CN103655221A - New application of phytosterol functioning as elastinase activity inhibitor, and composition containing the same - Google Patents

New application of phytosterol functioning as elastinase activity inhibitor, and composition containing the same Download PDF

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Publication number
CN103655221A
CN103655221A CN201210391238.2A CN201210391238A CN103655221A CN 103655221 A CN103655221 A CN 103655221A CN 201210391238 A CN201210391238 A CN 201210391238A CN 103655221 A CN103655221 A CN 103655221A
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skin
plant sterol
preparation composition
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phytosterol
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具昌燮
金珉珍
郑伦朱
张东逸
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COTDE Ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
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  • Steroid Compounds (AREA)
  • Cosmetics (AREA)

Abstract

The invention is designed based on the elastinase deactivation research for phytosterols and relates to the new application of a phytosterol functioning as an elastinase activity inhibitor, and an external-use agent composition containing the same and capable of improving the skin elasticity and healing skin wounds. The phytosterol-containing combination can be used safely without any side effect on the skin. Meanwhile, by means of the composition, the skin elasticity is improved through deactivating the elastase, so that the skin anti-aging effect and the skin wound healing effect are greatly enhanced.

Description

As the new purposes of plant sterol of elastase activity inhibitor and the compositions that contains it
Technical field
The present invention relates to a kind ofly bring into play the plant sterol of elastase activity inhibitor function and take its compositions that is effective ingredient, said composition is improved skin elastic force and is significantly strengthened skin anti-aging effect and skin wound curative effect by elastoser deactivation.
Background technology
In skin, elastin fiber forms cross-bond and skin elastic force is provided in corium (epiderm) inner side together with collagen fiber.Along with the age increases, skin presents elastin fiber shortage and coagulation, collagen fiber reduce, cell infiltration increases phenomenon on histology, occurs showing as the activity degree of the elastoser of elastin laminin catabolic enzyme the phenomenon increasing on biochemistry.Therefore, the effect of elastoser sharply weakens skin elastic force and occurs depression (sagging) phenomenon.Elastoser is unique enzyme that can decompose elastin laminin of finding so far, suppresses it and just can fundamentally reduce skin aging.
In order to postpone skin aging, wetting agent, anti-inflammatory agent, elastin laminin and for the nutrient of the destroyed tissue of collagen cross-linking key and additive etc., add in cosmetic preparation, but fundamentally retarding ageing is limited.Therefore need a kind of inhibitor, its can be fundamentally maintaining the elastin laminin of skin elastic force and the decomposition of collagen is suppressed.
Although use the similar materials such as synthetic peptide (peptide) derivant of its structure and animality extract or collagen and elastin laminin for this object, but it has safety and stability problem and does not also reach the desired Expected Results in this area, therefore in the urgent need to develop a kind of than prior art to human-body safety and respond well new functionalized material, Japan's patent discloses 2004-018793 communique and discloses fine, soft fur helleborine, Red Hill and without aspidistra, Cephalanthera falcata (Thunb) Lindl flower, plumage phalaenopsis etc., have the composition of elastoser deactivation effect.
But such fact is not at present also by cognitive widely, that is plant sterol can be improved skin elastic force and significantly be strengthened skin anti-aging effect and skin wound curative effect by elastoser deactivation.
Summary of the invention
The technical problem to be addressed by invention
People of the present invention be take plant containing natural thing and have been explored and can improve that elastin laminin reduces and destroy the skin elastic force being caused and weaken phenomenon and solve cutaneous safety and the aging resistance material of stability problem when cosmetic preparation coordinates as object, found that plant sterol demonstrates good elastoser inhibition, while being coated on people's skin, also can improving significantly skin elastic force and significantly promote anti-aging effect and skin wound curative effect, thereby having completed the present invention.
Therefore, the object of this invention is to provide a kind of preparation composition for external use that contains plant sterol, this plant sterol does not cause skin side-effects and effectively suppresses the activity of elastoser and bring into play skin elastic force and improve effect and skin wound curative effect.
Solve the technical scheme of problem
In order to solve above-mentioned problem, the invention provides the new purposes of a kind of plant sterol as elastase activity inhibitor.
Preferably, above-mentioned plant sterol is cupreol (Beta sitosterol) or stigmasterol (stigmasterol).
In order to solve another problem, the invention provides the Dermatologic preparation composition that a kind of plant sterol of take inhibition elastase activity is effective ingredient.
Preferably, the above-mentioned plant sterol of Dermatologic preparation composition of the present invention is cupreol or stigmasterol.
Preferably, the content of the above-mentioned plant sterol of Dermatologic preparation composition of the present invention is 0.001 to 10 % by weight than entire combination thing gross weight.
