CN111825536A - Dendrobium candidum compound and cosmetics and application thereof - Google Patents
Dendrobium candidum compound and cosmetics and application thereof Download PDFInfo
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- CN111825536A CN111825536A CN202010709663.6A CN202010709663A CN111825536A CN 111825536 A CN111825536 A CN 111825536A CN 202010709663 A CN202010709663 A CN 202010709663A CN 111825536 A CN111825536 A CN 111825536A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- 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
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- 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
- 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
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
Abstract
The invention discloses a monomer compound in a Dendrobium candidum (called as Dendrobium huoshanense, with a scientific name of Dendrobium loddigesii Rolfe) extract, a preparation method thereof and application thereof in preparing cosmetics. The dendrobium candidum monomer compound has the effects of whitening and resisting aging.
Description
The application is a divisional application of Chinese patent application 'Dendrobium candidum extract and application thereof in preparing cosmetics' (application number is 201810023344.2, application date is 2018.01.10).
Technical Field
The invention belongs to the field of biological medicines and cosmetics. In particular to a dendrobium candidum extract with whitening effect and a monomer compound thereof. The dendrobium candidum extract and the monomer compound thereof have whitening and anti-aging effects, and can be used as an effect additive to be added into cosmetics.
Background
Dendrobii grandiflorum loddigesii Rolfe is a perennial herb of dendrobii of Orchidaceae (Orchidaceae), is also called as Dendrobium loddigesii, Dendrobium fimbriatum or Dendrobium otoxum, is loaded in various pharmacopoeias, is an important source of medicinal materials of dendrobii loddigesii, herba lysimachiae, and the like, is mainly distributed in provinces such as Guizhou, Guangxi, Yunnan, Guangdong, and the like, and is also distributed in Laos and Vietnamese. The dendrobium candidum mainly contains chemical components such as stilbenes, phenanthrenes, polyphenol, alkaloid, polysaccharide and the like, and has the activities of resisting platelet aggregation, inhibiting alpha-glucosidase, inhibiting Na +, K + -ATPase, inhibiting NO release and the like.
The dendrobium candidum is a common and rare Chinese medicinal material in China, and the stem of the dendrobium candidum with the effects of nourishing yin, clearing heat, tonifying stomach, promoting fluid production, moistening lung, relieving cough and the like can be used as a traditional Chinese medicine for treating stomach diseases, fever and dizziness. The extract of the stem of Dendrobium candidum has anti-diabetic activity on animals and humans, and can be used for treating type 2 diabetes.
"love heart and everyone's own", whether a person is beautiful, appear on face at first, whitening and anti-aging are the focus of attention in the field of skin care products. Arbutin, ascorbic acid, kojic acid, cell growth factors and the like are mostly added in the existing whitening and anti-aging skin care products, and the chemical components can cause pigment instability after long-term use and can cause certain damage to the skin. With the continuous development of natural products, people can transfer the sight to the natural products on the skin care cosmetics so as to obtain natural, green, safe and effective traditional Chinese medicine whitening and anti-aging cosmetics.
The whitening mechanism of the traditional Chinese medicine mainly comprises 3 ways of improving skin color by promoting blood circulation, reducing melanin content and protecting skin color by oxidation resistance. Tyrosinase is used as a main rate-limiting enzyme in the melanin formation process, the whitening effect of cosmetics is evaluated at present, and whether tyrosinase has an inhibiting effect or not is mainly considered. The measurement of the level of antioxidant activity by scavenging inhibition of reactive oxygen nitrogen radical groups is currently the most common type. Skin aging is mainly caused by both genetic factors (endogenous factors) and environmental factors (exogenous factors). Prolonged exposure to ultraviolet radiation, ionizing radiation, smoke and other chemical contaminants makes the external environment a major factor in the initiation of skin aging. Fibroblasts are the most prominent cells in the dermis layer and constitute the main body of the dermis together with self-secreted collagen, elastin, and other extracellular matrix components. Collagen secretion plays an important role in the process of skin aging. At present, anti-aging cosmetics are roughly classified into moisturizing type, antioxidant type and bioactive type cosmetics according to their effects. The anti-aging activity of the cosmetics is mainly examined by measuring the capacity of the cosmetics to remove free radicals and promote the secretion capacity of collagen and the in-vitro proliferation capacity of fibroblasts.
