CN106943396A - Applications of the water ghost new alkali A of any of several broadleaf plants in antineoplastic is prepared - Google Patents
Applications of the water ghost new alkali A of any of several broadleaf plants in antineoplastic is prepared Download PDFInfo
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- CN106943396A CN106943396A CN201710354463.1A CN201710354463A CN106943396A CN 106943396 A CN106943396 A CN 106943396A CN 201710354463 A CN201710354463 A CN 201710354463A CN 106943396 A CN106943396 A CN 106943396A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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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)
- A61K36/88—Liliopsida (monocotyledons)
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Abstract
The invention belongs to pharmaceutical technology field, and in particular to the application of isolated new alkaloid compound in a kind of terrible any of several broadleaf plants bulb from vegetation water.Shown in the structural formula of compound involved in the present invention such as formula (I).Involved application is to be used to prepare antineoplastic on above-claimed cpd.The compound has the obvious effect for suppressing tumour；And prepare the compound raw material resources enrich, extraction and separation technology difficulty is small, and solvent is recyclable, and production cost is low.
Description
The application is application number 201510868700.7,01 day December 2015 applying date, a kind of denomination of invention " new chemical combination
The divisional application of thing and its application ".
Technical field
The invention belongs to pharmaceutical technology field, and in particular to isolated new biology in a kind of terrible any of several broadleaf plants bulb from vegetation water
The application of alkaloid compound.
Background technology
Water ghost any of several broadleaf plants (Hymenocallis littoralis), also known as America Hymenocallis americana, are perennial bulb herbaceous plant.
Just like chela crab leg, spider pin, therefore there are " chela crab flower ", the title of " water ghost any of several broadleaf plants ".Flower is white, there is fragrance.Florescence summer and autumn, capsule ovum
Circular or annular, meat shape splits when ripe.Seed is spongioplasm shape, green.Water ghost any of several broadleaf plants originates in american torrid zone area, west print
Spend archipelago.The area such as Fujian China, Guangdong, Guangxi, Yunnan introducing and planting.While possessing ornamental value, also possess certain
Medical value, its bulb can be used as medicine, be clinically used for relaxing the muscles and stimulate the blood circulation, swelling and pain relieving.For rheumatic arthritis, paronychia is fallen
Beat and swell and ache, ulcer, hemorrhoid etc..Research is found, abundant alkaloid compound is contained in its bulb.
Root is it is reported that the main bulb using the terrible any of several broadleaf plants of water, as research object, alkaloid, Huang is mainly contained in the terrible any of several broadleaf plants bulb of water
Ketone compounds, research shows that alkaloid has good antitumor, anti-inflammatory activity.
We have carried out the chemical constitution study of system to the terrible any of several broadleaf plants of water gathered from Guangxi, to its clear and definite chemical composition,
For Natural Medicine Chemistry research stockpile；It was found that the natural products with excellent activity, is that follow-up in-depth study exploitation is carried
For material base.
The content of the invention
It is an object of the invention to provide a kind of new compound and its application in anti-inflammatory, antineoplastic is prepared.
The present invention is to extract a kind of isolated new biology from terrible any of several broadleaf plants (the being grown on Guangxi China Guigang) bulb of water
Alkaloid compound, is named as the water ghost new alkali A of any of several broadleaf plants its chemical structural formula (I) as follows：
The preparing raw material aboundresources of the compound of the present invention, extraction and separation technology difficulty is small, and solvent is recyclable, raw
Produce low cost.
The preparation method of above-claimed cpd is as follows：
(1) extract：By the bulb chopping of the terrible any of several broadleaf plants of water, dry in the shade, alkalized with concentration for 1% soaking with sodium hydroxide, during alkalization
Between be 1 hour, then take out the terrible any of several broadleaf plants bulb of water and dry, with dichloromethane temperature leaching method extraction 3 times, every time 2 hours；Merge and extract
Liquid, medicinal extract is concentrated under reduced pressure into extract solution.
