CN110548055A - Fresh and fragrant celery leaf water extract powder, preparation, vasodilatation effect and application thereof - Google Patents
Fresh and fragrant celery leaf water extract powder, preparation, vasodilatation effect and application thereof Download PDFInfo
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- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
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Abstract
The invention discloses a method for preparing fresh parsley leaf water extract powder, discloses structures of 38 new components in the fresh parsley leaf water extract powder, namely structures of 2 new cane sugars, structures of 22 new quinic acids and structures of 14 new apiosides, and further discloses vasodilatation of the fresh parsley leaf water extract powder, so that the invention discloses application of the fresh parsley leaf water extract powder in preparation of a blood vessel relaxing medicine.
Description
Technical Field
The invention relates to a method for preparing powder from an aqueous extract of fresh parsley green, which relates to the reproducibility of a process for preparing the powder from the aqueous extract of the fresh parsley green, which is defined by a characteristic UPLC-mass spectrum total ion current spectrum and 38 peaks thereof, relates to components in the powder, which are defined by the characteristic UPLC-mass spectrum total ion current spectrum and 38 peaks thereof, relates to the structures of 2 new sucrose analogs corresponding to the 38 peaks, relates to the structures of 22 new quinic acid analogs, relates to the structures of 14 new apioside analogs, and further relates to the vasodilation effect of the aqueous extract powder of the fresh parsley green, so the invention relates to the application of the aqueous extract powder of the fresh parsley green in preparing vasodilation medicines. The invention belongs to the field of biological medicine.
Background
a large body of statistical data suggests that vasoconstriction is closely related to aging, atherosclerosis and ischemia reperfusion. Effective prevention of vasoconstriction has become a health concern worldwide. Although some vitamins and traditional Chinese medicines have vasodilating effect, the long-term taking of the vitamin and traditional Chinese medicines as preventive medicines still has uncertainty. The discovery of the medicine which can be used for preventing vasoconstriction without any toxic and side effect is an important direction for medicine research.
the folk always has a theory of cool nature and taste of the celery leaves, and the celery leaves are considered to have the effects of clearing heat and disinfecting, treating the exuberant liver fire and calming the liver and clearing heat. In folk, vegetable leaves are rich in cellulose, so that the theory of relaxing bowels and treating constipation is provided. In folks, celery leaves are also thought to have the effect of lowering blood pressure and also can treat dizziness, edema and irregular menstruation. Without rigorous pharmacodynamic studies, the basis of these statements is only experience. Furthermore, whether celery leaves in these parnassia are celery leaves or parsley leaves is not defined. Further, these statements are not directly related to vasodilation. In addition, the inventor proposes the liver protection effect of the fresh celery leaf nano juice. However, the fresh celery leaf nano juice is not only mildewed but also precipitated after being placed for 20 days. Mildew may cause disease and precipitation may alter chemical composition. These two fatal problems caused the inventors to abandon the subsequent development of the fresh celery leaf nano-juice.
The inventor researches the chemical components and the treatment effect of the fresh and fragrant celery leaf water extract powder for a long time. The inventors have recognized that it is not clear to the skilled artisan which chemical components are contained in the aqueous extract of celeriac, nor is it clear what the therapeutic effect of the aqueous extract of celeriac. In response to this situation, the inventors performed mass spectrometry on an aqueous extract of fresh parsley leaf. Analysis of 38 components in the aqueous extract of fresh celery leaves led the inventors to realise that the aqueous extract of fresh celery leaves prevents vasoconstriction. The structural analysis of 38 components in the water extract of the fresh celery leaves leads to the discovery of 38 new compounds, thereby embodying the intelligence and creativity of the invention. Compared with all celery related known inventions, the fresh fragrant celery leaf water extract powder reaches a brand new height. Based on these findings, the inventors have proposed the present invention.
Disclosure of Invention
The first content of the invention is a method for providing fresh celery leaf aqueous extract powder, which comprises the following steps:
(1) Washing 1000g of fresh celery leaves without silt on the surface with 3000mL of tap water for 2 times, then transferring to a sterile environment, washing with 3000mL of triple-distilled water for 3 times, and filtering water to obtain clean fresh celery leaves;
(2) soaking clean fresh celery leaves in triple-distilled water at 60-90 ℃ for 3 times, soaking in 3000mL of triple-distilled water for at least 30 minutes each time, and slowly stirring during soaking;
(3) After each soaking, the water extract flows out slowly and automatically, and the time for use is not less than 30 minutes;
(4) And concentrating the obtained 9000mL of water extract at 60-90 ℃ under reduced pressure to obtain 24g of fresh celery leaf water extract powder.
