CN101696202A - Phenylpropanoid compound contained in rhodiola, preparation method thereof and application thereof - Google Patents
Phenylpropanoid compound contained in rhodiola, preparation method thereof and application thereof Download PDFInfo
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- CN101696202A CN101696202A CN200910095109A CN200910095109A CN101696202A CN 101696202 A CN101696202 A CN 101696202A CN 200910095109 A CN200910095109 A CN 200910095109A CN 200910095109 A CN200910095109 A CN 200910095109A CN 101696202 A CN101696202 A CN 101696202A
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Abstract
The invention discloses a new phenylpropanoid compound contained in rhodiola, a preparation method thereof and application thereof. The compound has a novel structure of general formula (I). The preparation method comprises the following steps: airing and crushing the whole strain of rhodiola, ultrasonically extracting the rhodiola by using 70 percent acetone gradually after crushing, combining and filtering the extracting solutions, concentrating the extracting solution to form an extract, then primarily separating the extract by using silica gel column chromatography, and further separating the extract by adopting efficient liquid semi-preparation chromatograph to obtain the required compound. By performing HIV-1 resistant activity screening on the compound, the experimental result shows good HIV-1 resistant and anti-oxidation activities, the treatment index of the HIV-1 is 55.2, and the anti-oxidation median clearance concentration IC50 is 9.68 mug/L.
Description
Technical field
The present invention relates to a kind of natural compounds, more particularly, the present invention relates to a kind of phenylpropyl alcohol chlorins compound of the novelty that extraction separation obtains from Root of Kirilow Rhodiola.Simultaneously, the invention still further relates to the preparation method of described compound and the application in pharmacy thereof.
Background technology
Root of Kirilow Rhodiola (Rhodiola rosea L.) is a perennial herb, high 10-20 centimetre, belong to Rosaceae Rhodida plant, and mainly be distributed in provinces such as northeast, Gansu, Xinjiang, Sichuan, Tibet and Yunnan-Guizhou.Root and rhizome can be used as medicine, and has strengthening by means of tonics, is holding up that this is solid just, antifatigue, the anti-ageing effect of waiting for a long time.Rhodida plant contains volatile oil, pectin, Sitosterol, tannin, benzenetriol, Phloroglucinol, anthraquinone, oxalic acid, quinhydrones, Resorcinol, forulic acid, catechin, catechuic acid, tonka bean camphor, flavonoid and glycoside compound.Rhodioloside (salidroside) is the maximum effective constituent of research.
The plain class of phenylpropyl alcohol (phenylpropanoids) is meant that basic parent nucleus has one or several C
6-C
3Unitary natural organic-compound monoid extensively is present in the natural phant.Known phenylpropyl alcohol chlorins compound has effects such as antisepsis and anti-inflammation, antitumor, antiviral, anti-oxidant, liver protecting and base reparation, for diabetes and relative disease, and to the sexual dysfunction due to physical and psychological pressure, study, the low inferior all tools of memory capability improve significantly.The present invention separates from Root of Kirilow Rhodiola and obtains a kind of new phenylpropyl alcohol chlorins compound, and this compound has tangible anti-HIV-1 and anti-oxidant activity.
Summary of the invention
The present invention is based on a kind of like this discovery and finishes, and promptly furthers investigate by the chemical ingredients to Root of Kirilow Rhodiola, obtains a kind of compound of novel structure, and has carried out the active and anti-oxidant activity screening of anti-HIV-1, has disclosed its good pharmaceutical use.
The object of the present invention is to provide a kind of new benzo compounds with pharmaceutical use.
Another object of the present invention provides a kind of preparation method of described new compound.
Further aim of the present invention provides the purposes of described new compound aspect preparation AIDS resisting (HIV) and oxidation resistant medicine.
Purpose of the present invention is achieved by following technical proposals.
* except as otherwise noted, the percentage ratio that is adopted among the present invention is mass percent.
A. the present invention has isolated a kind of new compound from Root of Kirilow Rhodiola, and this compound is represented with following structural formula:
This compound is named as: 2-hydroxyl-1-(3,4-methylene-dioxy, 5-p-methoxy-phenyl)-1-acetone;
English name: 2-hydroxyl-1-(3,4-methylenedioxyl-5-methoxyphenyl)-1-propanone.
B. the invention provides the preparation method of described phenylpropyl alcohol element, this method adopts following step:
(1) is raw material with the Root of Kirilow Rhodiola, its complete stool is dried, be crushed to 20～40 orders;
(2) be solvent supersound extraction 3～5 times with 70% acetone, each 30～60 minutes, extracting solution merged, filters, and the concentrating under reduced pressure extracting solution obtains medicinal extract;
(3) medicinal extract carries out the silica gel column chromatography rough segmentation with 80～200 purpose silica gel dry column-packings, and with chloroform: acetone carries out gradient elution by 20: 1～7: 3 proportioning, collects the various piece elutriant and concentrates; 3: 2 parts of elutriant are further used the high performance liquid chromatography separation and purification, and flow velocity is 2.5～3.5mL/min, are moving phase with the methanol, progressively adjust the two ratio and segment step by step, promptly obtain required phenylpropyl alcohol chlorins compound.
