CN103159621B - Stilbene active component, preparation method and application thereof - Google Patents
Stilbene active component, preparation method and application thereof Download PDFInfo
- Publication number
- CN103159621B CN103159621B CN201110423178.3A CN201110423178A CN103159621B CN 103159621 B CN103159621 B CN 103159621B CN 201110423178 A CN201110423178 A CN 201110423178A CN 103159621 B CN103159621 B CN 103159621B
- Authority
- CN
- China
- Prior art keywords
- stilbene
- active component
- hydroxyl
- preparation
- pigeon pea
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a novel stilbene active component: 12-hydroxy pigeonpea stilbene acid extracted and purified from pigeonpea leaves, an extraction and purification method and an application thereof. A compound structure is as shown in graph 1. Technical solutions adopted comprises using the pigeonpea leaves as raw materials, extracting with a solvent, condensing the extract till drying, performing ultrasonic vibration for flocculation, dispersing in water, and then using a negative pressure cavitation suspension solid extraction technology, a macroporous adsorption resin enrichment technology and a normal phase silica gel medium pressure column chromatography technology, together with a low temperature crystallization and re-crystallization technology to obtain the component with a purity of more than 95 %. Through a DPPH model and an MTT method, antioxidant activity and anti-tumor activity of the chemical components are detected, and results show that the active component has good radical scavenging activity and anti-tumor activity in vitro. A preparation method of the 12-hydroxy pigeonpea stilbene acid is simple, easy to operate, high in product yield, purity and added value, and suitable for industrial production and application, and can be further developed as novel anti-oxidants and antitumor drugs.
Description
Technical field
The present invention relates to a kind of from plant extracting and developing purifying there is a kind of method of bioactive compound, belong to natural product field.Specifically a kind of new stilbene compound of extracting and developing purifying from pigeonpea [Cajanus cajan L.Millsp.] leaf.This compound 12-hydroxyl pigeon pea stilbene acid, chemistry is by name: 3,12-dihydroxy is-4-prenyl-5-methoxyl group stilbene-2-carboxylic acid very.
Background technology
Pigeonpea [Cajanus cajan L.Millsp.], for Phaseoleae (Phaseoleae) pulse family (Leguminosae), Papillionoideae (Papilionaceae), pigeonpea belong to (Cajanus) annual or perennial brushwood, it is a woody raise crop unique during pigeonpea belongs to, because its beanpod is tied on tree crown branch, therefore claiming pigeonpea, another name pigeon beans, soya bean tree, fine bean mash tree, kwan-yin beans, Semen Phaseoli, large pigeonpea, Russian red clover, flower spiral shell are set beans, beans in thousand, are set beans, Rong's beans, Liu Dou, Hua Dou, meter Dou etc.
Pigeonpea Medicinal is with a long history, Morton and Duke summarizes pigeonpea in many Afro-Asian folk medicine application such as China, India, Argentina, and wherein the leaf of pigeonpea is used for treating bedsore, vesical calculus, jaundice, dysentery, toothache and genital system infection; Its flower is used for bronchitis, cough, pneumonia (Morton J.F., 1976; Duke J.A., 1981).Record according to " Luchuan book on Chinese herbal medicine ", Leaf of Cajan nature and flavor are flat, light, slightly poisonous, have and separate acne poison, the effects such as anti-inflammatory is swollen.Can control chickenpox in children, carbuncle swells.This plant also has medicinal elaboration in the multiple local medicine will of China, as clearing heat and detoxicating in just recorded pigeonpea in " Quanzhou book on Chinese herbal medicine ", and invigorating the spleen and replenishing QI, Li Shui helps digestion, and row's carbuncle swells, hemostasis and dysentery-stopping, and evident in efficacy.In recent years, Hainan the People's Hospital, based on medication experience among the people, treats wound, burn infection and bedsore etc. with Leaf of Cajan and achieves good curative effect.
