CN111116535A - Pseudo-osbeckia chinensis flower extract and application thereof - Google Patents

Pseudo-osbeckia chinensis flower extract and application thereof Download PDF

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CN111116535A
CN111116535A CN202010011030.8A CN202010011030A CN111116535A CN 111116535 A CN111116535 A CN 111116535A CN 202010011030 A CN202010011030 A CN 202010011030A CN 111116535 A CN111116535 A CN 111116535A
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pseudo
osbeckia
extract
petroleum ether
compound
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陈文豪
杨健妮
惠阳
周秀悄
黄丹
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Hainan Normal University
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Hainan Normal University
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    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
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Abstract

The invention discloses a pseudo-osbeckia flower extract and application thereof, which is prepared by extracting dry powder of pseudo-osbeckia flower with petroleum ether solvent; filtering the extractive solution, concentrating under reduced pressure to obtain petroleum ether dissolved fraction, and separating the petroleum ether fraction to obtain 5 flavonoids, 2 sterols, 1 benzoic acid, 1 sesquiterpene, 1 alkaloid, 1 pyrone and 3 chromene compounds. The extract prepared by the invention has high yield, simple process flow and low cost, is suitable for large-scale preparation, has good insect-resistant activity and can be applied to auxiliary plant insecticides.

Description

Pseudo-osbeckia chinensis flower extract and application thereof
Technical Field
The invention belongs to the technical field of extraction and separation of active ingredients of natural plants, and particularly relates to a preparation method of a pseudo-osmia-bedstraw flower extract and insect-resistant application thereof.
Background
Pseudorue odorata (Praxelis clematidea (Griseb.) r.m.king & h.rob.) also known as "catfish" is an annual herb of the genus pseudorue (Praxelis C) of the family Compositae (Compositae), and Eupatorium Veldkamp (Eupatorium L) of the genus Eupatorium is its name, native south america. In China, the pseudo-osmyl grass was first discovered in hong Kong in the 80 th of the 20 th century, and is now widely distributed on the roadside, wasteland, farmland, grassland and the like in coastal areas such as Guangdong, Fujian, hong Kong, Macau, Taiwan, Hainan and the like, and generally grows in low mountains, hills, plains and the like. The osmyl grass has strong absorption capacity to soil nutrients, is easy to consume soil fertility, has serious tillering damage to soil, can secrete a toxic and malodorous substance to influence foraging of livestock, thus forming a great threat to the survival of biological species in invasive regions, causing serious loss to the development of local socioeconomic development, becoming one of the most serious malignant weeds in south China, and being a third batch of exotic invasive species in the Chinese invasive species list issued by the ministry of environmental protection.
The current research on the biological activity of the pseudo-rue is mainly focused on the aspects of chemosensitization and insecticidal action. The root exudates of the pseudo-osbeckia chinensis are reported to have allelopathy on 6 receptor plants such as the aircraft grass, the ageratum conyzoides and the eleusine indica in the preliminary research of the allelophora pseudoosbeckia chinensis root exudates allelopathy substance, the academic report of tropical crops, 2010, 31(7): 1200-. Guodawei et al report in Zhejiang agriculture 2014 (26 (5):1278-1283 that the pseudo-odorous grass essential oil has certain poisoning and antifeedant effects on diamondback moth larvae. Guxin et al reported in the report of "the antibacterial activity of methanol extracts of pseudo-osbeckia and Murraya paniculata on rubber tree powdery mildew", the report of the Laurera victoria, 2012, 33(6): 1089-. Plum water and the like reported in Jiangsu agricultural science 2015, 43(1): 136-; the stomach toxicity activity and the food refusal activity of the acetone extract are the strongest, and 45.27 percent and 46.67 percent are respectively reached after 48 hours and 72 hours