CN106543159B - Epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity and the preparation method and application thereof - Google Patents
Epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity and the preparation method and application thereof Download PDFInfo
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- CN106543159B CN106543159B CN201610988136.7A CN201610988136A CN106543159B CN 106543159 B CN106543159 B CN 106543159B CN 201610988136 A CN201610988136 A CN 201610988136A CN 106543159 B CN106543159 B CN 106543159B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses new epoxy type annonaceous acetogenins with anti-tumor activity, the present invention is by carrying out system further investigation to sugar apple seed chemical component, show the isolated new epoxy type Annonaceousacetogenicompounds compounds from sugar apple seed by wave spectrum and MASS SPECTRAL DATA ANALYSIS, and show by internal and external antitumor activity, epoxy type Annona lactone provided by the invention is to kinds of tumor cells, including lung cancer, breast cancer, liver cancer etc. all has very strong anti-tumor activity, and to mouse transplantability hepatoma HepG2 and murine sarcoma S180Entity tumor also has an apparent inhibitory activity, and is a kind of excellent antitumoral compounds by toxicity test studies have shown that epoxy type Annonaceousacetogenicompounds compounds toxicity provided by the invention is lower.
Description
Technical field
The present invention relates to compounds with anti-tumor activity, and in particular to new epoxy type kind litchi with anti-tumor activity
Branch lactone compound and its purposes in prevention and treatment tumor disease, belong to pharmaceutical technology field.
Background technique
Malignant tumour is to seriously endanger the frequently-occurring disease and common disease of human health and life, before 2000~3000 years angstrom
And with China about the record of tumour.Many countries including China, especially medium-developed country, malignant tumour
Caused death account for the first or second in all causes of death, and disease incidence is worldwide still in rising trend, swollen
The art treatment of tumor, radiotherapy, chemotherapy, in the big therapy of biological therapy four, chemotherapy is still main treatment method, it is well known that existing
Chemotherapy medicine antitumor limited activity, and toxic side effect is larger, and patient's tolerance is poor, and expensive.Therefore, by grinding
Study carefully the occurrence and development of the pre- anti-cancer of chemical anti-cancer substance in natural plants, it has also become a weight of cancer chemoprevention research
Field is wanted, and common concern and research hotspot by countries in the world scientific circles.
Annona lactone is that one kind extracts isolated native compound, Annonaceousacetogenicompounds from Annonaceae plant
Compound has extensive bioactivity, most typically desinsection and Anti-tumor angiogenesis, and researches show that Annona lactones to exist
Inside and outside has powerful cytotoxicity, and preferable bioactivity is all shown to kinds of tumor cells, research shows that
The mechanism of action of Annona lactone anti-tumor activity is by blocking mitochondria NADH oxidoreducing enzyme, to prevent respiratory chain electric
The transmitting of son inhibits the generation of tumour cell ATP, keeps tumour cell dead due to starvation, and mechanism of action is unique, is different from one
As anti-tumor drug mechanism of action, be called " Star of Anticancer tomorrow ".
Sugar apple seed is the waste abandoned after manaca pulp is edible, wherein Annonaceousacetogenicompounds compounds content compared with
Height makes it turn waste into wealth to make full use of this waste, and the present invention carries out system to sugar apple seed chemical component and gos deep into
Research, the isolated 1 new epoxy type Annonaceousacetogenicompounds compounds from sugar apple seed.
Summary of the invention
Goal of the invention: a kind of living with powerful antitumor the purpose of the invention is to overcome the deficiencies of the prior art and provide
Property new epoxy type Annonaceousacetogenicompounds compounds and its prevent and treat tumor disease in purposes.Another mesh of the invention
The preparation method for being to provide the epoxy type Annonaceousacetogenicompounds compounds.
Technical solution: in order to achieve the goal above, the technical scheme adopted by the invention is as follows:
Epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity, which is characterized in that its structural formula is as follows:
Molecular formula is C35H60O4。
Preferably, above-described epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity, by ring
Oxygen type Annonaceousacetogenicompounds compounds and pharmaceutically acceptable carrier be prepared into tablet, capsule, injection, powder-injection,
Granula, fat emulsion, micro-capsule, dripping pill, pill, ointment or skin-permeable and control-released plaster dosage form drug.
