CN110627861B - Anemarrhena steroid saponin compound and preparation method and application thereof - Google Patents
Anemarrhena steroid saponin compound and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a rhizoma anemarrhenae steroid saponin compound, a preparation method thereof and application of the compound in preparing an anti-tumor medicament. The compound is spirostanol-type steroid saponin with molecular formula of C45H74O17And the molecular weight is 886. The compound is obtained by extracting rhizoma anemarrhenae as a medicinal plant with 75% ethanol, extracting with water-saturated n-butanol, and separating and purifying by adopting various methods such as macroporous adsorption resin, silica gel column chromatography, ODS reversed phase column chromatography, gel column chromatography and the like. MTT experimental results show that the compound has obvious antitumor activity on human breast cancer cell lines (MCF-7) and human liver cancer cell lines (HepG2), and is expected to become an antitumor candidate drug.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to a timosaponin compound, a preparation method thereof and application thereof in preparing antitumor drugs.
Background
Cancer, a major cause of human death, has now become a global public health problem. Because of the high mortality rate, low therapeutic efficacy, difficulty in control, etc., many scientists have focused their efforts on developing new therapeutic approaches and new chemotherapeutic strategies for treating various cancers. However, in recent years, various countries have focused on natural drugs because of the significant side effects and high treatment costs associated with some treatment regimens.
The natural medicine has the advantages of wide action target and low toxicity, and gradually becomes the focus of research on cancer treatment medicines, and makes great progress in the aspect of cancer treatment. At present, many drugs applied clinically are directly or indirectly derived from natural products, and the natural products can be used as a lead compound for drug semi-synthesis and a template for drug synthesis, so that a novel idea is provided for the design of new drugs. The bioactive components of natural medicines gradually show unique advantages and wide application prospects.
Rhizoma anemarrhenae (Anemarrhena asphodeloides Bge.) is dry rhizome of Anemarrhena asphodeloides bunge of Anemarrhena of Liliaceae, is mainly distributed in Hebei province and Anhui province of China, has effects of clearing heat and purging pathogenic fire, nourishing yin and moistening dryness, and can be used for fever polydipsia, lung heat dry cough, bone steaming hectic fever, internal heat diabetes, and constipation due to intestinal dryness. Research shows that the rhizoma anemarrhenae mainly contains steroidal saponins, polysaccharides, flavonoids, lignin and other components, wherein the steroidal saponins and aglycones thereof are main bioactive components of the rhizoma anemarrhenae, have various pharmacological activities such as anti-tumor, anti-inflammatory, antiviral and antifungal activities, and the content of the steroidal saponins and aglycones in the rhizome is about 6 percent of the total components. The steroid saponin compounds and the activity thereof related to the invention have not been found in patents or literature reports so far.
Disclosure of Invention
The invention aims to provide novel steroid saponin extracted and separated from rhizome of anemarrhena asphodeloides bunge, a preparation method thereof and application thereof in the aspect of tumor resistance.
A timosaponin steroid saponin compound has a structural formula shown in formula I:
the parent nucleus of the steroid saponin compound is saxasapogenin, belonging to spirostanol type steroids; the glycosyl group connected to the 3-position of the steroid is galactosyl, glucosyl and rhamnosyl in sequence, and the glycosyl group connection modes are all 1 → 2 connection.
The preparation method of the steroid saponin compound comprises the following steps:
and 3, roughly separating the n-butanol extract by using macroporous adsorption resin, performing first gradient elution by using ethanol-water in a volume ratio of 10:90-95:5, roughly separating the eluate by using silica gel column chromatography, performing second gradient elution by using dichloromethane-methanol in a volume ratio of 20:1-1:1, performing first ODS (ODS) reverse phase column chromatography on the eluate, performing third gradient elution by using methanol-water in a volume ratio of 30:70-100:0, performing second ODS reverse phase column chromatography on the eluate, performing fourth gradient elution by using methanol-water in a volume ratio of 30:70-100:0, performing gel column chromatography on the eluate, and purifying after methanol elution to obtain the steroid saponin compound.
