CN115819378B - Coffee diterpenoid compound and application thereof in preparation of medicines with effects of improving skin cell activity and inhibiting inflammatory injury of skin cells - Google Patents
Coffee diterpenoid compound and application thereof in preparation of medicines with effects of improving skin cell activity and inhibiting inflammatory injury of skin cells Download PDFInfo
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- CN115819378B CN115819378B CN202211227403.0A CN202211227403A CN115819378B CN 115819378 B CN115819378 B CN 115819378B CN 202211227403 A CN202211227403 A CN 202211227403A CN 115819378 B CN115819378 B CN 115819378B
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- Medicines Containing Plant Substances (AREA)
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Abstract
The invention discloses a coffee diterpenoid compound and application thereof in preparation of drugs with the effects of improving skin cell activity and inhibiting inflammatory injury of skin cells. The coffee diterpenoid compound is characterized by having a structure shown in a formula I or a formula II. The composition and the extract comprise coffee diterpenoid compounds with structures shown in the formulas I and II. The coffee diterpenoid compound with the structure shown in the formula I or the formula II or the composition thereof has the effects of improving the activity of skin cells and inhibiting the inflammatory injury of the skin cells; therefore, the coffee diterpenoid compound with the structure shown in the formula I or the formula II or the composition thereof or the extract containing the coffee diterpenoid compound with the structure shown in the formula I and/or the formula II is used as an active ingredient, and has important application value in preparing cosmetics, skin care products or medicines with the effect of improving the activity of skin cells or inhibiting the inflammatory injury effect or anti-inflammatory effect of the skin cells.
Description
Technical Field
The invention relates to the technical field of biomedicine, in particular to a coffee diterpenoid compound and application thereof in preparation of medicines with the effects of improving skin cell activity and inhibiting inflammatory injury of skin cells.
Background
As the first defending barrier of human body, the protective effect of preventing foreign body invasion, bacterial infection and the like is achieved. With the aging, the metabolism of the oxidative free radicals in skin cells becomes slow, and the increase of the oxidative free radicals in cells is closely related to the exposure of environmental pollutants, the irradiation of ultraviolet light and the like. Studies have reported that UVB exposure induces oxidation of unsaturated fatty acids in skin cells to form lipid radicals, which damage the cells, destroy cell membranes, induce protein and enzyme denaturation, and inactivate, which ultimately cause skin aging.
Naturally active small molecules are well known for their excellent ability to scavenge free radicals and have been widely used in the fields of foods, pharmaceuticals, cosmetics, and the like. The anti-inflammatory, antioxidant and skin anti-aging functions of the natural active small molecules are also valued by people, and the natural active small molecules not only can promote metabolism and enhance immunity, but also play an important role in the processes of cell signal transduction, cell fate regulation and the like.
Coffee is a popular dietary supplement, and coffee beans have wide biological activity and are rich in chemical components such as alkaloids, saccharides, organic acids, esters, sterols, diterpenes and the like. Meanwhile, the coffee has higher medicinal value, such as anticancer, anti-inflammatory, antioxidant, liver protecting and the like. The coffee extract has been proved to have antioxidant, immunoregulatory, hypolipidemic and other effects, and is also widely used in cosmetics to exert antioxidant and anti-inflammatory effects. However, whether or not the active small molecules in coffee can alleviate oxidative damage and inflammatory damage of skin cells has been studied and reported.
Disclosure of Invention
In order to overcome at least one technical problem existing in the prior art, the invention firstly provides a coffee diterpenoid compound. Research shows that the coffee diterpenoid compound not only can improve the activity of skin cells, but also can inhibit inflammatory injury of the skin cells.
The technical scheme of the invention is as follows:
a coffee diterpenoid compound, which has a structure shown as a formula I or a formula II;
the inventors have surprisingly found that coffee diterpenoids of the structures shown in formula I and formula II not only can improve the activity of skin cells, but also can inhibit inflammatory injury of skin cells.
The invention also provides a composition which comprises the coffee diterpenoid compounds with the structures shown in the formulas I and II.
The inventors have further surprisingly found in the study that the composition formed by combining the coffee diterpenoid compounds of the structures shown in the formulas I and II has further improved effect of improving the activity of skin cells and inhibiting the inflammatory injury of the skin cells, and the effect of improving the activity of the skin cells and inhibiting the inflammatory injury of the skin cells is significantly higher than that of the natural active small molecule compound of the structure shown in the formula I or II.
