CN105924342A - Synthetic method and application of 1,5-bis-(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-dione - Google Patents
Synthetic method and application of 1,5-bis-(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-dione Download PDFInfo
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- CN105924342A CN105924342A CN201610330840.3A CN201610330840A CN105924342A CN 105924342 A CN105924342 A CN 105924342A CN 201610330840 A CN201610330840 A CN 201610330840A CN 105924342 A CN105924342 A CN 105924342A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
- A23B7/154—Organic compounds; Microorganisms; Enzymes
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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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
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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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
Abstract
The invention discloses a synthetic method and application of 1,5-bis-(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-dione and belongs to the fields of food, cosmetics and medicines. By reacting 3,4-dihydroxy benzaldehyde and 2,4-resacetophenone under the catalysis of boric acid and vitamin C for 6 hours with PEG400 as a solvent, an efficient tyrosinase inhibitor is synthesized in an environment-friendly mode; then, separation is carried out through column chromatography on silica gel and gel column chromatography, and a purified product of the efficient tyrosinase inhibitor is obtained. By means of mass spectrum and nuclear magnetism analysis, the purified product is determined as 1,5-bis-(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-dione. The compound can be effectively used for inhibiting enzymatic browning of fruits and vegetables, skin whitening cosmetics and preparing medicine preparations used for preventing and treating human body chromatosis diseases and melanoma caused by too much melanin and needed for inhibiting activity of tyrosinase.
Description
Technical field
The present invention relates to 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, the synthetic method of 5-diketone and application thereof, belong to food, cosmetics and field of medicaments.
Background technology
The corruption that brown stain and pathogenic infection cause is two key factors causing postharvest fruit and vegetable to lose.In garden stuff processing and storage, the enzymatic browning caused by tryrosinase (EC 1.14.18.1) not only affects the color and luster of product, outward appearance, and the aminoacid of necessary product can be destroyed, reduce its nutrition and digest and assimilate, and finally have a strong impact on nutritive value and the market value of product.Many fruit and vegerable are owing to being affected by fungal disease, mechanical damage and the factor such as aging and causing the shelf-life the shortest.Under normal circumstances, during natural flora is usually present in fruit and vegetable food, it is also possible to during being present in human consumption, they there typically are not toxicity to the mankind；But, producing, gathering in, transporting and be processed further in processing procedure, fruit and vegetable food all may be caused to be polluted by microorganism.Mechanical damage and destruction more can increase the weight of the pollution of brown stain and microorganism.Use tyrosinase inhibitor and antibacterial can control postharvest fruit and vegetable brown stain and disease.
Chalcones is a class of flavone compound, has tyrosinase inhibitory activity, the most antibacterial, anticancer, antiinflammatory and antioxidation isoreactivity.Natural chalcone is widely present in water fruits and vegetables, spice, tea, soy food product and some Chinese herbal medicine.The main method of at present chalcone synthesis is that aromatic aldehyde and 1-Phenylethanone. are in the basic conditions by Clasein-Schmidt condensation reaction.In the past few decades, the method developing many synthesizing chalcones from research worker all over the world.But, these methods have a lot of defect, such as harsh reaction condition, toxic reagent and metallic catalyst, strong acid and strong base, oil product, long response time, low-yield, low selectivity and loaded down with trivial details post processor.It addition, in most cases, synthesis of hydroxy chalcone derivative needs protection and deprotection hydroxyl, not only increases reaction step number and time, the most also increases and use the poisonous or chance of harmful reagent.Although also having some green synthesis methods at present, as used calcium hydroxide to make catalyst, spent glycol is as reaction dissolvent etc., but these green synthesis methods equally exist the problems such as low-yield, oil product and loaded down with trivial details post processing.
Green synthesis method because of its environmental friendliness, subtract the characteristics such as dirty reduction of discharging, in scientific research and industrial application, there is far-reaching Research Significance and important using value.Along with the raising day by day of environmental protection, economy and social desirability, to use nontoxic raw material, solid acid/base catalyst and the green solvent green synthetic chemistry as representative to become the focus of research both at home and abroad.By the present invention in that the method by gentleness, selection innoxious solvent is as reaction dissolvent, and selects non-toxic catalyst, and synthesis has a kind of Hydroxylated Chalcones and Related Derivatives of higher tyrosinase inhibitory activity.
