CN115433248B - Novel amino acid derivative separation and identification in red ginseng and novel application thereof - Google Patents

Novel amino acid derivative separation and identification in red ginseng and novel application thereof Download PDF

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CN115433248B
CN115433248B CN202211225983.XA CN202211225983A CN115433248B CN 115433248 B CN115433248 B CN 115433248B CN 202211225983 A CN202211225983 A CN 202211225983A CN 115433248 B CN115433248 B CN 115433248B
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李伟
段月阳
王梓
任珅
霍德洋
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Jilin Agricultural University
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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
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Abstract

The invention relates to the field of natural pharmaceutical chemistry, and particularly discloses separation and purification of a novel amino acid derivative compound in Red ginseng (Red ginseng) and a novel application of the novel amino acid derivative compound. The compound is subjected to structure identification by adopting an amino acid automatic analyzer, nuclear magnetic resonance and positive and negative ion mass spectrometry, the molecular formula and the structural formula of the compound are deduced, and the compound is finally named as histadin-glucoside (HFG). Further in vitro cell activity screening results show that HFG has a good protective effect on HUVECs cell damage induced by glucose, and can be applied to preparation of medicaments for protecting cardiovascular diseases.

Description

Novel amino acid derivative separation and identification in red ginseng and novel application thereof
The technical field is as follows:
the invention belongs to the technical field of medicines, and particularly relates to a novel amino acid derivative in red ginseng and a separation and preparation method thereof.
The background art comprises the following steps:
ginseng Radix Rubri (Ginseng Radix et Rhizoma Rubra) is dried root and rhizome of Panax Ginseng C.A.Mey. Of Araliaceae, and is a traditional Chinese medicine with long application history. Warm in nature, sweet in taste and slightly bitter in taste, has the effects of greatly invigorating primordial qi, recovering pulse, relieving depletion, benefiting qi and controlling blood, and is used for treating symptoms such as weak body, desire for depletion, cold limbs, slight pulse, qi failing to control blood, metrorrhagia and metrostaxis.
Ginseng, as one of the rare Chinese medicinal materials, is rich in various components, and has a series of changes in the steaming process, so that the components in Ginseng radix Rubri are diversified. It is noted that some of the amino acid components in many of the compounds produced undergo maillard reactions, mainly with reducing sugars, via aldol condensation reactions, via Amadori rearrangement. In 1996, professor Zhengyi and Neutral discovered and separated from Ginseng radix Rubri for the first time, a brand new amino acid derivative-AFG (aryl-40-glucose) and AF (aryl-40-glucose) is purified, and is indicated to be one of Maillard products formed by Maillard reaction in the ginseng processing process, and the diversity of non-saponin components in Ginseng radix Rubri is primarily disclosed.
Currently, cardiovascular diseases are an important factor of health loss in various regions of the world, and more research is being devoted to finding new and effective drugs that can be used for preventing and treating cardiovascular diseases. Based on the traditional efficacy of red ginseng, the cardiovascular protection effect of red ginseng has been widely studied, and the main monomer components AFG and ginsenosides Rb1, rg1 and the like have been proved to have the protection effect.
So far, according to the research reports on the chemical components of red ginseng, no research report on the compound histidine diglycoside is found.
The invention content is as follows:
the invention innovatively discovers and separates histidine-fructose-glucose (HFG), a derivative of histidine and maltose.
The compound, namely the histidine bisglycoside HFG, is preliminarily proved to have the cardiovascular protection effect.
The invention provides a compound in red ginseng and a method for separating the compound from red ginseng.
The invention firstly provides a novel compound, which is named as histidine diglycoside and has the molecular formula: c 18 H 29 N 3 O 12 The structural formula is shown as the figure:
Figure GDA0004108015380000021
the method for separating the compound consists of the following steps:
A. extraction: weighing Ginseng radix Rubri powder (20 mesh sieve), extracting with 5 times of anhydrous alcohol (material-liquid ratio: g/mL) under stirring at room temperature for 12 hr (rotation speed 1000 rpm), repeating the extraction for three times, and discarding alcohol solution;
