CN113527245B - Synthesis method and application of aloe floss - Google Patents
Synthesis method and application of aloe floss Download PDFInfo
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- CN113527245B CN113527245B CN202110723010.8A CN202110723010A CN113527245B CN 113527245 B CN113527245 B CN 113527245B CN 202110723010 A CN202110723010 A CN 202110723010A CN 113527245 B CN113527245 B CN 113527245B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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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
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Abstract
The invention provides a synthesis method and application of aloe pine, which comprises the steps of mixing a compound A, a hydrogen chloride solution and isopropanol, wherein the molar ratio of the compound A to the hydrogen chloride is 1:4.0 to 4.5, heating to 40 to 50 ℃ and stirring for reaction for 1 to 2 hours; concentrating under reduced pressure after reaction to remove solvent to obtain concentrate, and purifying the concentrate by column chromatography to obtain target product aloe pine; the structure of the compound A is shown as a formula (a):
the synthesis method of the aloe pine has the advantages of low cost, easy synthesis, high yield and better industrial production.
Description
Technical Field
The invention relates to the technical field of tyrosinase inhibitors, in particular to a synthesis method and application of aloe pine.
Background
Tyrosinase is a key enzyme in melanogenesis, produced only by melanocytes, which, after production and processing in the endoplasmic reticulum and golgi apparatus, is transported to melanosomes where it is synthesized as melanin. Therefore, regulation of melanin synthesis by inhibition of tyrosinase is a major way to prevent pigmentation. Many tyrosinase inhibitors such as Hydroquinone (HQ), arbutin, kojic acid, azelaic acid, L-ascorbic acid, ellagic acid, tranexamic acid, etc. have been used as whitening agents at present, but have certain drawbacks. In addition to Hydroquinone (HQ) being able to mutagenize mammalian cells, there are also a number of adverse effects including contact dermatitis, allergies, transient erythema, burning, stinging, leukoplakia, castanopsis, hypopigmentation and brown-yellow. Arbutin, a prodrug of hydroquinone, is a natural ingredient that reduces or inhibits tyrosinase activity to inhibit synthesis of melanin. However, the natural form of arbutin is chemically unstable, can release hydroquinone, is decomposed into benzene-containing metabolites, and has potential toxicity to bone marrow. The use of kojic acid in cosmetics is limited due to its carcinogenicity and instability during storage; l-ascorbic acid is sensitive to heat and is easy to deteriorate; ellagic acid is insoluble in water and therefore poorly bioavailable, whereas for tranexamic acid its inhibition of the melanogenesis pathway is still uncertain. Thus, there is an urgent need to develop novel tyrosinase inhibitors having pharmaceutical properties.
Aloe is widely applied in the fields of beauty and health care such as whitening, moisturizing, sun screening, skin aging delaying, slimming, weight losing and the like, and is known as a green skin care product and a natural beauty. Aloesin is an active ingredient of aloe for whitening, antioxidation, sun protection and anti-aging, and is collected into the raw material catalog of cosmetics. However, aloesin is extremely low in content in aloe, and the separation and purification cost is too high, on the other hand, the chemical synthesis of the C-glycoside part in the molecule is difficult, the industrialization is not easy, and the wide application of aloesin is limited. Aloesone (aloesone) is an aglycone of aloesin and is also a characteristic chemical component in aloe epidermis. The aloe pine content in aloe is also low, and the research on related pharmacological activity is also little. In view of the great difficulty in obtaining natural aloe pine, the development of a cheap, simple and high-yield aloe pine synthesis method has great significance.
Disclosure of Invention
In view of the above, the invention provides a synthesis method of aloe pine, which has low cost, easy synthesis, high yield and better industrial production.
