CN115715774A - Application of 8-isopentenyl-4' -methoxy flavonol compound - Google Patents
Application of 8-isopentenyl-4' -methoxy flavonol compound Download PDFInfo
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Abstract
The invention discloses an application of an 8-isopentenyl-4 '-methoxy flavonol compound, which is to use the 8-isopentenyl-4' -methoxy flavonol compound as an active ingredient for preparing a medicament or a cosmetic for preventing or/and treating depigmentation diseases. The research result of the invention shows that: the 8-isopentenyl-4' -methoxy flavonol compound can remarkably improve the melanogenesis ability of B16F10 cells of mice and the activity of tyrosinase; particularly, the compound B can obviously promote the melanogenesis capability in the hair of C57BL/6 mice; therefore, the 8-isopentenyl-4' -methoxy flavonol compound disclosed by the invention can be expected to be used as an active ingredient for preparing a pharmaceutical preparation or a cosmetic for preventing or/and treating the depigmentation diseases, and has an important value on the prevention and treatment of the depigmentation diseases.
Description
Technical Field
The invention relates to an application of 8-isopentenyl-4 '-methoxy flavonol compounds, in particular to an application of 8-isopentenyl-4' -methoxy flavonol compounds in preventing or/and treating depigmentation diseases.
Background
Depigmentation is a skin disease named for its characterization. Depigmentation disease refers to the condition that skin and mucosa have lighter patches than normal skin, and is mainly caused by hypopigmentation or depigmentation of skin. In the processes of generation, transfer and degradation of pigment, the metabolism can be affected by any link of the processes of generation, transfer and degradation of pigment, so that the skin color changes, the affected part is milky white, the periphery of the affected part is colored and hyperpigmented, and no subjective symptom exists. Pigment-deficient white spots can occur anywhere throughout the body, but are seen most frequently in exposed areas such as the face, neck, and back of the hand, and in folds of the external genitalia. Most of them are limited, exist in isolation, can be distributed symmetrically, or are distributed along nerves in a band shape, and can be spread over the whole body, leaving only a few normal skins. Can be classified into systemic skin depigmentation such as vitiligo, tuberous sclerosis, piebaldism, and itai-tussio hypopigmentation according to its depigmentation range; non-systemic depigmentation of skin, including eyelid albinism syndrome, phenylketonuria. The treatment of the diseases is difficult, the treatment course is long, and the cure rate is low.
Among them, vitiligo is attracting attention as one of the most representative diseases of depigmentation diseases. The worldwide prevalence of vitiligo is reported to be 0.06% -2.28% ([ J ]. International Journal of Dermatology,2012, 51 (10)), and the prevalence of the population in our country is about 0.1% -2.7% ([ M ]. Chinese clinical Dermatology, 2009 1268-1270. Vitiligo is not accompanied by feelings of uneasiness such as itching and pain, but causes many negative effects in social self-esteem and correspondence, and even causes psychological problems such as anxiety and depression.
To date, the pathogenesis of vitiligo has not been fully elucidated, and is mainly considered to be related to genetics, immunity, neuropsychiatry, metabolite damage, trace element deficiency, and the like ([ J ]. Qatar Medical Journal,2013, 2013 (2)). Clinically, western medicine mainly treats vitiligo by using chemical drugs such as glucocorticoid, calcineurin inhibitor, vitamin D and the like and by physical therapy such as optical therapy, surgical operation and the like (J, modern distance education of Chinese medicine, 2020, 18 (21): 134-136).
The leucoderma has been known in the traditional Chinese medicine for thousands of years, belongs to the category of 'white patch wind', 'leucoderma' and 'piebald' in the traditional Chinese medicine, and is considered to be caused by the interaction of internal factors and external factors, wherein the internal factors are responsible for viscera dysfunction, the external factors are six exogenous pathogenic factors such as wind, cold and dampness, and the internal and external factors are responsible for disharmony of qi and blood, vein and vein stasis and skin striae and skin malnutrition, and the treatment principle is wind dispelling, dampness removing, liver soothing, kidney tonifying, blood activating and stasis removing (Wang Jia Yue, zhang Fengcuan, chua Yuli, wang Ying, li Yuanfeng, zhang Feng teach differentiation and clinical experience summary of leucoderma for treating the leucoderma ([ J ]. World traditional Chinese medicine, 2020, 15 (22): 3471-3474).
