CN105481932A - Triterpenoid saponins compound, and preparation method and uses thereof - Google Patents
Triterpenoid saponins compound, and preparation method and uses thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of medicines, and discloses a triterpenoid saponins compound, and a preparation method and uses thereof. The triterpenoid saponins compound is 6-O-beta-D-glucoside-dammara-22,(23)(Z)-ene-3beta,6alpha,12beta,20,25-pentol-20-furyl side chain, and the structure formula is shown in the specification. The chemical structure of the triterpenoid saponins compound is determined by employing mass spectrum and one-dimension and two-dimension nuclear magnetic resonance spectrum technologies and chemical methods. In-vitro antitumor activity tests show that the triterpenoid saponins compound possesses obvious antitumor activity and provides a new source for preparing antitumor medicines.
Description
Technical field
The invention belongs to medical art, particularly triterpene saponin componds and its production and use.
Background technology
Pseudo-ginseng Panaxnotoginseng is the dry root and rhizome of panax araliaceae plant, and another name mountain paint, invaluable, field paint, Typhonium flagelliforme (Lodd.) Blume, pseudo-ginseng, Radix Notoginseng, blood ginseng, Panax pseudoginseng, Yunnan pseudo-ginseng etc., main product is in the ground such as Yunnan Province of China, Guangxi.This product is warm in nature, sweet, the micro-hardship of taste, nontoxic.Pseudo-ginseng raw product energy swelling and pain relieving, loose stasis of blood hemostasis, ripe product can be enriched blood and be invigorated blood circulation.Pseudo-ginseng is used for the treatment of disease and has long history, is one of traditional rare medicinal herbs that China is conventional.For thousands of years for the prosperity of the Chinese nation has made huge contribution, and the dark concern by the people of the world and attention.
Nowadays modern science and technology develop rapidly, result in the research means backwardness relatively of traditional Chinese medicine theory, thus disconnects mutually with modern scientific theory, and the drug effect development of resources of pseudo-ginseng is comparatively limited to.Saponin(e, as the main pharmacodynamics material composition of pseudo-ginseng, is often difficult to directly be absorbed by the body with elementary saponin(e form, but will becomes secondary saponin especially rare ginsenoside through body metabolism, just can be rapidly absorbed into blood, play drug action.
Bio-transformation means have the advantages that reaction is very fast, specificity is comparatively strong, side reaction is less, make use of enzyme system complicated in microbe impels original chemical composition in pseudo-ginseng through the change of structural modification or avtive spot, obtain the lead compound that activity is better, toxicity is less, pharmaceutical use is larger, for new drug development, thus playing pseudo-ginseng resources advantage better, new drug exploitation to independent intellectual property right is provided with very important Research Significance and social benefit.
Pseudo-ginseng is as China's tradition rare traditional Chinese medicine, the same as early stage medicinal and edible plant with ginseng, have the good reputation of " king in ginseng ".There is multiple effective substance composition and stronger pharmacological action, be widely deployed into the treatment of multiple product for clinical disease.But meanwhile, pseudo-ginseng is as a kind of traditional herbal medicine, and wherein the purposes of Multiple components is not all exploited.Arasaponin is its main activeconstituents, but according to ginsenoside metabolic rule in vivo and structure activity relationship known, " ginsenoside " by after gastrointestinal absorption by entero-bacte step by step metabolism be secondary saponin and aglycon absorb enter blood circulation after play pharmacological action, show, natural ginseng saponin(e structure is not structure optimum regime.In sum, how by rational structural modification means, ginsenoside higher for content original in pseudo-ginseng is carried out the rare ginsenoside that structural modification changes into low sugar chain or new side-chain structure and become those skilled in the art's problem demanding prompt solution.
Summary of the invention
The present invention, for solving the problem, provides triterpene saponin componds and its production and use.
Primary and foremost purpose of the present invention is to provide a kind of new triterpene saponin componds.
Another object of the present invention is to provide above-mentioned triterpene saponin componds as the purposes preparing antitumor drug.
