CN113072610B - Monomeric compound araloside A and in-vitro antioxidation thereof - Google Patents

Monomeric compound araloside A and in-vitro antioxidation thereof Download PDF

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CN113072610B
CN113072610B CN202110344551.XA CN202110344551A CN113072610B CN 113072610 B CN113072610 B CN 113072610B CN 202110344551 A CN202110344551 A CN 202110344551A CN 113072610 B CN113072610 B CN 113072610B
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apothecin
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裴凌鹏
孙九许
燕梦云
周文斌
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Abstract

The invention relates to the technical field of aralia elata seem research, and particularly relates to aralia elata seem saponin A serving as a monomer compound and in-vitro antioxidation of aralia elata seem saponin A. The invention provides a monomeric compound araloside A, which is prepared by separating a monomeric compound araloside A from medicinal plant araloside A for the first time, and researches on the in-vitro antioxidation effect of the monomeric compound, thereby providing reliable experimental data support and theoretical basis for the treatment effect of araloside A on relevant diseases (cardiovascular diseases, arthritis, age-related macular degeneration and the like) through antioxidation or free radical quenching functions.

Description

Monomeric compound araloside A and in-vitro antioxidation thereof
Technical Field
The invention relates to the technical field of aralia elata seem research, and particularly relates to aralia elata seem saponin A serving as a monomer compound and in-vitro antioxidation of aralia elata seem saponin A.
Background
Aralia echinacea hand-Mazz, which is a plant of Aralia genus of Araliaceae family, is widely distributed in China, and is grown in forests, and the vertical distribution altitude can reach 2600 m. The medicinal material is in the form of tablet or trough, slightly fragrant, sticky when chewed, pungent and neutral in flavor. It has effects in nourishing yin, invigorating kidney, dispelling pathogenic wind, removing dampness, strengthening bone and muscle, dispelling blood stasis, and removing toxic swelling, and can be used for treating rheumatalgia, traumatic injury, fracture, etc.
At present, the study of the aralia elata seem mostly focuses on the aspects of medicinal material identification, artificial cultivation, pharmacological action and the like, but the study on the basis of the pharmacodynamic substances is weak. The compounds separated and identified from the aralia elata seem at present comprise 10 saponins, 95 volatile oils, 1 organic acid and 1 sterol, and the aralia elata seem also contains abundant saccharides and trace elements. The contents of total polysaccharide and total flavone in the root bark of the aralia elata seem are respectively 7.33% and 0.92%, the contents of inorganic elements such as calcium, magnesium, cesium, gallium, copper, zinc and the like are higher, and particularly, the contents of copper, calcium and cesium are more than 10 times higher than those of the same Chinese herbal medicines. The Acanthopanax senticosus root bark can improve H by enhancing cell activity, increasing superoxide dismutase (SOD) activity and cell membrane fluidity, and reducing content of active free oxygen (ROS) and Lipid Peroxide (LPO)2O2To MC3T3-E1Oxidative damage of osteoblasts. But just thatThe study of monomeric compounds to quench free radicals from different sources in vitro is rare.
In summary, the prior art has the following disadvantages:
defect one: at present, the study of the aralia elata seem mostly focuses on the aspects of medicinal material identification, artificial cultivation, pharmacological action and the like, but the study on the basis of the pharmacodynamic substances is weak. The compounds separated and identified from the aralia elata seem at present comprise 10 saponins, 95 volatile oils, 1 organic acid and 1 sterol. The patent separates a monomer compound, namely the araloside A, from aralia elata.
And defect two: the in vitro antioxidant effect of the monomeric compound of the aralia elata seem at the present stage is not reported. The patent has the capability of removing DPPH free radicals in vitro from the aralia elata seem, the protection effect of OH induced DNA oxidative damage and H2O2The protective effect of inducing oxidative damage to DNA was studied for the first time.
