CN101440118B - Saponin compound extracted from Momordica grosvenori root, preparation and use thereof - Google Patents
Saponin compound extracted from Momordica grosvenori root, preparation and use thereof Download PDFInfo
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- JEAWWYBLYVPLRF-KRJVYMNUSA-N C[C@H](CC/C=C(\C)/C(O[C@@H](C(C1O)O)OC(CO[C@@H](C(C2O)O)OC(CO)[C@H]2O)[C@H]1O)=O)C(CC1)[C@@](C)(C2)[C@]1(C)[C@](C)(CCC(C1CC3)=C(C)C3=O)[C@@H]1C2=O Chemical compound C[C@H](CC/C=C(\C)/C(O[C@@H](C(C1O)O)OC(CO[C@@H](C(C2O)O)OC(CO)[C@H]2O)[C@H]1O)=O)C(CC1)[C@@](C)(C2)[C@]1(C)[C@](C)(CCC(C1CC3)=C(C)C3=O)[C@@H]1C2=O JEAWWYBLYVPLRF-KRJVYMNUSA-N 0.000 description 1
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Abstract
The invention relates to the medicine technical field, in particular to saponin compounds of Siraitic acid IIB and Siraitic acid IIC which are extracted and separated from fructus momordicae roots, a method for preparing the same and application thereof in an anti-tumor medicine. The molecular formulas of the two compounds are C40H60O14 and C41H62O15 respectively. By various modern spectral analysis, particularly the application of advanced two-dimensional nuclear magnetic resonance spectrum to comprehensive analysis, the chemical structures of the two compounds are determined. In vitro anti-tumor tests show that the compound Siraitic acid IIB can obviously inhibit lung cancer cells A549 and liver cancer cells Hep-G2, and the compound Siraitic acid IIC can also obviously inhibit liver cancer cells Hep-G2. The invention provides lead compound for research on a new anti-tumor medicine, and has essential values in comprehensively developing and utilizing fructus momordicae resources.
Description
(1) technical field:
The present invention relates to medical technical field, be specifically related to from Momordica grosvenori root, separate the saponins compound that obtains novel structure; The invention still further relates to the preparation method and its usage of above-mentioned saponins compound.
(2) background technology:
Grosvenor Momordica Siraitia grosvenrii (Swingle) C.Jeffrey is the distinctive economy of China, medicinal plant for the Curcurbitaceae Grosvenor Momordica belongs to the vine of perennial perennial root stem, is backlands district, osmanthus, Guangxi tradition special product.The prosperity of Grosvenor Momordica root system, the piece root manure is big, bitter, cold nature has clearing heat and expelling damp, the effect of removing obstruction in channels to relieve pain.Show that through pharmacological evaluation the extract of Momordica grosvenori root has anti-inflammatory, eases pain, separates stem, falls multiple effects such as enzyme, clinical trial proves that it is evident in efficacy to rheumatic arthritis.Extract to Momordica grosvenori root carries out antitumor screening, finds that it all shows stronger antitumour activity to the kinds of tumors spectrum in vivo and in vitro.
Forefathers mainly contain the The Chemical Constituents that Momordica grosvenori root has carried out:
1, the people such as Wang Xuefen of Guangxi Chinese materia medica institute are at first from the fat-soluble position of Momordica grosvenori root, separation has also been identified 2 triterpenic acids (see and rolled up the 515th～518 page of the 9th phase " herbal medicine " in 1996 the 27th), through spectroscopic identification and the structural analysis of X-diffraction crystal, find that they are for losing the cucurbitane type tetracyclic triterpene acid of carbon, difference called after arhat tartaric acid first (Siraitic acid A), arhat tartaric acid second (Siraitic acid B); Afterwards again isolation identification arhat tartaric acid third (Siraitic acid C), arhat tartaric acid fourth (Siraitic acid D) (seeing 1998 the 29th volumes the 5th phase " herbal medicine " the 293rd～295 page).
2, this of Chinese medical courses in general institute Institute of Medical Plants built bravely, people such as Chen Dihua also carries separating the thing from Momordica grosvenori root and obtain these compositions, and obtain a new triterpenic acid in addition, called after arhat tartaric acid penta (Siraitic acid E), also obtain some principal component be that a-tripalmitin (a-monopalmiten), a-spinasterol (spinasterol) and stearic acid (stearic acid) (are seen Acta Pharmaceutica Sinica Acta Pharmaceutica Sinica 1999,34 (12): 918～920).