Another object of the present invention solves problem existing in prior art, provides a kind of preparation method of above-mentioned triterpene saponin componds.
For solving the problem, the present invention takes following technical scheme:
A kind of structural formula of triterpene saponin componds is:
Described triterpene saponin componds is: 6-O-β-D-Glucose glycosides-Da Ma-22, (23) (Z)-alkene-3 β, 6 α, 12 β, 20,25-pentol-20-furan nucleus side chain.
Above-mentioned triterpene saponin componds extracts and obtains from pseudo-ginseng converted product.
The preparation method of above-mentioned triterpene saponin componds, concrete steps are as follows:
Step one: the preparation of pseudo-ginseng converted product:
Prepared by A seed liquor:
Get glossy ganoderma seed culture fluid liquid culture based in pressure steam sterilizer in 121 DEG C of sterilising treatment 30 minutes, in aseptic operating platform, access slant strains after cooling, in 27 ~ 29 DEG C in constant-temperature shaking incubator, cultivate under 160 revs/min, asterism shape bacterium ball must be clarified, obtain seed liquor for subsequent use;
The preparation of B converted product:
Get pseudo-ginseng powder, add calcium carbonate somatomedin and water, mixing, sealing also sterilizing, cool under room temperature, access described seed liquor prepared by described steps A in aseptic operating platform, lucifuge is cultivated, to container bottom is covered with mycelium, takes out dry, obtain pseudo-ginseng converted product;
Step 2: extract:
Get described pseudo-ginseng converted product prepared by described step B, add the ethanol of 70% of 4 ~ 8 times of weight parts, refluxing extraction 3-5 time, each 1 ~ 3 hour, filter and united extraction liquid, compress to obtain thick paste; Described thick paste added water-dispersion and use sherwood oil, ethyl acetate, water-saturated n-butanol solution extraction 6 ~ 8 times successively, rear to extraction liquid drying under reduced pressure respectively, obtain sherwood oil part, ethyl acetate portion and water-saturated n-butanol part;
Step 3: separation and purification:
Get silica gel column chromatography on described ethyl acetate portion prepared by described step 2, with the methylene chloride-methanol mixed solvent wash-out of volume ratio 100:0-0:100, thin-layer chromatography inspection is known, collect the elutriant of methylene chloride-methanol 100:10 part, merging containing described triterpene saponin componds flow point is the elutriant of 179 ~ 194, recycling design is to dry, the open post of upper anti-phase ODS filler carries out pillar layer separation, use methanol-water gradient elution, the weight ratio of described methyl alcohol and water is respectively: 100:0, 70:30, 50:50, 30:70, 0:100, get the elution fraction that methanol-water is weight ratio 70:30, after decompression and solvent recovery, separation and purification is carried out through semi-preparative liquid phase, with 70% methanol-water wash-out, obtain described triterpene saponin componds sterling.
Further, described glossy ganoderma seed culture fluid liquid nutrient medium comprises the component of following weight percentage: glucose is 1% ~ 4%, and peptone is 0.2% ~ 1%, yeast powder is 0.1% ~ 0.3%, potassium primary phosphate is 0.1% ~ 0.3%, and magnesium sulfate is 0.1%, and water is 95% ~ 99%.
Further, described glossy ganoderma seed culture fluid liquid nutrient medium comprises the component of following weight percentage: glucose is 2%, and peptone is 0.5%, and yeast powder is 0.2%, and potassium primary phosphate is 0.1%, and magnesium sulfate is 0.1%, and water is 97.1%.
Further, in described step B: described pseudo-ginseng powder crosses 10 mesh sieves; The weight of the described calcium carbonate somatomedin added is 0.01 times amount of described pseudo-ginseng powder weight, and amount of water is 1.5 times of described pseudo-ginseng powder weight; In described pseudo-ginseng powder after being mixed, water content is 60%.
