CN103142689A - Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as free-radical scavenger - Google Patents
Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as free-radical scavenger Download PDFInfo
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Abstract
The invention relates to rabdosia rubescens stem aqueous extract and its preparation method and finger-prints, wherein the rabdosia rubescens stem aqueous extract is extracted from rabdosia rubescens stems by distilled water at a temperature of 80DEG C and the finger-prints comprise a HPLC-(-)ESI-Q-TOF-MS/MS finger-print and a HPLC-(+)ESI-Q-TOF-MS/MS finger-print. The invention also relates to a use of the rabdosia rubescens stem aqueous extract as a free-radical scavenger.
Description
Invention field
The present invention relates to the Rabdosia rubescens stem with 80 ℃ of distilled water extract the preparation water extracts, relate to this water extract HPLC-(-) ESI-Q-TOF-MS/MS finger printing, relate to this water extract HPLC-(+) ESI-Q-TOF-MS/MS finger printing, further relate to this water extract as the application of free radical scavenger.The invention belongs to biomedicine field.
Background technology
Radiation, pesticide, food additive, ethanol, smoking, metabolism, anoxia and fierce motion all can make human body produce free radical.Free radical in human body mainly contains oxygen-derived free radicals, hydroxy radical and NO free radical.Free radical can cause various diseases.for example but free radical damaging cells film causes the cell membrane degeneration, can cause gene mutation to bring out cancer, but activating immune system causes the autoimmune diseases such as lupus erythematosus, capillary fragility be can increase and varicosis and edema caused, can excite various inflammatory factors to discharge and cause the non-bacterial inflammation, can damage brain cell and cause alzheimer, oxidable blood lipoprotein cause cholesterol to blood vessel wall deposition cause arteriosclerosis and and apoplexy, can cause that the degraded of membrana articulata and knuckle synovia causes arthritis and can damage the pancreas cell causing the diseases such as diabetes.Seeking free radical scavenger is one of important directions of drug research.
Rabdosia rubescens (DLC) is the crack rice herb of fork Rabdosia rubescens (Hemsl.) Hara of Labiatae Rabdosia plant.Rabdosia rubescens is herbaceos perennial, is distributed widely in the Yangtze river basin, China the Yellow River, main product in the Jiyuan, Henan Taihang Mountain, Wangwu Shan Mountain district one band.Because having heat-clearing and toxic substances removing, pharynx-clearing throat-benefiting and a reducing swelling and alleviating pain function, among the peoplely the Rabdosia rubescens leaf is used as that Folium Camelliae sinensis is to boil water to be drunk throughout the year.In in the past more than 30 year, the chemical composition of Rabdosia rubescens and pharmacological research mainly concentrate on the fatty contents of leaf, and representative composition is rubescensine A and rubescensine B.Although once someone studied the free radical scavenging activity of rubescensine A, be seen in document without any the research relevant to the water extract chemical composition of Rabdosia rubescens stem and free radical scavenging effect so far.Compare with leaf, Rabdosia rubescens stem shared ratio in herb is high a lot.Effectively using Rabdosia rubescens stem protection human body, to avoid radical damage significant.
By long-term free radical scavenger research accumulation, the inventor locks phenolic acid and diterpene is the structure type with free radical scavenging activity.Predict by the Analyzing Source of Students inventor and contain abundant phenolic acid and diterpene in the Rabdosia rubescens stem.According to these understanding, the inventor proposes the present invention, discloses the chemical composition of Rabdosia rubescens stem water extract, the free radical scavenging effect that discloses Rabdosia rubescens stem water extract with the free radical scavenging model with HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS fingerprint collection of illustrative plates.
Summary of the invention
First technical problem to be solved by this invention is to provide a kind of method for preparing Rabdosia rubescens stem water extract.
Second technical problem to be solved by this invention is to set up HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS analytical method, obtains the finger printing of Rabdosia rubescens stem water extract in order to control the quality of Rabdosia rubescens stem water extract.
The 3rd technical problem to be solved by this invention be use by base remove model evaluation Rabdosia rubescens stem water extract by basic scavenging action, removing by base the disease that causes for prevention provides Rabdosia rubescens stem water extract as the high material that has no side effect of free radical scavenging activity.
