CN108904343A - A kind of compositions extracted from gingko biloba leaves of anti-aging and the preparation method and application thereof - Google Patents
A kind of compositions extracted from gingko biloba leaves of anti-aging and the preparation method and application thereof Download PDFInfo
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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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/82—Preparation or application process involves sonication or ultrasonication
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Abstract
The present invention relates to a kind of cosmetic industry additives, a kind of compositions extracted from gingko biloba leaves with delaying senility function is specifically provided, contain 50-95 parts of ginkgo biloba leaf total terpene lactones in the composition in parts by weight, 22-60 parts of ginkgo leaf total flavonoids, and ginkgo leaf ginkgoic acid is less than 0.0035 part, wherein ginkgo biloba leaf total terpene lactone is selected from ginkalide A, ginkolide B, ginkalide C, one of bilobalide J and Bilobalide are a variety of, ginkgo leaf total flavonoid is selected from rutin, Quercitrin-3-O-glucoside, Kaempferol -3-O- glucoside, one of Isorhamnetin -3-O- glucoside and myricetin are a variety of.The composition can be mixed to get by monomer, it can also be by purifying to obtain to ginkgo leaf extracting and developing, different resins purify the effective component that can be effectively enriched in ginkgo leaf step by step, significantly improve effect of the composition in terms of delaying cell aging, can be widely applied in various cosmetics.
Description
Technical field
The invention belongs to cosmetic additive agent, it is related to a kind of compositions extracted from gingko biloba leaves and its extracting method and application, specifically relates to
And a kind of compositions extracted from gingko biloba leaves and its extracting method and the application of anti-aging.
Background technique
Ginkgo leaf occurred as soon as on earth before 3.45 hundred million years, was the distinctive quaternary glacier epoch few survivors tree of China
Kind.The resource distribution of ginkgo leaf 70% is in China, and more than 50, whole world country is all using ginkgo biloba p.e as treatment heart and brain blood
The plant material source of pipe disease.
The chemical component of ginkgo leaf is considerably complicated.Main active in ginkgo leaf is divided into flavones ingredient, in ginkgo
Lactone component and ginkgoic acid three categories.More than 34 flavone compounds are isolated from ginkgo leaf at present, more than 70 kinds flavones
Class compound passes through mass spectrum Preliminary Identification.Main Flavonoids aglycon in ginkgo leaf is Quercetin, Kaempferol, the derivative of Isorhamnetin
Object and some glucose connected with different connection form with quantity and rhamnose and some passed through by two molecule flavones parent nucleus
A kind of bis-flavonoid that C-C key is polymerized.Also some characteristic lactone constituents include diterpene in ginkgo leaf
Class lactone compound and sesquiterpenoids lactone compound.In addition to this, ginkgoic acid is main toxic substance in ginkgo biloba p.e
Matter has sensitization, embryotoxicity, cytotoxicity, causes prominent property and immunotoxicity.Currently, EGB production standard is wanted in Chinese Pharmacopoeia
It asks and the content of ginkgoic acid is controlled in 10ppm hereinafter, EGB produces standard requirements the content of ginkgoic acid in Europe and United States Pharmacopeia
Control is in 5ppm or less.
Plant of the ginkgo leaf as integration of drinking and medicinal herbs has multiple biological activities, just has in the 1960s to ginkgo leaf
Pharmacological action and practical application research, first ginkgo biloba p.e that Dr Willmar Schwabe develops
EGB761 has significant curative effect to cardiovascular and cerebrovascular disease.The active constituent of ginkgo biloba p.e has treatment the nervous system disease,
Reducing blood lipid, improves immunity of organisms, and anti-oxidant and free-radical scavenging activity and other effects has preferable medical value and health care function
Effect.In addition to this, EGB also has the function of inhibiting Staphylococcus aureus, streptococcus and fungi.Modern pharmacology research shows silver
Apricot leaf extract has anti-platelet activating factor, anti-cerebral ischemia anoxic, reducing blood lipid, removing free radical, relaxation bronchus smooth
The effects of flesh, anti-inflammatory and enhancing nervous system activity, to coronary heart disease, hypertension, angina pectoris, artery sclerosis, Aging, old
The diseases related with cardiovascular circulation such as year property dementia, hypomnesia, aging have significant prevention and treatment effect.Currently,
Ginkgo biloba p.e is widely used in the drug for the treatment of cardiovascular and cerebrovascular disease, as patent application CN103463145A is disclosed
It is a kind of to refine extract by the ginkgo leaf of raw material of ginkgo fallen leaves, there is good anti-oxidant, platelet aggregation-against and its mind
Through first cytoprotection, and adverse reaction is low, can be used as the drug of prevention and treatment cardiovascular and cerebrovascular disease and the main original of health food
Material；Patent application CN106420850A discloses compositions extracted from gingko biloba leaves, total flavonoids 25-43% in the composition, in ginkgo
Ester 6.5-17%, Bilobalide 3-5%, ginkgoic acid are less than 3ppm, and the disease in terms for the treatment of angiocarpy has good efficacy.