In the prior art, dendrobium candidum which has the functions of whitening and resisting aging is not involved, and the dendrobium candidum which is used as a functional additive to be added into cosmetics is not mentioned. The dendrobium candidum extract provided by the invention has the effects of whitening and resisting aging for the first time, and is suitable for skin cosmetics with the effects of whitening and resisting aging.
Disclosure of Invention
The invention aims to provide dendrobium candidum extracts, application of the dendrobium candidum extracts in preparation of cosmetics and a preparation method of the dendrobium candidum extracts.
In order to achieve the above purpose of the present invention, the present invention provides the following technical solutions:
a compound ZDL-47 shown by the following structural formula,
cosmetic comprising compound ZDL-47 and cosmetic common base material.
Application of compound ZDL-47 in preparing cosmetics.
A process for the preparation of compound ZDL-47, comprising the steps of: drying dendrobium candidum stems, crushing, soaking in 0-100% ethanol at room temperature for 3 times, concentrating the extract under reduced pressure, dissolving in water, sequentially extracting with ethyl acetate and n-butanol to obtain an ethyl acetate part and an n-butanol part respectively to obtain active site extracts, dissolving the ethyl acetate part, adsorbing the ethyl acetate part to 450g of silica gel 200-300 meshes, performing silica gel column chromatography petroleum ether-acetone gradient elution 15:1-0:1, detecting by TLC, combining into 22 components Fr.1-22, performing normal phase silica gel column chromatography on Fr.11, and performing MCI elution to obtain a skin-care whitening active compound ZDL-49; fr.16 is eluted by normal phase silica gel column and MCI to obtain Fr.16.4, and then eluted by Sephadex LH-20 to obtain skin care and whitening active compound ZDL-23; fr.18 is eluted by normal phase silica gel column, MCI and Sephadex LH-20 to obtain skin-care whitening active compound ZDL-26; fr.19 is eluted by MCI0-100 ethanol to obtain Fr.19.6, and is eluted by Sephadex LH-20 to obtain Fr.19.6.3.2, and is prepared by HPLC to obtain skin-care whitening active compound ZDL-47.
The cosmetic comprises a compound ZDL-23 shown in the following structural formula and a common cosmetic base material,
application of compound ZDL-23 in preparing cosmetics.
A process for the preparation of compound ZDL-23, which process comprises the steps of: drying dendrobium candidum stems, crushing, soaking in 0-100% ethanol at room temperature for 3 times, concentrating the extract under reduced pressure, dissolving in water, sequentially extracting with ethyl acetate and n-butanol to obtain an ethyl acetate part and an n-butanol part respectively to obtain active site extracts, dissolving the ethyl acetate part, adsorbing the ethyl acetate part to 450g of silica gel 200-300 meshes, performing silica gel column chromatography petroleum ether-acetone gradient elution 15:1-0:1, detecting by TLC, combining into 22 components Fr.1-22, performing normal phase silica gel column chromatography on Fr.11, and performing MCI elution to obtain a skin-care whitening active compound ZDL-49; fr.16 is eluted through normal phase silica gel column and MCI to obtain Fr.16.4, which is then eluted through Sephadex LH-20 to obtain skin-care whitening active compound ZDL-23.
The active site enrichment of the dendrobium candidum is prepared by one of the following methods:
cutting the stem of the dendrobium candidum, carrying out reflux extraction twice with 0-100% ethanol (w: v 1:6) for 2h each time, combining the extracting solutions, concentrating under reduced pressure to obtain an extract, mixing the extract with a sample, loading the sample on an MCI column, eluting with 0-100% ethanol, and concentrating under reduced pressure to obtain an active site enrichment substance of the dendrobium candidum;
extracting the dendrobium candidum stem powder with 0-100% ethanol (w: v 1:6) under reflux twice for 2h each time, mixing the extracting solutions, concentrating under reduced pressure to obtain an extract, passing through a macroporous resin D101 column, eluting with 0-100% ethanol, and concentrating under reduced pressure to obtain the active site enrichment of dendrobium candidum.
