CN104418829A - Structure, preparation method and use of compound vitrifolin B with anti-tumor effect - Google Patents
Structure, preparation method and use of compound vitrifolin B with anti-tumor effect Download PDFInfo
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- CN104418829A CN104418829A CN201310403018.1A CN201310403018A CN104418829A CN 104418829 A CN104418829 A CN 104418829A CN 201310403018 A CN201310403018 A CN 201310403018A CN 104418829 A CN104418829 A CN 104418829A
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- vitex rotundifolia
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
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Abstract
The invention belongs to the technical field of research of Chinese medicine and relates to a structure, a preparation method and use of compound vitrifolin B with an anti-tumor effect. The preparation method comprises the steps of drying the fruit of vitex rotundifolia in the sun, and smashing; soaking the smashed vitex rotundifolia for 5-7 days in methyl alcohol at a room temperature for four times; filtering, mixing filtrates; carrying out reduced pressure distillation to remove a methyl alcohol solvent to obtain a crude extract; dissolving the crude extract in 50-60 DEG C 2L of warm water; extracting with petroleum ether and chloroform in turn and carrying out reduced pressure distillation on soluble fraction of chloroform to remove the solvent to obtain a crude extract; and dissolving the crude extract with a proper amount of acetone for silicagel column chromatography, and eluting with chloroform and acetone in a ratio of 15:1 to obtain a compound which is an acicular crystal, wherein the molecular formula of the compound is C22H36O5; the name of the compound is vitrifolin B, and the structural formula of the compound is as shown in the specification. The vitrifolin B is characterized in that the vitrifolin B can be used for preparing pharmaceutical preparation with anti-tumor effect on a human lung adenocarcinoma cell and a hepatocellular carcinoma cell.
Description
Technical field
Traditional Chinese medicine research technical field belonging to the present invention, the present invention relates to a kind of structure and the preparation method and its usage with the compound Vitex rotundifolia element B of antitumor action.
Background technology
For a long time, disease threatens the health of the mankind always, especially cancer.Cancer is a kind of high lethality rate disease, and its mortality ratio occupies the first place of various diseases, and field of medicaments workers are devoted to develop antitumor drug safely and effectively always.Plant amedica has advantage and the potentiality to be exploited of its uniqueness at disease areas such as cancer, inflammation, immunity, so find the focus that natural antitumor medicine becomes cancer research field.
Natural compounds is the important source of new drug, and its pharmacological screening hit rate is higher than synthetic compound.Since nineteen sixty, by U.S. food and FAD in the cancer therapy drug approved, more than 60% from natural product.Within nearly 5 years, the new drug of 15 natural product derivatives is had to enter the staple markets such as the U.S., Europe, Japan; In addition, the derivative of nearly 20 natural products is also had for three phase clinical treatments.China's natural pharmaceutical resources enriches, and medication among the people is with a long history, have accumulated rich experience, and therefore the new drug initiative of natural origin has basis and development potentiality preferably in China.From traditional Chinese medicine material, excavate out the active compound for anti tumor of novel structure for this reason, be clue with the pass between chemical structure and biological activity, use modern vitochemical method for separating and analyzing and advanced pharmacological screening new technology, find lead compound, to the drug effect basis of illustrating Chinese medicine, study Development of New Drugs and to Chinese medicine modernization construction, there is important science and practice significance.
Vitex rotundifolia (
vitextrifolialinn. var.
simplicifoliacham) for Verbenaceae (Verbenaceae) Vitex (
vitex) machaka, be distributed widely in China's Coastal Areas, its mature fruit Simpleleaf Shrub Chastetree Fruit is China's tradition conventional Chinese medicine, has wind-dispelling heat-dissipating, effect that the stasis of blood, pain relieving are fallen apart in the clear sharp head, promoting the circulation of qi, and be used for the treatment of common cold due to wind-heat headache, gingivitis, has a dizzy spell.Vitex rotundifolia is widely distributed in China, comparatively other kind of plant of Vitex, Chinese scholars is less to its research, only minority scholar to originating from Japan, the Vitex rotundifolia of Korea S carries out chemical composition and bioactivity research, but very few to the Vitex rotundifolia research of originating from China.