At present, extensive to pigeonpea biologic activity content research both at home and abroad, confirm that Semen Cajani extract and chemical composition thereof can treat the bone related disease such as osteoporosis, necrosis of femoral head by zoology model and Cell. Mol means, have hypoglycemic and blood fat, anti-cerebral ischemia anoxia-induced apoptosis, anti-oxidant, protect the liver, anti-inflammatory, anti-malarial, antibacterial] and the physiologically active such as anti-sickle anemia.But the research such as effective constituent, the mechanism of action is clear not enough, limit its application clinically.Both at home and abroad about in the report of Leaf of Cajan, 12-hydroxyl pigeon pea stilbene acid has no report.
Summary of the invention
New stilbene compound (12-hydroxyl pigeon pea stilbene acid) that the object of the present invention is to provide a kind of extraction and isolation from Leaf of Cajan and preparation method thereof.This composition has antioxidation in vitro and anti-tumor activity.The preparation method of this new compound: fresh or dry leave is raw material with pigeonpea, Leaf of Cajan is pulverized rear solvent extraction, extracting solution is concentrated into dry, then ultra-sonic oscillation are flocculated, are left standstill, gained throw out carries out negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction, macroporous adsorbing resin for purification and purification on normal-phase silica gel medium pressure column chromatography, again in conjunction with low temperature crystallization and recrystallization technology, the described new stilbene compound of a large amount of acquisition.The method is simple, quick, target compound loss is less.New stilbene class active compound provided by the invention---12-hydroxyl pigeon pea stilbene acid is obtained by following scheme:
(1) or dry leave fresh with pigeonpea is raw material, Leaf of Cajan is pulverized rear solvent extraction, extracting method used comprises the extractive techniques such as immersion, thermal backflow, negative pressure cavitation and ultrasonic-assisted extraction, the solvent adopted is chloroform, ethyl acetate, acetone, methyl alcohol, ethanol or alcohol water mixed system, obtains crude extract after extracting solution recycling design.
(2) extract the crude extract obtained, add the warm water of 5 ~ 10 times of quality 40 ~ 60 DEG C, ultra-sonic oscillation 10 ~ 30min under 40 ~ 60KHz condition, leave standstill 15 ~ 20min, obtain the throw out being rich in this stilbene compound.
(3) ultrasonic oscillation flocculates the throw out obtained, the one in ethyl acetate, trichloromethane or methylene dichloride is added with the amount of 10 ~ 15mL/g throw out, then with 0.01 ~ 0.07MPa negative pressure for power carries out negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction, continue 5 ~ 15min, extract 2 ~ 4 times, extraction liquid is concentrated into dry, obtains target compound crude product.
(4) it is 40 ~ 60mg/mL suspension that solid substance part negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction obtained is mixed with feed concentration with 30 ~ 40% ethanolic solns, adopted by macroporous adsorbent resin wet method to fill post simultaneously, retain liquid level, suspension is passed through AB-8, NKA-9, HPD-800, the one of D101 adsorption column, applied sample amount is 1.0 ~ 3.5BV, with flow velocity 2 ~ 4BV/h, PH=4 condition descended adsorption column, impurity is washed away with 30 ~ 40% ethanol 3BV after absorption, then 50 ~ 80% ethanol 4 ~ 8BV desorbs are used, collect stripping liquid, be concentrated into dry, gained solid substance is target compound.
(5) after being resolved by resin, gained solid substance 200 ~ 800 order purification on normal-phase silica gel carry out purification on normal-phase silica gel medium pressure column chromatography, moving phase be a kind of in sherwood oil or normal hexane with the one in methylene dichloride, trichloromethane, ethyl acetate or acetone according to volume ratio 5: 1 ~ 50: 1 mixed system.Again in conjunction with crystallization and recrystallization technology, obtain purity and be greater than 95% target component monomer.Crystallization and recrystallization solvent for use be a kind of in sherwood oil or normal hexane with the one in methylene dichloride, trichloromethane, ethyl acetate, acetone or methyl alcohol according to volume ratio 15: 1 ~ 1: 1 mixed system.