Summary of the invention
It is an object of the invention to provide a kind of compound having tyrosinase inhibitory activity, by 3,4-4-dihydroxy benzaldehyde and 2,4-resacetophenone prepares at boric acid and ascorbic catalysis, named 1,5-bis-(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-dione, its Chinese name is 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone, its structure is as follows:
Another object of the present invention is to provide described 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, and the green synthesis method of 5-diketone is realized by following steps:
(1) 3,4-4-dihydroxy benzaldehyde and 2,4-dihydroxyacetophenone, under boric acid and ascorbic catalysis, with PEG400 or ethylene glycol or ethanol or methanol etc. as solvent, react 3～6 hours in 100～130 DEG C；
(2) reactant liquor ethyl acetate, dichloromethane, ether or chloroform etc. extract 3-5 time, and organic facies is concentrated to give drying sample；
(3) silicagel column on drying sample, eluant is with the dichloromethane of volume ratio 30:1 mixing: methanol；
(4) eluate sample that step (3) is collected is concentrated to give drying sample, again through Sephadex LH-20 gel filtration chromatography: isolated 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone.
One embodiment of the present invention, mainly comprises the steps that
(1) 3,4-4-dihydroxy benzaldehyde and 2,4-dihydroxyacetophenone, under boric acid and ascorbic catalysis, react 6 hours with PEG400 for solvent 130 DEG C；3,4-4-dihydroxy benzaldehydes and 2, the mol ratio of 4-hydroxyacetophenone is 1:1；
(2) reactant liquor is extracted with ethyl acetate 3 times, and organic facies is evaporated to be dried, and obtains drying sample；
(3) silicagel column on drying sample, eluant is with the dichloromethane of volume ratio 30:1 mixing: methanol；
(4) concentrated being dried of eluate sample that step (3) is collected to obtain drying sample, and through Sephadex LH-20 gel filtration chromatography, eluant is that collection eluent, same stream deciliter also obtains product with the methanol-water of volume ratio 7:3 mixing.
One embodiment of the present invention, step (3) described silicagel column be granularity be the silica gel of 200-300 mesh.
Provided by the present invention 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone can be applicable to prepare anti-fruit and vegerable inhibition of enzymatic browning agent, white-making ingredient, prevent and treat melanin abnormal cause human pigmentation's property disease, melanoma and other need to suppress in the medicine of the disease of tyrosinase activity, can be as active component, it is not added with or adds the adjuvant accepted on food additive adjuvant, cosmetic or medicament, making preparation according to the preparation method of corresponding dosage form.
Described dosage form include pressed powder, aqueous solution, alcoholic solution, emulsion, facial film, cataplasma, injection, drip liquid, injectable powder, granule, tablet, electuary, powder, oral liquid, sugar-coat agent, film coated tablet, enteric coated tablet, capsule, hard capsule, soft capsule, suck agent, granule, pill, unguentum, sublimed preparation, spray, drop pill, disintegrating agent, mouth collapse agent, micropill etc..
The invention have benefit that: a kind of compound with tyrosinase inhibitory activity is provided, it have than positive control kojic acid, 2,4-resacetophenone and 3, the activity that 4-4-dihydroxy benzaldehyde is higher, make corresponding preparations and be prone to quality control, can be applicable to anti-fruit and vegerable inhibition of enzymatic browning agent, white-making ingredient, prevent and treat melanin abnormal cause human pigmentation's property disease, melanoma and other need to suppress in the medicine of the disease of tyrosinase activity.