Therefore, in order to better develop the Vitex rotundifolia resource of China's abundant, find the good natural compounds of anti-tumor activity, we are to originate from the Vitex rotundifolia fruit of In Shandong Weihai Wendeng City for research object, systematic research is carried out to its chemical composition and relevant biological activity, to finding the natural compounds with good biological activity, for new medicament screen provides prerequisite, more the exploitation of this kind of plant provide scientific basis.
Summary of the invention
1, the diterpene-kind compound with antitumor action of extraction and isolation from Vitex rotundifolia fruit, called after Vitex rotundifolia element B, its structure is as follows:
2, there is a preparation method of the compound Vitex rotundifolia element B of antitumor action, it is characterized in that comprising the following steps:
(1) get Vitex rotundifolia fruit to dry in the shade, pulverize, soak 5-7 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(2) soak 5-7 days by under residue methyl alcohol room temperature in (1), filter, obtain filtrate and residue;
(3) soak 5-7 days by under residue methyl alcohol room temperature in (2), filter, obtain filtrate and residue;
(4) soak 5-7 days by under residue methyl alcohol room temperature in (3), filter, obtain filtrate and residue;
(5) filtrate in (1), (2), (3), (4) merged, underpressure distillation removing methanol solvate obtains crude extract;
(6) crude extract in (5) is dissolved in 50 ° of C-60 ° of C 2 L warm water, then uses sherwood oil, chloroform extraction successively, obtain sherwood oil soluble part, chloroform soluble fraction after removal of solvent under reduced pressure respectively;
(7) chloroform soluble fraction underpressure distillation in (6) is removed desolventizing and obtain crude extract;
(8) crude extract in (7) dissolved with proper amount of acetone, mix thoroughly, dry under room temperature with 200-300 order industrial silicone, for silica gel column chromatography, with chloroform-acetone=15:1 wash-out, TLC combining data detection same section, obtains compound Vitex rotundifolia element B.
3, there is a purposes of the compound Vitex rotundifolia element B of antitumor action, be characterised in that it is for the preparation of pharmaceutical preparation human lung adenocarcinoma cell and human liver cancer cell to antitumous effect.
accompanying drawing illustrates:
The structure of accompanying drawing 1, compound Vitex rotundifolia element B (vitrifolin B)
embodiment
Of the present invention relate to a kind of compound Vitex rotundifolia element B with antitumor action structure and preparation method and its usage comprise following examples, the following examples can further illustrate the present invention, but do not limit the present invention in any way.
embodiment 1:
1, there is a preparation method of the compound Vitex rotundifolia element B of antitumor action, it is characterized in that comprising the following steps:
(1) get Vitex rotundifolia fruit to dry in the shade, pulverize, soak 5 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(2) residue in (1) is soaked 5 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(3) residue in (2) is soaked 5 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(4) residue in (3) is soaked 5 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(5) filtrate in (1), (2), (3), (4) merged, underpressure distillation removing methanol solvate obtains crude extract;
(6) crude extract in (5) is dissolved in 50 ° of C 2 L warm water, then uses sherwood oil, chloroform extraction successively, obtain sherwood oil soluble part, chloroform soluble fraction after removal of solvent under reduced pressure respectively;
(7) chloroform soluble fraction underpressure distillation in (6) is removed desolventizing and obtain crude extract;
(8) crude extract in (7) dissolved with proper amount of acetone, mix thoroughly, dry under room temperature with 200 order industrial silicones, for silica gel column chromatography, with chloroform-acetone=15:1 wash-out, TLC combining data detection same section, obtains compound Vitex rotundifolia element B.
2, there is a purposes of the compound Vitex rotundifolia element B of antitumor action, be characterised in that it is for the preparation of pharmaceutical preparation human lung adenocarcinoma cell and human liver cancer cell to antitumous effect.
embodiment 2:
1, there is a preparation method of the compound Vitex rotundifolia element B of antitumous effect, it is characterized in that comprising the following steps:
(1) get Vitex rotundifolia fruit to dry in the shade, pulverize, soak 7 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(2) residue in (1) is soaked 7 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(3) residue in (2) is soaked 7 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(4) residue in (3) is soaked 7 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(5) filtrate in (1), (2), (3), (4) merged, underpressure distillation removing methanol solvate obtains crude extract;
(6) crude extract in (5) is dissolved in 60 ° of C 2 L warm water, then uses sherwood oil, chloroform extraction successively, reduce pressure respectively
Sherwood oil soluble part, chloroform soluble fraction is obtained except after desolventizing;
(7) chloroform soluble fraction underpressure distillation in (6) is removed desolventizing and obtain crude extract;
(8) crude extract in (7) dissolved with proper amount of acetone, mix thoroughly, dry under room temperature with 300 order industrial silicones, for silica gel column chromatography, with chloroform-acetone=15:1 wash-out, TLC combining data detection same section, obtains compound Vitex rotundifolia element B.
