CN103191041A - Chinese yew branch and leaf extractive with anti-oxidative effect as well as extraction method and application of yew branch and leaf extractive - Google Patents
Chinese yew branch and leaf extractive with anti-oxidative effect as well as extraction method and application of yew branch and leaf extractive Download PDFInfo
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Abstract
The invention relates to a Chinese yew branch and leaf extractive which is prepared from branches and/or leaves of Chinese yew serving as raw materials. The Chinese yew branch and leaf extractive comprises 12-58% of flavone, 9-47% of phenol lignan and the balance of tannin. The antioxidant ingredient of Chinese yew is applied to preparation of antioxidants or is added into antioxidant beauty cosmetics, wherein polyphenols in Chinese yew is used as an additive to be added into skin care products, can clean away radicals, has anti-aging, skin whitening, activating and moisturizing functions and can also resist ultraviolet radiation b (UVB) and ultraviolet radiation a (UVA).
Description
Technical field
The present invention relates to the extraction of a kind of Ramulus et folium taxi cuspidatae, more specifically relate to a kind of Ramulus et folium taxi cuspidatae extract, its extracting method and application with antioxidation.
Background technology
Ramulus et folium taxi cuspidatae is that collection is viewed and admired, material with, medicinally be the high seeds of economic worth of one.Up to the present, chemists have extracted from this platymiscium and have obtained more than 300 taxane diterpene-kind compound and many alkaloid compounds, wherein some composition such as Ramulus et folium taxi cuspidatae time alkali also has the active anticancer of similar paclitaxel, and other compositions such as 1-hydroxyl bar card booth I can come taxol biosynthesis by chemical modification.In addition, some scholars also separate from this platymiscium and obtain 14 kinds in a kind of ecdysterone, 5 kinds of triterpenes, 7 kinds of lignanoids, 3 kinds of glycosides, 8 kinds of bisflavones, flavone compound kaempferol-4-methyl ether, other organic acid and aldehyde etc., glucosides class and polysaccharide compound etc.Scientist finds that Ramulus et folium taxi cuspidatae can also improve body immunity, and the natural functions of human body is recovered.It not only has remarkable result to hypertension, hyperglycemia, hyperlipidemia, nephropathy and dysmenorrhoea etc., can also reduce urine protein and run off.Simultaneously, contain a large amount of tannins in the Ramulus et folium taxi cuspidatae, these materials have antibacterial, antiinflammation, not only upper respiratory tract infection are had therapeutical effect, also nephritis, gastritis, enteritis, rheumatoid etc. are had significant curative effect.Because therefore the Chinese yew genus plants scarcity of resources extracts Ramulus et folium taxi cuspidatae, be applied to the research focus that anti-cancer and cancer-preventing is relevant research staff always by selecting scientific and reasonable extracting method to screen specific effective ingredient, as:
Chinese patent ZL200410043649.8 discloses extracting method and the application thereof of a kind of Chinese yew genus plants extract and this extract.Described extract is that the branch and leaf with Ramulus et folium taxi cuspidatae are that raw material extracts and forms, it comprises following compositions: taxane diterpene compound, total lignans, total flavones, described taxane diterpene compound account for three kinds of composition cumulative volumes 18～68%, total lignans account for three kinds of composition cumulative volumes 14～61%, total flavones accounts for 10～50% of three kinds of composition cumulative volumes.Its extracting method is prepared according to following step: a, be that 40～95% alcohol solvent returns and carries 1～3 hour with the branch and leaf volumetric concentration of Chinese yew genus plants medical material, be condensed into former extractum; B, add the distilled water of 30～80 times of former extractum weight then, the former extractum of dissolving under 60～80 ℃ or ultrasonic condition leaves standstill the back and filters centrifugal, precipitation; C, to be 50～90% ethanol with volumetric concentration extract above-mentioned precipitate under 60～80 ℃ or ultrasonic condition, extracts three times, and the each addition of ethanol is 5～15 times of weight of precipitate, leaves standstill back filtration, centrifugal; D, merge ethanol extract, in extracting solution, add ethanol, be mixed with and contain that the alcohol amount is 20～40%, volume is the solution of 30～70 times of above-mentioned former extractum; E, with above-mentioned solution by the macroporous adsorption resin chromatography post, the consumption of macroporous adsorbent resin is 10～20 times of former extractum weight; F, be 20～40% alcoholic solution upper prop with volumetric concentration, wash to color lightly that the ethanol consumption is 8～12 times of column volume, flow velocity 0.5～1.5 column volume/hour; G, be 40～60% alcoholic solution upper prop with volumetric concentration then, wash to color lightly that the ethanol consumption is 8～15 times of column volume, flow velocity 0.5～1.5 column volume/hour; H, be 65～80% alcoholic solution upper prop with volumetric concentration again, wash to color lightly that the ethanol consumption is 10～15 times of column volume, flow velocity 0.5～1.5 column volume/hour; I, collect eluent respectively, be evaporated to driedly, obtain the extract of Chinese yew genus plants.This extract can be used as the effective ingredient of cancer therapy drug.Its anticancer effect is not less than paclitaxel, realized the continuous utilization of Chinese yew genus plants simultaneously again, and side effect is extremely low.Under the prerequisite that guarantees curative effect, improved the utilization rate of Chinese yew genus plants, to bring up to more than 5/1000ths from single extraction paclitaxel utilization rate less than 2/10000ths, utilization rate improves more than 25 times.
