CN105985358B - Liu Yazi total alkaloid extract and its preparation method and application - Google Patents
Liu Yazi total alkaloid extract and its preparation method and application Download PDFInfo
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Abstract
The invention belongs to medicine and field of health care products, and in particular to the application of Liu Yazi total alkaloid extract and its monomeric compound in preparing the drug or health products in terms for the treatment of tumor in digestive tract disease.The present invention extracts and prepares Liu Yazi total alkaloid extract and its mountain wax plum bases monomeric compound from Calycanthaceae wax-cakes bait plant Liu Yazi（1−4）, and be verified by experiments, the Liu Yazi total alkaloid extract can significantly inhibit the proliferation and cancer cell specific induction of apoptosis of gastric cancer SGC 7901, colon cancer SW1116, colon cancer HCT116 cells；The alkaloid monomeric compound has different degrees of inhibiting effect to gastric cancer SGC 7901, colon cancer SW1116, colon cancer HCT116 cells.The Liu Yazi extract and its monomeric compound of the present invention can be used alone or share, or it is combined with suitable excipient, oral or non-oral dosage forms is conventionally made for treatment or assist digestion road tumor disease, is especially formed into the drug or health-care products for the treatment of gastric cancer and colon cancer.
Description
Technical field
The invention belongs to medicine and field of health care products, and in particular to Liu Yazi total alkaloid extract and preparation method thereof
And application, and in particular to Liu Yazi total alkaloid extract and its monomeric compound are preparing treatment tumor in digestive tract disease side
The drug in face or the application in health products.
Technical background
It is the common digestive system carcinoma in China prior art discloses gastric cancer and colon cancer, with regard to morbidity and mortality
Speech, gastric cancer occupies the first place of various malignant tumours in China, and colon cancer is also in the trend risen year by year in China, in prosperity
Country will be listed in front three.For two big kinds of tumor of Digestive, modern medicine is typically based on operative treatment, chemotherapy is
Auxiliary, medical practice is shown, above-mentioned therapy intervention measure side effect is big, and postoperative recurrence transfer probability is very high, and complication is more,
Therefore, lack effective measures and method in terms of prevention and treatment at present.Traditional Chinese medicine is the rarity of the Chinese nation, has sample simultaneous
It controls, actual situation and control, the effect of emergency is taken in concurrently, traditional Chinese medicine has achieved good result in terms for the treatment of malignant tumour in recent years.Cause
How this, excavate tcm characteristic and advantage under instruction of Chinese Medicine theory, and exploitation toxic side effect is small, curative effect is reliable, economic security, makes
It is a project urgently explored with convenient Chinese herbal and crude drugs preparations or new Chinese medicine treatment malignant tumour.
The She nationality, distributed over Fujian, Zhejiang, Jiangxi and Guangdong's medicine is one of China's national characters drug, there is long applicating history in the Yi people.Liu Yazi
（Chimonanthus salicifolius）, it is commonly called as the cool support of leaf of Chimonanthus Nitens, food, mountain wax tea, is that the Lishui of Zhejiang Yi people of China people answer
With widest one of herbal medicine.It is processed into food herbal tea with the leaf of Liu Yazi between the She nationality, distributed over Fujian, Zhejiang, Jiangxi and Guangdong villager after testing and mainly contains folium eucalypti
The ingredients such as element, alkaloid, flavonoids and scyllitol, wherein VB1, VB2, VC rich content, and contain 18 kinds of ammonia needed by human
Base acid, while also containing the essential trace elements of the human bodys such as iron, zinc, calcium, magnesium, selenium, it is a kind of good natural health medicine.1997
Year version Chinese Pharmacopoeia one records the effect of " leaves of Chimonanthus Salicifolius and its preparation Liu Yazi tea " expels pathogenic wind from the body surface, is clearing heat and detoxicating,
It cures cold and influenza for anti-.And the easypro glue of taste that the volatile oil component by being extracted in leaves of Chimonanthus Salicifolius develops
Capsule has the effect of regulating qi-flowing for strengthening spleen, promoting digestion and removing indigestion, is clinically used for treatment cold-damp affecting spleen, the disorders of digestion of liver-stomach disharmony, stomach
The diseases such as portion's illness.In addition, there is clinical research to be used for adjuvant chemotherapy gastrointestinal cancer using Liu Yazi extract（Gastric cancer,
Colorectal cancer）Treatment.However, so far there is not yet application of the Liu Yazi extract on gastric cancer, colon cancer drug, more has no
The report of correlative study about Liu Yazi total alkaloid extract and its alkaloid monomeric compound.
