CN105153264B - One kind drop Triterpene saponins compound and its preparation method and application - Google Patents
One kind drop Triterpene saponins compound and its preparation method and application Download PDFInfo
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- CN105153264B CN105153264B CN201510525628.8A CN201510525628A CN105153264B CN 105153264 B CN105153264 B CN 105153264B CN 201510525628 A CN201510525628 A CN 201510525628A CN 105153264 B CN105153264 B CN 105153264B
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Abstract
The present invention relates to one kind drop triterpene saponin compound and its production and use, belong to field of natural medicinal chemistry, it is characterized in that passing through the chemical method of water or organic solvent, extracting and developing, purifying from the extra large covering herb in North America, a kind of drop triterpenes noval chemical compound is obtained, extra large covering saponin(e fourth is named as.The compound can suppress growth of pathogenic bacteria in vitro, it was demonstrated that extra large covering saponin(e fourth has new application in antimycotic and bacterial drug is prepared.
Description
Technical field
The present invention relates to natural medicine field, and in particular to a kind of isolated new soap is extracted from Salicornia bigelovii
The application of glycosides, its preparation method, and the saponin(e in antimycotic and bacterial drug is prepared.
Background technology
Salicornia bigelovii, also known as than lucky Rockwell glasswort（Salicornia bigeloviiTorr.）, belong to Chenopodiaceae sea
Fluffy sub- category（SalicorniaL.）Plant, can directly use seawater irrigation.Cultivation glasswort is beneficial to improve ecological environment, builds
Ecological wetland, food and habitat are provided for wild birds.
Meanwhile, glasswort has a variety of comprehensive Utilization Ways, its seed oil content about 30%, and wherein unrighted acid contains
Amount up to 90%；In addition to containing amino acid needed by human, trace element, the carotene carotene content in glasswort exceedes common vegetable
40 times, can as green organic vegetable, health food, health-care oil etc. raw material.
Salicornia bigelovii is there is not yet pharmacological activity is reported, but it is belonged to together nearly source kind more medical value.Such as salicornia europaeal（S. europaea）With soothing the liver, diuresis, the effect being depressured, hypertension and headache are cured mainly, is also had for Vitamin C disease, diuresis and work
Blood dredging collateral；S. brachiataIt is used to treat mange and pruitus in India；In South Korea,S. herbaceaIt is used for treatment
Constipation, obesity, diabetes and cancer.
We to Salicornia bigelovii chemical composition and pharmacological activity by carrying out system research, to extend its application,
Especially excavate its application value.In to Salicornia bigelovii herb in the separation of saponin component, a new saponin(e is obtained
Compound, specify that the structure of the compound, bioactivity and purposes.
The content of the invention
An object of the present invention is to provide a kind of new drop Triterpene saponins compound and preparation method thereof and newization
Application of the compound in antimycotic and bacterial drug is prepared.According to the present invention, the noval chemical compound can be prepared into medicine, for agriculture
Crop and the preventing and treating of industrial crops fungi and bacteriosis.
The new drop Triterpene saponins compound of the present invention is obtained from extracting and developing, purifying in Salicornia bigelovii herb, is named
For glasswort saponin(e fourth.
Glasswort saponin(e fourth, chemical name is：3-O- beta d glucopyranosiduronic acids -30- removes first -12,20 (29)-diene
Oleanolic acid.
Chemical structural formula is：
Glasswort saponin(e fourth
The preparation method of above-mentioned glasswort saponin compound, it is characterised in that：Using Salicornia bigelovii herb as raw material, through water
Or after organic solvent or mixed solvent are extracted, aqueous extract directly crosses macroporous resin adsorption, organic solvent or mixed solvent are extracted
It is dissolved in water after liquid concentration again through macroporous resin adsorption or extracting n-butyl alcohol, macroporous resin adsorption thing or n-butyl alcohol extract are through post
Chromatography and obtain.Wherein, macroreticular resin includes D101, AB-8 or HP-20；Column chromatography silica gel, aluminum oxide, polyamide and
One or more in ODS；Organic solvent includes methanol, ethanol or n-butanol；Extracting temperature is less than 100 DEG C.
Pharmaceutical composition and its preparation are prepared into the invention provides glasswort saponin(e fourth and auxiliary material.Such as, aqua, wettable
Pulvis, water dispersible granules.