Chinese patent ZL200910157034.0 discloses a kind of extract and preparation method of Taxus mairei blade, this extract is pale yellow powder, contain weight content in this powder and be 65～70% Ramulus et folium taxi cuspidatae flavone, the Ramulus et folium taxi cuspidatae flavone comprises following 5 kinds of compositions: 3-O-rutin-Quercetin, 3-O-rutin-kaempferol, 3-O-rutin-myricetin, 7-O-glucose-kaempferol and 7-O-glucose-Quercetin, the gross weight content of above-mentioned 5 kinds of compositions is 40～60% in the Ramulus et folium taxi cuspidatae flavone, this extract is raw material with fresh southern Semen Phaseoli blade, through oven dry, crushing screening, immerse alcohol solvent, stir supersound extraction down, the extracting solution concentrating under reduced pressure removes alcohol, the chloroform extraction defat, the preparation method of water concentrate drying makes; The present invention is a kind of heart of improvement microcirculation that has, and arrhythmia reduces myocardium keto consumption etc., extract and energy consumption to the Taxus mairei blade of the treatment of cardiovascular system diseases and health-care effect are low, extraction time is short, and impurity is few, the preparation method that extraction ratio is higher.
Chinese patent ZL03129421.9 discloses extract and the extracting method in a kind of Ramulus et folium taxi cuspidatae.This extract is polysaccharide component, is mainly the heteropolysaccharide of being made up of with β-1,3 glycosidic bond D-glucose and a spot of D-xylose, arabinose, galactose and glucuronic acid, at its β-1, on the 3 glucosan main chains, there is a small amount of β-1,6 glycosidic bond branch; It has antitumaous effects such as immunomodulating and direct inhibition tumor cell, and the toxic and side effects of itself is very little, by studying its antitumous effect with experiment in vitro in the body, it has the good restraining effect to Kunming mouse S180 ehrlich ascites carcinoma, is used for development cancer therapy drug aspect and has a good application prospect.
Technique scheme all is based on Ramulus et folium taxi cuspidatae extract at the pharmacologically active of aspects such as anti-cancer and cancer-preventing and use proposes, in the prior art, to the Ramulus et folium taxi cuspidatae extract The Chemical Constituents object also researchs that are limited to bearing taxanes more, and Ramulus et folium taxi cuspidatae is except containing bearing taxanes, also has other non-bearing taxanes such as flavonoid, polysaccharide, other organic acid and aldehyde and a large amount of tannin etc.The further above-mentioned active component of research, explore it in other respects as the pharmacologically active of antioxidation etc. significant, in view of this, special proposition the present invention.
Summary of the invention
First purpose of the present invention is to provide a kind of Ramulus et folium taxi cuspidatae extract, by Ramulus et folium taxi cuspidatae is extracted, the active component that screening wherein has antioxidation, obtain a kind of Ramulus et folium taxi cuspidatae extract with remarkable antioxidation, make Ramulus et folium taxi cuspidatae class medical material can give full play to its potential advantages and resources advantage.
For realizing first purpose, adopt following technical scheme:
A kind of Ramulus et folium taxi cuspidatae extract, with Taxus mairei the branch and/or leaf be that feedstock production forms, comprise 12%～58% flavone in the described Ramulus et folium taxi cuspidatae extract, 9%～47% phenols lignanoid, all the other are tannin.
Wherein, described flavone comprises kaempferol, and described phenols lignanoid comprises (-)-alpha-Conidendrin.
The extracting method of above-mentioned Ramulus et folium taxi cuspidatae extract comprises the steps:
(1) preparation extractum: get branch of Ramulus et folium taxi cuspidatae and/or leaf, impregnated in the alcoholic solution that mass concentration is 70%-75%, extract with alcoholic solution, the residue medicinal residues continue to use water extraction, merge water and alcoholic solution, reflux with petroleum ether, and Soxhlet is extracted and reclaimed solvent, obtains extractum;
(2) gradient elution: with the extractum water dissolution, last HP20 macroporous resin, the pure liquid of the pure liquid of the pure liquid of water, 15-25%, 35-45%, 55-65% in order, the pure liquid gradient elution of 75-85%, collection also merges each eluent, namely gets Ramulus et folium taxi cuspidatae extract.
Wherein, each eluent preferably is respectively water liquid, 20% pure liquid, 40% pure liquid, 60% pure liquid, 80% pure liquid in the step 2.Collect each section eluent this moment, namely gets the optimal Ramulus et folium taxi cuspidatae extract of purity and productive rate.
Wherein, the consumption of each eluent is 8-10 times of column volume in the step 2, and flow velocity is 1-1.5mL/min.The consumption of preferred each eluent is 9 times of column volumes, and flow velocity is 1.2mL/min.
Wherein, the alcohol in described step 1 and the step 2 is preferably ethanol.
Wherein, described extracting method also comprises Ramulus et folium taxi cuspidatae extract concentrated and desolventizes the step that obtains extract extractum.Described concentrate to desolventize to those skilled in the art grasped.The present invention is not particularly limited this, and those skilled in the art can adopt disclosed any method for concentration of prior art to remove solvent in the eluent, obtain Ramulus et folium taxi cuspidatae Extract extractum or further obtain powder.
Another object of the present invention is to provide the application of Ramulus et folium taxi cuspidatae Extract as active component in the antioxidation cosmetics.
Skin is people's contact environment, accept various stimulations comprise ultraviolet radiation at first, maximum organ, so aging also obvious, the easiest generation of skin.The three approach of delay skin aging is: resist drying, uvioresistant, antioxidation.Nearly all antioxidant and facilitate the material of antioxidant in the body, the overwhelming majority is present in the natural plant.Natural plant extracts have usually multiple action, effect lasting stability, action temperature and, widely applicable, have no side effect or advantage that side effect is very little, its research and development have been become the recent tendency of complying with back to nature, science beauty treatment, science nursing idea.The present invention complies with this trend, seeks oxidation-resistant active ingredient from Ramulus et folium taxi cuspidatae, lays the foundation for further developing cosmetics.
Ramulus et folium taxi cuspidatae antioxidant content of the present invention is applied to prepare antioxidant and makes an addition in the antioxidation cosmetics, the polyphenols that wherein contains adds in the skin care item as additive, free radical there is the removing ability, the effect that has defying age, whitens, activates and preserve moisture also has the effect of anti-UVB, UVA.