Recent study shows that ginkgo leaf has preferable protective effect to skin, is embodied in and inhibits UVB radiation and light
Aging promotes blood microcirculation, anti-oxidant and inhibition cellular damage and anti-inflammatory and neuroprotection etc., has in terms of cosmetics
Biggish application space.Patent application CN107913204A discloses a kind of ginkgo leaf facial treatment milk, raw material in formula and
Weight ratio is respectively：10 parts of ginkgo biloba p.e, 3 parts of stearic acid monoglycerides, 3 parts of White Mineral Oil, 3 parts of caprylic/capric glyceryl ester,
1 part of hydrogenated vegetable oil, 2.5 parts of stearic acid, 10 parts of polyacrylic resin, 2.5 parts of D-sorbite, 3 parts of propylene glycol, triethanolamine
0.7 part, 0.2 part of methyl p-hydroxybenzoate, appropriate essence, Preservative qs, deionized water add to 100 parts.It is prepared
Ginkgo leaf skin care milk there is wrinkle resistant whitening, remove free radical and other effects.Patent application CN103387896A discloses a kind of silver
Apricot leaf whitening compound perfumed soap, glycosides displayed, Amino acid synthesis collagen composition in ginkgo leaf inhibit melanin to human body beauty treatment
Growth keeps skin gloss and elasticity to play no small effect.The above patent is not concerned about ginkgo leaf in anti-cell aging side
The effect of face, meanwhile, specific ingredient for ginkgo biloba p.e and cell ageing how to be inhibited not study, product
Safety can not be guaranteed.
Currently, a large number of studies show that ginkegetin can be by inhibiting UVB radiation to play light aging protective effect, ginkgo
The primary efficacy of lactone constituents is to promote blood microcirculation, anti-oxidant, inhibition cellular damage, anti-inflammatory and neuroprotection etc..Such as
Jiang Xiuxin[58]It is living by the study found that ginkolide B can be obviously improved aged body platelet function, being not only blood platelet
Change the factor (PAF) antagonist, also having the function of, which reduces ROS, generates.But the physiological action of ginkgo biloba p.e and its complexity
Chemical component have close relationship, ginkalide A is concentrated mainly on for the research of its active constituent both at home and abroad, B, J and
Bilobalide and ginkegetin and Isoginkgetin, main efficacy study concentrates on inhibiting cellular damage, anti-inflammatory anti-
Oxidation, neuroprotection and several aspects that promote blood circulation, but simultaneously for the structure-activity relationship between functional component and activity
Without further investigation.In addition, according to the basis of its efficacy study, ginkgo leaf comes as the plant for the treatment of cardiovascular and cerebrovascular both at home and abroad
Source has good prospect in terms of anti-aging, but has no further investigation for its mechanism of action to delay senescence at present.
Summary of the invention
Based on the defect of the above-mentioned prior art, the present invention provides a kind of compositions extracted from gingko biloba leaves with delaying senility function,
By various active constituents in screening ginkgo leaf, the composition of composition is specified, so that the composition being prepared is with good
The effect of anti-aging, is able to suppress MMP-1 protein expression, promotes the expression of fibroblast Collagen I.
The present invention provides a kind of compositions extracted from gingko biloba leaves with delaying senility function, wherein containing 50-95 parts of ginkgo biloba leaf totals
Lactone, 22-60 part ginkgo leaf total flavonoid, and ginkgo leaf ginkgo acid content is less than 0.0035 part.
Further, the compositions extracted from gingko biloba leaves contains 70-90 parts of ginkgo biloba leaf total terpene lactones, 28-45 parts of ginkgo leaf total flavonoids,
And ginkgo leaf ginkgo acid content is less than 0.0030 part.
Further, it is yellow to contain 72-78 parts of ginkgo biloba leaf total terpene lactones, 34-44 parts of ginkgo biloba leaf totals for the compositions extracted from gingko biloba leaves
Ketone, and ginkgo leaf ginkgo acid content is less than 0.0028 part.
Further, the ginkgo biloba leaf total terpene lactone is selected from ginkalide A, ginkolide B, ginkalide C, bilobalide J
With one of Bilobalide or a variety of.
Further, the ginkgo biloba leaf total terpene lactone in parts by weight, is selected from 9-15 parts of ginkalide As, 5-10 parts
One of ginkolide B, 7-12 part ginkalide C, 1-8 parts of bilobalide Js and 48-55 parts of Bilobalides are a variety of.
Further, the ginkgo leaf total flavonoid is selected from rutin, Quercitrin-3-O-glucoside, Kaempferol -3-O- grape
One of glucosides, Isorhamnetin -3-O- glucoside and myricetin are a variety of.
Further, the ginkgo leaf total flavonoid is selected from 12-18 portions of rutins, 3-8 parts of Quercetins-in parts by weight
3-O- glucoside, 1-5 portions of Kaempferol -3-O- glucosides, 1-5 portions of Isorhamnetin -3-O- glucosides and 15-24 portions of red bayberries
One of element is a variety of.
Further, the compositions extracted from gingko biloba leaves in parts by weight, including 2-4 portions of Kaempferol -3-O- glucosides,
2-4 portions of Isorhamnetin -3-O- glucosides, 18-20 parts of myricetins, 10-12 parts of ginkalide As and 48-52 parts of Bilobalides.
Further, the compositions extracted from gingko biloba leaves further includes 15-18 portions of rutins, 4-6 parts of quercitrins in parts by weight
Element -3-O- glucoside, 6-9 parts of ginkolide Bs, 8-11 parts of ginkalide Cs and 2-7 parts of bilobalide Js.
