CN108084244A - A kind of triterpene saponin componds and its preparation method and application - Google Patents
A kind of triterpene saponin componds and its preparation method and application Download PDFInfo
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- CN108084244A CN108084244A CN201711475732.6A CN201711475732A CN108084244A CN 108084244 A CN108084244 A CN 108084244A CN 201711475732 A CN201711475732 A CN 201711475732A CN 108084244 A CN108084244 A CN 108084244A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
Abstract
The present invention relates to field of medicaments, more particularly to a kind of new triterpene saponin componds and its preparation method and application.The present invention provides a kind of compound, and the structural formula of the compound is shown in formula I.Compound provided by the present invention has the activity against snails of some strength, and the activity against snails of varying strength can be shown under different drug solubility.
Description
Technical field
The present invention relates to field of medicaments, more particularly to a kind of new triterpene saponin componds and preparation method thereof and use
On the way.
Background technology
Saponin (saponins) is also known as saponin, is the special glucoside of one kind for being widely present in plant kingdom, its aqueous solution
Lasting saponiform foam can be produced after shaking, thus is gained the name.Saponin is increasingly subject to people as a kind of bioactive substance
Concern.The structure of sapogenin is generated after being hydrolyzed according to saponin, triterpenoid saponin (triterpenoidal can be divided into
Saponins) with steroid saponin (steroidal saponins) two major classes.Triterpenoid saponin compound is a kind of basic parent nucleus
The compound being made of 30 or so carbon atoms is often present in a free form or in the form of being combined into glycosides or ester with sugar
In plant.
The content of the invention
In view of the foregoing deficiencies of prior art, it is an object of the invention to provide a kind of triterpene saponin componds,
For solving the problems of the prior art.
In order to achieve the above objects and other related objects, first aspect present invention provides a kind of compound, the compound
With good activity against snails.Compound provided by the present invention is typically triterpene saponin componds, structural formula such as Formulas I institute
Show：
Second aspect of the present invention provides the preparation method of the compound, including：The compound is extracted from omei mountain kudzuvine root.
In some embodiments of the invention, the preparation method includes：
(1) by omei mountain kudzuvine root alcohol extracting, extracting solution concentration；
(2) extracting solution after concentration is extracted, organic phase precipitation；
(3) precipitation products therefrom is passed through into resin adsorption, elution, eluent concentration；
(4) by the eluent after concentration to get the compound.
The omei mountain kudzuvine root is often referred to the root of plant hardship Pueraria lobota.Bitter Pueraria lobota (Pueraria peduncularis (Grah.ex
Btnth) Benth.) it is pulse family (Leguminosae) Pueraria lobota category (Pueraria) voluble herb plant also known as Yunnan kudzu, white hardship
Pueraria lobota and red bitter Pueraria lobota (Yunnan), are distributed mainly on the ground such as China Sichuan, Tibet, Guangxi, Guizhou and Yunnan, wherein with Yunnan distribution most
To be extensive.
Suitable solvent species and usage amount may be selected for alcohol extracting in those skilled in the art, so as to by object to be extracted
Soluble component in matter is fully dissolved out.
In some embodiments of the invention, solvent used in alcohol extracting can be alcohols solvent or their aqueous solution
Deng the alcohols solvent can be such as methanol, ethyl alcohol.Preferably, solvent used in alcohol extracting can be 70-85v/v%
Ethanol water.
In some embodiments of the invention, the volume ratio of solvent and omei mountain kudzuvine root is 8-12：1, the condition of extraction is room temperature
It it is specially 55-65 DEG C, extraction time is more than twice to the temperature of solvent refluxing.
In some embodiments of the invention, the extracting solution obtained by alcohol extracting also carries out separation of solid and liquid.
In some embodiments of the invention, the extracting solution after concentration is extracted using n-butanol and water, n-butanol
Volume ratio with water is 1:2~10, it is preferably 1:2~3.
In some embodiments of the invention, organic phase precipitation to medicinal extract.
In some embodiments of the invention, precipitation products therefrom is dissolved in water, is adsorbed by macroreticular resin, used
Water-ethanol system carries out gradient elution.
In some of the invention embodiments, the macroreticular resin is AB-8 type macroreticular resins, using water-ethanol system into
During row gradient elution, eluent is respectively water, 25-35v/v% ethanol waters, 65-75v/v% ethanol waters and >=90v/
V% ethyl alcohol ethanol waters collect merging >=90v/v% ethanol waters elution part and carry out subsequent processing.
