CN117326967A - Pterocarpus santalinus seed oil ceramide and synthesis method and application thereof - Google Patents

Pterocarpus santalinus seed oil ceramide and synthesis method and application thereof Download PDF

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CN117326967A
CN117326967A CN202310051745.XA CN202310051745A CN117326967A CN 117326967 A CN117326967 A CN 117326967A CN 202310051745 A CN202310051745 A CN 202310051745A CN 117326967 A CN117326967 A CN 117326967A
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ceramide
seed oil
acid
sandalwood
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杨超文
叶柳
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Shenzhen Dikeman Biotechnology Co ltd
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Abstract

The invention belongs to the technical field of biological medicines, and discloses a sandalwood seed oil ceramide which is obtained by reacting a sandalwood seed oil fatty acid with a sphingosine compound, wherein the sphingosine compound is selected from sphingosine, phytosphingosine and dihydrosphingosine. The sandalwood seed oil ceramide has excellent performances in the aspects of repairing natural skin barriers, anti-inflammatory, tissue healing, anti-aging and the like, and has wide application prospects in the fields of cosmetics, health-care products, biological medicines and the like.

Description

Pterocarpus santalinus seed oil ceramide and synthesis method and application thereof
Technical Field
The invention belongs to the technical field of biological medicines, and particularly relates to a sandalwood seed oil ceramide and a synthesis method and application thereof.
Background
Ceramides (ceramides, also known as molecular nails) naturally occur in the skin and are very important components of the skin barrier (stratum corneum), in amounts of up to 40-50 wt.%, ceramides are a class of sphingolipids consisting of long-chain bases of sphingosine and fatty acids, in which the carbon chain length, unsaturation and number of hydroxyl groups of the sphingosine moiety, fatty acid moiety are all variable, and ceramides represent a class of compounds. Ceramide has excellent properties in regulating skin barrier function, recovering skin moisture, enhancing adhesion between skin keratinocytes, and the like.
Because of the importance of ceramides, many cosmetic and pharmaceutical companies are researching and developing corresponding products. The natural plant-derived ceramide can form an effective skin barrier to prevent water loss and resist external damage due to the more sustainable and more environment-friendly raw material source and the characteristics similar to the skin ceramide components, and can become a next-generation environment-friendly, safe and reliable ceramide product.
The sandalwood seed oil is a vegetable oil extracted from the seeds of the sandalwood, contains abundant unsaturated fatty acids, and comprises: oleic acid, linolenic acid, stearic acid, etc., and the sandalwood seed oil contains active ingredients such as flavone, polyphenol, vitamin, siemens alkynoic acid, nervonic acid, etc. The sandalwood seed oil has extremely high nutritive value, can resist aging, promote cell renewal and enable skin to be smoother and tighter. The long-chain fatty acid also brings good affinity to moisten and moisturize the skin. Studies show that the sandalwood seed oil can improve premature senility caused by dry skin, increase the moisture content of skin and improve sebaceous gland tissue function, is a good raw material for anti-aging and skin moisturizing products, is suitable for being added into lipstick, treats damaged, fragile and dry hair, and can be added into acne products and soaps. In addition, the sandalwood seed oil is anti-inflammatory oil for treating skin diseases, and has good effect of relieving eczema dermatitis, skin redness and swelling and rash.
Disclosure of Invention
The invention aims to provide ceramide synthesized by utilizing plant-derived rosewood seed oil fatty acid.
Another object of the present invention is to provide a method for synthesizing a sandalwood seed oil ceramide, which uses a naturally plant-derived and readily available sandalwood seed oil fat or a sandalwood seed oil fatty acid as a raw material.
It is another object of the present invention to provide the use of a sandalwood seed oil ceramide.
In order to achieve one of the above purposes, the present invention adopts the following technical scheme:
in a first aspect of the invention, a sandalwood seed oil ceramide is obtained by reacting a sandalwood seed oil fatty acid with a sphingosine compound selected from the group consisting of sphingosine, phytosphingosine, sphinganine.
The reaction can be chemical synthesis reaction (as detailed below), or microbial fermentation method, i.e. using Pichia pastoris or Saccharomyces cerevisiae, fermenting under certain environment to obtain sphingosine compound, and adding fatty acid to obtain ceramide; or taking the sandalwood seed oil as a raw material, selecting a proper strain, and fermenting to obtain the sandalwood seed oil ceramide.
Sphingosine refers to 2-amino-4-octadecene-1, 3-diol, phytosphingosine refers to 2-amino-octadecane-1, 3, 4-triol, and dihydrosphingosine refers to 2-amino-octadecane-1, 3-diol.
Further, the sandalwood seed oil fatty acid is obtained by hydrolyzing the sandalwood seed oil grease.