Composition of the invention can be directly mixed with by each monomer, can also be obtained by extracting from ginkgo leaf.
Invention further provides the preparation methods of above-mentioned compositions extracted from gingko biloba leaves, include the following steps：
(1) ginkgo leaf crushed after being dried is added EtOH Sonicate and extracts, and supernatant is concentrated under reduced pressure, and obtains ginkgo biloba crude extract；
(2) ginkgo biloba crude extract is diluted with water, is centrifuged, and supernatant is adsorbed through macroporous absorbent resin, and ethyl alcohol is elution
Liquid, obtained ginkgo leaf eluent；
(3) ginkgo leaf eluent is successively adsorbed with Cation adsorption resin and macroporous absorbent resin, and ethyl alcohol is elution
Liquid is concentrated under reduced pressure to obtain the final product.
Further, the preparation method of the compositions extracted from gingko biloba leaves, includes the following steps：
(1) ginkgo leaf crushed after being dried crosses 80-120 mesh, and 12-18 times of 90%-100% EtOH Sonicate is added and extracts
0.5-1.5h is extracted 2-4 times, is merged supernatant and is concentrated under reduced pressure at 40-55 DEG C, obtains ginkgo biloba crude extract；
(2) ginkgo biloba crude extract adds 8-12 times of water dilution, centrifugation, and supernatant is adsorbed through DM130 macroporous absorbent resin,
55-65% ethyl alcohol is eluent, obtained ginkgo leaf eluent；
(3) ginkgo leaf eluent is successively adsorbed with 732 Cation adsorption resins and HPD5000 macroporous absorbent resin,
55-65% ethyl alcohol is eluent, is concentrated under reduced pressure to obtain the final product.
The present invention further provides above-mentioned compositions extracted from gingko biloba leaves answering in preparation anti-aging cosmetic industry additive
With.
Beneficial effects of the present invention are：
(1) compositions extracted from gingko biloba leaves provided by the invention has good activity of fighting against senium, and the composition can be by each group
Point monomer is mixed with to obtain, and is also possible to extract ginkgo leaf, Kaempferol -3-o- glucoside in composition, different
Rhamnetin -3-o- glucoside, myricetin, ginkalide A and Bilobalide can significantly inhibit fibroblast MMP-1 egg
White expression, the exclusive use of every kind of component can play good senile-resistant efficacy, and wherein ginkalide A and Bilobalide be also
The expression of fibroblast Collagen I protein can further be promoted, anti-aging function is more obvious, if by this 5 kinds
Component comprehensive function can cooperate with and play a role, more significantly inhibit skin aging.Ginkolide B, ginkalide C, ginkgo
Although lactone J, rutin, Quercitrin-3-O-glucoside are in terms of the expression for inhibiting fibroblast MMP-1 albumen without significant
Effect, but it will not influence Kaempferol -3-o- glucoside, Isorhamnetin -3-o- glucoside, myricetin, ginkalide A
Anti-aging function is played with Bilobalide, meanwhile, ginkolide B, ginkalide C, bilobalide J, rutin, Quercetin -3-
The presence of O- glucoside, the function that can further promote composition to play anti-aging by improving DPPH Scavenging activity etc.
Effect.
(2) composition of the invention can also be obtained by the extraction to Active Components of Ginkgo Leaves, using ethyl alcohol as eluant, eluent,
Pass through 732 Cation adsorption resins and HPD5000 macroporous absorbent resin respectively, the active constituent in ginkgo biloba p.e is carried out
Enrichment contains 50-95 parts of ginkgo biloba leaf total terpene lactones, 22-60 parts of ginkgo leaf total flavonoids in finally obtained ginkgo biloba p.e, and
Ginkgo leaf ginkgo acid content is less than 0.0035 part.The technique extract the ginkgo biloba p.e active component content arrived and purity compared with
Height, and preparation process is simple, in the expression for inhibiting fibroblast MMP-1 albumen and the expression side for promoting Collagen I protein
Face obvious effect, can be widely applied in cosmetics, improve anti-aging function.
(3) present invention have studied ginkgo biloba p.e active constituent be ginkalide A, ginkolide B, ginkalide C,
Bilobalide J, five kinds of characteristic lactone constituents of Bilobalide and rutin, Quercitrin-3-O-glucoside, Kaempferol -3-O-
Ten kinds of glucoside, Isorhamnetin -3-O- glucoside, myricetin monomer components, to fibrocyte MMP-1 albumen and
The influence of the expression of Collagen I protein, the clear and thorough active constituent composition for having studied ginkgo biloba p.e anti-aging
And mechanism, compensate for the blank to ginkgo leaf anti-aging active constituent structure activity study.
Detailed description of the invention
Fig. 1 is measurement of 10 kinds of monomer components to fibroblast MMP-1 inhibitory activity
Fig. 2 is the influence that 10 kinds of monomer components express fibroblast Collagen I
Wherein,
1-rutin 2-Quercetin-3-o- glucoside 3-Kaempferol-3-o- glucoside
4-Isorhamnetin-3-o- glucoside 5-myricetin, 6-ginkalide As
7-ginkolide B 8-ginkalide C, 9-bilobalide Js
10-Bilobalides
Specific embodiment
1 compositions extracted from gingko biloba leaves of embodiment and its extracting method
(1) ginkgo leaf crushed after being dried sieves with 100 mesh sieve, and 15 times of 95% EtOH Sonicate is added and extracts 1h, extracts 3 times, closes
And supernatant and be concentrated under reduced pressure at 50 DEG C, obtain ginkgo biloba crude extract；
(2) ginkgo biloba crude extract adds 10 times of water dilutions, centrifugations, and supernatant is adsorbed through DM130 macroporous absorbent resin,
60% ethyl alcohol is eluent, obtained ginkgo leaf eluent；
(3) ginkgo leaf eluent is successively adsorbed with 732 Cation adsorption resins and HPD5000 macroporous absorbent resin,
60% ethyl alcohol is eluent, is concentrated under reduced pressure to obtain the final product.