So far the report of the chemical ingredients at fat-soluble position is not seen the report that has its water-solubility saponin compounds in rarely seen Momordica grosvenori root.
(3) summary of the invention:
The technical problem to be solved in the present invention is: the water-solubility saponin compounds Siraitic acid IIB and the Siraitic acid IIC of the novel structure that extraction separation obtains from Momordica grosvenori root are provided, and the preparation method and its usage of these two kinds of saponins compounds is provided.
The saponins compound of the present invention's novel structure of extraction separation from Momordica grosvenori root, specifically there are two kinds, difference called after Siraitic acid IIB (arhat tartaric acid second glycosides II) and Siraitic acid IIC (the arhat tartaric acid third glycosides II), wherein, the structural formula of Siraitic acid IIB is as shown in the formula shown in (I):
The structural formula of Siraitic acid IIC is as shown in the formula shown in (II):
The present invention also will provide the preparation method of above-mentioned saponins compound, and it may further comprise the steps:
(1) extracts: get the Momordica grosvenori root fragment with methyl alcohol or ethanolic soln heating and refluxing extraction, extracting solution reclaims methyl alcohol or ethanol, the medicinal extract that obtains is dissolved in the distilled water, filter, solution is by macroporous resin column, and water, 50% methyl alcohol and 100% methanol-eluted fractions are collected 100% meoh eluate successively, reclaim methyl alcohol, get total saponin extracts;
(2) separate: above-mentioned total saponin extracts applying silicon plastic column chromatography, with chloroform: methyl alcohol: the mixed solvent gradient elution of the volume ratio of water=20: 1: 0.1～5: 1: 0.1, thin-layer chromatography detects, and collects the stream part that contains Siraitic acid IIB and Siraitic acid IIC; Through dextrane gel Sephadex LH-20 chromatography, carry out wash-out with 100% methyl alcohol again, thin-layer chromatography detects, and collects the stream part that contains target compound; After C
18Reversed phase column chromatography, with methyl alcohol: the mixed solvent of the volume ratio of water=1: 4～4: 2 carries out wash-out, and thin-layer chromatography detects, and obtains Siraitic acid IIB and Siraiticacid IIC.
In above-mentioned preparation method's step (1), the Momordica grosvenori root fragment is 80～100% methyl alcohol or ethanolic soln heating and refluxing extraction with being equivalent to 4～6 times of its weight, volumetric concentration; The number of times that extracts is 2～3 times, and each time of extracting is 2～4 hours, preferably extracts 3 times, extracts 2～3 hours at every turn; Described macroporous adsorptive resins can be D101 type, AB-8 type or Diaion HP20 type.
For the Momordica grosvenori root fragment generally is that Momordica grosvenori root is crushed to 10～40 orders.
The present invention also comprises: saponins compound Siraiticacid IIB that extraction separation obtains from Momordica grosvenori root and the Siraitic acid IIC purposes in the preparation antitumor drug.
The present invention separates saponins compound Siraitic acid IIB and the Siraitic acid IIC that obtains two kinds of novel structures from the methyl alcohol of Momordica grosvenori root or ethanol extraction, the applicant after deliberation, finding these two kinds of compounds, external strain has the obvious suppression effect to multiple Zhong , provide lead compound for developing new antitumor drug, comprehensive development and utilization Grosvenor Momordica resource has been had important value.
(4) embodiment:
Embodiment 1:
Getting Momordica grosvenori root fragment (30 order) 3000 grams that exsiccant is collected in Longjiang township, Yongfu, Guilin, to be soaked in 15 liters of volumetric concentrations be in 80% the methyl alcohol, 80 ℃ of refluxing extraction 3 times, and each 3 hours, filter, united extraction liquid, reclaim under reduced pressure methyl alcohol get medicinal extract 120 grams.Medicinal extract is dissolved in 2 liters of distilled water, filter, filtrate is by D101 type macroporous resin column, water successively, volumetric concentration is 50% methyl alcohol, volumetric concentration is 100% methyl alcohol gradient elution, collect 100% meoh eluate, reclaim under reduced pressure methyl alcohol gets medicinal extract 5.1 grams, uses silica gel column chromatography then, with chloroform: methyl alcohol: water=20: 1: 0.1～5: 1: 0.1 (v/v) mixed solvent gradient elution, thin-layer chromatography detects, and collects the stream part that contains Siraitic acid IIB and Siraitic acid IIC, again through dextrane gel Sephadex LH-20 chromatography, with volumetric concentration is that 100% methyl alcohol carries out wash-out, thin-layer chromatography detects, and collects the part that contains target compound, through C
18Reversed-phase column separates, with methyl alcohol: water=3: 2 (v/v) carries out wash-out, thin-layer chromatography detects, obtain 42 milligrams of 64.6 milligrams of Siraitic acid IIB and Siraitic acid IIC, detect through HPLC, Siraitic acid IIB purity is 98.1%, and Siraitic acid IIC purity is 99.0%.
