CN110903297B - Macroporous resin extraction method of rotenone and analogue - Google Patents
Macroporous resin extraction method of rotenone and analogue Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/20—Fabaceae or Leguminosae [Pea or Legume family], e.g. pea, lentil, soybean, clover, acacia, honey locust, derris or millettia
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Abstract
The invention provides a macroporous resin extraction method of rotenone and analogues, which comprises the following steps: s1, cutting roots and stems of derris elliptica into sections, airing, crushing and sieving to obtain derris elliptica powder; s2, soaking the derris trifoliata powder in an ethanol solution to obtain a leaching solution; s3, concentrating the leaching liquor under reduced pressure to obtain an extract; s4, adding water into the extract, extracting with ethyl acetate, standing, collecting ethyl acetate extract, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure to obtain an ethyl acetate extract; s5, dissolving the ethyl acetate extract with ethanol, slowly adding the obtained solution into the activated macroporous resin, and eluting by using 8-12 column volumes of 25-35 v/v% ethanol solution; then eluting with 45-55 v/v% ethanol solution with 8-12 column volumes; finally collecting 75-85 v/v% ethanol solution eluent, wherein the flow rate of the eluent is 12-18 mL/min; s6, carrying out reduced pressure concentration and vacuum drying to obtain the rotenone. On the premise of environmental protection, the content of rotenone in the extract is high, and the extract meets the high-grade product.
Description
Technical Field
The invention relates to the technical field of rotenone, in particular to a macroporous resin extraction method of rotenone and analogues.
Background
The trefoil Derris (Derris trifoliata) is a common climbing accompanying species of the mangrove forest, the trefoil Derris can cause the death of the mangrove forest if the trefoil Derris covers and spreads seriously through climbing, the trefoil Derris is a 'plant killer' harming the wetland of the mangrove forest, and the control mainly depends on manual removal and other modes to restrain the damage of the trefoil Derris to the mangrove forest. The trefoil derris has strong destructiveness to mangrove forest, so that the mangrove forest protection areas such as Guangxi, Hainan and the like in China are harmed by the plant, and the nations dial a large amount of funds to carry out manual removal. Radix Seu caulis Derridis Trifoliatae contains rotenone and its similar components. Rotenone is a broad-spectrum pesticide, is highly effective to pests and is not easy to generate drug resistance. Rotenone is a contact insecticide with stomach toxicity. Rotenone can directly enter the insect body through skin, stomata and the like, and inhibit the part between coenzyme I and coenzyme Q in the mitochondrial respiratory chain, namely an electron transfer system of the first part of the respiratory chain, so that oxidation-reduction reaction can not be carried out, thereby preventing respiration and causing insect poisoning paralysis. Meanwhile, the rotenone analogue also has a certain insecticidal action. Therefore, the extraction of rotenone and analogues thereof from derris trifoliate is of great significance.
The existing literature reports the extraction method of rotenone, comprising oscillation extraction, microwave extraction and supercritical CO2Extraction and the like; the extraction solvent may be acetone, toluene, benzene, etc. But toluene as a solvent has certain influence on the environment; acetone, chloroform and the like belong to easy-to-detoxify reagents. The use of these agents is not ecological.
Disclosure of Invention
In view of the above, the present invention provides a macroporous resin extraction method for rotenone and the like, which solves the above technical problems.