Further, in the step 1, the ethanol is 75% ethanol aqueous solution by volume concentration, and 5L ethanol aqueous solution (75%) is used for each 1kg of dried rhizoma anemarrhenae; the reflux extraction times are 3 times, and each extraction time is 3 h.
Further, in the step 2, petroleum ether, ethyl acetate and water saturated n-butanol are adopted for extraction in sequence, wherein the volume of the organic solvent is the same as that of the suspension in each extraction.
Further, the macroporous adsorption resin in the step 3 is D101 type, and the volume ratio of ethanol to water is 10:90, 30:70, 50:50, 70:30 and 95:5 in sequence when the ethanol-water is used for the first gradient elution; the eluate with the ethanol-water volume ratio of 70:30 was subjected to silica gel column chromatography for coarse separation.
Further, the volume ratio of dichloromethane-methanol in the second gradient elution with dichloromethane-methanol in step 3 is 20:1, 10:1, 5:1, 3:1, 2:1 and 1:1 in sequence; the eluate, having a dichloromethane-methanol volume ratio of 2:1, was subjected to a first ODS reverse phase column chromatography.
Further, in the step 3, when the methanol-water is used for the third gradient elution, the volume ratio of the methanol to the water is 30:70, 50:50, 55: 45. 60:40, 65:35, 67:33, 70:30, 75:25, 78:22, 85:15, 90:10, 100: 0; the eluate, with a methanol-water volume ratio of 75:25, was subjected to a second ODS reverse phase column chromatography.
Further, in the step 3, the methanol-water volume ratios in the fourth gradient elution with methanol-water are 30:70, 50:50, 60:40, 65:35, 70:30, 73:27, 76:24, 80:20, 83:17, 86:14, 90:10 and 100:0 in sequence; the eluate, with a methanol-water volume ratio of 80:20, was subjected to gel column chromatography.
The steroid saponin compound can be used for preparing antitumor drugs.
Further, the tumor is breast cancer and liver cancer.
Has the advantages that:
1. the compound I provided by the invention has a novel structure, and the extraction and separation method is simple.
2. The compound I provided by the invention has obvious antitumor activity and has a prospect of being developed into a medicament for treating breast cancer or liver cancer.
Drawings
FIG. 1 is an HR-ESI-MS spectrum of the steroid saponin compound of the present invention.
FIG. 2 is an ESI-MS spectrum of a steroid saponin compound of the present invention.
FIG. 3 shows the preparation of steroid saponin compounds of the present invention1H-NMR(300MHz，Pyridine-d5) And (4) mapping.
FIG. 4 shows the preparation of steroid saponin compounds of the present invention13C-NMR(75MHz，Pyridine-d5) And (4) mapping.
Fig. 5 is an HSQC spectrum of the steroid saponin compounds of the present invention.
Fig. 6 is an HMBC profile of a steroid saponin compound of the present invention.
FIG. 7 shows the preparation of steroid saponin compounds of the present invention1H-1H COSY map.
Fig. 8 is a NOESY pattern of the steroid saponin compounds of the present invention.
Fig. 9 is a graph of key NOESY and HMBC related effects of the steroid saponin compounds of the present invention.
Detailed Description
The technical solution of the present invention is further illustrated by the following specific examples.