of treatment. The research on the chemical components of the pseudo-osmyl grass is less, and Deng Shiming et al report in northwest plant bulletin, 2009, 29(12):2548-2550 "and" research on the chemical components of the pseudo-osmyl grass of the foreign invasive plant, grass science, 2011, 28(10):1882-1887 ", that 10 flavonoids such as 5,6,7, 4' -tetramethoxyflavone, 7-hydroxy-5, 6, 4' -trimethoxyflavone and 4' -hydroxy-5, 6, 7-trimethoxyflavone, 3 steroids, 1 triterpene and 1 organic acid are separated from the aboveground part of the pseudo-osmyl grass, and do not see further biological activity research on monomer compounds. Glda Maia et al reported in "Flavonoids from Praxellis clematidis R.M.King and Robinson modulated bacterial drug delivery. molecules, 2011, 16(6): 4828-4835" isolated from P.pseudotinus six Flavonoids: apigenin, genkwanine, 7,4' -dimethyllapigenin, trimethypapigenin, cirsimilein and tetramethyl-scutellein, all of which exhibit weak inhibitory activity against staphylococcus aureus.
In terms of the biological activity of the extract, Chinese patents with publication numbers CN108850012A and CN106577793A respectively disclose that the stem and leaf extract of the pseudorue is combined with other extracts to be used for killing pests such as dichocrocis punctiferalis, aphids, bean turnips and the like and preventing and treating weeds such as crab grass, abutilon, polygonum hydropiper, chenopodium album, horseweed herb, mud and common fenugreek herb, infantile ao, alopecurus aethiopica and the like; chinese patents with publication numbers CN106220456A and CN108496994A respectively disclose that the volatile oil of the rue is combined with other raw materials to kill the citrus psyllid and prevent and control the gummosis of the Shatian pomelo; chinese patent publication No. CN110169422A discloses that the aqueous extract of stem and leaf of pseudo-rue blumea, the essential oil of pseudo-rue blumea and other extracts are used in combination for killing bacterial wilt, citrus sandworm pathogenic bacteria and huanglongbing pathogenic bacteria.
So far, no patents related to the pseudo-bed bugs are found in the aspect of insect-resistant application, and no report is provided about the separation of the anti-mealworm effective parts of the pseudo-bed bugs and further chemical components of the anti-mealworm effective parts.
Disclosure of Invention
The invention aims to provide a preparation method of a pseudo-osmia herb flower extract, which utilizes a simple extraction and separation method to screen the insect-resistant activity of a pseudo-osmia herb flower petroleum ether dissolved part, finds an active part, and clarifies the chemical components of the active part through multiple column chromatography.
In order to achieve the purpose, the technical scheme of the invention is as follows: provides a pseudo-osbeckia extract, which comprises the following extraction steps:
(1) adding petroleum ether solvent into the dried powder of the pseudo-osbeckia flowers for extraction to obtain pseudo-osbeckia flowers extract;
(2) filtering and concentrating the extract of the pseudo-osbeckia chinensis bunge under reduced pressure to obtain a petroleum ether dissolved extract;
(3) the petroleum ether dissolved extract is subjected to repeated column chromatography to obtain 5 flavonoids compounds, 2 sterol compounds, 1 benzoic acid compound, 1 sesquiterpene compound, 1 alkaloid compound, 1 pyrone compound and 3 chromene compounds.
Preferably, the dried powder of the pseudo-osbeckia flower is obtained by drying the pseudo-osbeckia flower in the shade and then crushing.
Preferably, the petroleum ether solvent extraction method comprises room temperature soaking, heating or ultrasonic extraction.
Preferably, the temperature of the petroleum ether is 60-90 ℃.
Preferably, the volume ratio of the dried powder of the pseudo-osbeckia chinensis to the petroleum ether solvent is 1: 1-1: 10.
preferably, the filler for column chromatography is silica gel or sephadex for column chromatography.
