CN102670621A - Application of maslinic acid in preparation of anti-tumor-angiogenesis medicament - Google Patents
Application of maslinic acid in preparation of anti-tumor-angiogenesis medicament Download PDFInfo
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- CN102670621A CN102670621A CN201210191756XA CN201210191756A CN102670621A CN 102670621 A CN102670621 A CN 102670621A CN 201210191756X A CN201210191756X A CN 201210191756XA CN 201210191756 A CN201210191756 A CN 201210191756A CN 102670621 A CN102670621 A CN 102670621A
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- MDZKJHQSJHYOHJ-UHFFFAOYSA-N crataegolic acid Natural products C1C(O)C(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MDZKJHQSJHYOHJ-UHFFFAOYSA-N 0.000 title claims abstract description 41
- MDZKJHQSJHYOHJ-LLICELPBSA-N maslinic acid Chemical compound C1[C@@H](O)[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MDZKJHQSJHYOHJ-LLICELPBSA-N 0.000 title claims abstract description 40
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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- HJMFZRRKMVZJCX-UHFFFAOYSA-N delta-Maslinic acid Chemical compound C1C(O)C(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5=C4CCC3C21C HJMFZRRKMVZJCX-UHFFFAOYSA-N 0.000 description 1
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- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses new application of a compound, namely maslinic acid, in the preparation of an anti-tumor-angiogenesis medicament. According to experiments, by taking the maslinic acid as an angiogenesis inhibitor, tumor growth is inhibited by inhibiting angiogenesis in tumor tissues. According to an experimental result, the maslinic acid can inhibit the abnormal growth of a blood vessel and the proliferation of tumor cells and is high in angiogenesis inhibiting activity.
Description
Technical field
The invention belongs to antitumoral compounds and anti-angiogenic rebirth chemical compound field, particularly relate to the purposes of maslinic acid in preparation antineoplastic vascular rebirth medicine.
Background technology
Angiogenesis is interior important physical of body and pathological process, and under the normal condition, its promotion and inhibition are in a dynamic balance state, only occur in plurality of processes such as embryo's formation, wound healing and women's physiological periodic.Yet,, will follow the appearance and the immune disorder of a lot of diseases in case this balance is broken.Especially the angiogenesis that in body, exists promotes that the factor has surpassed the angiogenesis inhibitive factor; Balance will be partial to the generation of neovascularity, thereby possibly cause the generation of serious diseases such as cancer, rheumatic arthritis, diabetic blindness, systemic lupus erythematosus (sle).
At present the main means of treatment cancer have: Shou art Zhi Liao ﹑ radiotherapy, chemotherapy, wherein chemotherapy is receiving very big restriction because of its shortcoming such as insensitive and side effect is bigger to the part tumor cell aspect the oncotherapy utilization.In recent years, suppress the novel targets that neonate tumour blood vessel becomes the treatment cancer, angiogenesis inhibitors is potential to become high specificity, one type of new antitumor drug that toxic and side effects is little.From natural product, separate the new inhibiting chemical compound of angiogenesis that has of preparation and become the research focus of field of medicaments.
The Yunnan Salvia japonica Thunb. (
S.yunnanensis)Be the Labiatae salvia, its main component and Radix Salviae Miltiorrhizae (
S.miltiorrhiza) similar, be a kind of traditional Chinese medicines material, have many-sided curative effect clinically, antipruritic etc. like: tranquilizing by nourishing the heart, promoting blood flow to regulate menstruation, analgesia, be used to treat cardiovascular and cerebrovascular disease.Maslinic acid is therefrom to separate the triterpenoid compound that obtains, and the maslinic acid chemical structural formula is following:
Maslinic acid is the triterpene structure.Once had bibliographical information from Cortex ulmi pumilae, successfully to separate and obtain this chemical compound, certain cytotoxicity is arranged, it can be used as the antagonist and the antitumoral compounds of angiogenesis but do not appear in the newspapers at present.
At present, more common angiogenesis inhibitors is mainly chemical medicine, as: DPTZ, Puli etc.; It is to come from biogenetic derivation that part is also arranged, like peptide class, exogenous pigment epidermal derived factors etc.
Summary of the invention
The novel medical use that the purpose of this invention is to provide a kind of maslinic acid; Be the application of maslinic acid in preparation antineoplastic vascular rebirth medicine; It is used as the main active of antineoplastic vascular rebirth medicine or with other active component and processes medicine, treats cancer as angiogenesis inhibitors.
Maslinic acid chemical compound of the present invention can extract from natural plants; Also can chemosynthesis; With natural Chinese medicine, like Radix Salviae Miltiorrhizae or congener is a raw material, adopt methods such as solvent extraction method, solvent extraction, vacuum concentration drying or lyophilization; Obtain maslinic acid through methods such as crystalline deposit and filtrations again, its structure can be passed through
1HNMR with
13The CNMR data are confirmed.
