CN103585216A - Use of C21 steroidal glycoside of root tubers of Cynanchun auriculatum Royle ex Wight, Cynanchum bungei Decne and Cynanchum wifordii Hemsl in activation of tyrosinase - Google Patents
Use of C21 steroidal glycoside of root tubers of Cynanchun auriculatum Royle ex Wight, Cynanchum bungei Decne and Cynanchum wifordii Hemsl in activation of tyrosinase Download PDFInfo
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- CN103585216A CN103585216A CN201310636896.8A CN201310636896A CN103585216A CN 103585216 A CN103585216 A CN 103585216A CN 201310636896 A CN201310636896 A CN 201310636896A CN 103585216 A CN103585216 A CN 103585216A
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Abstract
The invention relates to a use of C21 steroidal glycoside (C21 steroidal glycoside A) extracted and separated from root tubers of Cynanchun auriculatum Royle ex Wight, Cynanchum bungei Decne and Cynanchum wifordii Hemsl in activation of tyrosinase. The C21 steroidal glycoside has a strong activation effect on mushroom tyrosinase diphenolase and can be used in the related field. The invention illustrates the novel purpose of the C21 steroidal glycoside in the field of medicine and daily-use chemical industry. The influence produced by the C21 steroidal glycoside A of root tubers of Cynanchun auriculatum Royle ex Wight, Cynanchum bungei Decne and Cynanchum wifordii Hemsl on the vitality of the tyrosinase diphenolase is detected through an enzymatic reaction, and the result shows that the C21 steroidal glycoside A has strong effects of activation of mushroom tyrosinase diphenolase and has a tyrosinase activation rate of 293.28% based on the final concentration of 0.05mg/ml, and the C21 steroidal glycoside A contains different active components having competitive and non-competitive dual activation effects on tyrosinase and has a mixed activation type. The C21 steroidal glycoside A of root tubers of Cynanchun auriculatum Royle ex Wight, Cynanchum bungei Decne and Cynanchum wifordii Hemsl can be used for preparation of drugs for treating pigment deletion-caused diseases and can also be used for preparation of daily chemical articles for blacking skin and hair.
Description
Technical field
The present invention relates to C in a kind of Radix Cynanchi Auriculati
21the purposes of sterioside to tryrosinase activation.The present invention relates to a kind of C extracting, separation obtains from Chinese medicine Radix Cynanchi Auriculati
21sterioside has very strong activation to tryrosinase, illustrated its preparation method and medicine, filed of daily-use chemical industry new purposes.
Background technology
Tryrosinase is a kind of polyphenol oxidase of cupric, and it is the rate-limiting enzyme in organism melanocyte building-up process, and catalytic tyrosine hydroxylation is that DOPA, dopa oxidase are that DOPA quinone and 5,6-dihydroxy indole (DHI) are oxidized to three steps of 5,6-istain.It is expressed and active amount and the speed that is determining that melanin generates.Reacted by force and can cause melanism, as freckle, chloasma etc., it is too much the basic reason that chloasma forms that melanin generates; Reacted weak or lacked reaction, can cause poliosis, vitiligo etc.In the ball top of middle-aged and elderly people poliosis person hair follicle, tyrosinase activity is lost gradually in melanocyte, and synthetic melanocyte ability weakens gradually and even disappears, so pigment disappears and bleaches in hair; In vitiligo skin lesion place melanocyte, melanocyte reduces even disappearance, and vitiligo active stage melanocyte density reduces.The activity of tryrosinase determining melanic synthetic and synthetic quantity number, promotes its activity can make melanin generate and increase, thereby treatment pigment disappearance property disease is as poliosis, vitiligo etc.