Preferably, 5 flavonoids are characterized by 5,6,4 '-trimethoxy flavone, 6,7,8, 4' -tetramethoxy flavone, 5,6,7,3 ', 4', 5 '-hexamethoxy flavone, 5,6,7,8, 3', 4', 5' -heptamethoxy flavone, 2 '-hydroxy-4, 4', 5 ', 6' -tetramethoxy chalcone, 2 sterol compounds are characterized by β -sitosterol and stigmasterol, 1 benzoic acid compound is characterized by p-methoxybenzoic acid, 1 sesquiterpene compound is characterized by 10 α -hydroxy-4-ene-15-aldehyde, 1 alkaloid compound is characterized by (2S,3S,4R,10E) -2- [ (2R) -2-hydroxytetratetradecanoylamino ] 10-octadecene-1, 3, 4-triol, 1 pyrone compound is characterized by- [ [ 6- (2S) -2-hydroxy-1-methyl propyl ] -4-methoxy-5-methyl-chromene-1, 3, 4-dimethyl-2- (2S) -2-ethoxy) -2-dimethyl-2-ethyl-chromene, 7-2-dimethyl-2-ethyl-2-methoxy-7-2-dimethyl-2-ethyl-2-chromene, 7-2-dimethyl-2-ethyl-2-methoxy-2-one.
The invention also aims to provide the application of the medicinal composition prepared from the pseudo-osbeckia herb extract and medicinal excipients or auxiliary materials in the plant pesticide; in particular to the application of the anti-insect and insecticidal activity of the medicinal composition prepared by the pseudobedbuge extract and medicinal excipient or auxiliary material in the contact killing and antifeedant action of yellow mealworm larvae.
The pseudo-osbeckia chinensis extract has the following beneficial effects:
(1) the method comprises the steps of screening the dissolved part of the osbeckia chinensis petroleum ether by using a simple extraction and separation method to obtain an active part, and clarifying chemical components of the active part through multiple column chromatography.
(2) The chemical components of the extract obtained by the invention are clear.
(3) The obtained extract has good insect-resisting activity, and can be widely used in plant pesticide.
(4) The extract prepared by the invention has high yield, simple process flow and low cost, and is suitable for large-scale preparation.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out under conventional conditions or conditions recommended by the manufacturers.
The preparation method of the pseudo-osbeckia flower extract comprises the following steps:
(1) drying and crushing the false osmyl grass flower medicinal material in the shade (sieving with a 20-80 mesh sieve), adding a petroleum ether (60-90 ℃) solvent for extraction, and adopting room-temperature soaking, heating or ultrasonic extraction for 60 minutes to 7 days, wherein the material-liquid ratio is 1: 1-1: 10;
(2) filtering the extractive solution of the medicinal material of the rue-kola herb, and concentrating under reduced pressure to obtain petroleum ether dissolved extract;
(3) subjecting the petroleum ether dissolved part to silica gel column chromatography, eluting with pure petroleum ether as solvent to remove long chain oil wax and other components, eluting with ethyl acetate, concentrating the eluate under vacuum to obtain petroleum ether part with broad insect resistance, subjecting the petroleum ether part to repeated column chromatography, and selecting normal phase silica gel or Sephadex LH-20 as filler for stationary phase:
petroleum ether: ethyl acetate (15: 1), petroleum ether: ethyl acetate (20: 1) silica gel column chromatography to obtain compounds (2), (5) and (13), respectively; petroleum ether: ethyl acetate (10: 1), petroleum ether: ethyl acetate (15: 1) silica gel column chromatography followed by Sephadex LH-20 column chromatography (chloroform: methanol ═ 1: 1, v/v) and petroleum ether: separating by ethyl acetate (7: 1) silica gel column chromatography to obtain compounds (1), (9), (3), (4) and (12); petroleum ether: ethyl acetate (5: 1), chloroform: ethyl acetate (30: 1), petroleum ether: ethyl acetate (5: 1) was subjected to silica gel column chromatography to give (6), (7), (8), (10), (11) and (14).
(4) The purified monomeric compounds are structurally identified by combining various spectral spectrum techniques (including IR, UV, MS, 1D/2D NMR) and related literature references, and the structures of 5 flavonoids, 2 sterols, 1 benzoate, 1 sesquiterpene compound, 1 alkaloid compound, 1 pyrone compound and 3 chromene compounds are 5,6,4 '-trimethoxyflavone (1), 6,7,8, 4' -tetramethoxyflavone (2), 5,6,7,3 ', 4', 5 '-hexamethoxyflavone (3), 5,6,7,8, 3', 4', 5' -heptamethoxyflavone (4), 2 '-hydroxy-4, 4', 5 ', 6' -tetramethoxychalcone (5), β -sitosterol (6), stigmasterol (7), p-methoxybenzoic acid (8), 10 α -hydroxycicosaCal-4-ene-15-aldehyde (9), (2S,3S,4R,10E) -2- [ (2R) -2-hydroxyethyl) -2-ethyl ] -2-methoxy-7-methyl-2-ethyl ] -2-methoxy-methyl-7-4-allyl-15-carbaldehyde (9), 2, 6-methoxy-methyl-4-2-dimethyl-4-2-carbaryl-2, 6-2-methoxy-methyl-4-2-methoxy-2-methyl-7-2-methoxy-2-methyl-7-2-6-2-methoxy-2-methoxy-6-2-methoxy-carbaryl-2-.
