CN105985358A - Chimonanthus salicifolius total alkaloid extract, and preparation method and application thereof - Google Patents
Chimonanthus salicifolius total alkaloid extract, and preparation method and application thereof Download PDFInfo
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Abstract
The invention belongs to the field of medicines and health products, and concretely relates to an application of Chimonanthus salicifolius total alkaloid extract and monomer compounds thereof in the preparation of medicines or health products for treating gastrointestinal tumor diseases. The Chimonanthus salicifolius total alkaloid extract and chimonanthine monomer compounds (1-4) are extracted and prepared from a Calycanthaceae Chimonanthus plant Chimonanthus salicifolius, and experiments prove that the Chimonanthus salicifolius total alkaloid extract can substantially inhibit proliferation of stomach cancer SGC-7901, colorectal carcinoma SW1116 and colorectal carcinoma HCT116 cells and induce cancer cell apoptosis, and the alkaloid monomer compounds have different inhibition effects on the stomach cancer SGC-7901, colorectal carcinoma SW1116 and colorectal carcinoma HCT116 cells. The Chimonanthus salicifolius extract and the monomer compounds thereof can be applied individually or together or be combined with a suitable excipient, can be processed through a routine method to prepare an oral or non-oral dosage form used for treatment or assisted treatment of gastrointestinal tumor diseases, and is especially suitable for being used to prepare medicines or health products for treating stomach cancer and colorectal carcinoma.
Description
Technical field
The invention belongs to medicine and field of health care products, it is specifically related to Liu Yazi total alkaloid extract and its preparation method and application, be specifically related to Liu Yazi total alkaloid extract and monomeric compound thereof the medicine in terms of preparation treatment tumor in digestive tract disease or the application in health products.
Technical background
Prior art discloses cancer of the stomach and colon cancer is the common digestive system carcinoma of China, for M & M, cancer of the stomach occupies the first place of various malignant tumour in China, and colon cancer is also in the trend that rises year by year in China, in developed country's front three to be listed in.The two big kinds of tumor for Digestive, modern medicine be typically with based on operative treatment, chemotherapy be auxiliary, medical practice shows, above-mentioned Results measure side effect is big, and postoperative recurrence transfer probability is very high, complication is more, therefore, lacks effective measures and method at present in terms of prevention and treatment.Traditional Chinese medicine is the rarity of the Chinese nation, have treat both principal and secondary aspect of disease, actual situation and control, effect that emergency is taken in concurrently, in recent years traditional Chinese medicine in terms for the treatment of malignant tumour achieved with good result.Therefore, how to excavate tcm characteristic and advantage under instruction of Chinese Medicine theory, exploitation toxic and side effect is little, curative effect reliable, economic security, Chinese herbal and crude drugs preparations easy to use or new Chinese medicine treatment malignant tumour are problems urgently explored.
One of She Yaoshi China national characters medicine, has long applicating history in the She.Liu Yazi (Chimonanthus salicifolius), is commonly called as leaf of Chimonanthus Nitens, eats cool support, mountain wax tea, is one of most widely used herbal medicine of the Lishui of Zhejiang She of China people.It is processed in food cold tea by the leaf of Liu Yazi between the She nationality, distributed over Fujian, Zhejiang, Jiangxi and Guangdong villager after testing and mainly contain the compositions such as Cineole, alkaloid, flavonoids and scyllitol, wherein VB1, VB2, VC rich content, and the amino acid containing 18 kinds of needed by human, trace element possibly together with needed by human such as iron, zinc, calcium, magnesium, selenium simultaneously, is a kind of good natural health medicine.Version Chinese Pharmacopoeia one in 1997 record " leaves of Chimonanthus Salicifolius and preparation Liu Yazi tea thereof " have expel pathogenic wind from the body surface, clearing heat and detoxicating effect, cure cold and influenza for anti-.And by the taste relieving capsule that develops of volatile oil component extracting in leaves of Chimonanthus Salicifolius, there is effect of regulating qi-flowing for strengthening spleen, promoting digestion and removing indigestion, it is clinically used for the diseases such as treatment cold-damp affecting spleen, the disorders of digestion of liver-stomach disharmony, gastric lesions.Additionally, there is clinical research to use Liu Yazi extract for the treatment of NACT gastrointestinal cancer (cancer of the stomach, colorectal cancer).But, there is not yet Liu Yazi extract so far for the application on cancer of the stomach, colon cancer drug, more have no the report with regard to Liu Yazi total alkaloid extract and the correlative study of alkaloid monomeric compound thereof.