Disclosure of Invention
In view of the above, the present invention aims to provide a monomeric compound apothecin A and its in vitro antioxidant effect, i.e. the apothecin A is separated from the apothecin for the first time, i.e. the in vitro DPPH free radical scavenging ability of the apothecin A, the OH-induced DNA oxidative damage protective effect and H2O2The protective effect of inducing oxidative damage to DNA was studied for the first time.
In order to achieve the purpose, the invention provides the following technical scheme:
heating and reflux-extracting radix Et caulis Opuntiae Dillenii root bark 2.0kg with 70% ethanol for 3 times, adding 7L ethanol each time, heating for 2h, rotary evaporating to obtain 400mL extract, diluting 200mL extract with 10% ethanol to obtain 2.5L solution, passing through MCI-GEL macroporous resin, gradient eluting with ethanol-water according to 10%, 30%, 50%, 70%, and 90% ethanol, collecting each eluate, recovering solvent, and vacuum drying at low temperature to obtain 9 samples, which are respectively 10% ethanol Fr.1-4, 10% ethanol Fr.5-9, 30% ethanol Fr.1-3, 30% -50% ethanol Fr.3-4, 50% ethanol Fr.1, 50% ethanol Fr.2-3, 70% ethanol Fr.1, 70% ethanol Fr.2-4, and 90% ethanol Fr.1-3, and detecting by thin layer chromatography;
dissolving 50% ethanol Fr.1 part 13.00g in methanol, mixing with 30g silica gel, and dry packing with 4L column volume in CH2Cl2∶MeOH∶H2Gradient elution with O75: 20: 5, 70: 22: 5, 75: 25: 5, 70: 26: 5, 65: 25: 5, 70: 43: 10, and thin layer chromatography for mixing and concentrating to obtain 12 parts Fr.F1-12; f4 part 190mg was taken, dissolved in a solution of acetonitrile/water 28: 72, filtered and prepared via preparative liquid phase, mobile phase ratio: acetonitrile and water (28: 72) to obtain araloside A10mg
The acetonitrile to water solution was 28 to 72, the water contained 0.01% formic acid.
The aralia elata seem saponin A has a certain capacity of removing DPPH free radicals.
The aralia elata seem saponin A has a protective effect on OH-induced DNA oxidative damage.
The aralia elata seem saponin A has a protective effect on DNA oxidative damage induced by H2O 2.
Compared with the prior art, the invention firstly separates and prepares the apocynin A which is not reported by the plant from the medicinal plant, namely the apocynin A, and researches the in-vitro antioxidation effect of the apocynin A, thereby providing reliable experimental data support and theoretical basis for the treatment effect of the pachyrhizus on treating related diseases (cardiovascular diseases, arthritis, age-related macular degeneration and the like) through antioxidation or free radical quenching functions in the future.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The method for separating and identifying the araloside A comprises the following steps:
(1) extraction: heating and reflux-extracting 2.0kg of Aralia elata seem root bark with 70% ethanol for 3 times, adding 7L of ethanol each time, heating for 2h, rotary evaporating to obtain 400mL of extract, diluting 200mL of extract with 10% ethanol to obtain 2.5L of solution, passing through MCI-GEL macroporous resin, gradient eluting with ethanol-water (gradient of 10%, 30%, 50%, 70% and 90% ethanol), collecting each eluted part, recovering solvent, and vacuum drying at low temperature to obtain powder. 9 samples are obtained in total, and are respectively 10% ethanol Fr.1-4, 10% ethanol Fr.5-9, 30% ethanol Fr.1-3, 30% -50% ethanol Fr.3-4, 50% ethanol Fr.1, 50% ethanol Fr.2-3, 70% ethanol Fr.1, 70% ethanol Fr.2-4 and 90% ethanol Fr.1-3, and the detection is carried out by thin layer chromatography.