The active site enrichment of the dendrobium candidum contains the following 4 compounds, the weight percentage of the 4 compounds accounts for 20-40 percent of the total enrichment,
the invention also provides an active site extracted from dendrobium candidum, which is prepared by the following method:
pulverizing dried stem of Dendrobium officinale Kimura et Migo, refluxing with hot water for 3 times, concentrating under reduced pressure to obtain extract, dissolving in water, and dividing into 4 parts, wherein 3 parts are respectively defatted with petroleum ether, deproteinized with chloroform and n-butanol, and deproteinized with ethanol to obtain water extract active site, defatted active site, deproteinized active site, and polysaccharide-removed active site.
The invention also provides compounds ZDL-26, ZDL-47 and ZDL-49 shown in the following structural formula,
the invention also provides a cosmetic which consists of the active site enrichment of the dendrobium candidum and a base material commonly used by the cosmetic.
And the other cosmetic consists of the active site extracted from the dendrobium candidum and common base materials of the cosmetics.
And the other cosmetic is composed of any one or more of the compounds shown in the following structural formula and a base material commonly used by the cosmetic,
the invention also provides application of the dendrobium candidum active site concentrate in preparation of cosmetics.
And the application of the active site extracted from the dendrobium candidum in preparing cosmetics.
And, the use of a compound of the formula in the preparation of a cosmetic,
in addition, the invention provides a preparation method of the active site enrichment of dendrobium candidum, which comprises one of the following steps:
cutting the stem of the dendrobium candidum, carrying out reflux extraction twice with 0-100% ethanol (w: v 1:6) for 2h each time, combining the extracting solutions, concentrating under reduced pressure to obtain an extract, mixing the extract with a sample, loading the sample on an MCI column, eluting with 0-100% ethanol, and concentrating under reduced pressure to obtain an active site enrichment substance of the dendrobium candidum;
extracting the dendrobium candidum stem powder with 0-100% ethanol (w: v 1:6) under reflux twice for 2h each time, mixing the extracting solutions, concentrating under reduced pressure to obtain an extract, passing through a macroporous resin D101 column, eluting with 0-100% ethanol, and concentrating under reduced pressure to obtain the active site enrichment of dendrobium candidum.
A process for the preparation of a compound represented by the following structural formula, the process comprising the steps of: drying dendrobium candidum stems, crushing, soaking in 0-100% ethanol at room temperature for 3 times, concentrating the extract under reduced pressure, dissolving in water, sequentially extracting with ethyl acetate and n-butanol to obtain an ethyl acetate part and an n-butanol part respectively to obtain active site extracts, dissolving the ethyl acetate part, adsorbing to 450g of silica gel 200-300 meshes, performing silica gel column chromatography petroleum ether-acetone gradient elution 15:1-0:1, detecting by TLC, combining into 22 components Fr.1-22, performing normal phase silica gel column chromatography on Fr.11, and performing MCI elution to obtain a skin-care whitening active compound ZDL-49; fr.16 is eluted by normal phase silica gel column and MCI to obtain Fr.16.4, and then eluted by Sephadex LH-20 to obtain skin care and whitening active compound ZDL-23; fr.18 is eluted by normal phase silica gel column, MCI and Sephadex LH-20 to obtain skin-care whitening active compound ZDL-26; fr.19 is eluted by MCI0-100 ethanol to obtain Fr.19.6, and is eluted by Sephadex LH-20 to obtain Fr.19.6.3.2, and is prepared by HPLC to obtain skin-care whitening active compound ZDL-47,
the research of the invention finds that the dendrobium candidum extract and the monomer compound in the dendrobium candidum extract have obvious whitening and anti-aging effects. The activity screening of the invention preliminarily shows that the specific action way is to reduce the generation of melanin in B16 melanocytes by means of DPPH free radical elimination and tyrosinase activity inhibition so as to achieve the effect of skin lightening. The expression of the type I collagen can also be promoted in a mode of eliminating the activity of free radicals and promoting the secretion activity of the collagen, so that the elasticity and the higher water content of the skin are maintained, and the skin aging is delayed.