Further, the sandalwood seed oil fatty acid contains 50-75wt% of oleic acid.
Further, the sandalwood seed oil fatty acid contains 15-40 wt% of linolenic acid.
Further, the sandalwood seed oil fatty acid contains 0.5 to 10 weight percent of stearic acid.
Further, the sandalwood seed oil fatty acid contains 0 to 15wt% of siemens acid, preferably 5 to 15wt%.
Further, the sandalwood seed oil fatty acid contains 0 to 15wt% of the nervonic acid, preferably 7 to 12wt%.
Further, the sandalwood seed oil fatty acid contains 0 to 2 weight percent of behenic acid, 0 to 1 weight percent of palmitic acid and 0 to 1 weight percent of linoleic acid.
The composition of the sandalwood seed oil fatty acid is as follows: 50 to 75 weight percent of oleic acid, 15 to 40 weight percent of linolenic acid, 0.5 to 10 weight percent of stearic acid, 0 to 15 weight percent of siemens acetylenic acid, 0 to 15 weight percent of nervonic acid, 0 to 2 weight percent of behenic acid, 0 to 1 weight percent of palmitic acid and 0 to 1 weight percent of linoleic acid.
The main component of the rosewood seed oil fatty acid is oleic acid, other fatty acids comprise linolenic acid and stearic acid, which are essential components, are influenced by plant varieties, soil, climate, production places, picking seasons and extraction processes, the content of each component is different, and Siemens alkynoic acid, nervonic acid, behenic acid, palmitic acid and linoleic acid are not necessarily contained, and are optional components or unnecessary components.
The composition of the sandalwood seed oil ceramide comprises: oleic acid ceramide, linolenic acid ceramide, stearic acid ceramide; because fatty acids all participate in the same reaction, the mass ratio of ceramide after the reaction is not changed greatly, so the composition of the ceramide is similar to that of the fatty acid of the rosewood seed oil, and the composition of the ceramide of the rosewood seed oil is as follows: 50 to 75 weight percent of oleic acid ceramide, 15 to 40 weight percent of linolenic acid ceramide and 0.5 to 10 weight percent of stearic acid ceramide. The content of each component is different due to the different content of each fatty acid in the rosewood seed oil fatty acid or the grease. In addition, the sandalwood seed oil ceramide also comprises ceramide obtained by reacting one or more of siemens acetylenic acid, nervonic acid, behenic acid, palmitic acid and linoleic acid with a sphingosine compound, namely, the ceramide also comprises 0-15wt% of siemens acetylenic acid ceramide, 0-15wt% of nervonic acid ceramide, 0-2wt% of behenic acid ceramide, 0-1wt% of palmitic acid ceramide and 0-1wt% of linoleic acid ceramide. The sandalwood seed oil ceramide also includes compounds which exist in the sandalwood seed oil fatty acid but do not react with sphingoid compounds, such as flavones, polyphenols, vitamins, and the like.
The composition of the sandalwood seed oil ceramide comprises: oleic acid ceramide, linolenic acid ceramide, stearic acid ceramide; 50-75wt% of oleic acid ceramide, 15-40wt% of linolenic acid ceramide and 0.5-10wt% of stearic acid ceramide.
Further, the sandalwood seed oil ceramide includes not more than 15wt% of siemens acid ceramide, not more than 15wt% of ceramide, not more than 2wt% of behenic acid ceramide, not more than 1wt% of palmitoleic acid ceramide and not more than 1wt% of linolic acid ceramide, especially 0.1 to 15wt% of siemens acid ceramide, 0.1 to 15wt% of ceramide, 0.1 to 2wt% of behenic acid ceramide, 0.1 to 1wt% of palmitoleic acid ceramide and 0.1 to 1wt% of linolic acid ceramide.
The sandalwood seed oil ceramide also comprises siemens alkynoic acid ceramide and nervonic acid ceramide, which are two unique ceramides, and the content of the ceramides is not more than 15wt%, preferably 5-15 wt% and 7-12 wt% respectively.
The oleum Santali albi ceramide also comprises behenic acid ceramide, palmitic acid ceramide and linoleic acid ceramide, and the content of the behenic acid ceramide, the palmitic acid ceramide and the linoleic acid ceramide is not more than 2wt%, 1wt% and 1wt% respectively.
Oleic acid ceramide is obtained by condensation reaction of oleic acid and sphingosine compounds, and comprises oleic acid phytosphingosine ceramide, oleic acid sphingosine ceramide and oleic acid dihydrosphingosine ceramide; the linolenic acid ceramide is obtained by condensation reaction of linolenic acid and sphingosine compounds, and comprises linolenic acid phytosphingosine ceramide, linolenic acid sphingosine ceramide and linolenic acid dihydrosphingosine ceramide; stearic acid ceramide is obtained by condensation reaction of stearic acid and sphingosine compound, and comprises stearic acid phytosphingosine ceramide, stearic acid sphingosine ceramide and stearic acid dihydrosphingosine ceramide; siemens acid ceramide, nervonic acid ceramide, behenic acid ceramide, palmitic acid ceramide, linoleic acid ceramide, and the like.