13.00g of 50% ethanol Fr.1 part is dissolved in methanol, 30g of silica gel (100-200 meshes) is used for sample mixing, and the mixture is packed into a column by a dry method, wherein the volume of the column is 4L. With CH2Cl2∶MeOH∶H2And gradient elution is carried out on the O of 75: 20: 5, 70: 22: 5, 75: 25: 5, 70: 26: 5, 65: 25: 5 and 70: 43: 10, and the mixture is combined and concentrated according to thin-layer chromatography to obtain 12 parts of Fr.F1-12. Fr. f4 fraction (190mg) was dissolved in a 28: 72 solution of acetonitrile/water (0.01% formic acid), filtered and prepared via preparative liquid phase, mobile phase ratio: acetonitrile and water (0.01% formic acid) 28: 72 to obtain Kalopanacis Saponin A (10 mg).
Separating and identifying a monomer compound (Kalopanax septemlobus saponin A) from Kalopanax septemlobus extract by MCI-GEL macroporous resin, silica GEL column and chromatography, and performing MS, chromatography, etc. on the compound,13C-NMR、1H-NMR、HSQC、HMBC、1The structure of the compound is identified by a spectroscopic method such as H-1HCOSY and the like, and the obtained data of the compound is not reported in the literature and is identified as a new compound.
(2) And (3) identification: saponin A (echinocaulis aponin A)
The aralia elata seem saponin A is white powder, and the sulfuric acid ethanol is purple. TOF-MS: m/z 695.4015[ M + COOH]-Molecular formula is C36H58O10(theoretical value 650.4030).1H NMR (table 1) showed that the compound had six methyl signals, δ 0.93(3H, s), 1.13(3H, s), 1.40(3H, s), 1.67(3H, s), 2.01(3H, s) and 1.26(d,3H, J ═ 6.2Hz), one alkane proton signal δ 4.89(2H, m), and a carbohydrate proton signal δ 3.5-6.0, respectively.13C NMR showed one olefin at delta 157.18, 106.06Carbon signal, one sugar end group carbon signal is shown at δ 107.17. δ 157.18 and δ 106.06 are typical terminal double bond signals. By passing1H-1H COZY, proton signals are related at δ 4.97(d, J ═ 7.7Hz), 4.04(d, J ═ 8.0Hz), 4.19(dd, J ═ 3.5,6.8Hz), 3.97(m)/4.18(m), 3.97(m) and 4.37(dd, J ═ 5.3, 11.5Hz)/4.56(m), carbon signals corresponding to hydrogen signals are connected through HSQC, and the corresponding carbon signals are determined. According to literature comparisons, from the sugars1H and13the C NMR data was determined to be β -D-glucopyranose. In HMBC, δ 4.97(d, J ═ 7.7Hz, glc H-1') is associated with δ 089.52(C-3), so the sugar is linked to C-3. Determining carbon signals adjacent to proton signals on the araloside A through HMBC, wherein the carbon signals are delta 22.01(s,3H, H-23) related to delta 189.52(C-3), 17.04(C-24) and 40.29(C-4) respectively; δ 30.93(s,3H, H-25) is related to δ 461.37(C-5), 38.99 (C-10); delta 51.13(s,3H, H-26) is related to delta 647.17(C-7), 42.71 (C-8); delta 71.67(s,3H, H-27) is related to Delta 840.96(C-13), 42.81 (C-14). δ 91.26(d, J ═ 6.2Hz, H-30) is related to δ 157.18(C-20), since δ,157.18 and δ,106.06 are terminal double bond signals. Whereas δ,4.85(d, J ═ 6.2Hz, H-21) correlates with δ,106.06(C-29), thus determining the C-21 signal. δ 4.85(d, J ═ 6.2Hz, H-21) is related to δ 54.43(C-17) and δ 98.13(C-28), thus identifying the signals for C-17, 21, 22 and 28, which form a cyclic structure. The aglycone of aralia elata saponin A is an aglycone and is named aralia elata aglycone (echinocaulis aglycone). Therefore, the structure of the aralia elate saponin A is aralia elate aglycone-3-O-delta 0-D-glucopyranose (echinocaulis aglycone 3-O-delta 1-D-glucopyranoside), and the compound is not reported in the literature and is named as aralia elate saponin A (echinocaulis aponin A) with the chemical structural formula: where (o) indicates overlap with other peaks.
