Sphingosine supramolecular body as well as preparation method and application thereof

Abstract

The invention provides a sphingosine supramolecular body and a preparation method and application thereof, and belongs to the technical field of cosmetics, and the sphingosine supramolecular body is prepared by dissolving hydroxy acid and sphingosine in water according to a molar ratio of 1: (0.5-5). According to the sphingosine supramolecular body provided by the invention, the supramolecular body is formed by self-assembly through the strong hydrogen-bond interaction between the hydroxy acid and sphingosine molecules, so that the ionic strength of the hydroxy acid can be effectively reduced, and the problem of poor water solubility of sphingosine can be solved.

Description

Technical Field

[0001] The invention belongs to the technical field of cosmetics, and in particular relates to a sphingosine supramolecular body and a preparation method and application thereof. Background Art

[0002] Sphingosine is an important bioactive molecule that is widely present in human organs and tissues. Sphingosine can regulate intracellular signaling by binding to proteins, ligands or other small molecules, thereby affecting cellular physiological processes such as cell growth, differentiation, autophagic processes and development. After being released from complex sphingolipids, sphingosine is mainly reacylated by ceramide synthase or phosphorylated by sphingosine kinase to produce 1-phosphate sphingosine, which induces cell cycle arrest and apoptosis by regulating protein kinases and other signaling pathways. In addition to its function in cell signaling, sphingosine also has broad-spectrum antibacterial properties. Sphingosine has been reported to have antibacterial activity against Gram-positive and Gram-negative bacteria, enveloped viruses and fungi. The role of sphingosine as an antibacterial agent is important in tissues such as the skin, respiratory epithelium and oral cavity. Sphingosine is insoluble in water. During the application process, it was found that a higher concentration of ethanol solution was required to form the required aqueous solution. Due to the hydrophobic alkyl group of the long carbon chain at the tail of sphingosine, the solution precipitated and formed floating objects.

[0003] Supramolecular usually refers to two or more molecules, which are combined by secondary bonds between molecules to form an ordered aggregate. Supramolecular is a combination of molecules, and the binding force is often non-covalent bond force, which belongs to weak interaction, including van der Waals force, hydrogen bond force, π-π stacking effect, electrostatic effect and hydrophobic effect. Supramolecular can be spherical, rod-shaped, sheet-shaped and other shapes, and its size is in the range of nanometers and micrometers. Supramolecular technology can be used as supramolecular raw materials and supramolecular solvents in cosmetic formulation applications. As a raw material, supramolecular technology can not only improve the compatibility of some insoluble raw materials, but also enhance the efficacy and transdermal properties; as a supramolecular solvent, supramolecular technology can not only extract insoluble active ingredients, but also has the possibility of enhancing the efficacy of plant extracts. Therefore, supramolecular technology is gradually shining in the field of biomedicine and cosmetics. Summary of the invention

[0004] In view of this, the object of the present invention is to provide a sphingosine supramolecular body and a preparation method and application thereof, so as to overcome the problem of poor water solubility of sphingosine in the prior art.

[0005] The invention provides a sphingosine supramolecular body, which is prepared by dissolving hydroxy acid and sphingosine in water at a molar ratio of 1: (0.5-5).

[0006] Preferably, the molar ratio of the hydroxy acid to sphingosine is 1:(1-2), and the sphingosine is phytosphingosine, sphingosine and / or dihydrosphingosine. The hydroxy acid is sphingosine, lactobionic acid, gluconic acid, maltobionic acid, mandelic acid, salicylic acid or glycolic acid.

[0007] Preferably, the particle size of the sphingosine supramolecular aqueous solution is 10 to 400 nm.

[0008] Preferably, the mass concentration of the sphingosine supramolecular body in the aqueous solution is 0.1-20%, and the pH value of the sphingosine supramolecular body aqueous solution is 4.5-7.

[0009] The present invention provides a method for preparing the sphingosine supramolecular body, comprising the following steps:

[0010] 1) dissolving hydroxy acid and sphingosine in water to obtain a sphingosine supramolecular aqueous solution;

[0011] 2) Drying the sphingosine supramolecular aqueous solution to obtain sphingosine supramolecular sialic acid.

[0012] Preferably, the dissolving temperature in step 1) is 25 to 70° C., and the dissolving time is 5 to 30 minutes.

