CN102657660A - Application of total triterpenes in preparing drugs inhibiting angiogenesis - Google Patents
Application of total triterpenes in preparing drugs inhibiting angiogenesis Download PDFInfo
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Abstract
The invention relates to application of total triterpenes in preparing drugs inhibiting angiogenesis. The application has the advantages that novel application of the total triterpenes in extractive of Actinidia chinensis roots is provided. An experiment proves that the total triterpenes 1,2,3,4 have remarkable inhibiting effect on multiplication of human umbilical vein endothelial cells (HUVEC) and canaliculization of HUVEC, have anti-angiogenic activity, and can serve as angiogenesis inhibitors. By means of the application of the total triterpenes in preparing the drugs inhibiting the angiogenesis, the anti-angiogenesis effect of the total triterpenes in the extractive of Actinidia chinensis roots is firstly found out, and the total triterpenes can serve as the angiogenesis inhibitors to be applied to treat new blood vessel dependence and new vessel related diseases including tumors, arthritis, skin and eye diseases, atherosclerosis and the like.
Description
Technical field
The present invention relates to the monomeric application of Chinese herbal medicine, specifically, is that a kind of triterpenoid compound that from Actinidiaceae Actinidia A.chinensis Planch. root, separates the inhibition angiogenesis that obtains suppresses the application in the angiogenesis drug in preparation.
Background technology
Angiogenesis is meant that the blood capillary that blastogenesis on already present capillary bed (sprouting) makes new advances is the process of master's vascular system.Initial at angiogenesis at first is that vascular endothelial cell dedifferentes, under the situation of various conditions being possesseds; Basement membrane of blood vessel attenuation or disappearance, endotheliocyte activate, breed, move, and new basement membrane forms; Cover endotheliocyte and VSMC, form new blood vessel at last.
Angiogenesis is the most important physiological process of fundamental sum in the human body, also is to keep stable machine and integrity, the important way of tissue and organ dysfunction.Angiogenesis is under the normal physiological situation; Only betide the ovary and the endometrium of fetal development, repair in trauma, gestation or menstrual cycle, but that can occur continuing, uncontrollable angiogenesis such as numerous disease such as tumor, eye neovascularization, arthritis, dermatopathy.
Malignant tumor is one of major disease of serious threat human health.The formation of microcirculation net in angiogenesis that provides material base for the subsequent growth of solid tumor and transfer that tumor-blood-vessel growth is meant that tumor cell brings out and the tumor.The tumor vascular tumor that is generated as provides necessary nutritional labeling and has discharged the cellular metabolism refuse, thereby has promoted the quick growth of tumor, even shifts through new vessels.Therefore, angiogenesis plays an important role in the development transfer process of tumor, suppresses development and diffusion transfer that this process can obviously stop tumor tissues.
The A.chinensis Planch. root is the root of Actinidiaceae Actinidia A.chinensis Planch. (Actinidia chinensis Planch.)., distribute extensively especially on Quzhou, Zhejiang, Jinhua, Wenzhou, Hangzhou and other places at China's southern area, aboundresources is a kind of important Chinese crude drug, is widely used in treating gastric cancer, pulmonary carcinoma, nasopharyngeal carcinoma, hepatocarcinoma and colon cancer etc.Triterpenoid compound separates from Chinese Radix Actinidiae Chinensis and obtains, at present this chemical compound report of suppressing that new vessels forms and using as angiogenesis inhibitor not also.
Chinese patent document CN101367861A discloses a kind of 2-hydroxyl-3-epoxy pentacyclic triterpenoid and derivant thereof, its preparation method and has been used for the purposes of the medicine of prophylactic treatment diabetes, cardiovascular disease, cerebrovascular disease and tumor in preparation.Chinese patent document CN101647801A discloses the application of a kind of tetracyclic triterpenoid cucurbatacin E in the preparation anti-angiogenic drugs.But the application in suppressing angiogenesis does not also appear in the newspapers at present about triterpenoid compound in the A.chinensis Planch. root extract.
Summary of the invention
The objective of the invention is to deficiency of the prior art, provide triterpenoid compound to suppress the application in the angiogenesis drug in preparation.