Antimycotic and anti-bacterial drug application is prepared the invention provides glasswort saponin compound.Antibacterial is real in vitro
Test middle glasswort saponin(e fourth can substantially suppress botrytis cinerea (Botrytis cinerea), rice banded sclerotial blight (Thanatephorus cucumeris) growth, EC5013.6 μ g/ml, 13.9 μ g/ml are respectively reached, show that glasswort saponin(e fourth has to phytopathogen
There is preferable inhibition, novel pesticide composition or lead compound with bactericidal action can be used as.
Glasswort saponin compound involved in the present invention not yet finds Patents or document report so far.
Advantages of the present invention and effect are from Salicornia bigelovii herb to utilize appropriate solvent, efficient extraction tool
There is the method for the compound for seeing phytopathogen effect.Glasswort saponin(e fourth is synthesized as plant source natural product with traditional chemical
Farm chemical ingredients are compared, with it is environment-friendly, to people and animals' low toxin.This application overcomes glasswort only as green simultaneously
Application limitation in terms of color organic vegetable.
4th, illustrate：
It can be reported using figure below as APPENDIX MATERIALSThe.
The molecular structural formula of Fig. 1 noval chemical compounds
HR-ESI (-)-MS spectrums of Fig. 2 noval chemical compounds
Fig. 3 noval chemical compounds1H-NMR is composed
Fig. 4 noval chemical compounds13C-NMR is composed
The COSY spectrums of Fig. 5 noval chemical compounds
The HMQC spectrums of Fig. 6 noval chemical compounds
The HMBC spectrums of Fig. 7 noval chemical compounds
The extraction separation of Fig. 8 noval chemical compounds
5th, embodiment：
With reference to embodiment, the invention will be further described, but present disclosure be not restricted to it is cited
Embodiment.The present invention is ordered from this saponins noval chemical compound that extracting and developing, purifying are obtained in Salicornia bigelovii herb
Entitled glasswort saponin(e fourth.
1. extract separation
Salicornia bigelovii herb is extracted and is concentrated to give medicinal extract by present inventor with 90% alcohol reflux, takes medicinal extract to use oil successively
Ether, ethyl acetate, extracting n-butyl alcohol.Obtain petroleum ether portion, ethyl acetate portion and n-butanol portion.
N-butanol portion is adsorbed with macroreticular resin, then is eluted with water-ethanol system segment, merges the group containing saponin(e
Point, obtain glasswort total saposins.Gained glasswort total saposins carry out silica gel column chromatography, and mobile phase is followed successively by chloroform-methanol（10 ︰ 1,
9 ︰ 1,5 ︰ 1,1 ︰ 1）, methanol.Wherein chloroform-methanol（7 ︰ 3）Part obtains monomer through anti-phase post separation repeatedly and gel column purifying
Compound glasswort saponin(e fourth.
2. Structural Identification
The unsetting powder of white（Methanol-water）, 224~227 DEG C of mp, TLC vanillic aldehydes-concentrated sulfuric acid test solution heats aobvious purplish red
Color, becomes blue after placement.Molish reacts and Liebermann-Burchard reacting positives.Water is insoluble in, chloroform, first is slightly soluble in
Alcohol, is soluble in water-methanol mixed solution.Information above points out the compound to be triterpene saponin componds.HR-ESI(-)-MS
Display molecular ion peak is 629.3261 [M-H]-, compose and speculate with reference to hydrogen spectrum and carbon, molecular formula C35H49O10, molecular weight 630.1H-
NMR（C5D5N, 500MHz）δ：0.77, 0.88, 1.26, 1.28（3H, s, 4 × CH3）, it is female that oleanolic acid saponin respectively drops
The signal of 4 methyl on core.In addition with the methine [δ of a Ge Lian oxygen functional groupH 4.17 (1H, dd, J=4.5,
11.6 Hz, H-3)], three alkene hydrogen [δH 4.77, 4.73 (1H each, both s like, H2-29), 5.43
(1H, br d like, H-12)], an aldehyde group [δH 9.73 (1H, s)]。δH122.7 and 144.2 two
H signal can belong to C-12 and C-13, and it is △ to show saponin nucleus12Oleanolic acid.In carbon spectrum display 35 C atoms of compound,
29 belong to drop oleanolic acid saponin parent nucleus, and 6 belong to monose.13C-NMR（C5D5N, 125MHz）δ：82.0（C-3）And
179.3 glucose end group carbon, display compound has a glucose substitution on C-3, and its link position and order can pass through
HMBC and COSY spectrum checkings, are shown in Table -1.Comprehensive each data authentication compound for 3-O- beta d glucopyranosiduronic acids -30- go first -
12,20 (29)-diene oleanolic acid.
