CN107365345A - A kind of D rings insert oxygen pregnane glycoside compounds and its application - Google Patents
A kind of D rings insert oxygen pregnane glycoside compounds and its application Download PDFInfo
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- 229930182470 glycoside Natural products 0.000 title claims abstract description 22
- -1 oxygen pregnane glycoside compounds Chemical class 0.000 title claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 8
- 239000001301 oxygen Substances 0.000 title claims abstract description 8
- 201000001441 melanoma Diseases 0.000 claims abstract description 22
- 239000003814 drug Substances 0.000 claims abstract description 19
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims abstract description 10
- 230000009876 antimalignant effect Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 8
- 150000002611 lead compounds Chemical class 0.000 abstract description 2
- 210000004881 tumor cell Anatomy 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 14
- 241001408435 Epigynum auritum Species 0.000 description 12
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- 150000002338 glycosides Chemical class 0.000 description 9
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- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 2
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- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 238000003012 network analysis Methods 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- RDRCCJPEJDWSRJ-UHFFFAOYSA-N pyridine;1h-pyrrole Chemical compound C=1C=CNC=1.C1=CC=NC=C1 RDRCCJPEJDWSRJ-UHFFFAOYSA-N 0.000 description 1
- 244000145591 rattan cane Species 0.000 description 1
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- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a D ring to insert oxygen pregnane glycoside compounds, the structural formula of compound is shown below, the compound is applied in anti-malignant mela noma medicine, experimental result shows that the compound has the activity for suppressing the propagation of maligna element tumour cell UACC 62；The present invention provides lead compound to develop new anti-malignant mela noma medicine, is advantageous to develop plant medicine resource；
Description
Technical field
The present invention relates to a D- ring to insert oxygen pregnane glycoside compounds and its application, and particularly it is anti-pernicious black in preparation
Application in pigment tumor medicine.
Background technology
Malignant mela noma is a kind of high malignancy tumour, occurred in skin, occupies malignant tumour of skin the 3rd and (accounts for
6.8%~20%), foreign statistic accounts for the 1%~2% of all malignant tumours.Melanoma is just turning into a kind of common in cutaneum carcinoma
Lethal form.The whole world melanoma incidence of disease raises year by year, it is newest be diagnosed as melanoma patient it is all over the world each
Ground and with the increasing proportion of the incidence of disease annual 3%~8% it, the increased speed of fatal rate occupy the first places of other malignant tumours.
Usually it has been often late period and prognosis mala in diagnosis because it has the potential of early stage transfer.Malignant mela noma is high
The main reason for case fatality rate, to lack effective treatment means, the patient of DISTANT METASTASES IN was had occurred and that particularly with those.
It is applied to clinical medicine or antibiotic majority at present and suppression and destruction is risen to body, is not suitable for making for a long time
With, it is difficult to tumor disease is treated, this is still a challenge in clinical field.The maximally effective single chemotherapeutics of malignant mela noma
It is Dacarbazine (dacarbazine DTIC), up to 20% remission rate, the effective percentage of other drugs nitroso ureas (BCNU) is
10%~20%.Temozolomide (temozolamide) is a new antitumoral medicine, also there is effect relatively certainly, can have 21% to have
Efficiency, patient especially is shifted to cental system.Combined chemotherapy frequently with cis-platinum, Dacarbazine (DTIC), BCNU (BCNU),
The combined chemotherapies such as tamoxifen, vincristine, actinomycin D, endoxan, methotrexate (MTX), fluorouracil (5-Fu), chemotherapy are former
It is then to carry out long intermittent therapy.Therefore, the chemotherapeutics of existing malignant mela noma has that cure rate is low, and toxic side effect is obvious
The shortcomings of.
Chinese herbal medicine has the advantages such as the low, Small side effects of toxicity, is coordinating body whole machine balancing, enhancing body resistance against diseases side
Face has unique curative effect.Research shows that the antitumor mechanism of Chinese medicine mainly includes strengthen immunity, suppresses the growth of cancer cell,
Division, inducing apoptosis of tumour cell, suppress four aspects of Tumor Angiongesis.The research of Chinese medicine antitumor machanism is gradually being goed deep into,
By strengthening changing the body too many levels caused by Chinese medicine various combination, Mutiple Targets, so as to network analysis itself and metastases
The inner link of whole process.Therefore, there is an urgent need to develop the new antitumoral preparation of a kind of high-efficiency low-toxicity, compared to Chemo-Therapy
Treat, Chinese medicine has the advantages that and people's tissue compatible property is good, Small side effects as a kind of natural products, in anti-tumor agent
Increasingly it is valued by people in research.Thus, being found from natural products has malignant melanoma cell Proliferation Ability
The compound of effect, there is application value for the malignant mela noma medicine for developing high-efficiency low-toxicity.