(2) separate：By above-mentioned medicinal extract application silica gel column chromatography, using volume ratio as 15:1-3:1 chloroform-methanol system ladder
Degree elution, thin-layer chromatography detection, collects the flow point containing noval chemical compound, then through ODS reversed phase column chromatographies, using volume ratio as 3:7-5:
5 methanol-water is eluted, and most preparing liquid phase through C18 reversed phase column chromatographies afterwards prepares, using volume ratio as 4:6 methanol-water is carried out
Elution, obtains the new alkali A of the terrible any of several broadleaf plants of noval chemical compound water.
The novel compound of present invention water ghost new alkali A of any of several broadleaf plants, Yellow amorphous powder, HR-ESI-MS is at m/z 298.1070
Provide [M+H]+Peak, is provided [2M+Na] at m/z 617.1861+Peak, it is C to calculate its molecular formula17H15NO4,1H and13C nuclear-magnetisms
Resonance data is as shown in table 1.
Experimental researches prove that, compound on tumor of the invention has obvious inhibitory action.It therefore, it can be used to prepare
Antineoplastic.In addition, the compound on inflammation also has obvious inhibitory action, it therefore, it can be used to prepare anti-inflammatory drug.
The new alkali A's of the water of table 1 ghost any of several broadleaf plants1H and13C nuclear magnetic resonance datas
The new alkali A structure elucidations of noval chemical compound water ghost any of several broadleaf plants
As shown in figs. 1-7, noval chemical compound of the present invention1H NMR、13C NMR, 2D-NMR (COSY, HSQC, HMBC and
ROSEY) compose, and HR-ESI-MS spectrums learn compound structure.Specifically：
1H-NMR(400MHz,DMSO-d6) in spectrum, δ：8.05 (1H, d, J=8.0Hz), 7.82 (1H, d, J=8.0Hz),
There are a 1,2 adjacent dibasic phenyl ring pieces in 7.59 (1H, t, J=7.3Hz), 7.53 (1H, t, J=7.3Hz), prompting structure
Section；δ：7.67 (1H, s), 7.03 (1H, s), in the presence of the phenyl ring fragment of an AA ' BB ' substitution in prompting structure；δ：5.81(1H,
D, J=14.3Hz), 4.68 (1H, d, J=14.4Hz), 3.85 (2H, dd, J=15.2,25.2Hz) are present in prompting structure
2*-CH2- fragment；δ：3.65 (3H, s), in the presence of a methyl being connected with electron-withdrawing group in prompting structure.
13C-NMR(100MHz,DMSO-d6) spectrum provide 17 carbon signals, wherein δC163.0 be carbonyl carbon signals.δC：
148.8th, 148.2,140.8,130.1,129.0,127.3,125.5,123.3,121.5,120.6,108.1,104.5 prompting knot
12 SP are there may be in structure2The carbon atom of hydridization；δC63.5th, it there may be and electron-withdrawing group in 60.6,49.9 prompting structures
The carbon atom of connection.
Hsqc spectrum provides the information that all hydrogen carbon are joined directly together in structure, as shown in table 1.δH6.15 and δC101.8 is related
- O-CH is there may be in prompting structure2- O- fragments；δH3.65 and δC49.9 is related, and-N-CH is there may be in prompting structure3- piece
Section.
In HMBC spectrums, aromatic signal δH7.67 and δC148.8th, 121.5 is related, aromatic signal δH7.03 and δC148.2nd, 123.3 is related, and methene proton signal δH6.15 and δC148.8th, 148.2 is related, points out the presence of structure fragment
A1 (as shown in Figure 8)；Aromatic signal δH8.05 and δC140.8th, 130.1,123.3 is related, aromatic signal δH7.82
With δC130.1st, 129.0 is related, aromatic signal δH7.59 and δC129.0th, 127.3,120.6 is related, aromatic signal
δH7.53 and δC140.8th, 125.5,104.5 is related, N-methyl proton δH3.65 and δC140.8th, 63.5,60.6 is related, methylene
Proton signal δH3.85 and δC163.0th, 60.6,49.9 is related, methene proton signal δH5.81 and δC140.8、123.3、
121.5 is related, methene proton signal δH4.68 and δC140.8th, 123.3,121.5,63.5 is related, points out the presence of structure fragment
A2 (as shown in Figure 8).Structure fragment A1 and A2 part are linked together, compound A planar structure is finally determined.