Figure GDA0003324398810000051
Figure GDA0003324398810000052
Figure GDA0003324398810000061
TABLE 1 Elaeagnus ampelina 13C-NMR and 1H-NMR data
Secondly, research on in-vitro antioxidation:
evaluation of in vitro antioxidant Activity of Kalopanax septemlobus Saponin A
1. Experimental materials and instruments:
sample preparation: aralia elata seem saponin A
Rutin standard (CAS #160-16-8, HPLC > 98%), DPPH, sodium hydroxide, sodium nitrite, aluminum nitrate, disodium EDTA, 3% hydrogen peroxide: beijing Biochemical Agents Inc.; absolute ethyl alcohol, ferrous ammonium sulfate hexahydrate: beijing, general Fine chemical company; vitamin C: fuji and photic pure leaf plant type; DNA extraction kit (GD3121-1250 preps): BIOMIGA; microplate reader FlexStation 3: molecular Devices.
2. Experimental methods and results:
2.1 scavenging ability for DPPH free radical
And evaluating the in-vitro antioxidant capacity of the sample by adopting a DPPH free radical scavenging model. Taking a 96-well plate, adding 100 mu L of sample solutions with different concentrations into a sample well, and then adding 100 mu L of 2X 10-7mol/mL DPPH solution; respectively adding 100 mu L of sample solution and 100 mu L of absolute ethyl alcohol with different concentrations into the ginseng sample holes; adding DPPH solution 100 μ L and distilled water 100 μ L into control well, mixing, standing at room temperature in dark place for 30min, measuring absorbance at 517nm, and expressing oxidation resistance with half inhibition ratio IC50 using Vc as control.
And evaluating the antioxidant capacity of the aralia elata seem saponin A by adopting a DPPH free radical scavenging model. Wherein, the calculation formula of the DPPH free radical clearance rate is as follows:
DPPH radical clearance rate ═ 1- (A)i-Aj)/A0]×100％。
Wherein A isiTo add the absorbance of the reaction solution of a certain concentration of the extract, AjIs the background absorbance of the extract at the measured wavelength, A0As a negative control, i.e. reaction without addition of extractAbsorbance of the solution.
The results show that (table 2) the apocynin A of the sample has different degrees of scavenging capacity on DPPH free radicals, and the scavenging rate is enhanced along with the increase of the concentration of the solution. The clearance rate range of the aralia elata glauca saponin A is 35.62-92.16%, and the IC50 is 0.1985 mg/mL.
Figure GDA0003324398810000071
TABLE 2 Elaeagnus ampelopsis for DPPH radical scavenging ability
2.2 protective Effect against OH-induced oxidative damage to DNA
1 μ L of 100ng/μ L DNA, 10 μ L of 0.1mol/L (NH4)2Fe (SO4)2 solution, 10 μ L of 0.17mol/L EDTA disodium solution, 10 μ L of 0.015% H2O2 solution, 10 μ L of 10mg/mL Vc solution, 10 μ L of sample solutions with different concentrations and 40 μ L of TE buffer solution are sequentially added into a 96-well plate, 0.5 μ L of Goldview dye is finally added, the mixture is gently shaken and kept still for reaction for 5min, and the fluorescence intensity of the mixture is measured by using vitamin C as a control (the fluorescence measurement condition is that the fluorescence intensity in the range of 500-695 nm is scanned at 486nm of excitation wavelength).
The results show that (table 3) the aralia elata saponin A has different degrees of protection effects on OH-induced DNA oxidative damage, and the effect is enhanced along with the increase of the solution concentration. The fluorescence intensity range of the aralia elata seem saponin A is 0.358-0.496.
Figure GDA0003324398810000081
TABLE 3 protective effect of aralia elata seem saponin A and aralia elata seem saponin C on OH-induced DNA oxidative damage.