Further, in described step B: sterilising conditions is: sterilising treatment 1 hour in vertical pressure steam sterilizer; Lucifuge culture condition is: 29 ~ 31 DEG C, 65%RH.
Further, in described steps A, the weight ratio of seed liquor and pseudo-ginseng is: 2:1.
The purposes of above-mentioned triterpene compound, described triterpene saponin componds is preparing the application in novel anti-tumor medicine.
A kind of antitumor drug, comprises above-mentioned triterpene saponin componds.
Beneficial effect of the present invention is:
(1) a kind of new triterpene saponin componds is provided; Play pseudo-ginseng resources advantage better, new drug exploitation to independent intellectual property right is provided with very important Research Significance and social benefit.
(2) use anti tumor activity in vitro screening system to carry out activity rating to this new triterpene saponin componds, result shows, described compound has good antitumor action.Through anti tumor activity in vitro test, showing that there is obvious anti-tumor activity, providing new source for preparing antitumor drug.
Accompanying drawing explanation
Fig. 1 is triterpene saponin componds of the present invention
1h-NMR spectrogram;
Fig. 2 is triterpene saponin componds of the present invention
13c-NMR spectrogram;
Fig. 3 is the HMQC spectrogram of triterpene saponin componds of the present invention;
Fig. 4 is the HMBC spectrogram of triterpene saponin componds of the present invention;
Fig. 5 is the GC color atlas (D-Glu) of triterpene saponin componds of the present invention;
Fig. 6 is the GC color atlas (Sample) of triterpene saponin componds of the present invention.
Embodiment
Hereafter will describe content of the present invention in conjunction with specific embodiments in detail.It should be noted that the combination of technical characteristic or the technical characteristic described in following embodiment should not be considered to isolated, they can mutually be combined thus be reached better technique effect.
Embodiment 1:
One, a kind of triterpene saponin componds structural formula that the present invention relates to is as follows:
Its chemical name is: 6-O-β-D-Glucose glycosides-Da Ma-22, (23) (Z)-alkene-3 β, 6 α, 12 β, 20,25-pentol-20-furan nucleus side chain.Triterpene saponin componds of the present invention is from pseudo-ginseng converted product, be separated the new compound obtained first, called after pseudo-ginsenoside RT
7.
Triterpene saponin componds physicochemical constant of the present invention is as follows:
White powder (methyl alcohol), ESI-MS:m/z675.40 ([M+Na]
+), m/z687.38 ([M+Cl]
–), compose in conjunction with hydrogen spectrum and carbon and infer that its molecular formula is C
36h
60o
10.10% ethanol solution of sulfuric acid displaing amaranth, Molish reacting positive, Liebermann-Burchard reacting positive.
1h and
13c-NMR data are in table 1.
Table 1 compound
1h-NMR,
13c-NMR attribution data information
Through anti tumor activity in vitro test, compound significantly can suppress the amplification of human cervical carcinoma cell, and presents dose-dependence, shows to have obvious anti-tumor activity.Therefore, can be used for preparing new antitumor drug.
Two, triterpene saponin componds of the present invention is prepared:
Step one: the preparation of pseudo-ginseng converted product
The preparation of A seed liquor
The component that preferred nutritional type substratum comprises following weight percentage is grown: glucose 2% according to microbial bacterial, peptone 0.5%, yeast powder 0.2%, potassium primary phosphate 0.1%, magnesium sulfate 0.1%, pH natural condition preparation glossy ganoderma seed liquor liquid nutrient medium.Every 100ml liquid nutrient medium is sub-packed in 250ml inverted triangle bottle, and wrapping is placed in pressure steam sterilizer in 121 DEG C of sterilising treatment 30 minutes.After taking out cooling, in aseptic operating platform, access the slant strains kept.The liquid nutrient medium being connected to slant strains is put in 27 ~ 29 DEG C in constant-temperature shaking incubator, under 160 revs/min, is cultured in container that to be full of a large amount of clarification asterism shape bacterium ball for subsequent use.