Adopt technique scheme, the present invention has following advantage: Ramulus et folium taxi cuspidatae antioxidant content method for screening of the present invention is simple to operation, suitable large-scale production, collecting effect is good, the product that extracts can be used for arranging anti-acne, antibiotic, defying age, preserves moisture, sun-proof, whiten, cosmetics that speckle dispelling etc. has given efficacy, add corresponding effect type composition, make suitable dosage form, develop corresponding product.
Description of drawings
Fig. 1 is the screening of DPPH solution concentration;
Fig. 2 is the screening of DPPH solution application of sample amount;
Fig. 3 is Taxus leaf oxidation activity measurement result figure;
Fig. 4 is branch of Ramulus et folium taxi cuspidatae oxidation activity measurement result figure;
Fig. 5 is 2%Al for developer
3Cl
3The silica gel thin-layer chromatography result of alcoholic solution colour developing;
Fig. 6 is the silica gel thin-layer chromatography result of 1,2,3-indantrione monohydrate colour developing for developer;
Fig. 7 for developing solvent is: the silica gel thin-layer chromatography result of BAW (4:1:5) upper strata liquid;
Fig. 8 is methanol: the polyamide ply of paper of water (40:1) is analysed the result;
Fig. 9 for developer is: 2%Al
3Cl
3The silica gel thin-layer chromatography result;
Figure 10 is Fe for developer
3Cl
3The polyamide ply of paper of hydrochloric acid solution is analysed identification result;
Figure 11 is the assay distribution of results curve of polyphenol.
The specific embodiment
Following examples are used for explanation the present invention, but are not used for limiting the scope of the invention.
Because commercial production requires cost low, as far as possible not with an organic solvent, consider as far as possible problems such as extracting the operability that reaches industrialized producing technology fully and cost, the present invention is from choice of Solvent, the selection of chromatographic material, the selection of eluting solvent and industrial production requirement aspect are considered, adopt 75% ethanol respectively active component in branch and the leaf to be extracted, reclaim solvent and get extractum, use the HP20 macroporous resin column chromatography extract is carried out separation and purification, water successively, the pure liquid of 15-25%, the pure liquid of 35-45%, the pure liquid of 55-65%, the pure liquid gradient elution of 75-85%, preferred distilled water, 20% ethanol, 40% ethanol, 60% ethanol, the about 8-10 of 80% ethanol times column volume (generally judging according to color) gradient elution, eluent flow rate 1.5mL/min, collect the eluent of each component, eluent reclaims solvent must be for the work to be measured of examination component.
With the extracting solution of Taxus leaf called after extracting solution Y-2 ', Y-3 ', Y-4 ', Y-5 ' and Y-6 ' successively, the extracting solution of Taxus leaf successively called after Z-3 ', Z-4 ', Z-5 ', Z-6 '.
Test back result shows that oxidation-resistant active ingredient mainly concentrates on polarity than large part, and antioxidation effectively (clearance rate is more than 50%) leaf is Y-3 ', Y-4 ', and branch is Z-3 ', Z-4 ', Z-5 ', Z-6 '.
The Natural antioxidant is mainly derived from plant polyphenol, because the ortho position phenolic hydroxyl group is very easily oxidized in its phenolic hydroxyl group, and free radicals such as active oxygen is had strong capturing ability, makes plant polyphenol have very strong anti-oxidation and removes the free radical ability.The Polyphenols oxidation-resistant active ingredient of having found from a lot of plants is such as tea polyphenols, grape seed polyphenols, cacao bean polyphenol etc.Studies show that plant polyphenol content and kind are relevant with the non-oxidizability effect.
Oxidation-resistant active ingredient main in the Ramulus et folium taxi cuspidatae is mainly polyphenol compound, the present invention adopts Folin-ciocalteu reagent analytical photometry that the polyphenol content in branch of Ramulus et folium taxi cuspidatae and leaf and the antioxidant activity component is measured, measurement result shows: the content of total phenols is 3.25% in the branch, the content of total phenols is 2.35% in the leaf, polyphenol content is the highest in the antioxidant activity position of macroporous resin column chromatography technology enrichment polyphenol can reach 51.60%, and each component polyphenol content size order is: Z-3 ' (51.6%)＞Z-4 ' (48.33%)＞Z-5 ' (40.05%)＞Y-4 ' (28.72%)＞Y-3 ' (26.42%)＞Z-6 ' (25.86%)＞Y-5 ' (16.61%); And be 0.5mg/mL at each concentration of component, each component antioxidant activity (clearance rate is more than 40%) size order is: Z-4 '＞Z-3 '＞Y-4 '＞Z-6 '＞Z-5 '＞Y-3 '＞Y-5 '.The position that polyphenol content is high is described, its antioxidant activity is also stronger relatively, the size of its antioxidant activity of plant polyphenol is not only relevant with the content of polyphenol, also relevant with its kind, its antioxidant activity of different phenolic compounds varies in size, and the antioxidant activity of general phenolic compound increases along with the increase of ortho position dihydroxy group.
Commercial production is used macroporous resin always, and macroporous resin is a kind of organic high poly-adsorbent, and Chinese herbal medicine effective ingredients is the result of active force between macroporous resin and effective ingredient form based on a part of Van der Waals force and hydrogen bond in the absorption on the macroporous resin.Macroporous resin is wide-aperture macromolecule parting material, the enriching and purifying that ability with selective absorption organic compound is applied to the native chemical composition has effect preferably, but its absorption property and desorbing, purification condition parameter are different because of the physicochemical property of chemical compound.
How using macroporous adsorbent resin prepares Chinese medicine test liquid key and is correctly to select the adsorbent resin model to conciliate to smoke concentration of alcohol (eluant).Often select resin such as D101, the AB-8 of nonpolar and low pole in the commercial production for use for preparation liposoluble constituent steroidal class, diterpene and triterpenes, flavone, lignanoid, coumarin, alkaloid, what HP20 was that MIT produces is the adsorbent resin of matrix with polystyrene-based benzene, be a kind of good with adsorbance height, uniform particles, mechanical strength, be difficult for the macroporous adsorbent resin broken, that residue is few, pretreatment is convenient and well-known, so the present invention selects for use the resin of this model of HP20 as chromatographic material.