C. this compound has been carried out the anti-HIV-1 screening active ingredients, compound exhibits goes out good anti-HIV-1 activity, and its therapeutic index is 86.5.
D. this compound has been carried out the anti-oxidant activity screening, compound exhibits goes out good antioxidant activity.It is 10.6 μ g/L that its half is removed concentration IC50 measurement result.
Compared with prior art, the present invention has following outstanding advantage:
1. Root of Kirilow Rhodiola is widely distributed in China, abundant raw material, low price; And the phenylpropyl alcohol element of The compounds of this invention content in Root of Kirilow Rhodiola is higher relatively, obtains easily;
2. adopted conventional column chromatography and high performance liquid chromatography bonded preparation method, the compound operating process is simple, the The compounds of this invention purity height that is obtained, and follow-up suitability for industrialized production realizes easily;
3. The compounds of this invention shows good anti-AIDS and anti-oxidant activity, can be new compound or lead compound that medicine industry provides pharmaceutical use.
Description of drawings
Fig. 1 be The compounds of this invention proton nmr spectra (
1H NMR);
Fig. 2 be The compounds of this invention nucleus magnetic resonance charcoal spectrum (
13C NMR).
Fig. 3 is that the main HMBC of The compounds of this invention is relevant.
Embodiment
In order to make purpose of the present invention, technical scheme and advantage clearer,, the present invention is described in further detail below in conjunction with drawings and Examples.Should be appreciated that specific embodiment described herein only in order to explanation the present invention, and be not used in qualification the present invention.
Root of Kirilow Rhodiola with state, Dali, Yunnan Province is a raw material.Its complete stool (comprising root, stem, leaf) is dried, be crushed to 40 orders, the sample after the pulverizing was with 70% acetone supersound extraction 4 times (weight ratio of plant material and acetone is 1: 5), each 20 minutes; Extracting solution merges, filters, the concentrating under reduced pressure extracting solution gets medicinal extract, and medicinal extract is mixed sample with thick silica gel (80 order), carries out the silica gel column chromatography rough segmentation with 100 purpose silica gel dry column-packings, use chloroform: acetone (20: 1 → 7: 3) carries out gradient elution, and the elutriant of collecting various piece also concentrates.Chloroform: the part that acetone washes at 3: 2 high performance liquid chromatography separation and purification, flow velocity is 3mL/min, is moving phase with the methanol, progressively adjusts the two ratio and segments step by step, promptly obtains the plain compound of required phenylpropyl alcohol.
Repeat the process of embodiment 1, but following difference arranged: with raw material pulverizing to 30 orders; Sample after the pulverizing is with 70% acetone supersound extraction 3 times (weight ratio of plant material and acetone is 1: 6), each 30min; Carry out the silica gel column chromatography rough segmentation with 150 purpose silica gel dry column-packings, use chloroform: acetone (20: 1 → 7: 3) carries out gradient elution, and the elutriant of collecting various piece also concentrates.Chloroform: the part that acetone washes at 3: 2 high performance liquid chromatography separation and purification, flow velocity is 2.5mL/min, is moving phase with the methanol, progressively adjusts the two ratio and segments step by step, promptly obtains the plain compound of required phenylpropyl alcohol.
Repeat the process of embodiment 1, but following difference arranged: with raw material pulverizing to 25 orders; Sample after the pulverizing is with 70% acetone supersound extraction 5 times (weight ratio of plant material and acetone is 1: 3), each 50min; Extracting solution merges, filters, and the concentrating under reduced pressure extracting solution gets medicinal extract, carries out the silica gel column chromatography rough segmentation with 200 purpose silica gel dry column-packings, uses chloroform: acetone (20: 1 → 7: 3) carries out gradient elution, collects various piece elutriant and concentrated.Chloroform: the part that acetone washes at 3: 2 high performance liquid chromatography separation and purification, flow velocity is 3.5mL/min, is moving phase with the methanol, progressively adjusts the two ratio and segments step by step, promptly obtains the plain compound of required phenylpropyl alcohol.
--to the evaluation of The compounds of this invention structure
This compound is a white solid; UV spectrum (solvent is a methyl alcohol), λ
Max(log ε) 272 (2.96), 210 (5.62) nm; Infrared spectra (pressing potassium bromide troche) ν
Max2926,2858,1635,1584,1528,1468,1416,1138,868cm
-1HRESIMS shows its quasi-molecular ion peak m/z 233.0429[M+Na]
+(calcd 233.0426) determine that in conjunction with the NMR spectrum its molecular formula is C
10H
10O
5, degree of unsaturation is 5.