Active constituent and content detection：
Weigh the appropriate above medicinal extract to be redissolved, the concentration of 1mg/mL be made into methanol, by UPLC/MS/MS with
HPLC/DAD method extracts its lactone constituents, ginkgo sour component and flavones ingredient to activity and carries out quantitative analysis, specific as follows：
(1) content detection of Ginkgolide Component：
ESI- mode：Drying nitrogen flow velocity 10L/min, 35 DEG C of temperature, nebulizer pressure：30psi；Capillary voltage：
3500V；MRM mode is quantitative, and each reference substance capillary outlet voltage and collision energy are by optimization, to obtain more stable ion
With it is higher corresponding.
Chromatographic condition：ACQUITY UPLC BEH 1.7 μm of chromatographic columns of C18, mobile phase are that acetonitrile and 0.1% formic acid are molten
Liquid, gradient elution (0-0.5 minutes, 10%A, 0.5-4 minute, 90%A), flow velocity 0.3ml/min, 30 DEG C of column temperature, 2 μ of sample volume
l。
The drafting of standard curve：Accurate Ginkgolide A. B. C, J and the Bilobalide standard reference material of measuring is appropriate respectively, sets
In volumetric flask, be added methanol preparation containing single reference substance mass concentration be respectively 0.008,0.008,0.008,0.0015,
The mixed reference substance solution of 0.050mg/ml changes the concentration of mixed reference substance solution by changing sampling volume, will configure
Good mixing reference substance is analyzed by above-mentioned chromatographic condition, draws standard curve.
Sample measurement：It weighs the appropriate above medicinal extract to be redissolved, the concentration of 1mg/mL is made into methanol, by above-mentioned color
Spectral condition carries out analysis
(2) flavones ingredient content detection：
Chromatographic condition：Mobile phase is acetonitrile and 0.2% phosphoric acid solution, and flow velocity 0.5ml/min, column temperature is 30 DEG C, sample introduction
Amount is 5 μ l, Detection wavelength 270nm, gradient elution such as following table：
The drafting of standard curve：Precision weighs rutin, Quercitrin-3-O-glucoside, Kaempferol -3-O- glucose respectively
Glycosides, Isorhamnetin -3-O- glucoside, myricetin reference substance are appropriate, and methanol preparation is added to distinguish containing single reference substance mass concentration
For 0.012,0.006,0.012,0.012,0.012 mixed reference substance solution, and with the mixing of methanol dilution to various concentration
Reference substance solution is detected according to above-mentioned chromatographic condition, draws standard curve.
Sample measurement：It weighs the appropriate above medicinal extract to be redissolved, the concentration of 1mg/mL is made into methanol, through 0.22 μm
It is detected after filtering with microporous membrane according to above-mentioned liquid-phase condition.
(3) ginkgoic acid component content detects
Mass Spectrometry Conditions：ESI- mode：Capillary voltage：2500V removes solvent stream speed 800L/H, removes solvent temperature degree 450
DEG C, 150 DEG C of source temperature, nebulizer pressure：30psi；MRM mode, each reference substance capillary outlet voltage and collision energy are by excellent
Change, to obtain more stable ion and higher corresponding.
Chromatographic condition：ACQUITY UPLC BEH 1.7 μm of chromatographic columns of C18, mobile phase are that acetonitrile and 0.1% formic acid are molten
Liquid, gradient elution (0-1.0 minutes, 10%A, 1.0-6.0 minute, 90%A), flow velocity 0.4ml/min, 35 DEG C of column temperature, sample
10 DEG C of room temperature, sample volume is 10 μ l.
The drafting of standard curve：Precision weighs ginkgo and calculates C13 respectively:0,C15:0,C15:1,C17:1,C17:2 reference substances
In right amount, it is configured to the mixed solution of 2mg/ml with methanol, and is diluted step by step with methanol, is detected into liquid chromatogram, draws
Standard curve.
Sample measurement：It weighs the appropriate above medicinal extract to be redissolved, the concentration of 1mg/mL is made into methanol, through 0.22 μm
It is as follows to be measured result into liquid chromatograph for filtering with microporous membrane.