In some embodiments of the invention, the eluent after concentration passes through middle compacting standby chromatography and/or high-efficient liquid phase color
Spectrum carries out purifying preparation.
In some embodiments of the invention, the specific method by the eluent after concentration is：By washing after concentration
De- liquid is suppressed standby chromatography and is purified in using, carry out gradient elution by mobile phase of methanol-water, eluent is again using efficiently system
Standby liquid chromatogram is purified.
In some embodiments of the invention, the filler that medium pressure prepares chromatography is octadecylsilane chemically bonded silica
(C18), eluent is respectively 50-60v/v% methanol aqueous solutions, 75-85v/v% methanol aqueous solutions and 100% methanol, collects and closes
And 75~85v/v% methanol aqueous solutions part carries out subsequent processing.
In some embodiments of the invention, the filler of the high performance preparative liquid chromatography is octadecylsilane bonded silica
Glue (C18), eluent at the uniform velocity elute for 30~40v/v% acetonitrile solutions, 50~70ml/min of flow velocity.
Third aspect present invention provides the compound in spiral shell or the purposes in preparing snail killing agent of going out.It is provided herein
Compound have some strength activity against snails, can be shown under different drug solubility varying strength go out spiral shell work
Property, the activity against snails, which are often referred to substance, can inhibit snail growth and/or cause the properties such as snail death, and the snail is specific
Can be such as Pomacea canaliculata (Pomacea canaliculata (Lamarck).
Inventor isolates a kind of new oleanane-type triterpene saponin compound from omei mountain kudzuvine root, by the root of bitter Pueraria lobota
Through slightly carrying, extraction, macroporous resin adsorption, medium pressure liquid chromatography and high performance preparative liquid chromatography are separating obtained repeatedly, and using 1D
With its structure of 2D-NMR technical appraisement, compound name is：3-O- β-D- glucopyranoses (1-2)-β-D- glucopyranoses (1-
2) [β-D- glucopyranoses (1-3)-beta d glucopyranosiduronic 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-
Glucuronopyranosyl] -12-oleanene-30-oic acid), structural formula is shown in formula I.
Description of the drawings
Fig. 1 is shown as the embodiment of the present invention1H-NMR spectrum(pridine-d5) result schematic diagram.
Fig. 2 is shown as the embodiment of the present invention13C-NMR spectrum(pridine-d5) result schematic diagram.
Fig. 3 is shown as 1H-1HCOSY spectrum of the embodiment of the present invention (pridine-d5) result schematic diagram.
Fig. 4 is shown as HSQC spectrum of the embodiment of the present invention (pridine-d5) result schematic diagram.
Fig. 5 is shown as HMBC spectrum of the embodiment of the present invention (pridine-d5) result schematic diagram.
Fig. 6 is shown as NOESY spectrum of the embodiment of the present invention (pridine-d5) result schematic diagram.
Fig. 7 is shown as Q-TOFspectrum result schematic diagrams of the embodiment of the present invention.
Fig. 8 is shown as the H-C accompanying drawings of HMBC of the embodiment of the present invention.
Fig. 9 is shown as the H-H accompanying drawings of NOESY of the embodiment of the present invention.
Specific embodiment
Illustrate embodiments of the present invention below by way of specific specific example, those skilled in the art can be by this specification
Disclosed content understands other advantages and effect of the present invention easily.The present invention can also pass through in addition different specific realities
The mode of applying is embodied or practiced, the various details in this specification can also be based on different viewpoints with application, without departing from
Various modifications or alterations are carried out under the spirit of the present invention.
It should be clear that in the following example not specifically dated process equipment or device using conventional equipment in the art or
Device.
In addition, it should also be understood that, one or more method and step mentioned in the present invention does not repel before and after the combination step
Other methods step can also be inserted into there may also be other methods step or between the step of these are specifically mentioned, unless separately
It is described；It should also be understood that the combination connection relation between one or more equipment/device mentioned in the present invention is not repelled
The front and rear two equipment/devices specifically mentioned there may also be other equipment/device or at these of the unit equipment/device it
Between can also be inserted into other equipment/device, unless otherwise indicated.Moreover, unless otherwise indicated, the number of various method steps is only
Differentiate the convenient tool of various method steps rather than the ordering for limitation various method steps or the enforceable model of the restriction present invention
It encloses, relativeness is altered or modified, and in the case where changing technology contents without essence, when being also considered as, the present invention is enforceable
Scope.