For realizing above-mentioned purpose, the technical scheme that the present invention takes is: triterpenoid compound suppresses the application in the angiogenesis drug in preparation, and described triterpenoid compound 1,2,3 and 4 has chemical constitution as follows and title:
Chemical compound 1:2 α, 3 beta-dihydroxies-12-alkene-28-ursolic acid;
Chemical compound 2:2 α, 3 α, 23-trihydroxy-12-alkene-28-ursolic acid;
Chemical compound 3:2 α, 3 α, 24-trihydroxy-12-alkene-28-oleanolic acid;
Chemical compound 4:2 α, 3 β, 23-trihydroxy-12-alkene-28-ursolic acid.
Described triterpenoid compound prepares through following step: under (1) room temperature the dry powder of A.chinensis Planch. is used 95% ethanol percolate extraction, evaporated in vacuo ethanol obtains the crude extract of A.chinensis Planch. then; (2) above-mentioned crude extract is used aqueous dispersion, use chloroform extraction afterwards, the evaporated in vacuo chloroform gets chloroform extract; (3) chloroform extract is through silica gel column chromatography, carries out gradient elution with the chloroform-methanol of 100:0-5:5, the eluent of the chloroform-methanol of collection 96:4, and solvent evaporated in vacuo gets the target bullion; (4) above bullion is through silica gel column chromatography, with the chloroform-methanol of 20:1 eluting repeatedly, and must target product.
The pharmaceutical dosage form of described inhibition angiogenesis is capsule, tablet, microcapsule formulation, injection, suppository, spray or ointment.
Described inhibition angiogenesis drug is for suppressing the medicine of neonate tumour blood vessel.
Described inhibition angiogenesis drug is for suppressing the newborn medicine of psoriatic lesions tissue blood vessel.
Described inhibition angiogenesis drug is for suppressing the medicine of Paget ' s disease angiogenesis.
Described inhibition angiogenesis drug is the medicine of the angiogenesis of the optimum blood vessel hyperplasia disease of inhibition.
Described inhibition angiogenesis drug is the medicine of the angiogenesis of inhibition arthritis pathological changes tissue.
Described inhibition angiogenesis drug is the medicine of the angiogenesis of inhibition neovascular oculopathy.
Described inhibition angiogenesis drug is for suppressing the medicine of atherosclerotic lesion place angiogenesis.
The invention has the advantages that:
The invention provides the new purposes of triterpenoid compound in the A.chinensis Planch. root extract; Experiment shows; 1,2,3,4 pairs of Human umbilical vein endothelial cells of triterpenoid compound (HUVEC) are bred, the HUVEC tubule forms all has the obvious suppression effect; Explain that it has anti-angiogenesis activity, can be used as angiogenesis inhibitor and use.The present invention finds the blood vessel formation against function of triterpenoid compound in the A.chinensis Planch. root extract first, can be applied to new vessels dependency and the diseases related treatments of new vessels such as tumor, arthritis, skin and ophthalmic diseases, atherosclerosis as angiogenesis inhibitor.
Description of drawings
Accompanying drawing 2 is triterpenoid compound 1,2,3,4 pairs of inhibitory action that the HUVEC tubule forms.
The specific embodiment
Below in conjunction with accompanying drawing the specific embodiment provided by the invention is elaborated.
The preparation of embodiment 1 triterpenoid compound 1,2,3,4
1. triterpenes 1,2,3,4 chemical compounds of the present invention prepare through following method:
(1) extract: under the room temperature with the dry powder of A.chinensis Planch. with 95 % ethanol percolate extraction, evaporated in vacuo ethanol obtains the crude extract of A.chinensis Planch. then;
(2) extraction: above-mentioned crude extract is used aqueous dispersion, use chloroform extraction afterwards, the evaporated in vacuo chloroform gets chloroform extract;
(3) column chromatography: get (2) middle chloroform extract and carry out silica gel column chromatography, silica gel is 200-300 order (3kg), chloroform-methanol gradient elution (100:0,99:1; 49:1,19:1,9:1,4:1; 7:3,3:2,1:1), the consumption of each gradient elution agent is 4 times of column volumes; Branches such as every 500mL are collected, and detect with the purification on normal-phase silica gel TLC, merge same composition through TLC, obtain 11 components (Fr.1-Fr.11).
