CN104341430A - 3-phenylcoumarin robustic acid as well as extraction method and application thereof - Google Patents
3-phenylcoumarin robustic acid as well as extraction method and application thereof Download PDFInfo
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- CN104341430A CN104341430A CN201410522224.9A CN201410522224A CN104341430A CN 104341430 A CN104341430 A CN 104341430A CN 201410522224 A CN201410522224 A CN 201410522224A CN 104341430 A CN104341430 A CN 104341430A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
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Abstract
The invention discloses 3-phenylcoumarin robustic acid as well as an extraction method and application thereof. 3-phenylcoumarin robustic acid has a structural formula as shown in the specification as well as a chemical name of 3-(p-methoxyphenyl)-4-hydroxy-5-methoxy-2', 2'-dimethyl-6,7-dihydropyrancoumarin, a molecular formula of C22H20O6, and relative molecular weight of 380. 3-phenylcoumarin robustic acid disclosed by the invention has anti-tumor and other biological activities, can be effectively applied in preparation of anti-tumor drugs and has very strong inhibition effect on human gastric cancer cells, liver cancer cell lines, human lung cancer cells, cervical cancer cells, ovarian cancer cells and the like, the extraction method is simple and feasible and the extraction efficiency is relatively high.
Description
Technical field
The present invention relates to technical field of medical chemistry, be specifically related to a kind of native Radix Glycyrrhizae A and extracting method thereof, and by native Radix Glycyrrhizae A for the preparation of on antitumor drug.
Background technology
Cancer has risen to the mankind being only second to cardiovascular disorder second largest " killer " disease.Cancer and cardiovascular disorder have become dead first cause.The prospect finding exploitation effective antitumor new drug from plant is wide, and at present, the natural active product of numerous different structure and mechanism of action has become the focus of domestic and international anti-cancer agent research.In the two batch weight large new drug initiative project that China starts continuously, plant origin medicine particularly utilizes the research and development of the natural drug of China's plant resources to be all listed in key support object, because the mechanism of action of the antitumor drug of plant origin is unique, anticancer therapeutic is remarkable, progressively dominate in clinical application.
According to " Chinese Plants will " record, Dalbergia plant (Dalbergia) has 28 kinds in China, only have at present two kinds studied, especially dalbergia wood Dalbergia odorifera is studied maximum.Many pharmacologically actives all show that dalbergia wood has anti-diabetic, anti-oxidant, hyperglycemia, anti-inflammatory, and tumour and the effect such as antibacterial, therefore develop diabetes medicament very meaningful from this platymiscium.Lignum Dalbergiae benthamii (Dalbergia benthami Prain), has another name called: any of several broadleaf plants rattan fiber crops, two Guangdong wingceltises, liana, in being born in sparse woods and thicket, is distributed in the ground such as Guangdong, Guangxi, Hainan.Medicinal part is stem, can be used for restoring menstrual flow and invigorating blood circulation, and cures mainly the symptoms such as wound, arthralgia and myalgia and caused by energy stagnation and blood stasis menoxenia.
At present, to the research of this plant without any bibliographical information..The present invention isolates first and identifies a compound from this plant, and be native Radix Glycyrrhizae A through nuclear-magnetism, Mass Spectrometric Identification, the content in plant is up to 3.5%.This compound derives from native Radix Glycyrrhizae Derris eriocarpa How at first, but in this plant, content is lower, and application is limited to.Soil Radix Glycyrrhizae A belongs to coumarin kind compound, and have the biological activitys such as antitumor, therefore, this patent is that the Application and Development of this compound provides strong guarantee.
Summary of the invention
An object of the present invention is to provide a kind of native Radix Glycyrrhizae A, this native Radix Glycyrrhizae A has the biological activitys such as antitumor.Another object is to provide a kind of method extracting this native Radix Glycyrrhizae A, and this native Radix Glycyrrhizae A can be applied in and prepares in antitumor drug, makes the antitumor drug extracted possess the effect of effective prevention and prohibition tumor progression.
In order to solve the problems of the technologies described above, the invention provides a kind of native Radix Glycyrrhizae A and extracting method thereof and purposes.
The structural formula of native Radix Glycyrrhizae A of the present invention is:
The chemical name of this native Radix Glycyrrhizae A is: 3-(p-methoxyphenyl)-4-hydroxy-5-methyl oxygen base-2 ', 2 '-dimethyl-6,7-dihydropyrane tonka bean camphor;
The molecular formula of this native Radix Glycyrrhizae A is: C
22h2
0o
6;
The relative molecular weight of this native Radix Glycyrrhizae A is: 380.
Can extract this native Radix Glycyrrhizae A by the following method, it comprises the steps:
1) with Lignum Dalbergiae benthamii meal for raw material, using ethanol as solvent, adopt percolation extract, obtain extract medicinal extract after evaporating solvent.
