CN102993151B - Flavanol compound, and preparation method and application thereof - Google Patents
Flavanol compound, and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a natural medicine, and particularly relates to novel flavanol compound in a Uraria clarkei, and a preparation method and application thereof. The invention provides the flavanol compound, and the preparation method and application thereof. The flavanol compound is separated and prepared from the Uraria clarkei. The structural formula of the compound is a formula (I) shown in the specification. The preparation method of the compound in the formula (I) comprises the steps of a, crushing; b, extracting by refluxing; c, concentrating; d, extracting, and e, separating. The compound in the formula (I) prepared by the preparation method provided by the invention has significant anti-cancer activity and activity of resisting marine fouling organisms, has obvious inhibition effect on cells of tumors, human cervical carcinoma, human chronic myeloid leukemia or human acute myelogenous leukemia, has good antitumor activity and good application prospect, also displays strong activity of inhibiting biofouling, and can provide valuable pilot compounds for development of an anti-fouling paint or other anti-fouling products.
Description
Technical field
The present invention relates to a kind of natural drug, be specifically related to a kind of new flavanols compounds and its preparation method and application in wild kind beans.
Background technology
Cancer has developed into common disease, the frequently-occurring disease of serious harm people life, and same cardiovascular and cerebrovascular disease, diabetes are called as one of the world three large Deaths together.The World Health Organization issued and reports in February, 2010, the whole world will have 7,600,000 people to die from cancer to estimate the current year, if the half-hearted preventing cancer of taking measures of people may be doubled to the annual cancer mortality number in the year two thousand thirty whole world on existing basis, reach 1,700 ten thousand.This tissue statistic data also shows in average every 8 deaths in the whole world, just have 1 people to die from cancer at present, and the death toll summation that this causes than acquired immune deficiency syndrome (AIDS), tuberculosis and malaria is taller.Therefore finding effective cancer therapy drug has become the task of top priority.In cancer therapy drug research, the studies and clinical application of chemotherapeutics has been obtained remarkable progress.As metal complexes platinum complex, organic germanium compounds etc., although have strong cancer resistance, there is toxic side effect, the defects such as poorly water-soluble in the cancer therapy drug of chemosynthesis.In recent years, the researchist of China and foreign countries turns one's attention to herbal medicine, the ethnic drug of aboundresources, pure natural gradually, wishes therefrom to find new cancer therapy drug.From herbal medicine, ethnic drug, find at present a series of natural anti-cancer drugs such as taxol, camptothecine, kind of harringtonine as medicinal materials, vincristine(VCR), podophyllotoxin, Elemenum Emulsion, and had every year many new product listings.These natural drugs have all showed good antitumour activity and have been widely used clinically, also day by day prove that screening antineoplastic drugs is a very promising direction from natural product.
Wild kind beans (
uraria clarkeigagnep) be pulse family (Leguminosae) leopard cat tail bean plant (72 pages of < < Chinese Plants will > > the 41st volumes).This platymiscium whole world approximately has 20 kinds, is distributed in Tropical Africa, Asia and Australia, and China has 9 kinds, and most kinds concentrate on north latitude 25° areas to the south.According to document, (Chen Yan, thinks the elegant tinkling of pieces of jade, Wei Song, Xu Xuejian.The research [J] of rabbit tail grass chemical composition. Chinese patent medicine, 2009,31 (2): 266-269) report, this platymiscium has the effects such as treatment infantile malnutrition, puerperal lactation deficiency, hemoptysis, hemorrhoid, the tuberculosis of cervical lymph nodes, venomous snake bite.The result of study of this platymiscium shows that its chemical composition is mainly flavonoid compound, comprises the structure types such as flavones, isoflavones, isoflavanone.Less to the research report of wild kind beans plant chemical ingredient and pharmacologically active at present.