The new saponin(e nuclear magnetic resonance data of table 1 (δ, ppm, 0=TMS, pyridine-d5)
Conventional pharmaceutical dosage form can be made as active constituents of medicine for novel compound of present invention, e.g., aqua, wettable
Pulvis, water dispersible granules etc..
3. In Vitro Bacteriostasis
Alternaria alternate, Alternaria solani, Botrytis cinerea are selected,
Colletotrichum gloesporioides, Fusarium graminearum, Fusarium verticillioide,
Thanatephorus cucumeris, Sclerotinia sclerotiorum8 kind plant source pathogenic strains, with amphotericin B
The antibacterial activity of the noval chemical compound glasswort saponin(e fourth prepared for positive drug, the test present invention, as a result shows：Glasswort
Saponin(e fourth has antibacterial activity, rightB. cinereaThe EC of bacterial strain50For 13.6 μ g/ml；It is rightT. cucumerisThe EC of bacterial strain50
For 13.9 μ g/ml.
Inhibitory action (EC of the compound of table 2 to plant source pathogenic strain50, μg/ml)
| Bacterial strain | Glasswort saponin(e fourth |
| A. alternate | 31.8 |
| A. solani | 23.3 |
| B. cinerea | 13.6 |
| C. gloeosporioides | 34.0 |
| F. graminearum | 28.8 |
| F. verticillioide | 19.4 |
| T. cucumeris | 13.9 |
| S. sclerotiorum | 36.3 |
With reference to embodiment, the invention will be further described, but present disclosure be not restricted to it is cited
Embodiment.
Embodiment 1
Salicornia bigelovii herb 30Kg, is extracted three times, 200 liters of consumption, 3 days every time with 90% alcohol reflux, and concentration merges
Into the concentrate without alcohol taste, total medicinal extract is obtained.Use petroleum ether, ethyl acetate, extracting n-butyl alcohol successively again.N-butyl alcohol extract is through post
3 grams of glasswort saponin(e fourth is obtained after chromatography.（See accompanying drawing 8）
Embodiment 2
Salicornia bigelovii herb 10Kg, with water heating extracting three times, water consumption is 20 liters, and extraction time is 1 hour, is extracted
Temperature is 70 DEG C, and extract solution is through macroreticular resin（D101, AB-8, HP-20 etc.）Absorption, with water, 70% second is used after 30% alcohol flushing
Alcohol is eluted, and 70% ethanol eluate is recovered under reduced pressure solvent and obtains saponin mixture.Mixture is again through column chromatography（Silica gel column chromatography：Chlorine
Imitation-carbinol system, RP-C18 column chromatographies：Water-methanol system）After separation, 0.8 gram of glasswort saponin(e fourth is obtained.
Embodiment 3
Salicornia bigelovii herb 10Kg, is extracted three times with methanol cold soaking, and methanol usage is 20 liters, and extraction time is 1 day, is carried
Liquid is taken through macroreticular resin（D101, AB-8, HP-20 etc.）Absorption.With water, 70% ethanol elution, 70% ethanol are used after 30% alcohol flushing
Eluent is recovered under reduced pressure solvent and obtains saponin mixture.Mixture is again through column chromatography（Silica gel column chromatography：Chloroform-methanol system, RP-
C18 column chromatographies：Water-methanol system）After separation, 0.9 gram of glasswort saponin(e fourth is respectively obtained.
Embodiment 4
Salicornia bigelovii herb 10Kg, is extracted three times, 100 liters of consumption with 80% alcohol heat reflux, and extraction time is 2 small
When, Extracting temperature is 85 DEG C, and extract solution is adsorbed through macroreticular resin D101, then with water, 15%, 75% ethanol elution, 75% ethanol elution
Liquid is recovered under reduced pressure solvent and obtains the g of glasswort total saposins 87.Gained glasswort total saposins carry out silica gel column chromatography, and mobile phase is followed successively by
Chloroform-methanol-water（17:3:0.2→4:1:0.1→7:3:0.5→3:3:0.5）, methanol；Wherein chloroform-methanol-water（7:3:
0.5）Carry out reverse phase silica gel C-18 column chromatographies repeatedly（Eluant, eluent is 75% ethanol-water solution）Separation and gel column Sephdex LH-
20 chromatographic purifyings（Eluant, eluent is 80% ethanol-water solution）0.8 gram of compound glasswort saponin(e fourth is obtained, purity is 95%（External standard
Method）.