In a second aspect of the invention, a method for synthesizing a sandalwood seed oil ceramide comprises the following steps:
under the conditions of a condensing agent and a catalyst, the ebony seed oil fatty acid reacts with a sphingosine compound, the condensing agent is DCC, and the catalyst is DMAP.
Further, the molar ratio of the sandalwood seed oil fatty acid to the sphingosine compound to the DCC to the DMAP is 1: (1-1.5): (1-2): (0.2-0.5), wherein the solvent for the reaction is at least one of dichloromethane, tetrahydrofuran, ethyl acetate and acetonitrile.
The commercially available sandalwood seed oil is generally in the form of oil and fat, and needs to be hydrolyzed into the sandalwood seed oil fatty acid, and therefore the method further comprises the following steps:
the sandalwood seed oil fat is hydrolyzed by saponification reaction to obtain the sandalwood seed oil fatty acid.
Further, the saponification reaction is hydrolysis of the sandalwood seed oil grease in potassium hydroxide solution.
Further, the mass ratio of the sandalwood seed oil grease to the potassium hydroxide is 1: (1-2).
In a third aspect of the invention, the use of a santalum album seed oil ceramide in a cosmetic, pharmaceutical, dietary or health care product.
Further, the sandalwood seed oil ceramide has at least one of skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, anti-oxidation, collagen synthesis promotion, elastin activity maintenance, and whitening effects.
A composition comprising a santalum album seed oil ceramide, the composition having at least one of skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, anti-oxidant, collagen synthesis promoting, elastin viability maintaining, whitening efficacy.
The composition contains acceptable auxiliary materials, including one or more of solubilizer, antiseptic, antioxidant, pH regulator, penetration enhancer, liposome, humectant, thickener, chelating agent, skin feel regulator, surfactant, emulsifier, essence and pigment; the composition is in the form of cream, emulsion, solution, film, aerosol or spray.
The invention has the following beneficial effects:
the rosewood seed oil fatty acid belongs to naturally-formed fatty acid, the main components are unsaturated fatty acid-oleic acid and linolenic acid, and the rosewood seed oil fatty acid and a sphingosine compound naturally existing in skin are subjected to mild reaction to prepare the rosewood seed oil ceramide, so that the rosewood seed oil ceramide has excellent performance in the aspects of repairing a natural skin barrier, resisting oxidation, resisting aging and the like, and has wide application prospects in the fields of cosmetics, health-care products, biological medicines and the like.
1. Better results compared to ceramide alone. Different ceramides have different effects due to the structural differences, and ceramides with a single structure generally have difficulty in having comprehensive effects. The scheme is based on a bionic thought, natural-source sandalwood seed oil grease or fatty acid is used as a raw material to synthesize the compound ceramide so as to make up the difference of different ceramide effects, and trace fatty acid in the sandalwood seed oil can form trace ceramide, wherein the siemens wood acetylenic acid ceramide and the ceramide are unique ceramide, and play a role in efficacy supplement.
2. Compared with the compounded ceramide, the effect is better. Besides fatty acid (or grease), the sandalwood seed oil is rich in active ingredients such as flavone, polyphenol, vitamins and the like, and the nutrients have the effects of moistening skin, whitening, removing freckles and the like, and the ceramide synthesized by the sandalwood seed oil has a synergistic effect with other active ingredients contained in the sandalwood seed oil, so that the ceramide has a better effect compared with the ceramide compounded according to similar proportions.
3. The cost is lower. The method of the invention can rapidly obtain the composition compounded by various ceramides, the plant-derived sandalwood seed oil or the fatty acid thereof has wide sources, is easy to obtain commercially, has lower cost, is more environment-friendly and economical, is different from the idea of mixing and compounding different single ceramides, has high raw material price of the fatty acid with single component, and needs to separately produce different ceramides and then compound, thereby increasing the preparation cost.
4. The synthesis method is simple. The method can adopt chemical synthesis to realize one-step preparation of various ceramides, and can also use a microbial fermentation method.
Drawings
FIGS. 1 and 2 are bar graphs showing the results of the cell proliferation activity test of example 4;
FIG. 3 is the result of the cell migration ability test of example 5;
FIG. 4 is a bar graph of elastase inhibition of example 6;
FIG. 5 is a bar graph showing the detection of IL-6 factor expression level in anti-inflammatory repair efficacy in example 7;
FIGS. 6 and 7 are bar charts of MMP1 expression levels in the photo-aging test of example 8;
FIG. 8 is a bar graph of DPPH radical scavenging for oxidation resistance test of example 9;
fig. 9 is a bar graph of the whitening activity test melanin content of example 10.