The present invention relates to the preparation technology of Rabdosia rubescens stem water extract, this technique comprise the Rabdosia rubescens stem with hot water extraction, water extract filter, filtrate decompression be concentrated into dried, the dry powder that obtains with HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS analyze finger printing, the dry powder that obtains use by base removing model evaluation Rabdosia rubescens stem water extract by basic scavenging action.
In order further to set forth the present invention, the below provides a series of embodiment.These embodiment are illustrative fully, and they only are used for the present invention is specifically described, and not should be understood to limitation of the present invention.
Description of drawings
The ion flow finger printing that Fig. 1 a Rabdosia rubescens stem water extract detects at (-) ESI-Q-TOF-MS
The ion flow finger printing that Fig. 1 b Rabdosia rubescens stem water extract detects at (+) ESI-Q-TOF-MS
Fig. 2 a, b Rabdosia rubescens stem water extract is removed the effect of DPPH free radical
Fig. 3 a, b Rabdosia rubescens stem water extract is removed the effect of hydroxy radical
The specific embodiment
The preparation of embodiment 1 Rabdosia rubescens stem water extract
The dried Rabdosia rubescens stem of 40g tap water is cleaned, airing, to be cut into the long stem section of about 1cm, to add the 1000-1800mL temperature be the hot distilled water diafiltration of 70-90 ℃, preferably adds the 1200mL temperature and be the hot distilled water diafiltration of 80 ℃.The speed that percolate flows out is 10-30mL/ minute, preferred 20mL/ minute.Effluent is preferable over 50 ℃ of concentrating under reduced pressure in 40-60 ℃ of concentrating under reduced pressure, obtains 3g Rabdosia rubescens stem water extract, is faint yellow solid.Pulverize is for the research of back.
HPLC-(-) the ESI-Q-TOF-MS/MS finger printing of embodiment 2 Rabdosia rubescens stem water extracts and HPLC-(+) ESI-Q-TOF-MS/MS finger printing
HPLC：Waters?2795Separations?Module；
Detector：Waters?2489Dual?absorbance?detector；
Kromasil C
18(Dikma) reversed-phase column (5_ μ m, 250_mm_ * _ 4.6_mm);
Guard column (5_ μ m, 10_mm_ * _ 4.6_mm);
Mobile phase: acetonitrile/water (containing 0.5% and 0.05% glacial acetic acid);
Flow rate of mobile phase: 0.3ml/min;
Sample size: 50 μ L;
Type of elution: gradient elution (concrete gradient sees Table 1).
Table 1 Rabdosia rubescens stem water extract HPLC-analyzes the eluent gradient table
a
aThe A=acetonitrile, (contain 0.05% glacial acetic acid, v/v), C=water (contains 0.5% glacial acetic acid, v/v) to B=water
The ion flow finger printing of Rabdosia rubescens stem water extract under HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS detection: Fig. 1 a and Fig. 1 b once analyze 22 peaks;
(-) ESI-Q-TOF-MS ion flow finger printing of embodiment 3 Rabdosia rubescens stem water extracts
(-) ESI-Q-TOF-MS: adopt one to optimize good small molecule analysis method, design parameter is a) Source Type:ESI; B) Ion Polarity:Negative; C) Scan begin:50m/z; D) Scan begin:1500m/z; E) Set Capillary:3500V; F) Set Nebulizer:0.8Bar; G) Set Dry Heater:200 ℃; H) Set Dry Gas:8.0ml/min; I) Funnel 1RF:300Vpp; J) Funnel 2RF:300Vpp; K) ISCID Energy:0eV; L) Hexapole RF:200Vpp; M) Ion Energy:5eV; N) Low Mass:200m/z; O) Collision Energy:14eV; P) Collision RF:140Vpp; Q) Transfer Time:110.8 μ S; R) Pre Puls Storage:8.7 μ S; S) Source:1400v, 2nA; T) adopt sodium formate that mass spectrograph is proofreaied and correct before each the analysis.
Use high-efficient liquid phase chromatogram condition and the good mass spectrum condition of system optimization of having groped, adopting negative ion mode is that (-) ESI carries out (-) ESI-Q-TOF-MS analysis to Rabdosia rubescens stem water extract.Its one-level mass spectrum ion flow is seen Fig. 1 a.Can find out single injected sampling from Fig. 1 a, analysis time, 350min, detected 22 peaks altogether from the one-level mass spectrum.