Invention content
The purpose of the present invention is to provide the drugs or health products of new treatment tumor in digestive tract disease, and in particular to willow leaf
Wax plum total alkaloid extract and its preparation method and application, is more particularly to Liu Yazi total alkaloid extract and monomer
Compound and the application in the drug or health products for preparing treatment tumor in digestive tract disease.
The present invention is confirmed through research, alkaloid component is contained in Liu Yazi, and found in the experiment of random screening active ingredients
Total alkaloid extract has inhibitory activity, therefore, the Liu Yazi total alkaloid extract to alimentary canal tumour cell
And its mountain wax plum bases monomeric compound can be further used for preparing the drug or health products for the treatment of tumor in digestive tract disease.
In the present invention, Liu Yazi total alkaloid extract and its mountain wax plum bases monomeric compound are additionally provided（1−4）
Extraction and preparation method.
The active constituent Liu Yazi total alkaloid extract and its mountain wax plum bases monomeric compound of the present invention can be from willow
Leaf wax plum branch and leaf are prepared via method conventional involved by this field.
Specifically, the Liu Yazi total alkaloid extract of the present invention, can be made by following methods：With Liu Yazi branch
Leaf is raw material, and concentrated extract is made using solvent extraction method.In used solvent extraction method, water, methanol, second can be selected
The mixing solvent of the single solvents such as alcohol, acetone or multi-solvents impregnates at room temperature using 50 ~ 95% ethyl alcohol as optimum extraction solvent
Refluxing extraction under extraction or heating condition, extraction time are 2~3 times, and it is water-soluble to be suspended in appropriate 3% tartaric acid after extracting solution concentration
In liquid, extracted 2~3 times with isometric ethyl acetate；Aqueous tartaric acid solution is with Na2CO3PH value is adjusted to 10, then uses chloroform
It is extracted, obtains total alkaloid（Chloroform extract）；Further, through pillar layer separation, purifying, from Liu Yazi chloroform recovery
Following formula monomeric compound salicifoxazines A are obtained in object successively（1）And B（2）, ()-chimonanthine (3) and
(meso) (4)-chimonanthine,
Wherein, the monomeric compound 1 and 2, passes through1H-NMR、13C-NMR, 2D-NMR and MS determine its chemical constitution
It is shown below：
Salicifoxazine A（1）：[α]D -243.9 (c 0.37, MeOH); UV (MeOH) λmax (log ε)
241 (3.87), 298 (3.45) nm; IR (film) νmax: 3279, 2930, 2850, 1604, 1483, 1379
cm-1; 1H-NMR（400MHz, CDCl3）：δ 2.44 (2H, m, overlapped, H-2), 2.63 (1H, ddd,
overlapped, H-3), 1.71 (1H, td, 4.9, 11.8, H-3), 7.16 (1H, dd, 7.5, 1.0, H-
4), 6.74 (1H, td, 7.5, 1.0, H-5), 7.07 (1H, td, 7.5, 1.0, H-6), 6.61 (1H, dd,
7.5, 1.0, H-7), 4.47 (1H, brs, H-8a), 2.27 (3H, s, N1-CH3); δ 2.66 (1H, ddd,
overlapped, H-2’), 2.33 (1H, td, 11.3, 3.5, H-2’), 2.45 (1H, m, H-3’), 2.02
(1H, ddd, 2.2, 3.5, 13.3, H-3’), 7.21 (1H, dd, 7.5, 1.0, H-4’), 6.86 (1H, td,
7.5, 1.0, H-5’), 7.17 (1H, td, 7.5, 1.0, H-6’), 6.71 (1H, dd, 7.5, 1.0, H-
7’), 5.11 (1H, brs, H-8a’), 2.41 (3H, s, N1’-CH3); 13C-NMR (100 MHz, CDCl3): δ
52.9 (C-2), 34.3 (C-3), 125.7 (C-4), 118.6 (C-5), 128.3 (C-6), 109.2 (C-7),
64.1 (C-3a), 132.3 (C-4a), 151.1 (C-7a), 85.2 (C-8a), 37.2 (N1-CH3); δ 53.8
(C-2’), 27.3 (C-3’), 125.1 (C-4’), 118.8 (C-5’), 128.5 (C-6’), 109.5 (C-7’),
50.9 (C-3a’), 129.4 (C-4a’), 151.1 (C-7a’), 93.2 (C-8a’), 46.3 (N1’-CH3); (+)
ESIMS m/z 363 [M+H]+; EIMS m/z （rel. int.） 362 (6.8), 173 (50.0), 172 (50.7),
143 (69.4), 130 (96.7); HRESIMS m/z 363.2176 [M+H]+ (calcd for C22H27N4O,
363.2179, Δ = -0.9 ppm).