Detailed Description
The invention will be further illustrated with reference to specific examples.
DCC means N, N' -dicyclohexylcarbodiimide and DMAP means 4-dimethylaminopyridine. The silica gel column chromatography uses Qingdao ocean silica gel (particle size 0.040-0.063 mm). Thin Layer Chromatography (TLC) using 60F254 silica gel plates was performed using UV light (254 nm) or iodine.
Example 1
Synthesis of ceramide from Pterocarpus Indicus seed oil fatty acid and phytosphingosine
The first step: 50g of the ebony seed oil grease is dissolved in 60mL of tetrahydrofuran, cooled in an ice bath, 100mL of potassium hydroxide (25 wt%) solution is added dropwise, and the reaction is carried out after the dropwise addition is completed, and the temperature is raised to room temperature until the TLC detection reaction is completed.
Post-treatment: adding dilute hydrochloric acid (3N) to adjust the pH value of the reaction system to 3, adding 150mL of ethyl acetate to extract the water phase, adding 100mL of saturated saline water to wash once, and adding an organic phase to the mixtureAnhydrous Na 2 SO 4 Drying, filtering and concentrating in vacuo to give 41g of a sandalwood seed oil fatty acid.
And a second step of: the sandalwood seed oil fatty acid (50 mmol, calculated as the main component fatty acid), DCC (65 mmol), DMAP (15 mmol) were added to a 250mL round bottom flask, and 100mL dichloromethane was added, followed by stirring at room temperature for 1 hour, and then phytosphingosine (65 mmol) was added to the reaction system, followed by stirring at room temperature until TLC detection was completed.
Post-treatment: filtering the reaction solution to remove solids, collecting filtrate, respectively adding a saturated solution of sodium bicarbonate, washing with 1N diluted hydrochloric acid and saturated saline, separating an organic layer, drying, filtering, concentrating in vacuum, washing with a solvent to obtain the sandalwood seed oil ceramide, and analyzing the product by HPLC (high performance liquid chromatography) under the condition of HPLC chromatography: using an shimadzu high performance liquid chromatograph (LC-2030 c 3d Plus), column temperature with Innoval ODS-2.6x250 mm,5 μm column: 30 ℃, sample injection volume: 10 μl, flow rate: 1.0mL/min, evaporation temperature: 40 ℃, carrier gas flow rate: 2.5L/min, mobile phase: 100% methanol.
The retention time of each component HPLC was: linolenic acid-phytosphingosine ceramide 8.5min, linoleic acid-phytosphingosine ceramide 9.5min, oleic acid-phytosphingosine ceramide 11.4min, stearic acid-phytosphingosine ceramide 13.9min, siemens alkynoic acid-phytosphingosine ceramide 16.3min, and ceramide 22.2min.
The obtained products are analyzed by high performance liquid chromatography, and the contents of oleic acid-phytosphingosine ceramide, linolenic acid-phytosphingosine ceramide, stearic acid-phytosphingosine ceramide, linoleic acid-phytosphingosine ceramide, siemens acid-phytosphingosine ceramide and nervonic acid-phytosphingosine ceramide are 54%, 23%, 6%, 1%, 7% and the balance of other components in sequence, and the contents are less.
Example 2
Synthesis of ceramide from Pterocarpus Indicus seed oil fatty acid and sphingosine
The first step: 50g of the ebony seed oil grease is dissolved in 60mL of tetrahydrofuran, cooled in an ice bath, 100mL of potassium hydroxide (25 wt%) solution is added dropwise, and the reaction is carried out after the dropwise addition is completed, and the temperature is raised to room temperature until the TLC detection reaction is completed.
Post-treatment: adding dilute hydrochloric acid (3N) to adjust the pH value of the reaction system to 3, adding 150mL of ethyl acetate to extract a water phase, adding 100mL of saturated saline water for washing once, and adding anhydrous Na into an organic phase 2 SO 4 Drying, filtration and concentration in vacuo gave 41.3g of a sandalwood seed oil fatty acid.
And a second step of: the sandalwood seed oil fatty acid (50 mmol, based on the main component fatty acid), DCC (60 mmol), DMAP (20 mmol) were added to a 250mL round bottom flask, and 100mL dichloromethane was added, followed by stirring at room temperature for 1 hour, followed by adding sphingosine (55 mmol) to the reaction system, stirring at room temperature, until TLC detection was completed.