| Lactone | 7.94% | Flavonoids | 4.36% | Ginkgoic acid | 2.69ppm |
| Ginkalide A | 0.97% | Rutin | 1.61% | C13:0 | 0.09ppm |
| Ginkolide B | 0.66% | Quercitrin-3-O-glucoside | 0.43% | C15:0 | 0.06ppm |
| Ginkalide C | 0.85% | Kaempferol -3-O- glucoside | 0.20% | C15:1 | 0.23ppm |
| Bilobalide J | 0.25% | Isorhamnetin -3-O- glucoside | 0.31% | C17:1 | 2.32ppm |
| Bilobalide | 5.21% | Myricetin | 1.81% |
2 compositions extracted from gingko biloba leaves of embodiment and its extracting method
(1) ginkgo leaf crushed after being dried crosses 80 meshes, and 12 times of 90% EtOH Sonicate is added and extracts 1.5h, extracts 2 times,
Merge supernatant and be concentrated under reduced pressure at 40 DEG C, obtains ginkgo biloba crude extract；
(2) ginkgo biloba crude extract adds 8 times of water dilutions, centrifugations, and supernatant is adsorbed through DM130 macroporous absorbent resin,
55% ethyl alcohol is eluent, obtained ginkgo leaf eluent；
(3) ginkgo leaf eluent is successively adsorbed with 732 Cation adsorption resins and HPD5000 macroporous absorbent resin,
55% ethyl alcohol is eluent, is concentrated under reduced pressure to obtain the final product.
Active constituent and content detection：It is as a result as follows with embodiment 1.
| Lactone | 7.26% | Flavonoids | 3.4% | Ginkgoic acid | 3.21ppm |
| Ginkalide A | 0.92% | Rutin | 1.24% | C13:0 | 0.12ppm |
| Ginkolide B | 0.51% | Quercitrin-3-O-glucoside | 0.33% | C15:0 | 0.13ppm |
| Ginkalide C | 0.77% | Kaempferol -3-O- glucoside | 0.17% | C15:1 | 0.20ppm |
| Bilobalide J | 0.13% | Isorhamnetin -3-O- glucoside | 0.12% | C17:1 | 2.76ppm |
| Bilobalide | 4.93% | Myricetin | 1.54% |
3 compositions extracted from gingko biloba leaves of embodiment and its extracting method
(1) ginkgo leaf crushed after being dried crosses 120 meshes, and 18 times of 100% EtOH Sonicate is added and extracts 0.5h, extracts 4
It is secondary, merge supernatant and be concentrated under reduced pressure at 55 DEG C, obtains ginkgo biloba crude extract；
(2) ginkgo biloba crude extract adds 8 times of water dilutions, centrifugations, and supernatant is adsorbed through DM130 macroporous absorbent resin,
65% ethyl alcohol is eluent, obtained ginkgo leaf eluent；
(3) ginkgo leaf eluent is successively adsorbed with 732 Cation adsorption resins and HPD5000 macroporous absorbent resin,
65% ethyl alcohol is eluent, is concentrated under reduced pressure to obtain the final product.
Active constituent and content detection：With embodiment 1, as a result such as following table.
| Lactone | 9.33% | Flavonoids | 6.01% | Ginkgoic acid | 2.28ppm |
| Ginkalide A | 1.18% | Rutin | 1.85% | C13:0 | 0.09ppm |
| Ginkolide B | 0.87% | Quercitrin-3-O-glucoside | 0.82% | C15:0 | 0.12ppm |
| Ginkalide C | 1.11% | Kaempferol -3-O- glucoside | 0.47% | C15:1 | 0.09ppm |
| Bilobalide J | 0.69% | Isorhamnetin -3-O- glucoside | 0.41% | C17:1 | 1.98ppm |
| Bilobalide | 5.48% | Myricetin | 2.46% |
Embodiment 4-6 compositions extracted from gingko biloba leaves
By ginkalide A, ginkolide B, ginkalide C, bilobalide J, Bilobalide, rutin, the Portugal Quercetin -3-O-
10 kinds of polyglycoside, Kaempferol -3-O- glucoside, Isorhamnetin -3-O- glucoside, myricetin monomers are according to following weight parts
It is mixed, such as following table：
The compositions extracted from gingko biloba leaves that the different absorption resin treatment techniques of comparative example 1 obtain
In addition to step (2) are using AB-8 macroreticular resin, remaining is specific as follows with embodiment 1：
(1) ginkgo leaf crushed after being dried sieves with 100 mesh sieve, and 15 times of 95% EtOH Sonicate is added and extracts 1h, extracts 3 times, closes
And supernatant and be concentrated under reduced pressure at 50 DEG C, obtain ginkgo biloba crude extract；
(2) ginkgo biloba crude extract adds 10 times of water dilutions, centrifugations, and supernatant is adsorbed through AB-8 macroporous absorbent resin,
60% ethyl alcohol is eluent, obtained ginkgo leaf eluent；
(3) ginkgo leaf eluent is successively adsorbed with 732 Cation adsorption resins and HPD5000 macroporous absorbent resin,
60% ethyl alcohol is eluent, is concentrated under reduced pressure to obtain the final product.
Active constituent and content detection：It is as a result as follows with embodiment 1.
The compositions extracted from gingko biloba leaves that the different absorption resin treatment techniques of comparative example 2 obtain
In addition to step (3) are using D101 macroreticular resin, remaining is specific as follows with embodiment 1：
(1) ginkgo leaf crushed after being dried sieves with 100 mesh sieve, and 15 times of 95% EtOH Sonicate is added and extracts 1h, extracts 3 times, closes
And supernatant and be concentrated under reduced pressure at 50 DEG C, obtain ginkgo biloba crude extract；
(2) ginkgo biloba crude extract adds 10 times of water dilutions, centrifugations, and supernatant is adsorbed through DM130 macroporous absorbent resin,
60% ethyl alcohol is eluent, obtained ginkgo leaf eluent；
(3) ginkgo leaf eluent is successively adsorbed with 732 Cation adsorption resins and D101 macroporous absorbent resin, and 60%
Ethyl alcohol is eluent, is concentrated under reduced pressure to obtain the final product.