The invention also provides a preferable preparation method of the dendrobium candidum extract, which comprises the following steps: cutting dried stem of Dendrobium candidum, and extracting with solvent. The solvent is water or ethanol with different concentrations, and methanol, n-butanol, isopropanol, ethylene glycol, 1, 2-propylene glycol, 1, 3-butylene glycol, ethyl acetate, acetone or any combination thereof are not excluded. The extraction method comprises soaking, refluxing, and soaking. And concentrating the extracting solution, and removing pigments to obtain the dendrobium candidum extract.
The dendrobium officinale extract is separated and purified by using various chromatographic methods (normal phase silica gel, reverse phase silica gel, MCI column chromatography, medium pressure preparative chromatography MPLC and high performance liquid chromatography HPLC) to obtain 19 compounds, and the structure of the dendrobium officinale extract is identified by using various spectrum analysis methods (NMR, MS, IR and UV) and reference identification, wherein the structure comprises 4 new compounds.
The literature does not relate to the whitening and anti-aging effects of dendrobium candidum, and the dendrobium candidum is not mentioned to be added into cosmetics as a functional additive. Namely, the dendrobium officinale has the skin beautifying effect, can be used as a functional additive to be added into cosmetics and is used for realizing the effects of whitening and resisting aging.
Drawings
FIG. 1 is a schematic diagram of the structure of the isolated compound of Dendrobium mexicana.
FIG. 2 is a schematic structural diagram of compound ZDL-47.
Detailed Description
The following description will further illustrate the essential features of the present invention by using the embodiments of the present invention in conjunction with the accompanying drawings, but the present invention is not limited thereto.
Example 1
Preparing the dendrobium candidum extract: cutting the stems of the dendrobium candidum into 10g, carrying out reflux extraction twice with 0-100% ethanol (w: v 1:6) for 2 hours each time, combining extracting solutions, concentrating under reduced pressure to obtain 1.2g of extract, mixing the extract with a sample, loading the sample on an MCI (methanol-toluene-ethyl) column, eluting with 0-100% ethanol, concentrating under reduced pressure to obtain 0.8g of the dendrobium candidum active site enrichment, and detecting by HPLC (high performance liquid chromatography), wherein the enrichment contains 4 compounds ZDL-49, ZDL-23, ZDL-26 and ZDL-47 in the following example 4, and the weight percentage of the 4 compounds accounts for 29.77% of the total enrichment.
Example 2
Preparing the dendrobium candidum extract: 10g of dendrobium candidum stem powder, carrying out reflux extraction twice with 0-100% ethanol (w: v 1:6) for 2 hours each time, combining extracting solutions, concentrating under reduced pressure to obtain 1.3g of extract, passing through a macroporous resin D101 column, eluting with 0-100% ethanol, concentrating under reduced pressure to obtain 0.9g of dendrobium candidum active site enrichment, and detecting by HPLC, wherein the enrichment contains 4 compounds ZDL-49, ZDL-23, ZDL-26 and ZDL-47 in the following example 4, and the weight percentage of the 4 compounds accounts for 20.54% of the total enrichment.
Example 3
Drying 1.0kg of Dendrobium candidum stem, pulverizing, refluxing with hot water for 3 times, concentrating under reduced pressure, dissolving the extract in water, and dividing into 4 parts, wherein 3 parts are degreased with petroleum ether respectively; chloroform, n-butanol alcohol deproteinization and ethanol deproteinization to obtain water-extracted skin-care and whitening active site, defatted skin-care and whitening active site, deproteinized skin-care and whitening active site and polysaccharide-removed skin-care and whitening active site.