2.3 protective action against H2O 2-induced DNA oxidative damage
Adding 1 mu L of 100 ng/mu L DNA solution, 10 mu L of 3% H2O2 solution, 5 mu L of sample solution, 95 mu LTE buffer solution and 0.5 mu L of Goldview solution into a 96-well plate in sequence, shaking up the solution gently, standing the solution for reaction for 10min, placing a sample-containing cuvette under an ultraviolet lamp for irradiation for 10min, and measuring the fluorescence intensity of the sample-containing cuvette by taking vitamin C as a reference (the fluorescence measurement condition is that the fluorescence intensity in the range of 500-695 nm is scanned under the excitation wavelength of 486 nm).
The results show that (table 4) the apocynin A of the sample has different degrees of protection effects on H2O 2-induced DNA oxidative damage, and the effect is enhanced along with the increase of the solution concentration. The fluorescence intensity range of the aralia elata seem saponin A is 0.335-0.465.
Figure GDA0003324398810000082
Table 4 protective effect of araloside a on H2O 2-induced DNA oxidative damage.
The invention separates and prepares a monomer compound from the medicinal plant aralia elata seem for the first time, and researches the in-vitro antioxidation effect of the monomer compound, thereby providing reliable experimental data support and theoretical basis for the treatment effect of the aralia elata seem related to treating related diseases (cardiovascular diseases, arthritis, age-related macular degeneration and the like) through antioxidation or free radical quenching functions.
The embodiments are described in a progressive manner in the specification, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (5)

1. The preparation method of the aralia elata seem saponin A which is a monomeric compound is characterized by comprising the following steps:
heating and reflux-extracting radix Et caulis Opuntiae Dillenii root bark 2.0kg with 70% ethanol for 3 times, adding 7L ethanol each time, heating for 2h, rotary evaporating to obtain 400mL extract, diluting 200mL extract with 10% ethanol to obtain 2.5L solution, passing through MCI-GEL macroporous resin, gradient eluting with ethanol-water according to 10%, 30%, 50%, 70%, and 90% ethanol, collecting each eluate, recovering solvent, and vacuum drying at low temperature to obtain 9 samples, which are respectively 10% ethanol Fr.1-4, 10% ethanol Fr.5-9, 30% ethanol Fr.1-3, 30% -50% ethanol Fr.3-4, 50% ethanol Fr.1, 50% ethanol Fr.2-3, 70% ethanol Fr.1, 70% ethanol Fr.2-4, and 90% ethanol Fr.1-3, and detecting by thin layer chromatography;
dissolving 50% ethanol Fr.1 part 13.00g in methanol, mixing with 30g silica gel, and dry packing with 4L column volume in CH2Cl2∶MeOH∶H2Gradient elution with O75: 20: 5, 70: 22: 5, 75: 25: 5, 70: 26: 5, 65: 25: 5, 70: 43: 10, and thin layer chromatography for mixing and concentrating to obtain 12 parts Fr.F1-12; f4 part 190mg was taken, dissolved in a solution of acetonitrile/water 28: 72, filtered and prepared via preparative liquid phase, mobile phase ratio: acetonitrile and water are 28: 72, thus obtaining the araloside A10 mg; . The chemical structural formula of the aralia elata seem saponin A is as follows:
Figure FDA0003324398800000011
。
2. the monomeric compound apocynin A of claim 1, wherein the acetonitrile to water is 28 to 72 solution, and the water contains 0.01% formic acid.
3. The in vitro antioxidant effect of the monomeric compound apothecin A according to claim 2, wherein the apothecin A has a certain DPPH free radical scavenging ability.
4. The in vitro antioxidant effect of a monomeric compound apothecin A according to claim 2, wherein the apothecin A has a protective effect on OH-induced DNA oxidative damage.
5. The in vitro antioxidant effect of apothecin A as a monomer compound of claim 2, wherein the apothecin A has H pair2O2The induced DNA oxidative damage has protective effect.
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