CN102030800A - Abies holophylla triterpenoid compound, extraction separation thereof and application thereof - Google Patents
Abies holophylla triterpenoid compound, extraction separation thereof and application thereof Download PDFInfo
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Abstract
The invention provides an abies holophylla triterpenoid compound, which comprises the following compounds 1, 2, 3, 4 and 5. The compounds are subjected to an experiment of cytotoxic activity, and a result shows that the five compounds have good inhibitory activity and excellent anti-tumor effect on human lung cancer cells, human intestinal cancer cells, human small cell lung cancer cells and human breast cancer cells. The five compounds are proved by a curative effect experiment on sarcoma (entities) of mice S180 to have the obvious tumor-inhibitory effect. The abies holophylla triterpenoid compound can be used for preparing anti-cancer medicaments. The medicaments of the invention consist of the abies holophylla triterpenoid compound serving as active ingredients and a conventional medicinal carrier, and can be prepared into preparations according to the conventional method. The medicaments of the invention are Chinese medicinal preparations, have small toxic and side effect and high curative effect, provide new anti-cancer medicaments clinically, have large practical application value and can create good social benefit.
Description
Technical field
The present invention relates to pharmaceutical chemistry, be specifically related to Manchurian fir triterpene compound and extraction separation thereof and application.Relate in particular to the application of Manchurian fir triterpene compound in the preparation cancer therapy drug.
Background technology
Tumour is to cause one of human main causes of death.Ministry of Health of China is announced urban and rural residents' major causes of death in 2006.Statistics shows that malignant tumour has become the primary cause of the death.As seen the prevention of tumour and treatment are very urgent.Pharmacological agent is one of main treatment means of tumour.At present, though developed tens of kinds of antitumor drugs, effectively prolonged patient's life or improved patient's life quality.But the drug research of tumour and exploitation also face huge challenge, mostly are cell toxicity medicament as antitumor drug, and its side effect is obvious, has limited the performance of these curative effect of medication.Famous tumor aetiology man, member of Chinese Academy of Engineering's journey book an ancient unit of weight are thought: current medical science still is in the junior stage for the control of tumour.Chinese medicine has the basis of human toxicity experiment in several thousand, and the lead compound of seeking the anti-tumor activity of high-efficiency low-toxicity from natural product is the focus of new drug research always.
Abies (Abies) is the important genus of Pinaceae (Pinaceae), has 50 kinds approximately, is distributed in Asia, Europe, North America, the northern alpine belt of Sino-U.S. and Africa.In state-owned 19 kind of 3 mutation.Be distributed in the alpine belt of northeast, North China, northwest, southwest and Zhejiang, each provinces and regions, Taiwan.Wherein some plant is used as medicine among the people in some areas, is used to catch a cold, the treatment of stomachache, maldigestion and blood vessel, lung and venereal disease etc.Modern study shows, from this platymiscium, separate some compounds and the derivative thereof obtain and have multiple biological activity, comprising: the disease that insect protects young, antitumor, antibiotic, antiulcer agent, anti-inflammatory, hypertension, cough-relieving and treats the central nervous system aspect.Because this platymiscium has physiologically active widely mostly, and is from 1938 so far, many to the research of this platymiscium in the world.
Manchurian fir Abies holophylla is the Abies plant.Mainly originate in mountain area, basin, Mudanjiang, Northeast China, Changbaishan area and Liaohe River Eastern Mountain Area.In view of Abies plant pharmacologically active preferably, the inventor has carried out the chemical constitution study of system to Manchurian fir, finds that wherein the Manchurian fir triterpene compound has good antineoplastic activity, intends developing anti-tumor medicaments.
Summary of the invention
Technical problem to be solved by this invention is to study Manchurian fir triterpene compound anti-tumor activity, the extraction and separation method of design Manchurian fir triterpene compound and the application in pharmacy thereof.
The invention provides a kind of Manchurian fir triterpene compound, comprise following compounds 1,2,3,4,5:
Compound 1:25,26, three carbon-3 Alpha-hydroxy ring A Er front yard alkane-24-carboxylic acid falls in 27-; Compound 2:25,26, three carbon-3 α-methoxy basic ring A Er front yard alkane-24 carboxylic acid falls in 27-; Compound 3:24,25,26, three carbon-3-carbonyl-9 β hydrogen-lanostane-7-alkene-23-carboxylic acid falls in 27-; Compound 4:3,4-open loop-9 β hydrogen-lanostane-4 (28), 7,22,25-tetraene-23,26-lactone-3-carboxylic acid; Compound 5: lanostane-7,9 (11), 24-triolefin-26-carboxylic acid
Compound 1:25,26,27-Trinor-3 α-hydroxycycloartan-24-oic acid
25,26, three carbon-3 Alpha-hydroxy ring A Er front yard alkane-24-carboxylic acid falls in 27-
Amorphous powder, optical value :+12.1 (c 0.08, ethanol), ultraviolet maximum absorption wavelength: 226nm; Infrared spectra maximum absorption wave number: 3445,2928,2868,1715,1457,1383,1068,971cm
-1, ESI-MS:415[M-H]
-, high resolution mass spectrum: 467.3170[M+Na]
+(calcd for C
27H
44O
3Na, 467.3161).
Compound 2:25,26,27-Trinor-3 α-methoxycycloartan-24-oic acid
25,26, three carbon-3 α-methoxy basic ring A Er front yard alkane-24 carboxylic acid falls in 27-
Amorphous powder, optical value :+9.0 (c 0.16, chloroform), ultraviolet maximum absorption wavelength: 223nm; Infrared spectra maximum absorption wave number: 3445,2955,2924,1700,1456,1382,1098cm
-1, ESI-MS:453[M+Na]
+, high resolution mass spectrum: 453.3329[M+Na]
+(calcd for C
28H
46O
3Na, 453.3339).
Compound 3:24,25,26,27-Tetranor-3-oxo-9 β H-lanosta-7-en-23-oic acid
24,25,26, three carbon-3-carbonyl-9 β hydrogen-lanostane-7-alkene-23-carboxylic acid falls in 27-
Amorphous powder, optical value :+43.5 (c 0.23, ethanol), ultraviolet maximum absorption wavelength: 229nm; Infrared spectra maximum absorption wave number: 3439,3031,2961,1730,1458,1320,1050,968,668cm
-1, ESI-MS:399[M-H]
-, high resolution mass spectrum: 423.2888[M+Na]
+(calcd for C
30H
43O
4Na, 423.2870).
Compound 4:3,4-seco-9 β H-Lanosta-4 (28), 7,22,25-tetraen-23,26-olid-3-oicacid
3,4-open loop-9 β hydrogen-lanostane-4 (28), 7,22,25-tetraene-23,26-lactone-3-carboxylic acid
Amorphous powder, optical value :-83.4 (c 0.79, chloroform), ultraviolet maximum absorption wavelength: 279nm; Infrared spectra maximum absorption wave number: 3446,2969,2949,1738,1436,1366,1092,962,758cm
-1, ESI-MS:489[M+Na]
+, high resolution mass spectrum: 489.2994[M+Na]
+(calcd for C
30H
42O
4Na, 489.2975).
Compound 5:Lanosta-7,9 (11) 24-trien-26-oic acid
Lanostane-7,9 (11), 24-triolefin-26-carboxylic acid
Amorphous powder, optical value :-83.4 (c 0.79, chloroform), ultraviolet maximum absorption wavelength: 279nm; Infrared spectra maximum absorption wave number: 3446,2969,2949,1738,1436,1366,1092,962,758cm
-1, ESI-MS:489[M+Na]
+, high resolution mass spectrum: 489.2994[M+Na]
+(calcd for C
30H
42O
4Na, 489.2975).
Table 1.
1H and
13CNMR Spectroscopic Data of compound 1-4in CDCl
3
aAnalysis frequency 100MHz
bAnalysis frequency 400MHz.
cAnalysis frequency 150MHz.
dAnalysis frequency 600MHz.
Compound 5 is known compounds, and its carbon spectrum, hydrogen spectrum data all are disclosed information, and document can be consulted and obtain.
Another object of the present invention has provided the extraction and separation method of above-mentioned Manchurian fir triterpene compound.
Comprise the following steps:
The raw material Manchurian fir that the inventive method is used is picked up from the northeast Changbaishan area, gets its dry pine branch.