Dermatologic preparation composition of the present invention can be that skin elastic force improves with cosmetic combination (Cosmeticcomposition) or skin wound healing pharmaceutical compositions.
Beneficial effect
As previously mentioned, plant sterol of the present invention improves skin elastic force by elastoser deactivation property improvement and is significantly strengthened skin anti-aging effect and skin wound curative effect.
The specific embodiment
The invention provides a kind of new purposes of the plant sterol as elastase inhibitor and take that it suppresses the preparation composition for external use of elastase activity effectively as effective ingredient.
In general, plant sterol is because the ability of stable emulsion state is compared with strong and use as emulsifying agent when manufacturing cosmetics or ink, while comprising the mankind's animal picked-up stigmasterol and cupreol, can reduce total cholesterol level and the LDL-C level in blood, so it plays a significant role as pharmaceuticals raw material.And plant sterol is also considered to reduce the danger of the coronary heart disease (coronary heart disease) of angina pectoris, myocardial infarction disease and so on.
Although plant sterol of the present invention can be from fruit, vegetable, nuts, frumentum, beans and vegetative grease, in the plant resources that such as rapeseed oil, Semen Maydis oil, sunflower oil, naked barley, wheat, Fructus Hordei Vulgaris, Herba bromi japonici etc. contained high concentration plant sterol, extract, but be not limited to above-mentioned plant resources.This plant sterol can obtain by the whole bag of tricks, and while considering economic benefit, preferably, the deodorization distillate that obtains when making soybean oil is separated and obtain.
Above-mentioned plant sterol utilizes nonpolar extraction extract, filter and make with the plant resources that solvent contains high concentration plant sterol to rapeseed oil, Semen Maydis oil, sunflower oil, naked barley, wheat, Fructus Hordei Vulgaris, Herba bromi japonici etc., extraction can be used hexane (hexane), ether (ether), benzene (benzene), chloroform (chloroform), cyclohexane extraction (cyclohexane), toluene (toluene) with solvent, can utilize the method extraction of supercritical extraction and so on.Can be by carrying out separately or the parallel column chromatography separated (column chromatography) that is filled with the various synthetic resin such as C18 or silica gel (silica gel) and HPLC (high performance liquid chromatography) analytic process (HPLC) etc. and from above-mentioned plant extract separation and refine plant sterol.Yet the extraction of effective ingredient and separated method of refining need not be defined in said method.
With 0.001～10 % by weight with respect to composition total weight, contain above-mentioned plant sterol.The present invention contains above-mentioned plant sterol in order to obtain desired effect with 0.001～10 % by weight with respect to composition total weight.During lower than 0.001 % by weight, be difficult to obtain suitable usefulness, while surpassing 10 % by weight, can have influence on safety and the stability of product.
As being directly coated in the compositions playing a role on skin, preparation composition for external use of the present invention can not limit especially to the dosage form of pharmaceutical compositions and even cosmetic combination, for example, can make soft and moist astringent, astringent compacts, nutrition astringent, nourishing cream, massage cream, the dew (essence) of refining, eye cream, eye contour balm (eye essence), cleansing cream, clean cream, cleansing cream, makeup removing water, face mask cream, face powder, skin care milk (body lotion), health breast (cream), body care oil, the health breast (body essence) of refining, clean body agent, hair dye, hair lotion (hair tonic), hair nursing liquid (scalp treatment), cream (lotion), ointment, cosmetic glue (gel), emulsion (cream), mould material (patch) or spray etc.
Below in conjunction with embodiment and test example, illustrate formation of the present invention and action effect, but the invention is not restricted to these examples.
[embodiment 1] manufactures plant sterol with soybean oil deodorizer distillate
Soybean oil deodorizer distillate (content of phytosterol: 27%) 200g and toluene 200g stir and are warmed up to 90 ℃ with 300rpm after pouring the there-necked flask of 3L into, then add 25% (w/w) NaOH solution 200g.Afterwards, at 80 ℃, with 300rpm, stir above-mentioned reaction product and add lentamente 50% (w/w) sulfuric acid solution 150g, then stirring after 15 minutes standingly, removing water layer and obtain oil reservoir.Repeatedly clean oil reservoir until sulphuric acid is completely removed, after toluene is removed in the compression of reducing pressure, filtered at 110 ℃.In above-mentioned filtrate, mix the there-necked flask of pouring 3L after methanol 300g into, then at 65 ℃, react cool to room temperature after 30 minutes, stir again 24 hours, after the fixedly product generating in whipping process is filtered, utilize methanol 200g to clean, after in addition methanol is removed in distilling under reduced pressure completely solid product, make plant sterol.The yield of made plant sterol and purity are respectively 75% and 98%.
Separated and the confirmation of [embodiment 2] plant sterol
For above-mentioned plant sterol 1.5g, carried out the separation of C18 column chromatography.Now, the solvent that the post dissolution fluid using mixes according to the volume ratio of 80: 20 (v/v) with water separately with methanol rose at first and increased methanol ratio gradually so that methanol becomes 100% in 40 minute, and the dissolution rate of solvent and detection wavelength are respectively for 60ml/ divides the 210nm with UV.Carry out from inferior component 48～52 and 55～60, having obtained cupreol 0.75g and stigmasterol 0.38g after the separation of above-mentioned C18 column chromatography.