The technical scheme of the invention is realized as follows: a macroporous resin extraction method of rotenone and analogues comprises the following steps:
s1, cutting roots and stems of derris elliptica into sections, airing, crushing and sieving to obtain derris elliptica powder;
s2, soaking the derris trifoliata powder in an ethanol solution to obtain a leaching solution;
s3, concentrating the leaching liquor under reduced pressure to obtain an extract;
s4, adding water into the extract, extracting with ethyl acetate, standing, collecting ethyl acetate extract, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure to obtain an ethyl acetate extract;
s5, dissolving the ethyl acetate extract with ethanol, slowly adding the obtained solution into the activated macroporous resin, and eluting by using 8-12 column volumes of 25-35 v/v% ethanol solution; then eluting with 45-55 v/v% ethanol solution with 8-12 column volumes; finally, collecting 75-85 v/v% ethanol solution eluent, wherein the flow rate of the eluent is 12-18mL/min, monitoring until the effluent does not have rotenone, monitoring by using a thin-layer chromatography plate, taking a rotenone standard sample as a control, and detecting by using an ultraviolet spectrophotometer until the effluent does not have rotenone;
s6, concentrating the 75-85 v/v% ethanol solution eluent under reduced pressure, and drying in vacuum to obtain rotenone and analogues.
Further, in step S1, the derris trifoliate roots and stems are taken, cut into small segments with the length of 1cm, naturally dried, crushed and sieved by a 40-mesh sieve to obtain the derris trifoliate powder.
Further, in step S2, the ethanol solution is industrial alcohol.
Further, in step S2, the derris trifoliata powder is soaked in the ethanol solution for 2-4 days, and the soaking is repeated for 2-4 times.
Further, in step S3, the reduced pressure concentration temperature is 50 ℃ or lower.
Further, in step S4, the amount of water added is 3-5 times the weight of the extract.
Further, in step S4, the amount of ethyl acetate is 1/3-1/2 of the sum of the weight of the extract and the water.
Further, in step S5, the dosage of the macroporous resin is 0.5-1.5 times of the weight of the radix derris powder,
further, in step S5, 10 column volumes of 30 v/v% ethanol solution are used for elution; then eluting with 10 column volumes of 50 v/v% ethanol solution; finally, 80 v/v% ethanol solution eluent is collected.
In the macroporous resin extraction method of rotenone and the like, in step S5, the flow rate of the eluent is 15 mL/min.
Compared with the prior art, the invention has the beneficial effects that:
(1) the invention provides an effective and environment-friendly extraction method, which selects mangrove killer derris as a raw material, and obtains rotenone and analogues thereof by ethanol extraction, ethyl acetate extraction and macroporous resin separation. On the premise of environmental protection, the content of rotenone in the extract is high, and the extract accords with a superior product (the content of rotenone is more than or equal to 70.0 percent). The extract of the invention can be well applied to disinsection.
(2) The invention avoids using traditional toxic and harmful solvents or solvents which are easy to prepare, is green and environment-friendly; the solvent ethanol and ethyl acetate can be recycled, and the macroporous resin can be repeatedly used after being activated, so that the use of materials is reduced, resources are saved, and the extraction cost is reduced; the invention has simple equipment, avoids using expensive equipment and reduces the preparation cost; and fourthly, the extraction method of the invention has simple operation flow and common eluent, and is suitable for industrial production.
In conclusion, the extraction method disclosed by the invention is environment-friendly, saves resources, is environment-friendly, reduces the cost, simplifies the process, is suitable for industrial production, and provides a good way for effectively utilizing the trefoil derris.
Detailed Description
In order to better understand the technical content of the invention, specific examples are provided below to further illustrate the invention.
The experimental methods used in the examples of the present invention are all conventional methods unless otherwise specified.
The materials, reagents and the like used in the examples of the present invention can be obtained commercially without specific description.