When tablet is made in epoxy type Annona lactone provided by the invention, epoxy type Annona lactone and lactose or jade
Magnesium stearate lubricant is added in rice starch when needing, be uniformly mixed, whole grain, then tablet is made in tabletting.
When capsule is made in epoxy type Annona lactone provided by the invention, epoxy type Annona lactone and carrier lactose
Or cornstarch is uniformly mixed, whole grain is then encapsulated that capsule is made.
When granule is made in epoxy type Annona lactone provided by the invention, epoxy type Annona lactone and diluent cream
Sugar or cornstarch are uniformly mixed, whole grain, dry, and granule is made.
When powder-injection is made in epoxy type Annona lactone provided by the invention, epoxy type Annona lactone is freeze-dried,
Sterilization, is made powder-injection.
When injection is made in epoxy type Annona lactone provided by the invention, take epoxy type Annona lactone that physiology salt is added
Water dissolution then be added activated carbon, stir evenly, 80 DEG C heat 30 minutes, filtering, adjust pH value, with sintered glass funnel or its
Its filter is filtered to clear and bright, filling, sterilizes 30 minutes at 100 to 115 DEG C and injection is made.
When the dosage forms such as fat emulsion, ointment or skin-permeable and control-released plaster are made in epoxy type Annona lactone provided by the invention
Carrier is added to be prepared by pharmacy conventional method.
Epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity provided by the invention can be used for preparing anti-swollen
Tumor medicine.It is preferred for preparation treatment lung cancer, breast cancer, liver cancer, the drug of the tumor diseases such as cervical carcinoma and gastric cancer.
The preparation method of epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity of the present invention comprising
Following steps:
A. extract by solvents is used after taking sugar apple seed, decladding to crush, and is recycled extracting solution, is obtained concentrate；
B. concentrate is separated by chromatography, obtains target compound.
Preferably, the preparation of above-described epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity
Method, Extraction solvent are one of petroleum ether, chloroform, ethyl acetate or their mixed solvent.It is preferred that chloroform.
Preferably, the preparation of above-described epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity
Method, extracting method are infusion process, percolation, microwave loss mechanisms or ultrasonic extraction, preferably diacolation and ultrasonic extraction.
Preferably, the preparation of above-described epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity
The material of method, the chromatography separation is silica gel, aluminium oxide or octadecyl silane.Wherein preferred silica gel is used
The petroleum ether of different volumes ratio, ethyl acetate and methanol are collected as eluent, elution respectively containing the elution of target compound
Liquid concentration, respectively obtains refined liquid.
Refined liquid after concentration respectively can be again with carrying out color in the materials such as silica gel, aluminium oxide or octadecyl silane
Spectrum separation, collects the eluent containing object.It is respectively obtained in epoxy type manaca after eluent recrystallization or solvent evaporated
Esters noval chemical compound.
The utility model has the advantages that epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity provided by the invention and existing skill
Art is compared and is had the advantage that
The present invention is by carrying out system further investigation to sugar apple seed chemical component, by wave spectrum and MASS SPECTRAL DATA ANALYSIS
Show the isolated epoxy type Annonaceousacetogenicompounds compounds (referred to as: if folding general for Xining second) from sugar apple seed, is new
Compound.And show epoxy type Annona lactone provided by the invention to a variety of by internal and external antitumor activity
Tumour cell, including lung cancer, breast cancer, liver cancer all have very strong anti-tumor activity, and to mouse transplantability hepatoma HepG2
With murine sarcoma S180Entity tumor also has apparent inhibitory activity, and by toxicity test studies have shown that provided by the invention
Epoxy type Annonaceousacetogenicompounds compounds toxicity with anti-tumor activity is lower, is a kind of excellent antitumoral compounds.
The preparation method of epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity provided by the invention, technique are set
Meter is reasonable, strong operability, the epoxy type Annonaceousacetogenicompounds compounds purity is high being prepared.