Active constituent and content detection：It is as a result as follows with embodiment 1.
| Lactone | 5.28% | Flavonoids | 9.61% | Ginkgoic acid | 4.20ppm |
| Ginkalide A | 0.65% | Rutin | 3.07% | C13:0 | 0.69ppm |
| Ginkolide B | 0.26% | Quercitrin-3-O-glucoside | 1.65% | C15:0 | 0.22ppm |
| Ginkalide C | 0.87% | Kaempferol -3-O- glucoside | 1.97% | C15:1 | 0.42ppm |
| Bilobalide J | 0.43% | Isorhamnetin -3-O- glucoside | 0.84% | C17:1 | 2.87ppm |
| Bilobalide | 3.07% | Myricetin | 2.08% |
The compositions extracted from gingko biloba leaves that the different extraction processes of comparative example 3 obtain
The ginkgo biloba crude extract that 1 step 1 of embodiment is prepared is obtained into ginkgo leaf not by organic solvent extraction and separation
With extraction component composite, remaining is specific as follows with embodiment 1：
(1) ginkgo leaf crushed after being dried sieves with 100 mesh sieve, and 15 times of 95% EtOH Sonicate is added and extracts 1h, extracts 3 times, closes
And supernatant and be concentrated under reduced pressure at 50 DEG C, obtain ginkgo biloba crude extract；
(2) above-mentioned gained ginkgo biloba crude extract is taken, is successively extracted, will be extracted with petroleum ether, ethyl acetate, n-butanol
The extract at three positions of gained is first concentrated with Rotary Evaporators, then concentrate is dried by vacuum oven,
Finally obtain ginkgo leaf medicinal extract i.e. petroleum ether, ethyl acetate and the n-butanol portion extract at three extraction positions.
Active constituent and content detection：It is as a result as follows with embodiment 1.
Petroleum ether part：
| Lactone | 3.26% | Flavonoids | 2.09% | Ginkgoic acid | 3.07ppm |
| Ginkalide A | 0.12% | Rutin | 0.25% | C13:0 | 0.09ppm |
| Ginkolide B | 0.26% | Quercitrin-3-O-glucoside | 0.82% | C15:0 | 0.12ppm |
| Ginkalide C | 0.64% | Kaempferol -3-O- glucoside | 0.38% | C15:1 | 0.88ppm |
| Bilobalide J | 0.98% | Isorhamnetin -3-O- glucoside | 0.18% | C17:1 | 1.98ppm |
| Bilobalide | 1.26% | Myricetin | 0.46% |
Ethyl acetate extract
| Lactone | 10.89% | Flavonoids | 7.36% | Ginkgoic acid | 4.24ppm |
| Ginkalide A | 0.83% | Rutin | 1.25% | C13:0 | 0.11ppm |
| Ginkolide B | 0.26% | Quercitrin-3-O-glucoside | 1.22% | C15:0 | 0.54ppm |
| Ginkalide C | 0.74% | Kaempferol -3-O- glucoside | 1.18% | C15:1 | 1.13ppm |
| Bilobalide J | 1.11% | Isorhamnetin -3-O- glucoside | 1.48% | C17:1 | 2.46ppm |
| Bilobalide | 7.95% | Myricetin | 2.23% |
N-butanol portion
| Lactone | 4.76% | Flavonoids | 3.25% | Ginkgoic acid | 1.98ppm |
| Ginkalide A | 1.12% | Rutin | 0.27% | C13:0 | 0.05ppm |
| Ginkolide B | 0.37% | Quercitrin-3-O-glucoside | 0.87% | C15:0 | 0.07ppm |
| Ginkalide C | 0.65% | Kaempferol -3-O- glucoside | 0.44% | C15:1 | 0.11ppm |
| Bilobalide J | 0.85% | Isorhamnetin -3-O- glucoside | 0.68% | C17:1 | 1.75ppm |
| Bilobalide | 1.77% | Myricetin | 0.99% |
The compositions extracted from gingko biloba leaves that the different elution processes of comparative example 4 obtain
In addition to step (2) and (3) eluent are using 95% ethyl alcohol, remaining is specific as follows with embodiment 1：
(1) ginkgo leaf crushed after being dried sieves with 100 mesh sieve, and 15 times of 95% EtOH Sonicate is added and extracts 1h, extracts 3 times, closes
And supernatant and be concentrated under reduced pressure at 50 DEG C, obtain ginkgo biloba crude extract；
(2) ginkgo biloba crude extract adds 10 times of water dilutions, centrifugations, and supernatant is adsorbed through DM130 macroporous absorbent resin,
95% ethyl alcohol is eluent, obtained ginkgo leaf eluent；
(3) ginkgo leaf eluent is successively adsorbed with 732 Cation adsorption resins and HPD5000 macroporous absorbent resin,
95% ethyl alcohol is eluent, is concentrated under reduced pressure to obtain the final product.