[0013] Preferably, the drying in step 2) is spray drying or freeze drying.

[0014] Preferably, the inlet air temperature of the spray drying is 55-60°C, and the outlet air temperature of the spray drying is 30-40°C.

[0015] The invention also provides application of the sphingosine supramolecular body in cosmetics.

[0016] Compared with the prior art, the present invention has the following beneficial effects: the sphingosine supramolecular provided by the present invention is prepared by dissolving hydroxy acid and sphingosine in water at a molar ratio of 1: (0.5-5), and the preparation method is simple, and the supramolecular structure can be formed only by scientific proportioning and temperature control, and then obtained by drying. The sphingosine supramolecular provided by the present invention self-assembles to form a supramolecular body through the electrostatic interaction and hydrogen bonding between hydroxy acid and sphingosine molecules, which can effectively reduce the ionic strength of hydroxy acid and solve the problem of poor water solubility of sphingosine. The sphingosine supramolecular provided by the present invention has the characteristics of good water solubility and low ionic strength. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 It is the transparency of phytosphingosine supramolecular body at 25℃ and 50℃. DETAILED DESCRIPTION

[0018] The invention provides a sphingosine supramolecular body, which is prepared by dissolving hydroxy acid and sphingosine in water at a molar ratio of 1: (0.5-5).

[0019] In the present invention, the molar ratio of the hydroxy acid to sphingosine is preferably 1: (1-2), and the sphingosine is preferably phytosphingosine (purchased from Chongqing Zhihe Biomedicine Co., Ltd.), sphingosine (purchased from Evonik Specialty Chemicals (Shanghai) Co., Ltd.) and / or dihydrosphingosine (purchased from Evonik Specialty Chemicals (Shanghai) Co., Ltd.). In the present invention, the hydroxy acid is preferably sphingosine, lactobionic acid, gluconic acid, maltobionic acid, mandelic acid, salicylic acid or glycolic acid. In the present invention, the hydroxy acid and sphingosine are dissolved in water to obtain a sphingosine supramolecular aqueous solution, and the particle size of the sphingosine supramolecular aqueous solution is preferably 10-400nm, and more preferably 100-300nm. In the present invention, the mass concentration of the sphingosine supramolecular in the aqueous solution is preferably 0.1%-20%, and more preferably 8%-16%. In the present invention, the pH value of the sphingosine supramolecular aqueous solution is preferably 4.5-7, and more preferably 5-6.

[0020] The present invention provides a method for preparing the supramolecular body, comprising the following steps: 1) dissolving hydroxy acid and sphingosine in water to obtain a sphingosine supramolecular body aqueous solution; 2) drying the sphingosine supramolecular body aqueous solution to obtain sphingosine supramolecular body.

[0021] In the present invention, hydroxy acid and sphingosine are dissolved in water to obtain a sphingosine supramolecular aqueous solution; the dissolution temperature is preferably 25 to 70°C, more preferably 40 to 65°C, and more preferably 50 to 60°C; in the present invention, the dissolution time is preferably 5 to 30 minutes. In the present invention, the dissolution is conventional stirring dissolution.

[0022] After obtaining the sphingosine supramolecular aqueous solution, the present invention dries the sphingosine supramolecular aqueous solution to obtain sphingosine guanidine supramolecular body. In the present invention, the drying is preferably spray drying or freeze drying; when the drying is spray drying, the inlet air temperature of the spray drying is preferably 55-60°C, and the outlet air temperature of the spray drying is preferably 30-40°C. After the drying, the present invention obtains a powdered sphingosine supramolecular body.

[0023] The present invention also provides the use of amino alcohol supramolecular body in cosmetics. In the present invention, the sphingosine supramolecular body is used as an active ingredient in cosmetics, and has multiple functions such as moisturizing, anti-aging, whitening and lightening. The present invention has no special restrictions on the type of the cosmetics, and lotions, emulsions, essences, creams, masks, etc. are all acceptable.

[0024] The technical solutions provided by the present invention are described in detail below in conjunction with the embodiments, but they should not be construed as limiting the protection scope of the present invention.

[0025] Example 1

[0026] Weigh 9 g of sialic acid and 9 g of phytosphingosine respectively and dissolve them in 100 ml of water at 60°C. Stir magnetically at 200 rpm for 30 minutes until the solution becomes transparent. The pH value is measured to be 4.89. Use a dry air system for low-temperature spray drying with an inlet air temperature of 60°C and an outlet air temperature of 35°C to obtain powdered sialic acid and phytosphingosine supramolecular bodies.

[0027] Example 2

[0028] Weigh 6 g of sialic acid and 9 g of phytosphingosine respectively and dissolve them in 100 ml of water at 50°C. Stir magnetically at 300 rpm for 20 min until the solution becomes translucent. The pH value is measured to be 5.18. Use a dry air system for low-temperature spray drying with an inlet air temperature of 60°C and an outlet air temperature of 35°C to obtain powdered sialic acid and phytosphingosine supramolecular bodies.

[0029] Example 3

[0030] Weigh 4.5 g of sialic acid and 9 g of phytosphingosine respectively and dissolve them in 100 ml of water at 60° C. Stir magnetically at 100 rpm for 30 min until the solution becomes translucent. The pH value is 5.24. Freeze-dry for 24 h to obtain powdered sialic acid and phytosphingosine supramolecular bodies.

[0031] Example 4

[0032] Weigh 3g of sialic acid and 9g of phytosphingosine respectively and dissolve them in 100ml of water at 50°C. Stir magnetically at 200rpm for 30min until the solution becomes translucent. The pH value is measured to be 5.46. Use a dry air system to spray dry at a low temperature with an inlet air temperature of 60°C and an outlet air temperature of 35°C to obtain powdered sialic acid and phytosphingosine supramolecular bodies.

[0033] Example 5

[0034] Weigh 5 g of sialic acid and 5 g of sphingosine respectively and dissolve them in 100 ml of water at 30°C. Stir magnetically at 300 rpm for 15 min until the solution becomes transparent. The pH value is measured to be 5.15. Use a dry air system for low-temperature spray drying with an inlet air temperature of 60°C and an outlet air temperature of 35°C to obtain powdered sialic acid sphingosine supramolecular bodies.

[0035] Example 6

[0036] Weigh 5 g of sialic acid and 5 g of dihydrosphingosine respectively and dissolve them in 100 ml of water at 40°C. Stir magnetically at 200 rpm for 20 minutes until the solution becomes transparent. The pH value is measured to be 5.21. Use a dry air system for low-temperature spray drying with an inlet air temperature of 60°C and an outlet air temperature of 35°C to obtain a powdered sialic acid dihydrosphingosine supramolecular body.

[0037] Example 7

[0038] Weigh 2.5 g of lactobionic acid and 2.1 g of dihydrosphingosine respectively, dissolve in 100 ml of water at 40°C, stir magnetically at 200 rpm for 10 min until the solution becomes transparent, measure the pH value to be 4.96, freeze at -20°C for 24 h, and then freeze-dry at a vacuum degree of less than 90 Pa and a drying temperature of 40°C for 24 h to obtain a powdered lactobionic acid dihydrosphingosine supramolecular body.

[0039] Example 8

[0040] Weigh 2.5 g of maltobionic acid and 2.6 g of sphingosine respectively, dissolve in 100 ml of water at 30°C, stir magnetically at 150 rpm for 20 min until the solution becomes transparent, measure the pH value to be 5.09, freeze at -20°C for 24 h, and then freeze-dry at a vacuum degree of less than 90 Pa and a drying temperature of 40°C for 24 h to obtain a powdered maltobionic acid sphingosine supramolecular body.

[0041] Experimental Example 1

[0042] Take 0.1g of sialic acid and 0 (serial number 1-1), 0.1g (serial number 1-2), 0.12g (serial number 1-3), 0.14g (serial number 1-4), 0.16g (serial number 1-5), and 0.2g (serial number 1-6) of phytosphingosine and dissolve them in 100ml of water at 50°C to form a uniform solution.

[0043] Take 0.1g of bird's nest acid and add it into 100ml of water. Adjust the pH to 5.0 with sodium hydroxide to prepare a bird's nest acid aqueous solution with a pH of 5.0 for testing (serial number 1-7).

[0044] Take 0.1 g of phytosphingosine and disperse it in 100 ml of water. Heat and dissolve it at 50°C for 1 hour to form a phytosphingosine dispersion for testing (serial number 1-8).

[0045] Finally, the pH value and ionic strength of the above-mentioned tested solutions were uniformly measured, and the results are shown in Table 1. With the addition of phytosphingosine, the pH value of the scutellaria aviculare solution increased, and the conductivity gradually decreased. When the amount of phytosphingosine exceeded 0.14 g, the pH increase reached a plateau period, increasing slowly, and the conductivity decrease also reached a slow plateau period, decreasing slowly. Although samples 1-3 and 1-7 have similar pH values, the conductivity of the sample with the addition of phytosphingosine is about 100 μs / cm lower than that of the sample with the addition of sodium hydroxide, indicating that there is a strong hydrogen bond between phytosphingosine and scutellaria aviculare that is different from the ionic effect of conventional acid-base neutralization.

[0046] Table 1 pH and conductivity of supramolecular bodies

[0047]

[0048]

[0049] Experimental Example 2

[0050] Effect of temperature on supramolecular bodies: The tested solutions 1-2, 1-3, 1-4, 1-5, 1-6 and 1-8 samples in Experimental Example 1 were kept at a constant temperature of 25°C and 50°C for 6 hours, their appearance was photographed and samples were diluted 10 times, and their particle size was tested with a laser particle size analyzer. The results are shown in Table 2. It can be found that the particle size of pure phytosphingosine exceeds 5000nm, while the particle size of the supramolecular body is about 200nm. The temperature has little effect on the particle size of the sylvian acid phytosphingosine supramolecular body, indicating that the sylvian acid phytosphingosine self-assembles to form a relatively stable supramolecular body. Figure 1 At 50°C, with the increase of phytosphingosine content, bird's nest acid and phytosphingosine formed a transparent supramolecular body. When the content of phytosphingosine reached 2 times of the content of bird's nest acid, the molar ratio between them was close to 1:2. Although the appearance was semi-transparent, the particle size did not change significantly after dilution by 10 times. At 25°C, the transparency of the supramolecular body changed, but the particle size did not change much.

[0051] Table 2 Particle size of supramolecular bodies

[0052]

[0053] It can be seen from the above embodiments and experimental examples that the sphingosine supramolecular body provided by the present invention self-assembles to form a supramolecular body through the electrostatic interaction and hydrogen bonding between hydroxy acid and sphingosine molecules, which can not only effectively reduce the ionic strength of hydroxy acid, but also solve the problem of poor water solubility of sphingosine; and has broad application prospects.

[0054] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the scope of protection of the present invention.

Claims

1. A sphingosine supramolecular body, characterized in that: The product is prepared by dissolving hydroxy acid and sphingosine in water at a molar ratio of 1: (0.5-5).

2. The sphingosine supramolecular body according to claim 1, characterized in that: The molar ratio of the hydroxy acid to sphingosine is 1:(1-2), the sphingosine is phytosphingosine, sphingosine and / or dihydrosphingosine; the hydroxy acid includes sphingolic acid, lactobionic acid, gluconic acid, maltobionic acid, mandelic acid, salicylic acid or glycolic acid.

3. The sphingosine supramolecular body according to claim 1 or 2, characterized in that: The particle size of the sphingosine supramolecular aqueous solution is 10 to 400 nm.

4. The sphingosine supramolecular body according to claim 3, characterized in that: The mass concentration of the sphingosine supramolecular body in the aqueous solution is 0.1% to 20%.

5. The sphingosine supramolecular body according to claim 3, characterized in that: The pH value of the sphingosine supramolecular aqueous solution is 4.5-7.

6. The method for preparing a sphingosine supramolecular body according to any one of claims 1 to 5, characterized in that: The following steps are involved: 1) dissolving hydroxy acid and sphingosine in water to obtain a sphingosine supramolecular aqueous solution; 2) Drying the sphingosine supramolecular aqueous solution to obtain sphingosine supramolecular bodies.

7. The preparation method according to claim 6, characterized in that: The dissolution temperature of step 1) is 25-70° C. and the dissolution time is 5-30 min.

8. The preparation method according to claim 6, characterized in that: Step 2) The drying is spray drying or freeze drying.

9. The preparation method according to claim 6, characterized in that: The inlet air temperature of the spray drying is 55-60°C, and the outlet air temperature of the spray drying is 30-40°C.

10. Use of the sphingosine supramolecular body according to any one of claims 1 to 5 or the sphingosine supramolecular body prepared by the preparation method according to any one of claims 6 to 9 in cosmetics.

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