Ramulus et folium taxi cuspidatae antioxidant content of the present invention adopts silica gel thin-layer chromatography, polyamide thin layer chromatography, utilizes developer to identify; Adopt reversed-phase silica gel column chromatography that eluent Z-4 '/Y-4 ' is separated, adopt the HP-20 gel filtration chromatography that eluent Z-4 '/Y-4 ', Z-3 '/Y-3 ' is separated again, each separation component is carried out qualitative identification, oxidation-resistant active ingredient is mainly polyphenol compound and amino acids in the branch of Ramulus et folium taxi cuspidatae, and oxidation-resistant active ingredient has Polyphenols and flavone compound in the Taxus leaf.
The extraction of Ramulus et folium taxi cuspidatae antioxidant content:
(1) preparation of extractum 1: get branch of Ramulus et folium taxi cuspidatae, impregnated in mass concentration and be in 72% the alcoholic solution, extract with alcoholic solution, the residue medicinal residues continue use water extraction, merge water and alcoholic solution, reflux with petroleum ether, and Soxhlet is extracted the recovery solvent, obtains extractum Z-1;
Or Taxus leaf, the same branch of Ramulus et folium taxi cuspidatae of operating procedure, corresponding extractum is Y-1;
(2) gradient elution: by mass concentration: with the extractum water dissolution of preparation, last HP20 macroporous resin, water liquid, 20% pure liquid, 40% pure liquid, 60% pure liquid in order, 80% pure liquid gradient elution, obtain eluent Z-2 ', Z-3 ', Z-4 ', Z-5 ' and Z-6 ' successively, be product Ramulus et folium taxi cuspidatae antioxidant content; Eluent is 8-10 times of column volume, and flow velocity is 1.2mL/min;
Or Taxus leaf, the same branch of Ramulus et folium taxi cuspidatae of operating procedure, corresponding eluent is followed successively by Y-2 ', Y-3 ', Y-4 ', Y-5 ' and Y-6 ';
Merge and namely get the Ramulus et folium taxi cuspidatae antioxidant content.
Wherein said flavone accounts for 32% of three kinds of composition cumulative volumes, and phenols lignanoid accounts for 47% of cumulative volume, and all the other are tannin.
The extraction of Ramulus et folium taxi cuspidatae antioxidant content:
(1) preparation of extractum 1: get branch of Ramulus et folium taxi cuspidatae, impregnated in mass concentration and be in 70% the alcoholic solution, extract with alcoholic solution, the residue medicinal residues continue use water extraction, merge water and alcoholic solution, reflux with petroleum ether, and Soxhlet is extracted the recovery solvent, obtains extractum Z-1;
Or Taxus leaf, the same branch of Ramulus et folium taxi cuspidatae of operating procedure, corresponding extractum is Y-1;
(2) gradient elution: by mass concentration: with the extractum water dissolution of preparation, last HP20 macroporous resin, water liquid, 25% pure liquid, 45% pure liquid, 65% pure liquid in order, 85% pure liquid gradient elution, obtain eluent Z-2 ', Z-3 ', Z-4 ', Z-5 ' and Z-6 ' successively, be product Ramulus et folium taxi cuspidatae antioxidant content; Eluent is 10 times of column volumes, and flow velocity is 1.5mL/min;
Or Taxus leaf, the same branch of Ramulus et folium taxi cuspidatae of operating procedure, corresponding eluent is followed successively by Y-2 ', Y-3 ', Y-4 ', Y-5 ' and Y-6 ';
Merge and namely get the Ramulus et folium taxi cuspidatae antioxidant content.
Wherein said flavone accounts for 12% of three kinds of composition cumulative volumes, and phenols lignanoid accounts for 44% of cumulative volume, and all the other are tannin.
The extraction of Ramulus et folium taxi cuspidatae antioxidant content:
(1) preparation of extractum 1: get branch of Ramulus et folium taxi cuspidatae, impregnated in mass concentration and be in 75% the alcoholic solution, extract with alcoholic solution, the residue medicinal residues continue use water extraction, merge water and alcoholic solution, reflux with petroleum ether, and Soxhlet is extracted the recovery solvent, obtains extractum Z-1;
Or Taxus leaf, the same branch of Ramulus et folium taxi cuspidatae of operating procedure, corresponding extractum is Y-1;
(2) gradient elution: by mass concentration: with the extractum water dissolution of preparation, last HP20 macroporous resin, water liquid, 15% pure liquid, 35% pure liquid, 55% pure liquid in order, 75% pure liquid gradient elution, obtain eluent Z-2 ', Z-3 ', Z-4 ', Z-5 ' and Z-6 ' successively, be product Ramulus et folium taxi cuspidatae antioxidant content; Eluent is 8 times of column volumes, and flow velocity is 1mL/min;
Or Taxus leaf, the same branch of Ramulus et folium taxi cuspidatae of operating procedure, corresponding eluent is followed successively by Y-2 ', Y-3 ', Y-4 ', Y-5 ' and Y-6 ';
Merge and namely get the Ramulus et folium taxi cuspidatae antioxidant content.
Wherein said flavone accounts for 34% of three kinds of composition cumulative volumes, and phenols lignanoid accounts for 42% of cumulative volume, and all the other are tannin.
In order further to verify the activity of Ramulus et folium taxi cuspidatae extract of the present invention, the inventor has further launched a large amount of tests, because length is limit, it is for reference only to exemplify part herein.
Selection and the foundation of test example 1 Ramulus et folium taxi cuspidatae extract antioxidation assay method
At present, the mensuration of antioxidant activity mainly in antioxidation in vitro system and the body antioxidant system two aspects carry out, the objective of the invention is to develop antidotal cosmetics, so adopt the antioxidation in vitro system.Pass through literature research, the present invention adopts the external spectrophotography DPPH(1 that more generally is used for external test material Total antioxidant capacity now, 1-diphenyl-2-picrylhydrazyl) method is carried out the research of antioxidant activity aspect to composition in the Ramulus et folium taxi cuspidatae, and the DPPH method carried out methodological study, that this law has is highly sensitive, stability and favorable reproducibility, accuracy is high and operate easy characteristics.