Example 1
A macroporous resin extraction method of rotenone and analogues comprises the following steps:
s1, collecting the roots and stems of the derris trifoliata which is discarded after mangrove weed control, cutting into small sections with the length of 1cm, naturally airing, crushing by an industrial crusher, and sieving by a 40-mesh sieve to obtain derris trifoliata powder;
s2, soaking 1Kg of derris trifoliata powder in industrial alcohol, wherein the industrial alcohol is preferably used for submerging the derris trifoliata powder, and filtering after 3 days; soaking the residue in industrial alcohol, repeating the process for 3 times, and mixing the filtrates to obtain extractive solution;
s3, concentrating the leaching solution under reduced pressure at a temperature below 50 ℃ to obtain an extract, and recovering ethanol;
s4, adding tap water with the weight 3 times that of the extract, extracting with ethyl acetate, wherein the amount of ethyl acetate is 1/3 of the sum of the weight of the extract and the weight of water, standing, collecting ethyl acetate extract, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure to obtain an ethyl acetate extract;
s5, dissolving the ethyl acetate extract with ethanol, slowly adding the obtained solution into activated macroporous resin, wherein the dosage of the macroporous resin is 0.5 times of the weight of the derris trifoliata powder, and eluting with 10 column volumes of 30 v/v% ethanol solution; followed by elution with 10 column volumes of 50 v/v% ethanol solution; collecting 80 v/v% ethanol solution eluate, monitoring with thin layer chromatography plate, using rotenone standard sample as control, and detecting with ultraviolet spectrophotometer until the effluent has no rotenone; the flow rate of the eluate was 15 mL/min.
S6, concentrating the collected ethanol eluent under reduced pressure, and vacuum drying to obtain the extract, i.e. rotenone and the like.
Example 2
A macroporous resin extraction method of rotenone and analogues comprises the following steps:
s1, collecting the roots and stems of the derris trifoliata which is discarded after mangrove weed control, cutting into small sections with the length of 1cm, naturally airing, crushing by an industrial crusher, and sieving by a 40-mesh sieve to obtain derris trifoliata powder;
s2, soaking 5Kg of derris trifoliate powder in industrial alcohol, wherein the industrial alcohol is preferably used for submerging the derris trifoliate powder, and filtering after 3 days; soaking the residue in industrial alcohol, repeating the process for 3 times, and mixing the filtrates to obtain extractive solution;
s3, concentrating the leaching solution under reduced pressure at a temperature below 50 ℃ to obtain an extract, and recovering ethanol;
s4, adding tap water with the weight being 4 times that of the extract, extracting with ethyl acetate, wherein the amount of ethyl acetate is 1/2 of the sum of the weight of the extract and the weight of water, standing, collecting ethyl acetate extract, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure to obtain an ethyl acetate extract;
s5, dissolving the ethyl acetate extract with ethanol, slowly adding the obtained solution into activated macroporous resin, wherein the dosage of the macroporous resin is 0.5 times of the weight of the derris trifoliata powder, and eluting with 10 column volumes of 30 v/v% ethanol solution; followed by elution with 10 column volumes of 50 v/v% ethanol solution; collecting 80 v/v% ethanol solution eluate, monitoring with thin layer chromatography plate, using rotenone standard sample as control, and detecting with ultraviolet spectrophotometer until the effluent has no rotenone; the flow rate of the eluate was 15 mL/min.
S6, concentrating the collected ethanol eluent under reduced pressure, and vacuum drying to obtain the extract, i.e. rotenone and the like.
Example 3
A macroporous resin extraction method of rotenone and analogues comprises the following steps:
s1, collecting the roots and stems of the derris trifoliata which is discarded after mangrove weed control, cutting into small sections with the length of 1cm, naturally airing, crushing by an industrial crusher, and sieving by a 40-mesh sieve to obtain derris trifoliata powder;
s2, soaking 10Kg of derris trifoliate powder in industrial alcohol, wherein the industrial alcohol is preferably used for submerging the derris trifoliate powder, and filtering after 3 days; soaking the residue in industrial alcohol, repeating the process for 3 times, and mixing the filtrates to obtain extractive solution;
s3, concentrating the leaching solution under reduced pressure at a temperature below 50 ℃, and recovering ethanol;
s4, adding tap water with the weight 5 times that of the extract, extracting with ethyl acetate, wherein the amount of ethyl acetate is 1/3 of the sum of the weight of the extract and the weight of water, standing, collecting ethyl acetate extract, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure to obtain an ethyl acetate extract.