Accompanying drawing explanation
Fig. 1 is compound 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone1H H NMR spectroscopy
Fig. 2 is compound 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone13C H NMR spectroscopy
Fig. 3 is compound 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, the hsqc spectrum of 5-diketone
Fig. 4 is compound 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, the HMBC spectrum of 5-diketone
Fig. 5 is compound 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, the ESI-MS spectrum of 5-diketone
Detailed description of the invention
Embodiment 11,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, the preparation of 5-diketone
Weigh 0.04mol 3,4-4-dihydroxy benzaldehyde, 0.04mol 2,4-dihydroxyacetophenone, 2.1g boric acid, 0.5g ascorbic acid, in 50mL round-bottomed flask, add the PEG400 stirring and dissolving of 25mL, it is placed in 130 DEG C of oil baths and is stirred at reflux 6h, TLC tracking reaction process.Reactant liquor is extracted with ethyl acetate three times, and organic facies is evaporated to be dried；Silicagel column (granularity: 200～300 mesh) on dried sample, use dichloromethane: methanol=30:1 (v/v) eluting, collect eluent, lamellae detect, same stream deciliter also, concentrate drying, obtain drying sample；By LC-MS technology, determine that the flow point that molecular weight is 392 is the flow point containing object；Above flow point drying sample methanol separates with gel filtration chromatography (Sephadex LH-20) after dissolving again, methanol-water (v/v, 7:3) eluting；Collecting eluent, lamellae detects, and same stream deciliter also, obtains 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone.
Reaction expression is:
1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, the spectroscopic data of the nuclear magnetic resonance of 5-diketone is as follows:
1H NMR(Acetone-d6, 400MHz) and δ: 12.736 (2H, s, OH-2,2'), 7.896 (2H, d, J=9.2Hz, H-6,6'), 7.837 (1H, s, H-6 "), 6.680 (2H; s, overlapped, H-2 ", 5 "), 6.428 (2H, dd; J=8.8,2.4Hz, H-5,5'), 6.289 (2H, d; J=2.4Hz, H-3,3'), 3.901 (1H, m, H-9); 3.374 (4H, dd, J=9.8,5.4Hz, H-8,8')；13C NMR(Acetone-d6, 100MHz) and δ: 204.497 (C=O, C-7,7'), 166.461 (C, C-2,2'), 165.640 (C, C-4,4'), 145.849 (C, C-4 "); 144.554 (C, C-3 "), 136.545 (C, C-1 "); 133.867 (CH, C-6,6'), 119.766 (CH; C-6 "), 116.105 (CH, C-5 "); 115.785 (CH, C-3 "), 114.358 (C, C-1,1'), 108.848 (CH, C-5,5'), 103.701 (CH, C-3,3'), 45.034 (CH2,C-8,8'),38.267(CH,C-9)。
ESI-MS:m/z 423.0[M-H]-(C23H19O8).Resolve in conjunction with two-dimensional spectrum HSQC, HMBC and show that this compound is 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone.
HPLC-MS testing conditions:
(1) instrument: Waters UPLC-mass spectrograph.
(2) chromatographic column: Acquity BEH C18 (50 × 2.1mm, 1.7 μm).
(3) flowing phase: A phase: containing the deionized water of 0.2% formic acid；B phase: acetonitrile.Linear eluent gradient: 0min, 10%B；0.1min, 10%B；18min, 70%B；20min, 100%B；20.1min, 10%B.Flow velocity: 0.3mL/min.
(4) sample size: 1 μ L.
(5) Mass Spectrometry Conditions: negative ion mode；Spray voltage: 2.8V；Ion source temperature: 120 DEG C；Desolventizing temperature: 350 DEG C.
Embodiment 2 tyrosinase inhibitory activity evaluation methodology
By 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone DMSO dissolves and is made into 50,10,5,2.5,0.5 μ g/mL respectively.Take each 300 μ L of solution of five kinds of concentration, it is made into 1mL by the phosphate buffered solution of 700 μ L pH6.8, add the tyrosine 1mL of 0.1mg/mL, it is subsequently adding the 1mL tryrosinase (400U/mL) being made into by the phosphate buffered solution of pH value 6.8, at 37 DEG C, hatch 20min, at 492nm, measure light absorption value.
Inhibition of enzyme activity rate=[(A2-A1)-(B2-B1)]/(A2-A1) × 100%
A1 is the absorption value of unchecked dose when being 0min；A2 is the absorption value of unchecked dose after 20min；
The absorption value of inhibiting time B1 is 0min；B2 is the absorption value having added inhibitor after 20min.