Example 4
Pulverizing 10.2kg of dry Dendrobium candidum stem, soaking in ethanol (0-100%) at room temperature for 3 times, concentrating the extract under reduced pressure, dissolving in water, sequentially extracting with ethyl acetate and n-butanol to obtain 220g of ethyl acetate fraction and 270g of n-butanol fraction, respectively, and respectively obtaining active fraction extracts. The ethyl acetate fraction (210g) was dissolved, adsorbed to 450g of silica gel (200-300 mesh), and eluted by silica gel column chromatography with a petroleum ether-acetone gradient (15:1-0:1), checked by TLC and combined into 22 fractions (Fr.1-22). Fr.11(6g) is eluted by normal phase silica gel column and MCI to obtain skin-care whitening active compound ZDL-49; fr.16(19g) is eluted by normal phase silica gel column and MCI to obtain Fr.16.4, and then eluted by Sephadex LH-20 to obtain skin-care whitening active compound ZDL-23; fr.18(10g) is eluted by normal phase silica gel column, MCI and Sephadex LH-20 to obtain skin-care whitening active compound ZDL-26; fr.19(20g) is eluted by MCI (0-100 ethanol) to obtain Fr.19.6, and is eluted by Sephadex LH-20 to obtain Fr.19.6.3.2, and is prepared by HPLC to obtain skin-care whitening active compound ZDL-47.
The nuclear magnetism 13C and 1H spectral attribution of the compounds ZDL-26, ZDL-47 and ZDL-49 are respectively shown in tables 5, 6 and 7.
Example 5:
beautifying dendrobium extract and evaluation of whitening and anti-aging activity of single compound in beautifying dendrobium extract
First, experimental cells and reagents
Adult dermal fibroblasts (HDFa) were purchased from Cascade biologics. DMEM (high glucose) medium, PBS, Hank's Balanced Salt Solution (HBSS), streptomycin and Fetal Bovine Serum (FBS) were purchased from Hyclone; 0.25% pancreatin (with EDTA) from Gibico; DPPH, water-soluble vitamin E (Trolox), mushroom tyrosinase, levodopa (L-Dopa) and Kojic Acid (Kojic Acid) were purchased from Sigma; transforming growth factor beta (TGF-beta) was purchased from Peprotech; the collagen ELISA kit is purchased from TaKaRa company; MTS reagent was purchased from Promega corporation.
Second, Experimental methods
DPPH radical scavenging experiment
Mixing the drug to be detected with DPPH (final concentration of 100 mu M) for reaction, setting 3 repeated holes, simultaneously setting a blank control hole without the drug and a Trolox positive control hole, measuring an OD value by an enzyme-linked immunosorbent assay (OD) instrument at 30 ℃ for 1h, wherein the detection wavelength is 515nm, and calculating to obtain the oxidation resistance.
Oxidation resistance (%) (1-experimental well OD)515nmBlank well OD515nm)×100％
2. Tyrosinase activity inhibition assay
Mixing the drug to be detected with L-Dopa, adding tyrosinase (final concentration 25U/mL) to start reaction, setting 3 repeated holes, setting blank control and Kojic Acid positive control which do not contain the drug at the same time, measuring OD value by an enzyme-labeling instrument at room temperature for 5min, and measuring the wavelength at 490 nm. And calculating to obtain the tyrosinase activity inhibition rate.
Tyrosinase activity inhibition (%) [ 1-sample OD490nmExperimental control well OD490nm〕×100
HDFa collagen secretion test
Mixing HDFa cells with a compound to be detected on a 96-hole cell culture plate, and setting a blank control without a medicament and a TGF-beta positive control; culturing at 37 deg.C with 5% CO2 for 3 days, collecting cell culture supernatant, and storing at-80 deg.C; adding MTS, and detecting the OD value of 490nm by adopting an MTS colorimetric method; the secretion of collagen is detected according to the method provided in the collagen ELISA kit, and an enzyme-linked immunosorbent assay (OD) value is measured, wherein the detection wavelength is 450 nm. And calculating to obtain the collagen secretion increasing rate.
The collagen secretion increase rate (%) (experimental well OD450 nm/cell viability/blank well OD450nm-1) × 100%.
Third, experimental results
TABLE 1 in vitro antioxidant Effect of samples
TABLE 2 inhibition of tyrosinase by the samples
TABLE 3 sample promotion of HDFa collagen secretion and cytotoxic Effect
Fourthly, conclusion:
as shown in tables 1 to 3, the DPPH radical scavenging ability, tyrosinase inhibitory ability and collagen secretion promoting ability of 14 samples were evaluated in this experiment. The results show that the samples ZDL-10, ZDL-15, ZDL-23, ZDL-24, ZDL-37, ZDL-44, ZDL-45, ZDL-47, ZDL-50 have strong radical scavenging activity (> 80%, Table 1) at a concentration of 100. mu.g/mL;
tyrosinase inhibitory ability results show that: ZDL-32 and ZDL-49 have better tyrosinase inhibitory activity (> 30%, Table 2)
The results of co-culture with HDFa showed that ZDL-23 and ZDL-37 had some collagen secretion-promoting activity (> 20%, Table 3) at 10. mu.g/mL.