The qualitative analysis of test example 2 Ramulus et folium taxi cuspidatae antioxidant contents
Get branch of Ramulus et folium taxi cuspidatae and leaf, branch and leaf separate, and dry in the shade in indoor.
Get branch of Ramulus et folium taxi cuspidatae and Ye Ge 50g after drying in the shade respectively, extract with petroleum ether hot reflux Soxhlet, after petroleum ether extract reclaims solvent, get branch and leaf petroleum ether for examination component Z-1 and Y-1; The residue medicinal residues extract with ethyl acetate hot reflux Soxhlet respectively, get branch and leaves ethyl acetate behind the extracting solution recovery solvent for examination component Z-2 and Y-2; The residue medicinal residues extract with methanol hot reflux Soxhlet respectively, get branch and leaf behind the extracting solution recovery solvent for examination component position Z-3 and Y-3; Residue medicinal residues water hot reflux respectively extract, and evaporating water gets branch and leaf water extract supplies examination component Z-4 and Y-4.(Z1-Z4 and Y1-Y4 are different from embodiment 1 described Z1 '-Z4 ' and Y1 '-Y4 ' herein)
1, the screening of DPPH solution concentration
Draw 0.125mg/mLVC solution (with the dissolving of 100mmol/LpH7.4Tris-HCl buffer) 200 μ l respectively with equal-volume 300,250,200,150,100,50 μ mol/lDPPH solution add in the same tool plug test tube, shake up, after placing 30min in the dark place under the room temperature, measure its absorbance A i with dehydrated alcohol as reference, measure the absorbance A c of variable concentrations DPPH solution and equal-volume dehydrated alcohol mixed liquor simultaneously, and the absorbance A j of VC liquid and equal-volume 100mmol/LTris-HCl buffer (pH7.4) mixed liquor, calculate clearance rate, determination data and result of calculation such as table 1 and Fig. 1.
The screening (Aj is 0.0401) of table 1DPPH solution concentration
As seen 250 μ mol/l-150 μ mol/l are platform area, and choosing interval intermediate value 200 μ mol/L is optium concentration.
2, the screening of DPPH solution application of sample amount
Draw equal-volume 0.125mg/mLVC solution (with the dissolving of 100mmol/LpH7.4Tris-HCl buffer) respectively with 250,200,150,100,50 μ l0.2mmol/LDPPH solution add in the same tool plug test tube, shake up, after placing 30min in the dark place under the room temperature, measure its absorbance A i with dehydrated alcohol as reference, measure the absorbance A c of 0.2mmol/LDPPH solution and equal-volume dehydrated alcohol mixed liquor simultaneously, and the absorbance A j of VC liquid and equal-volume 100mmol/LTris-HCl buffer (pH7.4) mixed liquor, calculate clearance rate, determination data and result of calculation such as table 2 and Fig. 2.
The screening of table 2DPPH solution application of sample amount
Clearance rate is 50% to be to be 150 μ L, and 250uL-200 μ L is more stable, can consider to add 200 μ L.
3, the screening in response time
Drawing 0.125mg/mLVC solution (with the dissolving of 100mmol/LpH7.4Tris-HCl buffer) 200 μ L and equal-volume 0.2mmol/LDPPH solution adds in the same tool plug test tube, shake up, place 10 in the dark place under the room temperature, 15,20,25,30,35, behind the 40min, measure its absorbance A i with dehydrated alcohol as reference, measure the absorbance A c of 0.2mmol/LDPPH solution and equal-volume dehydrated alcohol mixed liquor simultaneously, and the absorbance A j of VC liquid and equal-volume 100mmol/LTris-HCl buffer (pH7.4) mixed liquor, calculate clearance rate, determination data and result of calculation such as table 3.
The screening in response time during table 3DPPH measures
The time simulation of Ramulus et folium taxi cuspidatae antioxidant content qualitative test
Testing sample is configured to five concentration (0.5,0.25,0.125,0.0625,0.03125mg/mL) respectively,
By the described method of 1-3 the sample clearance rate is measured, the result sees table 4, table 5 for details.From having of data visible antioxidant activity more intense (clearance rate being more than 50%): Z-2, Z-3, particularly Z-3 position activity is stronger, with active quite with concentration Vc, the antioxidant activity of leaf relatively a little less than.Contain oxidation-resistant active ingredient in the Ramulus et folium taxi cuspidatae, be worth deeply studying.
Each position antioxidant activity is measured (Ac is 1.445) in table 4 Taxus leaf
Each position antioxidant activity is measured (Ac is 1.404) in table 5 branch of Ramulus et folium taxi cuspidatae
Conclusion: clearance rate is measured and is reached stable behind the 30min, and it is feasible the response time to be set at 30min.
4, method of testing determines
According to literature research and above methodological investigation, determine that the assay method concrete steps are:
Preparation 0.2mmol/LDPPH alcoholic solution, get and treat test sample 200 μ L (with the dissolving of 100mmol/LpH7.4Tris-HCl buffer), the VC(ascorbic acid, positive control, adopt concentration to be respectively 0.44mg/mL, 0.22mg/mL, 0.11mg/mL, 0.055mg/mL, 0.0265mg/mL) and equal-volume 0.2mmol/LDPPH solution add in the same tool plug test tube, shake up, after placing 30min in the dark place under the room temperature, measure its absorbance A i with dehydrated alcohol as reference, measure the absorbance A c of 0.2mmol/LDPPH solution and equal-volume dehydrated alcohol mixed liquor simultaneously, and the absorbance A j of liquid to be measured and equal-volume 100mmol/LTris-HCl buffer (pH7.4) mixed liquor, calculate clearance rate:
DPPH clearance rate %=[1-(Ai-Aj)/Ac] * 100%
Wherein: DPPH solution absorbency when Ac treats test sample for not adding; DPPH solution absorbency when Ai treats test sample for adding; Aj is measuring the wavelength absorbance for treating test sample; The mensuration wavelength is 517nm.