Salicifoxazine B（2）：[α]D -2.2 (c 0.32, MeOH); UV (MeOH) λmax (log ε)
241 (3.62), 294 (3.20) nm; IR (film) νmax: 3265, 2925, 2848, 1605, 1483, 1379
cm-1; 1H-NMR（400MHz, CDCl3）：δ 2.67 (1H, m, H-2), 2.43 (1H, m, overlapped, H-2),
2.53 (1H, ddd, 6.5, 8.3, 11.8, H-3), 1.84 (1H, m, H-3), 6.51 (1H, d,
overlapped, H-4), 6.47 (1H, t, 7.5, H-5), 6.97 (1H, t, 7.5, H-6), 6.47 (1H,
d, 7.5, H-7), 4.83 (1H, brs, H-8a), 2.39 (3H, s, N1-CH3); δ 2.83 (1H, ddd,
3.8, 5.3, 10.2, H-2’), 2.46 (1H, m, H-2’), 2.46 (1H, m, overlapped, H-3’),
2.38 (1H, m, overlapped, H-3’), 6.61 (1H, d, overlapped, H-4’), 6.75 (1H, t,
7.5, H-5’), 7.12 (1H, t, 7.5, H-6’), 6.55 (1H, d, 7.5, H-7’), 5.26 (1H, brs,
H-8a’), 2.49 (3H, s, N1’-CH3); 13C-NMR (100 MHz, CDCl3): δ 52.7 (C-2), 35.0 (C-
3), 124.9 (C-4), 118.2 (C-5), 127.9 (C-6), 108.8 (C-7), 64.3 (C-3a), 132.3
(C-4a), 150.9 (C-7a), 83.6 (C-8a), 36.4 (N1-CH3); δ 53.9 (C-2’), 28.4 (C-3’),
123.8 (C-4’), 118.9 (C-5’), 128.4 (C-6’), 109.7 (C-7’), 50.8 (C-3a’), 130.4
(C-4a’), 150.7 (C-7a’), 92.3 (C-8a’), 46.4 (N1’-CH3); (+) ESIMS m/z 363 [M+Na
]+; EIMS m/z 362 (5.0), 173 (81.3), 172 (100.0), 143 (31.5), 130 (80.9); (+)
HRESIMS m/z 385.1995 [M+H]+ (calcd for C22H26N4ONa, 385.1999, Δ = -1.0 ppm).。
The present invention carried out MTT active testings experiment, the results showed that it is described, Liu Yazi total alkaloid extract and its
Mountain wax plum bases monomeric compound significantly inhibits gastric cancer SGC-7901, colon cancer SW1116, HCT116 cell.
Liu Yazi extract and its monomeric compound of the present invention can be used alone or share, or with it is suitable
Excipient combines, and oral or non-oral dosage forms is conventionally made for treating tumor in digestive tract disease, is especially formed into
Treat the drug of gastric cancer and colon cancer.
Liu Yazi extract and its monomeric compound of the present invention can be used alone or share, or with it is suitable
Excipient combines, and oral or non-oral dosage forms is conventionally made and is used for auxiliary treatment tumor in digestive tract disease health products system
Agent is especially formed into the medicine health product preparation of auxiliary treatment gastric cancer and colon cancer.
It is an advantage of the invention that：
1, provide Liu Yazi total alkaloid extract and mountain wax plum bases monomeric compound to tumor in digestive tract, especially
It is the treatment new application of gastric cancer and colon cancer, and has a extensive future；
2,14 unique structure of monomeric compound therein, compound 1 and 2 especially therein is from Calycanthaceae plant
The noval chemical compound with hexa-atomic nitrogen oxa- ring obtained, this class formation is very rare in natural products；
3, Liu Yazi is widely distributed in south China, and ABUNDANT NATUREAL RESOURSES is cheap and easy to get；
4, the extraction of Liu Yazi total alkaloid extract and monomeric compound and preparation process are simple and easy to do, as treatment
The drug of tumor in digestive tract can effectively simplify therapeutic scheme, reduce treatment cost.
Specific implementation mode
The present invention is further elaborated for following embodiments, but these embodiments have any restrictions to the present invention absolutely not.This
Field technology personnel under the enlightenment of this specification to the present invention implement in made by it is any variation will all fall in claims
In the range of.