Preferably, the weight ratio of the coffee diterpenoid compounds with the structures shown in the formulas I and II is 1-100:1-100.
Further preferably, the weight ratio of the coffee diterpenoid compounds with the structures shown in the formula I and the formula II is 1-10:1-10.
Most preferably, the weight ratio of the coffee diterpenoid compounds with the structures shown in the formula I and the formula II is 1:1.
The invention also provides an extract which comprises the coffee diterpenoid compounds with the structure shown in the formula I and/or the formula II.
Preferably, the weight content of the coffee diterpenoid compounds with the structures shown in the formula I and/or the formula II in the extract is 1-99%.
Further preferably, the coffee diterpenoid compounds with the structures shown in the formula I and/or the formula II account for 30-95% of the weight of the extract.
In a further step, preferably, the coffee diterpenoid compounds with the structures shown in the formula I and/or the formula II are contained in the extract in an amount of 50-90% by weight.
Preferably, the extract is a coffee extract.
The invention also provides application of the coffee diterpenoid compound, the composition or the extract in preparing a product with the effect of improving the activity of skin cells.
The invention also provides application of the coffee diterpenoid compound, the composition or the extract in preparing a product with the effect of inhibiting inflammatory injury of skin cells.
The invention also provides application of the coffee diterpenoid compound, the composition or the extract in preparing a product with an anti-inflammatory effect.
Preferably, the product is a cosmetic, skin care product or pharmaceutical product.
The beneficial effects are that: the invention provides a coffee diterpenoid compound with a brand new structure; research shows that the coffee diterpenoid compound has the effects of improving the activity of skin cells and inhibiting inflammatory injury of the skin cells; in particular to a composition formed by combining coffee diterpenoid compounds with structures shown in a formula I and a formula II, which has the effects of improving the activity of skin cells, inhibiting inflammatory injury of the skin cells, and improving the activity of the skin cells and inhibiting inflammatory injury of the skin cells; the effect of the coffee diterpenoid compound on improving the activity of skin cells and inhibiting the inflammatory injury of the skin cells is obviously higher than that of the coffee diterpenoid compound with a structure shown as a formula I or a formula II. The coffee diterpenoid compound with the structure shown in the formula I or the formula II or the composition thereof has the effects of improving the activity of skin cells and inhibiting the inflammatory injury of the skin cells; therefore, the coffee diterpenoid compound with the structure shown in the formula I or the formula II or the composition thereof or the extract containing the coffee diterpenoid compound with the structure shown in the formula I and/or the formula II is used as an active ingredient, and has important application value in preparing cosmetics, skin care products or medicines with the effect of improving the activity of skin cells or inhibiting the inflammatory injury effect or anti-inflammatory effect of the skin cells.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 shows a coffee diterpenoid compound of the structure shown in formula I 1 H NMR、 13 C NMR and DEPT135 spectra.
FIG. 2 shows a coffee diterpenoid compound of the structure shown in formula I 1 H- 1 H COSY、HMBC and NOESY spectra.
FIG. 3 is a diagram showing the correlation of key atom NOESY of coffee diterpenoid compounds with the structure shown in the formula I, and ECD spectra calculated and tested.
FIG. 4 shows a coffee diterpenoid compound of the structure shown in formula II 1 H NMR spectrum, 13 C NMR and DEPT135 spectra.
FIG. 5 shows a coffee diterpenoid compound of the structure shown in formula II 1 H- 1 H COSY, HMBC and NOESY spectra.
FIG. 6 is a diagram showing the correlation of key atoms NOESY of coffee diterpenoid compounds with the structure shown in the formula II.
FIG. 7 is a graph showing the effect of a composition on human skin fibroblast viability and coffee diterpene composition on UVB-exposed human skin fibroblast viability.
Fig. 8 is a graph of the effect of a composition on UVB-exposed human skin fibroblast inflammatory factor secretion.
FIG. 9 is a graph showing the effect of compositions on expression of protein associated with NF- κB and NLRP3 signaling pathways of UVB-exposed human skin fibroblasts.
Fig. 10 is a graph showing the effect of the composition on the secretion of inflammatory factors by skin cells of UVB-exposed mice.