The preparation of B converted product
Get dry pseudo-ginseng, appropriateness is pulverized, and cross 10 mesh sieves, obtain pseudo-ginseng powder, add calcium carbonate somatomedin according to the ratio of medicinal material somatomedin S/S, add suitable quantity of water and mix, amount of water is 1.5 times of described pseudo-ginseng powder weight; Water content in mixed pseudo-ginseng powder is made to reach 60%.Getting the every 50g of mixed pseudo-ginseng powder is sub-packed in the inverted triangle bottle of 500ml, and wiping bottleneck, seals bottleneck with tampon, with kraft paper wrapping, and marked with date, operator.Be placed in vertical pressure steam sterilizer sterilising treatment 1 hour.After end subject to sterilization, cool, in aseptic operating platform, access seed liquor under room temperature, in 29 ~ 31 DEG C, under 65%RH condition, lucifuge is cultivated, and to container bottom is covered with mycelium, takes out dry, obtains pseudo-ginseng converted product.
Step 2: extract
Get pseudo-ginseng converted product dry product 5.0kg, the alcohol heating reflux adding 4 ~ 8 times amount 70% extracts 3-5 time, each 1 ~ 3 hour, and filter, united extraction liquid, concentrating under reduced pressure obtains thick paste.Thick paste suitable quantity of water suspendible is disperseed, respectively extract 6 ~ 8 times with isopyknic sherwood oil, ethyl acetate, water-saturated n-butanol solution successively, preferably extract 6 times, extraction liquid respectively drying under reduced pressure obtains sherwood oil part 14g, ethyl acetate portion 50g, water-saturated n-butanol part 400g.
Step 3: separation and purification
Get silica gel column chromatography on described ethyl acetate portion prepared by described step 2, with the methylene chloride-methanol mixed solvent wash-out of volume ratio 100:0 ~ 0:100, thin-layer chromatography inspection is known, collect methylene chloride-methanol 100:10 elution fractions, merge the elutriant containing flow point 179 ~ 194 described in described triterpene saponin componds, recycling design is to dry, the open post of upper anti-phase ODS filler carries out pillar layer separation, with methanol-water (100:0 ~ 70:30 ~ 50:50 ~ 30:70 ~ 0:100) gradient elution, get 70% methanol-water elution fraction, after decompression and solvent recovery, separation and purification is carried out through semi-preparative liquid phase, with 70% methanol-water wash-out, obtain described triterpene saponin componds sterling 1.8mg.
Gained new compound physicochemical constant is as follows:
White powder (methyl alcohol), ESI-MS:m/z675.40 ([M+Na]
+), m/z687.38 ([M+Cl]
–), compose in conjunction with hydrogen spectrum and carbon and infer that its molecular formula is C
36h
60o
10.10% ethanol solution of sulfuric acid displaing amaranth, Molish reacting positive, Liebermann-Burchard reacting positive.
D identifies: adopt chemical process, the method such as gas chromatographic analysis and Wave Spectrum carries out Structural Identification.
1.0mol/L hydrochloric acid hydrolysis, adds Cys methyl esters hydrochloric acid and 1-TMS-1H-imidazoles obtains glucose-derivative, and after n-hexane extraction, adopt GC stratographic analysis, result is known as shown in Figure 5 and Figure 6, detects β-D-Glucose.
Known as shown in Figure 1, according to
1h-NMR (CD
3oD, 500MHz) high field region provides 7 methyl singlets signals, provides a sugared anomeric proton signal.
Known as shown in Figure 2, according to
13c-NMR (CD
3oD, 125MHz) spectrum in provide 36 carbon atom signals, high field region provides 7 methyl singlets signals, and low place provides a pair olefin signal and a carbonyl carbon signals, and middle place provides one group of glucose signals.
Known as shown in Figure 3 and Figure 4, compose known a part glucose by the HMQC spectrum and HMBC of resolving compound and become glycosides with C-6 position, provide the side chain annexation of compound simultaneously.
Compound
1h-NMR,
13c-NMR attribution data sees the above table shown in 1.