2, there is a purposes of the compound Vitex rotundifolia element B of antitumor action, be characterised in that it is for the preparation of pharmaceutical preparation human lung adenocarcinoma cell and human liver cancer cell to antitumous effect.
structural Identification and the antitumour activity of compound Vitex rotundifolia element B are tested
1
the Structural Identification of compound Vitex rotundifolia element B
Vitex rotundifolia element B (vitrifolin B): white styloid, molecular formula is C
22h
36o
5, fusing point mp.171-173 oC, specific rotation [α]
=+32 (
c0.625, MeOH), high resolution electrospray ionization mass spectrum (HR-ESI-MS): quasi-molecular ion peak
m/z: 403.2451 (calculated value is 403.2455, C
22h
36o
5na
+), infrared spectra IR (KBr)
ν max3414,2964,2928,1739,1686,1463,1384,1261,1098,1051,1020 cm
-1;
1h (CDCl
3, 500 MHz, TMS) and
13c-NMR (DEPT) (CDCl
3, 125 MHz, TMS) and nuclear magnetic resonance data is in table 1.Through Scifinder retrieval, Vitex rotundifolia element B is new diterpene-kind compound.See Figure of description 1, Vitex rotundifolia element B (vitrifolin B) structure, accompanying drawing 2-accompanying drawing 3 is proton nmr spectra and the carbon-13 nmr spectra figure of this compound.
Table 1. Vitex rotundifolia element
1h (CDCl
3, 500 MHz, TMS) and
13c NMR (DEPT) nuclear magnetic resonance data
the antitumour activity test of 2 compound Vitex rotundifolia element B
Medicine and reagent: test compound DMSO dissolves, be diluted to required concentration with substratum before use, and RPMI 1640 is purchased from Giboo company, and calf serum is Hangzhou folium ilicis chinensis bio-engineering corporation product, and other reagent are domestic analytical pure.
Test method is MTT colorimetry: select 3 kinds of cell strains: human lung adenocarcinoma cell (A549), human liver cancer cell (HepG2) and human liver cancer cell (Smmc-7721), 3 kinds of cells are attached cell, and each cell strain uses the RPMI 1640 substratum (penicillin 1 × 10 of 10% calf serum respectively
5u/L, Streptomycin sulphate 1 × 10
5mg/L, NaHCO
32 g/L), at 37 DEG C of 5% CO
2condition under cellar culture, go down to posterity, the cell in vegetative period of taking the logarithm is tested.The cell of taking the logarithm vegetative period, is made into cell suspending liquid with after tryptic digestion with the RPMI RPMI-1640 containing 10% calf serum, it is inoculated in 96 orifice plates respectively, 10000-100000 cells/well, every hole substratum 100 μ L, 37 ° of C, 5% CO
2cultivate 24 hours in incubator.Former substratum is sopped up, medicine is made into different concns (200 μ L/ hole), adds in cell.Continue cultivation after 48 hours, add 10 μ L/ hole MTT, continue cultivation 4 hours, in sucking-off hole after nutrient solution, add DMSO liquid (150 μ L/ hole), crystallisate is dissolved.Microplate reader detects each hole OD value (determined wavelength 570 nm) and records result, curve plotting figure.In triplicate, positive control is mitomycin in above-mentioned experiment.
Calculation formula: cell survival rate (%)=(dosing group A value/control group A value) × l00%, makes the tropic by drug level and survival rate, obtains the half-inhibition concentration (IC of medicine to different Growth of Cells
50).Anti-tumor activity test result is as shown in table 2.