H-11 and H-15,13 related in NOESY spectrums, H-2 is related to H-14a, 14b, H-14a and H-14b, 13 related, really
The relative configuration of the compound is determined.The compound is the neoformation alkaloid compound for having no document report, and related NMR data is returned
Category is as shown in table 1.
Brief description of the drawings
Fig. 1 noval chemical compounds1H H NMR spectroscopies；
Fig. 2 noval chemical compounds13C H NMR spectroscopies；
The COSY spectrums of Fig. 3 noval chemical compounds；
The hsqc spectrum of Fig. 4 noval chemical compounds；
The HMBC spectrums of Fig. 5 noval chemical compounds；
The ROSEY spectrums of Fig. 6 noval chemical compounds；
The HR-ESI-MS spectrums of Fig. 7 noval chemical compounds；
The structure fragment of Fig. 8 noval chemical compounds；
Fig. 9 noval chemical compounds influence on the in-vitro multiplication inhibitory action of human body tumour cell.
Embodiment
The invention is further illustrated by the following examples, this professional technique is more fully understood the present invention, but not with
Any mode limits the present invention.
Embodiment 1：Water ghost any of several broadleaf plants (Hymenocallis littoralis) bulb, chopping, dry in the shade the 7.5kg that weighs, and uses concentration
Alkalized for 1% soaking with sodium hydroxide, alkalization time is 1 hour, then take out the terrible any of several broadleaf plants bulb of water and dry, soaked with dichloromethane temperature
Method is extracted 3 times, and the consumption that dichloromethane is extracted every time is 30L, and each extraction time is 2 hours；Merge extract solution, to extract solution
Medicinal extract is concentrated under reduced pressure into, medicinal extract 78g is obtained；Above-mentioned medicinal extract is mixed with 80g silica gel and mixes sample, using silica gel column chromatography, with volume
Than for 15:1-3:1 chloroform-methanol system gradient elution, thin-layer chromatography detection, collected volume ratio is 15:1-3:1 flow point,
Again through ODS reversed phase column chromatographies, using volume ratio as 3:7-5:5 methanol-water is eluted, and collects eluent, most anti-phase through C18 afterwards
Column chromatography prepares liquid phase and prepared, isocratic elution, and mobile phase is methanol-water (40：60), flow velocity is 3ml/min, Detection wavelength
210nm, 25 DEG C of column temperature obtains the new alkali A sterlings 177mg of the terrible any of several broadleaf plants of noval chemical compound water.
Embodiment 2：The new alkali A of noval chemical compound water ghost any of several broadleaf plants cytotoxic activity experiment
1st, experiment material
1.1st, given the test agent
The water ghost new alkali A DMSO of any of several broadleaf plants dissolve, and add solution or uniform suspension that PBS is made into 1000 μ g/ml, Ran Houyong
PBS dilutions containing DMSO.
1.2nd, cell line
A549 (human lung carcinoma cell), LOVO (people's colon-cancer cell), MCF-7 (human breast cancer cell), HL-60 (human leukemias
Cell), HepG-2 (human liver cancer cell).
1.3rd, nutrient solution
Comprising RPMI1640,15%NBS, dual anti-.
1.4th, other materials
ELIASA, 96 well culture plates.
2nd, test method
Mtt assay：It is 1 × 10 that 96 orifice plates, which add concentration per hole,5Individual/ml μ the l of cell suspension 100, are placed in 37 DEG C, 5%CO2Training
Support in case.After 24h, addition sample liquid, 10 μ l/ holes, if 6 multiple holes, 37 DEG C, 5%CO2Effect 48h in incubator.Added per hole
Lysate is added after the 5mg/ml μ l of MTT solution 20, effect 4h, 100 μ l/ holes are put in incubator, surveyed after dissolving with ELIASA
570nmOD values.