The present invention will be described in detail with reference to examples.
Example preparation of effective fractions of Clerodendranthus spicatus
Drying and pulverizing Clerodendranthus spicatus (15Kg) in the shade, soaking in petroleum ether (60-90 deg.C) at room temperature for 3 times, 7 days/time, mixing extractive solutions, and concentrating under reduced pressure to obtain petroleum ether dissolved part extract (97 g).
Concentrating the petroleum ether dissolved part to obtain the effective part of the Desmodium dumuloides anti-insect, repeatedly performing silica gel and Sephadex LH-20 column chromatography to obtain 5 flavonoids, 2 sterol compounds, 1 benzoic acid compound, 1 sesquiterpene compound, 1 alkaloid compound, 1 pyrone compound and 3 chromene compounds, respectively performing silica gel column chromatography to obtain 6,7,8,4 '-tetramethoxyflavone (2)38mg, 2' -hydroxy-4, 4', 5', 6 '-tetramethoxychalcone (5)53mg and 6, 7-dimethoxy-2, 2-dimethylchromene (13)5mg, performing silica gel column chromatography to obtain 6,7,8, 4' -tetramethoxyflavone (2) 2, 4 '-hydroxy-4, 4', 5 ', 6' -tetramethoxychalcone (5) 3mg and 6, 7-dimethoxy-2, 2-dimethylchromene (13)5mg, performing silica gel chromatography to obtain 10: 1, 10 ethyl acetate (15: 1), performing Sephadex LH-20 column chromatography to obtain 1, 6-methoxy-ethyl benzoate (7, 7-methoxy-13), performing silica gel column chromatography to obtain 3-methoxy-ethyl benzoate (5), and separating the Triethoxyquin (5, 7-methoxy-13) ethyl benzoate (5-13) ethyl benzoate, 7-methoxy-13-7-methoxy-13) and 2-methoxy-7-13-methoxy-13-methoxy-7-2, 7-methoxy-7-methoxy-13-methoxy chalcone (7-13, 7-methoxy-7-13, 7-methoxy-2, 7-methoxy-7-2, 7-methoxy-7-methoxy-7-2, 7-methoxy.
The chemical structure is as follows:
Figure DEST_PATH_IMAGE001
example two Studies on the anti-Tenebrio molitor Activity of Petroleum Ether-solubilized fraction of Clerodendrum pseudobulb
1. The experimental method comprises the following steps:
(1) contact killing effect of petroleum ether extract of Clerodendron pseudobulb on tenebrio molitor larvae
The method comprises the steps of selecting 20 larvae with the same size and 3 ages, putting the larvae into a self-made filter screen, quickly taking out the larvae after soaking the larvae in a treatment solution for 10s, sucking redundant liquid medicine by using filter paper, putting the larvae into a culture dish (with the diameter of 9cm) with fresh cabbage or cabbage leaf and padded with moisturizing filter paper, sealing the culture dish by using a preservative film, ventilating by using a needle prick counting hole, repeating the treatment for 3 times, performing the same treatment by using a control solution, observing symptoms of the treated larvae, putting the culture dish into an incubator with the temperature of 25 ℃ and the humidity of 80%, investigating the death condition after 24h and 48h, and calculating the death rate, correcting the death rate and the lethal medium concentration.
(2) Data processing and statistical analysis
The resulting mortality and feeding area data were processed using EXCEL 2003 software and SPSS20 software, analyzed by SPSS20one-way ANOVA, and tested for significance of difference using the new double-range method of Duncan's (P ═ 0.05). Carrying out probit regression analysis to obtain virulence regression equation and LC of the medicament50Values and 95% confidence limits.
Mortality (%). percent (mortality/number of test insects) × 100%
Corrected mortality (%) < treatment-control mortality)/(1-control mortality > × 100%
2. Results of the experiment (see Table 1)
The petroleum ether soluble part of the pseudo-osmyl grass flower obtained in example 1 has obvious contact killing and antifeedant effects on yellow mealworm larvae, and is concentration-dependent.
TABLE 1 contact killing effect of petroleum ether extract of Clerodendrum pseudoodoratum on Tenebrio molitor larvae
Figure BDA0002357169410000071
The above disclosure is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the scope of the present invention, therefore, the present invention is not limited by the appended claims.