The traditional Chinese medicines which are commonly used for treating the leucoderma clinically mainly comprise: fructus psoraleae, radix polygoni multiflori preparata, eclipta, glossy privet fruit, prepared rehmannia root, barbary wolfberry fruit, chinese angelica, szechuan lovage rhizome, danshen root, red paeony root, safflower, epimedium herb and the like, wherein the main raw materials are pungent and warm, and the sweet taste is much; meridian tropism mainly enters liver and kidney meridians and lung and stomach meridians. Play a role in regulating immunity, improving oxidative stress injury, improving melanocyte function, regulating intestinal flora microenvironment, and the like (J. Journal of dermatology, 2015, 22 (06): 443-445 and [ J/OL ]. J of Chinese Experimental and Formulatory science 1-10[2021-06-19 ].
However, according to the found in the literature, the application of the 8-isopentenyl-4' -methoxyflavonols compound in the depigmentation diseases is not reported so far.
Disclosure of Invention
In view of the above problems in the prior art, the present invention aims to provide a use of 8-isopentenyl-4' -methoxyflavonols in preventing or/and treating depigmentation diseases, and provide a new way for treating depigmentation diseases.
The invention relates to an application of 8-isopentenyl-4 '-methoxy flavonol compounds, which is to use 8-isopentenyl-4' -methoxy flavonol compounds as active ingredients to prepare medicines or cosmetics for preventing or/and treating depigmentation diseases.
The 8-isopentenyl-4' -methoxyflavonol compound has a chemical structure general formula shown in a formula I:
In a preferable scheme, the monosaccharide group is any one of rhamnosyl, glucosyl and ribosyl; the oligosaccharide group consists of any 2 or 3 monosaccharide groups of rhamnosyl, glucosyl and ribosyl.
In a further preferable scheme, the 8-isopentenyl-4' -methoxyflavonol compound disclosed by the invention is any one or a combination of more of the following compounds:
depigmenting diseases described in the present invention include, but are not limited to: vitiligo, piebaldism, albinism syndrome, phenylketonuria, canities.
The agents of the present invention may be administered to a patient by a variety of routes of administration, including, but not limited to, oral, transdermal, intramuscular, subcutaneous, and intravenous injection.
Dosage forms of the medicaments of the present invention include, but are not limited to: tablet, capsule, oral liquid, buccal agent, granule, pill, powder, ointment, pellet, suspension, powder, solution, injection, suppository, ointment, plaster, cream, spray, drop, patch, etc.
The medicine of the invention can contain minor ingredients which do not affect the effective components and/or pharmaceutically acceptable carriers and auxiliary materials necessary for various preparations besides the main active components.
The cosmetics according to the present invention include hair care products for blackening hair and skin care products for blackening white spots on skin.
Compared with the prior art, the invention has the following remarkable beneficial effects:
the research result of the invention shows that: the 8-isopentenyl-4' -methoxy flavonol compound can remarkably improve the melanogenesis ability of B16F10 cells of mice and the activity of tyrosinase; in particular, the compound B can obviously promote the melanogenesis capability in the hair of C57BL/6 mice; therefore, the 8-isopentenyl-4' -methoxy flavonol compound disclosed by the invention can be expected to be used as an active ingredient for preparing a pharmaceutical preparation or a cosmetic for preventing or/and treating the depigmentation diseases, and has an important value on the prevention and treatment of the depigmentation diseases.
Drawings
FIGS. 1a to 1F show the toxic effect of 8-isopentenyl-4' -methoxyflavonols with different concentrations on B16F10 cells under 48 hours and 72 hours of action, respectively; wherein: FIG. 1a is Compound A; FIG. 1B is Compound B; FIG. 1C is Compound C; FIG. 1D is Compound D; FIG. 1E is Compound E; FIG. 1F is Compound F;
FIG. 2a shows the effect of different concentrations of 8-prenyl-4 '-methoxyflavonols on the melanin content in B16F10 cells, and FIG. 2B shows the effect of different concentrations of 8-prenyl-4' -methoxyflavonols on the tyrosinase activity in B16F10 cells; in the figure, "A" represents compound A, "B" represents compound B, "C" represents compound C, "D" represents compound D, "E" represents compound E, and "F" represents compound F;
FIG. 3a is a graph showing the relationship between the action time and body weight of each test group of C57BL/6 mice;
FIG. 3b is a graph showing the effect of each test group on the hair on the back of C57BL/6 mice;
FIG. 3c is a graph showing the effect of each test group on tyrosinase activity.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Experimental procedures without specific conditions noted in the following examples, generally according to conventional conditions or according to conditions recommended by the manufacturers.
The 8-isopentenyl-4' -methoxyflavonols (compound A to compound F) used in the examples were purchased from Shanghai Shidan standard technical services, inc., and the purity was higher than 95%.