3rd, result of the test
As a result see Fig. 9, as a result show, the water ghost new alkali A of any of several broadleaf plants to A549 (human lung carcinoma cell), LOVO (people's colon-cancer cell),
MCF-7 (human breast cancer cell), HL-60 (human leukemia cell) and HepG-2 (human liver cancer cell), which to have preferably suppress, to live
Property, the water ghost new alkali A of any of several broadleaf plants has good antitumor action, with good DEVELOPMENT PROSPECT.
Embodiment 3：Clinical trials of the noval chemical compound water ghost new alkali A of any of several broadleaf plants to mouse S 180 sarcoma (solid type)
1st, experiment material
1.1st, given the test agent
The water ghost new alkali A of any of several broadleaf plants after a small amount of Tween-80 hydrotropy with using 0.5%CMC wiring solution-formings.
1.2nd, animal
Strain：Kunming mouse
Body weight：20±2g
1.3rd, transplanted tumor
Mouse S 180 sarcoma
2nd, test method
Well-grown mouse S 180 sarcoma ascites is taken, with physiological saline with 1:4 dilutions, every mouse armpit subcutaneous vaccination
0.2ml, random packet is divided into control group, endoxan group (CTX groups, 20mg/kg, ip × 7), the new alkali A (5mg/kg) of the terrible any of several broadleaf plants of water
It is administered after group, inoculation from next day, administered volume is 0.5ml/20g body weight, continuous gavage 7 days.De- neck on the 10th puts to death dynamic after inoculation
Thing, claims solution after the weight of animals to take tumor mass, claims knurl weight.Result judgement is according to below equation：
3rd, experimental result
The water ghost new alkali A of any of several broadleaf plants has significant tumor inhibition effect, and experimental result is shown in Table 2.
Inhibitory action of the noval chemical compound water of the table 2 ghost new alkali A of any of several broadleaf plants to mouse S 180 sarcoma
Compared with control group：* P ＜ 0.05, * * P ＜ 0.01.
Embodiment 4：The new alkali A anti-inflammatories experiment mice ear swelling model of noval chemical compound water ghost any of several broadleaf plants
1st, experimental animal
Swiss kind mouse, body weight 20-24g
2nd, experimental model and method of testing
Mouse 50 is taken, 5 groups are randomly divided into, the dosage gastric infusion 3d as shown in table 3, in 1h after last dose, is used
The left ear of mouse is caused inflammation by 0.05ml dimethylbenzene, and with a diameter of 7mm card punch by the overlapping punching of ears, the disk of punching is existed
Weighed on a ten thousandth sensitivity balance, its swelling is represented with the weight difference of the disk of mouse ear two.
3rd, statistical analysis：
All experimentss result is represented with mean ± standard error.Examined with student t- and compare each group of data and blank
The significant difference of group, P ＜ 0.05 represent that difference has significant.
4th, result of the test：
The influence that the noval chemical compound water of the table 3 ghost new alkali A of any of several broadleaf plants is tested to mice ear
Compared with control group：* P ＜ 0.05, * * P ＜ 0.01.
As a result show, positive control drug hydrocortisone, the noval chemical compound water ghost new alkali A of any of several broadleaf plants cause to mice ear model
Inflammation have significant inhibitory action.
Embodiment 5：The new alkali A anti-inflammatories experimental rat carrageenan foot swelling model of noval chemical compound water ghost any of several broadleaf plants
1st, experimental animal
SD rats, male and female half and half, 200 ± 20g of body weight.
2nd, test model and detection method
Rat 50 is taken, 5 groups are randomly divided into, the dosage gastric infusion 4d as shown in table 4 is caused scorching with measurement before last dose
Preceding volume；30min after last dose, wastes time and 1% carrageenan 0.1ml cause inflammation is subcutaneously injected enough in rat right hind leg.Respectively at cause
2 after inflammation, 4,6h measure the right following volume of ankle-joint.
3rd, statistical analysis：
All experimentss result is represented with mean ± standard error.Examined with student t- and compare each group of data and blank
The significant difference of group, P ＜ 0.05 represent that difference has significant.
4 experimental results：
The influence that the noval chemical compound water of the table 4 ghost new alkali A of any of several broadleaf plants is tested rat carrageenan foot swelling
Compared with control group：* P ＜ 0.05, * * P ＜ 0.01.