Biodeterioration, refer to that marine organisms are gathered in any position of hull as algae, crustaceans etc., comprise shell, rudder, water screw and other hull attachments, or ship maritime interior waters system is as sea chest, engine cool pipeline, boat-carrying and auxiliary facility, or the biogenic accumulation and the fouling that on the movement such as aquaculture facility or fixation means, form.In recent years, along with the development of shipping, coast defence, aquaculture and coastal power plant etc., halobiontic stained brought harm is more and more serious.Develop at present the most soon, the pollution control damage method being most widely used is for applying high-efficiency pollution-proof paint.Generally adopt the antifouling paint that contains toxic chemical (as Red copper oxide, copper pyrithione, Irgarol 1051, Econea etc.) to prevent and kill off, but these toxic substances continue to discharge to ocean environment, particularly at ship movable intensive naval port and civil harbor, poisonous substance often reaches high level, causes serious marine pollution matter.Red copper oxide is a kind of stain control agent being most widely used at present, it has antifouling activity to most animal class marine lifes and most plant marine lifes, but not good to soft stained marine life anti-fouling effect, need to add auxiliary stain control agent and reach comprehensive anti-fouling effect.Because copper can especially gather in a large number in harbour in ocean, produce " black pollution ".Red copper oxide decomposes the cupric ion producing in seawater, and the apoenzyme that can make marine life depend on for existence loses activity, or makes the flocculation of biomass cells protein produce metalloprotein throw out, causes biological tissue to change and death.
Traditional stain control agent has toxic action to settled organism, causes expendable damage, and pollutes the environment, and destroy the eubiosis, and desirable marine antifoulant should meet simultaneously: under (1) lower concentration, have activity; (2) economy; (3) harmless to human body and other organism; (4) be applicable to various attaching substratums; (5) pollution-free; (6) there is biodegradability.Natural product stain control agent in bionical antifouling paint or its analogue through chemical modification, easily degraded, and do not endanger biological life, and be conducive to keep ecological balance, be one of important channel of exploitation non-toxic efficient antifouling paint.Many materials with anti-fouling activity from ocean and terrestrial life, have been found at present, the material that comprises the types such as terpene, alkynes class, polynuclear compound, steroide, isothiocyanate, part of compounds has wherein shown good repellency to marine fouling organism, but lower or be safe from harm to the harm of water body environment.
Summary of the invention
For solving the problem existing in background technology, the invention provides a kind of new flavanols compounds with significant anticancer and anti-marine fouling organism activity.
Another object of the present invention is to provide a kind of method of extracting flavanols compounds of the present invention from wild kind beans.
Further aim of the present invention is to adopt the application in preparation prevention or medicine for treating tumor thing of flavanols compounds that preparation method of the present invention makes.
Further aim of the present invention is to adopt the flavanols compounds that preparation method of the present invention makes to prevent or treat the application in human cervical carcinoma, people's chronic myelogenous leukemia, human acute myeloid leukemia medicine in preparation.
Further aim of the present invention be adopt flavanols compounds that preparation method of the present invention makes prevent underwater structure surface be subject to halobiontic adhere to and/or stained aspect application.
Further aim of the present invention be adopt flavanols compounds that preparation method of the present invention makes prevent that marine organisms from adhering to and/or stained aspect application, wherein said marine organisms are that barnacle class is biological.
For reaching above object, the present invention by the following technical solutions:
Except as otherwise noted, the percentage ratio adopting in the present invention is mass percent.
The present invention isolates a kind of new flavanols compounds from wild kind beans, and it is active that this compound has significant anticancer and anti-marine fouling organism.
New flavanols compounds of the present invention has the structural formula shown in formula I:
The called after of this compound: (2R, 4R)-2 ', 4 '-dihydroxyl-5,7-dimethoxy flavane-4-alcohol ((2R, 4R) 2 ', 4 '-dihydroxy-5,7-dimethoxyflavan-4-ol).