Embodiment 2:
Getting Momordica grosvenori root fragment (20 order) 2000 grams that exsiccant is collected in Longjiang township, Yongfu, Guilin, to be soaked in 8 liters of volumetric concentrations be in 80% the methyl alcohol, 80 ℃ of refluxing extraction 3 times, and each 2 hours, filter, united extraction liquid, decompression recycling ethanol get medicinal extract 78 grams.Medicinal extract is dissolved in 1 liter of distilled water, filter, filtrate is crossed AB-8 type macroporous resin column, water successively, volumetric concentration is 50% methyl alcohol, volumetric concentration is 100% methyl alcohol gradient elution, collect 100% meoh eluate, reclaim under reduced pressure methyl alcohol gets medicinal extract 3.5 grams, uses silica gel column chromatography then, with chloroform: methyl alcohol: water=20: 1: 0.1～5: 1: 0.1 (v/v) mixed solvent gradient elution, thin-layer chromatography detects, and collects the stream part that contains Siraitic acid IIB and Siraitic acid IIC, again through dextrane gel Sephadex LH-20 chromatography, with volumetric concentration is that 100% methyl alcohol carries out wash-out, thin-layer chromatography detects, and collects the part that contains target compound, through C
18Reversed-phase column separates, with methyl alcohol: water=4: 2 (v/v) carries out wash-out, thin-layer chromatography detects, obtain 25 milligrams of 40 milligrams of Siraitic acid IIB and Siraitic acid IIC, detect through HPLC, Siraitic acid IIB purity is 98.4%, and Siraitic acid IIC purity is 98.2%.
Embodiment 3:
Getting Momordica grosvenori root fragment (40 order) 3000 grams that exsiccant is collected in Longjiang township, Yongfu, Guilin, to be soaked in 18 liters of volumetric concentrations be in 90% ethanol, 85 ℃ of refluxing extraction 2 times, each 4 hours, filter, united extraction liquid, decompression recycling ethanol, medicinal extract 130 grams.Medicinal extract is dissolved in 2 liters of distilled water, filter, filtrate is crossed Diaion HP20 type macroporous resin column, water successively, volumetric concentration is 50% methyl alcohol, volumetric concentration is 100% methyl alcohol gradient elution, collect 100% meoh eluate, reclaim under reduced pressure methyl alcohol gets medicinal extract 5.7 grams, uses silica gel column chromatography then, with chloroform: methyl alcohol: water=20: 1: 0.1～5: 1: 0.1 (v/v) mixed solvent gradient elution, thin-layer chromatography detects, and collects the stream part that contains Siraitic acid IIB and Siraitic acid IIC, again through dextrane gel Sephadex LH-20 chromatography, carry out wash-out with 100% methyl alcohol, thin-layer chromatography detects, and collects the part that contains target compound, through C
18Reversed-phase column separates, with methyl alcohol: water=1: 4 (v/v) carries out wash-out, thin-layer chromatography detects, obtain 48 milligrams of 70.5 milligrams of Siraitic acid IIB and Siraitic acidIIC, detect through HPLC, Siraitic acid IIB purity is 99.0%, and Siraiticacid IIC purity is 98.5%.