Detailed description of the invention
If it is general for Xining second that Fig. 1 is that epoxy type Annonaceousacetogenicompounds compounds are folded1HNMR figure；
If it is general for Xining second that Fig. 2 is that epoxy type Annonaceousacetogenicompounds compounds are folded13C NMR figure；
If Fig. 3 is that epoxy type Annonaceousacetogenicompounds compounds fold the general high resolution mass spectrum figure for Xining second.
If Fig. 4 is that epoxy type Annonaceousacetogenicompounds compounds fold the general ESIMS/MS mass spectrogram for Xining second.
If Fig. 5 is that epoxy type Annonaceousacetogenicompounds compounds fold the general structural schematic diagram for Xining second.
Specific embodiment
According to following embodiments, the present invention may be better understood.However, as it will be easily appreciated by one skilled in the art that real
It applies specific material proportion, process conditions and its result described in example and is merely to illustrate the present invention, without that should will not limit
The present invention described in detail in claims processed.
The preparation of 1 epoxy type Annonaceousacetogenicompounds compounds of embodiment (if folding general for Xining second)
Dry sugar apple seed 10kg is taken, chloroform diacolation is used after crushing, recycling merges percolate, filtering, and filtrate decompression is returned
Receipts obtain concentrate 1kg, and concentrate carries out column chromatography for separation with purification on normal-phase silica gel, are washed with petroleum ether-ethyl acetate-methanol gradient
It is de-, 500 parts of fraction are collected altogether, and 12 parts (F1-F12) are merged into according to thin-layer chromatography situation.F3 (178.8 grams) is through positive
Silica gel column chromatography separation, with petroleum ether-ethyl acetate (20:1-0:1) gradient elution, if obtaining folding general for Xining second (1).Through height
Imitate liquid phase detection, purity 98.3%.
Structure elucidation: white powder, molecular formula: C35H60O4；Fusing point: 60-62 DEG C；Optical activity: [α]25 D+13.0(c 0.1,
EtOH)；It is ultraviolet: UV (MeOH) λmax(logε)208(3.93)nm；1HNMR and13C NMR data is shown in Table 1, Fig. 1 and 2；High-resolution
Electrospray ionization mass spectrum (HRESIMS): quasi-molecular ion peak m/z 545.4539 [M+H]+(calculated value 545.4570), mass spectrometric data
Such as Fig. 3, ESIMS/MS such as Fig. 4.It determines that relative molecular weight is 544 in conjunction with elemental analysis, determines that molecular formula is C35H60O4, compound
UVλmaxThe reaction of=208nm and keed reagent is in aubergine, illustrates there is α, the presence of β-γ unsaturated lactone ring.Its1δ in H-NMRH
7.01 (H-33), 5.01 (H-34), 1.43 (H-35) and13δ in C-NMRC 173.9(C-1)、134.3(C-2)、148.9(C-
33), 77.4 (C-34), 19.2 (C-35), these are the characteristic signals of α, β-γ unsaturated lactone ring；1δ in H-NMRH2.29 place
Triplet show C-4 without oxygen-containing group replace,1In H-NMR δ 2.94-3.00 multiplet (4H, H-11,12,15,
16) and13C-NMR δ 57.3 (C-11), 56.9 (C-12), 56.9 (C-15), the peak of 56.8 (C-16) show that there are two rings in structure
The presence of oxygen ring.δH5.38-5.48 multiplet (2H, H-19, H-20) and δC128.1 (C-19) and 131.2 (C-20) show to tie
With the presence of carbon-carbon double bond in structure.Two rings are inferred according to ESI-MS/MS data (m/z=209,251,265,279,307,319)
The position of substitution of oxygen ring is C-11 and C-12 and C-15 and C-16.According to ESI-MS/MS data (m/z=349,375), carbon is inferred
Carbon double bond is in C-19 and C-20.It identifies that the compound is the ring-like manaca branch lactone compound of a new epoxy, is named as
If folding general for Xining second, structural formula is as shown in Figure 5.
The NMR data of 1 epoxy type Annonaceousacetogenicompounds compounds of table (if folding general for Xining second)
The acute toxicity testing of 2. epoxy type Annonaceousacetogenicompounds compounds of embodiment (if folding general for Xining second).
