claim 4, characterized in that said agricultural pests are selected from aphids, armyworms.
6. Use of the artemisia leaf extract as claimed in any one of claims 1 to 3 for preparing an insecticide.
7. An insecticide, characterized in that the insecticide comprises the mugwort leaf extract according to any one of claims 1 to 3 as an active ingredient.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102727550A (en) * 2012-07-10 2012-10-17 河北联合大学 Antifungal artemisia argyi rhizome leavening and preparation technology thereof
CN104152514A (en) * 2014-07-24 2014-11-19 北京翰若生物科技有限公司 Origin fermentation method and origin fermentation product prepared by same
KR20160079269A (en) * 2014-12-26 2016-07-06 가톨릭대학교 산학협력단 Anti-inflammatory pharmaceutical composition and health functional food containing artemisia fermentation extract
CN108690047A (en) * 2018-05-14 2018-10-23 扬州工业职业技术学院 A kind of heterocyclic compound and its application as insecticide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102727550A (en) * 2012-07-10 2012-10-17 河北联合大学 Antifungal artemisia argyi rhizome leavening and preparation technology thereof
CN104152514A (en) * 2014-07-24 2014-11-19 北京翰若生物科技有限公司 Origin fermentation method and origin fermentation product prepared by same
KR20160079269A (en) * 2014-12-26 2016-07-06 가톨릭대학교 산학협력단 Anti-inflammatory pharmaceutical composition and health functional food containing artemisia fermentation extract
CN108690047A (en) * 2018-05-14 2018-10-23 扬州工业职业技术学院 A kind of heterocyclic compound and its application as insecticide

Non-Patent Citations (4)

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Title
"Bioactivity of Essential Oil of Artemisia argyi Lévl. et Van. and Its Main Compounds Against Lasioderma serricorne";Wen-Juan Zhang 等;《Journal of Oleo Science》;20140729;第63卷(第8期);第829-837页 *
"艾叶水提物及其发酵物体内外抗阴道毛滴虫作用";白静 等;《中成药》;20141031;第36卷(第10期);第2040-2044页 *
"艾叶的化学成分及药理作用研究进展";李真真 等;《国际药学研究杂志》;20161231;第43卷(第6期);第1059-1066页 *
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