Embodiment 1
The preparation of compound：
(1) omei mountain kudzuvine root of crushing is weighed, the 70-85% ethyl alcohol of 8-12 times of volume is added in, stirs evenly, 60 DEG C of refluxing extractions are 2
It is secondary, every time 4 it is small when, filtering, merging filtrate is recovered under reduced pressure ethyl alcohol, it is spare to obtain 1.5kg liquids；
(2) by gained liquid n-butanol and the repeated multiple times extraction of water in step (1), n-butanol and water volume ratio are 1:
2, extract liquor is concentrated into medicinal extract, obtains n-butyl alcohol extract 800g；
(3) gained extract in step (2) with 10L moisture is dissipated, then carries out macroporous resin adsorption, big pore resin type
Number for AB-8, and gradient elution is carried out with water-ethanol, eluent is respectively water, 30v/v%, 70v/v% and 95v/v% ethyl alcohol
Aqueous solution is collected 95v/v% ethanol elutions parts and is merged, be recovered under reduced pressure 125g liquids are spare；
(4) by gained liquid in step (3), with medium pressure liguid chromatograph, (middle pressure C18, Suzhou Correspondent chromatographic separation and purification have
Limit company, filler are octadecylsilane chemically bonded silica (C18)) it is purified, carrying out gradient as mobile phase using methanol-water washes
De-, eluent is respectively 55v/v%, 80v/v% methanol aqueous solution and 100% methanol, and it is water-soluble to collect amalgamation liquid 80v/v% methanol
Liquid elution fraction, be recovered under reduced pressure 4g liquids are spare；
(5) by gained liquid in step (3), with high performance preparative liquid chromatography instrument, (Shimadzu LC-20AP series, filler are 18
Alkyl silane bonded silica gel (C18)) it is refined, eluant, eluent at the uniform velocity elutes for 35v/v% acetonitriles, and flow velocity 70ml/min is obtained
Purity is more than 98% target compound 116mg.
Structural Identification：
Compound is white powder, and Liebermann-Burchard reactions are in orange red, and Molish reactions are positive, therefore
The compound may be triterpene saponin componds.HR-ESI-MS m/z 1131.5232 [M-H]-, calculated value is
1131.5223, the molecular formula of compound is determined as C54H84O25 with reference to 1H- and 13C-NMR spectrums, calculates its degree of unsaturation as 11.
1H-NMR spectrums show 7 unimodal methyl：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), which are shown, alkene hydrogen in the compound, and is ethylene linkage (δ in ring>5).
CH2 δ 2.78 (1H, d, J=15.5Hz), δ 1.96 (1H, d, J=15.1Hz) and 28 methyl δ 1.19 in HMBC spectrums on 15
(3H, s) has long-range related to the quaternary carbon of δ 215.7, and in addition HMBC composes 29 methyl δ 1.44 (3H, s) and 180.9 quaternary carbons and has far
Cheng Xiangguan, so it is carbonyl to prompt the compound 16,30 are carboxyl.Therefore the compound aglycon parent nucleus is 12 olives
Alkene -30- formic acid.