The activeconstituents composition of gained of the present invention, through the modern physical means such as UV, IR, MS, 1HNMR and 13CNMR and chemical process determination structure, is shown in Fig. 1.This compound name is called: 3,12-dihydroxyl-4-prenyl-5-methoxyl group stilbene-2-carboxylic acid.Close with pigeon pea stilbene acid structure because of it, by its called after: 12-hydroxyl pigeon pea stilbene acid.
This compound is colourless prism, and ferric chloride reaction presents green (containing phenolic hydroxyl group), and the vitriol oil/ethanolic soln reacting by heating has aromatic odour to produce (containing carboxyl).Ultra-violet absorption spectrum (Fig. 2) shows in this compound and there is conjugated chromophore.Infrared spectra (Fig. 3) shows this compound and contains hydroxyl, phenyl ring, α, β unsaturated acid.High resolution mass spectrum HR-ESI-MS analyzes and obtains its molecular weight is 354.2242, determines that molecular formula is C
21h
22o
5.As shown in Figure 4, ESI-MS m/z 353.4M-H]-, 377.6 [M+H]
+, 731.8 [2M+Na]
+, the secondary negative ion mass spectrum analysis of m/z 353.4 provide 309 [M-44]-, 239 [M-44-70]-, 335 [M-H2O]-, 293 [M-60]-, its cracking rule is similar to pigeon pea stilbene acid.
The 1D-NMR spectrum of this compound is as Fig. 5, shown in 6, 1H NMR (500MHz, DMSO-d6) spectrum provides 3 methyl signals δ 3.83 (s, 3H), 1.63 (s, 3H) He 1.50 (s, 3H), 1 methylene signals δ 3.17 (2H), 1 olefinic proton signal 4.88 (d, J=26.9Hz, 1H), total score minor, 1H-NMR, 13C-NMR data and compound L ongistyline C (C.J.Cooksey, 1982), pigeon pea stilbene acid (P.W.Green, 2003), 3-hydroxy-5-methoxystilbene-2-carboxylic acid (Y.Ohwaki, 1993) and Verakanol derivative (D.Koh, 2001) relevant spectrogram compares, infer that this compound is stilbene class material.1H NMR(500MHz，DMSO-d6)：δ8.04(br s，2H，H-7，H-8)，7.60-7.45(m，4H，H-10，H-11，H-13，H-14)，6.51(s，1H，H-6)，4.88(t，1H，H-2′)，4.67(br s，1H，12-OH)，3.83(s，3H，-OCH3)，3.17(d，J＝5.2Hz，2H，H-1′)，1.63(s，3H，H-5′)，1.50(s，3H，H-4′)。13C NMR(125MHz，DMSO-d6)：δ173.2(-COOH)，170.0(C-5)，161.8(C-3)，142.8(C-12)，137.6(C-1)，133.7(C-3′)，131.4(C-8)，130.8(C-9)，129.1(C-10，C-14)，128.3(C-7)，125.9(C-2′)，123.4(C-4)，122.6(C-13)，121.9(C-11)，107.3(C-2)，98.6(C-6)，56.30(-OCH3)，25.8(C-4′)，24.9(C-1′)，18.0(C-5′)。Compared with compound pigeon pea stilbene acid, at H chemical shift 4.67 (br s, 1H, 12-OH) different, its NMR spectrogram shows isoprene group equally to be existed, but 7.60-7.45 (m, 4H, H-10, H-11, H-13, H-14) show that the phenyl ring of this compound is monosubstituted, therefore determine that this compound is 3,12-dihydroxyl-4-prenyl-5-methoxyl group stilbene-2-carboxylic acid (3,12-dihydroxy-4-prenyl-5-methoxystilbene-2-carboxylic acid), compare with compound pigeon pea stilbene acid, called after 12-hydroxyl pigeon pea stilbene acid.