Content of the invention
It is an object of the invention to provide medicine or the health products of new treatment tumor in digestive tract disease, it is specifically related to Liu Yazi total alkaloid extract and its preparation method and application, be more particularly to Liu Yazi total alkaloid extract and monomeric compound thereof and the application in the medicine or health products of preparation treatment tumor in digestive tract disease.
The present invention confirms after deliberation, Liu Yazi contains alkaloid component, and discovery total alkaloid extract has inhibitory activity to alimentary canal tumour cell in the experiment of random screening active ingredients, therefore, described Liu Yazi total alkaloid extract and chimonanthine class monomeric compound thereof can be further used for medicine or the health products of preparation treatment tumor in digestive tract disease.
In the present invention,Additionally provide Liu Yazi total alkaloid extract and chimonanthine class monomeric compound thereof (1−4) extraction and preparation method.
The active component Liu Yazi total alkaloid extract of the present invention and chimonanthine class monomeric compound thereof can be prepared from Liu Yazi branch and leaf via method conventional involved by this area.
Concrete, the Liu Yazi total alkaloid extract of the present invention, can be prepared by following method: with Liu Yazi branches and leaves as raw material, use solvent extraction method to make concentrated extract.In the solvent extraction method being used, the mixing solvent of the single solvents such as water, methyl alcohol, ethanol, acetone or multi-solvents can be selected, it is optimum extraction solvent with 50 ~ 95% ethanol, at room temperature refluxing extraction under Soakage extraction or heating condition, extraction time is 2～3 times, extract is suspended in appropriate 3% aqueous tartaric acid solution after concentrating, and extracts 2～3 times with isopyknic ethyl acetate；Aqueous tartaric acid solution is with Na2CO3Regulation pH value, to 10, is then extracted by chloroform, it is thus achieved that TA (chloroform extract)；Further, through pillar layer separation, purifying, from Liu Yazi chloroform extract, following formula monomeric compound salicifoxazines is obtained successivelyA(1) andB(2), ()-chimonanthine
(3) and (meso)-chimonanthine (4),
Wherein, described monomeric compound1With2, pass through1H-NMR、13C-NMR, 2D-NMR and MS, determine that its chemical constitution 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 has carried out the experiment of MTT active testing, and result shows described, and Liu Yazi total alkaloid extract and chimonanthine class monomeric compound thereof have obvious inhibitory action to cancer of the stomach SGC-7901, colon cancer SW1116, HCT116 cell.
Liu Yazi extract of the present invention and monomeric compound thereof can be used alone or share, or be combined with suitable excipient, conventionally make oral or non-oral dosage forms for treating tumor in digestive tract disease, especially make the medicine for the treatment of cancer of the stomach and colon cancer.
Liu Yazi extract of the present invention and monomeric compound thereof can be used alone or share, or be combined with suitable excipient, conventionally make oral or non-oral dosage forms and treat tumor in digestive tract disease health-care preparation for assisting, especially make the medicine health product preparation of auxiliary treatment cancer of the stomach and colon cancer.
The invention have the advantage that
1, provide Liu Yazi total alkaloid extract and the treatment new application to tumor in digestive tract, especially cancer of the stomach and colon cancer for the chimonanthine class monomeric compound, and have a extensive future；
2, monomeric compound therein1−4Structure is unique, compound especially therein1With2For the noval chemical compound with hexa-atomic nitrogen oxa-ring obtaining from Calycanthaceae plant, in natural products, this class formation is very rare；
3, Liu Yazi is widely distributed at south China, and ABUNDANT NATUREAL RESOURSES is cheap and easy to get；
4, extraction and the preparation technology of Liu Yazi total alkaloid extract and monomeric compound are simple and easy to do, as the medicine for the treatment of tumor in digestive tract, can effectively simplify therapeutic scheme, reduce treatment cost.
Detailed description of the invention
The present invention is further elaborated for following embodiment, but these embodiments have absolutely not any restriction to the present invention.Any variation that those skilled in the art are made in implementing the present invention under the enlightenment of this specification all will fall within the scope of the appended claims.
Embodiment1: prepare Liu Yazi total alkaloid extract
Take dry weight 2.0 kg Liu Yazi branches and leaves, pulverize, with the 90% methyl alcohol room temperature cold soaking 24 hours of 3 times amount, totally 3 times.Merging No. 3 extracts, reduced pressure concentration, obtaining 300 g medicinal extract, medicinal extract is suspended by 3% aqueous tartaric acid solution of 2 times amount, carries out extracting three times with ethyl acetate isopyknic with suspension, then uses Na2CO3Aqueous tartaric acid solution part being adjusted to pH=10, then extracting three times with chloroform, chloroform extraction part reduced pressure obtains medicinal extract 2.3 g after concentrating, and is Liu Yazi total alkaloid extract.