Example 6:
monomer compound (ZDL-32) whitening activity I in beautifying dendrobiumC50Evaluation:
first, experimental reagent
Mushroom tyrosinase, Kojic Acid (Kojic Acid) was purchased from Sigma.
II, an experimental method: tyrosinase activity inhibition
Mixing the drug to be detected with L-Dopa, adding tyrosinase (final concentration 25U/mL) to start reaction, setting 3 repeated holes, setting blank control and Kojic Acid positive control which do not contain the drug at the same time, measuring OD value by an enzyme-labeling instrument at room temperature for 5min, and measuring the wavelength at 490 nm. And calculating to obtain the tyrosinase activity inhibition rate.
Tyrosinase activity inhibition (%) [ 1-sample OD490nmExperimental control well OD490nm〕×100
Thirdly, experimental results:
TABLE 4 inhibitory Effect of ZDL-32 on tyrosinase IC50Value of
TABLE 5 ZDL-26 spectral data
TABLE 6 ZDL-47 spectral data
TABLE 7ZDL-49 spectral data
Table 5 above shows the assignment of the spectrum of the compound ZDL-26 under nuclear magnetism 13C, 1H.
Table 6 shows the assignment of the spectrum of the compound ZDL-47 nuclear magnetism 13C, 1H.
Table 7 shows the assignment of the spectrum of the compound ZDL-49 nuclear magnetism 13C, 1H.
Example 7:
a whitening cream formula (W%) containing the extracted active site of dendrobium candidum or the enriched or enriched active site of dendrobium candidum (hereinafter collectively referred to as active ingredients) obtained in examples 1-4:
the cosmetic with the formula is prepared by a conventional cosmetic preparation method.
Example 8:
an emulsion formulation (W%) containing the extracted active site of dendrobium candidum or the enriched active site or compound (hereinafter collectively referred to as active ingredient) of dendrobium candidum obtained in examples 1-4:
the cosmetic with the formula is prepared by a conventional cosmetic preparation method.
Example 9:
cosmetic water:
water phase: 0.35 g of sodium polyacrylate, 4 g of glycerol, 2.5 g of 1, 3-butanediol, 50.5 g of vitamin B, 0.5 g of arbutin and EDTA-Na 250 mg; an appropriate amount of deionized water is added to 100 ml. The preparation method comprises the following steps: 0.3 g of sodium polyacrylate is dissolved in 70ml of water, stirred and fully swelled. Slowly adding into the prescriptionStirring the rest components continuously; then, 0.5 g of the extracted active site of the dendrobium candidum or the enriched active site of the dendrobium candidum or the compound obtained in the embodiment 1 to 4 is added, and the mixture is stirred to be homogeneous. Adding deionized water to 100ml, and packaging.
Example 10:
repairing cream:
prescription: 6g of glycerin, 1.5 g of carbomer, 1.5 g of triethanolamine, 6g of propylene glycol and 0.2 g of ethyl hydroxybenzoate, 0.5 g of the extract active site of the dendrobium candidum or the enrichment of the active site of the dendrobium candidum obtained in the embodiments 1-4 of the invention and a proper amount of deionized water are added until the total weight is 100 g. The preparation method comprises the following steps: adding carbomer into deionized water, stirring, standing overnight to swell completely, adding glycerol, and adjusting pH with triethylamine to increase gel matrix viscosity. And uniformly mixing the tanshinone extract, the propylene glycol and the deionized water according to the prescription amount. Adding carbomer gel, adding 0.5% essential oil and ethyl hydroxybenzoate, mixing, stirring, adding distilled water, and grinding.