Comparative example 5-7 compositions extracted from gingko biloba leaves
Each monomer is mixed according to following weight parts, such as following table：
Wherein, compared with Example 1, comparative example 5 does not contain ginkolide B, but the ginkgolides containing 9.7 parts by weight
M；Comparative example 6 does not contain rutin, but the gingko alcohol containing 16.1 parts by weight；Comparative example 7 does not contain bilobalide J and quercitrin
Element -3-O- glucoside, but the apiolin -7- glucoside of ginkgolides M and 4.3 parts by weight containing 2.5 parts by weight.
1 compositions extracted from gingko biloba leaves of test example and active constituent anti-aging Activity determination
1.1 fibroblast viability examinations：
By ginkalide A, ginkolide B, ginkalide C, bilobalide J, Bilobalide, rutin, the Portugal Quercetin -3-O-
Ten kinds of polyglycoside, Kaempferol -3-O- glucoside, Isorhamnetin -3-O- glucoside, myricetin monomer components use 1% respectively
DMSO solution be configured to concentration be 0.4,0.2,0.1,0.05mg/mL solution, and be equipped with negative control group.
Fibroblast is with 1 × 105The density of/mL is laid on 96 orifice plates, and 0.1mL cell suspending liquid is added in every hole, to cell
Dosing is used for after adherent.Drug effect for 24 hours after, addition serum free medium is with 1:The 10 110 μ L of CCK-8 reagent that have diluted are anti-
1h is answered, measures its absorbance in microplate reader 450nm.Cell survival rate according to the following formula.
Cell survival rate=(each group absorbance/blank group absorbance) × 100%
As a result as follows：
1 monomer component of table to fibroblastic cell viability influence (n=3,)
As seen from the above table, Isorhamnetin -3-o- glucoside and myricetin are under 0.4mg/mL concentration, cell survival rate point
Not (63.86 ± 0.7) % and (58.58 ± 4.62) %, there are certain cytotoxicities, and under 0.2mg/mL concentration, cell is deposited
Motility rate has reached 80% or more；
In addition, rutin, Quercetin -3-o- glucoside, Kaempferol -3-o- glucoside and Ginkgolide A. B. C, J
With Bilobalide under 0.4mg/mL concentration, Cell viability has reached 80% or more, therefore combines actual conditions, selects
0.2mg/mL and 0.1mg/mL is the experimental concentration of following MMP-1 Indexs measure.
The detection of 1.2MMP-1 protein expression：
Fibroblast is with 2 × 104The density of/mL is laid on 6 orifice plates, and 1mL cell suspending liquid is added in every hole, adherent to cell
It is used for dosing afterwards.After drug effect for 24 hours after, take every group of cell supernatant, 1000 turns of centrifugation 15min take its supernatant to use after centrifugation
In test.It is tested according to MMP-1 detection kit operating process.First fit standard curve, calculates sample on this basis
The content of MMP-1, as a result as shown in Fig. 1.
The result shows that Kaempferol -3-o- glucoside, Isorhamnetin -3-o- glucoside, myricetin and ginkalide A
The expression of MMP-1 can be inhibited with Bilobalide, and relative to blank control group, influence of the Bilobalide to MMP-1 has
Significant difference (P < 0.05), in Kaempferol -3-o- glucoside, Isorhamnetin -3-o- glucoside, myricetin and ginkgo
Influence of the ester A to MMP-1 all has the difference (P < 0.01) of very significant.
The influence of 1.3 pairs of Collagen I proteins expression
Fibroblast is with 2 × 104The density of/mL is laid on 6 orifice plates, and 1mL cell suspending liquid is added in every hole, adherent to cell
It is used for dosing afterwards.After drug effect for 24 hours after, take every group of cell supernatant, 1000 turns of centrifugation 15min take its supernatant to use after centrifugation
In test.It is tested according to Collagen I detection kit operating process.First fit standard curve, calculates on this basis
The content of sample Collagen I, the results are shown in attached figure 2.
The result shows that Bilobalide has the expression of fibroblast Collagen I significant relative to control group
Facilitation (P < 0.05), ginkalide A have the facilitation of highly significant to the expression of fibroblast Collagen I
(P < 0.01).
1.4 compositions extracted from gingko biloba leaves antioxidant activity researchs
Ginkgo biloba p.e to fibroblast cell viability, to fibroblast MMP-1 inhibitory activity, to Collagen
The same 1.1-1.3 of measuring method of the influence of I protein expression.
Wherein, the ginkgo biloba p.e dehydrated alcohol that different embodiments and comparative example are prepared is dissolved and is configured to
1,0.5,0.25,0.125mg/mL；And it is equipped with solvent control group and negative control group, carry out the survey of fibroblast cell viability
It is fixed, concentration needed for subsequent experimental is determined further according to fibrocyte cell viability measurement result.
The different compositions extracted from gingko biloba leaves of table 2 to fibroblast cell viability influence (n=3,)
0.5mg/ml or less concentration, each compositions extracted from gingko biloba leaves are able to satisfy fibrocyte cell viability and reach 80% or more,
To reduce cost, and detection sensitivity is improved, 0.02 and 0.01mg/ml concentration is selected to carry out subsequent experimental.
3 compositions extracted from gingko biloba leaves of table to fibroblasts to secrete MMP-1 influence (n=3,)
Note：Compared with negative control group, * P < 0.05, * * P < 0.01.