The second content of the invention is to provide the ultraviolet spectrum of the fresh celery leaf water extract powder.
The third content of the invention is to provide a mass spectrum total ion current spectrum of the fresh celery leaf water extract powder.
the fourth aspect of the invention is to provide the chemical structures of the 38 components corresponding to the peaks in the mass spectrum total ion flow spectrum of the fresh parsley leaf aqueous extract powder.
The fifth content of the invention is to describe the therapeutic effect of the fresh celery leaf water extract powder on vasoconstriction.
drawings
FIG. 1 UPLC chromatogram of fresh celery leaf water extract powder.
FIG. 2. UPLC-mass spectrum of total ion current of fresh parsley leaf extract powder.
FIG. 3 is a mass spectrum of 6-O- [ E-2, 6-dihydroxy-2, 5-di- (2, 4-hexadienoyloxy) -4- (1, 3-butadienoyloxy) cinnamoyl ] sucrose.
FIG. 4 shows the cleavage pathway of 6-O- [ E-2, 6-dihydroxy-2, 5-di- (2, 4-hexadienoyloxy) -4- (1, 3-butadienoyloxy) cinnamoyl ] sucrose.
FIG. 5 is a mass spectrum of 3-O- [ E-2-hydroxy-6-acetoxy-3, 5-bis (carboxybutadienylcarbonyloxy) -4- (carboxy-n-acryloyloxy) cinnamoyl ] quinic acid.
FIG. 6 shows the cleavage pathway of 3-O- [ E-2-hydroxy-6-acetoxy-3, 5-bis (carboxybutadienylcarbonyloxy) -4- (carboxy n-acryloyloxy) cinnamoyl ] quinic acid.
FIG. 7.mass spectrum of 3-hydroxy-4- (n-propylcarbonyloxy) apigenin.
FIG. 8.3-hydroxy-4- (n-propylcarbonyloxy) apigenin cleavage pathway.
Detailed Description
To further illustrate the invention, a series of examples are given below. These examples are purely illustrative and are intended to be a detailed description of the invention only and should not be taken as limiting the invention.
Example 1 preparation of an aqueous extract powder of fresh parsley leaf
1000g of fresh celery leaves without silt on the surface are washed with 3000mL of tap water for 2 times, and then transferred to a sterile environment and washed with 3000mL of triple-distilled water for 3 times. Filtering off water to obtain clean fresh celery leaves. Soaking clean fresh celery leaves in triple-distilled water at 60-90 ℃ for 3 times, soaking in 3000mL of triple-distilled water for at least 30 minutes each time, and slowly stirring during soaking. After each soaking, the water extract is allowed to slowly flow out by itself for no less than 30 minutes. About 9000mL of the slowly flowing aqueous extracts were combined and concentrated at 60 ℃ -90 ℃ under reduced pressure to obtain 24g of powder of the fresh parsley leaf aqueous extract.
Example 2 determination of chromatography and Mass Spectrometry ion Spectroscopy of fresh celery leaf aqueous extract powder
2-1 preparation of sample solution (10mg/mL)
26.7mg of the water extract powder of fresh and fragrant celery leaves was weighed out and dissolved in 2.67mL of ultrapure water. The resulting solution was sonicated for 1 minute and then centrifuged at 13000r/min for 10 minutes. The supernatant was taken, filtered through a 0.22 μm filter and placed in a sample vial for chromatographic and mass spectrometric determination.
2-2. chromatographic conditions
Chromatographic column Waters, AcquityA HSS T3 column (2.1 × 100mm i.d.,1.8 μm);
The sample injection volume is 2 mu L;
PDA detector 210-400 nm;
Mobile phase water (0.1% formic acid), acetonitrile;
the mobile phase washed the column according to the gradient of table 1.
TABLE 1 mobile phase gradiometer
2-3 measuring chromatogram
UPLC chromatogram of the fresh celery leaf aqueous extract powder was determined and recorded according to the above chromatographic determination conditions (see the attached figure 1 of the specification).
2-4. conditions for measuring ion flow spectrum and mass spectrum
Electrospray ionization mode, Positive (PI) and Negative (NI) modes;
the collision energy of the inclined trap is 20-60V;
Cone current 40V;
The temperature of the ion source is 100 ℃;
The capillary voltage is 30 kV;
Spraying pressure is 6.5 bar;
the m/z range is 100-1500.