The Instrumental Analysis result of separated plant sterol is as follows.
Compound 1 (cupreol)
1H-NMR(CDCl 3，600MHz)δ3.53(tdd，1H，J＝4.5，4.2，3.8Hz，H-3)，δ5.36(t，1H，J＝6.4Hz，H-5)，δ0.93(d，3H，J＝6.5Hz，H-19)，δ0.84(t，3H，J＝7.2Hz，H-24)，δ0.83(d，3H，J＝6.4Hz，H-26)，δ0.81(d，3H，J＝6.4Hz，H-27)，δ0.68(s，3H，H-28)，δ1.01(s，3H，H-29)
13C-NMR(CDCl 3，150MHz)δ37.5(C-1)，δ31.9(C-2)，δ72.0(C-3)，δ42.5(C-4)，δ140.9(C-5)，δ121.9(C-6)，δ32.1(C-7)，δ32.1(C-8)，δ50.3(C-9)，δ36.7(C-10)，δ21.3(C-11)，δ39.9(C-12)，δ42.6(C-13)，δ56.9(C-14)，δ26.3(C-15)，δ28.5(C-16)，δ56.3(C-17)，δ36.3(C-18)，δ19.2(C-19)，δ34.2(C-20)，δ26.3(C-21)，δ46.1(C-22)，δ23.3(C-23)，δ12.2(C-24)，δ29.4(C-25)，δ20.1(C-26)，δ19.6(C-27)，δ19.0(C-28)，δ12.0(C-29)
EIMS(C 29H 48O?m/z(rel.int.))：412[M +](39.7％)，351(13.5％)，314(7.0％)，300(25.5％)，271(38.4％)，229(8.6％)，213(10.6％)，55(100％)
Compound 2 (stigmasterol)
1H-NMR(CDCl 3，600MHz)δ3.51(tdd，1H，J＝4.5，4.3，3.8Hz，H-3)，δ5.31(t，1H，J＝6.1Hz，H-5)，δ0.91(d，3H，J＝6.2Hz，H-19)，δ4.98(m，1H，H-20)，δ5.14(m，1H，H-21)，δ0.83(t，3H，J＝7.1Hz，H-24)，δ0.82(d，3H，J＝6.6Hz，H-26)，δ0.80(d，3H，J＝6.6Hz，H-27)，δ0.71(s，3H，H-28)，δ1.03(s，3H，H-29)
13C-NMR(CDCl 3，150MHz)δ37.6(C-1)，δ32.1(C-2)，δ72.1(C-3)，δ42.4(C-4)，δ141.1(C-5)，δ121.8(C-6)，δ31.8(C-7)，δ31.8(C-8)，δ50.2(C-9)，δ36.6(C-10)，δ21.5(C-11)，δ39.9(C-12)，δ42.4(C-13)，δ56.8(C-14)，δ24.4(C-15)，δ29.3(C-16)，δ56.2(C-17)，δ40.6(C-18)，δ21.7(C-19)，δ138.7(C-20)，δ129.6(C-21)，δ46.1(C-22)，δ25.4(C-23)，δ12.1(C-24)，δ29.6(C-25)，δ20.2(C-26)，δ19.8(C-27)，δ18.9(C-28)，δ12.2(C-29)
EIMS(C 29H 50O?m/z(rel.int.))：414[M +](100％)，396(30.8％)，381(14.0％)，329(13.7％)，303(22.1％)，255(11.8％)，213(12.2％)，145(18.5％)，95(21.6％)，81(21.3％)，55(25.8％)，43(45.0％).
The elastoser inhibition of [test example 1] plant sterol
Elastoser extraction, from Pancreas Sus domestica, has been used Sigma company product.The test method(s) of the hydrolysis of synthetic peptide (peptide) substrate (Sigma) of utilization based on by means of pancreas elastoser is tested, the catalyst activity value using the increase of 4-nitroaniline (4-nitroanilide) discharge capacity of the time per unit at optical wavelength 410nm place as elastoser.Ba Ge testing liquid adjusts after the finite concentration of 1mg/ml and extracts separately 40 μ l, in this interpolation, be dissolved in after proporcine pancreas elastase (2.5U/ml) the solution 40 μ l of 50mM Tris-HCl buffer (pH8.6), N-succinyl-(L-Ala) 3-p-nitroanilide (0.5mg/ml) that is dissolved in 50mM Tris-HCl buffer (pH8.6) as substrate is added to 80 μ l, then at 37 ℃, carried out reaction in 30 minutes.For the growing amount of the 4-nitroaniline generating from substrate, at 410nm, measured trap, utilize following mathematical expression 1 to calculate elastoser and suppress degree.
[mathematical expression 1]
Elastin laminin enzyme inhibition rate (%)=1-(trap of the non-interpolation group of trap/test portion of test portion interpolation group) x100
[table 1]
Figure BSA00000789473900061
By above-mentioned table 1, learnt, plant sterol compound possesses and has concentration dependent form elastase activity inhibition.
Skin moisture-keeping and the elasticity effect of [test example: 2] plant sterol
The emulsion that use contains plant sterol of the present invention (cream) cosmetic preparation and the emulsion cosmetic preparation that does not contain plant sterol have carried out clinical trial for skin moisture-keeping and elasticity effect.Clinical trial emulsion used is according to content production shown in lower list 2.
[table 2]
Figure BSA00000789473900071
For the impact of test plant sterol on skin elastic force, be subject to inspection to have 20 people's left eye edge to be suitable for twice every day.The right eye edge of not processing as a control group.Utilizing moisture of skin measuring instrument CM 80 and skin elastic force measuring instrument SEM 474 to measure cosmetic preparation to contain plant sterol processes before and processes and the skin elastic force of the skin surface after 14 days.The skin moisture-keeping carrying out at moisture of skin measuring instrument CM 820 is compared increased moisturizing power value and is represented with %, and person under inspection 20 people's meansigma methods is presented in result in measuring with matched group.Utilize skin elastic force measuring instrument SEM 474 to measure when skin elastic force is spent and measure wrinkle depth, the less expression elastic force of its value is better.Compare reduced elastic force degree value with matched group and represent with %, and person under inspection 20 people's meansigma methods is presented in result.
[table 3]
Dosage form example Skin moisture-keeping effect (%) Skin elastic force degree effect (%)
Dosage form 1 34 42
Dosage form 2 39 48
Dosage form 3 33 40
Compare dosage form 12 18
By above-mentioned table 3, learnt the comparison dosage form that the moisturizing of 1 to the 3 pair of skin of dosage form that contains plant sterol and elastic force degree successful are better than not using plant sterol.
[test example 3: the Wound healing effect of plant sterol]
After allowing ointment base (base) with the plant sterol, cupreol and the stigmasterol that comprise soybean oil deodorizer distillate with respect to 5 % by weight of overall weight separately, make ointment 1, ointment 2 and ointment 3, matched group has only been used ointment base.
In order to measure Wound healing effect, utilize mice to carry out zoopery.
Utilize polyvidone (Povidone) and alcohol disinfection solution to process after the skin of mice belly; use No. 15 scalpels on skin, to generate wound; then then ointment 1, ointment 2, ointment 3 and matched group are coated to wound, recycling gauze covers coating part and is protected.Within one day, carry out twice this coating.
For 4 mices that applied separately ointment, while again applying, all carry out perusal at every turn.
During perusal, the wound of matched group expands, healing postpones and infects, but the wound of ointment of the present invention 1,2 and 3 does not expand and obtains and cure gradually.

