CN110294766B - Supercritical fluid extraction of chicken bone vetiver extract and method and application thereof - Google Patents
Supercritical fluid extraction of chicken bone vetiver extract and method and application thereof Download PDFInfo
- Publication number
- CN110294766B CN110294766B CN201910454438.XA CN201910454438A CN110294766B CN 110294766 B CN110294766 B CN 110294766B CN 201910454438 A CN201910454438 A CN 201910454438A CN 110294766 B CN110294766 B CN 110294766B
- Authority
- CN
- China
- Prior art keywords
- extract
- petroleum ether
- acetone
- extraction
- fraction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention belongs to the technical field of medicine extraction, and particularly relates to a chicken bone vetiver extract extracted by supercritical fluid and a preparation method thereofA method and an application. The chicken bone extract is named as a compound J-1, and the specific structural formula is as follows:
. The compound extracted by the invention has easily obtained raw materials, is easy to industrialize, can be prepared into different formulations according to requirements, and has great social benefit. The compound extracted by the invention has high purity and high anti-tumor activity, has the effects of resisting proliferation and inducing apoptosis, and has the potential of being used as a candidate of anti-cancer therapy.
Description
Technical Field
The invention belongs to the technical field of medicine extraction, and particularly relates to a chicken bone vetiver extract extracted by supercritical fluid, and a method and application thereof.
Background
The genus croton is an euphorbiaceae family, with over 1300 species worldwide, a large genus widely distributed in tropical and subtropical regions. There are approximately 21 croton plants growing in china, some of which have long been used to relieve dysmenorrhea and to mediate medical treatments for dyspepsia and malaria. Plants of the genus croton are known for their various terpenoids and possess a wide range of biological activities. In addition, alkaloids, flavanones, lignans, polyphenolic compounds, phenylbutyric acid and peptides are obtained.
Croton crassifolius Geisel is a species of Croton genus, and is mainly distributed in the southern China and other regions of southeast Asia. As a traditional Chinese medicine named "chicken bone fragrant", its root has been used for the treatment of cancer, stomach ache, sore throat and rheumatism. Current phytochemical studies have shown that the major phytochemicals in c. crassifolius are terpenoids, including sesquiterpenes, diterpenes and triterpenes. Diterpenes are considered to be the main and characteristic compounds in c. crassifolius, having various biological activities, such as antiviral and antiangiogenic activities.
Currently, most studies on c. crassifolius focus on the use of its root extract in medicine, and the utilization of its low-polar part is rarely studied. In the prior art, the low polarity portion of the herb is reported to be rich in active compounds, but specific studies have been less. There is no description about the extraction of the compound of the present invention.
Disclosure of Invention
The invention aims to provide a supercritical fluid extracted Chinese eaglewood root extract, which has high anti-tumor activity and the effects of resisting proliferation and inducing apoptosis.
The invention also provides an extraction method for extracting the Chinese eaglewood root extract by the supercritical fluid.
The invention also aims to provide application of the chicken bone vetiver extract.
The technical scheme adopted by the invention for realizing the purpose is as follows:
a supercritical fluid extraction method of a radix eleostemi japonicae extract comprises the following steps:
the invention also provides a method for extracting the Chinese eaglewood root extract by the supercritical fluid, which comprises the following steps:
(1) taking the dry root of the chicken bone, crushing, sieving by a 40-mesh sieve, weighing a sample, and filling the sample into supercritical CO2In a reaction kettle of a fluid extraction instrument, firstly carrying out static extraction, then carrying out dynamic extraction, using methanol as an entrainer to obtain a dark yellow extract, dissolving the extract with warm water, and fully extracting with dichloromethane to obtain an extract;
(2) preparing an eluent, eluting 5.0L of the eluent at each proportion by using a polar gradient of petroleum ether/acetone (50: 1-1: 2), analyzing the extract by using thin-layer chromatography, selecting a petroleum ether-acetone separation system, and performing coarse separation by using a 100-mesh 200-mesh silica gel dry method for column packing; detecting and merging by thin-layer chromatography to obtain 5 components A1-A5;
(3) subdividing A4 by using 200-300 mesh silica gel; preparing petroleum ether-ethyl acetate system eluent for gradient elution with polarity gradient of 8:1-5:1, and combining thin layer chromatography detection into 6 parts A4a-A4 f; subjecting the A4f part to Sephadex LH-20 column chromatography, repeatedly eluting with dichloromethane-methanol, subjecting the middle part to C18 column and 65-85% CH3OH/H2Gradient eluting with O (2 mL/min, 20 min), detecting with ultraviolet detector at 210 nm, concentrating 14.600 min fraction, and adding 55% CH3CN/H2And (3) isocratic elution of O (2 mL/min) to obtain a chicken bone extract named as a compound J-1.