Example 1 detection of toxicity of various 8-isopentenyl-4' -methoxyflavonols on mouse B16F10 cells
The survival number of B16F10 cells was measured by adding 8-isopentenyl-4' -methoxyflavonols (e.g., compound A to compound F) to B16F10 cells, performing dry prognosis with each drug, adding MTT reagent, and performing normalization calculation, wherein n is 3 or more, P is 0.05, P is 0.01, and P is 0.001.
(1) B16F10 cell culture
The cryopreservation tube frozen with the B16F10 cells was taken out of the liquid nitrogen tank, and quickly placed in a water bath at 37 ℃ with shaking, and completely thawed within 1 min. Adding the melted cell suspension into a centrifuge tube containing 5mL of DMEM medium, and keeping the centrifuge tube at room temperature for 1000 r-min -1 Centrifuging for 5min, removing supernatant, adding 1mL high sugar DMEM medium for resuspension, transferring to a big dish, adding 10% FBS-containing DMEM medium, blowing uniformly, and 5% CO at 37 deg.C 2 And (3) culturing the cells until the cells are attached to the wall, replacing the culture medium for continuous culture, and when the cells grow to 80 percent, carrying out passage, wherein all cells for experiments are kept within 3-20 generations.
(2) Floor board
Count B16F10 cells at 1X 10 4 Cell Density/well inoculation in DMEM 96 well plates containing 10% FBS, at 37 ℃, 5% CO 2 The culture was carried out overnight in an incubator.
(3) Administration of drugs
After the cells were attached to the wall, DMEM changed to 2.5% FBS was used for culturing, and compound A to compound F were added at different concentrations, respectively, and blank control groups were set, and the action time was 48 hours and 72 hours, respectively.
(4) Determination of cell viability
After the expiration of the drug action time, 100. Mu.L of MTT reagent at a concentration of 5mg/mL was added to each well, and after 4 hours of reaction, the absorbance value of each well was measured at 570nm and calculated.
(5) Data analysis
And (3) performing mapping and data analysis by using PRISM software, comparing the differences of different intervention groups by ANOVA analysis, and considering that the differences among the groups have statistical significance when p is less than 0.05.
(6) Results of the experiment
FIGS. 1a to 1F show the toxicity of different concentrations of compounds A to F on B16F10 cells at 48 hours and 72 hours, respectively; from the results shown in FIGS. 1a to 1f, it can be seen that: at concentrations of 100. Mu.M for Compound A (detailed in FIG. 1 a), 100. Mu.M for Compound B (detailed in FIG. 1B), 100. Mu.M for Compound C (detailed in FIG. 1C), 20. Mu.M for Compound D (detailed in FIG. 1D), 6.3. Mu.M for Compound E (detailed in FIG. 1E) and 2.5. Mu.M for Compound F (detailed in FIG. 1F), no significant toxicity to B16F10 cells was observed.
Example 2 examination of the regulatory Effect of various concentrations of 8-isopentenyl-4' -methoxyflavonols on melanin in mouse B16F10 cells
B16F10 cells are used, 8-isopentenyl-4' -methoxy flavonol compounds with different concentrations are added, and after pharmaceutical intervention is carried out for 72 hours, the melanin content and the tyrosinase activity in the cells are measured. All data are expressed as mean ± SEM, n ≧ 3, P <0.05, P <0.01, P <0.001.
(1) B16F10 cell culture
The cryopreservation tube frozen with the B16F10 cells was taken out of the liquid nitrogen tank, and quickly placed in a water bath at 37 ℃ with shaking, and completely thawed within 1 min. Adding the melted cell suspension into a centrifuge tube containing 5mL of DMEM medium, and keeping the centrifuge tube at room temperature for 1000 r-min -1 Centrifuging for 5min, discarding supernatant, adding 1mL high sugar DMEM medium for resuspension, transferring to a big dish, adding DMEM medium containing 10% FBS, blowing uniformly, at 37 deg.C, 5% 2 And (3) culturing the cells until the cells are attached to the wall, replacing the culture medium for continuous culture, and when the cells grow to 80 percent, carrying out passage, wherein all cells for experiments are kept within 3-20 generations.
(2) Floor board
Count B16F10 cells at 5X 10 5 Cell Density/well inoculation in DMEM petri dishes containing 10% FBS, at 37 ℃, 5% CO 2 The culture was carried out overnight in an incubator.