The technical scheme of the invention is realized as follows:
a synthesis method of aloe pine comprises the following steps:
mixing a compound A, a hydrogen chloride solution and isopropanol, wherein the molar ratio of the compound A to the hydrogen chloride is 1:4.0 to 4.5, heating to 40 to 50 ℃ and stirring for reaction for 1.4 to 1.6 hours; preferably, the molar ratio of compound a to hydrogen chloride is 1:4, the stirring reaction condition is as follows: heating to 45deg.C, stirring for 1.5 hr, concentrating under reduced pressure to remove solvent to obtain concentrate, and purifying the concentrate by column chromatography to obtain target product of aloe-pine;
the structure of the compound A is shown as a formula (a):
further, the molar ratio of the isopropanol to the compound A is 30-40:1.
further, the solvent for column chromatography is prepared by mixing petroleum ether and ethyl acetate at a mixing volume ratio of 1-5:1, preferably 5:1.
Further, the synthesis method of the compound A comprises the following steps: mixing compound B, sodium hydroxide and dimethyl sulfoxide, stirring at 20-30deg.C for 7.5-8.5 hr, extracting with ethyl acetate and water, collecting ethyl acetate layer, concentrating under reduced pressure to remove solvent to obtain concentrate, purifying the concentrate by column chromatography, and mixing petroleum ether and ethyl acetate at volume ratio of 4.8-5.2:1 to obtain compound A.
The structure of the compound B is shown as a formula (B):
the molar ratio of the compound B to the sodium hydroxide is 1:2.2-2.8;
the mol volume ratio mol/L of the compound B to the dimethyl sulfoxide is 1:4.0-4.2.
Further, the synthesis method of the compound B comprises the following steps:
mixing a compound C, malic acid, 4-dimethylaminopyridine and methylene dichloride, stirring in an ice bath to react to 0 ℃, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride, and stirring at 20-30 ℃ to react for 5.8-6.2h;
extracting with dichloromethane and water after reaction, collecting dichloromethane layer, concentrating under reduced pressure to remove solvent to obtain concentrate, purifying the concentrate by column chromatography, wherein the solvent of column chromatography is prepared by mixing petroleum ether and ethyl acetate at volume ratio of 5.8-6.2:1 to obtain compound B;
the structure of the compound C is shown as a formula (C):
the molar ratio of the compound C, malic acid and 4-dimethylaminopyridine is 1:1.0-1.1:1.0-1.1;
the mol volume ratio mol/L of the compound C and the methylene dichloride is 1:4.0-4.2.
Tyrosinase inhibitor or whitening agent, comprising the target product aloe vera obtained by any one of the synthetic methods of the present invention.
Compared with the prior art, the invention has the beneficial effects that:
the invention takes cheap and easily available 3, 5-dihydroxytoluene as raw material, synthesizes aloesin aglycone aloeresin through acylation reaction, esterification reaction, substitution reaction and the like, wherein, under the condition of isopropanol solvent, a certain proportion of compound A and hydrogen chloride are adopted for reaction, the aloe pine which is a target product is obtained after purification by combining certain reaction temperature and reaction time, the tyrosinase inhibition activity of the aloe pine is 4 times that of aloesin, the aloe pine is smaller than aloesin molecules, the polarity is smaller, the aloe pine is easier to enter cells, and the whitening effect is better than aloesin; on the basis of relatively high yield, the method is low in cost, environment-friendly, easy to synthesize and capable of achieving better industrial production. The aloe pine prepared by the invention can be well applied to preparing tyrosinase inhibitors or whitening agents.
Drawings
FIG. 1 is a hydrogen spectrum of aloe vera pine synthesized in example 1 of the present invention;
FIG. 2 is a graph of the carbon spectrum of aloe vera pine synthesized in example 1 of the present invention.
Detailed Description
In order to better understand the technical content of the present invention, the following provides specific examples to further illustrate the present invention.
The experimental methods used in the embodiment of the invention are conventional methods unless otherwise specified.
Materials, reagents, and the like used in the examples of the present invention are commercially available unless otherwise specified.
The chinese names of the compounds used in the present invention are shown in table 1 below:
table 1 Chinese names of Compounds
The compound A of the invention is compounds 1-4;
the compound B of the invention is compounds 1-3;
the compound C of the invention is a compound 1-2.
The reactant HCl in the embodiment of the invention adopts commercial concentrated hydrochloric acid as a raw material and is a hydrogen chloride solution with the mass concentration of 38% of HCl.
