CN102697758A - Application of cryptomeriol in preparation of anti-tumor angiogenesis medicine - Google Patents
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
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- 230000000118 anti-neoplastic effect Effects 0.000 claims description 7
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Abstract
The invention discloses the application of cryptomeriol in preparation of anti-tumor angiogenesis medicine. Experiments prove that cryptomeriol can restrain propagation of tumor cells and has a more obvious restraining effect to new vessels of chick embnyo chorioallantoic membranes, so that cryptomeriol can be used for preparing anti-tumor angiogenesis medicine.
Description
Technical field
The invention belongs to antitumor and anti-angiogenic rebirth chemical compound field, the particularly new application of cryptomeriol in preparation antitumor and inhibition aberrant angiogenesis rebirth medicine.
Background technology
The M & M of cancer sharply rises in recent years, has become first killer who threatens China's residents ' health and life.
The main means of treatment cancer have at present: Shou art Zhi Liao ﹑ radiotherapy, chemotherapy; Wherein operative treatment is difficult to remove all cancerous cell; Radiotherapy is insensitive and side effect is bigger to the part tumor cell; Chemotherapy is to all toxic influence of whole body all cells, so these methods are receiving very big restriction aspect the oncotherapy utilization.In recent years, be devoted to seek one type in the drug research field tumor cell had specific killing effect and the less medicine of side effect.Therefore, separation prepares the focus that new antitumor drug becomes biomedicine field from Chinese crude drug.
The Yunnan Salvia japonica Thunb. (
S.yunnanensis) be the Labiatae salvia, be widely used as in recent years Radix Salviae Miltiorrhizae (
S.miltiorrhiza) substitute, its main component and Radix Salviae Miltiorrhizae are similar.Modern pharmacology shows; The extract of Yunnan Salvia japonica Thunb. has obvious antineoplastic; Reported mainly that at present the tanshinone material has inhibitory action to migration, the propagation of tumor cell, rarely had report in the unusual effect aspect newborn of antineoplastic vascular for other chemical constituents in the Salvia japonica Thunb..
Cryptomeriol (sugiol) is an abietane type diterpene, molecular formula C
20H
28O
2, molecular weight 300, CAS:511-05-7 was once successfully separated obtaining from Cortex Cryptomeriae Fortunei Radicis, be known compound, but do not have relevant report for the research of the newborn pharmacologically active of its antineoplastic vascular.
In recent years; Along with the pathogenetic of cancer, retinopathy and systemic lupus erythematosus (sle) further discovered; Angiogenesis is a crucial physiology step that causes this type of disease, so the research of angiogenesis inhibitors also becomes a focus in medical research field, 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 invention provides a kind of novel medical use of cryptomeriol, i.e. the application of cryptomeriol in the unusual rebirth medicine of preparation antineoplastic vascular.
The molecular formula of cryptomeriol described in the present invention C
20H
28O
2, molecular weight 300, CAS:511-05-7, chemical structural formula is following:
Cryptomeriol described in the present invention is used as the main active of antineoplastic vascular rebirth medicine or with other active component and processes medicine, treats cancer as angiogenesis inhibitors.Said medicine comprises the various dosage forms that pharmaceutical field is commonly used; Can add one or more pharmaceutically acceptable adjuvants; Said adjuvant comprises filler, diluent, binding agent, excipient, absorption enhancer, filler, surfactant and the stabilizing agent etc. that pharmaceutical field is conventional; Also can add flavouring agent, pigment and sweeting agent etc. in case of necessity, process various ways such as capsule, pill, powder, tablet, granule, oral liquid and injection.
The cryptomeriol that uses among the present invention is from the Salvia japonica Thunb. of Chinese crude drug Yunnan, to separate to obtain the cryptomeriol monomer, also can or prepare cryptomeriol through synthetic method from other plant origin.
Carry out the screening of antitumor action among the present invention with mtt assay; The result shows the human liver cancer cell of handling through cryptomeriol (HepG-2); Be 0.5,1.0,2.5,5.0 at adding consistency, during 10.0ug/mL with not dosing matched group relatively; Cell-proliferation activity has obvious decline, explains that cryptomeriol can suppress tumor cell proliferation.
With experimentation in the body of chick chorioallantoic membrane (CAM) experiment carrying out angiogenesis inhibiting; Experimental result shows that the chick chorioallantoic membrane handled through variable concentrations (5.0,10.0,15.0ug/mL) cryptomeriol and not dosing matched group are relatively; Its angiogenesis receives obvious suppression, explains that cryptomeriol has the effect of obvious angiogenesis inhibiting.
More than experiment proof: cryptomeriol is effective antitumour agent and anti-angiogenic unusual rebirth medicine, and curative effect is clear and definite, and is safe, is suitable for actual utilization and extention.
Description of drawings
Fig. 1 separates the process flow diagram of cryptomeriol from the Salvia japonica Thunb. of Yunnan for the present invention.
Fig. 2 acts on the experimental result sketch map (variable concentrations willow shirt alcohol is to tumor cell (HepG-2) effect back MTT experimental result) of tumor cell (HepG-2) for cryptomeriol of the present invention;
Fig. 3 cryptomeriol of the present invention acts on the experimental result sketch map (variable concentrations willow shirt alcohol is to the suppression ratio result of HepG-2 cell strain propagation influence) of tumor cell (HepG-2);
Fig. 4 be willow shirt alcohol of the present invention 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); A normal saline group among the figure, b Dexamethasone group, c cryptomeriol 5 ug/mL; D cryptomeriol 10 ug/mL, e cryptomeriol 15 ug/mL;
Fig. 5 is a willow shirt alcohol of the present invention to chick chorioallantoic membrane angiogenesis inhibitory action sketch map (calculate the blood vessel area of each experimental group according to the IPP image processing software, provide the block diagram statistical result directly perceived of respectively organizing the blood vessel area then) 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 is according to normal condition.
Embodiment 1: the preparation of cryptomeriol (cryptomeriol that uses among the following embodiment adopts following method to prepare)
Yunnan Salvia japonica Thunb. 3.2kg obtains CE 154g with the acetone supersound extraction of 8 times of quality 5 times; Mix appearance with 160g chromatographic silica gel (80-100 order),, add sample with 3.1kg 100-200 order chromatographic silica gel wet method dress post; (petroleum ether: ethyl acetate is 9:1,8:2,7:3 to use pure petroleum ether, petroleum ether-ethyl acetate mixed liquor successively; 1:1) eluting is collected the each several part eluent, concentrating under reduced pressure; Concentrated solution to petroleum ether: ethyl acetate=7:3 separates, and separation method is the purification on normal-phase silica gel column chromatography, and (15:1) carries out eluting with the petroleum ether-ethyl acetate mixed liquor; Obtain cryptomeriol 10mg; Through detecting 1H-NMR and the 13C-NMR data that obtain, data and Yang Lixin coincide in the 1H-NMR and the 13C-NMR data of the alcohol of willow shirt described in " chemical constitution study in the Salvia przewalskii " literary composition (sugiol), are cryptomeriol so identify this chemical compound.(see figure 1)
1H-NMR with
13The C-NMR data are following:
1H?NMR?(400?MHz,?DMSO-
d 6 )：
δ:?0.86?(3H,?s,?Me-18),?0.92?(3H,?s,?Me-19),?1.12?(3H,?s,?Me-20),?1.13?(6H,?d,?J?=?6.4?Hz,?Me-16?and?Me-17), 1.18?-2.48?(6H,?m,?H-1,?H-2?and?H-3),?1.71?(1H,?m,?H-5),?2.48?(2H,?m,?H-6),?3.13?(1H,?sept,?J?=?6.4?Hz,?H-15),?6.78?(1H,?s,?H-11),?7.64?(1H,?s,?H-14),?10.27?(1H,?s,?OH-12)。
13C?NMR?(100?MHz,?DMSO-
d 6 )：
δ:?37.51?(C-1),?18.52?(C-2),?40.88?(C-3),?32.91?(C-4),?49.14?(C-5),?35.55(C-6),?196.64?(C-7),?122.60?(C-8),?155.91?(C-9),?39.09?(C-10),?109.36?(C-11),?160.15(C-12),?132.57?(C-13),?125.05?(C-14),?26.10(C-15),?22.25?(C-16),?22.42?(C-17),?32.34?(C-18),?21.18?(q,?C-19),?23.07(C-20)。
Embodiment 2: the experiment of cryptomeriol extracorporeal anti-tumor function
The take the logarithm HepG-2 cell of phase, by the density of 3000 cells in every hole with the logarithmic (log) phase cell inoculation on 96 orifice plates, cultivate 24h after; Cryptomeriol preparation is become variable concentrations administration group (0.5,1.0,2.5,5.0,10ug/mL) and blank group, and per 5 holes are an experimental group, cultivation 72h; Add MTT, continue to hatch 4h, abandon supernatant; Every hole adds 150 μ LDMSO, and concussion 1h surveys the absorbance A value in ELIASA 490nm place.(seeing Fig. 2,3)
The result shows: the absorbance that shows MTT experiment when cryptomeriol concentration is 5.0ug/mL and 10ug/mL like Fig. 2 obviously descends, and explains that tumor cell proliferation obviously descends; According to suppression ratio=1-dosing group OD value/matched group OD value, calculate suppression ratio, show that like Fig. 3 cryptomeriol has significant inhibitory effect for tumor cell when cryptomeriol concentration is 5.0ug/mL and 10ug/mL.
Embodiment 3: anti-angiogenic rebirth effect experiment in the cryptomeriol body
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 cryptomeriol 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 cryptomeriol 1 mg, utilizes above-mentioned mother solution to be configured to 5 μ g/mL with the dehydrated alcohol dilution respectively, 10 μ g/mL, and the cryptomeriol 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 cryptomeriol 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 cryptomeriol in the unusual rebirth medicine of preparation antineoplastic vascular.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1698587A (en) * | 2004-05-21 | 2005-11-23 | 北京华医神农医药科技有限公司 | Total diterpene phenol originated from rosemary, its preparation method and use |
| CN102286059A (en) * | 2011-09-08 | 2011-12-21 | 南京泽朗医药科技有限公司 | Method for extracting ursolic acid, carnosic acid and rosmarinic acid from rosmarinus officinalis |
-
2012
- 2012-06-12 CN CN2012101917451A patent/CN102697758A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1698587A (en) * | 2004-05-21 | 2005-11-23 | 北京华医神农医药科技有限公司 | Total diterpene phenol originated from rosemary, its preparation method and use |
| CN102286059A (en) * | 2011-09-08 | 2011-12-21 | 南京泽朗医药科技有限公司 | Method for extracting ursolic acid, carnosic acid and rosmarinic acid from rosmarinus officinalis |
Non-Patent Citations (2)
| Title |
|---|
| LETÍCIA VERAS COSTA-LOTUFO ET AL: "Antiproliferative Effects of Abietane Diterpenes from Aegiphila lhotzkyana", 《PLANTA MED》 * |
| 艾伦强: "毛喉鞘蕊花抗肿瘤活性成分及其品质研究", 《中国优秀硕士学位论文全文数据库医药卫生科技辑》 * |
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Application publication date: 20121003 |