(+) ESI-Q-TOF-MS ion flow finger printing of embodiment 4 Rabdosia rubescens stem water extracts
(+) ESI-Q-TOF-MS: adopt one to optimize good small molecule analysis method, design parameter is a) Source Type:ESI; B) Ion Polarity:Negative; C) Scan begin:50m/z; D) Scan begin:1500m/z; E) Set Capillary:3500V; F) Set Nebulizer:0.8Bar; G) Set Dry Heater:200 ℃; H) Set Dry Gas:8.0ml/min; I) Funnel 1RF:300Vpp; J) Funnel2RF:300Vpp; K) ISCID Energy:0eV; L) Hexapole RF:200Vpp; M) Ion Energy:5eV; N) Low Mass:200m/z; O) Collision Energy:14eV; P) Collision RF:140Vpp; Q) Transfer Time:110.8 μ S; R) Pre Puls Storage:8.7 μ S; S) Source:1400v, 2nA; T) adopt sodium formate that mass spectrograph is proofreaied and correct before each the analysis.
Use high-efficient liquid phase chromatogram condition and the good mass spectrum condition of system optimization of having groped, adopting positive ion mode is that (+) ESI carries out (+) ESI-Q-TOF-MS analysis to Rabdosia rubescens stem water extract.Its one-level mass spectrum ion flow is seen Fig. 1 b.Can find out single injected sampling from Fig. 1 b, analysis time, 350min, detected 22 peaks equally from the one-level mass spectrum.
Phenolic acid and diterpene in embodiment 5HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS spectrum definition Rabdosia rubescens stem water extract
With the second order ms data of Rabdosia rubescens stem water extract and the second order ms data contrast of standard substance, perhaps with the second order ms data contrast of the compound of bibliographical information, perhaps utilize compound cracking rule to derive, the present invention confirmed corresponding to, the peak 1 of Fig. 1 a, 10,11,14,15 and 17 totally 6 phenolic acid, the peak 16,19,20 and 21 of Fig. 1 b is totally 4 diterpene.
(-) ESI-Q-TOF-MS at peak 1 provides [M-H]
-/ 197 and [2M-H]
-The daughter ion that/395. second order mses provide has [M-H-H
2O]
-/ 179 and [M-H-H
2O-CO
2]
-/ 135.These second order mses with the danshensu standard substance are consistent, and peak 1 is danshensu.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 17 provides [M-H]
-/ 717,, [2M-H]
-/ 1435, [M+H]
+/ 719, [M+Na]
-/ 741, [2M+H]
+/ 1437and[2M+Na]
+/ 1459. second order mses provide m/z 197, [M-H-198]
-/ 519, [M-H-180]
-/ 537, [M-H-180-18-44]
-/ 475, [M-H-198-180]
-/ 339 and [M-H-198-198]
-/ 321 these second order mses with salvianolic acid B are consistent, and peak 17 is salvianolic acid Bs.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 10 provides [M-H]
-/ 537, [2M-H]
-/ 1075, [M+H]
+/ 539 and [M+Na]
+/ 561.Second order ms provides m/z/197, [M-H-44-198]
-/ 295, [M-H-180]
-/ 357, [M-H-44]
-/ 493, [M-H-180-44]
-/ 313 and [M-H-180-44 * 2]
-/ 269.These daughter ions 17 are also observed at the peak.Because the molecular ion at peak 10 and peak 17 differs the mass number of a danshensu residue just, so 5-(2-carboxyvinyl)-2 is appointed as at peak 10,3-dihydro-7-hydroxy-2-(3,4-dihydroxyphenyl) benzofuran-3-carboxylic acid 1-carboxy-2-(3,4-dihydroxyphenyl)-ethyl ester.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 11 provides [M-H]
-/ 537, [2M-H]
-/ 1075, [M+H]
+/ 539 and [M+Na]
+/ 561.Second order ms provides m/z/197, [M-H-44-198]
-/ 295, [M-H-180]
-/ 357, [M-H-44]
-/ 493, [M-H-180-44]
-/ 313 and [M-H-180-44 * 2]
-/ 269.These are consistent with peak 10, and just the retention time of HPLC is different, so the isomer at peak 10 is appointed as at peak 11.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 14 provides [M-H]
-/ 715, [M+H]
+/ 717 and [M+Na]
+/ 739. because the daughter ion m/z/537 that the second order ms at peak 14 provides, m/z/519, m/z/493, m/z/339, m/z/295, m/z/267 lacks 2 with m/z/197 with the consistent just molecular weight of daughter ion that the second order ms of salvianolic acid B provides, so the product that salvianolic acid B takes off a part hydrogen is appointed as at peak 14.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 15 provides [M-H]
-/ 715, [M+H]
+/ 717 and [M+Na]
+/ 739. because the daughter ion m/z/537 that the second order ms at peak 15 provides, m/z/519, and m/z/493, m/z/339, m/z/295, m/z/267 is consistent with peak 14 with m/z/197, and the retention time of HPLC difference just is so the isomer at peak 14 is appointed as at peak 15.
(-) ESI-Q-TOF-MS and (+) ESI-Q-TOF-MS at peak 16 provides [M-H]
-/ 363 and [M+H]
+/ 365.Second order ms provides daughter ion [M-H-H
2O]
-/ 345, [M-H-2H
2O]
-/ 327, [M-H-3H
2O]
-/ 309, [M-H-H
2O-CH
2O]
-/ 315, [M-H-2H
2O-CO
2]
-/ 283, [M-H-2H
2O-CO]
-299 and [M-H-CH
2O-2H
2O]
-/ 297.These ions are consistent with the ion of Amethystonoic acid.Amethystonoicacid is appointed as at peak 16 like this.
(-) ESI-Q-TOF-MS at peak 19 and (+) ESI-Q-TOF-MS provide [M-H]
-/ 363, [2M-H]
-/ 727, [M+H]
+/ 365, [M+Na]
+/ 387, [2M+H]
+/ 729 and [2M+Na]
+/ 751.Second order ms provides daughter ion [M-H-H
2O]
-/ 345, [M-H-CH
2O]
-/ 333, [M-H-2H
2O]
-/ 327, [M-H-CH
2O-H
2O]
-/ 315, [M-H-3H
2O]
-/ 309, [M-H-4H
2O]
-/ 291 and [M-H-CH
2O-2H
2O]
-/ 297.These ions are consistent with the ion of oridonin.Oridonin is appointed as at peak 16 like this.
(-) ESI-Q-TOF-MS at peak 20 and (+) ESI-Q-TOF-MS provide [M-H]
-/ 407, [M+H]
+/ 409, [M+Na]
+/ 431, [2M+H]
+/ 817 and [2M+Na]
+/ 839.Second order ms provides daughter ion [M-H-CH
3CO
2H]
-/ 347, [M-H-CH
3CO
2H-H
2O]
-/ 329, [M-H-CH
3CO
2H-2H
2O]
-/ 311, [M-H-CH
3CO
2H-CH
2O]
-/ 317, [M-H-CH
3CO
2H-CO
2]
-/ 303, [M-H-CH
3CO
2H-CH
2O-H
2O]
-/ 299 and [M-H-CH
3CO
2H-2H
2O-CH
2O]
-/ 281.These ions are consistent with the ion of rabdoternin D.RabdoterninD is appointed as at peak 16 like this.
(-) ESI-Q-TOF-MS at peak 21 and (+) ESI-Q-TOF-MS provide [M-H]
-/ 361, [2M-H]
-/ 723, [M+H]
+/ 363, [M+Na]
+/ 385 and [2M+Na]
+/ 747.Second order ms provides daughter ion [M-H-H
2O]
-/ 343, [M-H-2H
2O]
-/ 325, [M-H-H
2O-CO
2]
-/ 299 and [M-H-H
2O-CO
2-CO]
-/ 271.These ions are consistent with the ion of ponicidin.Ponicidin is appointed as at peak 21 like this.
The content of phenolic acid and diterpene in embodiment 6 Rabdosia rubescens stem water extracts
The 6 kind phenolic acid having confirmed structure corresponding according to the ion flow of Rabdosia rubescens stem water extract under HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS detection and 4 kinds of diterpene are (corresponding to peak 1,10,11,14,15,16,17,19,20 and 21) peak area accounts for 72.81% of 22 peaks.
Embodiment 7 Rabdosia rubescens stem water extracts are removed the activity of DPPH free radical
DPPH is a kind of stable free radical, can be removed fast by the protic free radical scavenger.Free radical scavenger in food and biosystem can be measured by the spectrogram on EPR spectrometer by DPPH.The free radical scavenging activity of the antioxidant of natural origin also can be measured by the spectrogram on EPR spectrometer by DPPH.According to the 3rd peak in collection of illustrative plates, the present invention finds that the activity of Rabdosia rubescens stem water extract removing DPPH free radical depends on concentration.0.13,0.25,0.35,0.55,0.70 and 1.00mg/mL concentration under Rabdosia rubescens stem water extract remove respectively 13%, 15%, 26%, 40%, 63%and78%DPPH free radical (Fig. 2 a, b).Rabdosia rubescens stem water extract is removed the concentration (IC of 50%DPPH free radical
50) be 0.55mg/mL.Fig. 2 a, b show that Rabdosia rubescens stem water extract has the effect of obvious DPPH free radical scavenging, are outstanding antioxidants.
Embodiment 8 Rabdosia rubescens stem water extracts are removed the activity of hydroxy radical
Fe
2+/ H
2O
2The hydroxy radical that system generates can be caught and form by DMPO the DMPO-OH adduct and measure (Fig. 2 b) on EPR spectrometer.Remove the activity of hydroxy radical according to the high computational Rabdosia rubescens stem water extract at the 3rd peak in collection of illustrative plates.This activity represents with the relative quantity of DMPO-OH adduct.The present invention finds, after adding Rabdosia rubescens stem water extract, the intensity at paramagnetic resonance peak adds the concentration of Rabdosia rubescens stem water extract increase and reduce.The concentration of the Rabdosia rubescens stem water extract that adds is 10.00,15.00,20.00,30.00 during with 40.00mg/mL, the clearance rate of hydroxy radical is respectively 43%, 70%, 77%, 89% and 97% (Fig. 3 a, b). Rabdosia rubescens stem water extract is removed the concentration (IC of 50% hydroxy radical
50) be 11.43mg/mL.Fig. 3 a, b show that Rabdosia rubescens stem water extract has obvious Hydroxyl Radical Scavenging, are outstanding antioxidants.
Claims (9)
1. the preparation technology of Rabdosia rubescens stem water extract, this technique comprises cleans chopping afterwards with dried Rabdosia rubescens stem with tap water, use the hot water diafiltration of 70-90 ℃ in the ratio of 1: 40 (g/mL), the speed that percolate flows out is 10-30mL/ minute, effluent obtains Rabdosia rubescens stem water extract dry powder in 40-60 ℃ of concentrating under reduced pressure.
2. method according to claim 1, wherein dried Rabdosia rubescens stem is 1: 30 (g/mL) with the ratio of the hot water that is used for diafiltration.
3. method according to claim 1, the temperature that wherein is used for the hot water of diafiltration is 80 ℃.
4. method according to claim 1, wherein the speed that flows out of percolate is 20mL/ minute.
5. method according to claim 1, wherein the temperature of effluent concentrating under reduced pressure is 50 ℃.
6. the Rabdosia rubescens stem water extract for preparing of the either method of claim 1-6, is characterized in that the dry powder that this Rabdosia rubescens stem water extract concentrating under reduced pressure obtains is faint yellow solid.
7. HPLC-PAD/ (-) the ESI-MS-MS finger printing of Rabdosia rubescens stem water extract.
8. HPLC-PAD/ (+) the ESI-MS-MS finger printing of Rabdosia rubescens stem water extract.
9. Rabdosia rubescens stem extract is as the application of free radical scavenger.
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| CN103142690A (en) * | 2011-12-07 | 2013-06-12 | 彭莉 | Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as antithrombotic agent |
| CN103142688A (en) * | 2011-12-07 | 2013-06-12 | 彭莉 | Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as anti-inflammatory agent |
| CN112083091A (en) * | 2020-08-27 | 2020-12-15 | 四川新绿色药业科技发展有限公司 | UPLC characteristic spectrum of rabdosia rubescens formula granules and construction method and application thereof |
| CN112083091B (en) * | 2020-08-27 | 2022-07-22 | 四川新绿色药业科技发展有限公司 | UPLC characteristic spectrum of rabdosia rubescens formula granules and construction method and application thereof |
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