Radix Cynanchi Auriculati derives from the tuber of Asclepiadaceae Cynanchum 3 kind of plant [being respectively cynanchum auriculatum Royle (Cynanchum auriculatum Royle ex Wight), Bunge Swallowwort Root (Cynanchum bungei Decne) and Radix cynanchi wilfordii (Cynanchum wifordii Hemsl)], be clinical conventional tonification and delay aging drug, be just regarded as since ancient times the treasure of anti-old, the beneficial intensive culture face of health preserving.Modern study is found to contain various active composition in Radix Cynanchi Auriculati, as C
21sterioside, polysaccharide, phospholipid etc.As the patent " purposes of extractive of radix cynanchi bungei total glucoside in pharmacy " that notification number is 101002836B has been invented the purposes of extractive of radix cynanchi bungei total glucoside for the preparation of the medicine for the treatment of or prevention of depression; Notification number is that 100429217 patent " Radix Cynanchi Auriculati saponin compound, total saponins and the application in treatment gastroenteropathy medicine thereof " finds that Radix Cynanchi Auriculati carbon-21 steroidal saponin and radix cynanchi bungei total saponin are the medicines of effectively treating gastritis, gastric duodenal ulcer, prevention ulcer recurrence, improving gastrointestinal tract dynamia; Notification number is extracorporeal anti-tumor function and the purposes that the patent " in Radix Cynanchi Auriculati new compound kidjolanin 3-O-β-Apocynum cannabinum glucosides and uses thereof " of 101029069B has been found this compound.In addition, notification number is that the patent " tuber fleeceflower root hair blackening formula and preparation method thereof " of 102068401B has been invented and with the Chinese medicine composition headed by Radix Polygoni Multiflori, Semen Sesami Nigrum, by raising, activated tyrosinase activity and melanin formation promoting in hair follicle and reach pitch-black hair, improve the objects such as early whitening of beard and hair, but Radix Polygoni Multiflori wherein belongs to different kinds in plant from Radix Cynanchi Auriculati.There is no at present the C extracting in Radix Cynanchi Auriculati medical material
21sterioside has the report that strengthens tyrosinase activity associated uses.
Summary of the invention
The object of the invention is to: C in a kind of Radix Cynanchi Auriculati is provided
21the new purposes of sterioside.A kind of C in Radix Cynanchi Auriculati of the present invention
21sterioside has significant tryrosinase activation, can be used for the medicine of preparation treatment pigment disappearance property disease (as poliosis, vitiligo etc.), also can be used for preparing that skin U.S. is black, the cosmetics of everyday use of black hair.
The present invention is achieved through the following technical solutions:
Described Radix Cynanchi Auriculati C
21sterioside is preparation like this: Radix Cynanchi Auriculati powder adds 95% alcohol heating reflux 3h, filters and obtains alcohol extract, and concentrating under reduced pressure, room temperature obtain ethanol extract after volatilizing solvent.This extract is dissolved in to methanol: in the solution that water (volume ratio) is 9:1, with petroleum ether jolting defat 3 times, raffinate adds appropriate distilled water concentrating under reduced pressure and reclaims methanol, with chloroform, repeatedly extracts.Chloroform extraction liquid is merged, drip in 5 times of petroleum ether after being concentrated into small size, dispersed with stirring, separates out precipitate, and filtration drying obtains total sterioside.Total sterioside is dissolved with a small amount of chloroform, pass through silica gel column chromatography, use successively chloroform (I), chloroform: methanol (volume ratio) is 98:2 (II), 95:5 (III), 90:10 (IV), and five gradients of methanol (V) are carried out eluting.Eluent is revolved to steaming, volatilize eluant, get appropriate total sterioside and each elution fraction and be dissolved in solvent (propylene glycol: ethyl acetate: phosphate buffer volume ratio is 9:1:18) and make sample solution, concentration is 1mg/mL.
Radix Cynanchi Auriculati C
21sterioside affects tryrosinase vigor testing methods: getting concentration is radix cynanchi bungei total sterioside and each elution fraction solution 50 μ L of 1mg/mL (final concentration in reaction system is 0.2mg/mL), and be diluted in right amount 140 μ L with pH6.8 phosphate buffer, 50 μ L mix with tryrosinase liquid (25U/mL), in 37 ℃, hatch 5min, the levodopa solution 60 μ L that add 15mmol/L, continue to hatch 2min, immediately in microplate reader 492nm place's photometry absorption value and calculate tryrosinase activity ratio.Radix cynanchi bungei total sterioside has reached 49.97% in 1mg/mL (final concentration 0.2mg/mL) level to the activity ratio of tryrosinase, No. 4 eluate (C of column chromatography
21sterioside A) in 1mg/mL (final concentration 0.2mg/mL) level, to the activity ratio of tryrosinase, being 165.49%, is 293.28% and the activity ratio during in same concentration is 102.27% as positive control Fructus Psoraleae ethanol extraction in 0.25mg/mL (final concentration 0.05mg/mL) level to the activity ratio of tryrosinase.