Claims (7)
1. A compound ZDL-47 shown by the following structural formula,
2. cosmetic comprising the compound ZDL-47 according to claim 1 and a cosmetically acceptable base.
3. Use of the compound ZDL-47 according to claim 1 for the preparation of cosmetics.
4. A process for the preparation of compound ZDL-47 according to claim 1, characterized in that it comprises the following steps: drying dendrobium candidum stems, crushing, soaking in 0-100% ethanol at room temperature for 3 times, concentrating the extract under reduced pressure, dissolving in water, sequentially extracting with ethyl acetate and n-butanol to obtain an ethyl acetate part and an n-butanol part respectively to obtain active site extracts, dissolving the ethyl acetate part, adsorbing the ethyl acetate part to 450g of silica gel 200-300 meshes, performing silica gel column chromatography petroleum ether-acetone gradient elution 15:1-0:1, detecting by TLC, combining into 22 components Fr.1-22, performing normal phase silica gel column chromatography on Fr.11, and performing MCI elution to obtain a skin-care whitening active compound ZDL-49; fr.16 is eluted by normal phase silica gel column and MCI to obtain Fr.16.4, and then eluted by Sephadex LH-20 to obtain skin care and whitening active compound ZDL-23; fr.18 is eluted by normal phase silica gel column, MCI and Sephadex LH-20 to obtain skin-care whitening active compound ZDL-26; fr.19 is eluted by MCI0-100 ethanol to obtain Fr.19.6, and is eluted by Sephadex LH-20 to obtain Fr.19.6.3.2, and is prepared by HPLC to obtain skin-care whitening active compound ZDL-47.
5. The cosmetic comprises a compound ZDL-23 shown in the following structural formula and a common cosmetic base material,
6. use of the compound ZDL-23 according to claim 5 for the preparation of cosmetics.
7. Process for the preparation of the compound ZDL-23 according to claim 5, characterised in that it comprises the following steps: drying dendrobium candidum stems, crushing, soaking in 0-100% ethanol at room temperature for 3 times, concentrating the extract under reduced pressure, dissolving in water, sequentially extracting with ethyl acetate and n-butanol to obtain an ethyl acetate part and an n-butanol part respectively to obtain active site extracts, dissolving the ethyl acetate part, adsorbing the ethyl acetate part to 450g of silica gel 200-300 meshes, performing silica gel column chromatography petroleum ether-acetone gradient elution 15:1-0:1, detecting by TLC, combining into 22 components Fr.1-22, performing normal phase silica gel column chromatography on Fr.11, and performing MCI elution to obtain a skin-care whitening active compound ZDL-49; fr.16 is eluted through normal phase silica gel column and MCI to obtain Fr.16.4, which is then eluted through Sephadex LH-20 to obtain skin-care whitening active compound ZDL-23.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010709663.6A CN111825536A (en) | 2018-01-10 | 2018-01-10 | Dendrobium candidum compound and cosmetics and application thereof |
Applications Claiming Priority (2)
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| CN113209059A (en) * | 2021-05-20 | 2021-08-06 | 中国热带农业科学院热带生物技术研究所 | Dendrobium phenanthrene composition and application thereof |
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| CN109820842B (en) * | 2018-11-20 | 2022-01-11 | 中国科学院昆明植物研究所 | Application of yam extract III in preparation of medicines and cosmetics |
| CN109620787A (en) * | 2019-01-30 | 2019-04-16 | 广州诗美化妆品有限公司 | A kind of moisturizing golden hairpin dendrobium extract and the preparation method and application thereof |
| CN110269829A (en) * | 2019-05-12 | 2019-09-24 | 广州芊舟生物科技有限公司 | A kind of anti-aging moisturizing stoste and preparation method thereof |
| CN110898166A (en) * | 2019-12-05 | 2020-03-24 | 广西中医药大学 | Dendrobium candidum granules and preparation method thereof |
| CN111494284A (en) * | 2020-06-01 | 2020-08-07 | 中国科学院昆明植物研究所 | Dendrobium officinale extract processed by special method and application thereof in skin care products |
| CN114831900B (en) * | 2022-05-06 | 2023-01-06 | 中国科学院昆明植物研究所 | Application of bibenzyl monomer compound in cosmetics |
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