(3) Administration of drugs
After the cells were attached to the wall, DMEM (2.5% FBS) was changed for culture, and compounds A to F were added at different concentrations and allowed to act for 72 hours, respectively; setting IBMX as a positive control drug;
(4) Determination of protein content in cells
The cells after 72h administration were removed from the incubator and washed 3 times with PBS (pH 7.2); adding 300 mu L of cell lysate into each hole, and collecting cells; the collected cells were lysed at 4 ℃ for 20min and then at 14000 r.min at 4 ℃ -1 Centrifuging for 15min, and collecting supernatant for protein content determination:
preparing a BCA working solution for later use by taking a reagent A and a reagent B in the BCA kit according to the volume ratio of 50; a standard protein solution (0.5 mg/mL) was added to a 96-well plate in a ratio of 0; adding a proper volume of sample into a 96-well plate, diluting the sample with PBS (pH 7.2) to make the total volume 20 mu L, adding 200 mu L BCA working solution into each well, and then incubating the mixture for 30min at 37 ℃; OD was measured at 562nm and the protein concentration was calculated.
(5) Determination of melanin content in cells
Adding different concentrations of the drug, culturing for 72h, washing cells with PBS2 times, collecting cells, adding 300 μ L non-denaturing lysate (containing 1nM PMSF), lysing at 4 deg.C for 20min, and then at 4 deg.C 14000 r.min -1 Centrifuging for 15min, and taking the supernatant for melanin content determination:
adding 200 μ L NaOH (containing 10% DMSO) into the melanin precipitate, decocting in 80 deg.C oven for 2 hr, and standing at 14000r min -1 Centrifuging for 10min; about 100. Mu.L of the melanin was taken out and measured for OD at a wavelength of 470nm in a 96-well plate, and the melanin content was calculated.
(6) Determination of tyrosinase Activity in cells
Adding drugs with different concentrations, culturing for 72h, washing with PBS for 2 times, collecting cells in EP tube, adding 300 μ L non-denaturing lysis buffer (containing 1nM PMSF) into each tube, lysing at 4 deg.C for 20min, and further lysing at 4 deg.C and 14000 r.min -1 Centrifuging for 15min, taking the supernatant, and performing tyrosinase activity measurement by using a BCA method:
a volume of 20. Mu.g protein was added to a 96-well plate, and the volume was adjusted to 100. Mu.L with PBS (pH 6.8), and 0.01% g/mL L-DOPA 100. Mu.L was added, and the plate was incubated at 37 ℃ in the absence of light for 60min, and then OD was measured at a wavelength of 475nm, and the relative activity of tyrosinase was calculated.
(7) Data analysis
And (3) performing mapping and data analysis by using PRISM software, comparing the differences of different intervention groups by ANOVA analysis, and considering that the differences among the groups have statistical significance when p is less than 0.05.
(8) Results of the experiment
FIG. 2a shows the effect of different concentrations of 8-prenyl-4 '-methoxyflavonols on the melanin content in B16F10 cells, and FIG. 2B shows the effect of different concentrations of 8-prenyl-4' -methoxyflavonols on the tyrosinase activity in B16F10 cells; from the results shown in fig. 2a and 2b it can be seen that: in B16F10 cells, 8-isopentenyl-4' -methoxyflavonol compounds with different concentrations can promote the generation of melanin content in the B16F10 cells to different degrees, can improve the activity of tyrosinase, and presents certain concentration gradient.
Example 3 examination of the Effect of Compound B on Hydroquinone-induced C57BL/6 mouse model of vitiligo
C57BL/6 mice were purchased from the animal testing center of the university of medicine in shanghai, beijing, kingdom, laboratory of the second floor SPF-grade barrier system, laboratory of the animal testing center of the university of medicine in shanghai, and were fed with sterilized feed and drinking water, the ambient temperature was controlled to (22 ± 2) ° C, 12h light/dark cycle (7/00.
After 7 days of adaptive feeding, the mice were randomly divided into 4 groups, a normal group, a hydroquinone group, a compound B low dose group and a compound B high dose group, 8 mice per group.
(1) Dispensing of drugs
Weighing appropriate amount of hydroquinone, compound B medicine and cream matrix, mixing, stirring to dissolve completely, and making into ointment with concentration of 4
% hydroquinone cream, 0.1% Compound B cream (Low dose), 0.5% Compound B cream (high dose) and 100
% cream base, all stored at 4 deg.C.