Post-treatment: filtering the reaction solution to remove solids, collecting filtrate, respectively adding a saturated solution of sodium bicarbonate, washing with 1N diluted hydrochloric acid and saturated saline, separating an organic layer, drying, filtering, concentrating in vacuum, washing with a solvent to obtain the sandalwood seed oil ceramide, and analyzing the product by HPLC (high performance liquid chromatography) under the condition of HPLC chromatography: using an shimadzu high performance liquid chromatograph (LC-2030 c 3d Plus), column temperature with Innoval ODS-2.6x250 mm,5 μm column: 30 ℃, sample injection volume: 10 μl, flow rate: 1.0mL/min, evaporation temperature: 40 ℃, carrier gas flow rate: 2.5L/min, mobile phase: 100% methanol.
The retention time of each component HPLC was: linolenic acid-sphingosine ceramide 7.9min, oleic acid-sphingosine ceramide 10.2min, palmitic acid-sphingosine ceramide 10.5min, stearic acid-sphingosine ceramide 13.6min, and ceramide 21.5min.
The obtained product is analyzed by high performance liquid chromatography, and the content of oleic acid-sphingosine ceramide, linolenic acid-sphingosine ceramide, stearic acid-sphingosine ceramide, palmitic acid-sphingosine ceramide and nervonic acid-sphingosine ceramide is 65%, 16%, 4%, 1%, 10% and the rest is other components, and the content is less.
Example 3
Synthesis of ceramide from Pterocarpus Indicus seed oil fatty acid and sphinganine
The first step: 50g of the ebony seed oil grease is dissolved in 60mL of tetrahydrofuran, cooled in an ice bath, 100mL of potassium hydroxide (25 wt%) solution is added dropwise, and the reaction is carried out after the dropwise addition is completed, and the temperature is raised to room temperature until the TLC detection reaction is completed.
Post-treatment: adding dilute hydrochloric acid (3N) to adjust the pH value of the reaction system to 3, adding 150mL of ethyl acetate to extract a water phase, adding 100mL of saturated saline water for washing once, and adding anhydrous Na into an organic phase 2 SO 4 Drying, filtration and concentration in vacuo gave 41.5g of a sandalwood seed oil fatty acid.
And a second step of: the sandalwood seed oil fatty acid (50 mmol, based on the main component fatty acid), DCC (70 mmol), DMAP (10 mmol) were added to a 250mL round bottom flask, and 100mL dichloromethane was added, followed by stirring at room temperature for 1 hour, followed by adding dihydrosphingosine (60 mmol) to the reaction system, stirring at room temperature, until TLC detection was completed.
Post-treatment: filtering the reaction solution to remove solids, collecting filtrate, respectively adding a saturated solution of sodium bicarbonate, washing with 1N diluted hydrochloric acid and saturated saline, separating an organic layer, drying, filtering, concentrating in vacuum, washing with a solvent to obtain the sandalwood seed oil ceramide, and analyzing the product by HPLC (high performance liquid chromatography) under the condition of HPLC chromatography: using an shimadzu high performance liquid chromatograph (LC-2030 c 3d Plus), column temperature with Innoval ODS-2.6x250 mm,5 μm column: 30 ℃, sample injection volume: 10 μl, flow rate: 1.0mL/min, evaporation temperature: 40 ℃, carrier gas flow rate: 2.5L/min, mobile phase: 100% methanol.
The retention time of each component HPLC was: linolenic acid-dihydrosphingoceramide 8.3min, oleic acid-dihydrosphingoceramide 11.1min, stearic acid-dihydrosphingoceramide 13.5min, siemens acid-dihydrosphingoceramide 17.2min, behenic acid-dihydrosphingoceramide 21.8min, and ceramide 24.1min.
The obtained product is analyzed by high performance liquid chromatography, the content of oleic acid-dihydrosphingosine ceramide, linolenic acid-dihydrosphingosine ceramide, stearic acid-dihydrosphingosine ceramide, behenic acid-dihydrosphingosine ceramide, siemens acid-dihydrosphingosine ceramide and nervonic acid-dihydrosphingosine ceramide is sequentially 50%, 31%, 3%, 2%, 8% and 4%, and the rest is other components, and the content is less.
Example 4
MTT method for detecting proliferation activity of compound on cell
HaCaT cells were grown at 1X 10 4 The density of individuals/wells was seeded in 96-well plates and the incubator was overnight. After 24h, the supernatant was discarded, 100. Mu.L of medium containing samples of different concentrations (product of example 1) was added, incubation was continued for 24h, medium was removed, 100. Mu.L of thiazole blue (MTT) was added to each well, absorbance at 450nm was measured, and cell viability = A was calculated Drug delivery hole /A Blank hole ×100％。
As shown in figure 1, the ebony seed oil ceramide has a promoting effect on cell viability, and the cell viability is 132.61%, 124.80%, 118.90%, 123.14%, 117.91%, 129.79%, 130.79%, 138.51% and 131.20% respectively at the concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500 and 1000mg/L, the effective concentration is as low as 4mg/L, the safe concentration is 1000mg/L, the concentration gradient is relatively stable, the obvious effect of promoting cell proliferation is shown, and the tissue repair capability is good.
The proliferation activity of ceramide 2 on cells was measured in the same manner, and as a result, as shown in FIG. 2, cell viability was 61.49%, 60.03%, 55.41%, 54.64%, 53.37%, 46.95%, 44.05%, 40.35%, 39.42% at concentrations of 3.90625, 7.8125, 15.625, 31.25, 62.5, 125, 250, 500, 1000mg/L, respectively, which had an inhibitory effect on cell proliferation and a tissue repair potential inferior to that of sandalwood seed oil ceramide.
Example 5
Assessment of skin barrier repair by cell migration
Principle of: when the cells grow to be fused into a single-layer state, a scratch tool is manufactured on the fused single-layer cells, the cells in the blank area are removed by mechanical force, the migration condition of the cells to the cell-free area is observed through a period of culture, and the migration capability of the cells is reflected by measuring the migration distance of the cells.
The operation steps are as follows:
1. the culture plate is streaked. Firstly, a Marker pen is used for uniformly scribing transverse lines by comparing with a straight ruler, and the transverse lines are crossed through the through holes at intervals of about 0.5 cm to 1cm, and each hole at least passes through 5 lines, so that attention lines are not too thick when scribing.
2. And (5) paving cells. About 5X 10 is added to the well 5 Individual cells (the number of different cells is different, and the cell growth speed is regulated), and the inoculation principle is that the fusion rate reaches 100% after overnight.
3. Cell streaking. The next day the tip is used to scratch the cell layer along the line marked on the back of the plate on the first day, perpendicular to the cell plane (the same tip is preferably used between the different wells).
4. Washing cells. After the streaking was completed, cells were washed 3 times with sterile PBS, cells that did not adhere to the wall, i.e., streaked cells at streaking, and the gap left after streaking was clearly visible, followed by replacement of fresh serum-free medium.
5. And (5) culturing and observing the cells. After the sample (product of example 1, ceramide 3B) was diluted with the medium (product of example 1 at 5mg/L, ceramide 3B at 100 mg/L), the cells were placed in a cell culture dish at 37℃and 5wt% CO 2 Incubator culture, after 24 hours, cells were removed, observed with a microscope and the width of scratches was measured, and photographed, and the healing rate was calculated using Image J software.
The results are shown in fig. 3, and the scratch width of the experimental group is narrower than that of the solvent control group, which indicates that the sandalwood seed oil ceramide has better tissue healing capacity. The solvent control group had a healing rate of 29.58% after 24 hours, the sandalwood seed oil ceramide had a healing rate of 94.26% after 24 hours, and ceramide 3B had a healing rate of 59.32% after 24 hours. The compound obviously improves the cell healing rate, has good skin tissue repair activity and has better effect than ceramide 3B.
Example 6
Elastase inhibition experiment tests anti-aging effect
Elastase inhibition method: 2mg/mL elastase solution (product of example 1) is taken, samples with different concentrations (2 mL) are added, vortex mixing is carried out fully, shaking is carried out for 20min at 37 ℃ by a 400r/min shaking table, 5mL of 0.5mol/L phosphate buffer solution with pH of 6.0 is added immediately, vortex mixing is carried out, a proper amount of mixed solution is taken into a 2mL centrifuge tube, centrifugation is carried out for 10min at 9 391×g, 200 mu L of supernatant is sucked into a 96-well plate precisely, absorbance is measured by an enzyme-labeled instrument at a wavelength of 495nm, and spectrum scanning at 400-800 nm is carried out simultaneously.
The substrate enzyme adding solution is used as a blank control group, the substrate enzyme adding and sample solution is used as an enzyme inhibition group, and the substrate enzyme adding and sample solution is used as a background. Each group is provided with 3 multiple holes. Inhibition ratio (%) = [1- (An-An ')/(A0-A0') ] ×100%, where A0 is absorbance with no enzyme added to the sample, A0 'is absorbance with no enzyme added to the substrate and no sample added to the enzyme, an is absorbance with only sample solution, an' is absorbance with no enzyme added to the sample. When An ' > An, the effect is expressed as acceleration, and the acceleration rate (%) = [1- (An ' -An)/(A0-A0 ') ] ×100%.
As shown in FIG. 4, the sandalwood seed oil ceramide has a good inhibitory effect on elastase at various concentrations, specifically, the inhibition rate of elastase at a concentration of 0.25g/L is 11.47%, the inhibition rate of elastase at a concentration of 0.5g/L is 18.33%, the inhibition rate of elastase at a concentration of 1.0g/L is 23.60%, and the inhibition rate of elastase at a concentration of 2.0g/L is 16.67%.
Example 7
LPS induced cell method for detecting anti-inflammatory repair efficacy
B16 mouse melanoma cells were grown at a density of 1X 10 4 The cells/wells were seeded in 96-well plates, placed in an incubator overnight, the supernatant was discarded after 24 hours, 100. Mu.L of samples of different concentrations diluted with DMEM medium (product of example 1) were added, the negative control group was DMEM medium without samples, 3 wells per group, and mixed with CO at 5 wt.% 2 Incubate at 37 ℃. Lipopolysaccharide model group and experimental group were added with 10 μg/mL LPS and incubated together for 24h 2h after dosing. After the reaction, 50. Mu.L of the cell supernatant was collected, and the intracellular IL-6 gene expression was detected using an IL-6ELISA kit.
The results are shown in FIG. 5, where IL-6 levels were 10.16 times the basal levels at a working concentration of 10. Mu.g/mL of LPS stimulation. Under the action of the ebony seed oil ceramide with the concentration of 50mg/L, 100mg/L, 200mg/L and 400mg/L respectively, the IL-6 factor level is obviously reduced and is 0.99 times, 0.74 times, 0.53 times and 0.27 times of that of an LPS model group respectively, and the ebony seed oil ceramide is dose-dependent, which proves that the ebony seed oil ceramide has good anti-inflammatory effect and can promote the repair of inflammatory damaged skin.
Example 8
Photo aging resistance test
MMP1 is also called interstitial collagenase and matrix metalloproteinase, belongs to matrix metalloproteinase family, and its main acting substrate is fibrous collagen, which can degrade collagen fiber and gelatin in extracellular matrix and change microenvironment of cells. MMP1 plays an important role in elastin, inhibiting MMP1 can improve the synthesis of fibroblast collagen and elastin, and reducing MMP activity can increase the collagen synthesis speed.
HaCaT cells were grown at 1X 10 5 The density of individuals/wells was seeded in 96-well plates and the incubator was overnight. After 24h, the supernatant was discarded, 100. Mu.L of medium containing samples of different concentrations (product of example 1) was added, no samples were added to the model group, the negative control group was DMEM medium without samples, 3 wells per group, and the mass fraction was 5% CO 2 After incubation for 2h at 37℃either UVA or UVB ultraviolet radiation is irradiated. The distance between the ultraviolet radiation source and the cells was 15cm, and the UVA intensity was 200mJ/cm 2 The irradiation time was 2 hours, and the UVB intensity was 50mJ/cm 2 The irradiation time was 1h. After the end of irradiation, incubation was continued for 12h in the incubator. Intracellular MMP-1 gene expression was detected using an MMP-1ELISA kit. Inhibition = 1- (experimental group MMP1 expression level/model group MMP1 expression level) ×100%.
As shown in fig. 6 and 7, the expression level of MMP1 in the negative control group was 1, the expression level in the model group was 1.90, and the inhibition ratio of MMP1 expression in the model group was 29%, 41% and 64% at the concentrations of 125, 250 and 400mg/L in the sandalwood seed oil ceramide; for UVB, the MMP1 expression level of the negative control group was 1, the expression level of the model group was 2.33, and the inhibition rate of the sea sandalwood seed oil ceramide at the concentration of 125, 250 and 400mg/L was 38%, 49% and 62% relative to the MMP1 expression of the model group.
After UVA uv radiation, keratinocytes promote elevated expression of MMP1 by fibroblasts, thereby causing degradation of the extracellular matrix of the skin and collagen of the skin, leading to photoaging of the skin. The results show that the sandalwood seed oil ceramide can inhibit the fibroblast from producing MMP1 caused by ultraviolet radiation, and has a certain effect on preventing skin photoaging.
Example 9
DPPH free radical scavenging detection of antioxidant performance
DPPH is 1, 1-diphenyl-2-trinitrophenylhydrazine, and can be used for antioxidant experiments. Samples (product of example 1) at corresponding concentrations (50, 100, 200, 400, 800 mg/L) were mixed with 0.1mol/L DPPH, absolute ethanol solution at a ratio of 1:1, and DPPH and absolute ethyl alcohol 1:1, and the absorbance at 517 nm. The absorbance of the sample and the reaction solution of DPPH was designated as A1, the absorbance of the sample and the reaction solution of absolute ethyl alcohol was designated as A2, the absorbance of the reaction solution of DPPH and absolute ethyl alcohol was designated as A3, and the clearance rate of DPPH of the sample was = [1- (A1-A2)/A3 ]. Times.100%.
As a result, as shown in FIG. 8, the DPPH radical scavengers at concentrations of 50, 100, 200, 400 and 800mg/L were 4.43%, 9.43%, 17.04%, 19.58% and 20.69%, respectively, and excellent antioxidant effects were exhibited.
Example 10
Whitening Activity test
Taking B16 cells in exponential growth phase, digesting with trypsin-EDTA with mass fraction of 0.25%, blowing uniformly, and mixing the cells according to 3×10 5 Density of individual/well was seeded in 12-well plates. At 37 ℃, the mass fraction of CO is 5 percent 2 Incubated overnight in the environment. Removing supernatant, adding culture solution containing samples with different mass concentrations (product of example 1), incubating with RPMI-1640 culture medium without sample as blank group, incubating with DMEM culture medium as mould group, and incubating with 3 compound holes in each group at mass fraction of 5% CO 2 Incubation was carried out for 24h at 37 ℃. The medium in the well plate was discarded, and after washing with Phosphate Buffer (PBS) one to two times,1mL of NaOH solution (1 mol/L) containing 10% DMSO in mass fraction was added to lyse the cells, and the cells were left to stand at 80℃or 100℃for 2 hours until the cells were completely dissolved. The absorbance was measured at 405nm in a microplate reader. The melanin inhibition rate=1- (OD value per well/OD value of model group) ×100% was calculated.
As shown in fig. 9, the blank group had a melanin content of 1, the melanin expression of the model group of 1.51, and the melanin inhibition rates of the sandalwood seed oil ceramide of 3.27%, 14.73%, 14.91%, 23.37% and 22.84% at concentrations of 10, 20, 40, 80, and 100mg/L, respectively, and exhibited a certain whitening effect.
The foregoing is merely illustrative embodiments of the present invention, and the present invention is not limited thereto, and any changes or substitutions that may be easily contemplated by those skilled in the art within the scope of the present invention should be included in the scope of the present invention. Therefore, the protection scope of the present invention should be subject to the protection scope of the claims.

Claims (10)

1. The sandalwood seed oil ceramide is obtained by reacting a sandalwood seed oil fatty acid with a sphingosine compound, wherein the sphingosine compound is selected from sphingosine, phytosphingosine and dihydrosphingosine.
2. The rosewood seed oil ceramide of claim 1, wherein the rosewood seed oil fatty acid is hydrolyzed from rosewood seed oil.
3. The rosewood seed oil ceramide of claim 1 or 2, wherein the rosewood seed oil fatty acid contains 50 to 75wt% oleic acid, 15 to 40wt% linolenic acid, 0.5 to 10wt% stearic acid.
4. The composition of the sandalwood seed oil ceramide comprises: oleic acid ceramide, linolenic acid ceramide, stearic acid ceramide.
5. The sandalwood seed oil ceramide of claim 4, comprising the composition of: 50 to 75 weight percent of oleic acid ceramide, 15 to 40 weight percent of linolenic acid ceramide and 0.5 to 10 weight percent of stearic acid ceramide.
6. The sandalwood seed oil ceramide of claim 4 or 5, further comprising: 0 to 15 weight percent of siemens acid ceramide, 0 to 15 weight percent of nervonic acid ceramide, 0 to 2 weight percent of behenic acid ceramide, 0 to 1 weight percent of palmitic acid ceramide and 0 to 1 weight percent of linoleic acid ceramide.
7. The synthesis method of the sandalwood seed oil ceramide according to any one of claims 1 to 6, comprising the following steps:
under the conditions of a condensing agent and a catalyst, the ebony seed oil fatty acid reacts with a sphingosine compound, the condensing agent is DCC, and the catalyst is DMAP;
the molar ratio of the pterocarpus santalinus seed oil fatty acid to the sphingosine compound to the DCC to the DMAP is 1: (1-1.5): (1-2): (0.2-0.5), wherein the solvent for the reaction is at least one of dichloromethane, tetrahydrofuran, ethyl acetate and acetonitrile.
8. Use of a sandalwood seed oil ceramide of any one of claims 1-6 in cosmetics, pharmaceuticals, dietary or health care products.
9. The use according to claim 8, wherein the sandalwood seed oil ceramide has at least one of skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, antioxidant, promotion of collagen synthesis, maintenance of elastin activity, whitening efficacy.
10. A composition comprising the sandalwood seed oil ceramide of any one of claims 1-6, which has at least one of skin barrier repair, tissue healing, anti-aging, anti-inflammatory, anti-photoaging, antioxidant, promotion of collagen synthesis, maintenance of elastin activity, whitening efficacy.
CN202310051745.XA 2022-11-25 2023-02-02 Pterocarpus santalinus seed oil ceramide and synthesis method and application thereof Pending CN117326967A (en)

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