Mouse median lethal dose LD is calculated by Bliss method50Value, measurement result are as follows:
2. acute toxicity testing data of table
By experiment gained LD50If to fold the general acute toxicity for Xining second lower for value explanation, in three kinds of administration routes, take orally to
The toxicity of medicine reflects minimum, and more sensitive amount-effect (death) relationship is presented since drug is rapidly reached each device pipe in intravenous injection.
Embodiment 3: in vitro to the inhibiting effect of human tumor cells.
With drug-resistant tumor strain: human breast carcinoma (MCF-7/ADR), human liver cancer (SMMC-7721/T), human lung cancer (A549/T) 3
Kind of tumor line carries out anticancer experiment in vitro using thiazolyl blue reduction method (MTT), if the folding of being prepared of embodiment 1 is general for west
Ning Yi sets 6 concentration, using cis-platinum as positive controls, using solvent, that is, dimethyl sulfoxide of sample as negative control group.By the reality of table 3
General different inhibiting effect, anticancer experiment in vitro are shown to 3 plants of human tumor cells for Xining second if testing result and can be seen that fold
Statistics indicate that if provided by the invention fold general shows more stronger than positive drug cis-platinum cell selection inhibitory activity for Xining second.
If table 3 folds the general inhibiting effect for Xining second to 3 plants of cells of resistant tumors.
Embodiment 4: in vivo to the inhibiting effect of mouse transplantability hepatoma HepG2 growth.
The Inhibition test of mouse interior tumor growth is carried out with mouse transplantability hepatoma HepG2, what embodiment 1 was prepared
If fold it is general set 3 dosage groups respectively for Xining second, i.e., it is 3 groups high, medium and low, using taxol as positive controls, with the solvent of sample
(soybean oil) is negative control group, and every group sets 10 mouse, every group of mouse peritoneal injection daily 200 μ L, continuous 7 days, in the 8th
It puts to death mouse, takes tumour, weighs, and calculating tumour inhibiting rate the results are shown in Table 4.
Inhibition assay result of 4 intraperitoneal administration of table to rat liver cancer HepG2
Tumour inhibiting rate (%)=(1- medicine group knurl weight/feminine gender organizes knurl weight) × 100%, * gives the molten of equal amount sample dissolution
Liquid, similarly hereinafter.
The general inhibitory activity powerful to mouse hepatoma HepG2 growth display for Xining second is folded if being obtained by experimental result table 4,
High concentration group is 60.9% to mouse hepatoma HepG2 inhibiting rate, close to the positive drug taxol of same concentrations.
Embodiment 5: in vivo to mouse transplanted sarcoma S180The inhibiting effect of growth.
With murine sarcoma S180Carry out mouse interior tumor growth Inhibition test, if embodiment 1 be prepared fold general replace
Xining second respectively sets 3 dosage groups, i.e., 3 groups high, medium and low, using taxol as positive controls, is with solvent, that is, soybean oil of sample
Negative control group, every group sets 10 mouse, and every group of mouse peritoneal is injected 200 μ L continuous 7 days daily, in the 8th day execution mouse,
Tumor is taken, is weighed, calculating tumour inhibiting rate the results are shown in Table 5.
5 intraperitoneal administration of table is to small rat meat cancer S180Inhibiting rate
Tumour inhibiting rate (%)=(1- medicine group knurl weight/feminine gender organizes knurl weight) × 100%；* the molten of equal amount sample dissolution is given
Liquid, similarly hereinafter.
If obtained by experimental result table 5 fold it is general for Xining second to mouse hepatosarcoma S180Also show certain inhibitory activity, phase
High for feminine gender group, middle concentration group all has statistical significance, and high concentration group is to murine sarcoma S180Inhibiting rate also shows for 39.0%
Show preferable antitumor activity.The above anti-tumor experiment in vivo further illustrates that compound provided by the invention is swollen with highly resistance
Tumor activity, less toxic side effect.
Embodiment 6: the preparation of tablet
The preparation of tablet, if folding of taking that above-described embodiment 1 obtains is general to add appropriate pharmaceutic adjuvant starch, a small amount of hard for Xining second
Fatty acid magnesium mixes well, tabletting, is administered orally if being made every and folding the general tablet for Xining second containing 1mg.