Further, the static extraction is carried out for 30 min under the conditions of 25 MPa of pressure and 35 ℃.
Further, during the dynamic extraction, CO2The flow rate was 5.0L/min, methanol was used as entrainer and the flow rate was 5.4 mL/min.
Further, said a1 is a petroleum ether/acetone =50:1-30:1 fraction; a2 is a petroleum ether/acetone =15:1 fraction; a3 is a petroleum ether/acetone =10:1-8:1 fraction; a4 is a petroleum ether/acetone =6:1-2:1 fraction; a5 is a petroleum ether/acetone =1:1-1:2 fraction.
Further, A4a-A4f are respectively: 0-800 mL, 800-2000 mL, 2000-2800 mL, 2800-4000 mL, 4000-52000 mL, 5200-6000 mL.
Further, in the step (3), the volume ratio of the dichloromethane to the methanol is 1: 1.
the invention also provides application of the compound extracted by the extraction method in preparation of antitumor drugs.
The compound extracted from the chicken bone incense can inhibit the proliferation of A549 cells and block the A549 cell cycle in the G2/M phase. The compounds increase the Bax/Bcl-2 ratio in A549 cells, leading to a breakdown of mitochondrial membrane potential, followed by cytochrome C release and activation of the caspase cascade, leading to cleavage of PARP and ultimately apoptosis. Natural diterpenoid 1 was isolated by active chase methods and its potential as a candidate for future anti-cancer therapy was demonstrated by anti-proliferation evaluations.
The invention has the beneficial effects that:
(1) the compound extracted by the invention has easily obtained raw materials, is easy to industrialize, can be prepared into different formulations according to requirements, and has great social benefit.
(2) The compound extracted by the invention has high purity and high anti-tumor activity, has the effects of resisting proliferation and inducing apoptosis, and has the potential of being used as a candidate of anti-cancer therapy.
Drawings
FIG. 1 is a spectrum of HMBC and RORSY, and ECD spectrum of compound J-1.
FIG. 2 is a graph showing the effect of varying concentrations of Compound J-1 on the migration of A549 cells.
FIG. 3 is a graph showing staining with Hoechst33258 after treating lung cancer cells A549 cells with different concentrations of Compound J-1.
Detailed Description
The technical solution of the present invention is further explained and illustrated by the following specific examples.
Example 1
(1) Materials and methods
Crassifolius was purchased from the chinese herbal medicine market in china, anhui, mn 10 months in 2017. The species was identified by professor for single-grown Steel (IAST, SAAS) of institute of agricultural products, college of agricultural sciences of Shandong province, Jinan, China. A sample of the certificate (No. 17-10-29) was stored in the IAST bioactive and functional food laboratory of SAAS.
