CN102321144A - Method for extracting ursolic acid from red jujube - Google Patents
Method for extracting ursolic acid from red jujube Download PDFInfo
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- CN102321144A CN102321144A CN201110207264A CN201110207264A CN102321144A CN 102321144 A CN102321144 A CN 102321144A CN 201110207264 A CN201110207264 A CN 201110207264A CN 201110207264 A CN201110207264 A CN 201110207264A CN 102321144 A CN102321144 A CN 102321144A
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Abstract
The invention discloses a method for extracting ursolic acid from red jujubes, and is characterized in that the method comprises the following steps: cleaning and drying red jujubes, pulverizing the red jujubes, weighing red jujube dry powder, adding an ethanol aqueous solution with an amount of 20 times of the weight of the red jujubes as an extraction solvent; then, transferring the solution into a microwave reactor with a microwave control temperature being set at 60-80 DEG C, power of 200-400 W, microwave action time of 80-100 s, cooling, repeating the operations of microwave reaction and cooling for 1-10 cycles, centrifuging the extract, performing reduced-pressure filtration of the supernatant, collecting the filtrate, performing reduced-pressure distillation to obtain an ursolic acid extractum; finally, washing the extractum with distilled water and petroleum ether, filtering, dissolving the extractum with anhydrous ethanol, adding active carbon for decoloration, performing recrystallization, performing suction filtration to obtain the ursolic acid extract. The extraction method of the invention has high extraction efficiency, and the ursolic acid extract obtained by the extraction method of the invention has high product purity.
Description
Technical field
The present invention relates to a kind of natural product extraction method, in particular to a kind of method of from red date, extracting ursolic acid.
Background technology
(Ursolic Acid UA), has another name called ursonic acid, urson to ursolic acid, belongs to α-amyrin type pentacyclic triterpenoid.Purified ursolic acid is a white needle-like crystals, and fusing point is 285-287 ℃, is soluble in dioxane, pyridine, dissolves in methyl alcohol, ethanol, is slightly soluble in acetone, is slightly soluble in benzene, chloroform, ether.Mainly be distributed at the occurring in nature ursolic acid in the various plants such as Glossy Privet Fruit, hawthorn, Spica Prunellae, psyllium and Leaf of Chinese Holly, obtained in fields such as medicine, food, health care and makeup to use widely.
Ursolic acid has wide biological activity, especially antitumor, anti-oxidant, anti-bacteria and anti-virus, protect the liver and the effect of aspect such as beauty and skin care remarkable, significant.
Discover that ursolic acid has carcinogenesis, anti-promoting, induces differentiation of F9 teratocarcinoma cell and antineoplastic vascular formation effect.It is mainly through following several respects effect: ursolic acid ability mutation, the startup that suppresses canceration, ability direct killing tumour cell; Have cancer eliminating effect and anti-invasion property, inducing apoptosis of tumour cell and inhibition tumor vessel and form, thus the formation of inhibition canceration; And to the kinds of tumor cells body is inside and outside restraining effect is arranged all, and can reduce after the radiotherapy, chemotherapy infringement hemopoietic system.
Ursolic acid has restraining effect to various kinds of cell cordings such as colorectal carcinoma, melanoma and cancer of the stomach, and induces its apoptosis, and its mechanism possibly be to realize through the expression that influences cell cycle and cancer associated gene.Discover that like Yu Libo etc. ursolic acid can obviously suppress the ovarian cancer cell growth, and cell death inducing, its main mechanism is relevant with protein expression of adjusting Bc1-2 and Bax.
Oxygenizement is one of major reason that causes mankind aging's phenomenon, the oxidation of bad SUV (LDL) in preventing human body, and the rejuvenation aspect of maintenance blood vessel, ursolic acid is being played the part of important role.
Ursolic acid has tangible anti-oxidant function, thereby is widely used as medicine and cosmetic material.Antioxygenation all has active effect to flight against senium of human body and skin removing beverage, the pigment of dispelling, beauty treatment.Antioxygenation for ursolic acid has the people once to do research, finds that ursolic acid has tangible scavenging(action) to superoxide anion and hydroxy radical qiao, can reach 88.42% to the highest clearance rate of superoxide anion, but scavenging(action) is weaker than with the Vc under the concentration.Ursolic acid reaches as high as 86.35% to the scavenging(action) of hydroxy radical qiao, and is better than with the N.F,USP MANNITOL under the concentration, has tangible oxidation-resistance.Ursolic acid has the effect of protection diabetes rat blood vessel injury, and mechanism maybe be anti-oxidant with ursolic acid, thereby the activation that suppresses NF-kB is relevant.