(1) extracts: the dry branches and leaves of Manchurian fir are pulverized, with 8-20 times of volume W/V of 75-95% ethanol refluxing extraction 1-3 time, each 2-3 hour, united extraction liquid, the extracting solution concentrating under reduced pressure becomes fluid extract, and fluid extract is equivalent to 1ml and contains Manchurian fir 0.9-1.1g, fluid extract adds water 1-3 doubly measure W/V dilution after, doubly measure V/V extraction 3-5 time with chloroform 0.5-2, obtain chloroform extraction partly;
(2) separate:, be 100 with volume ratio: 0-1 above-mentioned chloroform extraction part applying silicon plastic column chromatography: 1 petrol ether/ethyl acetate system gradient elution, thin-layer chromatography detects, and collects the flow point that contains compound 2,1,3,5,4 respectively by eluotropic series; The compound of each flow point is respectively through sephadex chromatography, is 1: 1 chloroform/methanol wash-out with volume ratio, and again through the C18 reversed phase column chromatography, with volume ratio 6: 4-10: 0 methanol is carried out wash-out, and thin-layer chromatography detects, and finally obtains 5 compounds.
Another purpose of the present invention has provided the application of above-mentioned Manchurian fir triterpene compound in the preparation cancer therapy drug.
The present invention has carried out the cytotoxic activity experiment to above-claimed cpd, comprise A549 (human lung carcinoma cell), Colo 205 (people's colon-cancer cell), NCI-H446 (human small cell lung carcinoma cell) and MDA-MB-435 (human breast cancer cell), the in-vitro multiplication restraining effect, the result shows, 5 compounds are to human lung carcinoma cell, people's colon-cancer cell, human small cell lung carcinoma cell, human breast cancer cell all has better inhibited activity, and favorable anti-tumor effect is arranged.Carried out the efficacy experiment of compound to mouse S180 sarcoma (solid-type) again, 5 compounds all have significant tumor-inhibiting action as a result.Can be used for preparing cancer therapy drug.
Medicine of the present invention is made up of as activeconstituents and conventional pharmaceutical carrier the Manchurian fir triterpene compound, can make pharmaceutical preparation according to a conventional method.
Medicine of the present invention is a Chinese medicine preparation, and the poison effect of paying is little, and good effect provides new cancer therapy drug for clinical, and bigger actual application value and good social benefit are arranged.
Embodiment
Embodiment 1
The raw material Manchurian fir of the following example is picked up from the northeast Changbaishan area, gets its dry branches and leaves.
(1) extract: dry branches and leaves 10Kg pulverizes with Manchurian fir, with 75% ethanol 80L refluxing extraction 1 time, each 2 hours, united extraction liquid, the extracting solution concentrating under reduced pressure becomes fluid extract, and fluid extract is equivalent to 1ml and contains Manchurian fir 0.9g, after fluid extract adds water 12L dilution, with chloroform 6L extraction 3 times, obtain chloroform extraction partly;
(2) separate: above-mentioned chloroform extraction is partly used silica gel column chromatography, with volume ratio is 100: 0-1: 1 petrol ether/ethyl acetate system gradient elution, thin-layer chromatography detects, and collects the flow point that contains above compound respectively, and elution order is a compound 2,1,3,5,4.5 compounds are respectively through sephadex chromatography, it with volume ratio 1: 1 chloroform/methanol wash-out, after the C18 reversed phase column chromatography, with volume ratio 6: 4-10: 0 methanol is carried out wash-out, and thin-layer chromatography detects, obtain 5 compounds at last respectively, compound 1 is 50mg, and compound 2 is 83mg, and compound 3 is 71mg, compound 4 is 38mg, and compound 5 is 126mg.
Compound 1 is an amorphous powder, optical value :+12.1 (c 0.08, ethanol), ultraviolet maximum absorption wavelength: 226nm; Infrared spectra maximum absorption wave number: 3445,2928,2868,1715,1457,1383,1068,971cm
-1, ESI-MS:415[M-H]
-, high resolution mass spectrum: 467.3170[M+Na]
+(calcd for C
27H
44O
3Na, 467.3161).
Compound 2 amorphous powders, optical value :+9.0 (c 0.16, chloroform), ultraviolet maximum absorption wavelength: 223nm; Infrared spectra maximum absorption wave number: 3445,2955,2924,1700,1456,1382,1098cm
-1, ESI-MS:453[M+Na]
+, high resolution mass spectrum: 453.3329[M+Na]
+(cal cd for C
28H
46O
3Na, 453.3339).