12-hydroxyl pigeon pea stilbene acid in the present invention detects its anti-oxidant activity and anti-tumor activity respectively by DPPH model and MTT (tetrazolium bromide) method.Its activity (IC in DPPH model
50160.33 ± 2.92 μ g/m1) stronger than positive control medicine xitix, and suppress the IC of human breast cancer cell (MCF-7), human lung adenocarcinoma cell (A549) and human liver cancer cell (HepG2)
50value is respectively 10.13,12.01 and 12.78 μ g/mL, is better than contrasting trans-resveratrol.Result shows that this activeconstituents has good free radical scavenging activity and anti tumor activity in vitro.
Accompanying drawing explanation
The structural formula of Fig. 1: 12-hydroxyl pigeon pea stilbene acid
The UV spectrum of Fig. 2: 12-hydroxyl pigeon pea stilbene acid
The infrared spectra of Fig. 3: 12-hydroxyl pigeon pea stilbene acid.
The ESI-MS spectrum of Fig. 4: 12-hydroxyl pigeon pea stilbene acid
Wherein, A is that the first mass spectrometric TIC of gained compound under negative ion scan pattern schemes, 353.4 [M-H]-and be molecular ion peak; B is the second order ms figure of gained compound under negative ion scan pattern, shows the corresponding molecular fragment of this compound in figure
The 1H-NMR spectrum of Fig. 5: 12-hydroxyl pigeon pea stilbene acid
The 13C-NMR spectrum of Fig. 6: 12-hydroxyl pigeon pea stilbene acid
Embodiment
The separation of stilbene class active compound new in embodiment 1. Leaf of Cajan
Take the 3.0kg of pigeonpea cured leaf, by 80% EtOH Sonicate ripple assisted extraction 2 hours, extract 3 times.Extracting solution merges, be concentrated into after doing, add in 4 liters of 60 DEG C of warm water, vibration flocculation 25min under 40KHz condition in ultrasonic extractor, leave standstill 20mm, get thickness throw out, ethyl acetate is added with the amount of 12mL/g throw out, one in trichloromethane or methylene dichloride, with 0.03MPa negative pressure for power carries out negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction, continue 15min, extract 3 times, extraction liquid is concentrated into dry, it is 55mg/mL suspension that the solid substance obtained is mixed with feed concentration with 40% ethanolic soln, applied sample amount is 2.5BV, at flow velocity 3BV/h, PH=4 condition descended AB-8 type macroporous adsorptive resins, impurity is washed away with 40% ethanol 3BV after absorption, then 80% ethanol 6BV desorb is used, collect stripping liquid, be concentrated into after doing and dissolve with a small amount of anhydrous methanol, adding 100g order number is that 300 ~ 400 silica gel are mixed thoroughly, evaporated under reduced pressure.Take 500 ~ 800 order silica gel of extract quality 9 times in advance, adopt normal hexane wet method dress post, during the silica gel having mixed sample is loaded in compression leg, successively with normal hexane: trichloromethane (10: 1), normal hexane: compress and wash de-during trichloromethane (5: 1), trichloromethane are continuous, the flow point being rich in target compound is collected in TLC monitoring, after concentrated, low temperature crystallization obtains product, then obtains target compound 46.8mg after carrying out recrystallization, and purity is 95.8%.
Embodiment 2.DPPH free radical scavenging activity measures
DPPH is dissolved in dehydrated alcohol and is made into 0.004% solution.The xitix reference substance solution of the sample solution of 0.1mL different concns and 0.1mL different concns is added in the DPPH solution of 1mL respectively, rapid mixing, and then add 1.4mL dehydrated alcohol, after 70min, be placed in ultraviolet spectrophotometer, take blank solvent as contrast, under 517nm wavelength, measure the absorbancy of solution.Take xitix as positive control, the ability with formulae discovery sample scavenging free radicals below:
Resistance of oxidation (Ip)=[(AB-AA)/AB] × 100
In formula: blank and treat the absorbancy of test sample after AB, AA are respectively 70min.