2-5, recording ion flow spectrum and mass spectrum
ion flow spectrum and mass spectrum of the fresh celery leaf water extract powder are measured and recorded according to the above conditions (see the attached figures 2 and 3-38 of the specification).
Example 3 assignment of the Structure of 38 Components in an aqueous extract powder of fresh parsley leaf
the UPLC chromatogram of example 2 was coupled to a mass spectrum and the UPLC-mass spectrum of the fresh parsley leaf aqueous extract powder was determined. Mass spectrometry conditions are two modes of electrospray ionization Positive Ion (PI) and Negative Ion (NI). The slant trap collision energy (ramp trap collision energy) is 20-60V. The cone voltage (cone voltage) was 40V. The ion source temperature was 100 ℃. The capillary voltage was 30 kV. The pressure of the nebulizer (nebulizerpressure) was 6.5 bar. The mass/charge ratio (m/z range) is 100-1500. 34 independent peaks separated within 14 minutes. According to the mass spectrometry fragmentation law, the peaks (numbered sequentially from left to right for the peaks of the total ion current spectrum) are assigned to the corresponding components of table 2.
TABLE 2 component names corresponding to peaks of the Total ion flux map
Example 4 chemical Structure, Mass Spectrometry and lysis Process of 34 Components in fresh celery leaf aqueous extract powder
The molecular ions and the fragment ions were correlated with each other on the basis of the mass spectrum corresponding to each peak in the total ion current measured in analytical example 2. Thus, the process is completed. The inventors established the cleavage pathway of the 38 components in table 2 of example 3 under the mass spectrometric conditions. After the confirmation of these cleavage pathways, it is in turn the basis for the discovery of the invention that 38 components in the water extract powder of fresh celery leaves have undisputed novelty and inventiveness. As representative examples, FIG. 3 shows a mass spectrum of 6-O- [ E-2, 6-dihydroxy-2, 5-bis- (2, 4-hexadienoyloxy) -4- (1, 3-butadienoyloxy) cinnamoyl ] sucrose, FIG. 4 shows a cleavage pathway of 6-O- [ E-2, 6-dihydroxy-2, 5-bis- (2, 4-hexadienoyloxy) -4- (1, 3-butadienoyloxy) cinnamoyl ] sucrose, FIG. 5 shows a mass spectrum of 3-O- [ E-2-hydroxy-6-acetyloxy-3, 5-bis (carboxybutadienoyloxy) -4- (carboxy n-acryloyloxy) cinnamoyl ] quinic acid, FIG. 6 shows 3-O- [ E-2-hydroxy-6-acetyloxy-3, the cleavage pathway of 5-bis (carboxybutadienecarbonyloxy) -4- (carboxy n-acryloyloxy) cinnamoyl ] quinic acid, FIG. 7 is 3-hydroxy
mass spectrum of-4- (n-propylcarbonyloxy) apigenin, and figure 8 is a cleavage pathway of 3-hydroxy-4- (n-propylcarbonyloxy) apigenin.
Example 5 measurement of vasodilation Effect of fresh parsley leaf Water extract powder
Since noradrenaline is generally known as a vasoconstrictor and acetylcholine is generally known as a vasodilator, the antagonism of the noradrenaline-induced thoracic aortic ring contraction in rats by the fresh celery leaf extract powder is measured on a noradrenaline-induced thoracic aortic ring contraction model in rats. Acetylcholine is a positive control for the present invention.
Rats anesthetized with ether were sacrificed by cervical dislocation, the thoracic aorta was removed by opening the thoracic cavity and cut into a 2mm long loop. The prepared thoracic aorta ring of the rat is placed in a K-H buffer solution and aerated to keep the activity. Starting a physiological two-channel instrument (the running software is M3000), starting circulating water of the breeding tank, injecting K-H buffer solution into the breeding tank and introducing oxygen. The tension transducer is set and calibrated. The rat thoracic aorta was looped over a tension transducer, placed in a rearing trough and tension monitored. After the tonicity stabilized, 20. mu.L of noradrenaline aqueous solution was added to make its concentration in the incubator 20. mu.g/mL. Monitoring the tension, after the tension is stabilized, injecting an aqueous solution of the fresh celery leaf water extract powder (the concentration is 50 mu g/mL,100 mu g/mL,150 mu g/mL and 200 mu g/mL) or an acetylcholine aqueous solution (the concentration is 2 mu g/mL) into the breeding tank, and recording the tension after the tension is stabilized. And calculating the tension difference between the water solution of the fresh fragrant celery leaf water extract powder and the acetylcholine water solution before and after injection. The percentage of the difference value and the tension of the aqueous solution of the fresh parsley leaf water extract powder or the acetylcholine aqueous solution before injection is the relaxation rate. The results are shown in Table 3.