A preparation method for flavanols compounds, comprises the following steps:
A, pulverizing: by obtaining meal after kind beanstalk dried and crushed of open country, standby;
B, refluxing extraction: the meal that step a is made, with alcohol reflux four times, merges ethanol extract, standby;
C, concentrated: the ethanol extract that step b is made carries out concentrating under reduced pressure after filtering and obtains medicinal extract, standby;
D, extraction: the medicinal extract that step c is made is suspended in water, extract with sherwood oil, ethyl acetate and propyl carbinol successively, then remove solvent, obtains respectively sherwood oil, ethyl acetate and n-butyl alcohol extract, standby;
E, separation: the acetic acid ethyl ester extract that steps d is made is through 100 ~ 300 order silica gel column chromatographies, with the petroleum ether-ethyl acetate gradient elution of volume ratio 20:1,10:1,5:1,2:1,1:1,0:1, obtain Fr.1 ~ Fr.6 totally 6 components, Fr.3 is through silica gel column chromatography, chloroform with volume ratio 98:2,95:5,90:10: methyl alcohol gradient elution, obtains component Fr.3A～3C.Fr.3C is through silica gel column chromatography, with the chloroform of volume ratio 80:20: and acetone wash-out, then obtain formula I compound through Sephadex LH-20 column chromatography methyl alcohol purifying.
The present invention has carried out cell toxicant and the test of anti-marine fouling organism attachment activity to flavanols compounds, experimental result demonstrates good inhibition human cervical carcinoma, people's chronic myelogenous leukemia, human acute myeloid leukemia cell strain is active and anti-marine fouling organism attachment activity, can be new compound or lead compound that medical industry and marine antifouling industry provide using value.
beneficial effect
1, the flavanols compounds that adopts preparation method of the present invention to make has significant restraining effect to tumour, human cervical carcinoma, people's chronic myelogenous leukemia or human acute myeloid leukemia cell, has good antitumour activity.There is good drug development prospect, can be used as anticancer active constituent or lead compound.
2, it is active that the flavanols compounds that adopts preparation method of the present invention to make also shows stronger inhibition biodeterioration, and the exploitation that can be fouling resistance coating or other fouling resistance product provides valuable lead compound, has good application prospect.
3, the flavanols compounds that adopts preparation method of the present invention to make is naturally occurring organic compound, for non-toxic compound, easily degraded in ocean environment, can not cause the pollution of water body environment, can not cause its enrichment in organism by food chain transmission, environmentally friendly, safe.
Accompanying drawing explanation
Fig. 1 is the compounds of this invention high resolution mass spectrum (HRESI-MS).
Fig. 2 be the compounds of this invention proton nmr spectra (
1h NMR).
Fig. 3 be the compounds of this invention carbon-13 nmr spectra (
13c NMR).
Fig. 4 is the DEPT spectrum of the compounds of this invention.
Fig. 5 is the COSY spectrum of the compounds of this invention.
Fig. 6 is the HSQC Correlated Spectroscopy of the compounds of this invention.
Fig. 7 is the HMBC Correlated Spectroscopy of the compounds of this invention.
Fig. 8 is the CD spectrum of the compounds of this invention.
Fig. 9 is the structural formula of the compounds of this invention.
Embodiment
The invention will be further described in description by following embodiment; but described is only preferred embodiment of the present invention; it is not limitation of the present invention; the modification that those skilled in the art's basic conception according to the present invention is made; only otherwise depart from basic thought of the present invention, all within protection scope of the present invention.
embodiment 1:a kind of preparation method of flavanols compounds
Material source: wild Fan Doucaiyu Kaiyuan, Yunnan, Tao Deding researcher is accredited as through Kunming Inst. of Botany, Chinese Academy of Sciences
uraria clarkei(Clarke) Gagnep., sample is stored in Yunnan Institute for nationalities's Hua Sheng institute sample shop.