Experimental example:
1 material and instrument
1.1 material: exsiccant Momordica grosvenori root fragment (being collected in Longjiang township, Yongfu, Guilin)
1.2 instrument:
TC-15 heating and refluxing extraction instrument (Great Wall, Zhengzhou science, industry and trade company); Silica gel 200-300 order (Haiyang Chemical Plant, Qingdao); Sephadex column Sephadex LH-20 (Sweden AmershamBioschiences AB); C
18Reversed material (Chromatorex Japanese fuji chemical company); JEOLA500MHz nuclear magnetic resonance analyser (Japanese beam split Co., Ltd.); JEOL JMS-DX303HF high resolution mass spectrometer (Jeol Ltd.); METTLER AT200 balance (Switzerland Mei Tele company); DIP-1000KUY polarimeter (Japanese beam split Co., Ltd.); R-200 type Rotary Evaporators (Switzerland B ü chi company); 2010 type microplate reader (Zhengzhou Autobio Co., Ltd).
The preparation of 2 saponins compound Siraitic acid IIB and Siraitic acid IIC
With above-mentioned embodiment 1.
3 structural analyses
3.1 the structural analysis of Siraitic acid IIB
Compound S iraitic acid IIB is white amorphous powder, [α]
25D+10.4 ° (MeOH, C=0.2).Accurate total mass number that must this compound by the fast atom bombardment(FAB) high resolution mass spectrum is 817.4073[M+Na]
+, calculate that its molecular formula is C
41H
62O
15 1H and
13The C nuclear magnetic resonance data sees Table 1.
Table 1: compound S iraitic acid IIB's
1H and
13NMR data (the in C of C
5D
5N)
500MHz?for
13C，500MHz?for?
1H
G-glucose, bracket inner digital are coupling constant J (Hz) value.
The chemical structural formula that can be determined Siraitic acid IIB by the nuclear magnetic resonance data in the above-mentioned table 1 is as follows:
3.2 the structural analysis of Siraitic acid IIC
Compound S iraitic acid IIC is white amorphous powder, [α]
25D+18.4 ° (MeOH, C=0.2).Accurate total mass number that must this compound by the fast atom bombardment(FAB) high resolution mass spectrum is 787.4639[M+Na]
+, calculate that its molecular formula is C
40H
60O
14 1H and
13The C nuclear magnetic resonance data sees Table 2.
Table 2: the 1H of compound S iraitic acid IIC and NMR data (the in C of 13C
5D
5N)
M500MHz?for?
13C，500MHz?for?
1H
G-glucose, bracket inner digital are coupling constant J (Hz) value.
The chemical structural formula that can be determined Siraitic acid II C by the nuclear magnetic resonance data in the above-mentioned table 2 is as follows:
4 antitumor activity in vitro
The applicant has carried out antitumor activity in vitro to chemical combination Siraitic acid II B and the Siraitic acid II C for preparing, and shows that two kinds of compounds all have the effect of obvious suppression tumour.
The cell strain that test is selected for use is international tumor cell line, for: A549 (lung cancer), Hep-G2 (liver cancer), test method is international mtt assay.
4.1Siraitic the antitumor activity in vitro of acid IIB:
4.1.1 test method:
Get the A549 and the Hep-G2 JEG-3 that are in logarithmic phase, being deployed into concentration with the RPMI-1640 nutrient solution behind the cell counting is 5000/ml, is inoculated in 96 well culture plates, and every hole adds the 190ul tumour cell, at 37 ℃ and 5%CO
2Cultivate under the condition after 24 hours and add sample compound S iraitic acid II B (10ul/ hole), establish 10,20,50,100,150,6 concentration of 200ug/ml, establish blank group and control group simultaneously, establish 3 parallel holes for every group, at 37 ℃ and 5%CO
2Cultivate after 96 hours under the condition, discard nutrient solution in the hole, every hole adds 200ul, 0.2mg/mlMTT solution (with the preparation of 1640 substratum), continues at 37 ℃ and 5%CO behind the concussion mixing
2Cultivated 4 hours under the condition, abandoning supernatant adds the DMSO200ul/ hole, and microplate reader is measured its OD
550Value is calculated inhibiting rate, and asks IC by concentration-inhibiting rate curve
50Inhibiting rate %=(the average OD value of the average OD value/control group of 1-experimental group) * 100%.
4.1.2 test-results:
The result shows: when sample effect after 96 hours, compound S iraitic acid IIB is to the Growth Inhibition half-inhibition concentration IC of A549 and Hep-G2 cancer cells
50Be respectively 9.2 μ g/ml and 5.9 μ g/ml.Experimental result shows that compound S iraitic acid II B has the obvious suppression effect to the growth of A549 and Hep-G2 cancer cells.