Claims (9)

1. The pseudo-osbeckia extract is characterized by comprising the following extraction steps:
(1) adding petroleum ether solvent into the dried powder of the pseudo-osbeckia flowers for extraction to obtain pseudo-osbeckia flowers extract;
(2) filtering and concentrating the extract of the pseudo-osbeckia chinensis bunge under reduced pressure to obtain a petroleum ether dissolved extract;
(3) the petroleum ether dissolved extract is subjected to repeated column chromatography to obtain 5 flavonoids compounds, 2 sterol compounds, 1 benzoic acid compound, 1 sesquiterpene compound, 1 alkaloid compound, 1 pyrone compound and 3 chromene compounds.
2. The pseudo-osbeckia extract according to claim 1, characterized in that: the dried powder of the pseudo-osbeckia flower is obtained by drying the pseudo-osbeckia flower in the shade and then crushing.
3. The pseudo-osbeckia extract according to claim 1, characterized in that: the petroleum ether solvent extraction method comprises room temperature soaking, heating or ultrasonic extraction.
4. The pseudo-osbeckia extract according to claim 1, characterized in that: the temperature of the petroleum ether is 60-90 ℃.
5. The pseudo-osbeckia extract according to claim 1, characterized in that: the volume ratio of the dry powder of the rue-bane flowers to the petroleum ether solvent is 1: 1-1: 10.
6. the pseudo-osbeckia extract according to claim 1, characterized in that: the filler for column chromatography is silica gel or sephadex for column chromatography.
7. The extract of Clerodendron trichotomum flower according to claim 1, wherein 5 flavonoids are characterized by 5,6,4 '-trimethoxy flavone, 6,7,8, 4' -tetramethoxy flavone, 5,6,7,3 ', 4', 5 '-hexamethoxy flavone, 5,6,7,8, 3', 4', 5' -heptamethoxy flavone, 2 '-hydroxy-4, 4', 5 ', 6' -tetramethoxy chalcone, 2 sterols are characterized by β -sitosterol, stigmasterol, 1 benzoic acid compound is characterized by p-methoxybenzoic acid, 1 sesquiterpene compound is characterized by 10 α -hydroxycicosan-4-ene-15-aldehyde, 1 alkaloid compound is characterized by (2S,3S,4R,10E) -2- [ (2R) -2-hydroxytetratetradecanoylamino ] 10-octadecene-1, 3, 4-triol, and 1 pyrone compound is characterized by 6- [ [ (2S) -2-hydroxy-propyl ] -1,3, 4-dimethyl-chromene-2- (2S, 2-methoxy-ethyl) -2, 7-dimethyl-7-2-methoxy ethyl-2-dimethyl chromene, 2-methoxy ethyl-7-2-dimethyl chromene, and 2-methoxy ethyl-7-2-dimethyl chromene.
8. Use of the pseudorue foetida extract according to claims 1-7 in the preparation of a pharmaceutical composition with pharmaceutical excipients or adjuvants in a botanical insecticide.
9. The use of the pseudobedstraw herb extract of claim 8, in combination with pharmaceutical excipients or adjuvants, for preparing a pharmaceutical composition with anti-insect, insecticidal activity against contact and antifeedant action of tenebrio molitor larvae.
CN202010011030.8A 2020-01-06 2020-01-06 Pseudo-osbeckia chinensis flower extract and application thereof Pending CN111116535A (en)

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CN114747580B (en) * 2022-04-27 2024-03-29 河北农业大学 Application of 4-hydroxyoxychlorocarpin in preparation of drug for preventing and treating aphids

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