From the data in table 3, it can be seen that effect of the compositions extracted from gingko biloba leaves provided by the invention in terms of inhibiting MMP-1 protein expression is aobvious
It writes and is higher than comparative example 1-7, illustrate that compositions extracted from gingko biloba leaves provided by the invention has stronger bioactivity, either composition is matched
Change than still composition aspect can significantly affect the effect of its anti-aging.
The influence that 4 compositions extracted from gingko biloba leaves of table expresses fibroblast Collagen I protein
Note：Compared with negative control group, * P < 0.05, * * P < 0.01.
From the data in table 4, it can be seen that compositions extracted from gingko biloba leaves provided by the invention is in terms of promoting the expression of Collagen I protein
Significant effect is higher than comparative example 1-7, further illustrates that compositions extracted from gingko biloba leaves provided by the invention has stronger bioactivity, nothing
The effect of its anti-aging can be significantly affected by the change for being composition proportion or composition aspect.
Above-mentioned detailed description is illustrating for one of them possible embodiments of the present invention, the embodiment not to
The scope of the patents of the invention is limited, all equivalence enforcements or change without departing from carried out by the present invention are intended to be limited solely by the technology of the present invention
In the range of scheme.
Claims (10)
1. a kind of compositions extracted from gingko biloba leaves with delaying senility function, which is characterized in that according to weight in the compositions extracted from gingko biloba leaves
Amount number meter contains 50-95 parts of ginkgo biloba leaf total terpene lactones, 22-60 parts of ginkgo leaf total flavonoids, and ginkgo leaf ginkgoic acid is less than 0.0035
Part；Preferably, the compositions extracted from gingko biloba leaves contains 70-90 parts of ginkgo biloba leaf total terpene lactones, 28-45 parts of ginkgo leaf total flavonoids, and ginkgo
Leaf ginkgo acid content is less than 0.0030 part；It is highly preferred that the compositions extracted from gingko biloba leaves contains 72-78 parts of ginkgo biloba leaf total terpene lactones, 34-
44 parts of ginkgo leaf total flavonoids, and ginkgo leaf ginkgo acid content is less than 0.0028 part.
2. the compositions extracted from gingko biloba leaves according to claim 1 with delaying senility function, which is characterized in that the ginkgo leaf
Total lactones are selected from one of ginkalide A, ginkolide B, ginkalide C, bilobalide J and Bilobalide or a variety of.
3. the compositions extracted from gingko biloba leaves according to claim 2 with delaying senility function, which is characterized in that the ginkgo leaf
Total lactones in parts by weight, are selected from 9-15 parts of ginkalide As, 5-10 parts of ginkolide Bs, 7-12 parts of ginkalide Cs, 1-8
Part one of bilobalide J and 48-55 parts of Bilobalides or a variety of.
4. the compositions extracted from gingko biloba leaves according to claim 1 with delaying senility function, which is characterized in that the ginkgo leaf
General flavone is selected from rutin, Quercitrin-3-O-glucoside, Kaempferol -3-O- glucoside, Isorhamnetin -3-O- glucoside
With one of myricetin or a variety of.
5. the compositions extracted from gingko biloba leaves according to claim 4 with delaying senility function, which is characterized in that the ginkgo leaf
General flavone in parts by weight, is selected from 12-18 portions of rutins, 3-8 parts of Quercitrin-3-O-glucosides, 1-5 parts of Kaempferol -3-
One of O- glucoside, 1-5 portions of Isorhamnetin -3-O- glucosides and 15-24 parts of myricetins are a variety of.
6. with the compositions extracted from gingko biloba leaves of delaying senility function according to claim 3 or 5, which is characterized in that the silver
Apricot leaf composition in parts by weight, including 2-4 portions of Kaempferol -3-O- glucosides, 2-4 portions of Isorhamnetin -3-O- grapes
Glucosides, 18-20 part myricetin, 10-12 parts of ginkalide As and 48-52 parts of Bilobalides.
7. the compositions extracted from gingko biloba leaves according to claim 6 with delaying senility function, which is characterized in that the ginkgo leaf
Composition further includes 15-18 portions of rutins, 4-6 parts of Quercitrin-3-O-glucosides, 6-9 parts of ginkgolides in parts by weight
B, 8-11 parts of ginkalide Cs and 2-7 parts of bilobalide Js.
8. the preparation method of compositions extracted from gingko biloba leaves, includes the following steps as described in claim any one of 1-7：By each component monomer
It proportionally mixes to obtain the final product.
9. the preparation method of compositions extracted from gingko biloba leaves, includes the following steps as described in claim any one of 1-7：
(1) ginkgo leaf crushed after being dried is added EtOH Sonicate and extracts, and supernatant is concentrated under reduced pressure, and obtains ginkgo biloba crude extract；
(2) ginkgo biloba crude extract is diluted with water, is centrifuged, and supernatant is adsorbed through macroporous absorbent resin, and ethyl alcohol is eluent, obtains
The ginkgo leaf eluent arrived；
(3) ginkgo leaf eluent is successively adsorbed with Cation adsorption resin and macroporous absorbent resin, and ethyl alcohol is eluent, is subtracted
Pressure is concentrated to obtain the final product.
10. any one of the claim 1-7 compositions extracted from gingko biloba leaves answering in preparation anti-aging cosmetic industry additive
With.
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| CN111686098A (en) * | 2020-07-13 | 2020-09-22 | 暨南大学 | Application of ginkgolic acid C15:1 in preparation of anti-aging drugs |
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