Embodiment2: prepare Liu Yazi total alkaloid extract
Take dry weight 2.0 kg Liu Yazi branches and leaves, pulverize, with backflow 3 hours under 80% ethanol room temperature, being repeated 3 times, merging extract, reduced pressure concentration obtains medicinal extract 330 g, medicinal extract is suspended by 3% aqueous tartaric acid solution of 2 times amount, extracts three times with isopyknic ethyl acetate with suspension, then uses Na2CO3Aqueous tartaric acid solution being adjusted to pH=10, extracting three times with equal-volume chloroform, chloroform extraction part reduced pressure obtains Liu Yazi total alkaloid extract medicinal extract 2.6 g after concentrating.
Embodiment3: preparation alkaloid monomeric compound (1−4)
2.0 prepared g TA medicinal extract are mixed sample with equimultiple silica gel (100～200 mesh), carries out column chromatography with the silica gel (200～300 mesh) of 50 times amount, with dichloromethane: methyl alcohol is as eluent gradient wash-out wash-out (volume ratio 1:0-0:1).Collection dichloromethane: methyl alcohol (15:1, volume ratio) elution fraction, this component continued silicagel column, use dichloromethane: methyl alcohol 50:1,30:1,10:1 elute, use preparation HPLC to be purified to 30:1 elution fraction, with methyl alcohol: water: diethylamine (68:32:0.05%) isocratic elution, collect 17. 2 min components, obtain 12.2 mg white amorphous powder ()-chimonanthine
(3), collect 13.0 min components, obtain the white amorphous powder salicifoxazine of 8.1 mgB(2)；With methyl alcohol: water: diethylamine (75:25:0.05%) isocratic elution, collect 10.6 min components, obtain white amorphous powder (meso)-chimonanthine (4) 4.6 mg；With methyl alcohol: water: diethylamine (55:45:0.05%) isocratic elution, collecting 15.5 min components, 4.2 mg obtain faint yellow jelly salicifoxazineA(1).
Embodiment4:
By 2.0 g TA medicinal extract loadings to macroreticular resin HP-20, respectively with water, 50% ethanol, 90% ethanol elution, by Sephadex LH-20 in 50% ethanol elution part, use dichloromethane: methyl alcohol 2:1 elute, by TLC combining data detection obtain 4.3 mg (meso)-chimonanthine (4) and the salicifoxazine of 3.8 mgA(1), remaining component uses preparation HPLC to be purified, with methyl alcohol after merging: water: diethylamine (68:32:0.05%) isocratic elution, collects 17. 2 min components and obtains 13.2 mg white amorphous powder ()-chimonanthine
(3), collect 13.0 min components and obtain the white amorphous powder salicifoxazine of 8.7 mgB(2).
Embodiment5: total alkaloid extract and the inhibitory action to alimentary canal tumor cell proliferation for the monomeric compound
In the present embodiment, in order to probe into total alkaloid extract and the monomeric compound inhibition to alimentary canal tumour cell, have selected 3 kinds of pernicious tumor in digestive tract clones (cancer of the stomach SGC-7901, colon cancer SW1116, colon cancer HCT116), and carry out external activity test to it, concrete method is as follows with result:
1) material and method
Cell line: cancer of the stomach SGC-7901, colon cancer SW-1116 are bought in Chinese Academy of Sciences's Shanghai Institute of Cell Biology, and colon cancer HCT-116 is provided by East China Normal University Zhao full professor.HCT-116 cell is inoculated in the RPMI-1640 culture medium containing 10% heat inactivation NBCS, 100,000 U/L penicillin and 100,000 U/L streptomysins, and 37oC、5% CO2Under the conditions of cultivate, pass on the trypsinization of 0.25%；
Main agents: Methyl thiazoly tetrazolium assay (MTT) (sigma company of the U.S.)；Dimethyl sulfoxide (DMSO) (DMSO) (sigma company of the U.S.)；Trypsase (resco company of the U.S.)；1640 culture mediums (Sai Mo flies biochemistry Products Co., Ltd)；5 FU 5 fluorouracil (sigma company of the U.S.)；Embryo cow's serum (FBS, sigma company of the U.S.)；
MTT detects inhibitory activity: each tumour cell (cancer of the stomach SGC-7901, colon cancer SW1116, HCT116) in growth period of taking the logarithm is inoculated in 96 orifice plates respectively with 5000/hole, after inoculation 24h, it is separately added into the Liu Yazi TA containing variable concentrations and monomeric compound sample, control group adds fresh medium, each concentration and control group (5 FU 5 fluorouracil) are all provided with 6 multiple holes, 37 oCIncubator is cultivated, after 48h, adds 5 mg/mL
After MTT solution 10 μ L continues to cultivate 4h in 37 ° of C incubators, supernatant discarded, measure absorbance at 570 nm for each hole with enzyme-linked immunosorbent assay instrument device after adding 150 μ L DMSO to vibrate ten minutes, be calculated as follows inhibitory rate of cell growth, inhibiting rate (%)=(1-AExperiment/AComparison) × 100%；According to the growth inhibition ratio to different tumour cells for each group of sample, calculate the half-inhibition concentration (IC that there emerged a sample to each tumour cell by LOGIT method50), test data are as follows:
Result shows:
Liu Yazi total alkaloid extract and monomeric compound are different to the inhibitory activity of different tumor in digestive tract cells, wherein, and compound1Growth to colon cancer SW1116 cell has obvious inhibitory action, compound2With4Growth to SGC-7901 cell has obvious inhibitory activity, compound3Growth to colon cancer HCT116 cell has obvious inhibitory activity.