Experimental result statistical treatment calculates the IC of free radical scavenging activity
50value.Result shows 12-hydroxyl pigeon pea stilbene acid (IC
50160.33 ± 2.92 μ g/ml) DPPH free radical scavenging activity is better than positive control xitix (IC
50194.18 ± 3.82 μ g/ml).
Embodiment 3.MTT (tetrazolium bromide) method antitumor cytolytic activity
(1) cell cultures: collect the tumour cell being in logarithmic phase, single cell suspension is become with 0.25% tryptic digestion, being diluted to cell concn with the RPMI1640 nutrient solution containing 10% foetal calf serum is 2 × 104/mL (viable cell>=95%), be inoculated in 96 orifice plates with every hole 200 μ L, be placed in 37 DEG C, 5%CO
2, saturated humidity CO
224h is cultivated in incubator.
(2) add medicine: dissolved by medicine DMSO, add in 96 orifice plates according to the medicine of experimental design, be diluted to the different operating concentration of setting with RPMI1640 cell maintenance medium.Be negative control with the equivalent DMSO of not drug containing, do not add the equivalent medicine of enchylema for blank.After adding medicine, be placed in 37 DEG C, 5%CO
2, saturated humidity CO
272h is cultivated in incubator.
(3) MTT is added: be made into the solution that concentration is 5mg/mL, 0.22 μm of filtration sterilization by getting MTT serum-free RPMI1640 nutrient solution.After adding medicine cultivation, every hole adds MTT solution 20 μ L, is placed in 37 DEG C, 5%CO
2, saturated humidity CO
2continue in incubator to hatch 4h.Stop cultivating, inhale and abandon supernatant liquor in hole, after throw out nutrient solution washs 3 times, every hole adds 100 μ L DMSO vibrations makes it abundant dissolving.Microplate reader measures each hole OD
570value.
(4) data calculate: the inhibiting rate calculating drug on tumor cell according to the following equation,
Draw dose effect curve according to inhibiting rate and drug level relation, Logit method calculates medicine to the minimum lethal dose of culturing cell: medication makes viable cell quantity reduce the drug level of a half, i.e. half-inhibition concentration (IC
50).In triplicate, data represent with mean+SD in experiment.
Table 112-hydroxyl pigeon pea stilbene acid anti tumor activity in vitro
From the above results, the activity (IC in 12-hydroxyl pigeon pea stilbene acid DPPH model
50160.33 ± 2.92 μ g/ml) stronger than positive control medicine xitix, and suppress the IC of human breast cancer cell (MCF-7), human lung adenocarcinoma cell (A549) and human liver cancer cell (HepG2)
50value is respectively 10.13,12.01 and 12.78 μ g/mL, is better than contrasting trans-resveratrol.Above result shows that this activeconstituents has good free radical scavenging activity and anti tumor activity in vitro, can develop further as novel antioxidant and antitumor drug.
Claims (7)
1. the preparation method of a stilbene active component 12-hydroxyl pigeon pea stilbene acid, it is characterized in that: with pigeonpea, fresh or dry leave is raw material, Leaf of Cajan is pulverized rear solvent extraction, extracting solution is concentrated into dry, then ultra-sonic oscillation are flocculated, are left standstill, gained throw out carries out negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction, macroporous adsorbing resin for purification and purification on normal-phase silica gel medium pressure column chromatography, then obtains described stilbene active component 12-hydroxyl pigeon pea stilbene acid in conjunction with low temperature crystallization and recrystallization technology, and its structural formula is as figure below:
2. according to the preparation method of stilbene active component 12-hydroxyl pigeon pea stilbene acid according to claim 1, it is characterized in that: described extracting method comprises immersion, thermal backflow, negative pressure cavitation and ultrasonic-assisted extraction technology, described solvent is chloroform, ethyl acetate, acetone, methyl alcohol, ethanol or alcohol water mixed system.
