CN103142688A - Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as anti-inflammatory agent - Google Patents

Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as anti-inflammatory agent Download PDF

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CN103142688A
CN103142688A CN2011104065548A CN201110406554A CN103142688A CN 103142688 A CN103142688 A CN 103142688A CN 2011104065548 A CN2011104065548 A CN 2011104065548A CN 201110406554 A CN201110406554 A CN 201110406554A CN 103142688 A CN103142688 A CN 103142688A
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rabdosia rubescens
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彭师奇
赵明
姚兴河
彭莉
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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 the anti-inflammatory activity of the rabdosia rubescens stem aqueous extract in a mice ear-swelling model and a use of the rabdosia rubescens stem aqueous extract as an anti-inflammatory agent.

Description

Rabdosia rubescens stem water extract, its preparation method, finger printing and as the application of antiinflammatory
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 the anti-inflammatory activity on the mice ear model of this water extract and as the application of antiinflammatory.The invention belongs to biomedicine field.
Background technology
Inflammation is a kind of common disease symptoms, and is closely related with infection.Although acute inflammation is the protective response that body infects antibacterial, chronic inflammatory disease is the cercinoma prophase pathologic change of some major disease.For example chronic inflammatory disease is the precancerous lesion of generally acknowledging.Research and develop anti-inflammatory drug safely and effectively, have clear and definite using value.
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.Obviously, the water extract of LINGCAO leaf has antiinflammatory action.
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 the water extract of Rabdosia rubescens leaf for heat-clearing and toxic substances removing, pharynx-clearing throat-benefiting and reducing swelling and alleviating pain, is seen in document without any the research that is used for antiinflammatory with the water extract of Rabdosia rubescens stem among the people so far.Compare with leaf, Rabdosia rubescens stem shared ratio in herb is high a lot, and the application of exploitation Rabdosia rubescens stem in medicine has many-sided meaning.
By long-term anti-inflammatory drug research accumulation, the inventor locks phenolic acid and diterpene is the structure type with anti-inflammatory 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, and use HPLC-(-) ESI-Q-TOF-MS/MS finger printing and HPLC-(+) ESI-Q-TOF-MS/MS finger printing disclose the chemical composition of Rabdosia rubescens stem water extract, the antiinflammatory action that use mice ear model discloses Rabdosia rubescens stem water extract.
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 is to disclose the antiinflammatory action of Rabdosia rubescens stem water extract with the mice ear model, for the prevention precancerous lesion provides Rabdosia rubescens stem water extract as the high healthy material that has no side effect of anti-inflammatory 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 is concentrated into dried, the dry powder that obtains and analyzes to get finger printing, the dry powder use mice ear model evaluation antiinflammatory action that obtains with HPLC-(-) ESI-Q-TOF-MS/MS and HPLC-(+) ESI-Q-TOF-MS/MS.
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
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-(-) ESI-Q-TOF-MS/MS of embodiment 2 Rabdosia rubescens stem water extracts and HPLC-(+) ESI-Q-TOF-MS/MS finger printing
HPLC：Waters?2795?Separations?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
Figure BSA00000632489500031
Figure BSA00000632489500041
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.
Figure BSA00000632489500051
(-) 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.
Figure BSA00000632489500062
(-) 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.
Figure BSA00000632489500071
(-) 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.
Figure BSA00000632489500072
(-) 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.
Figure BSA00000632489500073
(-) 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.
Figure BSA00000632489500081
(-) 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.
Figure BSA00000632489500082
(-) 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.Rabdoternin D is appointed as at peak 16 like this.
Figure BSA00000632489500091
(-) 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.
Figure BSA00000632489500092
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.
The oral anti-inflammatory activity evaluation of embodiment 7 Rabdosia rubescens stem water extracts
Male ICR mouse (20 ± 2g), raised one day under experimental temperature before experiment.In aqueous solution, each experiment is established the normal saline group and is made parallel control with compound dissolution of the present invention.Gastric infusion, dosage are only (blank), aspirin 35mg/kg (positive control), Rabdosia rubescens leaf water extract 35mg/kg (position contrast) and Rabdosia rubescens stem water extract 35mg/kg of normal saline 0.2ml/.After administration, evenly spread upon 30 μ L dimethylbenzene on mouse right ear half an hour, smears after complete 2 hours and put to death mice, weighs to the poor of two ears.The result that obtains is listed table 2 in.Result shows that compound of the present invention has clear and definite antiinflammatory action.Result shows under 35mg/kg dosage, and Rabdosia rubescens leaf water extract has antiinflammatory action.In aspirin, Rabdosia rubescens leaf water extract (position contrast) and Rabdosia rubescens stem water extract, the anti-inflammatory activity of Rabdosia rubescens stem water extract is the strongest.Rabdosia rubescens stem water extract is outstanding antiinflammatory.
The oral anti-inflammatory activity (n=12) of table 2 Rabdosia rubescens stem water extract
Figure BSA00000632489500101
N=12, two ear weight differences represent with mean value ± SD; A) with normal saline and Rabdosia rubescens leaf group than p＜0.01, with the aspirin group than p＜0.05; B) with physiology salt group than p＜0.05.

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 antiinflammatory.
CN2011104065548A 2011-12-07 2011-12-07 Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as anti-inflammatory agent Pending CN103142688A (en)

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CN103142689A (en) * 2011-12-07 2013-06-12 彭莉 Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as free-radical scavenger
CN112353843A (en) * 2020-11-06 2021-02-12 北京恒润泰生医药科技有限公司 Rabdosia rubescens stem aqueous extract powder, preparation, anti-tumor effect and application thereof

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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
CN103142689A (en) * 2011-12-07 2013-06-12 彭莉 Rabdosia rubescens stem aqueous extract and its preparation method, finger-prints and use as free-radical scavenger
CN112353843A (en) * 2020-11-06 2021-02-12 北京恒润泰生医药科技有限公司 Rabdosia rubescens stem aqueous extract powder, preparation, anti-tumor effect and application thereof

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