Example 1
Preparation of steroid saponin compound
Weighing 10kg of dried rhizome of common anemarrhena rhizome, placing the dried rhizome of common anemarrhena rhizome into an extraction tank, adding 50L of 75% ethanol, soaking overnight, heating in a water bath, refluxing and extracting for 3h, filtering, repeatedly extracting filter residue with 75% ethanol (50L) for 2 times, 3h each time, combining filtrates of three times, and concentrating to obtain an extract-like ethanol extract (3.09 kg). Suspending the ethanol extract in purified water to obtain suspension, sequentially extracting with petroleum ether, ethyl acetate, and water saturated n-butanol for 3 times, and concentrating the extractive solution to obtain three extracts. Subjecting the n-butanol extract (600g) to coarse separation with macroporous adsorbent resin, performing first gradient elution with 10%, 30%, 50%, 70%, and 95% (v/v) ethanol-water, and subjecting the eluate of 70% ethanol fraction to silica gel column chromatography. And then carrying out second gradient elution by using dichloromethane-methanol with the volume ratio of 20:1-1:1(v/v), wherein the elution ratio of dichloromethane-methanol is 20:1, 10:1, 5:1, 3:1, 2:1 and 1:1(v/v), and carrying out first ODS reverse phase column chromatography on the eluate with the volume ratio of dichloromethane-methanol of 2: 1. Performing gradient elution with methanol-water (30:70-100:0, v/v) for the third time at a methanol-water elution ratio of 30%, 50%, 55%, 60%, 65%, 67%, 70%, 75%, 78%, 85%, 90%, 100% (v/v), separating the eluate at 75% methanol position with ODS reversed phase column chromatography for the second time, performing gradient elution with methanol-water (30:70-100:0, v/v) for the fourth time at a methanol-water elution ratio of 30%, 50%, 60%, 65%, 70%, 73%, 76%, 80%, 83%, 86%, 90%, 100% (v/v), further subjecting the eluate of the 80% methanol fraction of the second ODS reverse phase column chromatography to gel column chromatography, eluting with methanol, and purifying to obtain compound I.
The compound I is white powder,
the compound is easy to dissolve in pyridine and dimethyl sulfoxide, can be dissolved in methanol, is yellow-green in a 10% sulfuric acid-ethanol solution, is purple-red-green in a Liebermann-Burchard reaction, and is purple-ring in a Molish reaction. As shown in FIGS. 1 and 2, HR-ESI-MS showed an excimer peak of 885.4873[ M-H ]]-Determining the formula of Compound I as C45H74O17(unsaturation degree 9).
As shown in figure 3 of the drawings,1H-NMR(300MHz，Pyridine-d5) In the spectrum, δH4.95(1H, d, J ═ 7.1Hz), 5.77(1H, d, J ═ 7.0Hz), and 6.35(1H, brs) are each the terminal hydrogen (H-1', H-1 "') signals for 3 sugars, suggesting that the compound contains 3 sugar groups. DeltaHThe unimodal signal of 6.35 is the terminal hydrogen of rhamnose (H-1') signal, δH1.86(3H, d, J ═ 6.2Hz) bimodal signal is the methyl hydrogen signal on rhamnose; deltaH0.84(3H, s) and 1.01(3H, s) of two unimodal signals are methyl at 18 and 19 positions on a steroid parent nucleus respectivelyHydrogen signal, deltaHTwo doublet signals 1.17(3H, d, J ═ 6.8Hz), 1.09(3H, d, J ═ 7.1Hz) are methyl hydrogen signals at positions 21 and 27 on the steroid parent nucleus, respectively.
As shown in figure 4 of the drawings,13C-NMR(75MHz，Pyridine-d5) High field region delta in the spectrumC16.98, 24.38, 15.30 and 16.70 are methyl carbon signals of C-18, 19, 21 and 27 positions on aglycone respectively, deltaC19.51 is the methyl carbon signal on rhamnose; low field region deltaC102.00, 102.40, 102.79 are signals of 3 terminal carbons (C-1' ) of the sugar, respectively, suggesting that the compound is a steroid saponin linked with three sugars, one of which is rhamnose.