Embodiment 7: the preparation of capsule
The preparation of capsule, if folding of taking that above-described embodiment 1 obtains is general for Xining second, dosing supplementary product starch is appropriate, fills
Divide and mix, is packed into capsule, is administered orally if being made every and folding the general capsule for Xining second containing 1mg.
Embodiment 8: injection
The preparation of injection is made if folding of taking that above-described embodiment 1 obtains is general to add water for injection, appropriate glycerol for Xining second
If folding the general injection for Xining second containing 0.25mg at every 250ml to use for intravenous drip.
Embodiment 9: the preparation of micro-capsule
The preparation of microcapsule formulation: taking gelatin appropriate, if it is general for Xining second, distilled water that the folding of obtaining of above-described embodiment 1 is added
Colostrum is made in right amount, and emulsion is made in right amount with 3% Arabic glue, 3% gelatin solution is added when emulsion is heated to 45 degree
It is appropriate and use 10% acetate solution tune pH4.1-4.3, it is added that distilled water, 3% formaldehyde are appropriate, and stirring makes its solidification shape, with 5% hydrogen
Sodium oxide molybdena tune pH7.0-7.2 is eventually adding appropriate 10% starch solution, if being made every gram folds the general micro-capsule for Xining second containing 1mg.
The technical concepts and features of embodiment of above only to illustrate the invention, its object is to allow be familiar with technique
People understands the content of present invention and is implemented, and it is not intended to limit the scope of the present invention, and all spirit according to the present invention is real
The equivalent change or modification that matter is done, should be covered by the scope of protection of the present invention.
Claims (4)
1. epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity, which is characterized in that its structural formula is as follows:
2. a kind of drug with anti-tumor activity, which is characterized in that by ring with anti-tumor activity described in claim 1
Oxygen type Annonaceousacetogenicompounds compounds and pharmaceutically acceptable carrier are prepared into tablet, capsule, injection, granule, rouge
Fat emulsion, micro-capsule, pill or skin-permeable and control-released plaster dosage form drug.
3. epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity described in claim 1 are in preparation anti-lung cancer, cream
Application in gland cancer, liver-cancer medicine.
4. the preparation method of epoxy type Annonaceousacetogenicompounds compounds with anti-tumor activity described in claim 1, special
Sign be the following steps are included:
A, extract by solvents is used after taking sugar apple seed, decladding to crush, and is recycled extracting solution, is obtained concentrate；
B, concentrate is separated by chromatography, obtains target compound；
Extraction solvent is one of petroleum ether, chloroform, ethyl acetate or their mixed solvent；
Extracting method is infusion process, percolation, microwave loss mechanisms or ultrasonic extraction；
The material of the chromatography separation is silica gel, aluminium oxide or octadecyl silane.
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| CN107674065A (en) * | 2017-10-13 | 2018-02-09 | 江苏建康职业学院 | Annonaceous acetogenins and its application with antitumor activity |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1445220A (en) * | 2003-04-21 | 2003-10-01 | 深圳中药及天然药物研究中心 | Lactone category compound of sweetsop as well as new usage in medicines and its preparing method |
| CN1861597A (en) * | 2006-06-16 | 2006-11-15 | 南京中医药大学 | Internal ester monomer compound and its application in preparing anti cancer medicine |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1445220A (en) * | 2003-04-21 | 2003-10-01 | 深圳中药及天然药物研究中心 | Lactone category compound of sweetsop as well as new usage in medicines and its preparing method |
| CN1861597A (en) * | 2006-06-16 | 2006-11-15 | 南京中医药大学 | Internal ester monomer compound and its application in preparing anti cancer medicine |
Non-Patent Citations (3)
| Title |
|---|
| Annonaceous acetogenins: Precursors from the seeds of Annona squamosa;Idensi Bajin ba Ndob et al.;《Phytochemistry Letters》;20081209;第2卷;第72-76页 |
| 番荔枝内醋结构类型及作用机制研究进展;张帅等;《西北农林科技大学学报（自然科学版）》;20051231;第33卷(第12期);第21-26页 |
| 番荔枝种子中的3个新的番荔枝内酯;郑祥慈等;《植物学报》;19951231;第37卷(第3期);第238-243页 |
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