Embodiment 3 compound tyrosinase inhibitory activity is evaluated
1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, the IC of 5-diketone suppression tryrosinase50For 0.167mM, the IC of 3,4-4-dihydroxy benzaldehydes50> 0.3mM, the IC of 2,4-dihydroxyacetophenone50>0.2mM.Compound 1,5-bis--(2,4-dihydroxy-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1, the tyrosinase inhibitory activity of 5-diketone is far longer than reaction raw materials 2,4-dihydroxyacetophenone and 3,4-4-dihydroxy benzaldehyde.
Although the present invention is open as above with preferred embodiment; but it is not limited to the present invention, any person skilled in the art, without departing from the spirit and scope of the present invention; all can do various changes and modification, therefore protection scope of the present invention should be with being as the criterion that claims are defined.
Claims (10)
1. a compound with tyrosinase inhibitory activity, it is characterised in that described compound is 1,5-bis--(2,4-dihydroxies
Base-phenyl)-3-(3,4-dihydroxy-phenyl)-pentane-1,5-diketone, its structural formula is:
2. the method preparing compound described in claim 1, it is characterised in that mainly comprise the steps that
(1) 3,4-4-dihydroxy benzaldehyde and 2,4-dihydroxyacetophenone under boric acid and ascorbic catalysis, with PEG400,
Ethylene glycol, ethanol or methanol are solvent, react 3～6 hours in 100～130 DEG C；
(2) reactant liquor ethyl acetate, dichloromethane, ether or chloroform etc. extract 3-5 time, and organic facies is concentrated to give dry
Sample；
(3) silicagel column on drying sample, eluant is with the dichloromethane of volume ratio 30:1 mixing: methanol；
(4) eluate sample that step (3) is collected is concentrated to give drying sample, then through Sephadex LH-20 gel filtration chromatography
Compound described in isolated.
Method the most according to claim 2, it is characterised in that mainly comprise the steps that
(1) 3,4-4-dihydroxy benzaldehyde and 2,4-dihydroxyacetophenone are under boric acid and ascorbic catalysis, with PEG400
React 6 hours for solvent 130 DEG C；3,4-4-dihydroxy benzaldehydes are 1:1 with the mol ratio of 2,4-dihydroxyacetophenone；
(2) reactant liquor is extracted with ethyl acetate 3 times, and organic facies is evaporated to be dried, and obtains drying sample；
(3) silicagel column on drying sample, eluant is with the dichloromethane of volume ratio 30:1 mixing: methanol；
(4) concentrated being dried of step (3) is collected eluate sample to obtain drying sample, through Sephadex LH-20 gel column layer
Analysis, eluant is with the methanol-water of volume ratio 7:1 mixing, collects eluent, and lamellae detects, and same stream deciliter also obtains
Product.
The most according to the method in claim 2 or 3, it is characterised in that step (3) described silicagel column be granularity be 200～300
Purpose silica gel.
5. the application process of compound described in claim 1.
6. compound described in claim 1 fruit and vegerable anti-enzymatic browning, prepare cosmetics, and preparation be used for preventing and treating melanin
The application process needing to suppress in the medicine of the disease of tyrosinase activity too much caused.
Method the most according to claim 6, it is characterised in that be not added with anti-enzymatic browning adjuvant, cosmetic formulations, pharmaceutical preparation
Adjuvant.
Method the most according to claim 6, it is characterised in that add anti-enzymatic browning adjuvant, cosmetic formulations, pharmaceutical preparation
One or more in adjuvant.
9. contain the cosmetics of compound described in claim 1.
10. contain compound described in claim 1 for preventing and needing for the treatment of that melanism causes suppresses tyrosinase activity
The medicine of disease.
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| US20140363388A1 (en) * | 2008-07-21 | 2014-12-11 | Unigen, Inc. | Series of skin whitening (lightening) compounds |
| CN104447269A (en) * | 2014-12-05 | 2015-03-25 | 江南大学 | Compound having tyrosinase inhibitory activity and synthesis method of compound |
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