FIG. 11 is a graph showing the effect of compositions on NF- κB and NLRP3 signaling pathway associated protein expression in UVB-exposed mouse skin cells.
Detailed Description
The technical scheme of the present invention will be clearly and completely described in the following examples. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1 Process for the preparation of coffee diterpenoids of the structures of formula I and formula II
(1) 1kg of coffee beans (raw) is crushed, leakage extraction is carried out by using 15 times of ethanol with the volume fraction of 50%, and the decompression concentration extract is combined to obtain extractum.
(2) The extract was suspended with water to obtain suspension, and extracted with ethyl acetate and chloroform, respectively. The extract was lyophilized to obtain ethyl acetate, chloroform and water layer extract, respectively.
(3) The ethyl acetate extract was separated by silica gel column chromatography and eluted with 5 gradients of chloroform-methanol (100:10; 100:30; 100:50; 100:70; 100:90) to give 5 fractions (Fr.1-5), respectively.
(4) Gradient eluting Fr.3 (30 g) with 5 gradients of chloroform-methanol (100:20; 100:40; 100:60; 100:80; 100:100) to obtain 5 fractions (Fr.3-1-3-5); separating and purifying Fr.3-4 by preparative HPLC to obtain coffee diterpenoid compound (2.21 g) with structure shown in formula I and coffee diterpenoid compound (2.14 g) with structure shown in formula II;
the specific conditions for preparative HPLC were:
RP-HPLC (Agilent 1200 HPLC) was performed on a Zorbax, SB C-18 column (9.4X105 mm,5 μm). The eluting solvent system consisted of water-trifluoroacetic acid (solvent A;100:0.1, v/v) and acetonitrile-trifluoroacetic acid (solvent B;100:0.1, v/v). Gradient elution with 30% to 60% solvent B was used, with a detection wavelength set at 300nm at a flow rate of 5.0mL/min for 25 min; collecting eluent corresponding to chromatographic peak at 11.87min, concentrating and drying to obtain coffee diterpenoid compound with structure shown in formula I; collecting eluent corresponding to chromatographic peak at 10.15min, concentrating, and drying to obtain coffee diterpenoid compound with structure shown in formula II.
The structural analysis of the coffee diterpenoid compound with the structure shown in the formula I is as follows: white powder, HR-ESI-MS m/z 439.2481[ M+Na ]] + (calcd for C 25 H 36 NaO 5 439.2455 Suggesting that the compound formula is C 25 H 36 O 5 The molecular weight is 416.
1 H NMR(300MHz,CDCl 3 ) Spectrum (fig. 1A), compound has 4 methyl proton signals [ delta ] H 1.48(3H,s),1.33(3H,d,J＝5.4Hz),1.24(3H,s),1.01(3H,s)]Proton signal [ delta ] of 2 olefins H 4.77(1H,s),4.72(1H,s)]And hydrogen proton signals [ delta ] of 2 oxygen-linked carbons H 4.46(1H,dd,J＝12.0,4.5Hz),3.34(1H,dd,J＝10.8,5.4Hz)]。
13 C NMR(75MHz,CDCl 3 ) The spectra (FIG. 1B) and DEPT spectra (FIG. 1C) were analyzed, the compound had 4 methyl groups, 9 methylene groups, 5 methine groups, and a total of 25 carbon signals. Including 3 carbon oxygen signals (δc 80.5,58.2,57.8), 2 carbonyl carbon signals (δc 179.9,171.5) and 2 double bond carbon signals (δc 155.5,103.7).
From the slave 1 H- 1 H-3 (delta) can be seen in the H COSY spectrum (FIG. 2A) H 4.47 And H2-2 (delta) H 2.33,1.75) have relevance.
In the HMBC spectra (FIG. 2B), H-3 and C-19 (delta) can be observed C 179.9)、C-1'(δ C 171.5)、C-4(δ C 48.0)、C-18(δ C 24.0 A) correlation. It was thus demonstrated that the (2 'R,3' S) -or (2 'S,3' R) -2',3' -epoxy-2-methylbutyl substituent in the structure of the compound is attached at the C-3 position.
In the NOESY spectrum (FIG. 2C), H-3 (delta) can be observed H 4.47 Respectively with H-5 (delta) H 1.09)、H-18(δ H 1.24 Related so that H-3 is on the same side as H-5, H-18. At the same time, H-4' (delta) H 1.33 With H-5' (delta) H 1.48 H-4 'is on the same side as H-5' (fig. 3A).