3. according to the preparation method of stilbene active component 12-hydroxyl pigeon pea stilbene acid according to claim 1, it is characterized in that: 5 ~ 10 times of described ultra-sonic oscillation flocculation technique to be the amount adding 40 ~ 60 DEG C of warm water in Leaf of Cajan extract be extract quality, ultra-sonic oscillation flocculation time is 10 ~ 30min, frequency is 40 ~ 60KHz, and time of repose is 15 ~ 20min.
4. according to the preparation method of stilbene active component 12-hydroxyl pigeon pea stilbene acid according to claim 1, it is characterized in that: described negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction technology take negative pressure as power, utilize the cavitation effect that bubble produces, turbulence effect carries out forced fluid solid extraction to the ultra-sonic oscillation throw out obtained that flocculates, solvent for use is ethyl acetate, trichloromethane or methylene dichloride, extracting solvent volume used is 10 ~ 15mL/g throw out, pressure used is 0.01 ~ 0.07MPa, time length is 5 ~ 15min, extraction times is 2 ~ 4 times, after recovery organic phase solvent, gained solid substance is target compound crude product.
5. according to the preparation method of stilbene active component 12-hydroxyl pigeon pea stilbene acid according to claim 1, it is characterized in that: described macroporous adsorbing resin for purification method resin used comprises AB-8, NKA-9, HPD-800, one in D101 polymeric adsorbent, in the method, macroporous resin adsorption step adopts wet method dress post, retain liquid level, it is 40 ~ 60mg/mL suspension that solid substance part negative pressure-cavitation homogenous solid-liquid phase liquid-solid extraction obtained is mixed with feed concentration with 30 ~ 40% ethanolic solns, applied sample amount is 1.0 ~ 3.5BV, with flow velocity 2 ~ 4BV/h, pH=4 condition descended adsorption column, impurity is washed with 30 ~ 40% ethanol 3BV after absorption, then 50 ~ 80% ethanol 4 ~ 8BV desorbs are used, collect stripping liquid, be concentrated into dry, gained solid substance is target compound.
6. according to the preparation method of stilbene active component 12-hydroxyl pigeon pea stilbene acid according to claim 1, it is characterized in that: described purification on normal-phase silica gel medium pressure column chromatography with the solid substance obtained after macroporous adsorbing resin for purification for sample separation, used silica gel is 200 ~ 800 orders, used silica gel amount is 8 ~ 10 times of sample quality, moving phase used be a kind of in sherwood oil or normal hexane with the one in methylene dichloride, trichloromethane, ethyl acetate or acetone according to volume ratio 5:1 ~ 50:1 mixed system.