Compound 3 amorphous powders, optical value :+43.5 (c 0.23, ethanol), ultraviolet maximum absorption wavelength: 229nm; Infrared spectra maximum absorption wave number: 3439,3031,2961,1730,1458,1320,1050,968,668cm
-1, ESI-MS:399[M-H]
-, high resolution mass spectrum: 423.2888[M+Na]
+(calcd for C
30H
43O
4Na, 423.2870).
Compound 4 amorphous powders, optical value :-83.4 (c 0.79, chloroform), ultraviolet maximum absorption wavelength: 279nm; Infrared spectra maximum absorption wave number: 3446,2969,2949,1738,1436,1366,1092,962,758cm
-1, ESI-MS:489[M+Na]
+, high resolution mass spectrum: 489.2994[M+Na]
+ (Calcd for C
30H
42O
4Na, 489.2975).
Compound 5 amorphous powders, optical value :-83.4 (c 0.79, chloroform), ultraviolet maximum absorption wavelength: 279nm; Infrared spectra maximum absorption wave number: 3446,2969,2949,1738,1436,1366,1092,962,758cm
-1, ESI-MS:489[M+Na]
+, high resolution mass spectrum: 489.2994[M+Na]
+(calcd for C
30H
42O
4Na, 489.2975).
Table 1.
1H and
13CNMR Spectroscopic Data of compound 1-4 in CDCl
3
aAnalysis frequency 100MHz
bAnalysis frequency 400MHz.
cAnalysis frequency 150MHz.
dAnalysis frequency 600MHz.
Embodiment 2
(1) extract: dry branches and leaves 5Kg pulverizes with Manchurian fir, with 80% ethanol 100L refluxing extraction 3 times, each 3 hours, united extraction liquid, the extracting solution concentrating under reduced pressure becomes fluid extract, and fluid extract is equivalent to 1ml and contains Manchurian fir 1.0g, after fluid extract adds water 10L dilution, with chloroform 20L extraction 4 times, obtain chloroform extraction partly;
(3) separate: above-mentioned chloroform extraction part applying silicon plastic column chromatography, with volume ratio is 100: 0-1: 1 petrol ether/ethyl acetate system gradient elution, thin-layer chromatography detects, collect the flow point that contains above compound respectively, elution order is a compound 2,1,3,5,4, are 5 compounds respectively? through sephadex chromatography, be 1: 1 chloroform/methanol wash-out with volume ratio, again through the C18 reversed phase column chromatography, with volume ratio 6: 4-10: 0 methanol is carried out wash-out, thin-layer chromatography detects, and obtains 5 compounds at last respectively, and compound 1 is 31mg, compound 2 is 40mg, compound 3 is 32mg, and compound 4 is 20mg, and compound 5 is 73mg.
Embodiment 3
(1) extract: dry branches and leaves 20Kg pulverizes with Manchurian fir, with 95% ethanol 200L refluxing extraction 3 times, each 3 hours, united extraction liquid, the extracting solution concentrating under reduced pressure becomes fluid extract, and fluid extract is equivalent to 1ml and contains Manchurian fir 1.1g, after fluid extract adds water 54L dilution, with chloroform 54L extraction 5 times, obtain chloroform extraction partly;
(4) separate: above-mentioned chloroform extraction is partly used silica gel column chromatography, with volume ratio is 100: 0-1: 1 petrol ether/ethyl acetate system gradient elution, thin-layer chromatography detects, and collects the flow point that contains above compound respectively, and elution order is a compound 2,1,3,5,4.5 compounds are respectively through sephadex chromatography, are 1: 1 chloroform/methanol wash-out with volume ratio, and after the C18 reversed phase column chromatography, with volume ratio 6: 4-10: 0 methanol is carried out wash-out, and thin-layer chromatography detects, and obtains 5 compounds at last respectively.Compound 1 is 115mg, and compound 2 is 157mg, and compound 3 is 151mg, and compound 4 is 84mg, and compound 5 is 267mg.
Embodiment 4
(1) extract: dry branches and leaves 10Kg pulverizes with Manchurian fir, with 85% ethanol 150L refluxing extraction 3 times, each 2 hours, united extraction liquid, the extracting solution concentrating under reduced pressure becomes fluid extract, and fluid extract is equivalent to 1ml and contains Manchurian fir 1.05g, after fluid extract adds water 10L dilution, with chloroform 8L extraction 4 times, obtain chloroform extraction partly;
(5) separate: above-mentioned chloroform extraction part applying silicon plastic column chromatography, with volume ratio is 100: 0-1: 1 petrol ether/ethyl acetate system gradient elution, thin-layer chromatography detects, and collects the flow point that contains above compound respectively, and elution order is a compound 2,1,3,5,4.5 compounds are respectively through sephadex chromatography, are 1: 1 chloroform/methanol wash-out with volume ratio, and again through the C18 reversed phase column chromatography, with volume ratio 6: 4-10: 0 methanol is carried out wash-out, and thin-layer chromatography detects, and obtains 5 compounds at last respectively.Compound 1 is 54mg, and compound 2 is 79mg, and compound 3 is 80mg, and compound 4 is 36mg, and compound 5 is 119mg..
Embodiment 5
The cytotoxic activity experiment of compound
1, experiment material
1.1, given the test agent
5 compounds (embodiment 1 makes) use respectively DMSO (methyl-sulphoxide) (Merck) dissolve after, add PBS (phosphate buffered saline buffer) (-) and be made into the solution of 1000 μ g/ml or suspension uniformly, then with PBS (-) dilution that contains DMSO.
1.2, cell strain
A549 (human lung carcinoma cell)
Colo 205 (people's colon-cancer cell)
NCI-H446 (human small cell lung carcinoma cell)
MDA-MB-435 (human breast cancer cell)
1.3, nutrient solution
RPMI1640+15%NBS+ is two anti-
Other materials
Full-automatic microplate reader: model: WellscanMK-2, production firm: Labsystems import 96 well culture plates etc.
2, test method
MTT (tetramethyl-azo azoles salt trace enzyme reaction colorimetry) method: it is 4～6 * 10 that the every hole of 96 orifice plates adds concentration
4The cell suspension 100 μ l of individual/ml put 37 ℃, 5%CO
2In the incubator.Behind the 24h, add sample liquid, two multiple holes are established in 10 μ l/ holes, and 37 ℃, 5%CO
2Effect 72h.Every hole adds the MTT solution 20 μ l of 5mg/ml, adds lysate behind the effect 4h, and put in the incubator in 100 μ l/ holes, and 570nm OD value (absorbancy) is surveyed with the full-automatic microplate reader of MK-2 in the dissolving back.
3, test-results
The results are shown in Table 3, the result shows, 5 compounds are to human lung carcinoma cell, people's colon-cancer cell, and human small cell lung carcinoma cell, human breast cancer cell all have better inhibited activity, and favorable anti-tumor effect is arranged, and have the excellent development prospect.
Table 35 compound is to the in-vitro multiplication restraining effect of human body tumour cell
Embodiment 6 compounds are to the efficacy experiment of mouse S180 sarcoma (solid-type)
1, experiment material
1.1 given the test agent
5 compounds (embodiment 1 makes) are respectively with using the 0.5%CMC wiring solution-forming behind a small amount of tween-80 hydrotropy.
1.2 animal
Strain: Kunming mouse
The source: the The 2nd Army Medical College Experimental Animal Center provides.
Conformity certification number: Shanghai is moving closes the card word No. 107
Body weight: 18-20g
Sex: female.
1.3 transplanted tumor
Mouse S180 sarcoma is gone down to posterity by Shanghai Institute of Pharmaceutical Industry and to keep.
2, experimental technique
Get well-grown mouse S180 sarcoma ascites, dilute with 1: 4 with physiological saline, every mouse armpit subcutaneous vaccination 0.2ml, random packet is divided into control group, endoxan group (CTX group, 20mg/kg, ip * 7), administration (5mg/kg) group, next day is played administration in the inoculation back, the administration volume is the 0.5ml/20g body weight, continuous irrigation stomach 7 days.Inoculate back 10 days and take off neck execution animal, dissect behind the title the weight of animals and get the knurl piece, claim knurl heavy.The result judges according to following formula:
3, experimental result
5 compounds have significant tumor-inhibiting action.Experimental result sees Table 4.
Table 45 compound is to the restraining effect of mouse S180 sarcoma
Compare with control group: * P＜0.05, * * P＜0.01.
Claims (9)
1. Manchurian fir triterpene compound comprises following compounds 1,2,3,4,5:
Compound 1:25,26, three carbon-3 Alpha-hydroxy ring A Er front yard alkane-24-carboxylic acid falls in 27-
Amorphous powder, optical value :+12.1c 0.08, ethanol, ultraviolet maximum absorption wavelength: 226nm; Infrared spectra maximum absorption wave number: 3445,2928,2868,1715,1457,1383,1068,971cm
-1, ESI-MS:415[M-H]
-, high resolution mass spectrum: 467.3170[M+Na]
+: C
27H
44O
3Na, 467.3161;
Compound 2:25,26, three carbon-3 α-methoxy basic ring A Er front yard alkane-24 carboxylic acid falls in 27-
Amorphous powder, optical value :+9.0c 0.16, chloroform, ultraviolet maximum absorption wavelength: 223nm; Infrared spectra maximum absorption wave number: 3445,2955,2924,1700,1456,1382,1098cm
-1, ESI-MS:453[M+Na]
+, high resolution mass spectrum: 453.3329[M+Na]
+: C
28H
46O
3Na, 453.3339;
Compound 3:24,25,26, three carbon-3-carbonyl-9 β hydrogen-lanostane-7-alkene-23-carboxylic acid falls in 27-
Amorphous powder, optical value :+43.5c 0.23, ethanol, ultraviolet maximum absorption wavelength: 229nm; Infrared spectra maximum absorption wave number: 3439,3031,2961,1730,1458,1320,1050,968,668cm
-1, ESI-MS:399[M-H]
-, high resolution mass spectrum: 423.2888[M+Na]
+: C
30H
43O
4Na, 423.2870;
Compound 4:
3,4-open loop-9 β hydrogen-lanostane-4 (28), 7,22,25-tetraene-23,26-lactone-3-carboxylic acid
Amorphous powder, optical value :-83.4c 0.79, chloroform, ultraviolet maximum absorption wavelength: 279nm; Infrared spectra maximum absorption wave number: 3446,2969,2949,1738,1436,1366,1092,962,758cm
-1, ESI-MS:489[M+Na]
+, high resolution mass spectrum: 489.2994[M+Na]
+: C
30H
42O
4Na, 489.2975;
Compound 5: lanostane-7,9 (11), 24-triolefin 26-carboxylic acid
Amorphous powder, optical value :-83.4c 0.79, chloroform, ultraviolet maximum absorption wavelength: 279nm; Infrared spectra maximum absorption wave number: 3446,2969,2949,1738,1436,1366,1092,962,758cm
-1, ESI-MS:489[M+Na]
+, high resolution mass spectrum: 489.2994[M+Na]
+: C
30H
42O
4Na, 489.2975;
Compound 1-4
1H and
13CNMR data CDCl
3
aAnalysis frequency 100MHz
bAnalysis frequency 400MHz.
cAnalysis frequency 150MHz.
dAnalysis frequency 600MHz.
2. the extraction and separation method of Manchurian fir triterpene compound according to claim 1 is characterized in that this method comprises the following steps:
(1) extracts: the dry branches and leaves of Manchurian fir are pulverized, with 8-20 times of volume W/V of 75-95% ethanol refluxing extraction 1-3 time, each 2-3 hour, united extraction liquid, the extracting solution concentrating under reduced pressure becomes fluid extract, and fluid extract is equivalent to 1ml and contains Manchurian fir 0.9-1.1g, fluid extract adds water 1-3 doubly measure W/V dilution after, doubly measure V/V extraction 3-5 time with chloroform 0.5-2, obtain chloroform extraction partly; Described Manchurian fir is picked up from the northeast Changbaishan area, gets its dry pine branch;
(2) separate:, be 100 with volume ratio: 0-1 above-mentioned chloroform extraction part applying silicon plastic column chromatography: 1 petrol ether/ethyl acetate system gradient elution, thin-layer chromatography detects, and collects the flow point that contains compound 2,1,3,5,4 respectively by eluotropic series; The compound of each flow point is respectively through sephadex chromatography, is 1: 1 chloroform/methanol wash-out with volume ratio, and again through the C18 reversed phase column chromatography, with volume ratio 6: 4-10: 0 methanol is carried out wash-out, and thin-layer chromatography detects, and finally obtains 5 compounds.
3. the application of Manchurian fir triterpene compound in the preparation cancer therapy drug according to claim 1.
4. according to the application of claim 3, it is characterized in that described Manchurian fir triterpene compound is 25,26, three carbon-3 Alpha-hydroxy ring A Er front yard alkane-24-carboxylic acid falls in 27-.
5. according to the application of claim 3, it is characterized in that described Manchurian fir triterpene compound is 25,26, three carbon-3 α-methoxy basic ring A Er front yard alkane-24 carboxylic acid falls in 27-.
6. according to the application of claim 3, it is characterized in that described Manchurian fir triterpene compound is 24,25,26, three carbon-3-carbonyl-9 β hydrogen-lanostane-7-alkene-23-carboxylic acid falls in 27-.
7. according to the application of claim 3, it is characterized in that described Manchurian fir triterpene compound is 3,4-open loop-9 β hydrogen-lanostane-4 (28), 7,22,25-tetraene-23,26-lactone-3-carboxylic acid.
8. according to the application of claim 3, it is characterized in that described medicine is made up of as activeconstituents and conventional pharmaceutical carrier the Manchurian fir triterpene compound.
9. according to the application of claim 3, it is characterized in that described cancer comprises lung cancer, small cell lung cancer, intestinal cancer and mammary cancer.
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| CN103664839A (en) * | 2013-11-12 | 2014-03-26 | 中国人民解放军第二军医大学 | Application of Inula wissmanniana lactone A and derivatives in preparing antineoplastic drugs |
| CN108165496A (en) * | 2017-12-01 | 2018-06-15 | 国家海洋局第三海洋研究所 | Fu Keer sclerotinite 3A00494 and its fermented cpds application in preparation of anti-tumor drugs |
| CN109810160A (en) * | 2019-01-30 | 2019-05-28 | 上海市计量测试技术研究院 | The application of fir triterpene class compound, preparation method and its hepatitis virus resisting |
| CN113197922A (en) * | 2021-05-20 | 2021-08-03 | 郑巍 | Application of cedar extract and fluconazole in preparation of antifungal drugs |
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| CN101565443A (en) * | 2009-04-24 | 2009-10-28 | 中国人民解放军第二军医大学 | New fir triterpene lactone compound, preparation method and application thereof |
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| WO2008130449A2 (en) * | 2006-11-20 | 2008-10-30 | Satori Pharmaceuticals, Inc. | Modulators of amyloid-beta production |
| CN101565443A (en) * | 2009-04-24 | 2009-10-28 | 中国人民解放军第二军医大学 | New fir triterpene lactone compound, preparation method and application thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103664839A (en) * | 2013-11-12 | 2014-03-26 | 中国人民解放军第二军医大学 | Application of Inula wissmanniana lactone A and derivatives in preparing antineoplastic drugs |
| CN103664839B (en) * | 2013-11-12 | 2016-01-13 | 中国人民解放军第二军医大学 | Inula wissmanniana lactone A and derivative thereof are preparing the application in antitumor drug |
| CN108165496A (en) * | 2017-12-01 | 2018-06-15 | 国家海洋局第三海洋研究所 | Fu Keer sclerotinite 3A00494 and its fermented cpds application in preparation of anti-tumor drugs |
| CN108165496B (en) * | 2017-12-01 | 2020-09-08 | 国家海洋局第三海洋研究所 | Application of sclerotinia Rickettii 3A00494 and fermentation compound thereof in preparation of antitumor drugs |
| CN109810160A (en) * | 2019-01-30 | 2019-05-28 | 上海市计量测试技术研究院 | The application of fir triterpene class compound, preparation method and its hepatitis virus resisting |
| CN109810160B (en) * | 2019-01-30 | 2021-12-07 | 上海市计量测试技术研究院 | Fir triterpenoid, preparation method and application thereof in resisting hepatitis virus |
| CN113197922A (en) * | 2021-05-20 | 2021-08-03 | 郑巍 | Application of cedar extract and fluconazole in preparation of antifungal drugs |
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|---|---|
| CN102030800B (en) | 2013-08-21 |
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