A preparation method for flavanols compounds, comprises the following steps:
A, pulverizing: after being dried, wild kind beanstalk is ground into the meal of particle diameter 0.2cm size, and standby;
B, refluxing extraction: the meal that step a is made refluxing extraction 4 times at the temperature of 70 ~ 74 ℃, each 2 hours, with ethanol 10 Kg of 95% concentration, extract at every turn, merge ethanol extract, standby;
C, concentrated: the ethanol extract via hole diameter that step b is made is the filter paper filtering of 80 ~ 120 microns and carries out concentrating under reduced pressure at the temperature of 40 ~ 50 ℃, to proportion be 1.2 o'clock, obtain medicinal extract 1025g, standby;
D, extraction: the medicinal extract 1025g that step c is made is suspended in 3000ml water, with 3000ml sherwood oil, 3000ml ethyl acetate and 3000ml propyl carbinol, extract successively, every kind of solvent extraction 4 times, with Rotary Evaporators, boil off solvent again, obtain respectively sherwood oil, ethyl acetate and n-butyl alcohol extract 100g, 70g, 200g.
E, separation: the acetic acid ethyl ester extract that steps d is made is through 300 order silica gel column chromatographies, with the petroleum ether-ethyl acetate gradient elution of volume ratio 20:1,10:1,5:1,2:1,1:1,0:1, obtain Fr.1 ~ Fr.6 totally 6 components, Fr.1 is 10.2g, Fr.2 is 8.3g, Fr.3 is 7.0g, Fr.4 is 8.5g, Fr.5 is 6.8g, Fr.6 is 12.8g, and Fr.3 is through silica gel column chromatography, with the chloroform of volume ratio 98:2,95:5,90:10: methyl alcohol gradient elution, obtain component Fr.3A～3C, Fr.3A is 1.4g, and Fr.3B is 1.2g, and Fr.3C is 3.8g.Fr.3C is through silica gel column chromatography, with the chloroform of volume ratio 80:20: and acetone wash-out, then pass through Sephadex LH-20 column chromatography 2000ml column volume methyl alcohol purifying, obtain faint yellow amorphous powder 150mg.
embodiment 2:the Structural Identification of the faint yellow amorphous powder obtaining in embodiment 1
Described faint yellow amorphous powder (solvent is methyl alcohol), [α] 21 D=-15.1 (
c=0.14, MeOH); UV (MeOH)
λ max(log ε): 258 (3.56), 278 (3.73) nm; CD (
c=0.109, MeOH) λ (Δ ε) 242 (1.26), 280 (0.25); IR (KBr) ν
max: 3370,2951,1603,1506,1451,1270,1107,1010 cm
-1; HRESI-MS (accompanying drawing
1) show its quasi-molecular ion peak m/z 319.0734 [M+H]
+(calcd. 319.0765), determine that in conjunction with NMR spectrum its molecular formula is C
17h
18o
6, degree of unsaturation is 9.
1h and
13c NMR (accompanying drawing
2, accompanying drawing
3and accompanying drawing
4, attribution data in Table-
1) show in molecule have 2 phenyl ring (having 5 methyne double key carbons on phenyl ring), 2 methoxyl group (δ
c55.9,55.3), 2 oxygen methyne (δ of company
c67.4,62.1) and 1 methylene radical (δ
c26.7).In conjunction with COSY spectrum and HSQC Correlated Spectroscopy (accompanying drawing
5and accompanying drawing
6), and this yellow amorphous powder of documents data susceptible of proof is flavanols compounds; Further through the relevant (accompanying drawing of HMBC
7) confirming that C-5, C-7 position are substituted by methoxyl group, C-4, C-2 ', C-4 ' position are substituted by hydroxyl.The absolute configuration of compound is composed (accompanying drawing by CD
8) and with document (Slade D, Ferreira D, Marais JPJ. Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry, 2005,66,2177-2215) contrast turns out to be 2
r, 4
r-configuration, the structure of compound is finally confirmed, and this compound has formula I(accompanying drawing
9) shown in structural formula.By SCIFINDER database retrieval and literature query, confirm that this compound is new compound.