extracting with 10 times of distilled water under stirring at room temperature for 8 hr (material-to-liquid ratio: g/mL, rotation speed 1000 rpm), repeating the extraction for five times, mixing extractive solutions, and concentrating at low temperature to small volume of about 10g/mL.
B. Removing sugar and saponin: precipitating with 80% ethanol/water solution, removing most sugar, removing alcohol from supernatant, concentrating to small volume (about 10 g/mL), passing through macroporous resin, eluting with water, collecting water eluate, concentrating, and lyophilizing.
C. Dissolving the lyophilized powder in double distilled water (concentration: 1 g/mL), passing through Sephadex LH-20 column, eluting with double distilled water, collecting ninhydrin positive reaction part, concentrating, and lyophilizing.
D. Dissolving the freeze-dried powder in a glacial acetic acid aqueous solution with the volume ratio of 0.2% to obtain a solution with the concentration of 1g/mL, passing through a Bio-gel P-2 column, eluting with 0.2% glacial acetic acid with the flow rate of 0.3mL/min, collecting components with the Rf =0.18, and freeze-drying to obtain the compound HFG.
The invention further provides application of the compound in preparing a medicine for protecting cardiovascular diseases, in particular application in preparing a medicine for preventing, treating or improving diabetes-induced vascular injury.
In a preferred embodiment of the present invention, the vascular injury includes atherosclerosis, vascular rupture, vasospasm, vascular contusion, and vascular compression.
In a preferred embodiment of the present invention, the vessel rupture includes a complete vessel rupture or a partial vessel rupture.
The invention further provides a pharmaceutical composition, which optionally comprises more than one auxiliary material, wherein the auxiliary material comprises an excipient, and the excipient comprises any one or more of an adhesive, a filler and a lubricant.
Compared with the prior art, the invention has the beneficial effects that:
the invention separates a new amino acid glucoside compound HFG from red ginseng, and the compound has better protective effect on HUVECs cell damage induced by glucose, and lays a foundation for the development and utilization of medicaments for protecting cardiovascular diseases.
Description of the drawings:
FIG. 1 is a spectrogram of an automatic amino acid analyzer of HFG of the present invention
FIG. 2 is an HPLC-ELSD spectrum of HFG of the present invention
FIG. 3 shows HFGs of the invention 1 H-NMR spectrum
FIG. 4 shows HFGs of the invention 13 C-NMR spectrum
FIG. 5 shows HMBC spectra of HFG of the present invention
FIG. 6 is an HSQC spectrum of HFG of the present invention
FIG. 7 is an HR-ESI-MS spectrum of an HFG of the present invention
FIG. 8 shows that HFG improves glucose-induced HUVECs cell damage
FIG. 9 is a graph showing the effect of AFG on glucose-induced HUVECs cell damage
The specific implementation mode is as follows:
the separation and purification method of the present invention will be further illustrated with reference to the following specific examples, but the scope of the present invention is not limited thereto.
EXAMPLE 1 isolation of HFG, a Compound of the invention
The formula of the compound HFG of this example is as follows:
Figure GDA0004108015380000041
1. the method for separating and preparing the compound HFG comprises the following steps:
A. taking red ginseng powder (sieving with a 20-mesh sieve), extracting with 5 times of anhydrous ethanol (material-liquid ratio: g/mL) under stirring at normal temperature for 12h (rotation speed 1000 rpm), repeating the extraction for three times, and removing ethanol solution; extracting the rest precipitate with 10 times of distilled water at room temperature under stirring for 8 hr (rotation speed 1000 rpm), repeating the extraction for five times, centrifuging, mixing the extractive solutions, and concentrating at low temperature to obtain a smaller volume of red ginseng and liquid with a ratio of about 10g/mL.
B. And B, taking the extract concentrated solution obtained in the step A, precipitating with 80% ethanol/water solution in volume ratio, standing at the temperature of 4 ℃ for 24 hours, centrifuging, and keeping the supernatant to remove most of sugar. Removing alcohol from the supernatant, concentrating to a small volume (volume ratio of about 10 g/mL), passing through NKA macroporous resin, eluting with water, collecting the water eluate, concentrating, and lyophilizing.