5, adopt the DPPH method to measure the antioxidant activity of embodiment 1 each test sample, the results are shown in Table 6, table 7 and Fig. 3, Fig. 4.
Each position antioxidant activity is measured (Ac is 1.445) in table 6 Taxus leaf
Each position antioxidant activity is measured (Ac is 1.404) in table 7 branch of Ramulus et folium taxi cuspidatae
The result shows: each component antioxidant activity is not of uniform size, and antioxidation is the component of (clearance rate is more than 50%) effectively, and leaf is Y-3, Y-4; Branch is Z-2, Z-3, Z-3 ', Z-4 ', Z-5 ', Z-6 '.
Be 0.5mg/mL at each concentration of component, each component antioxidant activity (clearance rate is more than 40%) size order is: Z-3＞Z-4 '＞Z-3 '＞Y-4 '＞Z-6 '＞Z-2＞Z-5 '＞Y-3 '＞Y-5 '
This shows Z-3, Z-4 ', Z-3 ', Y-4 ' oxidation-resistant active ingredient content height, and the antioxidant activity of branch is better than leaf.
The isolation identification of test example 3 Ramulus et folium taxi cuspidatae oxidation-resistant active ingredients
(1) experiment material and reagent: for trying the component that component is macroporous resin preparation in branch and the leaf, Y-2 '--Y-8 ' and Z-2 '---Z-8 ' thin layer chromatography is Haiyang Chemical Plant, Qingdao with silica gel and produces, and other reagent is analytical pure.
(2) selection of silica gel thin-layer plate developing solvent: developing solvent is the BAW system.
(3) the polyamide ply of paper is analysed the selection of developing solvent: because silica gel thin-layer chromatography is bad to the separating effect of composition, hangover is serious.Fe3Cl3 hydrochloric acid solution colour developing back is illustrated as aldehydes matter for blueness.And the polyamide ply of paper analyses and can be used for phenols, quinones, nitro compound, aminoacid and derivant thereof etc., differentiates so select for use the polyamide ply of paper to analyse, and investigated developing solvent methanol: the optimal proportion of water.
(4) result and analysis:
A, as shown in Figure 5 is silica gel thin-layer chromatography.
Developer: 2%Al3Cl3 alcoholic solution colour developing; The result: visible Y-4 ' has two speckle displaing yellow fluorescence under the ultraviolet, does not have yellow fluorescent substance to occur and have in the branch; Conclusion: contain flavone compound among the Y-4 '.
B, as shown in Figure 6, silica gel thin-layer chromatography.
Developing solvent: BAW (4:1:5) upper strata liquid; Developer: 1,2,3-indantrione monohydrate colour developing; It is light yellow that result: Z-3 ', Z-4 ' show; Contain amino acids among conclusion: Z-3 ', the Z-4 '.
C, C, as shown in Figure 7, silica gel thin-layer chromatography.
Developing solvent: BAW (4:1:5) upper strata liquid; Developer: 1,2,3-indantrione monohydrate colour developing; It is light yellow that result: Z-3 ', Z-4 ' show; Contain amino acids among conclusion: Z-3 ', the Z-4 '.
D, as shown in Figure 8, the polyamide ply of paper is analysed.
Developing solvent: methanol: water (40:1); Left side developer: Fe3Cl3 hydrochloric acid solution colour developing; Right developer: 2%Al3Cl3 alcoholic solution colour developing; Contain Polyphenols among conclusion: Z-3 ', the Z-4 ', contain flavone and polyphenol among the Y-4 ', contain polyphenol among the Y-3 '; By test result demonstrate the Ramulus et folium taxi cuspidatae antioxidant content mainly be Polyphenols and amino acids and in the leaf active component be mainly Polyphenols and flavonoid.
Antioxidation is the component of (clearance rate is more than 50%) effectively, and leaf is Y-3 ', Y-4 '; Branch is Z-3 ', Z-4 ', Z-5 ', Z-6 ', be 0.5mg/mL at each concentration of component, the descending order of each component antioxidant activity size of macroporous resin column chromatography is: Z-4 '＞Z-3 '＞Y-4 '＞Z-6 '＞Z-5 '＞Y-3 ', and Z-5 ', Z-6 ' antioxidant activity are than weak many of Z-3 ', Z-4 ', so the present invention further carries out separation and purification to Z-3 ', Z-4 ' and the strong position of Y-4 ' antioxidant activity.
The isolation identification of test example 4 component Y-4 ' active component
(1) experiment material and reagent: for trying the component Y-4 ' that component is macroporous resin preparation in branch and the leaf, the column chromatography filler is that Canadian silicycleODS reverse phase filler specification is 120A, 50um, and other reagent is analytical pure.
(2) reversed phase column chromatography separates: the ODS reverse phase filler with dissolve with methanol after, soaked overnight, the glaze post, successively with 80%, 60%,, 40%, 20% methanol solution, clean with aqueous solution at last, after 10% methanol aqueous solution sample dissolution, gently flow in the reverse phase silica gel post, successively with 10%, 20%, 40%, 60%, 80% methanol solution gradient elution, use methanol-eluted fractions at last, the amount of solution that 10% methanol solution eluting comes out is very big, the solution concentration that elutes, qualitative discriminating usefulness is treated in the merging that thin layer chromatography is identical.
(3) result and analysis: the component silica gel thin-layer that elutes differentiates that developing solvent is the BAW system.Spray 2%Al3Cl3 alcoholic solution, displaing yellow fluorescence has 3 speckles under ultraviolet.
As shown in Figure 9, silica gel thin-layer chromatography.