Table 2 compound Vitex rotundifolia element B (vitrifolin B) is to the 503nhibiting concentration IC of three kinds of cancer cells
50(μm ol/L)
Compound Vitex rotundifolia element B (vitrifolin B) restraining effect to human lung adenocarcinoma cell (A549), human liver cancer cell (HepG2), human liver cancer cell (Smmc-7721) is stronger as seen from Table 2.The present invention provides new lead compound to the new antitumor drug of development.
Claims (3)
1. the diterpene-kind compound with antitumor action of extraction and isolation from Vitex rotundifolia fruit, called after Vitex rotundifolia element B, its structure is as follows:
。
2. there is a preparation method of the compound Vitex rotundifolia element B of antitumor action, it is characterized in that comprising the following steps:
(1) get Vitex rotundifolia fruit to dry in the shade, pulverize, soak 5-7 days with under methyl alcohol room temperature, filter, obtain filtrate and residue;
(2) soak 5-7 days by under residue methyl alcohol room temperature in (1), filter, obtain filtrate and residue;
(3) soak 5-7 days by under residue methyl alcohol room temperature in (2), filter, obtain filtrate and residue;
(4) soak 5-7 days by under residue methyl alcohol room temperature in (3), filter, obtain filtrate and residue;
(5) filtrate in (1), (2), (3) merged, underpressure distillation removing methanol solvate obtains crude extract;
(6) crude extract in (5) is dissolved in 50 ° of C-60 ° of C 2 L warm water, then uses sherwood oil, chloroform extraction successively, point
Sherwood oil soluble part, chloroform soluble fraction is obtained after other removal of solvent under reduced pressure;
(7) chloroform soluble fraction underpressure distillation in (6) is removed desolventizing and obtain crude extract;
(8) crude extract in (7) dissolved with proper amount of acetone, mix thoroughly, dry under room temperature with 200-300 order industrial silicone, for silica gel column chromatography, with chloroform-acetone=15:1 wash-out, TLC combining data detection same section, obtains compound Vitex rotundifolia element B.
3. a kind of purposes with the compound Vitex rotundifolia element B of antitumor action prepared as claimed in claim 2, is characterised in that it is for the preparation of pharmaceutical preparation human lung adenocarcinoma cell and human liver cancer cell to antitumous effect.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108535401A (en) * | 2018-04-20 | 2018-09-14 | 国药集团德众（佛山）药业有限公司 | The identification method of wild pepper leaf |
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| US6107335A (en) * | 1997-11-18 | 2000-08-22 | Hoechst Marion Roussel Deutschland Gmbh | Esculentin A and esculentin B, a process for their preparation, and their use in the manufacture of medicaments |
| CN101057913A (en) * | 2007-06-06 | 2007-10-24 | 周应军 | New medical using of vitex and method for preparing medicinal intermediate |
| CN101670020A (en) * | 2009-05-25 | 2010-03-17 | 北京诚创康韵医药科技有限公司 | Composition for treating premenstrual syndrome |
| US20100249172A1 (en) * | 2007-03-05 | 2010-09-30 | Emory University | 9-chloro noscapine and its use in treating cancers, including drug-resistant cancers |
-
2013
- 2013-09-07 CN CN201310403018.1A patent/CN104418829A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6107335A (en) * | 1997-11-18 | 2000-08-22 | Hoechst Marion Roussel Deutschland Gmbh | Esculentin A and esculentin B, a process for their preparation, and their use in the manufacture of medicaments |
| US20100249172A1 (en) * | 2007-03-05 | 2010-09-30 | Emory University | 9-chloro noscapine and its use in treating cancers, including drug-resistant cancers |
| CN101057913A (en) * | 2007-06-06 | 2007-10-24 | 周应军 | New medical using of vitex and method for preparing medicinal intermediate |
| CN101670020A (en) * | 2009-05-25 | 2010-03-17 | 北京诚创康韵医药科技有限公司 | Composition for treating premenstrual syndrome |
Non-Patent Citations (2)
| Title |
|---|
| 吴闯等: "蔓荆子化学成分研究", 《药物生物技术》 * |
| 陈鸿雁等: "单叶蔓荆子黄酮类化学成分研究", 《天然产物研究与开发》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108535401A (en) * | 2018-04-20 | 2018-09-14 | 国药集团德众（佛山）药业有限公司 | The identification method of wild pepper leaf |
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Application publication date: 20150318 |