Table-
1. formula I compound
1h-and
13c-NMR (CDCl
3) data.
| No. | δ C | δ H |
| 2 | 67.4 | 5.28 (1H, dd, 1.6, 5.4) |
| 3 | 26.7 | 2.18 (1H, m), 2.29 (1H, m) |
| 4 | 62.1 | 5.67 (1H, dd, 4.4, 2.8) |
| 5 | 159.1 | - |
| 6 | 91.6 | 6.04 (1H, d, 2.4 ) |
| 7 | 161.9 | - |
| 8 | 92.9 | 5.99 (1H, d, 2.4 ) |
| 9 | 154.8 | - |
| 10 | 103.3 | - |
| 1' | 114.1 | - |
| 2' | 154.7 | - |
| 3' | 103.4 | 6.36 (1H, d, 2.4) |
| 4' | 157.4 | - |
| 5' | 108.2 | 6.40 (1H, dd, 8.4,2.4) |
| 6' | 131.8 | 7.22 (1H, d, 8.4 ) |
| 5-OMe | 55.9 | 3.87 (3H,s) |
| 7-OMe | 55.3 | 3.73 (3H,s) |
embodiment 3:different concentration ethanol solution extracts wild kind beans sample contrast experiment
Because the research report to wild kind beans chemical composition is few, therefore wish by using different concentration ethanol solution to extract wild kind beans sample, to find best ethanolic soln concentration.This not implies and cannot use other solvent extractions.
Concrete steps are as follows:
A, pulverizing: after wild kind beanstalk is dried, be ground into the particle of particle diameter 0.2 cm size, obtain meal, standby;
B, refluxing extraction: the meal making with step a at the temperature of 70 ~ 74 ℃ makes to extract solvent with the ethanol of 6 times of the amounts ethanol of 70% concentration, the ethanol of 80% concentration and 95% concentration respectively, refluxing extraction 4 times, each 2 hours, merge respectively ethanol extract, standby;
C, concentrated: the different concentration ethanol extracting solution via hole diameter respectively step b being made is the filter paper filtering of 80 ~ 120 microns and carries out concentrating under reduced pressure at the temperature of 40 ~ 50 ℃, to proportion be 1.2 o'clock, obtain medicinal extract, standby;
D, extraction: the medicinal extract respectively step c being made is suspended in 3 times of water gagings, 1 times of amount sherwood oil of water, 1 times of amount ethyl acetate of water and 1 times of amount propyl carbinol of water extract successively, every kind of solvent extraction 5 times, merge same solvent extract, use again Rotary Evaporators pressure reducing and steaming solvent, obtain respectively sherwood oil, ethyl acetate and n-butyl alcohol extract.
Experimental result shows to make to extract solvent with the ethanol of the ethanol of 70% concentration, 80% concentration and the ethanol of 95% concentration, the open country that obtained respectively kind beans acetic acid ethyl ester extract weight approaches, therefore with the ethanol of the ethanol of 70% concentration, the ethanol of 80% concentration and 95% concentration, do to extract solvent, can obtain the composition containing formula I compound equally.
The wild kind beans different solvents extract extract yield table of table 1.
embodiment 4: described formula I antitumor activity of compound detects
Adopt the increment restraining effect of improvement mtt assay assessing compound to tumour cell:
Get standby tumour cell suspension inoculation in 96 well culture plates, 90 μ L/ holes, continue to cultivate the given the test agent that adds different concns after 24 h, 10 μ L/ holes, making its final concentration is 100,10,1,0.1,0.01 μ g/mL, and each concentration is all established 3 multiple holes.The positive contrast of cis-platinum (DDP), the negative contrast of equal-volume RPMI1640 substratum.While establishing compound 100,10 μ g/mL, corresponding DMSO concentration is solvent contrast simultaneously, to eliminate the impact of DMSO cell growth.After dosing, continue to be placed in 37 ℃, 5% CO
2incubator is cultivated 72 h, and every hole adds MTT(5 mg/mL) 20 μ L, continue to cultivate 4 h, every hole adds three liquid [10%SDS-5% isopropylcarbinol-0.012 mol/L HCl(W/V/V)], 100 μ L Rong Xie formazans.By microplate reader, under 570 nm wavelength, measure the OD value in each hole.