1H and
13C NMR spectrum (see accompanying drawing-1 and accompanying drawing-2, attribution data sees Table-1) shows in the molecule has 1 phenyl ring (1 methoxyl group, 1 methylene-dioxy, 2 methyne double key carbons are arranged on the phenyl ring), 1 carbonyl, the methyne of 1 oxidation, 1 methyl.The structure of this compound of the relevant spectrum of HMBC (accompanying drawing-3) susceptible of proof confirms that by SCIFINDER inquiry and literature search this compound is a new compound.
Table-1 compound
1H and
13C NMR data (CDCl
3)
--the HIV (human immunodeficiency virus)-resistant activity to The compounds of this invention detects
1.HIV-1 infectious titration
Press Johnson ﹠amp; The described method improvement of Byington carries out titration; Press Reed ﹠amp; The Muench method is calculated the TCID of virus
50(50%Tissue Culture Infection Dose).
2. sample detects the cytotoxicity of C8166 host cell
4 * 10
5/ ml C8166 cell suspension 100ul mixes with testing compound solution, establishes three repeating holes.The control wells that does not contain compound, 37 ℃ of temperature, 5%CO are set simultaneously
2Cultivated three days, and adopted the MTT colorimetry to detect cytotoxicity.ELx800 ELISA instrument is measured the OD value, and the mensuration wavelength is 595nm, and reference wavelength is 630nm.Calculate CC
50Value (50%Cytotoxic Concentration), the compound concentration during promptly to 50% normal T lymphocyte series C8166 toxigenicity.
3. sample is to HIV-1
IIIBInduce the inhibition test of C8166 cytopathy (CPE)
With 8 * 10
5/ mL C8166 cell 50 μ L/ holes are inoculated on the 96 porocyte culture plates that contain 100 μ L/ hole doubling dilution compounds, add the HIV-1 of 50 μ L then
IIIBDilution supernatant (M.O.I.0.0016).If three repeating holes.The normal cell control wells that does not contain compound is set simultaneously.37 ℃, 5%CO
2Cultivated three days, (100 *) count plasmodial formation under the inverted microscope.EC
50(50%EffectiveConcentration) form 50% o'clock compound concentration for suppressing synplasm.
4. sample is to the provide protection test of HIV cells infected
With 8 * 10
5/ ml MT
4Cell 50ul/ hole is inoculated on the 96 porocyte culture plates that contain 100 μ l/ hole doubling dilution compounds, and half hole of culture plate adds the HIV-1 of 50 μ l
IIIBDilution (M.O.I.0.006), second half hole adds 50 μ l substratum.2 repeating holes of each concentration gradient are provided with control wells and the blank hole that does not contain compound, 37 ℃, 5%CO simultaneously
2Cultivate, 100 μ l fresh cultures were added in every hole in the 3rd day, adopted the MTT colorimetry to detect cell survival rate in the 5th day or the 6th day.The ELx800ELISA instrument is measured the OD value, and the mensuration wavelength is 595nm, and reference wavelength is 630nm.Calculate compound to Normocellular toxicity with to HIV-1 with formula
IIIBThe provide protection of cells infected.
5. calculation formula
Draw dose response curve according to experimental result, press Reed﹠amp; The Muench method calculates the 50% effective concentration (EC that compound suppresses virus
50), 50% cell growth inhibiting concentration (CC
50) and the active therapeutic index TI value of anti-HIV-1 (Therapeutic index) be: TI=CC
50/ EC
50
Cell growth survival rate (%)=experimental port OD value/control wells OD value * 100
Inhibitory rate of cell growth (%)=(1-experimental port OD value/control wells OD value) * 100
The cytopathogenic inhibiting rate of HIV-1 (%)=(1-experimental port synplasm number/control wells synplasm number) * 100
The protection ratio of cells infected (%)=
(experimental port OD value-positive control hole OD value)/(negative control hole OD value-positive control hole OD value) * 100
6. experimental result
Experimental result clearly illustrates that this compound exhibits goes out certain anti-HIV-1 activity, and its therapeutic index is 55.2, has disclosed compound of the present invention and has had a good application prospect in the medicine of preparation AIDS resisting.