Epigynum Auritum（Epigynum auritum）It is a kind of Apocynaceae Epigynum Auritum race Simao Calamus, originates in Yun Nannan
Portion, according to the result of study of our early stages, the C that more structure is novel is contained in Epigynum Auritum21Steroidal and its glucoside compound.
It was found that under the interest drive of new drug lead compound, it is real that we have carried out substantial amounts of bioactivity screening to these noval chemical compounds
Test, it is found that the slotting oxygen pregnane glucoside compound of one of D- rings has under 25 μ g/mL concentration and significantly suppress pernicious
Melanoma cells（UACC-62）The activity of propagation.Pregnane glucoside compound provided by the invention and its conduct are anti-pernicious
Melanoma medicine has not yet to see report.
The content of the invention
It is an object of the invention to provide the D- rings shown in formula I to insert oxygen pregnane glycoside compounds：
Formula I：3β-15-O-16- pregn-5-ene-20-carbonyl 3-O-2′-methoxy-6-deoxy-β-D-
idopyranose；Epigynoside H, Chinese are entitled：3β-15-O- 16- pregnane -5 (6)-alkene -20- carbonyls 3-O- 2 '-first
Epoxide -6 '-deoxidation -β- D- idose glycosides, popular name are that Epigynum Auritum glycosides is pungent.
The present invention is another object is that by above-claimed cpd 3β-15-O- 16- pregnane -5 (6)-alkene -20- carbonyls 3-O-2′-
Methoxyl group -6 '-deoxidation -β- D- idose glycosides is applied in anti-malignant mela noma medicine is prepared, i.e., as suppression melanoma
Cell growth, the medicine of division or the medicine as melanoma chemotherapy.
One or more pharmaceutically acceptable auxiliary materials can also be added in application of the present invention, the auxiliary material includes medicine
Field conventional filler, diluent, adhesive, excipient, sorbefacient, filler, surfactant and stabilizer
Deng can also add flavouring agent, pigment and sweetener etc. if necessary.
Pill, pulvis, tablet, granula, oral liquid and injection can also be made in addition to capsule is made in application of the present invention
The diversified forms such as liquid.
The compounds of this invention 3β-15-O- 16- pregnane -5 (6)-alkene -20- carbonyls 3-O- 2 '-methoxyl group -6 '-deoxidation -β-
D- idoses glycosides has obvious inhibitory action to melanoma cells propagation, compared with the positive controls for being not added with the compound
There is significant difference.
Embodiment
The present invention is described in further detail below by embodiment, but present disclosure is not limited thereto, this
Method operating according to a conventional method unless otherwise specified in embodiment, agents useful for same unless otherwise specified use conventional commercial
Reagent or the reagent configured according to a conventional method.
Embodiment 1：The pungent preparation of pregnane glycoside compounds Epigynum Auritum glycosides
11 kg Simaos rattan samples after air-drying, extracted 3 times with methanol eddy after crushing, recycling design, be concentrated into small size,
It is extracted with ethyl acetate again 3 times, concentration ethyl acetate layer is weighed to obtain 110g；Ethyl acetate layer macroporous absorbent resin D101 is entered
Row rough segmentation, with the methanol-water of percent by volume 40%, 60%, 80%, 100% elute 4 part (Fr.A- is always obtained respectively
D)；Fr.B (25.7g) carries out gradient elution with methanol-water 20%, 40%, 60%, 80% by compression leg in C18 and obtains four parts
Fr. C1-C4；Fr. C2（1.2g）Pass through Sephadex LH-20（Mobile phase is chloroform：Methanol=1:1）Elution, then passes through C18
Formula is prepared in middle compression leg and half preparation liquid phaseIn Epigynum Auritum glycosides H（20mg）；Identified, the compound is noval chemical compound；
Qualification result is as follows：
Epigynum Auritum glycosides is pungent（Epigynoside H）For white powder, chloroform methanol mixed liquor is dissolved in（Chloroform：Methanol=1:1）, pyrrole
Pyridine etc..[α]26 D – 40.1 (c 0.1, MeOH); UV (MeOH) λ max (log ε): 203 (2.32)nm; IR
(KBr) ν max 3485 2935,1705,1635,1449,1137,1023,962 cm–1;HRESIMS m/z515.2990
[M+Na]+ (calcd. for C28H44O7Na+, 515.2985). 1H NMR (CDCl3, 500Mz) and13C NMR(CDCl3,
125Mz) it is shown in Table 1；Data above combination 2D NMR analyses confirm that Epigynum Auritum glycosides is pungent（epigynoside H）Chemical constitution
Formula is shown in formula I.