By following formula, calculate cell increment inhibiting rate:
Inhibiting rate (%)=(OD value control wells-OD value dosing holes)/OD value control wells * 100%
Data statistic analysis: adopt Microsoft Excel 2003 to calculate inhibiting rate, adopt logit method, SPSS11.5 software package calculation of half inhibitory concentration IC
50.
Calculation of half inhibitory concentration IC
50, the half-inhibition concentration (IC to human cervical carcinoma (Hela), people's chronic myelogenous leukemia cell strain (k562) and human acute myeloid leukemia cell strain (HL60)
50) measurement result is respectively 13.9 ± 1.6 μ g/ml, 17.4 ± 4.3 μ g/ml, 19.1 ± 3.9 μ g/ml, show that compound of the present invention has good anti-tumor activity.
embodiment 5:measure the anti-kentrogon attachment activity of described formula I compound
Adopt suppressing the experimental model that line barnacle cyprids adheres to (can be referring to scientific and technical literature: Xu Y., He H. P., Qian P. Y., et al. Potent antifouling compounds produced by marine streptomyces.
bioresource Technology. 2010,101 (4): 1331-1336), the anti-kentrogon attachment activity of test formula I compound.Line adult barnacle (Darwin) picks up from tideland, Hong Kong (22 ° of 19'N, 114 ° of 16'E).In the polystyrene plastic culture vessel of 12 L, put into the seawater that 8 L filter, then line adult barnacle is put into container, place and allow it discharge larva, after 2.5 h, collect larva, the larva in this stage is called naupiar larva (nauplius), there is no adhesive ability.Naupiar larva is put into the container that 8 L filtering seas (filter membrane aperture is 0.22 μ m) is housed, bright in 24 ℃ of temperature and 15 h: aerated culture under the dark periodicity of illumination of 9 h, and feeding angle hair diatom (
chaetoceros gracilis Schutt), collection larva is standby later to cultivate 3 days, and the larva in this stage is called cyprids (cypris), has adhesive ability.Formula I compound is dissolved in methyl-sulphoxide (DMSO), then with sterile filtration seawater, is diluted to different concentration.In each hole of 24 well culture plates, add 1.0 mL test fluid and 15 ± 3 cyprids, each concentration is all established 3 multiple holes.Equal-volume sterile filtration seawater is done blank.24 well culture plates are bright in 24 ℃ of temperature and 15 h: under the dark periodicity of illumination of 9 h, cultivate after 48 h, statistics is adhered to the number of larva under the microscope.With SPSS VIersion 11 Software of Data Statistics, carry out statistical study.
Experimental result according to the researchists' such as Rittschof method (referring to scientific and technical literature: Richard B. F., DaVIid A. Z. F., Dan R. Molting of megalopae from the blue crab Callinectes sapidus:effects of offshore and estuarine cues.
marine ecology progress series. 1994,113:55-59) analyze.According to experimental result, can obtain the EC of 48 h
50(half suppresses to adhere to concentration, suppress larva adhesive rate for maximum suppress larva adhesive rate 50% time corresponding concentration), by EC
50the height of known detection material anti-biofouling activity.And after 24 h, calculate the mortality of larva, according to experimental result, can obtain the LC of 24 h
50(toxic limit medium dose), by LC
50/ EC
50the toxicity size of (toxic effect ratio) known detection material to kentrogon.Experiment analysis results shows (2
r,4
r)-2 ', 4 '-dihydroxyl-5, the activity that 7-dimethoxy flavane-4-alcohol has remarkable inhibition line kentrogon to adhere to, concentration (EC is adhered in its half inhibition
50) be 1.2 ± 0.4 μ g/ml, toxic effect is than (LC
50/ EC
50) be greater than 12.5.In addition, according to AVIelin etc. (referring to scientific and technical literature: Mary A., Mary VI., Rittschof D., Nagabhushanam R. Bacterial-barnacle interaction:potential of using juncellins and antibiotics to alter structure of bacterial communities.
j Chem. Ecol. 1993,19 (10): 2155-2167.), toxic effect is than (LC
50/ EC
50) the anti-biofouling compound that is greater than more than 10 is nontoxic anti-biofouling compound.The toxic effect of above-claimed cpd ratio is greater than 10 after tested, shows that this compound is nontoxic anti-biofouling compound.