TABLE 3 vasodilation of the fresh parsley leaf aqueous extract powder
a) The concentration group ratio p of 120 mu g/mL,80 mu g/mL and 40 mu g/mL is less than 0.01, and the ratio p of acetylcholine is more than 0.05; b) the ratio p to the concentrations of 80 mug/mL and 40 mug/mL is less than 0.01; c) p <0.01 to a concentration of 40 μ g/mL; n is 3, and the experimental data statistics adopt t test.
The data in Table 3 illustrate that aqueous solutions of the fresh parsley leaf aqueous extract powder at concentrations of 40. mu.g/mL, 80. mu.g/mL, 120. mu.g/mL, and 160. mu.g/mL, concentration-dependently antagonize norepinephrine-induced vasoconstriction. The effect peaked at a concentration of 160. mu.g/mL and was not different from acetylcholine. Different from the blood vessel relaxing medicine applied clinically, the fresh and fragrant celery leaves are vegetables. As a vegetable which can be eaten at will, the fresh and fragrant celery leaf water extract powder has an unexpected technical effect of blood vessel relaxing effect.
Claims (6)
1. the fresh fragrant celery leaf water extract powder is characterized in that the powder is composed of 38 new compounds which are 2 kinds of sucrose, 22 kinds of quinic acid and 14 kinds of apigenin.
2. The fresh parsley leaf aqueous extract powder of claim 1, characterized in that the 2 sucrose are 6-O- [ E-2, 6-dihydroxy-2, 5-bis- (2, 4-hexadienocarbonyloxy) -4- (1, 3-butadiene-carbonyloxy) cinnamoyl ] sucrose and 6-O- [ E-3-hydroxy-4-acryloyloxy-5- (2-butenyloxy) cinnamoyl ] sucrose.
3. the fresh parsley leaf aqueous extract powder of claim 1, wherein the 22 kinds of quinic acids are respectively 3-O- [ E-2, 6-dihydroxy-3, 5-di (carboxy n-butyldienoyloxy) -4- (hydroxy n-butyldienoyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-dihydroxy-3, 4, 5-tri (acryloyloxy) cinnamoyl ] quinic acid, 3-O- [ E-3, 5-di (carboxy n-butyldienoyloxy) -4- (carbonyl n-butyldienoyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-dihydroxy-3, 5-di (carboxy n-butyldienoyloxy) -4- (carboxyacryloyloxy) cinnamoyl ] quinic acid, 3-O- [ E-3, 5-bis (carboxypropenoyloxy) -4- (carboxyn-butyldienoyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2-hydroxy-3, 5-bis (carboxypropenoyloxy) -4- (carboxyacetoxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-dihydroxy-3, 5-bis (carboxy-n-propylcarbonyloxy) -4- (hydroxy-n-propylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-3, 5-bis (carboxy-n-butyldienoyloxy) -4- (carboxyacetoxy) cinnamoyl ] quinic acid, 3-O- [ E-2-hydroxy-3, 5-bis (carboxy-n-butylcarbonyloxy) -4- (hydroxy-n-butylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-dihydroxy-3, 5-di (carboxy n-propylcarbonyloxy) -4- (hydroxy n-propylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-dihydroxy-3, 5-di (carboxybutadienylcarbonyloxy) -4- (carboxy-2-butenyloxy) cinnamoyl ] quinic acid, 3-O- [ E-3, 5-di (carboxybutadienylcarbonyloxy) -4- (carboxy-3, 5-hexadienylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2-hydroxy-6-acetoxy-3, 5-di (carboxybutadienylcarbonyloxy) -4- (carboxy n-propyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-bis (carboxy-n-acryloyloxy) -3-formyloxy-4, 5-bis (carboxyacetoxy) cinnamoyl ] quinic acid, 3-O- [ E-3- (carboxy-n-butyldienylcarbonyloxy) -4- (carboxyacetoxy) -5- (carboxy-3-n-butenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2-hydroxy-3, 5-bis (carboxy-n-butyldienylcarbonyloxy) -4- (carboxy-n-butylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2-hydroxy-3, 5-bis (carboxy-n-acryloyloxy) -4- (hydroxymethyl) cinnamoyl ] quinic acid, 3-O- [ E-3- (hydroxy-n-propylcarbonyloxy) -4- (acryloyloxy) -5- (formyl-1, 3-butadiene carbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-3- (carboxy-3-n-butenylcarbonyloxy) -4- (carboxy n-butylcarbonyloxy) -5- (hydroxy-4-n-pentenylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2-hydroxy-3, 4-bis (hydroxy n-propylcarbonyloxy) -5- (carboxypropylcarbonyloxy) cinnamoyl ] quinic acid, 3-O- [ E-2, 6-dihydroxy-3, 4, 5-tris (hydroxy n-propylcarbonyloxy) cinnamoyl ] quinic acid and 3-O- [ E-3, 5-bis (hydroxy n-propylcarbonyloxy) -4- (hydroxypropionyloxy) cinnamoyl ] quinic acid.