(4) purification: the component Fr. 1 that gets gained in (3) carries out silica gel column chromatography, and silica gel is the 300-400 order, and its consumption is 10 times with the crude product quality; Carry out eluting with chloroform-methanol 19:1; The consumption of eluant is 10 times of column volumes, and branches such as every 50mL are collected, and detect with the purification on normal-phase silica gel TLC; Merge same composition through TLC, obtain 5 components (Fr. 1a-Fr.1e).Get component Fr. 1b and carry out silica gel column chromatography, (20:1) carries out eluting with chloroform-methanol, and branches such as every 10mL are collected, and detects with the purification on normal-phase silica gel TLC, collects principal spot, and solvent evaporated gets chemical compound 1,2 and 4.
(5) purification: the component Fr. 11 that gets gained in (3) carries out silica gel column chromatography, and silica gel is the 300-400 order, and its consumption is 10 times with the crude product quality; Carry out eluting with chloroform-methanol 10:1; The consumption of eluant is 10 times of column volumes, and branches such as every 50mL are collected, and detect with the purification on normal-phase silica gel TLC; Merge same composition through TLC, obtain 9 components (Fr. 11a-Fr.11i).Get component Fr. 11a and carry out silica gel column chromatography, (20:1) carries out eluting with chloroform-methanol, and branches such as every 10mL are collected, and detects with the purification on normal-phase silica gel TLC, collects principal spot, and solvent evaporated gets chemical compound 3.
2. the physicochemical property of said triterpenoid compound and spectral data are following:
(1) chemical compound 1
2 α, 3 beta-dihydroxies-12-alkene-28-ursolic acid:
White powder.ESI-MS?m/z?471?[M-H]
-。13C-NMR?(CD
3OD，100MHz)：48.59(C-1)，69.83(C-2)，84.79(C-3)，40.8(C-4)，56.99(C-5)，19.84(C-6)，34.54(C-7)，41.14(C-8)，48.59(C-9)，38.51(C-10)，24.75(C-11)，126.98(C-12)，140.12(C-13)，43.63(C-14)，29.49(C-15)，25.63(C-16)，49.76(C-17)，54.69(C-18)，40.74(C-19)，40.74(C-20)，32.09(C-21)，38.43(C-22)，29.63(C-23)，17.52(C-24)，17.94(C-25)，18.15(C-26)，24.4(C-27)，181.83(C-28)，17.8(C-29)，21.87(C-30)。
(2) chemical compound 2
2 α, 3 α, 23-trihydroxy-12-alkene-28-ursolic acid:
White powder.ESI-MS?m/z487[M-H]
-。13C-NMR(CD
3OD，100MHz)：42.66?(C-1)，67.52(C-2)，79.03?(C-3)，42.8?(C-4)，44.47(C-5)，19.26(C-6)，34.1(C-7)，41.16(C-8)，48.87(C-9)，39.42(C-10)，24.73(C-11)，126.97(C-12)，140.15(C-13)，43.72(C-14)，29.48(C-15)，25.64(C-16)，49.72(C-17)，54.71(C-18)，40.73(C-19)，40.43(C-20)，32.1(C-21)，38.45(C-22)，71.62(C-23)，17.93(C-24)，17.70(C-25)，18.19(C-26)，24.47(C-27)，181.81(C-28)，17.96(C-29)，21.88(C-30)。
(3) chemical compound 3
2 α, 3 α, 24-trihydroxy-12-alkene-28-oleanolic acid:
White powder.ESI-MS?m/z487[M-H]
-。13C-NMR(C
5D
5N，100MHz)：42.33(C-1)，66.35(C-2)，74.39(C-3)，42.12(C-4)，49.68(C-5)，19.07(C-6)，33.32(C-7)，40.16(C-8)，48.35(C-9)，38.79(C-10)，23.88(C-11)，122.61(C-12)，144.95(C-13)，42.33(C-14)，28.40(C-15)，26.23(C-16)，48.36(C-17)，45.29(C-18)，38.79(C-19)，42.11(C-20)，31.04(C-21)，38.79(C-22)，28.40(C-23)，17.52(C-24)，17.18(C-25)，19.07(C-26)，26.23(C-27)，180.25(C-28)，31.04(C-29)，23.88(C-30)。
(4) chemical compound 4
2 α, 3 β, 23-trihydroxy-12-alkene-28-ursolic acid:
White powder.ESI-MS?m/z?487[M-H]
-。13C-NMR(C
5D
5N，100MHz)：42.81(C-1)，69.18(C-2)，78.38(C-3)，42.81(C-4)，43.89(C-5)，18.75(C-6)，33.39(C-7)，40.29(C-8)，48.30(C-9)，39.63(C-10)，24.14(C-11)，125.82(C-12)，139.63(C-13)，43.89(C-14)，28.87(C-15)，25.11(C-16)，48.07(C-17)，53.78(C-18)，39.69(C-19)，39.63(C-20)，31.90(C-21)，37.68(C-22)，24.00(C-23)，66.65(C-24)，17.72(C-25)，18.75(C-26)，24.13(C-27)，180.29(C-28)，17.72(C-29)，21.61(C-30)。
Need to prove that chemical compound 1,2,3,4 of the present invention is tetracyclic triterpenoid, belongs to similar compound.