(2) The extraction process comprises the following steps:
firstly, taking the dried root of the chicken bone, crushing the root by a traditional Chinese medicine crusher, and sieving the crushed root by a 40-mesh sieve (450 mu m). Weighing 2.0 kg of sample, and loading the sample into supercritical CO for 10 times2200 g each time in a reaction kettle (650 mL) of a fluid extractor. At 25 MPa, 35oStatic extraction for 30 min under C, followed by dynamic extraction for 30 min (CO)2Flow rate 5.0L/min), methanol was used as entrainer (flow rate 5.4 mL/min). Obtaining 100.4 g of dark yellow extract, dissolving the extract with 500 mL of warm water, and fully extracting with dichloromethane r (500 mL multiplied by 5 times) to obtain the extractTaking 77.0 g;
② a petroleum ether-acetone separation system is selected by thin-layer chromatography analysis. And (5) packing the column by a 100-plus 200-mesh silica gel dry method for rough separation. Preparing an eluent, eluting 5.0L of the eluent at each ratio by using a polar gradient of petroleum ether/acetone (50: 1-1: 2), and detecting and combining by using a thin-layer chromatography to obtain 5 components A1-A5.
③ A4 (petroleum ether/acetone =6:1-2:1 fraction, 7.3 g) was subdivided with 200-mesh 300-mesh silica gel. Preparing petroleum ether-ethyl acetate system eluate, gradient eluting with polarity gradient of 8:1-5:1, separating colorless blocky crystal at 8:1 part, detecting impurities by thin layer chromatography, dissolving in methanol, further purifying with semi-preparative liquid phase, separating with C18 column and 65-85% CH3OH/H2Gradient eluting with O (2 mL/min, 20 min), detecting with ultraviolet detector at 210 nm to obtain compound J-11 (4.1 mg, t)R16.800 min); the mother liquors were again checked by thin layer chromatography to pool into 6 fractions A4a-A4 f; subjecting the A4f part to Sephadex LH-20 column chromatography, repeatedly eluting with dichloromethane-methanol (1:1), collecting the middle part, subjecting to C18 column and 65-85% CH3OH/H2Gradient eluting with O (2 mL/min, 20 min), detecting with ultraviolet detector at 210 nm, concentrating 14.600 min fraction, and adding 55% CH3CN/H2Isocratic elution of O (2 mL/min) gave Compound J-1 (2.4 mg, t)R23.492 min), the specific structural formula is as follows:
(3) experimental procedures
Optical rotations were measured on an Autopol VI polarimeter at room temperature. Infrared Radiation (IR) spectra were recorded using a NICOLET IR200 FT-IR spectrophotometer. UV data were obtained on a Shimadzu UV-2550 spectrophotometer. ECD data were obtained on a JASCO 810 spectrophotometer. At 600 MHz (using a Bruker Avance DRX-400 spectrometer1H) And 150 MHz of (13C) NMR spectra were recorded. HR-ESI-MS was performed on an Agilent Technologies 6224 TOF LC-MS apparatus. Silica gel (200-300 mesh, Qingdao Marine Chemical, Inc.) and ODS (SiliaSphere C18S 03230G-A, Silicacle)Column Chromatography (CC) was performed. Semi-immobilized HPLC was performed on an Agilent Technologies 1260 Infinity coupled with an Agilent G1321B DAD detector and a Silgreen GH0525010C18A column (250X 10mm, 5 μm, 120A).
(4) Cell lines and cell cultures
The a549 lung cancer cell line and the HeLa cervical cancer cell line were purchased from the cell bank type culture collection of the chinese academy of sciences (shanghai, china). A549 cells were cultured in RPMI-1640 (HyClone) containing 10% fetal bovine serum (Gibco) and 100U/mL penicillin-streptomycin (HyClone). HeLa cells were cultured in DMEM (HyClone) medium containing 10% fetal bovine serum (Gibco) and 100U/mL penicillin-streptomycin (HyClone). All cells were incubated at 37 deg.C, 95% air and 5% CO2Under humid conditions.
(5) Discussion of results
The compound J-1 separated by the invention is white powder and has a molecular formula C21H22O7By HR-ESI-MS inm/zThe following measurements were made: 387.1311 [ M + H] +（cal. [C21H22O7 + H]+: 387.1366) comprising 11 unsaturations. IR absorption band 1 corresponds to a furan ring (3142, 1452, 863 cm)-1) And typical lactones (1753,1194 cm)-1) The presence of absorption.