2) extract medicinal extract is added aqueous suspension, then add petroleum ether extraction to suspension and be separated petroleum ether part medicinal extract, then in suspension, add extraction into ethyl acetate obtain ethyl acetate extract medicinal extract;
3) get described ethyl acetate extract medicinal extract, be repeatedly separated with silica gel column chromatography, obtain water white transparency crystalline particulate compound, be target product soil Radix Glycyrrhizae A.
This native Radix Glycyrrhizae A may be used for preparing antitumor drug, such as makes one or more medicines in antineoplastic injection, tablet, pill, capsule, suspension agent or emulsion.
Beneficial effect of the present invention: the native Radix Glycyrrhizae A that the present invention extracts from Lignum Dalbergiae benthamii has the biological activitys such as antitumor.And easy extraction of the present invention, extraction yield is higher, effectively can be applied to and prepare in antitumor drug, and can produce very high inhibition effect to gastric carcinoma cells, hepatoma cell strain, human lung carcinoma cell, cervical cancer cell, ovarian cancer cell etc.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, can implement according to this with reference to specification sheets word to make those skilled in the art.
Embodiment 1
The extracting method of the present invention's soil Radix Glycyrrhizae A comprises following concrete steps:
1) get Lignum Dalbergiae benthamii meal 10.0kg, with 10 times amount 80% ethanol percolate extraction, united extraction liquid, obtains extract medicinal extract after evaporating solvent;
2) extract medicinal extract is added aqueous suspension, then add petroleum ether extraction to suspension and be separated petroleum ether part medicinal extract, then in suspension, add extraction into ethyl acetate obtain ethyl acetate extract medicinal extract;
3) get ethyl acetate extract medicinal extract 30g, be repeatedly separated with silica gel column chromatography, obtain water white transparency crystalline particulate compound, be target product soil Radix Glycyrrhizae A.The way that this silica gel column chromatography is separated can according to following operation: first with chloroform-acetone gradient elution (chloroform → 80: 1 → 50: 1 → 30: 1 → 15
:1 → 7: 1 → 3: 1 → acetone), collect 358 stream parts altogether, know with TLC inspection and merge, merge identical flow point, obtain 14 components (A, B, C, D, E, F, G, H, I, G, K, L, M, N) altogether; Wherein, I component is white powder, then 300mg component I is got, with sherwood oil-acetone gradient elution (15: 1 → 7: 1 → 3: 1), collect 103 stream parts altogether, know with TLC inspection and merge, merge identical flow point, the component obtained, at sherwood oil-acetone (7: 1) wash-out position, obtains water white transparency crystalline particulate compound 80.55mg, and this water white transparency crystalline particulate compound is native Radix Glycyrrhizae A.
The structural formula of the native Radix Glycyrrhizae A that above-described embodiment 1 extracts is:
The chemical name of this native Radix Glycyrrhizae A is 3-(p-methoxyphenyl)-4-hydroxy-5-methyl oxygen base-2 ', 2 '-dimethyl-6,7-dihydropyrane tonka bean camphor, molecular formula is C
22h
20o
6, relative molecular weight is 380.Obtaining its physico-chemical property through physico-chemical analysis instrument is: water white transparency particulate state, m.p.203-206 DEG C.EI-MS(m/z)：381[M+1]
+，380[M]
+，315[M-15]，337，321，307，233，232，217，203，175，161，148，138，133。
1H-NMR(400MHz，CDCl
3)δ：9.97(1H，s，4-OH)，7.46(2H，dd，J＝11.4Hz，2.9Hz，H-2′，H-6′)，6.97(2H，dd，J＝8.7Hz，2.9Hz，H-3′，H-5′)，6.63(1H，s，H-Ar)，6.50(1H，d，J＝10Hz，H-4″)，5.77(1H，d，J＝10Hz，H-3″)，3.96(3H，s，4′-OCH
3)，3.77(3H，s，5-OCH
3)，1.48(6H，s，-CH
3)。
13C-NMR(125MHz，CDCl
3)δ：160.1(C-2)，101.7(C-3)，162.6(C-4)，153.7(C-5)，124.2(C-6)，157.6(C-7)，110.6(C-8)，152.1(C-9)，103.8(C-10)，123.2(C-1′)，131.4(C-2′)，113.5(C-3′)，158.8(C-4′)，113.5(C-5′)，131.4(C-6′)，77.5(C-2″)，115.0(C-3″)，131.7(C-4″)，64.4(3′-OCH
3)，55.2(5-OCH
3)。
Embodiment 2
Above-described embodiment 1 is extracted the native Radix Glycyrrhizae A obtained and carries out anti tumor activity in vitro experiment:
Mtt assay is widely used in Activity determination, large-scale screening anti-tumor medicine, cell toxicity test and the tumor radiosensitivity mensuration etc. of some biologically active factorss, has highly sensitive, economic dispatch feature.Exogenous MTT can be reduced to water-insoluble bluish voilet crystallization first a ceremonial jade-ladle, used in libation (Formazan) and be deposited in cell by the succinodehydrogenase in viable cell plastosome, measure its absorbance value with enzyme-linked immunosorbent assay instrument at 490nm wavelength place, can indirectly reflect viable cell quantity.Within the scope of certain cell count, the amount that MTT crystallization is formed is directly proportional to cell count.When being 50% by computerized compound to inhibition rate of tumor cell, the concentration of corresponding medicine, is called half-inhibition concentration IC
50, i.e. half-inhibition concentration, in general, IC
50numerical value less, illustrate that the inhibit activities of this medicine to cell is higher.IC when this experiment native Radix Glycyrrhizae A and 5-FU of the present invention that utilized Bliss method to calculate is 50% to inhibiting rates such as gastric carcinoma cells, hepatoma cell strain, human lung carcinoma cell, cervical cancer cell, ovarian cancer cells
50value.Experimental result is as shown in the table:
As can be seen from the result of embodiment 2, native Radix Glycyrrhizae A of the present invention shows through anticancer experiment in vitro, and it has strong antitumor activity component.Native Radix Glycyrrhizae A of the present invention can make one or more medicines in antineoplastic injection, tablet, pill, capsule, suspension agent or emulsion.Native Radix Glycyrrhizae A of the present invention and the medicine be extracted into thereof can produce very high inhibition effect to gastric carcinoma cells, hepatoma cell strain, human lung carcinoma cell, cervical cancer cell, ovarian cancer cell etc.Can obtain from the correlation data table, the restraining effect of its antithetical phrase cervical cancer cell HeLa is the most obvious, result for the treatment of is better, and native Radix Glycyrrhizae A of the present invention is also good than the effect of 5-FU to the restraining effect of other cancer cells, and the present invention is that the new antitumor drug of research and development provides new thinking.
Although embodiment of the present invention are open as above, but it is not restricted to listed in specification sheets and embodiment utilization, it can be applied to various applicable the field of the invention completely, for those skilled in the art, can easily realize other amendment, therefore do not deviating under the universal that claim and equivalency range limit, the present invention is not limited to specific details.
Claims (3)
1. a native Radix Glycyrrhizae A, is characterized in that, the structural formula of described native Radix Glycyrrhizae A is:
The chemical name of described native Radix Glycyrrhizae A is: 3-(p-methoxyphenyl)-4-hydroxy-5-methyl oxygen base-2 ', 2 '-dimethyl-6,7-dihydropyrane tonka bean camphor;
The molecular formula of described native Radix Glycyrrhizae A is: C
22h
20o
6;
The relative molecular weight of described native Radix Glycyrrhizae A is: 380.
2. an extracting method of native Radix Glycyrrhizae A as claimed in claim 1, is characterized in that, comprise the steps:
1) with Lignum Dalbergiae benthamii meal for raw material, using ethanol as solvent, adopt percolation extract, obtain extract medicinal extract after evaporating solvent.
2) described extract medicinal extract is added aqueous suspension, then add petroleum ether extraction to suspension and be separated petroleum ether part medicinal extract, then in suspension, add extraction into ethyl acetate obtain ethyl acetate extract medicinal extract;
3) get described ethyl acetate extract medicinal extract, be repeatedly separated with silica gel column chromatography, obtain water white transparency crystalline particulate compound, be target product soil Radix Glycyrrhizae A.
3. a purposes of native Radix Glycyrrhizae A as claimed in claim 1, is characterized in that, described native Radix Glycyrrhizae A is as the purposes preparing antitumor drug.