1δ 4.99 (1H, d, J=7.6Hz), δ 5.29 (1H, d, J=7.7Hz), δ 5.63 (1H, d, J=in H-NMR spectrums
7.7Hz), four terminal hydrogens of δ 5.66 (1H, d, J=7.6Hz), δ 103.0, δ 104.8,104.8,105.0 4 during 13C-NMR is composed
A end group carbon shows that the compound is four glucosides.Totally 24 carbon signals of δ 105- δ 62.4 in 13C-NMR spectrums, in addition sugar in HMBC spectrums
On proton hydrogen δ 4.66 have to carboxyl carbon δ 172.6 long-range related, should have 1 glucuronic acid, further according to splitting point for terminal hydrogen
Situation and coupling constant (1H, d, J=7.6Hz), (1H, d, J=7.7Hz) may infer that this four sugared configurations are β-D- grapes
Sugar and glucuronic acid.Terminal hydrogen δ 4.99 has long-range related to H2 δ 4.32 in COSY spectrums, and δ 5.29 and H2 δ 4.08 have remotely
Correlation, δ 5.63 have long-range related to H2 δ 4.10, and δ 5.66 has long-range related, H2 δ 4.32 and C2 δ in hsqc spectrum to H2 δ 4.40
80.5, H3 δ 4.20 and C3 δ 87.3, H2 δ 4.08 and C2 δ 75.3, H2 δ 4.10 and C2 δ 76.2, H2 δ 4.40 and C2 δ 82.0 have
It is long-range related, H1 δ 4.99 and aglycon 3 hydrogen δ 3.20, H1 δ 5.29 and H3 δ 4.20 in NOESY spectrums, H1 δ 5.63 and H2 δ 4.40,
There are NOE, terminal hydrogen δ 4.99 and aglycon C-3 δ 89.2, terminal hydrogen δ 5.29 in HMBC spectrums between H1 δ 5.66 and H3 δ 4.32
With C3 87.3 on sugar, the terminal hydrogen δ 5.63 and upper C2 82.0 of sugar, terminal hydrogen δ 5.66 and sugar above C2 80.5 have it is long-range related,
So the sugar that four sugared connection modes are respectively terminal hydrogen δ 4.99 is connected with aglycon C-3 in a manner of 1-3, terminal hydrogen δ's 5.29
Sugar is connected with sugared C-3 of terminal hydrogen δ 4.99 in a manner of 1-3, sugared and terminal hydrogen δ 4.99 sugared C-2 of terminal hydrogen δ 5.66 with
1-2 modes are connected, and the sugar of terminal hydrogen δ 5.63 is connected with sugared C-2 of terminal hydrogen δ 5.66 in a manner of 1-2, therefore the connection of sugar chain
Order is 3-O- β-D- glucopyranose (1-2)-β-D- glucopyranoses (1-2) [β-D- glucopyranoses (1-3)-β-D- pyrroles
Glucopyranoside aldehydic acid].
It to sum up analyzes, the Structural Identification for determining compound KGC-32 is：3-O- β-D- glucopyranoses (1-2)-β-D- pyrroles
- 12 oleanene -30- formic acid of glucopyranoside (1-2) [β-D- glucopyranoses (1-3)-beta d glucopyranosiduronic acid].The change
1H-NMR the and 13C-NMR modal datas for closing object are shown in Table 1.
Table 1
Embodiment 2
The target compound that embodiment 1 is prepared carries out activity against snails experiment, and specific method is as follows：
The Pomacea canaliculata of a diameter of 0.5 ± 0.1cm of shell is gathered in Sichuan Province Guanghan He Xing towns in June, 2017, is put into 25 DEG C
Laboratory environment is for use to adapt to after being fed 5 days with water and cabbage under constant temperature, removes the Pomacea canaliculata die.
Object solution allocation：The object appropriate 10mg and 30mg is accurately weighed respectively, is dissolved with DMSO solution, respectively
It is configured to 10mg.L-1And 30mg.L-1Object solution, another set is not with plus the DMSO solution of object does negative control；
20 Pomacea canaliculatas is taken to be put into one piece of experimental plate for there are 6 holes, 2 holes add in 10mg.L-1Object solution, 2 holes add in
30mg.L-1Object solution, in addition 3 holes be put into not plus object negative control solution, observed respectively when 24 is small, 48
Hour and 72 it is small when after the death rate
Experimental result：10mg.L-1Object solution have after 72 hours 26.25% the death rate, 30mg.L-1Mesh
Mark object solution when 24 is small, 48 it is small when and 72 it is small when after the death rate be respectively 21.25%；57.5%, 71.25%.
Table 2
From the related data of table 2, noval chemical compound provided by the present invention has preferable activity against snails, drug solubility
For 30mgL-1Respectively when 24 is small, 48 it is small when and 72 it is small when the interior activity against snails for respectively showing varying strength.
In conclusion the present invention effectively overcomes various shortcoming of the prior art and has high industrial utilization.
The above-described embodiments merely illustrate the principles and effects of the present invention, and is not intended to limit the present invention.It is any ripe
Know the personage of this technology all can carry out modifications and changes under the spirit and scope without prejudice to the present invention to above-described embodiment.Cause
This, those of ordinary skill in the art is complete without departing from disclosed spirit and institute under technological thought such as
Into all equivalent modifications or change, should by the present invention claim be covered.
Claims (10)
1. a kind of compound, the structural formula of the compound is shown in formula I：
2. compound as described in claim 1, which is characterized in that the compound is triterpene saponin componds.