Qualification result is as follows：
Epigynum Auritum glycosides H（Epigynoside H）For white powder, chloroform methanol mixed liquor is dissolved in（Chloroform：Methanol=1:1）, pyridine
Deng.[α]26 D – 40.1 (c 0.1, MeOH); UV (MeOH) λ max (log ε): 203 (2.32)nm; IR (KBr)ν max 3485 2935,1705,1635,1449,1137,1023,962 cm–1;HRESIMS m/z515.2990 [M+Na]+
(calcd. for C28H44O7Na+, 515.2985). 1H NMR (CDCl3, 500Mz) and13C NMR(CDCl3, 125Mz) see
Table 1；Data above combination 2D NMR analyses confirm Epigynum Auritum glycosides H（epigynoside H）Chemical structural formula for shown in formula I.
Table 1：Epigynum Auritum glycosides H's1H NMR and13C NMR datas
。
Embodiment 2：Antitumor detection experiment
1st, material
DMSO（Sigma Co., USA）, hyclone（HyClone companies of the U.S.）, RPMI-1640 nutrient solutions（U.S. HyClone
Company）, phosphate buffer（Shanghai beyotime companies）, it is dual anti-（HyClone companies of the U.S.）、CCK-8（Eastern Renhua subject skill
Co., Ltd）, the present embodiment sample and dexamethasone are prepared with DMSO.
2nd, method
Melanoma（UACC-62）Cell RPMI-1640（Containing 10%FBS）Culture, treat that cell growth, will be thin to logarithmic phase
Born of the same parents digest, and add fresh medium suspension cell, and cell count simultaneously uses the survival rate of desk tray indigo plant Determination Staining cell, survival
Rate=uncolored cell number/TCS × 100%, survival rate ＞ are used to test, and cell suspension is adjusted to 1 × 106It is individual
/mL；If cell blank control group, positive controls（Dexamethasone）And sample sets（Concentration is set to 25 μ according to trial test result
mol·L-1, the DMSO containing isoconcentration）.After cultivating 72h, CCK-8 methods measure cell OD values.
Experimental data OD values represent that mathematical statistics and variance analysis work use using " average ± standard deviation "
Origin softwares are completed.
Cell survival rate（%）=sample sets A averages/normal group A average × 100%；
3rd, experimental result
The compounds of this invention can induce melanoma cells dead, find 3 β -15- firstO- 16- pregnane -5 (6)-alkene -20-
Carbonyl 3-O- 2 '-methoxyl group -6 '-deoxidation -β- D- idoses glycosides has obvious inhibition to melanoma cells propagation, carefully
Born of the same parents' survival rate is down to 54.6% from 100%, and the medicine of anti-tumor aspect will be prepared available for future, the results are shown in Table 2：
Table 2：The influence that the compounds of this invention is bred to melanoma cells
Significance analysis shows that Epigynum Auritum glycosides is pungent significant difference compared with dexamethasone（*p< 0.05）.
Claims (2)
1. D- ring of the structural formula as shown in formula I inserts oxygen pregnane glycoside compounds：
Formula I：3β-15-O- 16- pregnane -5 (6)-alkene -20- carbonyls 3-O- 2 '-methoxyl group -6 '-deoxidation -β- D- idose glycosides.
2. the D- rings described in claim 1 insert oxygen pregnane glycoside compounds answering in anti-malignant mela noma medicine is prepared
With.
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| CN108558975A (en) * | 2018-04-26 | 2018-09-21 | 昆明理工大学 | 12 beta-hydroxies-androstane-14,14- diene -16- ketone compounds and its application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558975A (en) * | 2018-04-26 | 2018-09-21 | 昆明理工大学 | 12 beta-hydroxies-androstane-14,14- diene -16- ketone compounds and its application |
| CN108558975B (en) * | 2018-04-26 | 2021-03-02 | 昆明理工大学 | 12 beta-hydroxy-androstane 4, 14-diene-16-ketone compound and application thereof |
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