7., according to the preparation method of stilbene active component 12-hydroxyl pigeon pea stilbene acid according to claim 1, it is characterized in that: described recrystallization technology solvent used be a kind of in sherwood oil or normal hexane with the one in methylene dichloride, trichloromethane, ethyl acetate or acetone according to volume ratio 15:1 ~ 1:1 mixed system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110423178.3A CN103159621B (en) | 2011-12-16 | 2011-12-16 | Stilbene active component, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110423178.3A CN103159621B (en) | 2011-12-16 | 2011-12-16 | Stilbene active component, preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103159621A CN103159621A (en) | 2013-06-19 |
| CN103159621B true CN103159621B (en) | 2015-04-15 |
Family
ID=48583190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110423178.3A Active CN103159621B (en) | 2011-12-16 | 2011-12-16 | Stilbene active component, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103159621B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101172948A (en) * | 2007-11-01 | 2008-05-07 | 东北林业大学 | Method for separation and purification of cajanine and pinostrobin from extract of cajanus cajan branches and leaves |
| CN101569654A (en) * | 2009-06-09 | 2009-11-04 | 东北林业大学 | Supercritical extract of pigeon pea leaves and application of pigeon pea stilbene acid in the preparation of antitumor drug |
-
2011
- 2011-12-16 CN CN201110423178.3A patent/CN103159621B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101172948A (en) * | 2007-11-01 | 2008-05-07 | 东北林业大学 | Method for separation and purification of cajanine and pinostrobin from extract of cajanus cajan branches and leaves |
| CN101569654A (en) * | 2009-06-09 | 2009-11-04 | 东北林业大学 | Supercritical extract of pigeon pea leaves and application of pigeon pea stilbene acid in the preparation of antitumor drug |
Non-Patent Citations (1)
| Title |
|---|
| 木豆有效成分时空变化、高效提取及抗氧化活性研究;佟美鸿;《中国优秀硕士学位论文全文数据库 医药卫生科技辑》;20091115(第11期);摘要倒数第5-10行 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103159621A (en) | 2013-06-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Chen et al. | Caffeoylquinic acid derivatives isolated from the aerial parts of Gynura divaricata and their yeast α-glucosidase and PTP1B inhibitory activity | |
| Huang et al. | The cytotoxicity of 8-O-4′ neolignans from the seeds of Crataegus pinnatifida | |
| KR102413705B1 (en) | Composition for improving liver function comprising Dendropanax morbifera extract | |
| CN104861015A (en) | Synergistic clean extraction method of effective components in licorice root | |
| Oshima et al. | Quantitative analysis of the anti-inflammatory activity of orengedokuto II: berberine is responsible for the inhibition of NO production | |
| CN108997296B (en) | Structures and uses of several isopentenyl dihydro stilbenes and isopentenyl flavones | |
| Wang et al. | Characterization and biological evaluation of six new dimeric lignans with an unusual α, β-unsaturated ketone motif from Zanthoxylum simulans | |
| CN102031116A (en) | New method for preparing rosemary natural antioxidant | |
| CN103626824A (en) | Hemsleya amabilis cucurbitane tetracyclic triterpene compound, pharmaceutical composition comprising compound and application of pharmaceutical composition and compound | |
| CN102614156A (en) | Medical application of in-vivo metabolite of paeonol | |
| Kawazu et al. | Piscicidal Constituents of Calophyllum Inophyllum (Commemoration Issue Dedicated to Professor Minoru Ohno On the Occasion of his Retirement) | |
| CN103159621B (en) | Stilbene active component, preparation method and application thereof | |
| Sim et al. | Cratoxylum glaucum and Cratoxylum arborescens (Guttiferae)-two potential source of antioxidant agents | |
| CN104016955A (en) | Method for extracting myricetin by hovenia dulcis thunb | |
| Ren et al. | Four new phenolic compounds from the tender leaves of Eucommia ulmoides Oliv. and their anti-inflammatory activities | |
| CN101619054B (en) | New coumarin active content, preparation method and application thereof | |
| CN103191143B (en) | New application of cardiac glycoside compound | |
| CN105362785A (en) | Medicine composition for treating primary hypertension and preparation method thereof | |
| CN107383129A (en) | A kind of tonka bean camphor glycosides compounds and its preparation method and application | |
| Zou et al. | Sweritranslactone D, a hepatoprotective novel secoiridoid dimer with tetracyclic lactone skeleton from heat-transformed swertiamarin | |
| CN113248483A (en) | Preparation method and application of lawn pennywort herb flavone glycoside monomer isovitexin | |
| CN109276637B (en) | Semen allii tuberosi extract, preparation method thereof and application thereof in preparing liver-protecting medicine | |
| Wufuer et al. | Liglaurates A–E, cytotoxic bis (lauric acid-12yl) lignanoates from the rhizomes of Drynaria roosii Nakaike | |
| CN109091602B (en) | Effective component of semen allii tuberosi, extraction method and application thereof in preparing liver injury protection medicine | |
| CN107028842B (en) | Extraction method of active site of rose dregs and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |