CN114805137A - Compound, oat bran extract and application of oat bran extract in preparation of product with antioxidant or anti-inflammatory effects - Google Patents
Compound, oat bran extract and application of oat bran extract in preparation of product with antioxidant or anti-inflammatory effects Download PDFInfo
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- CN114805137A CN114805137A CN202210512741.2A CN202210512741A CN114805137A CN 114805137 A CN114805137 A CN 114805137A CN 202210512741 A CN202210512741 A CN 202210512741A CN 114805137 A CN114805137 A CN 114805137A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 14
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 14
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 24
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- 238000006482 condensation reaction Methods 0.000 claims description 4
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
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- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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Abstract
The invention relates to the technical field of biomedicine, and particularly discloses a compound, an oat bran extract and application of the compound and the oat bran extract in preparation of a product with an antioxidant or anti-inflammatory effect. The compound has a structure shown in a formula I. The oat bran extract is prepared by the following method: adding ethyl acetate and water into oat bran, mixing uniformly, standing, extracting to obtain an aqueous phase layer, and concentrating and drying the aqueous phase layer to obtain the oat bran extract. Researches show that the compound with the structure shown in the formula I and the oat bran extract have antioxidant and anti-inflammatory effects; therefore, the compound can be used as an effective component for preparing foods, health products, cosmetics, skin care products or medicines with antioxidant or anti-inflammatory effects.
Description
Technical Field
The invention relates to the technical field of biomedicine, in particular to a compound, an oat bran extract and application thereof in preparing a product with antioxidant or anti-inflammatory effects.
Background
Skin aging is a naturally occurring physiological process, but stimulation by certain adverse external factors can cause further damage to the skin and accelerate the aging process. For example, excessive or prolonged uv irradiation can cause extensive degradation of collagen, elastin, etc. in skin cells, elastosis, etc. Such skin aging caused by external environmental factors and the like is called extrinsic aging. Research finds that UVB is a wave band with great harm to organisms in ultraviolet rays, and UVB irradiation can inhibit collagen synthesis: promoting the release of inflammatory factors and increasing ROS; increased expression and secretion of matrix metalloproteinase 1 (MMP-1); MMP and the like.
Some small molecule compounds found in plants have been shown to have some photodamage protection to the skin. Peptides and phenol micromolecular compounds contained in traditional Chinese medicines have various biological activities of resisting oxidation, removing free radicals, resisting inflammation, resisting aging and the like, can play a role in preventing and treating skin photodamage, and are widely regarded and applied clinically. Therefore, the development of more compounds with novel structures and one of the biological activities has important application value.
Disclosure of Invention
In view of the above, the invention firstly provides a compound with a brand-new structure, and further research shows that the compound has antioxidant and anti-inflammatory effects.
The detailed technical scheme of the invention is as follows:
the invention firstly provides a compound which has a structure shown in a formula I;
further, we also provide a process for the preparation of the above compound comprising the steps of:
(1) carrying out condensation reaction on 3,4, 5-trimethoxybenzoic acid and 1, 3-propane diamine to generate an intermediate product N- (3-aminopropyl) -2,3, 4-trimethoxybenzamide;
(2) and (3) carrying out condensation reaction on the intermediate product N- (3-aminopropy) -2,3,4-trimethoxybenzamide and (tert-butoxycarbonyl) phenylanine to obtain the compound with the structure shown in the formula I.
Further, we provide another preparation method of the above compound, which is extracted from oat bran.
The invention also provides an oat bran extract, which is prepared by the following method: adding ethyl acetate and water into oat bran, mixing uniformly, standing, extracting to obtain an aqueous phase layer, and concentrating and drying the aqueous phase layer to obtain the oat bran extract.
Preferably, the using ratio of the oat to the ethyl acetate to the water is 1: 4-6: 8 to 12.
Most preferably, the oat, ethyl acetate and water are used in a ratio of 1: 5: 10.
preferably, the compound with the structure shown in the formula I is also added into the oat bran extract.
Preferably, the compound of formula I is added in an amount of 1-20% by weight based on the weight of the oat bran extract.
Further preferably, the weight of the compound with the structure shown in the formula I is 5-15% of the weight of the oat bran extract.
Most preferably, the compound of formula I is added in an amount of 10% by weight based on the weight of the oat bran extract.
The invention also provides application of the compound or the oat bran extract in preparing products with antioxidant or anti-inflammatory effects.
Preferably, the product is a food, a health product, a cosmetic, a skin care product or a medicament.
Has the advantages that: the invention firstly provides a compound with a brand-new structure and a structure shown in a formula I; research shows that the antioxidant and anti-inflammatory agent has excellent antioxidant and anti-inflammatory effects; especially has excellent effect of resisting oxidative damage and inflammatory damage of skin cells caused by UVB. The compound with the structure shown in the formula I can be prepared by a synthetic method and can also be extracted from oat bran. Further research shows that the oat bran extract prepared by the method also has the effects of oxidation resistance and anti-inflammation; especially has excellent effects of resisting oxidative damage and inflammatory damage of skin cells caused by UVB. In addition, the antioxidant and anti-inflammatory effects of the oat bran extract can be further enhanced by adding the compound with the structure shown in the formula I into the oat bran extract. The compound with the structure shown in the formula I and the oat bran extract have antioxidant and anti-inflammatory effects; therefore, the compound can be used as an effective component for preparing foods, health products, cosmetics, skin care products or medicines with antioxidant or anti-inflammatory effects.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only drawings of some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a graph showing the results of high performance liquid chromatography measurement of ASH.