4. The fresh parsley leaf aqueous extract powder of claim 1, wherein 14 kinds of apigenin are 2, 6-dihydroxy-3, 4-di (n-undecyloxycarbonyloxy) -5- (n-undecyloxycarbonyloxy) apigenin, 3, 4-di (n-butylcarbonyloxy) apigenin, 3- (7-n-heptenecarbonyloxy) -4- (n-hexylcarbonyloxy) apigenin, 2, 6-dihydroxy-3, 4-di (9-n-decaenecarbonyloxy) -5- (n-undecyloxycarbonyloxy) apigenin, 3- (acryloyloxy) -4- (hydroxymethyl oxy) apigenin, 3-hydroxy-4- (n-propylcarbonyloxy) apigenin, 3-formyloxy-4-acetoxyapigenin, 3, 5-di (acetyloxy) -4- (n-acryloylcarbonyloxy) apigenin, api, 3- (3,5,7, 9-decatetraenyloxy) -4- (1,3,5,7, 9-decapentaenyloxy) apigenin, 3-acetoxy-4-hydroxyapigenin, 3, 4-di (n-butyldienoyloxy) apigenin, 3- (3, 4-pentadienoyloxy) -4- (1,3, 5-n-hexatrienylcarbonyloxy) apigenin, 3- (3,5, 7-n-heptatrienylcarbonyloxy) -4- (3, 5-n-hexadienoyloxy) apigenin, and 4- (4-n-pentenoyloxy) apigenin.
5. A process for preparing an aqueous extract powder of freshly flavored celery leaves according to claim 1, which process comprises the steps of:
(1) Washing 1000g of fresh celery leaves without silt on the surface with 3000mL of tap water for 2 times, then transferring to a sterile environment, washing with 3000mL of triple-distilled water for 3 times, and filtering water to obtain clean fresh celery leaves;
(2) Soaking clean fresh celery leaves in triple-distilled water at 60-90 ℃ for 3 times, soaking in 3000mL of triple-distilled water for at least 30 minutes each time, and slowly stirring during soaking;
(3) After each soaking, the water extract flows out slowly and automatically, and the time for use is not less than 30 minutes;
(4) Concentrating the obtained 9000mL of aqueous extract at 60-90 deg.C under reduced pressure to obtain about 24g of powder of fresh parsley leaf aqueous extract;
(5) The components contained in the aqueous extract powder are defined by its characteristic UPLC-mass spectrometry total ion current spectrum and 38 peaks therein, and the mass of the aqueous extract powder is also defined by its characteristic UPLC-mass spectrometry total ion current spectrum and 38 peaks therein.
6. Use of the fresh parsley leaf aqueous extract powder of claim 1 for the preparation of a vasodilator.
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| CN110713507A (en) * | 2018-07-12 | 2020-01-21 | 北京恒润泰生医药科技有限公司 | Water extract powder of fresh celery leaf, its preparation, free radical scavenging action and application |
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| CN102228223A (en) * | 2011-06-02 | 2011-11-02 | 张天立 | Plant salt and preparation method thereof |
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| CN110713507A (en) * | 2018-07-12 | 2020-01-21 | 北京恒润泰生医药科技有限公司 | Water extract powder of fresh celery leaf, its preparation, free radical scavenging action and application |
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Application publication date: 20191210 |