Claims (7)

1. as the new purposes of plant sterol of elastase activity inhibitor.
2. the new purposes of the plant sterol as elastase activity inhibitor according to claim 1, is characterized in that, above-mentioned plant sterol is cupreol or stigmasterol.
3. take and suppress the Dermatologic preparation composition that the plant sterol of elastase activity is effective ingredient.
4. Dermatologic preparation composition according to claim 3, is characterized in that, above-mentioned plant sterol is cupreol or stigmasterol.
5. according to the Dermatologic preparation composition described in claim 3 or 4, it is characterized in that, the content of above-mentioned plant sterol is 0.001 to 10 % by weight than entire combination thing gross weight.
6. according to the Dermatologic preparation composition described in claim 3 or 4, it is characterized in that, above-mentioned preparation composition for external use is skin elastic force improvement cosmetic combination.
7. according to the Dermatologic preparation composition described in claim 3 or 4, it is characterized in that, above-mentioned preparation composition for external use is skin wound healing pharmaceutical compositions.
CN201210391238.2A 2012-09-13 2012-10-16 New application of phytosterol functioning as elastinase activity inhibitor, and composition containing the same Pending CN103655221A (en)

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CN110179730B (en) * 2019-06-19 2020-07-14 广东默默化妆品有限公司 Repair cream
CN111759955A (en) * 2020-07-17 2020-10-13 贵州松桃信仁苗药有限公司 Breast enlarging composition

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Application publication date: 20140326