FIG. 2 is of ASH 1 H-NMR spectrum.
FIG. 3 is of ASH 13 C-NMR spectrum.
FIG. 4 is a graph showing the results of ASH, AST, ASA inhibition experiments on cell viability reduction induced by UVB irradiation on HaCaT cells.
FIG. 5 is a graph showing the results of ASH, AST, and ASA experiments to inhibit the increase of intracellular ROS content induced by UVB irradiation of HaCaT cells.
FIG. 6 is a graph showing the results of experiments on inhibition of increase of inflammatory cytokine secretion from HaCaT cells by irradiation of UVB by ASH, AST and ASA.
ASH in the figures and the following examples is a shorthand for a compound of the structure shown in formula I; AST is shorthand for the oat bran extract prepared in example 3; ASA is a shorthand for the oat bran extract prepared in example 2.
Detailed Description
The technical solution of the present invention will be clearly and completely described with reference to the following examples. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Preparation of the Compound of example 1
(1) The reaction substrate 3,4, 5-trimethoxybenzoic acid (1.0g) was weighed into a 100mL clean round bottom flask, magneton was placed, 40mL of anhydrous dichloromethane was added, 1, 3-propanediamine (1.99g) was added with stirring, and HATU (4.87g) was added after 5 minutes. After the end of the addition, the reaction was continued at room temperature for 5 hours and the disappearance of the reaction material was monitored by TLC. The stirring was stopped, the reaction was evaporated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (200-mesh 300) to give a white solid which was identified as N- (3-aminopropy) -2,3, 4-trimethoybenzamide.
(2) The reaction material N- (3-aminopropy) -2,3,4-trimethoxybenzamide (1.0g) was weighed into a 100mL clean round-bottom flask, magneton was placed, 35mL dry dichloromethane was added, and tert-butoxycarbnyl phenyl alanine (2.66g) was added with stirring. After the addition, the reaction system is stirred for 10 minutes at room temperature, the reaction is continued for 4 hours at room temperature, TLC monitors the disappearance of the reaction raw materials and stops stirring, the reaction system is decompressed and evaporated to remove the solvent, and the residue is purified by silica gel column chromatography (200-mesh and 300-mesh) to obtain a white solid.
Please note that the nuclear magnetic data for the compounds of formula I are as follows: 13 C NMR(400MHz,MeOD)δ:7.66(1H,d,J＝8.2Hz),7.26(5H,m),6.87(1H,d,J＝8.2Hz),3.98(3H,s,-OCH 3 ),3.89(3H,s,-OCH 3 ),3.85(3H,s,-OCH 3 ),3.31(4H,m,2-CH 2 -),3.08(1H,m,-CH-),2.88(1H,m,-CH-),1.70(2H,m,-CH 2 -),1.38(9H,s,3-CH 3 )； 13 C NMR(100MHz,MeOD)δ173.03,166.41,156.61,156.11,152.36,141.86,137.24,129.02,128.08,126.37,125.49,119.22,107.44,79.26,61.10,60.00,56.33,38.07,36.38,36.22,29.15,27.33.
according to what is shown in figures 2 and 3 1 H-NMR spectrum and 13 the C-NMR spectrum of the compound (abbreviated as ASH, English name is tert-butyl (1-oxo-3-phenyl-1- ((3- (2,3, 4-trimethoxbenzamido) p) can confirm that the compound with the structure shown in the formula I is preparedropyl)amino)propan-2-yl)carba mate)。
Example 2 preparation of oat bran extract
Mixing 100g of oat with 500mL of ethyl acetate and 1000mL of water, standing, extracting to obtain an aqueous phase layer, repeating the extraction process of 3, combining the aqueous phase layers, and performing vacuum low-temperature freeze drying on the aqueous phase layer to obtain the oat bran extract (abbreviated as ASA).
Example 3 preparation of oat bran extract
(1) Mixing the oat bran extract prepared in the example 2 with a compound with a structure shown in a formula I; wherein, the weight of the compound with the structure shown in the formula I is 10 percent of the weight of the oat bran extract prepared in the example 2;
(2) adding water for re-dissolving, and vacuum lyophilizing at low temperature to obtain oat bran extract (AST).
Examples of the experiments
To evaluate the biological activity of ASH, AST, ASA of the present invention, the following effect examples were conducted.