Radix Cynanchi Auriculati C provided by the invention
21sterioside A is as the high activity composition that activates tryrosinase, can add acceptable carrier on one or more pharmaceuticss, carrier comprises the diluent of pharmaceutical field routine, excipient, filler, binding agent, wetting agent, disintegrating agent, absorption enhancer, absorption carrier, lubricant, osmotic pressure regulator, can also add flavouring agent, sweeting agent etc. if desired, preparation method according to the preparation of recording on pharmaceutics is made preparation, is used for the treatment of pigment disappearance property disease as needed the disease of activity of tyrosinase as poliosis, vitiligo etc. and other.Described preparation comprises granule, tablet, electuary, powder, oral liquid, sugar coated tablet, film coated tablet, capsule, sucks agent, granule, pill, unguentum, sublimed preparation, spray, drop pill, disintegrating agent, oral cavity disintegration tablet, micropill, externally used solution agent etc.
Radix Cynanchi Auriculati C provided by the invention
21sterioside A also can be used for preparing that skin U.S. is black, the cosmetics of everyday use of black hair has no particular limits on formula, can be made into solution, Emulsion, cream, facial film, gel, foundation cream, spray etc.
Compared with prior art, the invention has the beneficial effects as follows: the Radix Cynanchi Auriculati C with tryrosinase activation providing
21sterioside A has some new purposes, can be used for the medicine of preparation treatment pigment disappearance property disease, also can be used for preparing that skin U.S. is black, the cosmetics of everyday use of black hair.Because its tryrosinase activation is very strong, exceeded current conventional Fructus Psoraleae, efficient for the preparation of medicine; For the preparation of the less and successful of cosmetics of everyday use consumption, production cost is lower.
Accompanying drawing explanation
The activity ratio of each eluate of Fig. 1 silica gel column chromatography to tryrosinase
Fig. 2 C
21(1 representative of figure cathetus does not add C to the kinetic curve of sterioside A activation tryrosinase
21the enzymatic reaction curve of sterioside A, 2 representatives of figure cathetus add C
21the enzymatic reaction curve of sterioside A)
The specific embodiment
By following examples, further describe for example the present invention, and do not limit the present invention in any way, for a person skilled in the art, all similar replacements and modification are obviously all thought within the scope of spirit of the present invention, scope and design and claim.Any change that those of ordinary skills made for the present invention easily realize or change do not deviating under the prerequisite of technical solution of the present invention, within all will fall into claims limited range of the present invention.
The preparation of radix cynanchi bungei total sterioside: take Radix Cynanchi Auriculati powder 500g, add 1.5L95% alcohol heating reflux 3h, filter and obtain alcohol extract.Extracting solution is through concentrating under reduced pressure, and room temperature volatilizes after solvent, obtains ethanol extract.This extract is dissolved in to methanol: in the solution that water (volume ratio) is 9:1, with petroleum ether jolting defat 3 times, raffinate adds appropriate distilled water concentrating under reduced pressure and reclaims methanol, with chloroform, repeatedly extracts.Chloroform extraction liquid is merged, drip in 5 times of petroleum ether after being concentrated into small size, dispersed with stirring, separates out precipitate, and filtration drying obtains total sterioside, gets a little and carries out respectively Liebermann-Burchard reaction and Keller-Kiliani reaction, all presents strong positive.With ultraviolet spectrophotometry, record C in total sterioside
21the content of sterioside is 85.2% (by pregnenolone).
The silica gel column chromatography of radix cynanchi bungei total sterioside: total sterioside is dissolved with a small amount of chloroform, pass through silica gel column chromatography, use successively chloroform (I), chloroform: methanol (volume ratio) is 98:2 (II), 95:5 (III), 90:10 (IV), and five gradients of methanol (V) are carried out eluting.Eluent is revolved to steaming, volatilize eluant, get appropriate total sterioside and each elution fraction and be dissolved in solvent (propylene glycol: ethyl acetate: phosphate buffer volume ratio is 9:1:18) and make sample solution, concentration is 1mg/mL.
Embodiment 3
The preparation of Fructus Psoraleae ethanol extract: take appropriate Malaytea Scurfpea Fruit, Fructus Psoraleae and 50% ethanol are in the ratio of 1:6, and merceration extracts 3 times, and extracting solution concentrates evaporate to dryness.Get appropriate extract and be dissolved in solvent, the concentration of obtain solution is 0.5mg/mL, as positive control solution.
Radix cynanchi bungei total sterioside and C
21sterioside affects tryrosinase vigor experimental technique:
Reagent: Mushroom Tyrosinase (EC.1.14.18.1 is 5370U/mg than vigor) and levodopa (l-dopa) are Sigma company product, and other reagent (AR level) are Solution on Chemical Reagents in Shanghai company of traditional Chinese medicines group product.