Embodiment 2: the compounds of this invention anti-tumor activity test
One, test materials
1, in vitro tests knurl strain:
Helas human cervical carcinoma cell, is provided by research and development centre of Changchun University of Traditional Chinese Medicine pharmacological evaluation room.
2, in vitro tests reagent:
New-born calf serum, DMSO (DMSO) and MTT tetra-salt (Sigma company).
3, in vitro tests instrument:
Microplate reader: MultiskanAscent, model: VL.23354-00541T.
Two, test method
The preparation of MTT liquid: get 250mgMTT, puts into small beaker, adds 50m1PBS (pH7.4,0.01M), and stir 30min, being mixed with concentration is 5mg/ml solution, with the millipore filter bacteriological filtration of 0.22um, packing, 4 DEG C of preservations, in two weeks effectively.
The tumour cell of taking the logarithm vegetative period, adds appropriate 0.25% trypsinase, attached cell is come off, does cell counting, and general non-staining viable cell more than 97%, should be made into 6 × 10
4/ ml cell suspension.Get 96 holes dull and stereotyped, every hole adds cell suspension 100u1, flat board is put 37 DEG C of 5%CO
2incubator 24h.After hatching 24h, add the testing compound solution of 100ul/ hole different concns in 96 orifice plates.Add 20ulMTT liquid in the 96 every holes of orifice plate, continue to hatch 4h, stop cultivating.Careful Aspirate supernatant, every hole adds 150u1DMSO solution, and concussion is dissolved, and measures the optical density value of each aperture with automatization spectrophotometric plate reader at 570nm place.
Test-results shows, the triterpene saponin componds that the present invention extracts, i.e. pseudo-ginsenoside RT
7to Helas human cervical carcinoma cell, there is certain lethal effect, the results are shown in Table shown in 2.
Table 2 pseudo-ginsenoside RT
7on the impact of Helas human cervical carcinoma cell.
The invention provides a kind of new triterpene saponin componds; The preparation method of triterpene saponin componds and purposes, and use anti tumor activity in vitro system of screening to carry out activity rating to this new triterpene saponin componds, result shows, described compound has good antitumor action.Through anti tumor activity in vitro test, showing that there is obvious anti-tumor activity, providing new source for preparing antitumor drug.
Although give some embodiments of the present invention, it will be understood by those of skill in the art that without departing from the spirit of the invention herein, can change embodiment herein.Above-described embodiment is exemplary, should using embodiment herein as the restriction of interest field of the present invention.
Claims (10)
1. triterpene saponin componds, is characterized in that, the structural formula of described triterpene saponin componds is:
Described triterpene saponin componds is: 6-O-β-D-Glucose glycosides-Da Ma-22, (23) (Z)-alkene-3 β, 6 α, 12 β, 20,25-pentol-20-furan nucleus side chain.
2. triterpene saponin componds as claimed in claim 1, it is characterized in that, described triterpene saponin componds extracts and obtains from pseudo-ginseng converted product.