As a result show, positive control drug dexamethasone, the water ghost new alkali A of any of several broadleaf plants are pitched caused by dish glue foot swelling model to rat
Inflammation has significant inhibitory action.
Embodiment 6：The new alkali A anti-inflammatories experiment mice abdominal cavity capillary permeability experiment of noval chemical compound water ghost any of several broadleaf plants
1st, experiment mice
NH systems mouse, male and female dual-purpose, 20 ± 2g of body weight.
2nd, experimental model and method of testing
Rat 50 is taken, random 5 groups of packet, the dosage gastric infusion 1h as shown in table 5, the physiology salt of tail vein injection 2%
Aqueous solution 0.1ml/10g body weight, the random acetic acid normal saline solution 0.2ml/ of abdominal cavity injection 0.8% only, is taken off at cervical vertebra after 20min
Dead mouse, with 5ml physiological saline fraction time washing abdominal cavity, 3000 revs/min, centrifuges 15min；Take supernatant ELIASA in
Its optical density (OD) value of 570nm colorimetric estimations.
3rd, statistical analysis：
All experimentss result is represented with mean ± standard error.Examined with student t- and compare each group of data and blank
The significant difference of group, P ＜ 0.05 represent that difference has significant.
4th, result of the test
The influence that the noval chemical compound water of the table 5. ghost new alkali A of any of several broadleaf plants is tested mouse peritoneal capillary permeability
Compared with control group：* P ＜ 0.05, * * P ＜ 0.01.
As a result show, positive control drug dexamethasone, the water ghost new alkali A of any of several broadleaf plants draw to the experiment of mouse peritoneal capillary permeability
The inflammation risen has significant inhibitory action.
Claims (1)
1. applications of the water ghost new alkali A of any of several broadleaf plants in antineoplastic is prepared, shown in the new alkali A of water ghost any of several broadleaf plants structural formula such as formula (I)：
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| CN201510868700.7A CN105481880B (en) | 2015-12-01 | 2015-12-01 | A kind of noval chemical compound and its application |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109893524A (en) * | 2019-04-30 | 2019-06-18 | 黑龙江中医药大学 | Application of the new alkali A of water ghost any of several broadleaf plants in prevention and treatment Alzheimer disease |
| CN113713028A (en) * | 2021-09-18 | 2021-11-30 | 海南鑫开源医药科技有限公司 | Composition with effect of inhibiting activity of tumor cells and application thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113209085B (en) * | 2021-06-23 | 2021-10-29 | 黑龙江中医药大学 | Application of novel aloperine A in preparation of antibacterial drugs |
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| CN101318966A (en) * | 2008-04-10 | 2008-12-10 | 中国人民解放军第二军医大学 | Dimerized sesquiterpenoids, preparation and application thereof |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109893524A (en) * | 2019-04-30 | 2019-06-18 | 黑龙江中医药大学 | Application of the new alkali A of water ghost any of several broadleaf plants in prevention and treatment Alzheimer disease |
| CN109893524B (en) * | 2019-04-30 | 2020-06-16 | 黑龙江中医药大学 | Application of canotoxin A in prevention and treatment of Alzheimer disease |
| CN111494368A (en) * | 2019-04-30 | 2020-08-07 | 黑龙江中医药大学 | Application of canotoxin A in preparation of medicine for preventing and treating Alzheimer disease |
| CN111494368B (en) * | 2019-04-30 | 2021-02-26 | 黑龙江中医药大学 | Application of canotoxin A in preparation of medicine for preventing and treating Alzheimer disease |
| CN113713028A (en) * | 2021-09-18 | 2021-11-30 | 海南鑫开源医药科技有限公司 | Composition with effect of inhibiting activity of tumor cells and application thereof |
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| CN107007595A (en) | 2017-08-04 |
| CN107007595B (en) | 2019-01-25 |
| CN105481880A (en) | 2016-04-13 |
| CN106943396B (en) | 2018-08-24 |
| CN105481880B (en) | 2017-07-14 |
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