Instrument: AL104 type electronic analytical balance, prunus mume (sieb.) sieb.et zucc. Teller-Tuo benefit (Shanghai) Instrument Ltd. manufactures; The multi-functional microplate reader of Muitiskan MK3, Shanghai Lei Bo Analytical Instrument Co., Ltd product.
Tryrosinase dissolves and is mixed with 500U/mL solution with phosphate buffer, and packing is frozen, before experiment, with phosphate buffer dilution, is that 25U/mL is standby.Before experiment, take appropriate levodopa, with phosphate buffer, dissolve preparation 15mmol/L solution, jolting, standby after fully dissolving.Getting concentration is radix cynanchi bungei total sterioside and each elution fraction solution 50 μ L of 1mg/mL (final concentration in reaction system is 0.2mg/mL), with pH6.8 phosphate buffer, be diluted in right amount 140 μ L, 50 μ L mix with tryrosinase liquid (25U/mL), in 37 ℃, hatch 5min, the levodopa solution 60 μ L that add 15mmol/L, continue to hatch 2min, immediately in microplate reader 492nm place's photometry absorption value C.If replace tryrosinase liquid 50 μ L with phosphate buffer 50 μ L, the absorbance value recording is D; If 50 μ L replace testing sample solution 50 μ L with phosphate buffer, the absorbance value recording is A; If 00 μ L replaces testing sample solution 50 μ L and tryrosinase liquid 50 μ L with phosphate buffer 1, the absorbance value recording is B.Sample calculates as follows to tryrosinase activity ratio:
Enzyme activity ratio (%)=[(C-D)-(A-B)]/(A-B) * 100
In formula: A=A
492-medicine+enzyme=0.126; Containing substrate and enzyme, do not add the reacted absorbance value of testing sample;
B=A
492-medicine-enzyme=0.007; Containing substrate, do not add the absorbance value of testing sample and enzyme;
C=A
492+ medicine+enzyme; Containing substrate and enzyme, add the reacted absorbance value of testing sample;
D=A
492+ medicine-enzyme.Containing substrate and testing sample, not enzyme-added absorbance value.
Experimental result is shown in Fig. 1, and radix cynanchi bungei total sterioside has reached 49.97% in 1mg/mL (final concentration 0.2mg/mL) level to the activity ratio of tryrosinase, No. 4 eluate (C of column chromatography
21sterioside A) in 1mg/mL (final concentration 0.2mg/mL) level, to the activity ratio of tryrosinase, be 165.49%, in each eluate to the powerhouse of the activation of tryrosinase.
Embodiment 5
Radix Cynanchi Auriculati C
21sterioside A activates tryrosinase dose-effect relationship experimental technique: by No. 4 eluate (C
21sterioside A) with above-mentioned solvent dilution, be 0.5mg/mL, get respectively 3,6,12.5,25 and 50 μ L, with pH6.8 phosphate buffer, being diluted to 140 μ L mixes with tryrosinase liquid (25U/mL) 50 μ L, in 37 ℃, hatch 5min, the levodopa solution 60 μ L that add 15mmol/L, continue to hatch 2min, immediately in microplate reader 492nm place's photometry absorption value, tryrosinase activity ratio calculates by above-mentioned formula.And with the comparison of Fructus Psoraleae ethanol extraction.
Experimental result is in Table 1, C
21sterioside A is in certain concentration range, and along with the increase of dosage, activation strengthens, and shows enzymatic activity to be dose dependent activation.C
21sterioside A is 344.54% in 0.5mg/mL (final concentration 0.1mg/mL) level to the activity ratio of tryrosinase, in 0.25mg/mL (final concentration 0.05mg/mL) level, to the activity ratio of tryrosinase, be 293.28%, and the leukodermic conventional Chinese medicine Fructus Psoraleae ethanol extraction of same conduct treatment reaches the highest in 0.25mg/mL (final concentration 0.05mg/mL) level to the activity ratio of tryrosinase, be 102.27%, hence one can see that, the C of same concentration
21sterioside A is stronger than Fructus Psoraleae ethanol extraction to the activation of tryrosinase.
