CN112608362B - Protopanoxadiol type clematis neoglycoside compound, preparation method and application - Google Patents
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Abstract
The invention discloses a protopanoxadiol type clematis neoglycoside compound, a preparation method and application thereof, the compound is a dammarane type tetracyclic triterpene saponin compound which is extracted from clematis plants for the first time and has a protopanoxadiol structure mother nucleus, and the compound is specifically prepared by extracting and eluting the overground part of clematis for multiple times.
Description
Technical Field
The invention belongs to the technical field of pesticides and phytochemistry, and particularly relates to a protopanoxadiol type clematis filamentosa new glycoside compound, and a preparation method and application thereof.
Background
Along with the problems of agricultural product quality safety, environmental safety and the like caused by pesticide residue and drug resistance enhancement, people increasingly favor the research and development of novel botanical insecticides with better environmental compatibility. The method is to excavate and discover a bioactive natural product with a novel structure from plant resources, is a source for creating novel pesticides and a hotspot research field, and is also one of effective ways for developing green and environment-friendly pesticides. At present, a series of botanical pesticide products are developed by taking tea saponin, pyrethrin, azadirachtin, rotenone and the like as effective components.
Clematis aethiopica Clematis is a perennial herbaceous vine plant of Clematis of Ranunculaceae. The stem climbing cylinder is in a brownish black or dark red surface, has six obvious longitudinal lines, pinnate compound leaves, a flower bell shape, reverse rolling at the top end, 4 sepals and pink to purple red, and has high ornamental value. The Chinese medicinal composition is mainly distributed in ditch sides, hillside wastelands and shrubs of Shaanxi, Yunnan, Sichuan, Guizhou, Hunan and other places, is one of the most widely distributed varieties of the clematis in China, and has the effects of removing blood stasis, promoting urination and detoxifying.
Disclosure of Invention
Based on the above purposes, the invention provides a protopanoxadiol type clematis neoglycoside compound, a preparation method and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
the protopanoxadiol type clematis neoglycoside compound has a chemical structural formula shown as the following formula (I):
the invention also discloses a preparation method of the protopanoxadiol type clematis neoglycoside compound, which comprises the following steps:
step 1, collecting fresh clematis filamentosa, drying, crushing, cold-soaking and extracting crushed materials with ethanol or methanol, replacing a solvent once every 4-7 days, extracting for 3-4 times, combining extracting solutions and concentrating to obtain an extract;
step 2, dispersing the extract in water, preparing the extract into a suspension state, sequentially extracting the suspension state with petroleum ether, ethyl acetate and n-butanol, and concentrating the n-butanol extract to obtain the clematis filamentosa total saponin;
step 3, carrying out normal-phase gradient elution on the clematis filamentosa total saponins, wherein the eluent comprises dichloromethane, methanol and water, and the dichloromethane, the methanol and the water are mixed according to the volume ratio of 100:1: 0-1: 1: 0.5; fraction 1 is obtained;
and 4, carrying out reversed-phase gradient elution on the fraction 1, wherein an eluent comprises methanol and water, and the volume ratio of the methanol to the water is 30: 70-100: 0; fraction 2 is obtained;
and step 5, performing gradient elution on the fraction 2 by adopting a liquid chromatography, wherein the liquid chromatography conditions are as follows: eluents include methanol, water and trifluoroacetic acid, the methanol: water: the volume ratio of trifluoroacetic acid is 50: 50: 0.1 to 100: 0: 0.1; the detection wavelength is 210-254 nm; the flow rate of the eluent is 8-10 mL/min; obtaining the new glycoside compounds of clematis filamentosa.
Preferably, the solvent in the step 1 is 65-80% of ethanol or 65-80% of methanol; the volume ratio of the smashed verbena and a methanol or ethanol solvent is 1: 2-1: 3.
Preferably, in the step 1, the crushed clematis filamentosa is sieved by a sieve with 30-50 meshes.
Preferably, the extraction process in the step 2 specifically comprises: extracting with petroleum ether for 3-4 times, extracting the lower-layer liquid phase after the petroleum ether extraction with ethyl acetate for 3-4 times, and extracting the lower-layer liquid phase after the ethyl acetate extraction with n-butyl alcohol for 3-4 times.
Preferably, the volume ratio of the petroleum ether, the ethyl acetate and the n-butanol in the step 2 is 1:1: 1.
Preferably, the normal phase gradient elution in the step 3 adopts a normal phase silica gel column; the reversed phase gradient elution in the step 4 adopts a C-18 reversed phase column; the step 5 adopts YMC-C18 chromatographic column for liquid phase elution.
Further, fraction 2 of step 4 is eluted by sephadex chromatography, and the eluent comprises methanol and water, wherein the volume ratio of methanol to water is 1: 1; fraction 3 is obtained; fraction 3 was eluted by liquid chromatography in step 5.
The invention also discloses the application of the protopanoxadiol type clematis neoglycoside compound in the aspects of insecticide and antifeedant.
Compared with the prior art, the invention has the beneficial effects that:
the invention extracts a protopanaxadiol type clematis neoglycoside compound from clematis plants for the first time, the new compound shows good stomach toxicity activity, repellent activity and food refusal activity to lepidoptera pests diamondback moth and hemiptera pests pea aphid, provides an important theoretical basis for further developing novel botanical insecticides by taking the clematis neoglycoside compound as an effective component, and provides a new strategy and thought for green prevention and control of crop pests and quality safety guarantee of agricultural products.
Detailed Description
The invention extracts a protopanaxadiol type clematis neoglycoside compound from clematis multocida for the first time, and the compound has a chemical structural formula shown as the following formula (I):
the protopanaxadiol type clematis neoglycoside compound is prepared by the following steps:
step 1, collecting fresh clematis filamentosa, drying in the shade, crushing, carrying out cold-leaching extraction on the crushed material by using an ethanol or methanol solvent, replacing the solvent once every 4-7 days, extracting for 3-4 times, and combining the concentration of the extracting solution to obtain an extract;
after crushing the clematis filamentosa in the step, sieving the crushed clematis filamentosa by a sieve of 30-50 meshes to obtain a crushed substance; the extraction solvent is preferably 65-80% of ethanol or 65-80% of methanol by volume, wherein the volume ratio of the herba clematidis multocida crushed material to the ethanol solvent is 1: 2-1: 3.
And 2, dispersing the extract in water, preparing the extract into a suspension state, sequentially extracting the suspension state with petroleum ether, ethyl acetate and n-butyl alcohol for multiple times, and then combining and concentrating n-butyl alcohol extracts to obtain the clematis filamentosa total saponin. The preferred extraction process of the invention is specifically as follows: extracting with petroleum ether for 3-4 times, extracting the lower-layer liquid phase after the petroleum ether extraction with ethyl acetate for 3-4 times, and extracting the lower-layer liquid phase after the ethyl acetate extraction with n-butyl alcohol for 3-4 times. The volume ratio of the petroleum ether to the ethyl acetate to the n-butanol is 1:1: 1.
The obtained clematis total saponins are subjected to normal phase elution, reversed phase elution and liquid chromatography elution in sequence to obtain a new compound, and the specific process is as follows:
step 3, carrying out normal-phase gradient elution on the clematis filamentosa total saponins, preferably carrying out elution by using a normal-phase silica gel column, wherein the eluent comprises dichloromethane, methanol and water, and the dichloromethane, the methanol and the water are mixed according to the volume ratio of 100:1: 0-1: 1: 0.5;
step 4, carrying out reversed-phase gradient elution on the fraction 1, preferably selecting a C-18 reversed-phase column, wherein an eluent comprises methanol and water, and the volume ratio of the methanol to the water is 30: 70-100: 0; fraction 2 is obtained;
step 5, performing gradient elution on fraction 2 by adopting a liquid chromatography, preferably performing gradient elution by adopting a YMC-C18 chromatographic column; the liquid chromatography conditions of this step were: eluents include methanol, water and trifluoroacetic acid, the methanol: water: the volume ratio of trifluoroacetic acid is 50: 50: 0.1 to 100: 0: 0.1; the detection wavelength is 210-254 nm; the column temperature is normal temperature, and is generally 20-30 ℃; the eluent has a flow rate of 8-10 mL/min and a retention time of 35-50 min to obtain the acteoside compound.
Preferably, fraction 2 may be eluted by sephadex chromatography after the reverse phase gradient elution in step 4, wherein the eluent comprises methanol and water, and the volume ratio of methanol to water is 1: 1; fraction 3 is obtained; further, the purity of the compound can be further improved by subjecting fraction 3 to gradient elution by liquid chromatography described in step 5.
Experiments show that the protopanoxadiol type clematis neoglycosides compound obtained by the invention is applied to the aspects of insecticide and antifeedant, in particular to the aspects of insecticide for preventing and controlling aphids and plutella xylostella and antifeedant.
In addition, the novel compound is a dammarane type tetracyclic triterpene saponin compound with a protopanaxadiol structure, the structure of the dammarane type tetracyclic triterpene saponin compound is the same as that of American ginseng saponin F1, and the structural difference is only that glucose at the C-3 position of a glycosyl part is substituted by arabinose. The clematis filamentosa is one of the most common varieties of clematis plants, the plant resources are rich, the new acteoside A discovered by the invention can be used as a resource substitute obtained by the same active ingredients of the rare Chinese medicinal materials such as American ginseng and the like, and has remarkable economic benefit.
The following embodiments of the present invention are provided, and it should be noted that the present invention is not limited to the following embodiments, and all equivalent changes based on the technical solutions of the present invention are within the protection scope of the present invention.
Example 1
The embodiment discloses a preparation method of protopanoxadiol type clematis neoglycosides compounds, which comprises the following steps:
(1) 70% extract of clematis filamentosa: drying freshly collected clematis filamentosa in the shade, crushing by using a plant crusher, sieving by using a 40-mesh sieve, and carrying out cold leaching extraction by using 70% ethanol, wherein the volume ratio of the clematis filamentosa crushed material to the 70% ethanol is 1: 2-3, replacing the solvent every 4-7 days, extracting for 3-4 times, and finally merging and concentrating to obtain the 70% extract.
(2) The preparation of the clematis filamentosa total saponins comprises the following steps: and (3) dispersing 70% of the extract in water, preparing the mixture into a suspension state, sequentially extracting the suspension state for 3-4 times by using petroleum ether, ethyl acetate and n-butyl alcohol with equal volumes, and combining and concentrating n-butyl alcohol extracts to obtain the clematis total saponin.
(3) Normal phase column chromatographic separation: separating herba clematidis total saponin by normal phase silica gel column chromatography, separating with dichloromethane: methanol: carrying out gradient elution on water according to the volume ratio of 100:1: 0-1: 1:0.5, wherein dichloromethane: methanol: the volume ratio of water is 7: 3: 0.3 elution gave fraction 1.
(4) And (3) reversed-phase column chromatographic separation: fraction 1 was subjected to C-18 reverse phase column chromatography eluting with methanol: water in a volume ratio of 30: 70-100: 0, wherein fraction 2 is methanol to water 70: 30 is obtained by elution.
(5) And (3) gel column chromatographic separation: fraction 2 was chromatographed on a Sephadex LH-20 Sephadex column, purified on methanol: water is used as eluent, and the volume ratio of methanol to water is 1:1, obtaining fraction 3.
(6) HPLC preparative separation: preparative HPLC on fraction 3 was prepared as follows: the chromatographic column is YMC-C18 chromatographic column (250X 20mm,5 μm); the eluent is methanol: water: trifluoroacetic acid is 50: 50: 0.1 to 100: 0: 0.1 gradient elution; the detection wavelength is 210 nm-254 nm; the column temperature is normal temperature; the flow rate is 9 mL/min; the sample injection amount is 500 mu L; the retention time is 35-50 min, and the new acteoside compound can be obtained.
The structure of the clematis filamentosa neoglycosides obtained in this example was identified as follows:
the reaction was performed by HRESIMS, ESIMS,1H-NMR，13C-NMR，HSQC，HMBC，1H-1and (4) identifying spectral data such as H COSY, NOESY and the like.
The obtained compound is white amorphous powder, and the Liebermann-Burchard reaction is positive. ESIMS (+) gives the compound excimer peak M/z 811[ M + Na ]]+And 1599[2M + Na]+The excimer ion peak M/z 823[ M + Cl ] of the compound is given in combination with ESIMS (-)]+The molecular weight of the compound is presumed to be 788. HRESIMS (+) gave the combined excimer ion peak M/z 811.4775[ M + Na ]]+(calculated value: C)41H72O14Na,811.4820),789.4951[M+H]+(calculated value: C)41H73O14789.5000), the molecular formula of the compound is presumed to be C41H72O14。
1In the H-NMR spectrum, signals of 8 methyl hydrogens connected with quaternary carbon are shown: delta 0.97(3H, s, H)3-18)、0.83(3H,s,H3-19)、1.47(3H,s,H3-21)、1.53(3H,s,H3-26)、1.56(3H,s,H3-27)、1.25(3H,s,H3-28)、1.07(3H,s,H3-29) and 0.96(3H, s, H)3-30). In addition to this, the present invention is,1the H-NMR spectrum also gives the two terminal proton signals for arabinose and glucose: δ 4.99(1H, d, J ═ 5.8Hz) and 5.20(1H, d, J ═ 7.7Hz), in combination with HSQC, respectively13The delta 105.2 in the C-NMR spectrum corresponds to the terminal carbon signal of the sugar at 106.4. Determination of Arar from coupling constantsThe primary sugar is in the alpha configuration and the glucose is in the beta configuration. After acid hydrolysis, the compound is compared with a standard product, and the ratio of L-arabinose (L-Ara) to D-glucose (D-Ara) is detected to be 1:1, thereby determining the absolute configuration of the saccharide. The compound structure also contains 5 vicinal oxygen carbon signals, including two methine vicinal oxygen carbon C-3 (delta 89.1) and C-12 (delta 71.4) which are usually contained by protopanaxadiol type triterpene sapogenin, and a vicinal oxygen quaternary carbon signal at C-20 (delta 73.6) position. The remaining two vicinal oxygens are the vicinal oxymethylene carbon at the C-24 (. delta.80.5) position and the vicinal quaternary carbon signal at the C-25 (. delta.73.1) position, respectively.
The above spectral data and literature report of American ginseng saponin F1[3 β,12 β,20(S),24 ξ, 25-pentahydroxy dammar-3-O- β -D-glucopyranoside- (1 → 2) -D-glucopyranoside]The sapogenins have the same structure, and are different in that C-3 glucose is replaced by arabinose [ Helxihua, Liyaping, Limiao, Liuyongqiang, Studies on saponins of American ginseng fruit, Chinese medicinal materials 2000,31(11),801-]. The order of linkage of the sugars is HMBC to1H-1H COSY related signal is determined, the terminal hydrogen H ' -1 of arabinose and aglycone C-3 show HMBC correlation, H ' -1 and H ' -2 (delta 4.62) show1H-1H COSY is related, H '-2 is related to the terminal carbon C-1' of glucose to show HMBC, the terminal hydrogen H '-1 of glucose is related to C-2' (delta 81.5) of arabinose to show HMBC, and then the connection between glucose and arabinose in a 1 → 2 connection mode and the C-3 position of aglycone is determined.
The chemical shift at C-24 position in the 24(S) configuration is between 77.0-78.2, while the chemical shift at C-24 position in the 24(R) configuration is between 79.9-80.6, and the chemical shift at C-24 position in the compound is delta 80.5, so that the C-24 position is determined to be the R configuration [ Li M, Liu F, Jin YR, Wang XZ, Wu Q, Liu Y, Li XW.five new tertiary specific peptides from the drugs of the metabolism of the facial patches and the anti-additive formation activity. plant Med,2017,83, 351-357-]. The configuration at C-20 is designated as S configuration because the chemical shift at C-21 is 27.8, and in the NOESY pattern, H-17 (. delta.4.62) is compared with H3The correlation peak at-21 (. delta.1.47) also further indicates the S configuration at position C-20.
In combination with the HSQC, the device can be used for,HMBC，1H-1the spectral data of H COSY, NOESY, etc., and the spectral data of the compounds are shown in Table 1.
TABLE 1 New glycoside A of clematis filamentosa1H-NMR (500MHz) and13C-NMR (125MHz) data (C)5D5N)
Combining the above analyses, the compound structure was identified as 3 β,12 β,20(S),24(R), 25-pentahydroxy dammar-3-O- α -L-arabinopyranoside- (1 → 2) - β -D-glucopyranoside, named verbascoside a, with the following structure confirmation:
example 2
This example is carried out to test the insecticidal activity of the neoglycoside soloectochilus formosanus compound prepared in example 1 on Aphis fabae:
according to the artificial feed mixing method, the concrete references are as follows: geyter ED, Smaghe G, Rahbe Y, Geelen D.Triterpen saponin of Quillaja saponaria show Stringaphasic and term activity against the pea aphid Acyrthososporin pisum.Pest Man Sci 2012; 68:164 and 169, taking the pea aphid as the tested pest, and testing the stomach toxicity and repellent activity of the verbascoside A.
The results show that the compound prepared in example 1 has LC at 72h for Piper pisum50It was 0.364 mg/mL. The repellent rates of 12h at concentrations of 2, 1, 0.5, 0.25, 0.125mg/mL were 100%, 80%, 63.6%, 57.1% and 33.3%, respectively.
Example 3
This example demonstrates the insecticidal activity of the neoglycoside soloectochilus formosanus compound prepared in example 1 against plutella xylostella:
according to the leaf disk method, specific references: tian X, Li Y, Hao N, Su X, Du J, Hu J, Tian X, the anti-fiedant, inductive and inductive growth inhibitory activities of ternary saponin from Clematias aethiophila Turcz against Plutella (L.). Pest Man Sci 2021; 77: 455-463, and taking diamondback moth as the tested pest, the stomach toxicity and the antifeedant activity of the new acteoside are tested.
The result shows that the compound prepared in the example 1 has the antifeedant rate of 70-92% to the plutella xylostella for 24h when the concentration is 1 mg/mL; when the concentration is 2mg/mL, the corrected mortality rate of the diamondback moth for 72 hours is 65-87%.
It can be seen that the novel compound of the invention shows good stomach toxicity activity, repellent activity and feeding deterrent activity on lepidoptera pests such as diamondback moth and hemiptera pests such as pea aphid.
Claims (7)
1. The protopanoxadiol type clematis madaio neoglycoside compound is characterized by having a chemical structural formula shown as the following formula (I):
2. a process for producing protopanaxadiol type clematis neoglycosides according to claim 1, comprising the steps of:
step 1, collecting fresh clematis filamentosa, drying, crushing, cold-soaking and extracting crushed materials with ethanol or methanol, replacing a solvent once every 4-7 days, extracting for 3-4 times, combining extracting solutions and concentrating to obtain an extract;
step 2, dispersing the extract in water, preparing the extract into a suspension state, sequentially extracting the suspension state with petroleum ether, ethyl acetate and n-butanol, and concentrating the n-butanol extract to obtain the clematis filamentosa total saponin;
step 3, carrying out normal-phase gradient elution on the clematis filamentosa total saponins, wherein the eluent is a mixed solution of dichloromethane, methanol and water, and the dichloromethane, the methanol and the water are mixed according to the volume ratio of 100:1: 0-1: 1: 0.5; fraction 1 is obtained; the normal phase gradient elution adopts a normal phase silica gel column;
step 4, carrying out reversed-phase gradient elution on the fraction 1, wherein an eluent is a mixed solution of methanol and water, and the volume ratio of the methanol to the water is 30: 70-100: 0; fraction 2 is obtained; the reversed phase gradient elution adopts a C-18 reversed phase column;
fraction 2 was eluted by sephadex chromatography eluting with a mixture of methanol and water at a methanol to water volume ratio of 1: 1; fraction 3 is obtained; the Sephadex LH-20 Sephadex chromatographic column is adopted for elution of the Sephadex chromatographic column;
and 5, performing gradient elution on the fraction 3 by adopting a liquid chromatography, wherein the liquid chromatography conditions are as follows: the eluent is a mixed solution of methanol, water and trifluoroacetic acid, wherein the ratio of methanol: water: the volume ratio of trifluoroacetic acid is 50: 50: 0.1 to 100: 0: 0.1; the detection wavelength is 210-254 nm; the flow rate of the eluent is 8-10 mL/min; carrying out liquid phase elution by adopting a YMC-C18 chromatographic column; obtaining the new glycoside compounds of clematis filamentosa.
3. The method for preparing protopanoxadiol type clematis neoglycosides according to claim 2, wherein the solvent in the step 1 is 65 to 80% ethanol or 65 to 80% methanol; the volume ratio of the smashed verbena and a methanol or ethanol solvent is 1: 2-1: 3.
4. The method for producing protopanaxadiol type clematis neoglycosides according to claim 2, wherein the pulverized clematis filamentosa is sieved with a 30-50 mesh sieve in the step 1.
5. The method for preparing protopanoxadiol type clematis neoglycosides according to claim 2, wherein the extraction process in the step 2 is specifically as follows: extracting with petroleum ether for 3-4 times, extracting the lower-layer liquid phase after the petroleum ether extraction with ethyl acetate for 3-4 times, and extracting the lower-layer liquid phase after the ethyl acetate extraction with n-butyl alcohol for 3-4 times.
6. The method for producing protopanaxadiol type clematis neoglycosides according to claim 2 or 5, wherein the volume ratio of petroleum ether, ethyl acetate and n-butanol in the step 2 is 1:1: 1.
7. Use of the protopanoxadiol type clematis neoglycosides according to claim 1 as insecticides and antifeedants.
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| CN108271786A (en) * | 2018-02-16 | 2018-07-13 | 烟台大学 | A kind of new application of ocotillol types compound as agricultural bacteriocide |
| CN110845566A (en) * | 2019-12-03 | 2020-02-28 | 广西壮族自治区中国科学院广西植物研究所 | Dammarane triterpene glycoside compound and preparation method and application thereof |
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| CN108271786A (en) * | 2018-02-16 | 2018-07-13 | 烟台大学 | A kind of new application of ocotillol types compound as agricultural bacteriocide |
| CN110845566A (en) * | 2019-12-03 | 2020-02-28 | 广西壮族自治区中国科学院广西植物研究所 | Dammarane triterpene glycoside compound and preparation method and application thereof |
Non-Patent Citations (3)
| Title |
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| "Antifeedant and ovicidal activities of ginsenosides against Asian corn borer, Ostrinia furnacalis (Guenee)";Shuangli Liu et al.;《PLoS ONE》;20190215;第14卷(第2期);第e0211905页 * |
| "Bio-guided isolation of plant growth regulators from allelopathic plant-Codonopsis pilosula: phyto-selective activities and mechanisms";Min Xie et al.;《RSC Advances》;20181231;第8卷;第13649-13655页 * |
| "西洋参果皂苷成分的研究";郝秀华等;《中草药》;20001231;第31卷(第11期);第801-803页 * |
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