Synthesis route of aloe pine
EXAMPLE 1 Synthesis of Aloes
(1) Synthesis of intermediates
Synthesis of Compound 1-1
In a 100mL round bottom flask was added the compound 3, 5-dihydroxytoluene (10 mmol,1.24 g) and acetic acid (8 mmol,0.48 g) and boron trifluoride etherate (2.48 mL,20 mmol) and the reaction was magnetically stirred at 80℃for 12h. After the reaction is completed, the mixture is cooled to room temperature, extracted by ethyl acetate and water for three times, and an ethyl acetate layer is taken and added into saturated NaHCO 3 In the solution (10 ml), the mixture was stirred for 10min to complete the reaction of acetic acid in the solution. ThenExtracting with ethyl acetate and water for three times, collecting ethyl acetate layer, concentrating under reduced pressure to remove solvent to obtain concentrate, adding ethyl acetate to dissolve the concentrate, adding petroleum ether, standing, and recrystallizing. After suction filtration, a yellow powdery solid, namely compound 1-1, was obtained.
Synthesis of Compounds 1-2
In a 200mL round bottom flask was added compound 1-1 (10 mmol,1.66 g) and dichloromethane 35mL, DIPEA (8.4 mL,65 mmol), and after magnetically stirring the reaction in ice bath to 0deg.C, MEM-Cl (10 mmol,1.25 mL) was added and the reaction was magnetically stirred at room temperature for 12h. Extracting with ethyl acetate and water after the reaction, extracting for three times, collecting ethyl acetate layer, concentrating under reduced pressure to remove solvent to obtain concentrate, and purifying with column chromatography (petroleum ether: ethyl acetate=6:1, v/v) to obtain oily liquid, namely compound 1-2.
Synthesis of Compounds 1-3
In a 100ml round bottom flask were added compound 1-2 (10 mmol,2.54 g), malic acid (10 mmol,2.19 g), DMAP (1.22 g,10 mmol) and dichloromethane (40 ml) and after magnetically stirring the reaction to 0deg.C in an ice bath. EDC. HCl (3.82 g,20 mmol) was added and the reaction was stirred magnetically at room temperature for 6h. Extracting with dichloromethane and water after the reaction, extracting for three times, collecting dichloromethane layer, concentrating under reduced pressure to remove solvent, and purifying the concentrate by column chromatography (petroleum ether: ethyl acetate=6:1, v/v) to obtain colorless oily liquid, namely compound 1-3 (1.72 g, yield 45%).
Synthesis of Compounds 1-4
Compounds 1-3 (10 mmol,3.82 g) and NaOH (0.96 g,24 mmol) and DMSO (40 ml) were added to a 200ml round bottom flask and the reaction was magnetically stirred at room temperature for 8h. Extracting with ethyl acetate and water after the reaction, extracting for three times, collecting ethyl acetate layer, concentrating under reduced pressure to remove solvent, purifying the concentrate by column chromatography (petroleum ether: ethyl acetate=5:1, v/v), and concentrating under reduced pressure to obtain yellow oily liquid, namely compound 1-4 (1.92 g, yield 50%).
(2) Synthesis of aloe-pine
Compounds 1-4 (10 mmol,3.82 g) and concentrated hydrochloric acid (3.4 ml, 40mmol as HCl) and isopropanol (327 mmol,20 ml) were added to a 200ml round bottom flask and heated to 45℃with magnetic stirring for 1.5h. After the completion of the reaction, most of the solvent was removed by concentration under reduced pressure to give a concentrate, which was purified by column chromatography (petroleum ether: ethyl acetate=5:1, v/v), and concentrated under reduced pressure to give compound 1-5 (1.49 g, yield 64%).
Aloe nuclear magnetic data: 1 H NMR(400MHz,DMSO-d 6 )δ10.61(s,1H),6.62(s,1H),6.60(s,1H),6.03(s,1H),3.85(s,2H),2.65(s,3H),2.21(s,3H)； 13 C NMR(100MHz,DMSO-d 6 )δ202.87,178.22,161.09,160.62,159.27,141.65,116.70,114.39,112.92,100.58,47.58,29.89,22.48.