Table 1C
21sterioside A affects measurement result to tyrosinase activity
Radix Cynanchi Auriculati C
21sterioside A is to tryrosinase activation Exploration of Mechanism: get No. 4 eluate dose,optimums and tryrosinase 50 μ L (25U/mL) mixed, hatch 5min for 37 ℃, adding respectively the levodopa solution of different volumes and phosphate buffer to make cumulative volume is 250 μ L, continue to hatch 2min, immediately in microplate reader 492nm place's photometry absorption value.Inverse (1/A) with absorbance value is made Lineweaver-Burk curve to the inverse of concentration of substrate (1/S), with meeh's formula calculating K m.Sample extraction thing adopts the two counting backward technique mapping of Lineweaver-Burk judgement to Inhibition of Tyrosinase Activity type of action.
Experimental result, in Table 2 and Fig. 2, adds as seen and does not add C
21there were significant differences in the enzymatic reaction of sterioside A.From known Km/Km '=2.27 of kinetic curve, show C
21sterioside A makes tryrosinase to the affinity of Binding Capacity, improve 2.27 times, deducibility C
21in sterioside A, some composition is to the competitive activation of tryrosinase; It has improved the enzymatic reaction speed of tryrosinase simultaneously, and V '/V=2.70, shows C
21though in sterioside A, some composition does not affect substrate and is combined with enzyme, can be combined with enzyme-substrate complex and increase maximum reaction velocity, and tryrosinase is had to noncompetitive activation.C is described
21sterioside A contains and different activities component noncompetitive dual activation competitive to tryrosinase, and it activates type and shows as mixed type.
Table 2C
21the kinetic determination result of sterioside A on tyrosinase activity impact
Embodiment 7
Get Radix Cynanchi Auriculati C
21sterioside A is dissolved in solvent (propylene glycol: ethyl acetate: phosphate buffer volume ratio is 9:1:18) and makes solution, and concentration is 0.025mg/mL, for therapy of vitiligo, and outer painting skin lesion place, every day 3 times.
Claims (4)
1. the C in Radix Cynanchi Auriculati source
21sterioside, thus it is characterized in that owing to having very strong activation to can be applicable to association area to Mushroom Tyrosinase diphenol enzyme activity.
2. Radix Cynanchi Auriculati C according to claim 1
21the application of the association area of sterioside, is characterized in that can be used for the medicine of preparation treatment pigment disappearance property disease (as poliosis, vitiligo etc.), also can be used for preparing that skin U.S. is black, the cosmetics of everyday use of black hair.
3. Radix Cynanchi Auriculati C according to claim 2
21sterioside is for the preparation of the medicine for the treatment of pigment disappearance property disease, it is characterized in that as the high activity composition that activates tryrosinase, can add acceptable carrier on one or more pharmaceuticss, carrier comprises the diluent of pharmaceutical field routine, excipient, filler, binding agent, wetting agent, disintegrating agent, absorption enhancer, absorption carrier, lubricant, osmotic pressure regulator, can also add flavouring agent if desired, sweeting agent etc., preparation method according to the preparation of recording on pharmaceutics is made preparation, be used for the treatment of pigment disappearance property disease as poliosis, vitiligo etc. and other need the disease of activity of tyrosinase.Described preparation comprises granule, tablet, electuary, powder, oral liquid, sugar coated tablet, film coated tablet, capsule, sucks agent, granule, pill, unguentum, sublimed preparation, spray, drop pill, disintegrating agent, oral cavity disintegration tablet, micropill, externally used solution agent etc.
4. Radix Cynanchi Auriculati C according to claim 2
21sterioside is black for the preparation of skin U.S., the cosmetics of everyday use of black hair, it is characterized in that having no particular limits on formula, can be made into solution, Emulsion, cream, facial film, gel, foundation cream, spray etc.
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| CN112588318A (en) * | 2020-12-15 | 2021-04-02 | 江南大学 | Green and efficient preparation method of short-sugar-chain C21 steroid glycoside of radix cynanchi bungei |
| CN113318026A (en) * | 2021-06-15 | 2021-08-31 | 福州膳柏健康产业有限公司 | Formula of traditional Chinese medicine hair care liquid for enhancing tyrosinase activity |
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| CN112588318A (en) * | 2020-12-15 | 2021-04-02 | 江南大学 | Green and efficient preparation method of short-sugar-chain C21 steroid glycoside of radix cynanchi bungei |
| CN112588318B (en) * | 2020-12-15 | 2022-02-15 | 江南大学 | Green and efficient preparation method of short-sugar-chain C21 steroid glycoside of radix cynanchi bungei |
| CN113318026A (en) * | 2021-06-15 | 2021-08-31 | 福州膳柏健康产业有限公司 | Formula of traditional Chinese medicine hair care liquid for enhancing tyrosinase activity |
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