(2) Depilation and administration
The weight ratio of 0.1mL:100g, C57BL/6 mice were anesthetized by intraperitoneal injection of 20% urethane;
mixing rosin and paraffin according to the proportion of 1: dissolving the components in the proportion of 1, and smearing the mixture on gauze and sticking the mixture on the back of a mouse when the mixture is cooled to 50-60 ℃. Cooling to a hard state, and tearing off gauze on the back of the mouse to ensure that the hair of the mouse falls off fully;
in the morning, 4% of hydroquinone cream is used for smearing the back of a hydroquinone group mouse every day, and a blank group mouse is not smeared;
in the afternoon every day, 0.1% of the compound B cream is smeared on the back of a low-dose group mouse, and 0.5% of the compound B cream is smeared on the back of a high-dose group mouse until the compound B cream is evenly smeared to cover the back; the blank group and the hydroquinone group do not need to be smeared;
the administration was continued for 50 days, and the body weight was weighed once every 3 days.
(3) Taking pictures and materials
The color change of the hair on the back of each group of mice was photographed, recorded and observed.
The mice were sacrificed, their back hairs were shaved off using a depilator, their back skin was cut off, placed in paraformaldehyde for soaking and fixation.
(4) Determination of tyrosinase Activity in cells
Taking skin tissues of mice, adding a proper amount of protein lysate, and fully grinding the tissues; the supernatant was centrifuged and the tyrosinase activity was measured with reference to example 2.
(5) Data analysis
And (3) performing mapping and data analysis by using PRISM software, comparing the differences of different intervention groups by adopting ANOVA analysis, and considering that the differences among the groups have statistical significance when p is less than 0.05.
(6) Results of the experiment
FIG. 3a shows the relationship between the action time and the body weight of the C57BL/6 mice of each test group, and can be seen from FIG. 3 a: the hydroquinone group, the low dose group of the compound B and the high dose group have no great influence on the body weight of the mice, which shows that the hydroquinone group, the low dose group and the high dose group have no obvious toxicity;
FIG. 3b shows the effect of each test group on the back hair of C57BL/6 mice, as can be seen in FIG. 3 b: before the experiment, all groups are depilated, and the hair follicle cycle is synchronized; after the experiment, after hydroquinone treatment and administration for 50 days, namely about three hair follicle cycles, the hair of the blank group of mice grows normally, namely the hair is dense and black; the hydroquinone group obviously reduces the generation of hair pigment, namely the formation of leucoderma-like gray hair on the back of the mouse, and the low-dose group and the high-dose group of the compound B can effectively promote the hair color of the C57BL/6 mouse to turn black, thereby obviously relieving the leucoderma-like symptoms;
FIG. 3c shows the effect of each test group on tyrosinase activity, as can be seen in FIG. 3 c: the hydroquinone group significantly inhibited tyrosinase activity, while both the low and high dose groups of compound B were effective in promoting tyrosinase activity.
From the above it can be seen that: the 8-isopentenyl-4' -methoxy flavonol compound can remarkably improve the melanogenesis ability of B16F10 cells of mice and the activity of tyrosinase; in particular, the compound B can obviously promote the melanogenesis capability in the hair of C57BL/6 mice; therefore, the 8-isopentenyl-4' -methoxyflavonol compound can be used as an active ingredient for preparing a pharmaceutical preparation or a cosmetic for preventing or/and treating the depigmentation diseases, and has important value for preventing and treating the depigmentation diseases.
Finally, it is necessary to explain here: the above embodiments are only used for further detailed description of the technical solutions of the present invention, and should not be understood as limiting the scope of the present invention, and the insubstantial modifications and adaptations made by those skilled in the art according to the above descriptions of the present invention are within the scope of the present invention.
Claims (6)
1. The application of the 8-isopentenyl-4' -methoxy flavonol compound is characterized in that: the application refers to that 8-isopentenyl-4' -methoxy flavonol compounds are used as active ingredients for preparing medicines or cosmetics for preventing or/and treating depigmentation diseases.
2. Use according to claim 1, characterized in that: the 8-isopentenyl-4' -methoxy flavonol compound has a chemical structure general formula shown in a formula I:
3. Use according to claim 2, characterized in that: the monosaccharide group is selected from any one of rhamnosyl, glucosyl and ribosyl; the oligosaccharide group consists of any 2 or 3 monosaccharide groups of rhamnosyl, glucosyl and ribosyl.
4. The use of claim 1, wherein the 8-isopentenyl-4' -methoxyflavonol compound is any one or a combination of several compounds selected from the group consisting of:
5. use according to claim 1, characterized in that: the depigmentation disease comprises at least one of vitiligo, piebaldism, albinism syndrome, phenylketonuria and canities.
6. Use according to claim 1, characterized in that: the cosmetic is a hair care product for blackening hair or a skin care product for blackening white spots on skin.
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