Claims (5)
1. a flavanols compounds, is characterized in that: described flavanols compounds is that separation obtains from wild kind beans, and the structural formula of this compound is formula (I):
The called after of this compound: (2R, 4R)-2 ', 4 '-dihydroxyl-5,7-dimethoxy flavane-4-alcohol ((2R, 4R) 2 ', 4 '-dihydroxy-5,7-dimethoxyflavan-4-ol).
2. the preparation method of a kind of flavanols compounds according to claim 1, is characterized in that comprising the following steps:
A, pulverizing: by obtaining meal after kind beanstalk dried and crushed of open country, standby;
B, refluxing extraction: the meal that step a is made, with alcohol reflux four times, merges ethanol extract, standby;
C, concentrated: the ethanol extract that step b is made carries out concentrating under reduced pressure after filtering and obtains medicinal extract, standby;
D, extraction: the medicinal extract that step c is made is suspended in water, extract with sherwood oil, ethyl acetate and propyl carbinol successively, then remove solvent, obtains respectively sherwood oil, ethyl acetate and n-butyl alcohol extract, standby;
E, separation: the acetic acid ethyl ester extract that steps d is made is through 100 ~ 300 order silica gel column chromatographies, with the petroleum ether-ethyl acetate gradient elution of volume ratio 20:1,10:1,5:1,2:1,1:1,0:1, obtain Fr.1 ~ Fr.6 totally 6 components, Fr.3 is through silica gel column chromatography, chloroform with volume ratio 98:2,95:5,90:10: methyl alcohol gradient elution, obtain component Fr.3A～3C, Fr.3C is through silica gel column chromatography, chloroform with volume ratio 80:20: acetone wash-out, then obtain formula (I) compound through Sephadex LH-20 column chromatography methyl alcohol purifying.
3. a kind of flavanols compounds according to claim 1, is characterized in that: described flavanols compounds is in preparation prevention or treat the application in human cervical carcinoma, people's chronic myelogenous leukemia, human acute myeloid leukemia medicine.
4. a kind of flavanols compounds according to claim 1, is characterized in that: described flavanols compounds prevent underwater structure surface be subject to adhering to of kentrogon and/or stained aspect application.
5. a kind of flavanols compounds according to claim 1, is characterized in that: described flavanols compounds prevent that kentrogon from adhering to and/or stained aspect application.
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| CN108484628B (en) * | 2018-05-25 | 2020-01-17 | 广西中医药大学 | Application of quassin lactone compounds in preventing marine biofouling |
| CN110372656B (en) * | 2019-07-22 | 2022-04-05 | 沈阳药科大学 | Flavanol tiopronin derivative and its preparing method and use |
| CN112961137B (en) * | 2021-02-26 | 2022-08-12 | 沈阳药科大学 | Flavan-3,4-diol derivative and extraction method and application thereof |
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| CN1655806A (en) * | 2002-03-21 | 2005-08-17 | 玛尔斯有限公司 | Treatment of diseases involving defective gap junctional communication |
| CN101805333A (en) * | 2010-04-16 | 2010-08-18 | 湖南大学 | Cyclorotenoid, preparation method and application thereof |
| CN101830897A (en) * | 2010-05-10 | 2010-09-15 | 中国科学院化学研究所 | Novel isoquinoline alkaloid derivatives and preparation method and application thereof |
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| CN1655806A (en) * | 2002-03-21 | 2005-08-17 | 玛尔斯有限公司 | Treatment of diseases involving defective gap junctional communication |
| CN101805333A (en) * | 2010-04-16 | 2010-08-18 | 湖南大学 | Cyclorotenoid, preparation method and application thereof |
| CN101830897A (en) * | 2010-05-10 | 2010-09-15 | 中国科学院化学研究所 | Novel isoquinoline alkaloid derivatives and preparation method and application thereof |
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