The ECD pattern of this compound was similar to that of the ECD calculated for the 3R,4S,5S,8S,9R,10S,13R,2'R,3' S configuration (FIG. 3B), with a positive Cotton effect at 226nm, thus determining the absolute configuration of the compound as 3R,4S,5S,8S,9R,10S,13R,2'R,3' S. Based on the analysis and the map information, the coffee diterpenoid compound with the structure shown in the formula I is identified and named as coffee diterpenoid-1.
The structural analysis of the coffee diterpenoid compound with the structure shown in the formula II is as follows: white powder, HR-ESI-MS m/z 469.2360[ M+Na ]] + (calcd for C 29 H 34 NaO 4 469.2349 Combined with NMR spectrum of the compound, suggesting that the compound has formula C 29 H 34 O 4 The molecular weight is 446.
1 H NMR(300MHz,CDCl 3 ) In the spectrum (FIG. 4A), the compound has a benzene ring structural fragment [ delta ] H 7.46-7.44(2H,overlapped),7.23-7.16(3H,overlapped)]Proton signal [ delta ] of 5 olefins H 7.64(1H,d,J＝15.9Hz),6.38(1H,d,J＝15.9Hz),5.24(1H,s),4.91(1H,br s),4.80(1H,br s)]2 methyl unimodal proton signals [ delta ] H 1.32(3H,s),1.16(3H,s)]Hydrogen proton signal [ delta ] of 1 oxygen-carbon H 4.73(1H,dd,J＝11.7,4.2Hz)]。
13 C NMR(75MHz,CDCl 3 ) Spectra (fig. 4B) and DEPT spectra (fig. 4C), compounds have 2 methyl groups, 8 methylene groups, 11 methine groups, 8 quaternary carbons, and a total of 29 carbon signals.
1 H- 1 H COSY spectrum (FIG. 5A), H-11 (delta) H 5.24 And H2-12 (delta) H 2.59,2.40) are provided.
HMBC spectra (FIG. 5B), H-11 and C-13 (delta) C 41.3),H2-7(δ H 2.00,1.51)，H2-15(δ H 2.60,2.19)/H-20(δ H 1.16 And C-9 (delta) C 158.2 And thus demonstrates the manner of connection between C-9 and C-11. NOESY spectra (FIG. 5C), H-3 (delta) H 4.73 Respectively with H-5 (delta) H 1.82)、H-18(δ H 1.32 Related so that H-3 is on the same side as H-5, H-18 (FIG. 6).
In summary, the absolute configuration of the compound is 3R,4S,5S,8S,10S,13R. And (3) combining the information and analysis of the spectrograms, identifying the coffee diterpenoid compound with the structure shown in the formula II, and naming the coffee diterpenoid compound as coffee diterpenoid-2.
Example 2 coffee extract
(1) 1kg of coffee beans (raw), crushing, extracting with 15 times of ethanol with volume fraction of 50%, mixing the extractive solutions, and concentrating under reduced pressure to obtain extract;
(2) The extract was suspended with water to obtain suspension, and extracted with ethyl acetate and chloroform, respectively. Freeze-drying the extract to obtain ethyl acetate, chloroform and water layer extract respectively; and (5) taking ethyl acetate layer extractum to obtain the coffee extract.
Example 3 composition
And uniformly mixing the coffee diterpene-1 and the coffee diterpene-2 according to the mass ratio of 1:1 to obtain the composition.
Experimental example 1 experiment for improving skin cell Activity
Human skin fibroblasts were cultured in MEM medium (containing 5% fetal bovine serum), 5% CO 2 Culturing in incubator at 37deg.C with humidity of 95%. Seeding cells in 96-well plates (1×10) 3 After cell attachment, 200. Mu.g/mL of coffee diterpene-1 (FT-1), coffee diterpene-2 (FT-2) and 10. Mu.L of a composition (composition comprising coffee diterpene-1 and coffee diterpene-2 in a mass ratio of 1:1) were added, respectively, to thereby add the same volume of PBS buffer as a blank. Cells were cultured for 24h after addition of coffee diterpene-1, coffee diterpene-2 and the composition solution, and CCK 8 was assayed for cell activity.