Claims (8)
1. Liu Yazi total alkaloid extract and monomeric compound thereof, it is characterised in that prepared by following method: with Liu Yazi branches and leaves as raw material, uses solvent extraction method to make concentrated extract；Wherein, with the mixing solvent of water, methyl alcohol, ethanol or acetone single solvent or multi-solvents as Extraction solvent, at room temperature refluxing extraction 2～3 times under Soakage extraction or heating condition, extract is suspended in appropriate 3% aqueous tartaric acid solution after concentrating, and extracts 2～3 times with isopyknic ethyl acetate；Aqueous tartaric acid solution is with Na2CO3Regulation pH value, to 10, then carries out extracting to obtain chloroform extract with chloroform, it is thus achieved that TA；Again through pillar layer separation, purifying, from described chloroform extract, obtain following formula monomeric compound salicifoxazines successivelyA(1) andB(2), ()-chimonanthine (3) and (meso)-chimonanthine (4),
。
2. the Liu Yazi total alkaloid extract as described in claim 1 and monomeric compound thereof, it is characterised in that in described preparation method: with 50 ~ 95% ethanol as Extraction solvent.
3. the Liu Yazi total alkaloid extract described in claim 1 and application in preparation treatment tumor in digestive tract medicine or health products for the monomeric compound thereof.
4. the purposes as described in claim 3, it is characterised in that described tumor in digestive tract is cancer of the stomach or colon cancer.
5. the pharmaceutical composition treating tumor in digestive tract, it is characterised in that: include excipient conventional in the Liu Yazi total alkaloid extract described in claim 1 or monomer compound and pharmacy.
6. the health products assisting treatment tumor in digestive tract, it is characterised in that: include excipient conventional in the Liu Yazi total alkaloid extract described in claim 1 or monomer compound and health products.
7. the pharmaceutical composition for the treatment of tumor in digestive tract according to claim 5, it is characterised in that described pharmaceutical composition makes the preparation of oral administration and the injection of non-oral administration.
8. the health products of auxiliary treatment tumor in digestive tract according to claim 6, it is characterised in that described health products make the preparation of oral administration and the injection of non-oral administration.
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| CN108159093A (en) * | 2018-03-20 | 2018-06-15 | 浙江华润三九众益制药有限公司 | The immune application of Liu Yazi extract enhancing |
| CN110078749A (en) * | 2019-06-04 | 2019-08-02 | 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`- Coumarin [2,3-b] indoline-like compound, preparation method, pharmaceutical composition and application |
| CN111269230A (en) * | 2020-03-12 | 2020-06-12 | 江西中医药大学 | Chimonanthine-2, 3-dione and preparation method and medical application thereof |
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| CN108159093A (en) * | 2018-03-20 | 2018-06-15 | 浙江华润三九众益制药有限公司 | The immune application of Liu Yazi extract enhancing |
| 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 |
| CN110078749A (en) * | 2019-06-04 | 2019-08-02 | 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`- Coumarin [2,3-b] indoline-like compound, preparation method, pharmaceutical composition and application |
| 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 |
| CN111269230A (en) * | 2020-03-12 | 2020-06-12 | 江西中医药大学 | Chimonanthine-2, 3-dione and preparation method and medical application thereof |
| CN114456196A (en) * | 2020-11-10 | 2022-05-10 | 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 |
| 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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