Developer: 2%Al3Cl3 alcoholic solution colour developing; The result: the fraction that as seen elutes under the ultraviolet has 3 speckle displaing yellow fluorescence; Conclusion: contain flavone compound among the Y-4 '
The isolation identification of test example 5 component Z-3 ', Z-4 ' active component
(1) experiment material and reagent: for trying component Z-3 ', the Z-4 ' that component is macroporous resin preparation in branch and the leaf, the column chromatography filler is SephadexLH-20, and other reagent is analytical pure.
(2) SephadexLH-20 chromatography: SephadexLH20 is the higher filler of a kind of price, and its separation principle mainly contains two aspects: act as the master with gel filtration, have the effect (in anti-phase solvent) of anti-phase distribution concurrently.Because the gel filtration effect, so a little less than macromolecular chemical compound keeps, eluted earlier, micromolecular chemical compound keeps strong, goes out post at last.If use anti-phase solvent elution, the chemical compound of SephadexLH20 also plays anti-phase distribution, so a little less than the big chemical compound of polarity keeps, eluted earlier, the chemical compound that polarity is little keeps strong, after go out post.
The selection of SephadexLH20 eluting solvent is divided into two classes according to its eluting principle: anti-phase and two kinds of solvents of positive.With the most use is anti-phase solvent elution, the most common with the methanol-water system, and first water increases the methanol ratio gradually, uses 100% methanol towards post at last.
Component Z-3 ', Z-4 ' polarity are bigger, so adopt anti-phase solvent elution.Filler with dissolve with methanol after, soaked overnight, the glaze post, successively use 80%, 60%,, 40%, 20% methanol solution, clean with aqueous solution at last, after 10% methanol aqueous solution sample dissolution, gently flow in the reverse phase silica gel post, successively use 10%, 20%, 40%, 60%, 80% methanol solution gradient elution, use methanol-eluted fractions at last, the solution concentration that elutes, qualitative discriminating usefulness is treated in the merging that thin layer chromatography is identical.
(3) result and analysis: the component polyamide ply of paper that elutes is analysed discriminating, and developing solvent is the methanol-water system.As shown in figure 10, developer: Fe3Cl3 hydrochloric acid solution; Result: contain several polyphenol monomers in the elution fraction; Contain polyphenol compound among conclusion: Z-3 ', the Z-4 '.
The assay of Application Example 6 Ramulus et folium taxi cuspidatae oxidation-resistant active ingredient polyphenol
(1) medical material, reagent and instrument
Medical material: the branch of Ramulus et folium taxi cuspidatae after drying in the shade and leaf are pulverized with pulverizer respectively, cross 80 mesh sieves, are dried to constant weight under exsiccator, and be standby for content measuring.
Reagent: 20% Na2CO3, Folin reagent, the 0.1mg/mL gallic acid, other reagent are analytical pure.
Instrument: BS1IOS electronic balance (Beijing Sai Duolisi company), SpectrumIab22 visible spectrophotometer (Shanghai rib light company), CS101 type electric drying oven with forced convection (Chongqing testing equipment factory), KQ-400DB ultrasonic cleaner (Kunshan Ultrasonic Instruments Co., Ltd.).
(2) testing procedure is as follows:
The preparation of a, standard solution: be reference substance with the gallic acid, accurately take by weighing the 0.0025g gallic acid, distilled water is settled to 25mL.This concentration of standard solution is 0.1mg/mL.
The mensuration of b, maximum absorption wavelength: be solvent with the distilled water, be developer with Folin reagent, sodium carbonate, make the absorption curve of standard substance gallic acid, its absorbance of scanning under the 740-790nm wavelength, the result shows at the 765nm place strong absworption peak, so select 765nm for measuring wavelength.
The foundation of c, standard curve: accurately measure above-mentioned titer 0,0.1,0.2,0.3,0.4,0.5,0.6,0.7,0.8mL in the 10mL volumetric flask, respectively add 6mL water, shake up, add the 0.5mL Folin reagent again, fully shake up.After the lmin, add sodium carbonate liquor (20g sodium carbonate/100mL water) 1.5mL, the mixing standardize solution.React 10min (1 hour at normal temperatures) down at 75 ℃, under the 765nm wavelength, measure absorbance, set up standard curve.
The preparation of d, sample solution: accurately take by weighing a coarse powder 0.2000g, be placed in the 25mL volumetric flask, add 65% ethanol standardize solution.Use ultrasonic extraction 30min, get the 1mL supernatant after leaving standstill 10min, in the 10mL volumetric flask, be settled to scale with 65% ethanol, as test solution Z-1.
Accurately take by weighing leaf coarse powder 0.2000g, be placed in the 25mL volumetric flask, add 65% ethanol standardize solution.Use ultrasonic extraction 30min, get the 1mL supernatant after leaving standstill 10min, in the 10mL volumetric flask, be settled to scale with 65% ethanol, as test solution Y-1.
Accurately take by weighing Z-3 ', the Z-4 ', Z-5 ', Z-6 ', Y-3 ', Y-5 ' the coarse powder 0.0050g that are dried to constant weight respectively, be placed in the 50mL volumetric flask, add 65% ethanol standardize solution.
Accurately take by weighing Y-4 ' the coarse powder 0.00412g that is dried to constant weight, be placed in the 50mL volumetric flask, add 65% ethanol standardize solution.
The mensuration of e, sample: accurately measure the sample solution lmL for preparing in the 10mL volumetric flask, add the 6mL distilled water, add the 0.5mL Folin reagent again, add 1.5mL20%NaCO3 solution again, water is settled to scale, mixing behind 75 ℃ of water-bath 10min, is determined at the absorbance at 765nm place after the cooling.
(3) result and discussion
Shown in Figure 11 and table 8, gallic acid is linear at concentration 0-80 μ g/mL internal absorbance and concentration, is y=0.0128x-0.0211 at this scope internal regression equation, and R2=0.9984 shows that linear relationship is good.