Experimental results show (figure 7A), after the coffee diterpene-1, the coffee diterpene-2 and the composition are co-cultured with the human skin fibroblasts, the cell viability of the human skin fibroblasts is greatly improved, which indicates that the coffee diterpene-1, the coffee diterpene-2 and the composition have great improvement effect on the viability of the human skin fibroblasts cultured in vitro.
The cell viability of the coffee diterpene-1, coffee diterpene-2 and composition groups was increased by 11.3% (p < 0.05), 9.27% (p < 0.05) and 20.5% (p < 0.01), respectively, compared to the placebo group. Meanwhile, the composition has better activity than coffee diterpenoid-1 and coffee diterpenoid-2 under the same concentration in terms of improving the activity of human skin fibroblasts.
Experimental example 2 experiments for inhibiting inflammatory injury of skin cells caused by Ultraviolet (UVB) irradiation
Human skin fibroblasts in MEM medium (5% fetal bovine serum) in 5% CO 2 The culture was carried out overnight in an incubator at 37℃with a humidity of 95%. Seeding cells in 96-well plates (1×10) 3 Well), after cell attachment, UVB irradiation. The irradiation intensity of UVB is 5.0X10 -5 J/cm 2 The irradiation light source was 14cm from human skin fibroblasts. The cell culture liquid is sucked off during irradiation, PBS is used for washing for 2 times, and a small amount of covering bottom surface is added to avoid drying. The culture plate is irradiated under water bath at room temperature to avoid overheat after irradiation, PBS is discarded after irradiation, and DMEM culture medium or coffee diterpene-1 (FT-1), coffee diterpene-2 (FT-2) and composition (composition comprising coffee diterpene-1 and coffee diterpene-2 according to the mass ratio of 1:1) solution (400 mug/mL) are added again for continuous culture24h. Then, collecting cells and culture solution, detecting the cell viability by using a CCK 8 kit, and detecting the content of relevant inflammatory cytokines by using an ELISA kit; western blotting detects changes in the relevant proteins.
The experimental results (fig. 7B) show a significant decrease in human skin fibroblast viability following UVB exposure, indicating that UVB exposure damages human skin fibroblasts. Compared with the UVB exposure group, the activity of the human skin fibroblasts is respectively improved by 8.93 percent (p < 0.05), 9.44 percent (p < 0.05) and 15.6 percent (p < 0.01) after the treatment by the coffee diterpenoid-1, the coffee diterpenoid-2 or the composition thereof, which shows that the coffee diterpenoid-1, the coffee diterpenoid-2 and the composition thereof have certain inhibitory activity on the injury and the decrease of the cell activity of the human skin fibroblasts caused by the UVB exposure. Further analysis shows that the composition of the coffee diterpenoid-1 and the coffee diterpenoid-2 has better activity than the coffee diterpenoid-1 or the coffee diterpenoid-2 with the same concentration in terms of inhibiting injury caused by human skin fibroblasts caused by UVB exposure and improving cell viability. We speculate that coffee diterpene-1 and coffee diterpene-2 may act synergistically by combination, thereby better inhibiting human skin fibroblast damage caused by UVB exposure and improving cell viability.
Further, we examined the effect of coffee diterpene-1, coffee diterpene-2 and combinations thereof on the increased secretion of human skin fibroblast inflammatory factor caused by UVB exposure.