EXAMPLE 2 Synthesis of aloe-pine
Based on the embodiment 1, the synthesis process parameters of the aloe pine in the step (2) are adjusted, specifically:
compounds 1-4 (10 mmol) and concentrated hydrochloric acid (40 mmol as HCl) and isopropanol (300 mmol) were added to a 200ml round bottom flask and heated to 40℃with magnetic stirring for 1.6h. Concentrating under reduced pressure after the reaction, removing most of the solvent to obtain concentrate, purifying with column chromatography (petroleum ether: ethyl acetate=5:1, v/v), concentrating under reduced pressure to obtain white solid, namely compound 1-5, with yield of 62%.
EXAMPLE 3 Synthesis of aloe-pine
The difference between this example and example 1 is the synthesis of aloe-pine in step (2), which is specifically:
compounds 1-4 (10 mmol) and concentrated hydrochloric acid (45 mmol as HCl) and isopropanol (400 mmol) were added to a 200ml round bottom flask and heated to 50deg.C with magnetic stirring for 1.4h. Concentrating under reduced pressure after the reaction, removing most of the solvent to obtain concentrate, purifying with column chromatography (petroleum ether: ethyl acetate=5:1, v/v), concentrating under reduced pressure to obtain white solid, namely compound 1-5, with yield of 63%.
Comparative example 1
Based on example 1, the isopropyl alcohol in step (2) was replaced with 1, 4-dioxane, acetone, methanol, dimethyl sulfoxide. The results are shown in Table 2 below:
when 1, 4-dioxane was used as a solvent, the yield was 50%, and the solid precipitated during the reaction was an impure product and was inconvenient to purify again. When acetone is used as a solvent, the yield is 60 percent, which is lower than that of isopropanol, and the acetone is an easy-to-poison chemical. When methanol was used as a solvent, the yield was 20%. When dimethyl sulfoxide is used as a solvent, little reaction occurs. The invention adopts isopropanol as a reaction solvent, which is not only favorable for full reaction, but also safer.
TABLE 2 results of solvent comparative experiments
Comparative example 2
Based on example 1, the HCl addition in step (2), i.e., the concentrated hydrochloric acid addition, was adjusted. The results are shown in Table 3 below: when the molar ratio of compounds 1-4 to HCl is 1:3, the reaction is incomplete; when the molar ratio of compounds 1-4 to HCl was 1:5, the amount of concentrated hydrochloric acid added was increased as compared with example 1, and the yield was rather decreased. The invention adds a certain amount of HCl, which not only improves the reaction efficiency, but also saves the cost.
TABLE 3 comparison of HCl addition level test results
Comparative example 3
Based on example 1, the stirring reaction time of the aloe-pine synthesis step of step (2) was adjusted. The results are shown in Table 4 below: when the reaction time is 0.5h or 1h, the reaction is incomplete; the reaction time is 2 hours or 2.5 hours, and the reaction byproducts are obviously increased. The invention prefers a certain reaction time, which not only makes the reaction complete, but also reduces the generation of byproducts and improves the reaction efficiency.
Table 4 results of reaction time vs. test
Comparative example 4
Based on example 1, the stirring reaction temperature of the aloe-pine synthesis step of step (2) was adjusted. The results are shown in Table 5 below: the reaction temperature is lower or higher, and the reaction effect is poor. The invention adopts a certain reaction temperature to make the reaction full, effectively improves the reaction efficiency and saves the energy consumption.
TABLE 5 reaction temperature comparative test results
Test examples
Tyrosinase inhibition activity assay was performed on the compounds 1-6 (aloe vera) prepared in example 1
Adding phosphate buffer solution, sample solution (aloe vera) and tyrosine solution into 96-well plate according to Table 6, heating at 37deg.C for 10min, adding tyrosinase solution, mixing, heating at 37deg.C for 10min, and measuring absorbance A at 475nm with enzyme-labeled instrument a 、A b 、A c 、A d The inhibition of tyrosinase by the sample was then calculated as follows.