Embodiment 1：Prepare Liu Yazi total alkaloid extract
2.0 kg Liu Yazi branches and leaves of dry weight are taken, are crushed, the 90% methanol room temperature cold soaking 24 hours, totally 3 times measured with 3 times.It closes
And No. 3 extracting solutions, it is concentrated under reduced pressure, obtains 300 g medicinal extract, 3% aqueous tartaric acid solution that medicinal extract is measured with 2 times is suspended, use and suspension
Isometric ethyl acetate is extracted three times, and Na is then used2CO3Aqueous tartaric acid solution part is adjusted to pH=10, then uses chlorine
Three times, chloroform obtains 2.3 g of medicinal extract, as Liu Yazi total alkaloid extract after extracting part reduced pressure concentration for imitative extraction.
Embodiment 2：Prepare Liu Yazi total alkaloid extract
2.0 kg Liu Yazi branches and leaves of dry weight are taken, is crushed, is flowed back 3 hours, be repeated 3 times, merging carries at room temperature with 80% ethyl alcohol
Liquid is taken, 330 g of medicinal extract is concentrated under reduced pressure to obtain, 3% aqueous tartaric acid solution that medicinal extract is measured with 2 times is suspended, with the second isometric with suspension
Acetoacetic ester extracts three times, then uses Na2CO3Aqueous tartaric acid solution is adjusted to pH=10, three times with the extraction of isometric chloroform, chloroform
2.6 g of Liu Yazi total alkaloid extract medicinal extract is obtained after extracting part reduced pressure concentration.
Embodiment 3：Prepare alkaloid monomeric compound（1−4）
By 2.0 g total alkaloids medicinal extract obtained with equimultiple silica gel（100~200 mesh）Sample is mixed, the silica gel measured with 50 times
（200~300 mesh）Column chromatography is carried out, dichloromethane is used：Methanol is eluted as eluent gradient（Volume ratio 1:0-0:1）.
Collect dichloromethane：Methanol（15:1, volume ratio）Elution fraction, which continued silicagel column, using dichloromethane：Methanol
50:1、30:1、10:1 elution, to 30:1 elution fraction is purified using HPLC is prepared, with methanol：Water：Diethylamine（68：32：
0.05%）Isocratic elution collects 17. 2 min components, obtains 12.2 mg white amorphous powders ()-chimonanthine
(3), 13.0 min components are collected, the white amorphous powder salicifoxazine B of 8.1 mg are obtained（2）；With methanol：Water：
Diethylamine（75：25：0.05%）Isocratic elution collects 10.6 min components, obtains white amorphous powder (meso)-
chimonanthine (4) 4.6 mg；With methanol：Water：Diethylamine（55：45：0.05%）Isocratic elution collects 15.5 min groups
Point, 4.2 mg obtain faint yellow jelly salicifoxazine A（1）.
Embodiment 4：
By 2.0 g total alkaloid medicinal extract loadings to macroreticular resin HP-20, respectively with water, 50% ethyl alcohol, 90% ethanol elution,
By Sephadex LH-20 on 50% ethanol elution part, using dichloromethane：Methanol 2:1 elution, is obtained by TLC combining data detections
To (meso)-chimonanthine (4) of the 4.3 mg and salicifoxazine A of 3.8 mg（1）, remaining group division
And purified afterwards using preparation HPLC, with methanol：Water：Diethylamine（68：32：0.05%）Isocratic elution collects 17. 2 min
Group gets 13.2 mg white amorphous powders ()-chimonanthine (3), collects 13.0 min groups and gets the white of 8.7 mg
Color amorphous powder salicifoxazine B（2）.
Embodiment 5：The inhibiting effect of total alkaloid extract and monomeric compound to alimentary canal tumor cell proliferation
In the present embodiment, the inhibition of alimentary canal tumour cell is imitated in order to probe into total alkaloid extract and monomeric compound
Fruit has selected 3 kinds of pernicious tumor in digestive tract cell lines（Gastric cancer SGC-7901, colon cancer SW1116, colon cancer HCT116）, and it is right
It carries out external activity test, and specific method and result are as follows：
1）Material and method
Cell strain：Gastric cancer SGC-7901, colon cancer SW-1116 purchases are in Chinese Academy of Sciences's Shanghai Institute of Cell Biology, knot
Intestinal cancer HCT-116 is provided by East China Normal University Zhao full professor.HCT-116 cell inoculations in containing 10% heat inactivation newborn bovine serum,
In the RPMI-1640 culture mediums of 100000 U/L penicillin and 100,000 U/L streptomysins, 37oC、5% CO2Under the conditions of cultivate, with 0.25%
Pancreatin had digestive transfer culture；
Main agents：Methyl thiazoly tetrazolium assay（MTT）（Sigma companies of the U.S.）；Dimethyl sulfoxide (DMSO)（DMSO）（The U.S.