3. a preparation method for triterpene saponin componds as claimed in claim 1, is characterized in that, concrete steps are as follows:
Step one: the preparation of pseudo-ginseng converted product:
Prepared by A seed liquor:
Get glossy ganoderma seed culture fluid liquid culture based in pressure steam sterilizer in 121 DEG C of sterilising treatment 30 minutes, in aseptic operating platform, access slant strains after cooling, in 27 ~ 29 DEG C in constant-temperature shaking incubator, cultivate under 160 revs/min, asterism shape bacterium ball must be clarified, obtain seed liquor for subsequent use;
The preparation of B converted product:
Get pseudo-ginseng powder, add calcium carbonate somatomedin and water, mixing, sealing also sterilizing, cool under room temperature, access described seed liquor prepared by described steps A in aseptic operating platform, lucifuge is cultivated, to container bottom is covered with mycelium, takes out dry, obtain pseudo-ginseng converted product;
Step 2: extract:
Get described pseudo-ginseng converted product prepared by described step B, add the ethanol of 70% of 4 ~ 8 times of weight parts, refluxing extraction 3-5 time, each 1 ~ 3 hour, filter and united extraction liquid, compress to obtain thick paste; Described thick paste added water-dispersion and use sherwood oil, ethyl acetate, water-saturated n-butanol solution extraction 6 ~ 8 times successively, rear to extraction liquid drying under reduced pressure respectively, obtain sherwood oil part, ethyl acetate portion and water-saturated n-butanol part;
Step 3: separation and purification:
Get silica gel column chromatography on described ethyl acetate portion prepared by described step 2, with the methylene chloride-methanol mixed solvent wash-out of volume ratio 100:0-0:100, thin-layer chromatography inspection is known, collect the elutriant of methylene chloride-methanol 100:10 part, merging containing described triterpene saponin componds flow point is the elutriant of 179 ~ 194, recycling design is to dry, the open post of upper anti-phase ODS filler carries out pillar layer separation, use methanol-water gradient elution, the weight ratio of described methyl alcohol and water is respectively: 100:0, 70:30, 50:50, 30:70, 0:100, get the elution fraction that methanol-water is weight ratio 70:30, after decompression and solvent recovery, separation and purification is carried out through semi-preparative liquid phase, with 70% methanol-water wash-out, obtain described triterpene saponin componds sterling.
4. the preparation method of triterpene saponin componds as claimed in claim 3, it is characterized in that, described glossy ganoderma seed culture fluid liquid nutrient medium comprises the component of following weight percentage: glucose is 1% ~ 4%, peptone is 0.2% ~ 1%, yeast powder is 0.1% ~ 0.3%, potassium primary phosphate is 0.1% ~ 0.3%, and magnesium sulfate is 0.1%, and water is 95% ~ 99%.
5. the preparation method of triterpene saponin componds as claimed in claim 4, it is characterized in that, described glossy ganoderma seed culture fluid liquid nutrient medium comprises the component of following weight percentage: glucose is 2%, peptone is 0.5%, yeast powder is 0.2%, potassium primary phosphate is 0.1%, and magnesium sulfate is 0.1%, and water is 97.1%.
6. the preparation method of triterpene saponin componds as claimed in claim 5, is characterized in that, in described step B: described pseudo-ginseng powder crosses 10 mesh sieves; The weight of the described calcium carbonate somatomedin added is 0.01 times amount of described pseudo-ginseng powder weight, and amount of water is 1.5 times of described pseudo-ginseng powder weight; In described pseudo-ginseng powder after being mixed, water content is 60%.
7. the preparation method of triterpene saponin componds as claimed in claim 6, is characterized in that, in described step B: sterilising conditions is: sterilising treatment 1 hour in vertical pressure steam sterilizer; Lucifuge culture condition is: 29 ~ 31 DEG C, 65%RH.
8. the preparation method of triterpene saponin componds as claimed in claim 7, it is characterized in that, in described steps A, the weight ratio of seed liquor and pseudo-ginseng is: 2:1.
9. the purposes of triterpene compound as claimed in claim 1, it is characterized in that, described triterpene saponin componds is preparing the application in novel anti-tumor medicine.
10. an antitumor drug, is characterized in that, comprises triterpene saponin componds according to claim 1.
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| CN109468359A (en) * | 2018-12-04 | 2019-03-15 | 长春中医药大学 | A kind of ginsenoside Rk6Preparation method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109234347A (en) * | 2018-09-30 | 2019-01-18 | 长春中医药大学 | A method of conversion protopanaxatriol type saponin(e generates C25-OH derivative |
| CN109234347B (en) * | 2018-09-30 | 2022-03-01 | 长春中医药大学 | Method for converting protopanaxatriol saponin to obtain C25-OH derivative |
| CN109468359A (en) * | 2018-12-04 | 2019-03-15 | 长春中医药大学 | A kind of ginsenoside Rk6Preparation method |
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