Inhibition ratio = [1- (A) d -A c /(A b -A a )]*100％
TABLE 6 composition of reaction solution
TABLE 7 inhibition of tyrosinase activity by aloe vera pine
The test results show (Table 7) that the inhibition activity of the aloe-pine is 4 times that of aloesin, the aloe-pine has no glycosyl, the polarity is smaller than that of aloesin, the molecules are also smaller than that of aloesin, the aloe-pine is easy to be absorbed by cells, and the chemical synthesis of the aloe-pine is easy, so that the aloe-pine can be applied to the preparation of tyrosinase inhibitors or whitening agents.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (3)
1. A synthesis method of aloe pine is characterized by comprising the following steps:
mixing a compound A, concentrated hydrochloric acid and isopropanol, wherein the molar ratio of the compound A to the hydrogen chloride is 1: 4.0-4.5, heating to 40-50 ℃ and stirring for reaction for 1.4-1.6h;
concentrating under reduced pressure after reaction to remove solvent to obtain concentrate, and purifying the concentrate by column chromatography to obtain target product aloe pine;
the structure of the compound A is shown as a formula (a):
the mol ratio of the isopropanol to the compound A is 30-40:1, a step of;
the solvent for the column chromatography is prepared by mixing petroleum ether and ethyl acetate;
the volume ratio of petroleum ether to ethyl acetate is 1-5:1;
the synthesis method of the compound A comprises the following steps:
mixing compound B, sodium hydroxide and dimethyl sulfoxide, stirring at 20-30deg.C for reaction for 7.5-8.5. 8.5h, extracting with ethyl acetate and water, collecting ethyl acetate layer, concentrating under reduced pressure to remove solvent to obtain concentrate, purifying the concentrate by column chromatography, and mixing petroleum ether and ethyl acetate at volume ratio of 4.8-5.2:1 to obtain compound A;
the structure of the compound B is shown as a formula (B):
the molar ratio of the compound B to the sodium hydroxide is 1:2.2-2.8;
the mol volume ratio mol/L of the compound B to the dimethyl sulfoxide is 1:4.0-4.2.
2. The method for synthesizing aloe vera according to claim 1, wherein the molar ratio of compound a to hydrogen chloride is 1:4.
3. the method for synthesizing aloe vera according to claim 1, wherein the method for synthesizing the compound B comprises:
mixing a compound C, malic acid, 4-dimethylaminopyridine and methylene dichloride, stirring in an ice bath to react to 0 ℃, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride, and stirring at 20-30 ℃ to react for 5.8-6.2h;
extracting with dichloromethane and water after reaction, collecting dichloromethane layer, concentrating under reduced pressure to remove solvent to obtain concentrate, purifying the concentrate by column chromatography, wherein the solvent of column chromatography is prepared by mixing petroleum ether and ethyl acetate at volume ratio of 5.8-6.2:1 to obtain compound B;
the structure of the compound C is shown as a formula (C):
the molar ratio of the compound C, malic acid and 4-dimethylaminopyridine is 1:1.0-1.1:1.0-1.1;
the mol volume ratio mol/L of the compound C and the methylene dichloride is 1:4.0-4.2.
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| JP2002500167A (en) * | 1998-01-12 | 2002-01-08 | ユニバーラ ファーマスーティカルズ，インコーポレイテッド | Method for synthesizing aloecin derivatives |
| GB0108671D0 (en) * | 2001-04-06 | 2001-05-30 | Dinan Etsuko | Skin treatment |
| JP5141023B2 (en) * | 2007-01-24 | 2013-02-13 | 独立行政法人科学技術振興機構 | Aloeson synthase |
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| EP3307900A1 (en) * | 2015-06-10 | 2018-04-18 | Danmarks Tekniske Universitet | Use of heterologous expressed polyketide synthase and small molecule foldases to make aromatic and cyclic compounds |
| KR102187682B1 (en) * | 2018-06-08 | 2020-12-07 | 한국과학기술원 | Novel Enzyme-coupled Malonyl-CoA Biosensor based on Type III Polyketide Synthase and Use of the same |
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