The results of the experiment are shown in FIG. 8, in which human skin fibroblast inflammatory factor secretion was increased after UVB irradiation, compared to the blank control group (blank group, IL-4, IL-6, IL-13, TNF-. Alpha., IFN-. Gamma.and PGE2 content were set to 100%). It is suggested that UVB irradiation damages cells and induces cellular inflammatory responses, which in turn increase inflammatory cytokine secretion. IL-4, IL-6, IL-13, TNF- α, IFN- γ and PGE2 levels increased by 151% (p < 0.01), 125% (p < 0.01), 232% (p < 0.01), 101% (p < 0.01), 112% (p < 0.01), 88.4% (p < 0.01), respectively, after UVB exposure compared to the blank. Whereas, after treatment with coffee diterpene-1, coffee diterpene-2 and combinations thereof, UVB radiation-induced increases in human skin fibroblast inflammatory factor secretion were inhibited; it is demonstrated that coffee diterpene-1, coffee diterpene-2 and the composition can inhibit the excessive secretion of human skin fibroblast inflammatory factor induced by UVB irradiation, thereby relieving inflammatory reaction induced by UVB irradiation and reducing inflammatory injury. Further analysis and experiment results show that under the condition of the same concentration, the composition of the coffee diterpenoid-1 and the coffee diterpenoid-2 can inhibit the excessive secretion activity of human skin fibroblast inflammatory factors induced by UVB irradiation, and has better effect than the single use effect of the coffee diterpenoid-1 or the coffee diterpenoid-2. Meanwhile, the composition of the coffee diterpenoid-1 and the coffee diterpenoid-2 can inhibit the secretion of human skin fibroblast histamine induced by UVB irradiation, and the composition of the coffee diterpenoid-1 and the coffee diterpenoid-2 can inhibit the secretion activity of the human skin fibroblast histamine induced by UVB irradiation to be stronger than that of the coffee diterpenoid-1 or the coffee diterpenoid-2 under the condition of the same concentration.
The experimental results are shown in FIG. 9, in which human skin fibroblasts NF- κB and NLRP3 signaling pathways are activated after UVB exposure, IKKKα, IKKβ, IκBα and p65 protein phosphorylation is increased, and NLRP3 inflammatory small body related Caspase-1, ASC and NLRP3 protein expression is significantly increased compared with the blank control group. We speculate that UVB exposure damages human skin fibroblasts and induces an inflammatory response, probably by activating NF- κb and NLRP3 signaling pathways and thereby inducing inflammatory cytokine overexpression. While activation of human skin fibroblast NF- κB and NLRP3 signaling pathway by UVB exposure is inhibited after treatment with coffee diterpene-1, coffee diterpene-2 and their compositions, we speculate that coffee diterpene-1, coffee diterpene-2 and their compositions can inhibit activation of human skin fibroblast NF- κB and NLRP3 signaling pathway by UVB exposure, thereby inhibiting UVB exposure induced inflammatory injury of human skin fibroblasts. Compared with coffee diterpenoid-1, coffee diterpenoid-2 and coffee extract groups, the composition has better inhibitory activity on activation of human skin fibroblast NF- κB and NLRP3 signaling pathway caused by UVB exposure under the same concentration condition.
Experimental example 3 experiments to inhibit inflammatory injury to mouse skin caused by UVB exposure
Mice (nude mice) were randomly divided into 6 groups of 8: blank control group: no treatment was given; UVB control group: the UVB irradiation method is the same as that of each medicine without any medicineA group; UVB irradiation +100mg/mL coffee diterpene-1 (FT-1) solution group; UVB irradiation +100mg/mL coffee diterpene-2 (FT-2) solution group; UVB irradiation +100mg/mL composition (composition of coffee diterpene-1 and coffee diterpene-2 in a mass ratio of 1:1) solution group; UVB irradiation +100mg/mL coffee bean extract solution set (FTT). The above groups were administered at a back area of 2cm x 2cm of skin of mice 1 day before the start of the experiment after 20min of the above corresponding drugs were applied to 500mJ/cm 2 UVB irradiation, 1 time for 1 day, 4 weeks in succession, cervical dislocation sacrificed mice. Taking skin tissues of the irradiated part of the mice, shearing, referring to ELISA detection kit using instructions, detecting the related inflammatory factors (IL-4, TNF-alpha, IL-6, IFN-gamma, PGE2 and IL-13) and histamine content changes in the skin of the mice, and detecting the expression changes of NF-kappa B and NLRP3 signal path related proteins in skin cells of the mice.