C. And D, dissolving the freeze-dried powder obtained in the step B in double distilled water to obtain a solution of 1g/mL, passing the solution through a Sephadex LH-20 column, eluting the solution by double distilled water, analyzing the solution by TLC, collecting a ninhydrin positive reaction part, concentrating and freeze-drying the ninhydrin positive reaction part.
D. Dissolving the freeze-dried powder in a glacial acetic acid aqueous solution with the volume ratio of 0.2% to obtain a solution with the concentration of 1g/mL, passing through a Bio-gel P-2 column, eluting with 0.2% glacial acetic acid with the flow rate of 0.3mL/min, collecting components with the Rf =0.18, and freeze-drying to obtain the compound HFG.
The HFG compound is a pale yellowish white solid, and is detected and analyzed by a full-automatic amino acid analyzer model L-8800, and the retention time of an absorption peak of the compound is 12.52min as shown in figure 1. The absorption peak retention time of the compound is 24.21min as detected by HPLC-ELSD as shown in FIG. 2.
2. The monomer compound is subjected to structural identification by using modern nuclear magnetic resonance technology and high-resolution mass spectrum HR-ESI-MS
As shown in FIGS. 1 to 7 and Table 1, according to HR-ESI-MS m/z:480.1813[ 2 ] M + H] + (calculated: 480.1785) and the molecular formula is determined to be C by combining NMR spectra 18 H 29 N 3 O 12 . The compound structure is identified as formula (I).
Process for preparing HFG of the Compound of Table 1 1 H and 13 C-NMR(600/100MHZ，D 2 o) data (ppm)
Figure GDA0004108015380000051
Example 2 protective effect of HFG, a compound of the present invention, on glucose-induced HUVECs cell damage in human umbilical vein endothelial cells.
1. Pharmaceutical formulation
HFG was dissolved in a DMEM high-sugar medium to give a 1mM/mL stock solution, which was diluted to the following concentrations: 1.0. Mu.M/mL, 2.0. Mu.M/mL, 4.0. Mu.M/L, 8.0. Mu.M/mL. Analytically pure glucose was dissolved in DMEM high-sugar medium to 150 mM/mL. HFG is unstable in property, the preparation needs to be carried out as it is, the whole process is finished under aseptic conditions, and a filter membrane is needed for use.
And taking arginine diglycoside (AFG) which is the unique component in red ginseng to carry out parallel experiments, the specific process is the same as above.
2. Cell culture
HUVECs cells were grown in DMEM high-glucose medium containing 10% fetal bovine serum and at 5% CO 2 And carrying out adherent culture in an incubator with saturated humidity and 37 ℃, and taking cells in logarithmic growth phase for experiment.
3. MTT method for testing influence of HFG on cell viability
HUVECs cell line 1.5X 10 5 Inoculating and 96-well plates at each/mL density, incubating in an incubator for 24h, then discarding the supernatant, pre-dosing with HFG and AFG at different concentrations, respectively, administering an equivalent amount of DMEM high-sugar medium to a control group and a model group, incubating in the incubator for 24h, then discarding the supernatant, molding with 150mM/mL glucose, administering an equivalent amount of DMEM high-sugar medium to a control group, adding 20 μ L of MTT solution (5 mg/mL) to each well after incubating in the incubator for 24h in a dark condition, discarding the supernatant after incubating in the incubator for 3.5h, adding 150 μ L of DMSO to each well, and measuring the absorbance (OD value) at 490nm by using an enzyme reader after fully vibrating the plates.
4. Data processing
Inter-group analysis of experimental data comparisons were statistically analyzed using standard deviation of Mean (Mean ± s.d.), using one-way analysis of variance (ANOVA), with p <0.05 or p <0.01 statistically significant, and histogram analysis using GraphPadPrism 9.0.0 software.
5. Results
The protective effect of HFG on glucose-induced HUVECs cell damage in human umbilical vein endothelial cells is shown in FIG. 8.MTT results showed that HFG doses at 1-2. Mu.M exhibited significant protection (p <0.05, p- <0.01). The results of the AFG group experiments are shown in FIG. 9.MTT results show that AFG has no obvious protective effect on HUVECs cell damage induced by high sugar.
Therefore, the HFG has better advantages in the aspect of the protective effect on the cell damage of HUVECs induced by glucose.
The invention has been described in detail with reference to the preferred embodiments and illustrative examples. It should be noted, however, that these specific embodiments are only illustrative of the present invention and do not limit the scope of the present invention in any way. Various modifications, equivalent substitutions and alterations can be made to the technical content and embodiments of the present invention without departing from the spirit and scope of the present invention, and these are within the scope of the present invention. The scope of the invention is defined by the appended claims.