Table 8 sample size measurement result
| Sample number into spectrum | Absorbance | Concentration (μ g/mL) | Percentage composition (%) |
| Y-1 | 0.220 | 18.850 | 2.35 |
| Y-3’ | 0.316 | 26.423 | 26.42 |
| Y-4’ | 0.281 | 23.669 | 28.72 |
| Y-5’ | 0.191 | 16.613 | 16.61 |
| Z-1 | 0.311 | 26.039 | 3.25 |
| Z-3’ | 0.638 | 51.602 | 51.60 |
| Z-4’ | 0.596 | 48.329 | 48.33 |
| Z-5’ | 0.490 | 40.052 | 40.05 |
| Z-6’ | 0.309 | 25.863 | 25.86 |
Each component polyphenol content size order is: Z-3 '＞Z-4 '＞Z-5 '＞Y-4 '＞Y-3 '＞Z-6 '＞Y-5 '; And be 0.5mg/mL at each concentration of component, each component antioxidant activity (clearance rate is more than 40%) size order is: Z-4 '＞Z-3 '＞Y-4 '＞Z-6 '＞Z-5 '＞Y-3 '＞Y-5 '.The position that polyphenol content is high, its antioxidant activity are also stronger relatively.
Test example 7 and combination of proteins
In the quintessence oil of releiving, add the Ramulus et folium taxi cuspidatae antioxidant content of 5% embodiment, 1 gained, after tested, it has good adhesive ability to skin under anti-water condition, and thick pore is shunk, make lax skin-tightening and around reducing, also can reduce the transition secretion of greasy skin sebum.
Get 50gSiO2 and be to mix in 10% the elastin laminin aqueous solution in 45g concentration, mix in 40 ℃ with 100g Ramulus et folium taxi cuspidatae antioxidant content again, vacuum drying, pulverize wherein contains cellular elastin laminin-tannin complex after tested.It is the main component of beauty and skin care, to the skin nonirritant, and has the effect of medium astringent, and good water proofing property, certain humidity and skin attachment are also arranged simultaneously.
Test example 8 oxidation resistances
Test example 9 ultra-violet radiation resisting abilities
Test has been added the sunscreen cream of embodiment 1 gained Ramulus et folium taxi cuspidatae antioxidant content at the assimilation effect of ultra-violet (UV) band.Because Flavonoid substances is variant at the maximum absorption band of ultraviolet region, therefore specially comments through composite China and may play the sun-proof effect of wide spectrum.After human body is filmed, ultraviolet absorbance is reached more than 98%, even the harm that also can avoid ultraviolet radiation to bring under high light all has the effect significantly resisted to Exposure to Sunlight dermatitis and multiple mottle symptom.
Test example 10 reduces melanin content
Get the Ramulus et folium taxi cuspidatae antioxidant content of embodiment 1 preparation, purify, when concentration is 0.01-1.0mmol, can reduce tyrosinase activity, suppress melanic formation, effect is better than kojic acid and Vc, can significantly reduce melanic amount in concentration during for 0.5mmol.
Though, above used general explanation, the specific embodiment and test, the present invention is described in detail, on basis of the present invention, can make some modifications or improvements it, and this will be apparent to those skilled in the art.Therefore, these modifications or improvements all belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (9)
1. Ramulus et folium taxi cuspidatae extract with antioxidation, it is characterized in that: branch and/or leaf with Taxus mairei are that feedstock production forms, comprise 12% ~ 58% flavone in the described Ramulus et folium taxi cuspidatae extract, 9% ~ 47% phenols lignanoid, all the other are tannin.
2. Ramulus et folium taxi cuspidatae extract as claimed in claim 1, it is characterized in that: described flavone comprises kaempferol.
3. Ramulus et folium taxi cuspidatae extract as claimed in claim 1 is characterized in that: described phenols lignanoid comprises (-)-alpha-Conidendrin.
4. the extracting method of each described Ramulus et folium taxi cuspidatae extract of claim 1-3 is characterized in that: comprise the steps:
(1) preparation extractum: get branch of Ramulus et folium taxi cuspidatae and/or leaf, impregnated in the alcoholic solution that mass concentration is 70%-75%, extract with alcoholic solution, the residue medicinal residues continue to use water extraction, merge water and alcoholic solution, reflux with petroleum ether, and Soxhlet is extracted and reclaimed solvent, obtains extractum;
(2) gradient elution: with the extractum water dissolution, last HP20 macroporous resin, the pure liquid of the pure liquid of the pure liquid of water, 15-25%, 35-45%, 55-65% in order, the pure liquid gradient elution of 75-85%, collection also merges each eluent, namely gets Ramulus et folium taxi cuspidatae extract.
5. extracting method as claimed in claim 2, it is characterized in that: each eluent is respectively water liquid, 20% pure liquid, 40% pure liquid, 60% pure liquid, 80% pure liquid in the step 2.
6. extracting method as claimed in claim 2, it is characterized in that: the consumption of each eluent is 8-10 times of column volume in the step 2, and flow velocity is 1-1.5mL/min.
7. as the extracting method of Ramulus et folium taxi cuspidatae extract as described in the claim 2, it is characterized in that: the alcohol in described step 1 and the step 2 is ethanol.
8. as the extracting method of Ramulus et folium taxi cuspidatae extract as described in the claim 2, it is characterized in that: described extracting method also comprises Ramulus et folium taxi cuspidatae extract concentrated and desolventizes the step that obtains extract extractum.
9. each described Ramulus et folium taxi cuspidatae extract of claim 1-3 is as the application of active component in the antioxidation cosmetics.
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| CN105265575A (en) * | 2015-09-17 | 2016-01-27 | 邯郸学院 | Dandelion extract with functions of scavenging free radicals and preventing mildew |
| CN109562055A (en) * | 2016-07-01 | 2019-04-02 | 汤姆凯特国际公司 | For fighting the composition of skin, hair and nail aging sign |
| CN109562055B (en) * | 2016-07-01 | 2023-04-04 | 汤姆凯特国际公司 | Composition for combating the signs of skin, hair and nails ageing |
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