3. the preparation method of the compound as described in claim 1-2 any claims, including：From omei mountain kudzuvine root described in extraction
Compound.
4. preparation method as claimed in claim 3, which is characterized in that the preparation method includes：
(1) by omei mountain kudzuvine root alcohol extracting, extracting solution concentration；
(2) extracting solution after concentration is extracted, organic phase precipitation；
(3) precipitation products therefrom is passed through into resin adsorption, elution, eluent concentration；
(4) by the eluent after concentration to get the compound.
5. preparation method as claimed in claim 4, which is characterized in that solvent used in alcohol extracting for alcohols solvent or they
The volume ratio of aqueous solution, solvent and omei mountain kudzuvine root is 8-12：1, the condition of extraction is the temperature of room temperature to solvent refluxing, is specially 55
~65 DEG C.
6. preparation method as claimed in claim 4, which is characterized in that carried out using n-butanol and water to the extracting solution after concentration
The volume ratio of extraction, n-butanol and water is 1:2~10, it is preferably 1:2~3, organic phase precipitation to medicinal extract.
7. preparation method as claimed in claim 4, which is characterized in that precipitation products therefrom is dissolved in water, passes through macroreticular resin
It is adsorbed, gradient elution is carried out using water-ethanol system, the macroreticular resin is AB-8 type macroreticular resins, using water-ethanol
System carry out gradient elution when, eluent be respectively water, 25-35v/v% ethanol waters, 65-75v/v% ethanol waters and
>=90v/v% ethanol waters collect merging >=90v/v% ethanol waters elution part and carry out subsequent processing.
8. preparation method as claimed in claim 4, which is characterized in that eluent after concentration by the standby chromatography of middle compacting and/
Or high performance liquid chromatography carries out purifying preparation.
9. preparation method as claimed in claim 8, which is characterized in that the specific method by the eluent after concentration is：
Standby chromatography is suppressed during eluent after concentration is used to purify, and gradient elution, eluent are carried out by mobile phase of methanol-water
It is purified again using high performance preparative liquid chromatography, the filler that medium pressure prepares chromatography is octadecylsilane chemically bonded silica
(C18), 50-60v/v% methanol aqueous solutions, 75-85v/v% methanol aqueous solutions and 100% methanol are collected and merge 75~85v/
V% methanol aqueous solutions part carries out subsequent processing, and the filler of the high performance preparative liquid chromatography is octadecylsilane bonded silica
Glue (C18), eluent at the uniform velocity elute for 30~40v/v% acetonitrile solutions, 50~70ml/min of flow velocity.
10. compound as described in claim 1-2 any claims is in spiral shell or the purposes in preparing snail killing agent of going out.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109251232A (en) * | 2018-10-15 | 2019-01-22 | 上海诗丹德标准技术服务有限公司 | A kind of new bitter Pueraria lobota active constituent and its application |
| 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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| GB1277417A (en) * | 1968-06-21 | 1972-06-14 | Nat Res Dev | Improvements relating to molluscicides |
| CN104855382A (en) * | 2015-05-19 | 2015-08-26 | 四川农业大学 | Application of Pedunsaponin A and Pedunsaponin C in preparation of molluscacide |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1277417A (en) * | 1968-06-21 | 1972-06-14 | Nat Res Dev | Improvements relating to molluscicides |
| CN104855382A (en) * | 2015-05-19 | 2015-08-26 | 四川农业大学 | Application of Pedunsaponin A and Pedunsaponin C in preparation of molluscacide |
Non-Patent Citations (3)
| Title |
|---|
| CHUNPING YANG, MIN ZHANG, BO LEI, GUOSHU GONG AND HUABAO CHEN: "Active saponins from root of Pueraria peduncularis (Grah. ex Benth.) Benth. and their molluscicidal effects on Pomacea canaliculata", 《PEST MANAGEMENT SCIENCE》 * |
| KEN-ICHI NIHEI,BAI-PING YING,TAKANORI MURAKAMI,HIROKO MATSUDA,MA: "Pachyelasides A-D, Novel Molluscicidal Triterpene Saponins", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109251232A (en) * | 2018-10-15 | 2019-01-22 | 上海诗丹德标准技术服务有限公司 | A kind of new bitter Pueraria lobota active constituent and its application |
| 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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| CN108084244B (en) | 2020-06-16 |
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