Sigma companies）；Trypsase（Resco companies of the U.S.）；1640 culture mediums（Sai Mo flies biochemistry Products Co., Ltd）；5-
Fluorouracil（Sigma companies of the U.S.）；Embryo cow's serum（FBS, sigma companies of the U.S.）；
MTT detects inhibitory activity：Each tumour cell of logarithmic growth phase（Gastric cancer SGC-7901, colon cancer SW1116,
HCT116）96 orifice plates are inoculated in respectively with 5000/hole to be separately added into the Liu Yazi containing various concentration after inoculation for 24 hours and always give birth to
Alkaloids and monomeric compound sample, control group add fresh medium, each concentration and control group（5 FU 5 fluorouracil）It is all provided with 6 again
Hole, 37 oCIt is cultivated in incubator, 5 mg/mL MTT solution, 10 μ L is added after 48h and continue to cultivate in 37 °C of incubators
It after 4h, discards supernatant, is added after 150 μ L DMSO vibrate ten minutes and measures each hole at 570 nm with enzyme-linked immunosorbent assay instrument device
Absorbance, inhibitory rate of cell growth, inhibiting rate is calculated as follows（%）= （1-AExperiment/AControl）×100%；According to each group sample pair
Half-inhibition concentration of the sample to each tumour cell is calculated with LOGIT methods in the growth inhibition ratio of different tumour cells
（IC50）, test data is as follows：
As a result it shows：
Liu Yazi total alkaloid extract and monomeric compound are different to the inhibitory activity of different tumor in digestive tract cells,
Wherein, compound 1 significantly inhibits the growth of colon cancer SW1116 cells, compound 2 and 4 couples of gastric cancer SGC-
There is apparent inhibitory activity, compound 3 to have apparent suppression to the growth of colon cancer HCT116 cells for the growth of 7901 cells
System activity.
Claims (7)
1. in the Liu Yazi of following structural formula alkaloid monomeric compound salicifoxazine A (1) and
Salicifoxazine B (2) contain Liu Yuan oxazine heterocyclic fragments in the structure,
2. prepared by monomeric compound salicifoxazine A (1) described in claim 1 or salicifoxazine B (2)
Treat the application in tumor in digestive tract drug or health products.
3. purposes as described in claim 2, which is characterized in that the tumor in digestive tract is gastric cancer or colon cancer.
4. a kind of pharmaceutical composition for treating tumor in digestive tract, it is characterised in that：Including monomeric compound described in claim 1
1 or 2 with pharmacy in common excipient.
5. a kind of health products of auxiliary treatment tumor in digestive tract, it is characterised in that：Including monomeric compound described in claim 1
1 and 2 with health products in common excipient.
6. the pharmaceutical composition for the treatment of tumor in digestive tract according to claim 4, which is characterized in that the pharmaceutical composition
The preparation of oral administration and the injection of non-oral administration is made in object.
7. the health products of auxiliary treatment tumor in digestive tract according to claim 5, which is characterized in that the health products system
At the preparation of oral administration and the injection of non-oral administration.
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| CN108159093B (en) * | 2018-03-20 | 2022-04-05 | 浙江华润三九众益制药有限公司 | Application of chimonanthus salicifolius extract in enhancing immunity |
| CN110078749B (en) * | 2019-06-04 | 2021-01-01 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | 3a, 3a' -difuran [2,3-b ] indoline compound, preparation method, pharmaceutical composition and application |
| CN111269230B (en) * | 2020-03-12 | 2021-02-26 | 江西中医药大学 | Chimonanthine-2, 3-dione and preparation method and medical application thereof |
| CN114456196B (en) * | 2020-11-10 | 2023-11-10 | 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) | Preparation method of 3a,3a' -dipyrrole [2,3-b ] indoline compound |
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| CN103405482B (en) * | 2013-01-25 | 2016-01-06 | 丽水同舟药食资源科技开发有限公司 | Chimonanthus salicifolius extract is in preparation treatment inflammatory bowel and the application alleviated in the medicine of the injury to alimentary tract that chemotherapeutics causes |
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