The present invention utilizes human hepatoma cell strain HepG-2; Test through MTT; Test maslinic acid to the influence of the propagation of tumor cell, experimental result shows, maslinic acid concentration can effectively suppress the propagation of tumor cell 0.5,1.0,2.5,5.0, during 10ug/mL.
The present invention utilizes the chick chorioallantoic membrane experimental model; Test the influence of maslinic acid for experimental model angiogenesis in the body; Experimental result shows that maslinic acid can effectively suppress the chick chorioallantoic membrane vessel growth, at the remarkable angiogenesis inhibiting of 10.0,15.0 ug/mL; Its effect is better than positive drug, demonstrates good neovascularization inhibiting activity.
Above experimental result shows: maslinic acid can suppress the misgrowth of blood vessel; Suppress the tumor cell increment; It can be used as the effective ingredient of preparation angiogenesis inhibitors; Use separately or share or combine, process oral agents or non-oral agents is used to treat cancer, the newborn relevant disease that causes of aberrant angiogenesis according to conventional method with acceptable excipient etc.
Description of drawings
Fig. 1 is the present invention separates maslinic acid from the Salvia japonica Thunb. of Yunnan a schematic flow sheet.
Fig. 2 is the experimental result sketch map that maslinic acid acts on human hepatoma cell strain HepG-2 among the present invention (the MTT experimental test result that different maslinic acid administration concentration are right);
Fig. 3 is the experimental result sketch map that maslinic acid acts on human hepatoma cell strain HepG-2 among the present invention (the variable concentrations maslinic acid is to the suppression ratio result of HepG-2 cell strain propagation influence);
Fig. 4 be among the present invention maslinic acid to chick chorioallantoic membrane angiogenesis inhibitory action as a result sketch map (maslinic acid acts on chick chorioallantoic membrane; The experimental result that after the IPP image processing software is handled, suppresses angiogenic growth); Among the figure: a normal saline, b dexamethasone, c maslinic acid 5 ug/mL group; D maslinic acid 10ug/mL group, e maslinic acid 15 ug/mL group;
Fig. 5 be among the present invention maslinic acid to chick chorioallantoic membrane angiogenesis inhibitory action sketch map (statistical result of angiogenic growth area data) as a result.
The specific embodiment
Below in conjunction with accompanying drawing and embodiment the present invention is done further explain; But be not limited to following embodiment at protection domain of the present invention, among the embodiment, the experimental technique of unreceipted actual conditions; According to normal condition, or the condition of advising according to manufacturer experimentizes.
Embodiment 1: the preparation of maslinic acid (maslinic acid that uses among the following embodiment adopts following method to prepare)
Employing Labiatae salvia Yunnan Salvia japonica Thunb. (
Salvia yunnanensisC. 10 kilograms on dry root H. Wright) or rhizome are ground into coarse powder, extract with 25L acetone merceration, three times repeatedly, concentrate CE; The extractum water is made into suspension, uses ethyl acetate extraction, obtains the ethyl acetate section; This section adopts silica gel column chromatography to separate, and (petroleum ether: ethyl acetate is 9:1,8:2 to use pure petroleum ether, petroleum ether-ethyl acetate mixed liquor successively; 7:3; 1:1) eluting is collected the each several part eluent, concentrating under reduced pressure; To petroleum ether: the concentrated solution of ethyl acetate 8:2 eluting part separates, and uses half preparative high-performance liquid chromatographic (semipre-HPLC) to prepare maslinic acid at last.Obtain through detection
1H-NMR with
13C-NMR data acknowledgement and Tan Zongwei are at maslinic acid described in " the triterpenoid compound composition separates and evaluation in the dove tree " literary composition
1H-NMR with
13The C-NMR data are coincide.(see figure 1)
1H-NMR with
13The C-NMR data are following:
1H?NMR?(400?MHz,?CDCl3)：
δ: 0.93,0.98,0.99,1.01,1.07,1.26,1.27 (each 3H, s), 3.39 (1H, d, J=9.5Hz, H-3), 4.09 (1H, m, H-2); 5.46 (1H, t, J=3.5Hz, H-12)
13C?NMR?(100?MHz,?CDC
l3)：
47.8（C-1）68.6（C-2）83.9（C-3）39.8（C-4）55.9?(C-5)?18.9（C-6）33.2（C-7）39.9（C-8）48.2（C-9）38.6（C-10）24.0（C-11）122.5（C-12）144.9（C-13）42.3（C-14）28.3（C-15）23.7（C-16）46.7（C-17）42.0（C-18）46.5（C-19）31.0（C-20）34.3（C-21）33.3（C-22）29.4（C-23）17.7（C-24）16.9（C-25）17.5（C-26）26.2（C-27）180.1（C-28）33.3（C-29）23.8（C-30）
Embodiment 2: maslinic acid is to the influence experiment of human hepatoma cell strain HepG-2 propagation
With human hepatoma cell strain HepG-2 at 37 ℃, 5% CO
2Cultivate after 24 hours, its density according to 3000 Ge ∕ holes be seeded in 96 orifice plates, cultivate 24 hours more under these conditions after, with maslinic acid process 0.5,1.0,2.5,5.0, the medicinal liquid of 10.0ug/mL adds in 96 orifice plates, at 37 ℃, 5% CO
2Condition under continue to cultivate 72 hours, carefully shift out supernatant, every hole adds 150 μ LDMSO, concussion 1h, the survey absorbance A value in ELIASA 490nm place.(seeing Fig. 2,3)
Experimental result when maslinic acid concentration is 10.0ug/mL, obviously suppresses the propagation of tumor cell like Fig. 2, shown in 3.
Embodiment 3: maslinic acid is tested chick chorioallantoic membrane angiogenesis inhibitory action
1, buys the fresh hatching egg of producing in three days, hatching egg is carried out surperficial wiping sterilization, afterwards hatching egg is put into constant incubator, 37.8 ℃ of temperature are set, keep certain humidity (60%), hatched with this understanding 7 days with 84 disinfectant solution or bromo geramine.
2, window and administration
2.1 blank solution, the preparation of positive control solution and maslinic acid solution: ⑴ blank formulations prepared from solutions: compare with blank normal saline; ⑵ positive control formulations prepared from solutions: with 5 mg/mL dexamethasone sodium phosphate injections as positive control; ⑶ cryptomeriol formulations prepared from solutions: it is subsequent use with the mother solution that dehydrated alcohol is configured to 1mg/mL accurately to take by weighing maslinic acid 1 mg; Utilize above-mentioned mother solution to be configured to 5 μ g/mL with the dehydrated alcohol dilution respectively; 10 μ g/mL, the maslinic acid alcoholic solution cold preservation of 15 μ g/mL is subsequent use;
Following 2.2 window with the administration concrete operations: ⑴ with 75% ethanol disinfection liquid to the disinfection of Embryo Gallus domesticus stub end surface; ⑵ remove eggshell, shell membrane successively with flat angle tweezers; Expose cameral mantle; ⑶ expose the chorioallantoic membrane tissue with syringe and bent angle tweezers separated gas chamber film and chorioallantoic membrane, and ⑷ is given to the sparse relatively zone of blood vessel on the chorioallantoic membrane with medicine through medicine carrying;
After the administration, seal window,, cultivated 48 hours under the condition of humidity (60%) 37.8 ℃ of temperature with adhesive tape.
3, preparation of specimen and IMAQ
3.1 preparation of specimen: open and seal adhesive tape; In the administration window, drip 2mL fixative (methanol: acetone 1:1); Fixedly behind the 10min, treat blood vessel fixing fully after, peel off the eggshell around the air chamber; The chorioallantoic membrane of administered area is fully exposed, use operating scissors to cut with about 2.5 * 2.5cm of carrier as the center
2Chorioallantoic membrane tissue in the scope is tiled in the culture dish that the PBS buffer is housed, and it is fully launched, and then it is transferred on the microscope slide;
3.2 IMAQ: with the blank sheet of paper is background, under the available light condition, takes pictures with digital camera, and it is the chick chorioallantoic membrane photo at center that original position is taken with pharmaceutical carrier (medicine carrying);
4, date processing: the chorioallantoic membrane photo of gathering is carried out Flame Image Process with software calculate the blood vessel area, adopt the SPSS DAS that data are analyzed afterwards.
Experimental result shows that Fig. 4 is the photo of enhancing contrast ratio after the IPP software processes, from figure, finds out that obviously when the administration concentration of maslinic acid was 10.0,15.0 ug/mL, angiogenic growth obviously was suppressed; Fig. 5 has shown the block diagram that calculates bleeding from anus pipe area through area, and as can be seen from the figure working as administration concentration is 10.0,15.0 ug/mL, and the blood vessel area obviously descends.
Claims (1)
1. the application of maslinic acid in preparation antineoplastic vascular rebirth medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210191756XA CN102670621A (en) | 2012-06-12 | 2012-06-12 | Application of maslinic acid in preparation of anti-tumor-angiogenesis medicament |
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|---|---|---|---|
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102008715A (en) * | 2009-09-07 | 2011-04-13 | 华东师范大学 | Antitumor MA-TNF alpha medicine composition and application thereof |
| CN102091078A (en) * | 2010-09-27 | 2011-06-15 | 林秀坤 | Maslinic acid anti-hepatocarcinoma effect and maslinic acid medicinal preparation |
-
2012
- 2012-06-12 CN CN201210191756XA patent/CN102670621A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102008715A (en) * | 2009-09-07 | 2011-04-13 | 华东师范大学 | Antitumor MA-TNF alpha medicine composition and application thereof |
| CN102091078A (en) * | 2010-09-27 | 2011-06-15 | 林秀坤 | Maslinic acid anti-hepatocarcinoma effect and maslinic acid medicinal preparation |
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Application publication date: 20120919 |