The influence of embodiment 21,2,3,4 pairs of Human umbilical vein endothelial cells of triterpenoid compound (HUVEC) propagation
Purpose and principle: adopt the CCK-8 method to detect the propagation of HUVEC, this method has been widely used in cell proliferation test research.Contain WST – 8 (2-(2-methoxyl group-4-nitrobenzophenone)-3-(4-nitrobenzophenone)-5-(2 in the CCK-8 reagent; 4-disulfonic acid benzene)-and 2H-tetrazolium list sodium salt), it is reduced to the yellow Jia Za product (Formazan) with high water soluble by the dehydrogenase in the cell mitochondrial under the effect of electron carrier 1-Methoxy PMS (1-methoxyl group-5-toluphenazine DMS).The quantity that generates De Jia Za thing is directly proportional with the quantity of living cells.Measure its absorbance with enzyme-linked immunosorbent assay instrument in 450 nm wavelength, can reflect living cells quantity indirectly.
Method: the HUVEC cell is inoculated in 96 orifice plates by 5000 cell number in every hole, and puts 37 ℃ of incubators and cultivate 24 h.After treating that the cell growth reaches 80% fusion, with triterpenoid compound 1,2; 3,4 by 1 μ M, 3 μ M; 10 μ M, 30 μ M concentration add respectively in the hand-hole, the matched group that adds equal-volume solvent DMSO is set simultaneously and has only culture fluid not have the blank of cell; Every Kong Jiayu hole inner volume places 37 ℃ of incubators to continue to hatch 2 h than being the CCK-8 solution of 1:10 volume behind drug effect 48 h, detects the OD value at 450 nm places with the wavelengthtunable hole ELIASA that declines.Calculate cell viability by following formula:
Cell viability (%)=(OD
Sample-OD
Blank)/(OD
Control-OD
Blank) * 100%
Result and conclusion: please with reference to accompanying drawing 1, accompanying drawing 1 is a triterpenoid compound 1,2, the effect of 3,4 pairs of HUVEC inhibition of proliferation.Matched group DMSO concentration is lower than 0.1%; The result is expressed as
± SD, n=4-6;
*: compare with matched group (add solvent DMSO group) and to have significant difference (
p<0.05);
*: compare with matched group (add solvent DMSO group) and to have utmost point significant difference (
p<0.01).
As shown in Figure 1, when concentration was 30 μ M, 1,3,4 almost completely suppressed HUVEC propagation (cell survival rate is lower than 15%).
Purpose and principle: adopt In vitro angiogenesis assay kit to investigate the HUVEC tubule and form.Matrigel is the basement membrane matrix from a kind of solubility of mice EHS sarcoma extraction.Main component comprises: glutinous albumen, the collagen iv etc. of connecting of layer contain TGF-β fibroblast growth factor, tissue fibers proenzyme activation factor and other somatomedin of in the EHS tumor, expressing naturally simultaneously.At room temperature, Matrigel can assemble the biological activity host material that generation is similar to the mammalian cell basement membrane automatically.HUVEC can adhere to into pipe on Matrigel, thereby can be used for studying medicine forms the tubule effect to endotheliocyte influence.
Method: all relate to the operation of Matrigel all carries out on ice, and used orifice plate and rifle head all need pre-cooling.Get 50 μ l Matrigel sol solutions and join in 96 orifice plates of pre-cooling, and be positioned over 37 ℃ of incubators curing at least 1 h.(cell density is 1 * 10 will to contain the HUVEC cell of variable concentrations polyketone class 4 and 5 chemical compounds
5/ ml) adding is covered with in 96 orifice plates of Matrigel respectively, places CO
2Cultivate 10 h in the cell culture incubator.Add solvent DMSO group and be contrast.Be inverted observation vascularization under the optical microscope behind 10 h.
Result and conclusion: please with reference to accompanying drawing 2, accompanying drawing 2 is triterpenoid compound 1,2,3,4 pairs of inhibitory action that the HUVEC tubule forms.(A) little length of tube (% matched group), the result is expressed as
± SD, n=4-6; Compare * with matched group
p<0.05, * *
p<0.01; Compare ## with ursolic acid under the same concentrations
p<0.05.。(B) the HUVEC tubule under the variable concentrations compound effects forms picture.Bar?=?300?μM。
As shown in Figure 2, chemical compound 2,4 more than the 3 μ M, chemical compound 1 more than the 10 μ M, chemical compound 3 forms the HUVEC tubule more than 30 μ M has remarkable inhibitory action.It should be noted that chemical compound 2 significantly suppresses the HUVEC tubule and forms under non-cell toxicity concentration.
The above only is a preferred implementation of the present invention; Should be pointed out that for those skilled in the art, under the prerequisite that does not break away from the inventive method; Can also make some improvement and replenish, these improvement and replenish and also should be regarded as protection scope of the present invention.
Claims (10)
1. triterpenoid compound suppresses the application in the angiogenesis drug in preparation, and described triterpenoid compound 1,2,3 and 4 has chemical constitution as follows and title:
Chemical compound 1:2 α, 3 beta-dihydroxies-12-alkene-28-ursolic acid;
Chemical compound 2:2 α, 3 α, 23-trihydroxy-12-alkene-28-ursolic acid;
Chemical compound 3:2 α, 3 α, 24-trihydroxy-12-alkene-28-oleanolic acid;
Chemical compound 4:2 α, 3 β, 23-trihydroxy-12-alkene-28-ursolic acid.
2. application according to claim 1; It is characterized in that; Described triterpenoid compound prepares through following step: under (1) room temperature the dry powder of A.chinensis Planch. is used 95% ethanol percolate extraction, evaporated in vacuo ethanol obtains the crude extract of A.chinensis Planch. then; (2) above-mentioned crude extract is used aqueous dispersion, use chloroform extraction afterwards, the evaporated in vacuo chloroform gets chloroform extract; (3) chloroform extract is through silica gel column chromatography, carries out gradient elution with the chloroform-methanol of 100:0-5:5, the eluent of the chloroform-methanol of collection 96:4, and solvent evaporated in vacuo gets the target bullion; (4) above bullion is through silica gel column chromatography, with the chloroform-methanol of 20:1 eluting repeatedly, and must target product.
3. application according to claim 1 is characterized in that, the pharmaceutical dosage form of described inhibition angiogenesis is capsule, tablet, microcapsule formulation, injection, suppository, spray or ointment.
4. application according to claim 1 is characterized in that, described inhibition angiogenesis drug is for suppressing the medicine of neonate tumour blood vessel.
5. application according to claim 1 is characterized in that, described inhibition angiogenesis drug is for suppressing the newborn medicine of psoriatic lesions tissue blood vessel.
6. application according to claim 1 is characterized in that, described inhibition angiogenesis drug is for suppressing the medicine of Paget ' s disease angiogenesis.
7. application according to claim 1 is characterized in that, described inhibition angiogenesis drug is the medicine of the angiogenesis of the optimum blood vessel hyperplasia disease of inhibition.
8. application according to claim 1 is characterized in that, described inhibition angiogenesis drug is the medicine of the angiogenesis of inhibition arthritis pathological changes tissue.
9. application according to claim 1 is characterized in that, described inhibition angiogenesis drug is the medicine of the angiogenesis of inhibition neovascular oculopathy.
10. application according to claim 1 is characterized in that, described inhibition angiogenesis drug is for suppressing the medicine of atherosclerotic lesion place angiogenesis.
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Cited By (2)
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| CN111481657A (en) * | 2020-06-18 | 2020-08-04 | 北京欣颂生物科技有限公司 | JZY-17 and use of compounds for the preparation of a medicament for the treatment of psoriasis |
| GB2578390B (en) * | 2017-07-13 | 2022-08-31 | Univ East China Science & Tech | Saponin compound targeting PD-1 and application thereof |
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Cited By (3)
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Application publication date: 20120912 |