1 of1H-NMR spectrum showed methyl [ delta ]H1.15（3H, d, J = 7.2 Hz）]Methoxy [ delta ]H3.79（3H, s）]And a characteristic beta-substituted furan ring [ delta ]H7.49（1H, m）, δH7.47（1H, m）, δH 6.42（1H，m）]。
13The C-NMR spectrum has a 21-carbon signal, deltaC134.2 and deltaC132.0 shows unsaturated bonds. DeltaC 176.1，δC172.4 and δC168.2 shows that three ester groups are attached to Compound 1. With the help of HSQC spectra, the carbon signal is assigned a methyl group (. delta.) (C16.1), one methoxy group (. delta.) andC53.2) and furan Ring at δC 144.4，δC 139.6，δC 124.6，δC108.0. The HMBC correlation of H-14 (Δ 6.42,1H, m) with C-13 (Δ 124.6), C-15 (Δ 144.4) and C-16 (Δ 139.6) (FIG. 1) further confirms the presence of the furan ring. The molecular weight distribution of the peptide was determined from H-12 (5.48, 1H, t,J HMBC correlations for = 8.64 Hz) to C-13 (δ 124.6), C-14 (δ 108.0) and C-16 (δ 139.6) indicate that the furan ring is located at C-12. H-17 (. delta.1.15, 3H, d,J= 7.20 Hz) is associated with C-7 (δ 32.4) and C-9 (δ 53.0), indicating that the methyl group (δ 34.8) is located at the C-8 position. Delta associated with C-19H3.79 (3H, s) indicate that methoxy is attached to the structure. Furthermore, H-3 (. delta.1.38) is associated with C-19, indicating that the methylmethoxy group is located at C-4. All assigned proton and carbon signals are summarized in table 1.
TABLE 1
The configuration of 1 was determined by ECD and ROESY experiments (fig. 1). The negative absorption effect at 220-240 nm observed in the ECD spectrum is consistent with the 9R and 12S configurations. The ROE correlation of H-6 (. delta.5.19)/H-8 (. delta.1.97)/H-12 (. delta.5.48) indicates that these protons are α -oriented, indicating that the methyl group at C-8 and the methoxy group attached at C-4 are on the other side of the plane. The absolute configuration of J-1 was confirmed to be 4S, 6R, 8S, 9R and 12S, and compound J-1 was finally named crassifolius P.
② cytotoxic Activity of Compound J-1
The compound extracted by the invention has cytotoxic activity against A549 and HeLa similar to that of positive control medicament matrine, and concretely, the compound extracted by the invention has high cytotoxic activity against A549 cells shown in Table 2. HL-7702 is a normal human hepatocyte cell line used to evaluate the cytotoxic effects of our isolated compounds, with the result that hepatocytes are less sensitive to the cytotoxic effects of the test compounds, with IC50 values as high as 100. mu.M. These results indicate that compound J-1 has very significant selectivity against cancer cell lines, particularly A549.
TABLE 2
I scratch test
Inoculating A549 cells in logarithmic growth phase in a 6-well plate, incubating overnight in a 37-degree incubator, scratching with a 200-microliter gun head when the cells reach monolayer fusion, immediately placing under an inverted microscope to randomly select a visual field for photographing, and recording the scratch width at 0 h. Then, compound J-1 (0, 15,25, 35. mu.M) was added to the cells at various concentrations, and photographed at various time points of the drug action to observe the migration distance of the cells. And quantified using ImageJ and GraphPad software.
The effect of different concentrations of the extracted compounds of the present invention on the migration of a549 cells was examined by scratch assay, as shown in fig. 2. The results showed that the rate of cell migration gradually decreased with increasing drug concentration compared to the control group of 0. mu.M. The quantitative results showed that at 35. mu.M, the migration capacity of the cells decreased by 50%. The above results indicate that compound J-1 is able to inhibit migration of a549 human lung cancer cells in a concentration-dependent manner.
II Compound J-1 can promote A549 cell apoptosis
Logarithmic growth phase A549 cells were seeded in 12-well plates, incubated overnight in a 37 ℃ incubator, the original medium in the wells was discarded, and medium containing varying concentrations of compound J-1 (0, 15,25, 35. mu.M) was added to the cells until the compound was allowed to act for 48 h. Discarding the culture medium in the wells, washing with PBS once, adding 4% paraformaldehyde for fixing for 15min, washing with PBS three times, then adding Hoechst3328 dye solution, incubating at 37 ℃ for 15min, discarding the supernatant, washing with PBS for 2-3 times, then placing under a fluorescence microscope for observation, and taking a picture. The cell nucleus of normal cells can be lightly stained, and when the cells are apoptotic, the cell nucleus of the apoptotic cells can be seen to be deeply stained and bright, or be densely stained in a broken block shape and appear as apoptotic bodies.
Hoechst33258 is a dye that stains the nucleus, reflecting the amount of apoptosis from one side. According to the present invention, after treating lung cancer cell A549 cells with compound J-1 ((0, 15,25, 35. mu.M)) at various concentrations, staining was performed with Hoechst33258, as shown in FIG. 3, and as a result, it was found that as the concentration was increased, there were more deeply stained cells, concentrated nuclei and the appearance of apoptotic bodies, as compared with the control group. The fact that the transdermal compound J-1 can induce apoptosis of A549 human lung cancer cells is proved, and the apoptosis rate is increased along with the increase of the concentration of the medicine.
Claims (3)
1. A method for extracting a radix clematidis extract by supercritical fluid is characterized in that,
the structural formula of the extract is as follows:
the method specifically comprises the following steps:
(1) taking the dry root of the chicken bone, crushing, sieving by a 40-mesh sieve, weighing a sample, and filling the sample into supercritical CO2In a reaction kettle of a fluid extraction instrument, firstly carrying out static extraction, then carrying out dynamic extraction, using methanol as an entrainer to obtain a dark yellow extract, dissolving the extract with warm water, and fully extracting with dichloromethane to obtain an extract;
(2) preparing an eluent, wherein the polarity gradient is petroleum ether/acetone, the ratio of the petroleum ether to the acetone is 50: 1-1:2, eluting 5.0L of the eluent in each ratio, analyzing the extract by thin-layer chromatography, selecting a petroleum ether-acetone separation system, and performing coarse separation by using a 100-mesh 200-mesh silica gel dry method for column packing; detecting and merging by thin-layer chromatography to obtain 5 components A1-A5;
the A1 is a petroleum ether/acetone =50:1-30:1 part; a2 is a petroleum ether/acetone =15:1 fraction; a3 is a petroleum ether/acetone =10:1-8:1, 8.5 g fraction; a4 is a petroleum ether/acetone =6:1-2:1 fraction; a5 is a petroleum ether/acetone =1:1-1:2 fraction;
(3) subdividing A4 by using 200-300 mesh silica gel; preparing petroleum ether-ethyl acetate system eluent for gradient elution with polarity gradient of 8:1-5:1, and combining thin layer chromatography detection into 6 parts A4a-A4 f; subjecting the A4f part to Sephadex LH-20 column chromatography, repeatedly eluting with dichloromethane-methanol, subjecting the middle part to C18 column chromatography65-85% CH3OH/H2Gradient elution of O, the CH3OH/H2O flow rate of 2 mL/min for 20 min, detecting with ultraviolet detector at 210 nm, concentrating 14.600 min fraction, and adding 55% CH3CN/H2Isocratic elution of O, said CH3CN/H2The flow rate of O is 2 mL/min, and the chicken bone extract is obtained and named as compound J-1;
the volume ratio of the dichloromethane to the methanol is 1: 1;
a4a-A4f are respectively: 0-800 mL, 800-2000 mL, 2000-2800 mL, 2800-4000 mL, 4000-52000 mL, 5200-6000 mL.
2. The extraction process according to claim 1, wherein the static extraction is carried out at a pressure of 25 MPa and a temperature of 35 ℃ for 30 min.
3. The extraction method according to claim 1 or 2, wherein the dynamic extraction is performed by using CO2The flow rate was 5.0L/min, methanol was used as entrainer and the flow rate was 5.4 mL/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910454438.XA CN110294766B (en) | 2019-05-29 | 2019-05-29 | Supercritical fluid extraction of chicken bone vetiver extract and method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910454438.XA CN110294766B (en) | 2019-05-29 | 2019-05-29 | Supercritical fluid extraction of chicken bone vetiver extract and method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110294766A CN110294766A (en) | 2019-10-01 |
| CN110294766B true CN110294766B (en) | 2021-08-03 |
Family
ID=68027362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910454438.XA Active CN110294766B (en) | 2019-05-29 | 2019-05-29 | Supercritical fluid extraction of chicken bone vetiver extract and method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110294766B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105477432A (en) * | 2015-12-25 | 2016-04-13 | 林海燕 | Medicine composition for treating tumors |
| CN110540530B (en) * | 2019-05-29 | 2022-12-16 | 山东省农业科学院农产品研究所 | Chicken bone vetiver extract and supercritical fluid extraction method and application thereof |
| CN110294723A (en) * | 2019-05-29 | 2019-10-01 | 山东省农业科学院农产品研究所 | A kind of extracting method and its application of Thickleaf Croton Root root extract |
-
2019
- 2019-05-29 CN CN201910454438.XA patent/CN110294766B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN110294766A (en) | 2019-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Chen et al. | Caffeoylquinic acid derivatives isolated from the aerial parts of Gynura divaricata and their yeast α-glucosidase and PTP1B inhibitory activity | |
| EP2329816B1 (en) | An anti-cancer active substance from antrodia camphorata, method for preparing the same and use thereof | |
| CN109897077B (en) | Compound Oleraceamide E in purslane, and extraction separation method and application thereof | |
| Li et al. | Lignans from the heartwood of Streblus asper and their inhibiting activities to hepatitis B virus | |
| CN110272342B (en) | Naphthoic acid compound in purslane and extraction and separation method and application thereof | |
| You et al. | Cytotoxic cardenolides from the root bark of Calotropis gigantea | |
| CN106588838B (en) | The rich volt lactone of hydroxyl dihydro and its extraction separation method in purslane | |
| Cho et al. | Phytochemical constituents of Salsola komarovii and their effects on NGF induction | |
| Liu et al. | Two new sesquiterpenes from Artemisia sieversiana | |
| Suh et al. | Secoiridoid glycosides from the twigs of Ligustrum obtusifolium possess anti-inflammatory and neuroprotective effects | |
| Liu et al. | Monomeric and dimeric ent-kauranoid-type diterpenoids from rabdosia japonica and their cytotoxicity and anti-HBV activities | |
| CN101899082B (en) | Triterpenoid saponin compound, application and preparation method | |
| CN109336747B (en) | Oleralignan in purslane, extraction and separation method thereof and application thereof | |
| CN110540530B (en) | Chicken bone vetiver extract and supercritical fluid extraction method and application thereof | |
| CN113264886A (en) | Extraction and separation method and application of pyridazine compound in purslane | |
| CN110294766B (en) | Supercritical fluid extraction of chicken bone vetiver extract and method and application thereof | |
| CN115991692B (en) | Preparation method and application of spirodienone lignan compound in Isatis tinctoria | |
| CN111548327B (en) | Carbon-reduced kaurane diterpene, preparation method thereof and application thereof in preparation of antitumor drugs | |
| CN101190259A (en) | Southern magnolia total lactone extract and preparation method and application thereof | |
| CN114213375B (en) | Sesquiterpene lactone compound and preparation method and application thereof | |
| CN115521245A (en) | Alkaloid compound in purslane and extraction and separation method and application thereof | |
| CN110305094B (en) | Two flavonoid compounds in purslane and extraction and separation method and application thereof | |
| CN110294733B (en) | Peroxide bond-containing compound Oleracone I in purslane, and extraction separation method and application thereof | |
| CN110194755B (en) | Compound Oleracone H in purslane, extraction and separation method and application thereof | |
| CN113968869A (en) | Guaiane sesquiterpene lactone compound Artemvulactone and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |