CN108084244B - Triterpenoid saponin compound and preparation method and application thereof - Google Patents

Triterpenoid saponin compound and preparation method and application thereof Download PDF

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CN108084244B
CN108084244B CN201711475732.6A CN201711475732A CN108084244B CN 108084244 B CN108084244 B CN 108084244B CN 201711475732 A CN201711475732 A CN 201711475732A CN 108084244 B CN108084244 B CN 108084244B
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aqueous solution
water
compound
ethanol
eluent
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CN108084244A (en
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余小青
辛振强
周霖
钱勇
谢天培
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SHANGHAI BAINIAN SHIDANDE INSPECTION TECHNOLOGY CO LTD
Shanghai Nature Standard R&d And Biotech Co ltd
Shanghai Standard Technology Co ltd
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SHANGHAI BAINIAN SHIDANDE INSPECTION TECHNOLOGY CO LTD
Shanghai Nature Standard R&d And Biotech Co ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J63/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008Expansion of ring D by one atom, e.g. D homo steroids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • C07H1/06Separation; Purification
    • C07H1/08Separation; Purification from natural products
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/24Condensed ring systems having three or more rings
    • C07H15/256Polyterpene radicals

Abstract

The invention relates to the field of medicines, in particular to a novel triterpenoid saponin compound and a preparation method and application thereof. The invention provides a compound, and the structural formula of the compound is shown as a formula I. The compound provided by the invention has molluscicidal activity with certain strength, and can show molluscicidal activity with different strengths under different drug solubilities.

Description

Triterpenoid saponin compound and preparation method and application thereof
Technical Field
The invention relates to the field of medicines, in particular to a novel triterpenoid saponin compound and a preparation method and application thereof.
Background
Saponins (saponin) is also called saponin, is a special glycoside widely existing in plant kingdom, and its aqueous solution can produce lasting soap-like foam after shaking, so that it is named. Saponins have attracted more and more attention as a bioactive substance. According to the structure of sapogenins formed by hydrolysis of saponins, they can be divided into triterpenoid saponins (triterpenoid saponins) and steroidal saponins (steroidal saponins). Triterpenoid saponins are compounds whose basic nucleus consists of about 30 carbon atoms, and are often present in plants in free form or in the form of glycosides or esters bound to sugars.
Disclosure of Invention
In view of the above-mentioned disadvantages of the prior art, the present invention aims to provide a triterpenoid saponin compound, which is used for solving the problems in the prior art.
To achieve the above and other related objects, a first aspect of the present invention provides a compound having good molluscicidal activity. The compound provided by the invention is generally a triterpenoid saponin compound, and the structural formula of the compound is shown as the formula I:
in a second aspect, the present invention provides a process for the preparation of said compound, comprising: extracting the compound from kudzuvine root.
In some embodiments of the invention, the method of making comprises:
(1) extracting radix Puerariae with ethanol, and concentrating the extractive solution;
(2) extracting the concentrated extract, and desolventizing the organic phase;
(3) adsorbing and eluting the product obtained by desolventizing through resin, and concentrating the eluent;
(4) purifying the concentrated eluent to obtain the compound.
The Kudzuvine root is commonly referred to as the root of Kudzuvine. Pueraria peduncularis (Grah. exBnth) Benth) is a herbaceous plant wound by Pueraria of Leguminosae (Leguminosae), also called Yunnan Pueraria lobata, white Pueraria peduncularis and red Pueraria peduncularis (Yunnan), and is mainly distributed in Sichuan, Tibet, Guangxi, Guizhou and Yunnan of China, and the distribution is the most extensive in Yunnan.
Those skilled in the art can select a suitable kind of solvent and use amount for alcohol extraction so that soluble components in the substance to be extracted can be sufficiently dissolved out.
In some embodiments of the present invention, the solvent used for alcohol extraction may be an alcohol solvent such as methanol, ethanol, or the like, or an aqueous solution thereof, or the like. Preferably, the solvent used for alcohol extraction may be 70-85 v/v% ethanol aqueous solution.
In some embodiments of the present invention, the volume ratio of the solvent to pueraria lobata is 8-12: 1, the extraction condition is from room temperature to the reflux temperature of the solvent, specifically from 55 ℃ to 65 ℃, and the extraction times are more than two.
In some embodiments of the present invention, the extract obtained by the alcohol extraction is further subjected to solid-liquid separation.
In some embodiments of the present invention, the concentrated extract is extracted with n-butanol and water, wherein the volume ratio of n-butanol to water is 1: 2-10, preferably 1: 2-3.
In some embodiments of the invention, the organic phase is desolventized to an extract.
In some embodiments of the invention, the product obtained by desolventizing is dissolved in water, adsorbed by macroporous resin, and subjected to gradient elution by using a water-ethanol system.
In some embodiments of the invention, the macroporous resin is AB-8 type macroporous resin, when gradient elution is performed by adopting a water-ethanol system, eluents are water, 25-35 v/v% ethanol aqueous solution, 65-75 v/v% ethanol aqueous solution and more than or equal to 90 v/v% ethanol aqueous solution respectively, and the elution part of the more than or equal to 90 v/v% ethanol aqueous solution is collected and merged for subsequent treatment.
In some embodiments of the invention, the concentrated eluate is prepared by purification by medium pressure preparative chromatography and/or high performance liquid chromatography.
In some embodiments of the present invention, the specific method for purifying the concentrated eluate is: purifying the concentrated eluate by medium pressure preparative chromatography, performing gradient elution with methanol-water as mobile phase, and purifying the eluate by high performance preparative liquid chromatography.
In some embodiments of the invention, the packing material of the medium pressure preparative chromatography is octadecylsilane chemically bonded silica (C18), the eluents are 50-60 v/v% methanol aqueous solution, 75-85 v/v% methanol aqueous solution and 100% methanol respectively, and the parts of the 75-85 v/v% methanol aqueous solution are collected and combined for subsequent treatment.
In some embodiments of the invention, the packing material of the HPLC is octadecylsilane chemically bonded silica (C18), and the eluent is 30-40 v/v% acetonitrile water solution and is eluted at a constant speed with a flow rate of 50-70 ml/min.
The third aspect of the invention provides the application of the compound in oncomelania killing or preparing oncomelania killing medicines. The compound provided by the application has molluscicidal activity with certain intensity, and can show molluscicidal activity with different intensities under different drug solubilities, wherein the molluscicidal activity generally refers to the property that a substance can inhibit the growth of snails and/or cause the death of snails, and the snails can be, for example, ampullaria gigas (Lamarck) and the like.
The invention discloses a novel oleanane type triterpenoid saponin compound separated from kudzuvine root, which is obtained by crude extraction, repeated extraction, macroporous resin adsorption, medium-pressure liquid chromatography and high-performance preparative liquid chromatography separation of the kudzuvine root, and the structure of the compound is identified by adopting 1D and 2D-NMR techniques, wherein the name of the compound is 3-O- β -D-glucopyranose (1-2) - β -D-glucopyranose (1-2) [ β -D-glucopyranose (1-3) - β -D-glucopyranosyl uronic acid ] -12 oleanene-30-formic acid (3-O- β -D-glucopyranosyl- (1-2) - β -D-glucopyranosyl (1-2) [ β -D-glucopyranosyl (1-3) - β -D-glucopyranosyl ] -12-olenaceae-30-oic acid), and the structural formula I is shown in the specification.
Drawings
FIG. 1 shows an embodiment of the present invention1H-NMR spectrum(pridine-d5) The results are shown schematically.
FIG. 2 shows an embodiment of the present invention13C-NMR spectrum(pridine-d5) The results are shown schematically.
FIG. 3 shows the principle-d of example 1H-1HCOSY spectrum of the present invention5) The results are shown schematically.
FIG. 4 shows an embodiment of HSQC spectra (pridine-d)5) The results are shown schematically.
FIG. 5 shows an embodiment of the invention, HMBC spectrum (pridine-d)5) The results are shown schematically.
FIG. 6 shows the unique spectrum (pridine-d) of the present invention5) The results are shown schematically.
FIG. 7 is a diagram showing the Q-TOFspectrum result of the present invention.
FIG. 8 is a schematic diagram of the H-C correlation of HMBC according to an embodiment of the present invention.
FIG. 9 is a schematic diagram showing H-H correlation of NOESY according to the embodiment of the present invention.
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
It is to be understood that the processing equipment or apparatus not specifically identified in the following examples is conventional in the art.
Furthermore, it is to be understood that one or more method steps mentioned in the present invention does not exclude that other method steps may also be present before or after the combined steps or that other method steps may also be inserted between these explicitly mentioned steps, unless otherwise indicated; it is also to be understood that a combined connection between one or more devices/apparatus as referred to in the present application does not exclude that further devices/apparatus may be present before or after the combined device/apparatus or that further devices/apparatus may be interposed between two devices/apparatus explicitly referred to, unless otherwise indicated. Moreover, unless otherwise indicated, the numbering of the various method steps is merely a convenient tool for identifying the various method steps, and is not intended to limit the order in which the method steps are arranged or the scope of the invention in which the invention may be practiced, and changes or modifications in the relative relationship may be made without substantially changing the technical content.
Example 1
Preparation of the compound:
(1) weighing pulverized radix Puerariae, adding 8-12 times volume of 70-85% ethanol, stirring, reflux extracting at 60 deg.C for 2 times (4 hr each time), filtering, mixing filtrates, and recovering ethanol under reduced pressure to obtain 1.5kg medicinal liquid;
(2) repeatedly extracting the liquid medicine obtained in the step (1) with n-butanol and water for multiple times, wherein the volume ratio of the n-butanol to the water is 1:2, and concentrating the extract liquid to obtain an extract, so as to obtain 800g of an n-butanol extract;
(3) dispersing the extract obtained in the step (2) with 10L of water, then carrying out macroporous resin adsorption, wherein the type of the used macroporous resin is AB-8, carrying out gradient elution with water-ethanol, wherein eluates are respectively water, 30 v/v%, 70 v/v% and 95 v/v% ethanol water solution, collecting 95 v/v% ethanol elution parts, merging, and carrying out reduced pressure recovery to obtain 125g of liquid medicine for later use;
(4) purifying the liquid medicine obtained in the step (3) by using a medium-pressure liquid chromatograph (medium-pressure C18, Suzhou Huitong chromatography separation and purification Limited, and the filler is octadecylsilane chemically bonded silica (C18)), performing gradient elution by using methanol-water as a mobile phase, wherein the eluates are 55 v/v%, 80 v/v% methanol aqueous solution and 100% methanol respectively, collecting the eluate of the combined solution 80 v/v% methanol aqueous solution, and recovering 4g of liquid medicine under reduced pressure for later use;
(5) refining the liquid medicine obtained in the step (3) by using a high performance preparative liquid chromatograph (Shimadzu LC-20AP series, the filler is octadecylsilane chemically bonded silica (C18)), and the eluent is 35 v/v% acetonitrile and is eluted at a constant speed, wherein the flow rate is 70ml/min, so that 116mg of the target compound with the purity of more than 98% is obtained.
And (3) structural identification:
the compound is white powder, the Liebermann-Burchard reaction is orange red, and the Molish reaction is positive, so the compound can be a triterpenoid saponin compound. HR-ESI-MS M/z 1131.5232[ M-H ] -, calculated 1131.5223, combined with 1H-and 13C-NMR spectroscopy determined the compound to be of formula C54H84O25, calculated to have an unsaturation of 11. The 1H-NMR spectrum shows 7 monomodal methyl groups: δ 0.78(3H, s), δ 0.92(3H, s), δ 1.04(3H, s), δ 1.19(3H, s), δ 1.20(3H, s), δ 1.28(3H, s). 5.42(1H, br s) shows that there are olefinic hydrogens in the compound and are intra-cyclic olefinic bonds (delta > 5). In the HMBC spectrum, CH2 δ 2.78(1H, d, J ═ 15.5Hz), δ 1.96(1H, d, J ═ 15.1Hz), and the methyl group δ 1.19(3H, s) at position 28 are all remotely related to the quaternary carbon of δ 215.7, and the methyl group δ 1.44(3H, s) at position 29 of the HMBC spectrum are remotely related to the quaternary carbon of 180.9, indicating that the compound is carbonyl at position 16 and carboxyl at position 30. Therefore, the compound aglycone parent nucleus is 12 oleanolic acid-30-formic acid.
1In the H-NMR spectrum, the delta 4.99(1H, D, J-7.6 Hz), the delta 5.29(1H, D, J-7.7 Hz), the delta 5.63(1H, D, J-7.7 Hz), the delta 5.66(1H, D, J-7.6 Hz) and the delta 5.66(1H, D, J-7.6 Hz) have four terminal hydrogen groups, in the 13C-NMR spectrum, the delta 103.0, delta 104.8, 104.8 and 105.0 have four terminal carbon groups, which shows that the compound is a tetraglycoside, in the 13C-NMR spectrum, the delta 105-delta 62.4 has 24 carbon signals, in addition, the proton hydrogen delta 4.66 on the sugar in the HMBC spectrum has a remote relation with the carboxyl carbon delta 172.6, 1 glucuronic acid, and the split and coupling constants (1H, D, J-7.6 Hz), (1H, D, J-7.7 aglycone) can be inferred that the four sugar configurations are all related to delta 5H- β, D, J-5H, delta-7.7H, delta-20H, delta-5H-27H-The radical hydrogen delta 5.66 is remotely related to the C280.5 on the sugar, so that four sugars are connected in a manner that the sugar with the terminal hydrogen delta 4.99 is connected with the aglycone C-3 in a 1-3 manner, the sugar with the terminal hydrogen delta 5.29 is connected with the sugar C-3 position with the terminal hydrogen delta 4.99 in a 1-3 manner, the sugar with the terminal hydrogen delta 5.66 is connected with the sugar C-2 position with the terminal hydrogen delta 4.99 in a 1-2 manner, and the sugar with the terminal hydrogen delta 5.63 is connected with the sugar C-2 position with the terminal hydrogen delta 5.66 in a 1-2 manner, so that the connection sequence of the sugar chains is 3-O- β -D-glucopyranose (1-2) - β -D-glucopyranose (1-2) [ β -D-glucopyranose (1-3) - β -D-glucopyranose uronic acid]。
In summary, the structure of KGC-32 was identified as 3-O- β -D-glucopyranose (1-2) - β -D-glucopyranose (1-2) [ β -D-glucopyranose (1-3) - β -D-glucopyranosyl uronic acid ] -12-oleanene-30-carboxylic acid, and the data of the 1H-NMR and 13C-NMR spectra of this compound are shown in Table 1.
TABLE 1
Example 2
The target compound prepared in example 1 was subjected to a molluscicidal activity test, which specifically comprises the following steps:
collecting Pomacea canaliculata with a shell diameter of 0.5 +/-0.1 cm in Guanghan and Xingzhou provinces in 2017 in 6 months, feeding with water and cabbage at a constant temperature of 25 ℃ for 5 days, adapting to a laboratory environment for later use, and removing the dead Pomacea canaliculata.
Preparing a target solution: accurately weighing appropriate amount of 10mg and 30mg of the target respectively, dissolving with DMSO solution, and preparing into 10mg-1And 30mg.L-1The other group uses DMSO solution without adding the target as a negative control; 20 ampullaria gigas are put into an experimental plate with 6 holes, and 10mg.L is added into 2 holes-12 wells with 30mg.L of the target solution-1The other 3 wells were filled with a negative control solution without the target, and the solution was dividedMortality after 24 hours, 48 hours and 72 hours was observed
The experimental results are as follows: 10mg.L-1Has a mortality rate of 26.25% after 72 hours, 30mg.L-1The mortality rates of the target solution of (1) after 24 hours, 48 hours and 72 hours were 21.25%, respectively; 57.5 percent and 71.25 percent.
TABLE 2
As can be seen from the related data in Table 2, the novel compound provided by the invention has better molluscicidal activity and drug solubility of 30mg.L-1The molluscicidal activity showed different intensities within 24 hours, 48 hours and 72 hours respectively.
In conclusion, the present invention effectively overcomes various disadvantages of the prior art and has high industrial utilization value.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.

Claims (6)

1. A compound having a structural formula as shown in formula I:
2. a process for the preparation of a compound according to claim 1, which process comprises:
(1) extracting radix Puerariae with ethanol, concentrating the extractive solution, wherein the solvent used in the extraction is alcohol solvent or their aqueous solution, and the extraction condition is from room temperature to solvent reflux temperature;
(2) extracting the concentrated extracting solution, desolventizing an organic phase, extracting the concentrated extracting solution by using n-butanol and water, wherein the volume ratio of the n-butanol to the water is 1: 2-10, and desolventizing the organic phase to obtain an extract;
(3) adsorbing and eluting the product obtained by desolventizing through resin, concentrating eluent, dissolving the product obtained by desolventizing in water, adsorbing through macroporous resin, performing gradient elution by adopting a water-ethanol system, wherein the macroporous resin is AB-8 type macroporous resin, when performing gradient elution by adopting the water-ethanol system, the eluent is water, 25-35 v/v% ethanol aqueous solution, 65-75 v/v% ethanol aqueous solution and more than or equal to 90 v/v% ethanol aqueous solution respectively, collecting and combining the eluted part of the more than or equal to 90 v/v% ethanol aqueous solution for subsequent treatment;
(4) purifying the concentrated eluate by medium pressure preparative chromatography and/or high performance liquid chromatography to obtain the compound.
3. The method of claim 2, wherein the volume ratio of the solvent to pueraria lobata is 8-12: 1, the extraction condition is 55-65 ℃.
4. The method according to claim 2, wherein the volume ratio of n-butanol to water is 1:2 to 3.
5. The method according to claim 2, wherein the concentrated eluate is purified by: purifying the concentrated eluent by adopting medium-pressure preparative chromatography, performing gradient elution by taking methanol-water as a mobile phase, purifying the eluent by adopting high-performance preparative liquid chromatography, collecting and combining 75-85 v/v% methanol aqueous solution parts for subsequent treatment, wherein the filler of the medium-pressure preparative chromatography is octadecylsilane chemically bonded silica (C18), the 50-60 v/v% methanol aqueous solution, the 75-85 v/v% methanol aqueous solution and 100% methanol, the filler of the high-performance preparative liquid chromatography is octadecylsilane chemically bonded silica (C18), the eluent is 30-40 v/v% acetonitrile aqueous solution, and eluting at a constant speed at a flow rate of 50-70 ml/min.
6. The use of a compound according to claim 1 for the molluscicidal or molluscicidal manufacture of a medicament.
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Publication number Priority date Publication date Assignee Title
CN109251232B (en) * 2018-10-15 2021-03-09 上海诗丹德标准技术服务有限公司 New active ingredient of kudzuvine root and application thereof
CN109497098A (en) * 2018-12-19 2019-03-22 四川农业大学 A kind of bitter pueraria root extract that preventing and treating Pomacea canaliculata and niclosamidum kill spiral shell composition and application thereof

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Title
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