Ursolic acid can cause cell viability to descend, and can suppress G
+And G
-Bacterium and inhibition fungal growth.To killing and suppressing the streptococcus mutans group and the periodontal pathogenic bacteria has a significant effect.Ursolic acid can suppress the HIV-1 protease activity, and raise immunity is brought into play the effect of anti-HIV.
Patent CN101543499 is to the serious problem of present streptococcus aureus resistance, and ursolic acid has been carried out antibacterial tests in external and the body.The particularly external Synergism Testing of in vitro tests; Finding has better antibacterial activity to the resistance streptococcus aureus under the acting in conjunction of itself and penicillium mould; Minimum inhibitory concentration is 1.13ug/disc, and in vivo tests shows that also ursolic acid also has activity preferably under synergy.
In addition, ursolic acid also has the antimalarial effect, and plasmodial propagation is obviously reduced.
Ursolic acid has the significant protection effect to the acute experiment liver damage, and clinical manifestation is that the decline of serum glutamic pyruvic transminase content, hepatocellular degeneration, necrosis obviously alleviate, and the effect of recovering liver function rapidly has the characteristics of instant effect, short treating period, effect stability.
Ursolic acid can effectively be treated viral hepatitis, is the main active ingredient of antiviral hepatitis medicine.In preparation treatment viral hepatitis medicine, no matter ursolic acid uses separately, still be used, as long as be prepared into medicine or health care medicine all has significant effect with other medicines.
The content of L-oxyproline increases along with the increase of ursolic acid dosage in the skin, and ursolic acid is for oral administration can to promote the synthetic of skin collagen, and the skin area rejuvenation is changed.Ursolic acid has water absorbability and humidity-preserving type, but with regard to humidity-preserving type, ursolic acid just can be used as the novel material of makeup.
The makeup that contain ursolic acid can slow down the aging and cooling blood for hemostasis of skin effectively, through the eliminating vivotoxin that stimulates circulation, can reach the effect of dispeling comedo and various spots.Enzyme that simultaneously can also activating cells keeps the physiologically active and the metabolism that promotes cell of epidermic cell, play the full nutrition skin and moment skin whitening effects.
Skunk bush meat can be as the good source of processing health food, and ursolic acid is main functional ingredient in skunk bush.But, since skunk bush to be used for the large-scale food-processing time shorter, difficulty of processing is bigger, relevant skunk bush protective foods seldom on the market.At present, mainly contain cornel wine, dogwood fruit drink, skunk bush jam, can etc.
The skunk bush Production of Healthy Wine has comparatively long history, generally is the skunk bush cold soaking is processed.The skunk bush health promoting wine is such just to special population unlike common medicinal liquor, and it is the low wine degree fruit wine with skunk bush unique perfume; Also contain functional ingredient such as meliatin, ursolic acid simultaneously, play function such as regulate body, delay senility, all-ages.
In addition, ursolic acid also has tangible radioprotective, calmness, antiulcer agent, atherosclerosis and various biological effects such as syngignoscism stable, that lower the temperature, work in coordination with Sodital.
Ursolic acid gets most of the attention with its wide biological activity, has attracted increasing research worker to get involved the research work of this respect.Patent CN101318985 discloses a kind of preparation method of ursolic acid and products thereof and has used.Ursolic acid mixed with Momordica-Glycosides, honey can be made into Grosvenor Momordica with health role honey cream.Made Grosvenor Momordica honey cream not only has the simple and elegant fragrance of the delicate fragrance of Momordica-Glycosides, sweet thick sense and honey; Mouthfeel is fresh and sweet; Mellow aromatic, and have the effect of calmness, clearing heat and moistening lung, ease constipation, defaecation, improvement sleep, be the high-quality healthcare products that integrate nutrition and health care.
Summary of the invention
In order to obtain natural ursolic acid extract, the present invention adopts following technical scheme:
One aspect of the present invention relates to a kind of method of from red date, extracting ursolic acid, it is characterized in that comprising the steps:
Red date is cleaned oven dry, pulverizes, and takes by weighing red date dry powder, adds 20 times of aqueous ethanolic solutions of red date quality again as extracting solvent;
Then, solution is moved into microwave reactor, setting the microwave controlled temperature and be 60-80 ℃, power is that 200-400W, microwave action time are 80-100s; Cooling then; Repeat microwave reaction and cooling operation 1-10 circulation then, extracting solution carries out centrifugal, then with the supernatant filtration under diminished pressure; Collect filtrating, the filtrate decompression distillation obtains ursolic acid medicinal extract;
At last, medicinal extract filters with zero(ppm) water and petroleum ether, uses anhydrous alcohol solution medicinal extract again, adds activated carbon decolorizing, recrystallization, and suction filtration obtains the ursolic acid extract.
In a preferred implementation of the present invention, it is characterized in that aqueous ethanolic solution is 80% aqueous ethanolic solution.
The invention still further relates to by the said extracted method and extract the ursolic acid extract that obtains.
The invention still further relates to the application of above-mentioned ursolic acid extract in preparation medicine, healthcare products or makeup, described medicine preferably is meant the medicine of antitumor drug, antibacterials, antiviral or treatment hepatitis; Described makeup preferably are meant to have anti-ageing, anti-oxidant and/or preserve moisture and attack the makeup of effect.
Adopt the resulting ursolic acid extract of process for extracting of the present invention extraction efficiency high, products obtained therefrom purity is high.
Description of drawings:
Fig. 1: the UV spectrum of standard substance;
Fig. 2: the UV spectrum of Fructus Jujubae extract.
Embodiment
Embodiment 1: at first, the red date that will land is cleaned, and dries to constant weight for 50 ℃, pulverizes 60 mesh sieves.Take by weighing the red date dry powder in flask, add 20 times of red date quality again, volume(tric)fraction is that 80% aqueous ethanolic solution (80mL absolute ethyl alcohol and 20mL zero(ppm) water dissolve each other) is as extracting solvent.
Then, flask is moved into microwave reactor, setting the microwave controlled temperature and be 70 ℃, power is that 300W, microwave action time are 90s, and fixed rotating speed stirs, and after the question response device stops, taking out flask normal temperature down behind the cooling 20min.Continuation is microwave reaction under the same settings condition, and each microwave action time of accumulative total reaches 90s.Extracting solution is pressed the centrifugal 20min of rotating speed 3000r/min, takes out centrifuge tube, in extraction supernatant impouring one container wherein, carries out filtration under diminished pressure then, collects filtrating.
Subsequently,, and reclaim ethanol, obtain ursolic acid medicinal extract the filtrate decompression distillation.
At last, medicinal extract is with distilled water wash 2 times, and petroleum ether 3 times is filtered.Use anhydrous alcohol solution medicinal extract again, add activated carbon decolorizing 2 times, recrystallization, suction filtration obtains the ursolic acid extract.
The Analysis and Identification of ursolic acid extract:
Precision takes by weighing ursolic acid standard substance 10mg, in the 100mL volumetric flask, promptly gets the ursolic acid standardized solution of 0.1mg/mL with the absolute ethyl alcohol constant volume.The accurate ursolic acid standardized solution 1.0mL that draws places tool plug test tube, after solvent is flung in heating, adds 5% Vanillin-Glacial acetic acid min. 99.5 0.3mL; Perchloric acid 0.7mL heats 15min in 60 ℃ of water-baths, moves to the 5mL tool after the taking-up cooling and refers in the test tube; The ETHYLE ACETATE constant volume; Shake up the back and measure absorbancy at the 548nm place, make reference with reagent blank simultaneously with ultraviolet spectrophotometer, as shown in Figure 1.
Precision takes by weighing ursolic acid extract 10mg, and method is the same, and the result is as shown in Figure 2.
Can know that by Fig. 1 the maximum absorption wavelength λ max of ursolic acid is near 548nm.Can be known that by Fig. 2 tangible uv-absorbing appears in the ursolic acid crystal at the 545nm place, the extract that can judge thus in the Loquat Leaf is a ursolic acid.
Through identifying, the yield that adopts the male fruit of process for extracting of the present invention to calculate is: 2.5-3.0mg/g; Purity: 80～90%
When being understood that, concerning those of ordinary skills, can improve or conversion, and all these improvement and conversion all should belong to the protection domain of accompanying claims of the present invention according to above-mentioned explanation.
Claims (6)
1. a method of from red date, extracting ursolic acid is characterized in that comprising the steps:
Red date is cleaned oven dry, pulverizes, and takes by weighing red date dry powder, adds 20 times of aqueous ethanolic solutions of red date quality again as extracting solvent;
Then, solution is moved into microwave reactor, setting the microwave controlled temperature and be 60-80 ℃, power is that 200-400W, microwave action time are 80-100s; Cooling then; Repeat microwave reaction and cooling operation 1-10 circulation then, extracting solution carries out centrifugal, then with the supernatant filtration under diminished pressure; Collect filtrating, the filtrate decompression distillation obtains ursolic acid medicinal extract;
At last, medicinal extract filters with zero(ppm) water and petroleum ether, uses anhydrous alcohol solution medicinal extract again, adds activated carbon decolorizing, recrystallization, and suction filtration obtains the ursolic acid extract.
2. process for extracting according to claim 1 is characterized in that aqueous ethanolic solution is 80% aqueous ethanolic solution.
3. process for extracting according to claim 1 and 2 extracts the ursolic acid extract that obtains.
4. the application of ursolic acid extract according to claim 3 in preparation medicine, healthcare products or makeup.
5. application according to claim 4 is characterized in that described medicine is meant the medicine of antitumor drug, antibacterials, antiviral or treatment hepatitis.
6. application according to claim 4 is characterized in that described makeup are meant to have anti-ageing, anti-oxidant and/or preserve moisture and attack the makeup of effect.
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| CN201110207264A CN102321144A (en) | 2011-07-25 | 2011-07-25 | Method for extracting ursolic acid from red jujube |
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| CN201110207264A CN102321144A (en) | 2011-07-25 | 2011-07-25 | Method for extracting ursolic acid from red jujube |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104188984A (en) * | 2014-08-11 | 2014-12-10 | 南京广康协生物医药技术有限公司 | Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of antibacterial drugs |
| CN106977977A (en) * | 2017-04-01 | 2017-07-25 | 重庆大学 | A kind of method for synthesizing gardenia blue pigment |
| CN106983769A (en) * | 2016-01-21 | 2017-07-28 | 易以木 | For radiation-resistant ursolic acid Chinese yam polysaccharide composition and preparation method thereof |
| CN106983810A (en) * | 2016-01-21 | 2017-07-28 | 易以木 | Chinese yam polysaccharide, loquat-leaf extract radioresistance oral formulations and preparation method |
| CN108690115A (en) * | 2018-05-28 | 2018-10-23 | 吉林农业科技学院 | The Microwave Extraction technique of ursolic acid in a kind of Asiatic plantain |
| CN109172432A (en) * | 2018-09-27 | 2019-01-11 | 广州航美化妆品有限公司 | Moisturizing remediation composition and its application |
-
2011
- 2011-07-25 CN CN201110207264A patent/CN102321144A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 《化工科技》 20101231 吕佳飞 等 红枣中熊果酸的微波提取工艺研究 第33-36页 1-6 第18卷, 第3期 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104188984A (en) * | 2014-08-11 | 2014-12-10 | 南京广康协生物医药技术有限公司 | Application of Cleistanone O-(morpholinyl)ethyl derivative in preparation of antibacterial drugs |
| CN106983769A (en) * | 2016-01-21 | 2017-07-28 | 易以木 | For radiation-resistant ursolic acid Chinese yam polysaccharide composition and preparation method thereof |
| CN106983810A (en) * | 2016-01-21 | 2017-07-28 | 易以木 | Chinese yam polysaccharide, loquat-leaf extract radioresistance oral formulations and preparation method |
| CN106977977A (en) * | 2017-04-01 | 2017-07-25 | 重庆大学 | A kind of method for synthesizing gardenia blue pigment |
| CN108690115A (en) * | 2018-05-28 | 2018-10-23 | 吉林农业科技学院 | The Microwave Extraction technique of ursolic acid in a kind of Asiatic plantain |
| CN109172432A (en) * | 2018-09-27 | 2019-01-11 | 广州航美化妆品有限公司 | Moisturizing remediation composition and its application |
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Application publication date: 20120118 |