Claims (9)

1. A compound is named as histidine bisglucoside, and the molecular formula of the compound is as follows: c 18 H 29 N 3 O 12 The structural formula is as follows:
Figure FDA0004077810270000011
2. a process for the preparation of a compound according to claim 1,
the method comprises the following steps:
A. pulverizing Ginseng radix Rubri, sieving with 20 mesh sieve, extracting with 5 times of anhydrous ethanol at 1000rpm under stirring at room temperature for 12 hr, repeating the extraction for three times, and removing ethanol solution; stirring and extracting for 8h at normal temperature with distilled water with the material-to-liquid ratio g/mL of 10 times, rotating at 1000rpm, repeating the distilled water extraction step five times, combining the extractive solutions, and concentrating under reduced pressure at room temperature to a smaller volume of 10g/mL;
B. precipitating with 80% ethanol/water solution, removing ethanol from the supernatant, concentrating to 10g/mL, passing through macroporous resin, eluting with water, collecting water eluate, concentrating, and lyophilizing;
C. dissolving the freeze-dried powder obtained in the step B in double distilled water according to the concentration of 1g/mL, passing through a SephadexLH-20 column, eluting by double distilled water, collecting the positive reaction part of ninhydrin, concentrating and freeze-drying;
D. and D, dissolving the freeze-dried powder obtained in the step C in a glacial acetic acid aqueous solution with the volume ratio of 0.2% according to the concentration of 1g/mL, passing through a Bio-gelP-2 column, eluting with the glacial acetic acid with the volume ratio of 0.2%, collecting components with Rf =0.18, and freeze-drying to obtain the compound histidine diglycoside.
3. The compound histidine bisglycoside as claimed in claim 1, which is a pale yellowish white solid, is unstable at room temperature, is easily decomposed by moisture absorption, and can be stored at-20 deg.C for a long period after sealing.
4. The compound histidine bisglycoside as claimed in claim 1, wherein the retention time of the absorption peak of the compound is 12.52min as determined by L-8800 automatic amino acid analyzer.
5. Use of a compound according to claim 1 for the manufacture of a medicament for the protection of cardiovascular diseases.
6. The use according to claim 5, wherein the use is in the preparation of a medicament for the prevention, treatment or amelioration of diabetes-induced vascular damage.
7. The use of claim 6, wherein said vascular injury comprises atherosclerosis, vascular rupture, vasospasm, vascular contusion, and vascular compression.
8. The use of claim 7, wherein the vessel disruption comprises a complete vessel disruption or a partial vessel disruption.
9. A pharmaceutical composition, which contains the compound of claim 1, and optionally comprises more than one auxiliary material, wherein the auxiliary material comprises an excipient, and the excipient comprises any one or more of a binding agent, a filling agent and a lubricating agent.
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