S5, dissolving the ethyl acetate extract with ethanol, slowly adding the obtained solution into activated macroporous resin, wherein the dosage of the macroporous resin is 0.5 times of the weight of the derris trifoliata powder, and eluting with 10 column volumes of 30 v/v% ethanol solution; followed by elution with 10 column volumes of 50 v/v% ethanol solution; collecting 80 v/v% ethanol solution eluate, monitoring with thin layer chromatography plate, using rotenone standard sample as control, and detecting with ultraviolet spectrophotometer until the effluent has no rotenone; the flow rate of the eluent is 15 mL/min;
s6, concentrating the collected ethanol eluent under reduced pressure, and vacuum drying to obtain the extract, i.e. rotenone and the like.
Example 4
A macroporous resin extraction method of rotenone and analogues comprises the following steps:
s1, collecting the roots and stems of the derris trifoliata which is discarded after mangrove weed control, cutting into small sections with the length of 1cm, naturally airing, crushing by an industrial crusher, and sieving by a 40-mesh sieve to obtain derris trifoliata powder;
s2, soaking 20Kg of derris trifoliate powder in industrial alcohol, wherein the industrial alcohol is preferably used for submerging the derris trifoliate powder, and filtering after 3 days; soaking the residue in industrial alcohol, repeating the process for 2 times, and mixing the filtrates to obtain extractive solution;
s3, concentrating the leaching solution under reduced pressure at a temperature below 50 ℃ to obtain an extract, and recovering ethanol;
s4, adding tap water with the weight being 4 times that of the extract, extracting with ethyl acetate, wherein the amount of ethyl acetate is 1/3 of the sum of the weight of the extract and the weight of water, standing, collecting ethyl acetate extract, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure to obtain an ethyl acetate extract;
s5, dissolving the ethyl acetate extract with ethanol, slowly adding the obtained solution into activated macroporous resin, wherein the dosage of the macroporous resin is 0.5 times of the weight of the derris trifoliata powder, and eluting with 10 column volumes of 30 v/v% ethanol solution; followed by elution with 10 column volumes of 50 v/v% ethanol solution; collecting 80 v/v% ethanol solution eluate, monitoring with thin layer chromatography plate, using rotenone standard sample as control, and detecting with ultraviolet spectrophotometer until the effluent has no rotenone; the flow rate of the eluent is 15 mL/min;
s6, concentrating the collected ethanol eluent under reduced pressure, and vacuum drying to obtain the extract, i.e. rotenone and the like.
Example 5
This embodiment is different from embodiment 1 in that,
in step S2, the derris trifoliata powder is soaked in the ethanol solution for 2 days, and the soaking is repeated 4 times.
In step S5, the dosage of the macroporous resin is 1 time of the weight of the radix derris powder; eluting with 10 column volumes of 25 v/v% ethanol solution; then eluting with 10 column volumes of 45 v/v% ethanol solution; finally collecting 75 v/v% ethanol solution eluent; the flow rate of the eluate was 12 mL/min.
Example 6
This embodiment is different from embodiment 1 in that,
in step S2, the derris trifoliata powder is soaked in the ethanol solution for 4 days, and the soaking is repeated 2 times.
In step S5, the dosage of the macroporous resin is 1.5 times of the weight of the radix derris powder; eluting with 10 column volumes of 35 v/v% ethanol solution; then eluting with 10 column volumes of 55 v/v% ethanol solution; finally collecting 85 v/v% ethanol solution eluent; the flow rate of the eluate was 18 mL/min.
Comparative example 1
This comparative example differs from example 1 in that, in step S5, first, 5 column volumes of 45 v/v% ethanol solution were used for elution; then eluting with 15 column volumes of 60 v/v% ethanol solution; finally, 90 v/v% ethanol solution eluent is collected.