4.2 the antitumor activity in vitro of Siraitic acid IIC:
4.2.1 experimental technique: get the Hep-G2 JEG-3 that is in logarithmic phase, method and antitumor test with above-mentioned Siraitic acid IIB is set.
4.2.2 test-results:
The result shows: when sample effect after 96 hours, compound S iraitic acid IIC is to the Growth Inhibition half-inhibition concentration IC of cancer cells Hep-G2
50Be 10.4 μ g/ml.Experimental result shows that compound S iraitic acid IIC has the obvious suppression effect to the growth of Hep-G2 cancer cells.
Claims (4)
1. the saponins compound of extraction separation from Momordica grosvenori root, it is characterized in that: described saponins compound is Siraitic acid II B and Siraitic acid II C, and wherein, the structural formula of Siraiticacid II B is as shown in the formula shown in (I):
The structural formula of Siraitic acid II C is as shown in the formula shown in (II):
2. the preparation method of the described saponins compound of claim 1 is characterized in that it may further comprise the steps:
(1) extracts: get the Momordica grosvenori root fragment with methyl alcohol or ethanolic soln heating and refluxing extraction, extracting solution reclaims methyl alcohol or ethanol, the medicinal extract that obtains is dissolved in the distilled water, filter, solution is by macroporous resin column, and water, 50% methyl alcohol and 100% methanol-eluted fractions are collected 100% meoh eluate successively, reclaim methyl alcohol, get total saponin extracts;
Wherein, the volumetric concentration of described methyl alcohol or ethanolic soln is 80～100%, and its consumption is 4～6 times of Grosvenor Momordica fragment weight;
The number of times of described extraction is 2～3 times, and each time of extracting is 2～4 hours;
Described macroporous adsorptive resins is D101 type, AB-8 type or Diaion HP20 type;
(2) separate: above-mentioned total saponin extracts applying silicon plastic column chromatography, with chloroform: methyl alcohol: the mixed solvent gradient elution of the volume ratio of water=20: 1: 0.1～5: 1: 0.1, thin-layer chromatography detects, and collects the stream part that contains Siraitic acid IIB and Siraitic acid IIC; Through dextrane gel Sephadex LH-20 chromatography, carry out wash-out with 100% methyl alcohol again, thin-layer chromatography detects, and collects the stream part that contains target compound; After C
18Reversed phase column chromatography, with methyl alcohol: the mixed solvent of the volume ratio of water=1: 4～4: 2 carries out wash-out, and thin-layer chromatography detects, and obtains Siraitic acid IIB and Siraitic acid IIC.
3. the purposes of the described saponins compound Siraitic of claim 1 acid IIB in preparation anti-liver cancer and lung-cancer medicament.
4. the described saponins compound Siraitic of claim 1 acid IIC is in the purposes of preparation in the medicines resistant to liver cancer.
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| CN102048885B (en) * | 2011-01-10 | 2012-01-04 | 广州市中医医院 | Extraction process for lychee seed saponin |
| CN102526073A (en) * | 2012-01-06 | 2012-07-04 | 复旦大学 | Application of mogrol H9 for preparing antitumor drugs |
| CN105832748B (en) * | 2016-05-06 | 2019-06-07 | 深圳以诺生物制药有限公司 | A method of preparing momordica grosvenori alcohol derivative from momorside |
| CN106963801A (en) * | 2017-03-29 | 2017-07-21 | 桂林实力科技有限公司 | The preparation method of Fructus Monordicae extract |
| CN111297936B (en) * | 2020-02-24 | 2021-08-10 | 湖南华诚生物资源股份有限公司 | Method for extracting and separating total flavone, total triterpenoid saponin and total polysaccharide from momordica grosvenori roots |
| CN113121632B (en) * | 2021-05-06 | 2022-04-19 | 湖南华诚生物资源股份有限公司 | Method for extracting and separating momordica grosvenori acid from momordica grosvenori roots |
| CN113121633B (en) * | 2021-05-06 | 2022-05-27 | 湖南华诚生物资源股份有限公司 | Method for separating various mogrosic acid monomers from momordica grosvenori roots by continuous method |
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| CN101029071A (en) * | 2007-04-05 | 2007-09-05 | 上海交通大学 | Method for preparing high-purity Momordia grosvenori aglycone from Momordia grosvenori |
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