Analysis of results:
the results of the experiment are shown in FIG. 10, in which the secretion of inflammatory factors by skin cells of mice after UVB exposure was significantly increased compared to the blank control group (IL-4, IL-6, IL-13, TNF-. Alpha., IFN-. Gamma.and PGE2 content were set to 100%). Compared to the placebo group, the inflammatory factor secretion of the skin cells of the mice was increased by 201% (p < 0.01), 152% (p < 0.01), 252% (p < 0.01), 125% (p < 0.01), 158% (p < 0.01), 104% (p < 0.01) after UVB exposure. We speculate that UVB exposure damages skin cells and induces an inflammatory response. Whereas the increase in inflammatory factor secretion of mouse skin cells by UVB exposure was inhibited following treatment with coffee diterpene-1, coffee diterpene-2 and phase compositions, we speculate that coffee diterpene-1, coffee diterpene-2 and compositions thereof inhibit the inflammatory response and induced inflammatory damage of mouse skin cells by UVB exposure. The inhibition of excessive secretion of inflammatory factors by mouse skin cells caused by UVB exposure was most pronounced compared to the coffee diterpene-1, coffee diterpene-2 and coffee extract groups. The IL-4, IL-6, IL-13, TNF-alpha, IFN-gamma and PGE2 content was reduced by 47.1% (p < 0.01), 46.8% (p < 0.01), 42.8% (p < 0.01), 44.4% (p < 0.01), 59.1% (p < 0.01), 9.71%, respectively, after treatment of the coffee diterpene-1, coffee diterpene-2 compositions compared to the UVB-exposed group. Meanwhile, as a result of the analysis experiment, it was found that the coffee extract did not show a significant inhibitory effect, although it was able to inhibit the secretion of inflammatory factors caused by UVB exposure. Meanwhile, the composition of the coffee diterpenoid-1 and the coffee diterpenoid-2 can inhibit the secretion of mouse skin cell histamine induced by UVB irradiation, and the composition of the coffee diterpenoid-1 and the coffee diterpenoid-2 can inhibit the secretion activity of mouse skin cell histamine induced by UVB irradiation to be stronger than that of the coffee diterpenoid-1 or the coffee diterpenoid-2 under the condition of the same concentration and stronger than that of the coffee bean extract under the condition of the same concentration.
The experimental results are shown in FIG. 11, in which NF- κB and NLRP3 signaling pathways are activated in the skin cells of mice after UVB exposure, and in which IKKK α, IKK β, IκB α and p65 protein phosphorylation is increased, and further, caspase-1, ASC and NLRP3 protein expression in the skin cells of mice after UVB exposure is also significantly increased. We speculate that UVB exposure damages mouse skin cells and induces an inflammatory response and excessive secretion of inflammatory factors may be achieved by activating NF- κb and NLRP3 signaling pathways in mouse skin cells. In this experiment, activation of NF- κB and NLRP3 signaling pathways in mouse skin cells induced by UVB exposure was inhibited after treatment with coffee diterpene-1, coffee diterpene-2, coffee extract and composition, we speculate that coffee diterpene-1, coffee diterpene-2, coffee extract and composition can inhibit activation of NF- κB and NLRP3 signaling pathways in mouse skin cells caused by UVB exposure, and further inhibit inflammatory injury in mouse skin cells induced by UVB exposure. Compared with coffee extract, coffee diterpenoid-1, coffee diterpenoid-2 and the composition have more obvious inhibition effect on NF- κB and NLRP3 signal pathway activation of mouse skin cells caused by UVB exposure. Furthermore, under the condition of the same concentration, the activation inhibition activity of the coffee diterpenoid-1 and coffee diterpenoid-2 composition on NF- κB and NLRP3 signal paths of mouse skin cells caused by UVB exposure is stronger than that of the coffee diterpenoid-1 and coffee diterpenoid-2 which are used independently, and the coffee diterpenoid-1 and coffee diterpenoid-2 probably exert synergistic effects to inhibit the NF- κB and NLRP3 signal paths of the mouse skin cells.
Finally, it is noted that the above-mentioned preferred embodiments are only intended to illustrate rather than limit the invention, and that, although the invention has been described in detail by means of the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the scope of the invention as defined by the appended claims.
Claims (4)
1. A composition comprising a coffee diterpenoid compound having a structure according to formulas i and ii; the weight ratio of the coffee diterpenoid compounds with the structures shown in the formula I and the formula II is 1:1;
2. use of a composition according to claim 1 for the preparation of a product having an effect of increasing the viability of skin cells.
3. Use of a composition according to claim 1 for the preparation of a product having an effect of inhibiting inflammatory lesions of skin cells.
4. Use according to claim 2 or 3, wherein the product is a cosmetic, skin care or pharmaceutical product.
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| CN114907199A (en) * | 2022-06-17 | 2022-08-16 | 诺斯贝尔化妆品股份有限公司 | Anti-inflammatory and antipruritic dandelion diterpenoid compound and preparation method and application thereof |
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