Determination of monosaccharide type and configuration in Compound I
Hydrolyzing a compound I with 2mol/L hydrochloric acid, carrying out PMP derivatization reaction, analyzing a derivatization product through HPLC, comparing monosaccharide standard substances, determining that sugars connected with the compound I are respectively D-glucose, D-galactose and L-rhamnose, and determining that the proportion of the three is 1 by combining spectral data: 1: 1. coupling constants based on galactose terminal hydrogens3J1,27.1Hz, coupling constant of the terminal hydrogens of glucose3J1,2Determining that the two six-carbon sugars are both sugars in the beta configuration at 7.0 Hz; according to13The rhamnosyl C-3 '(delta 73.19) and C-5' (delta 69.98) in a C-NMR spectrum are compared with the literature, and the rhamnose configuration is determined to be alpha configuration.
Preparation of compound I1H-NMR，13C-NMR data and timosaponin A III were compared, and the data of both in the aglycon part were found to be substantially identical. As shown in FIGS. 7-9, in the NOESY spectrum, δH 1.01(3H,s,CH3-19) and δH2.45(1H, d, J ═ 12.5Hz, H-5) correlation, suggesting that compound H-5 is in the β configuration.
As shown in FIG. 5, in the HSQC spectrum, the two hydrogen signals at the C-26 methylene group are δH4.08(1H, m), 3.38(1H, d, J ═ 10.8Hz), from which the difference δ in chemical shift between the two hydrogens at that position is knownΔab＝δa-δbAt 0.70ppm, the binding literature identifies C-25 as the S configuration. Mass spectrometry showed that compound I had a molecular weight of 886, specific timosaponin A III (molecular weight 7)40) Poly 146, corresponding to one molecule of methyl five carbon glycosyl. Combining the analysis results, the compound I is determined to be spirost saponin with aglycone being saxasapogenin and glycosyl being three sugars (galactose, glucose and rhamnose).
As shown in FIG. 6, in the HMBC spectra, Gal-H-1' (δ)H4.95) and C-3 (. delta.))C75.25) correlation, indicating that galactose is connected to the C-3 position of aglycone; Glc-H-1' (delta)H5.77) and Gal-C-2' (delta)C77.02) relative to each other, indicating that glucose is attached to the C-2' position of galactose; Rha-H-1' (delta)H6.35) with Glc-C-2' (delta)C79.79), indicating that rhamnose is attached to the C-2 "position of glucose. In conclusion, the connection sequence of the aglycone C-3 sugar is determined to be alpha-L-rhamnopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 2) -beta-D-galactopyranoside.
In conjunction with the above analysis, the structure of compound I was finally determined to be: (25S) -5 beta-spirostane-3 beta-ol-3-O-alpha-L-rhamnopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 2) -beta-D-galactopyranoside. As shown in the following formula:
table 1: of the Compound I1H-NMR(300MHz,Pyr-d5) And13C-NMR(75MHz,Pyr-d5) Data of
Example 2
Antitumor Activity assay of Compound I
1. The cell strain and reagent materials, namely human breast cancer cell strain MCF-7 and human liver cancer cell strain HepG2, are provided by American Type Culture Collection (ATCC); DMEM medium, RPMI-1640 medium, fetal bovine serum, trypsin, DMSO, MTT and the like.
2. MTT method for detecting cell survival rate
Culturing MCF-7 and HepG2 cell lines in RPMI-1640 medium containing 10% fetal calf serum, and collecting the culture solutionMCF-7 and HepG2 cell strains in a logarithmic growth phase and in a good state are discarded from a culture medium, washed three times by precooled sterile PBS, digested by pancreatin solution and observed by an inverted biomicroscope, and the cells are mixed uniformly after digestion is finished. MCF-7 and HepG2 cell lines are respectively paved on a 96-well plate to ensure that the MCF-7 cell line is 2500 cells/well and the HepG2 cell line is 2000 cells/well, and the MCF-7 cell line and the HepG2 cell line are cultured for 24h for administration, wherein the drug concentration is set to be 100 mu mol/L, 10 mu mol/L, 1 mu mol/L and 0.1 mu mol/L. After 72h of drug action, the cells were incubated for 4h with 10. mu.L MTT/well and then with 100. mu.L DMSO/well, shaken for 5min with a shaker, and the absorbance (OD) was measured at 570nm wavelength (. lamda.) for each well. The cell proliferation inhibition rate was calculated as follows: the inhibition rate of cell proliferation (1-OD value of experimental group/OD value of control group) × 100%, and IC was calculated by GraphPad software50(median inhibitory concentration) value.