Weighing the final extracts prepared in examples 1-6 and comparative example 1, and detecting the rotenone content, wherein the conditions for detecting the rotenone content are as follows: the assay was carried out by High Performance Liquid Chromatography (HPLC) using a rotenone standard sample (Sigma, content 99%) as a reference, Agilent 6890N, USA. Detection conditions are as follows: c18 chromatographic column, 250mm × 4.0mm stainless steel column, mobile phase v (acetonitrile): v (water): 60: 40, column temperature: 30 ℃, flow rate of 1.0mL/min, detection wavelength of 294nm, sample amount: 10 μ L. The retention time of rotenone was 12.053.
The yield of the extracts and the rotenone content of each example and comparative example are as follows:
the above results show that the extract of examples 1-6 of the present invention has a high rotenone content, which is in line with the superior product (rotenone content ≥ 70.0%). The extract of the invention can be well applied to disinsection.
In addition, it was confirmed that the extracts of examples 1 to 6 of the present invention contained rotenone analogs.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A macroporous resin extraction method of a rotenone extract is characterized by comprising the following steps:
s1, cutting roots and stems of derris elliptica into sections, airing, crushing and sieving to obtain derris elliptica powder;
s2, soaking the derris trifoliata powder in an ethanol solution to obtain a leaching solution;
s3, concentrating the leaching liquor under reduced pressure to obtain an extract;
s4, adding water into the extract, extracting with ethyl acetate, standing, collecting ethyl acetate extract, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure to obtain an ethyl acetate extract;
s5, dissolving the ethyl acetate extract with ethanol, slowly adding the obtained solution into the activated macroporous resin, and eluting by using 8-12 column volumes of 25-35 v/v% ethanol solution; then eluting with 45-55 v/v% ethanol solution with 8-12 column volumes; finally collecting 75-85 v/v% ethanol solution eluent, wherein the flow rate of the eluent is 12-18mL/min, and monitoring until the effluent does not generate rotenone;
s6, concentrating the finally collected ethanol eluent under reduced pressure, and drying in vacuum to obtain the rotenone extract.
2. The method for extracting rotenone extract with macroporous resin as claimed in claim 1, wherein in step S1, radix Seu caulis Derridis Trifoliatae and stem are cut into small segments of 1cm length, air dried, pulverized, and sieved with 40 mesh sieve to obtain radix Seu caulis Derridis Trifoliatae powder.
3. The method for extracting rotenone from macroporous resin as claimed in claim 1, wherein the ethanol solution is industrial alcohol in step S2.
4. The method for extracting rotenone extract with macroporous resin as claimed in claim 1, wherein in step S2, radix derris trifoliate powder is soaked in ethanol solution for 2-4 days, and the soaking is repeated for 2-4 times.
5. The method for extracting rotenone from macroporous resin as claimed in claim 1, wherein the concentration under reduced pressure is below 50 ℃ in step S3.
6. The method for extracting rotenone extract with macroporous resin as claimed in claim 1, wherein in step S4, water is added in an amount of 3-5 times the weight of the extract.
7. The method for extracting rotenone extract with macroporous resin as claimed in claim 1, wherein in step S4, the amount of ethyl acetate is 1/3-1/2 of the total weight of extract and water.
8. The method for extracting rotenone extract with macroporous resin as claimed in claim 1 or 7, wherein the amount of macroporous resin is 0.5-1.5 times of the weight of radix Seu caulis Parthenocissi Tricuspidatae powder in step S5.
9. The method for extracting rotenone from macroporous resin as claimed in claim 1, wherein in step S5, 10 column volumes of 30 v/v% ethanol solution are used for elution; then eluting with 10 column volumes of 50 v/v% ethanol solution; finally, 80 v/v% ethanol solution eluent is collected.
10. The method for extracting rotenone from macroporous resin as claimed in claim 1, wherein the flow rate of the eluent in step S5 is 15 mL/min.
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