Aqua of the embodiment 5 containing new saponin monomer of the invention
A certain amount of saponin compound is weighed, the Silwet 408 of certain mass fraction is added（5%）, xanthans
（0.1%）, white carbon（0.2%）、DSGX-055（0.1%）And water（Complement to 100%）, it is 5% to stir and active ingredient is made
Aqua.
Suspending agent of the embodiment 6 containing new saponin(e of the invention
A certain amount of saponin compound is weighed, the dispersant NN0 of certain mass fraction is added（2%）, dispersant D425
（1.5%）, Nongru-700 #（1%）, xanthans（0.1%）, white carbon（0.2%）, ethylene glycol（5%）And water（Complement to 100%）Mixing
Uniformly, by steps such as high speed shear, sand mill sand millings, the suspending agent that active ingredient is 20% is made.
Claims (4)
1. dropping Triterpene saponins compound, referred to as sea covering saponin(e fourth in a kind of extra large covering in North America, chemical name is：3-O-β-D-
Glucopyranosiduronic acid -30- removes first -12,20 (29)-diene oleanolic acid, and chemical structural formula is：
。
2. the preparation method of compound according to claim 1, it is characterised in that Salicornia bigelovii herb 10Kg, with water plus
Heat extract three times, water consumption be 20 liters, extraction time be 1 hour, Extracting temperature be 70 DEG C, extract solution through macroporous resin adsorption,
With water, 70% ethanol elution is used after 30% alcohol flushing, 70% ethanol eluate is recovered under reduced pressure solvent and obtains saponin mixture, mixture
Again after column chromatography, RP-C18 column chromatography for separation, glasswort saponin(e fourth is obtained；The macroreticular resin is D101, AB-8, HP-20；
The silica gel column chromatography separation mobile phase is chloroform-methanol；The RP-C18 column chromatography for separation mobile phase is water-methanol.
3. the preparation method of compound according to claim 1, it is characterised in that Salicornia bigelovii herb 10Kg, with 80%
Alcohol heat reflux is extracted three times, 100 liters of consumption, and extraction time is 2 hours, and Extracting temperature is 85 DEG C, and extract solution is through macroreticular resin
D101 is adsorbed, then with water, 15%, 75% ethanol elution, 75% ethanol eluate is recovered under reduced pressure solvent and obtains glasswort total saposins；Gained
Glasswort total saposins carry out silica gel column chromatography, and mobile phase is followed successively by chloroform-methanol-water, methanol, and gained eluent carries out repeatedly anti-
Phase silica gel C-18 column chromatography for separation, eluant, eluent is 75% ethanol-water solution, gel column Sephdex LH-20 chromatographic purifyings, elution
Agent is 80% ethanol-water solution, obtains compound glasswort saponin(e fourth；The silica gel column chromatography mobile phase chloroform-methanol-water according to
Secondary is 17:3:0.2、4:1:0.1、7:3:0.5、3:3:0.5；The silica gel column chromatography eluent refers to chloroform-methanol-water 7:3:
0.5 eluent.
4. the compound described in claim 1 is preparing the application of antibacterium and antifungal drug.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102295677A (en) * | 2011-05-25 | 2011-12-28 | 江苏省中国科学院植物研究所 | New nortriterpenoid saponin of Salicornia bigelovii Torr., preparation method and application thereof |
| CN102408464A (en) * | 2011-09-06 | 2012-04-11 | 江苏省中国科学院植物研究所 | Novel notriterpenoid saponin compound and preparation method and application thereof |
| CN103232518A (en) * | 2013-04-17 | 2013-08-07 | 江苏省中国科学院植物研究所 | New salicornia bigelovii torr nortriterpenoid saponin compound, preparation method and uses thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102295677A (en) * | 2011-05-25 | 2011-12-28 | 江苏省中国科学院植物研究所 | New nortriterpenoid saponin of Salicornia bigelovii Torr., preparation method and application thereof |
| CN102408464A (en) * | 2011-09-06 | 2012-04-11 | 江苏省中国科学院植物研究所 | Novel notriterpenoid saponin compound and preparation method and application thereof |
| CN103232518A (en) * | 2013-04-17 | 2013-08-07 | 江苏省中国科学院植物研究所 | New salicornia bigelovii torr nortriterpenoid saponin compound, preparation method and uses thereof |
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