3. Test results
The experimental results show that the IC of the compound I on MCF-7 and HepG2 cell lines50The values are respectively 2.16 +/-0.19 mu mol/L and 2.02 +/-0.19 mu mol/L, which shows that the compound I has obvious inhibition effect on breast cancer cells and liver cancer cells. Therefore, the steroid saponin has a prospect of being developed into an anti-tumor medicament.
Claims (4)
1. A timosaponin compound is characterized in that: the structural formula is shown as formula I:
2. a process for the preparation of a steroid saponin compound as claimed in claim 1, characterized in that: the method comprises the following steps:
step 1, taking dry rhizome of rhizoma anemarrhenae, heating and refluxing the rhizome of rhizoma anemarrhenae by using ethanol, and concentrating the rhizome of rhizoma anemarrhenae to obtain extractum-shaped ethanol extract;
the ethanol is 75% ethanol water solution, wherein 5L 75% ethanol water solution is used for each 1kg dried rhizome of rhizoma anemarrhenae; the reflux extraction times are 3 times, and each extraction time is 3 hours;
step 2, suspending the ethanol extract in purified water to obtain a suspension, sequentially extracting with petroleum ether, ethyl acetate and water-saturated n-butanol, wherein the volume of an organic solvent is the same as that of the suspension during each extraction, and concentrating the extract to obtain three extracts;
step 3, roughly separating the n-butanol extract by macroporous adsorption resin, performing first gradient elution by using ethanol-water in a volume ratio of 10:90-95:5, roughly separating the eluate by using silica gel column chromatography, performing second gradient elution by using dichloromethane-methanol in a volume ratio of 20:1-1:1, performing first ODS (ODS) reverse phase column chromatography on the eluate, performing third gradient elution by using methanol-water in a volume ratio of 30:70-100:0, performing second ODS reverse phase column chromatography on the eluate, performing fourth gradient elution by using methanol-water in a volume ratio of 30:70-100:0, performing gel column chromatography on the eluate, and purifying after methanol elution to obtain a steroid saponin compound;
the macroporous adsorption resin is D101 type, the volume ratio of ethanol to water is 10:90, 30:70, 50:50, 70:30 and 95:5 in sequence when ethanol-water is used for the first gradient elution, and the eluate with the volume ratio of ethanol to water of 70:30 is subjected to silica gel column chromatography rough separation;
performing second gradient elution with dichloromethane-methanol at a volume ratio of 20:1, 10:1, 5:1, 3:1, 2:1, 1: 1; separating the eluate with a dichloromethane-methanol volume ratio of 2:1 by first ODS reversed-phase column chromatography;
and when the methanol-water is adopted for the third gradient elution, the volume ratio of the methanol to the water is 30:70, 50:50 and 55: 45. 60:40, 65:35, 67:33, 70:30, 75:25, 78:22, 85:15, 90:10, 100: 0; separating the eluate with methanol-water volume ratio of 75:25 by second ODS reversed-phase column chromatography;
performing gradient elution with methanol-water for the fourth time, wherein the volume ratio of methanol to water is 30:70, 50:50, 60:40, 65:35, 70:30, 73:27, 76:24, 80:20, 83:17, 86:14, 90:10 and 100:0 in sequence; the eluate, with a methanol-water volume ratio of 80:20, was subjected to gel column chromatography.
3. Use of a steroid saponin compound as claimed in claim 1 in the preparation of an anti-tumour medicament.
4. Use according to claim 3, characterized in that: the tumor is breast cancer or liver cancer.
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