Embodiment 6
--compound with oxidation resistance is active to be detected
Anti-oxidant activity is represented with the size of removing DPPH free radical ability; With 50 μ g/mL is primary dcreening operation concentration, measures the activity that it removes fat free love base DPPH.Get costar 96 orifice plates, add freshly prepared DPPH ethanolic soln (6.5 * 105mol/L) 190 μ L/ holes, add testing sample 10 μ L/ holes, blank well adds 10 μ L physiological saline, abundant mixing, left standstill 30 minutes with lucifuge under the room temperature behind the shrouding film shrouding, measure each hole absorbance on determinator on the UV2401 spectrophotometer, the mensuration wavelength is 517nm; Sample is calculated as follows fat free love base DPPH clearance rate:
DPPH clearance rate (%)=(A blank-A sample)/A blank * 100%
A blank: blank group absorbance; A sample: add the sample sets absorbance.
Sample detects for parallel 5 times, calculates half and removes concentration IC50, and the IC50 measurement result is 9.68 μ g/L, shows that compound has good antioxidant activity.
The above only is preferred embodiment of the present invention, not in order to restriction the present invention, all any modifications of being done within the spirit and principles in the present invention, is equal to and replaces and improvement etc., all should be included within protection scope of the present invention.
Claims (4)
1. phenylpropyl alcohol chlorins compound with following structural formula:
2. the preparation method of the described compound of claim 1 is characterized in that, this method adopts following steps:
(1) is raw material with the Root of Kirilow Rhodiola, its complete stool is dried, be crushed to 20～40 orders;
(2) be extraction agent supersound extraction 3～5 times with 70% acetone, each 30～60 minutes; Extracting solution merges, filters, and the concentrating under reduced pressure extracting solution gets medicinal extract;
(3) medicinal extract carries out the silica gel column chromatography rough segmentation with 200～300 purpose silica gel dry column-packings then with 80～100 purpose silica gel mixed samples, and with chloroform: acetone carries out gradient elution by 20: 1～7: 3 proportioning, collects the various piece elutriant; 3: 2 parts high performance liquid chromatography separation and purification of elutriant, flow velocity is 2.5～3.5mL/min, is moving phase with the methanol, progressively adjusts the two ratio and segments step by step, promptly obtains required phenylpropyl alcohol element.
3. the application of the described phenylpropyl alcohol chlorins compound of claim 1 in the medicine of preparation treatment or prevention AIDS.
4. the application of the described phenylpropyl alcohol chlorins compound of claim 1 in the oxidation resistant medicine of preparation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910095109 CN101696202B (en) | 2009-10-28 | 2009-10-28 | Phenylpropanoid compound contained in rhodiola, preparation method thereof and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910095109 CN101696202B (en) | 2009-10-28 | 2009-10-28 | Phenylpropanoid compound contained in rhodiola, preparation method thereof and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101696202A true CN101696202A (en) | 2010-04-21 |
| CN101696202B CN101696202B (en) | 2012-05-02 |
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ID=42141342
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200910095109 Expired - Fee Related CN101696202B (en) | 2009-10-28 | 2009-10-28 | Phenylpropanoid compound contained in rhodiola, preparation method thereof and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102267895A (en) * | 2011-08-04 | 2011-12-07 | 云南烟草科学研究院 | Phenylpropanoid compound as well as preparation method and application thereof |
| CN102388999A (en) * | 2011-11-11 | 2012-03-28 | 中国科学院西北高原生物研究所 | Preparation method of rhodiola root tea bag |
| CN107513019A (en) * | 2016-06-16 | 2017-12-26 | 江苏康缘药业股份有限公司 | Compound, its preparation method and the application extracted from Rhodiola |
| CN117529487A (en) * | 2021-06-03 | 2024-02-06 | 拿波佳尔股份有限公司 | Novel phenylpropanoid compounds |
-
2009
- 2009-10-28 CN CN 200910095109 patent/CN101696202B/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102267895A (en) * | 2011-08-04 | 2011-12-07 | 云南烟草科学研究院 | Phenylpropanoid compound as well as preparation method and application thereof |
| CN102267895B (en) * | 2011-08-04 | 2014-08-06 | 云南烟草科学研究院 | Phenylpropanoid compound as well as preparation method and application thereof |
| CN102388999A (en) * | 2011-11-11 | 2012-03-28 | 中国科学院西北高原生物研究所 | Preparation method of rhodiola root tea bag |
| CN107513019A (en) * | 2016-06-16 | 2017-12-26 | 江苏康缘药业股份有限公司 | Compound, its preparation method and the application extracted from Rhodiola |
| CN107513019B (en) * | 2016-06-16 | 2020-06-26 | 江苏康缘药业股份有限公司 | Compound extracted from rhodiola rosea, preparation method and application thereof |
| CN117529487A (en) * | 2021-06-03 | 2024-02-06 | 拿波佳尔股份有限公司 | Novel phenylpropanoid compounds |
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| Publication number | Publication date |
|---|---|
| CN101696202B (en) | 2012-05-02 |
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Granted publication date: 20120502 Termination date: 20121028 |