Culturing HaCaT cells of immortalized keratinocyte cell line in a cell culture box at 37 ℃ and 5% CO 2 (DMEM medium). The irradiation intensity of UVB is 7.15 multiplied by 10 -5 J/cm 2 The irradiation light source was spaced 15cm from the cells. During irradiation, the culture cell culture solution of each group is sucked off, washed for 2 times by PBS, and then a small amount of solution is added to cover the bottom surface to avoid drying. The plates were irradiated in a room temperature water bath to avoid overheating after irradiation. After irradiation, PBS is discarded, DMEM culture medium or culture medium containing ASH, AST and ASA is added again for continuous culture for 24 h. The CCK8 method is used for detecting cell viability and collecting cells and culture solution.
In the test of the effect of compounds on the viability of HaCaT cells, the experiments were divided into 5 groups: normal Control group (Control); a UVB irradiation group; ASA (UVB irradiation + ASA 10. mu.g/mL); AST group (UVB irradiation + AST 10. mu.g/mL), ASH group (UVB irradiation + ASH 10. mu.g/mL). Each treatment condition was replicated 3 times in 3 wells and the experiment was repeated 3 times. The normal control group did not receive UVB irradiation, and the UVB irradiation group, ASA group, AST group, and ASH group received UVB irradiation, respectively, and the test results are shown in fig. 4.
As can be seen from the data in FIG. 4, the activities of the HaCaT cells irradiated by UVB are obviously improved by ASH, AST and ASA. The compound with the structure shown in the formula I, the oat bran extract prepared in the example 3 and the oat bran extract prepared in the example 2 can improve the activity of HaCaT cells against UVB damage and reduce damage caused by UVB irradiation; all have the effect of resisting oxidative damage and inflammatory damage of skin cells caused by UVB.
Further, as can be seen from the data in fig. 4, the viability of the HaCaT cells irradiated by UVB is improved most significantly by the ASH group, which is greater than that of the ASA group and the AST group; this demonstrates that the compounds of formula I are most effective against oxidative and inflammatory damage of skin cells caused by UVB, which is better than oat bran extract.
After the HaCaT cells are treated according to the experimental design, the cells are collected; and (4) detecting the secretion amount of the ROS by referring to an ELISA kit operating instruction. After HaCaT cells are treated according to experimental design, collecting cell culture fluid; and (4) detecting the secretion amounts of IL-6, IL-1 beta and TNF-alpha by referring to the operation instructions of the ELISA kit.
The results are as follows:
as shown in fig. 5, UVB irradiation significantly increased the intracellular ROS content in HaCaT compared to Control, whereas ASA, AST and ASH treatment significantly inhibited the UVB irradiation-induced increase in intracellular ROS content, and ASH activity was greater than ASA and AST.
As shown in FIG. 6, UVB irradiation significantly increased IL-6, IL-1. beta. and TNF-. alpha.secretion by HaCaT cells, indicating that UVB irradiation induces severe inflammatory responses in HaCaT cells. And the treatment of ASA, AST and ASH inhibits the secretion and the viscosity of HaCaT cells IL-6, IL-1 beta and TNF-alpha induced by UVB radiation. Wherein the ASH can obviously reduce the secretion of HaCaT cell inflammatory cytokines induced by UVB irradiation. We speculate that ASA, AST and ASH may reduce the damage they cause to the skin by reducing oxidative stress and inflammatory damage of HaCaT cells induced by UVB radiation.
While the invention has been described with reference to a preferred embodiment, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the invention.
Claims (10)
1. A compound having the structure shown in formula i;
2. a process for the preparation of a compound according to claim 1, comprising the steps of:
(1) carrying out condensation reaction on 3,4, 5-trimethoxybenzoic acid and 1, 3-propane diamine to generate an intermediate product N- (3-aminopropyl) -2,3, 4-trimethoxybenzamide;
(2) and (3) carrying out condensation reaction on the intermediate product N- (3-aminopropy) -2,3,4-trimethoxybenzamide and (tert-butoxycarbonyl) phenylanine to obtain the compound with the structure shown in the formula I.
3. The method of claim 1, wherein the compound is extracted from oat bran.
4. An oat bran extract is prepared by the following method: adding ethyl acetate and water into oat bran, mixing uniformly, standing, extracting to obtain an aqueous phase layer, and concentrating and drying the aqueous phase layer to obtain the oat bran extract.
5. The oat bran extract as claimed in claim 4, wherein the oat, the ethyl acetate and the water are used in a ratio of 1: 4-6: 8 to 12.
6. The oat bran extract as claimed in claim 4, wherein the oat, the ethyl acetate and the water are used in a ratio of 1: 5: 10.
7. the oat bran extract as claimed in claim 4, wherein a compound having a structure represented by formula I is further added to the oat bran extract.
8. The oat bran extract as claimed in claim 7, wherein the compound of the structure represented by the formula I is added in an amount of 1 to 20% by weight based on the oat bran extract; further preferably, the weight of the compound with the structure shown in the formula I is 5-15% of the weight of the oat bran extract; most preferably, the compound of formula I is added in an amount of 10% by weight based on the weight of the oat bran extract.
9. Use of a compound as claimed in claim 1 or any one of claims 4 to 8 or an extract of oat bran in the preparation of a product having antioxidant or anti-inflammatory activity.
10. Use according to claim 9, wherein the product is a food product, a health product, a cosmetic product, a skin care product or a pharmaceutical product.
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