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| CN201410522224.9A CN104341430B (en) | 2014-09-30 | 2014-09-30 | A kind of soil Radix Glycyrrhizae A and extracting method thereof and purposes |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945408A (en) * | 2015-04-30 | 2015-09-30 | 广西民族大学 | Coumarin compounds, and preparation method and application thereof |
| CN105287692A (en) * | 2015-11-25 | 2016-02-03 | 广西中医药大学 | Dalbergia benthami prain extractive, and preparation method and application thereof |
| CN105287511A (en) * | 2015-11-25 | 2016-02-03 | 广西中医药大学 | Application of 3-phenylcoumarin robustic acid |
| CN107033115A (en) * | 2017-03-14 | 2017-08-11 | 广西中医药大学 | Lignum Dalbergiae benthamii ketone and its extracting method |
| CN109232599A (en) * | 2018-10-08 | 2019-01-18 | 广西中医药大学 | O- with anti-tumor activity is to trifluoromethylbenzoyl soil Radix Glycyrrhizae A and its preparation method and application |
| CN109232600A (en) * | 2018-10-08 | 2019-01-18 | 广西中医药大学 | O- with anti-tumor activity is to methylbenzyl soil Radix Glycyrrhizae A, preparation method and pharmaceutical preparation and purposes |
| CN109232601A (en) * | 2018-10-08 | 2019-01-18 | 广西中医药大学 | With active native Radix Glycyrrhizae A derivative of anti-cervical cancer and its preparation method and application |
| CN111217825A (en) * | 2020-02-25 | 2020-06-02 | 广西中医药大学 | 4-O-aminopropyl earth licorice A derivative and preparation and application thereof |
| CN111217824A (en) * | 2020-02-25 | 2020-06-02 | 广西中医药大学 | 4-O-arylaminopropyl glycyrrhiza A derivative and preparation and application thereof |
| CN112655758A (en) * | 2020-12-30 | 2021-04-16 | 广西壮族自治区药用植物园 | Application of licorice root extract in preparation of fruit and vegetable preservative |
| CN115197236A (en) * | 2022-06-29 | 2022-10-18 | 广西中医药大学 | Linear type glabrous greenbrier rhizome A analogue and preparation and application thereof |
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| Title |
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Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945408A (en) * | 2015-04-30 | 2015-09-30 | 广西民族大学 | Coumarin compounds, and preparation method and application thereof |
| CN105287511B (en) * | 2015-11-25 | 2018-07-10 | 广西中医药大学 | The application of native Radix Glycyrrhizae A |
| CN105287692A (en) * | 2015-11-25 | 2016-02-03 | 广西中医药大学 | Dalbergia benthami prain extractive, and preparation method and application thereof |
| CN105287511A (en) * | 2015-11-25 | 2016-02-03 | 广西中医药大学 | Application of 3-phenylcoumarin robustic acid |
| CN107033115B (en) * | 2017-03-14 | 2019-02-15 | 广西中医药大学 | Lignum Dalbergiae benthamii ketone and its extracting method |
| CN107033115A (en) * | 2017-03-14 | 2017-08-11 | 广西中医药大学 | Lignum Dalbergiae benthamii ketone and its extracting method |
| CN109232600B (en) * | 2018-10-08 | 2021-04-20 | 广西中医药大学 | O-p-methylbenzyl earth licorice A with antitumor activity, preparation method, pharmaceutical preparation and application |
| CN109232600A (en) * | 2018-10-08 | 2019-01-18 | 广西中医药大学 | O- with anti-tumor activity is to methylbenzyl soil Radix Glycyrrhizae A, preparation method and pharmaceutical preparation and purposes |
| CN109232601A (en) * | 2018-10-08 | 2019-01-18 | 广西中医药大学 | With active native Radix Glycyrrhizae A derivative of anti-cervical cancer and its preparation method and application |
| CN109232599A (en) * | 2018-10-08 | 2019-01-18 | 广西中医药大学 | O- with anti-tumor activity is to trifluoromethylbenzoyl soil Radix Glycyrrhizae A and its preparation method and application |
| CN109232599B (en) * | 2018-10-08 | 2021-04-20 | 广西中医药大学 | O-p-trifluoromethyl benzoyl soil licorice A with antitumor activity and its prepn and use |
| CN111217825B (en) * | 2020-02-25 | 2022-09-20 | 广西大学 | 4-O-aminopropyl earth licorice A derivative and preparation and application thereof |
| CN111217824A (en) * | 2020-02-25 | 2020-06-02 | 广西中医药大学 | 4-O-arylaminopropyl glycyrrhiza A derivative and preparation and application thereof |
| CN111217825A (en) * | 2020-02-25 | 2020-06-02 | 广西中医药大学 | 4-O-aminopropyl earth licorice A derivative and preparation and application thereof |
| CN111217824B (en) * | 2020-02-25 | 2022-09-23 | 广西大学 | 4-O-arylaminopropyl glycyrrhiza A derivative and preparation and application thereof |
| CN112655758A (en) * | 2020-12-30 | 2021-04-16 | 广西壮族自治区药用植物园 | Application of licorice root extract in preparation of fruit and vegetable preservative |
| CN112655758B (en) * | 2020-12-30 | 2024-02-27 | 广西壮族自治区药用植物园 | Application of radix glycyrrhizae extract in preparation of fruit and vegetable preservative |
| CN115197236A (en) * | 2022-06-29 | 2022-10-18 | 广西中医药大学 | Linear type glabrous greenbrier rhizome A analogue and preparation and application thereof |
| CN115197236B (en) * | 2022-06-29 | 2023-09-19 | 广西中医药大学 | Linear type glabra A analogue and preparation and application thereof |
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|---|---|
| CN104341430B (en) | 2016-08-24 |
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