CN104398532A - Application of cardiac glycoside compound 12beta-hydroxycalotropin - Google Patents

Application of cardiac glycoside compound 12beta-hydroxycalotropin Download PDF

Info

Publication number
CN104398532A
CN104398532A CN201410662253.5A CN201410662253A CN104398532A CN 104398532 A CN104398532 A CN 104398532A CN 201410662253 A CN201410662253 A CN 201410662253A CN 104398532 A CN104398532 A CN 104398532A
Authority
CN
China
Prior art keywords
hydroxycalotropin
cardiac glycoside
glycoside compound
methanol
column chromatography
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.)
Granted
Application number
CN201410662253.5A
Other languages
Chinese (zh)
Other versions
CN104398532B (en
Inventor
王茂媛
晏小霞
王祝年
王建荣
王清隆
王鹏
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tropical Crops Genetic Resources Institute CATAS
Original Assignee
Tropical Crops Genetic Resources Institute CATAS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Tropical Crops Genetic Resources Institute CATAS filed Critical Tropical Crops Genetic Resources Institute CATAS
Priority to CN201410662253.5A priority Critical patent/CN104398532B/en
Priority claimed from CN201310124216.4A external-priority patent/CN103191143B/en
Publication of CN104398532A publication Critical patent/CN104398532A/en
Application granted granted Critical
Publication of CN104398532B publication Critical patent/CN104398532B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention discloses an application of a cardiac glycoside compound 12beta-hydroxycalotropin in preparation of medicine for treating and preventing tumors. The cardiac glycoside compound 12beta-hydroxycalotropin has remarkable antitumor activity and can be used as a lead compound for treating the tumors. Meanwhile, an extraction separation method of the cardiac glycoside compound 12beta-hydroxycalotropin is simple, practicable, low in cost, high in efficiency and yield and good in extraction quality.

Description

A kind of purposes of cardiac glycoside compound
The application is the divisional application of " a kind of novelty teabag of cardiac glycoside compound ", and the applying date of original application is on April 11st, 2013, and application number is: 201310124216.4.
Technical field
The present invention relates to cardiac glycoside compound, be specifically related to a kind of cardiac glycoside 12 β-hydroxycalotropin and uses thereof.
Background technology
Tumor is very large to the threat of human health and life, and it and cardiovascular disease have become two large difficulties medically, at two of the whole world formation cause of death.In the whole world 5,200,000,000 population, about there are 7,000,000 people's new trouble tumors every year, about have more than 500 ten thousand people to die from tumor every year, almost just have a tumor patient death every 6 seconds.About there are 1,500,000 people's new trouble tumors in China at present every annual, about has 800,000 people to die from tumor every year.Existing antitumor drug all can not thoroughly be cured effectively.Simultaneously due to the continuous discovery of novel tumor, people are forced to strive to find new antitumor drug.For a long time, from medicinal plants especially tropical medicinal plants, seeking antitumor medicine becomes a common aspiration of various countries' medical science, pharmacy, chemistry and biologist.Research shows, antitumor drug 70% derives from the torrid zone or subtropical plant.After vincristin, the discovery of paclitaxel and derivant Epothilones thereof, makes this work achieve breakthrough progress.But, because some antineoplastic component is extremely low at plant intensive amount, some plant or rareness species in imminent danger, and plant growing is slow, excessively excavate the extinction that may cause these species, these factors limit the development of anti-tumor botanical.
Radix Calotropis giganteae [Calotropis gigantea (L.) Dryand ex Ait.f.] is asclepiadaceae (Asclepiadaceae) Calotropis (Calotropis) plant.The ground such as Hainan, Guangdong, Sichuan and Yunnan are mainly distributed in China.Radix Calotropis giganteae Herb is poisonous, and the white juice at its root, stem, leaf, flower, fruit and each position is all pharmaceutically acceptable, has antibacterial, antiinflammatory, anthelmintic, reduces phlegm, the effect such as removing toxic substances, is a kind of common medicine among the people.Domestic and international research shows Radix Calotropis giganteae mainly containing cardiac glycoside compounds, is its toxic component.But it is current or unknown whether to have antitumor action about the cardiac glycoside compound 12 β-hydroxycalotropin in Radix Calotropis giganteae.
Summary of the invention
A kind of cardiac glycoside compound 12 β-hydroxycalotropin is the object of the present invention is to provide to prepare the purposes in the medicine with treatment and prophylaxis of tumours effect.
Present inventor has carried out the test of extracting and developing, purification and anti-tumor activity to the cardiac glycoside compounds 12 β-hydroxycalotropin in Radix Calotropis giganteae and has found, the cardiac glycoside compound 12 β-hydroxycalotropin in this Radix Calotropis giganteae has antineoplastic novelty teabag.
Above-mentioned purpose of the present invention is achieved by the following technical solution: cardiac glycoside compound 12 β-hydroxycalotropin is preparing the purposes in the medicine with treatment and prophylaxis of tumours effect, and the molecular formula of described cardiac glycoside compound 12 β-hydroxycalotropin is C 29h 40o 10, structural formula is as follows:
Tumor of the present invention is mainly cancer of biliary duct, renal carcinoma, cancer of pancreas, colorectal carcinoma, bladder cancer, breast carcinoma, uterus carcinoma, ovarian cancer, colorectal cancer, hepatocarcinoma, gallbladder cancer, cancer of bile ducts, acute leukemia, malignant lymphoma, cerebroma, bone tumor, melanoma, glioma, oral cancer, nasopharyngeal carcinoma, pulmonary carcinoma or gastric cancer etc.
Cardiac glycoside compound 12 β-hydroxycalotropin of the present invention can utilize multiple separation means such as comprising adsorbent resin column chromatography, silica gel column chromatography, reversed-phase silica gel column chromatography, gel filtration chromatography, reduced pressure chromatography to obtain from Radix Calotropis giganteae, or is obtained by synthesis and semi-synthetic means.Combine with suitable excipient, conventionally make various dosage form.
The preferred preparation method of cardiac glycoside compound 12 β-hydroxycalotropin of the present invention is as follows:
A, choose Radix Calotropis giganteae stem, after pulverizing, add ethanol, lixiviate 3 ~ 4 times, each 6 ~ 8 days, merge lixiviating solution, be evaporated to the ethanol extraction obtaining Radix Calotropis giganteae without alcohol taste;
B, the ethanol extraction of Radix Calotropis giganteae is scattered in water and makes Radix Calotropis giganteae suspension, be 1:3,1:2 and 1:1 by the volume ratio of Radix Calotropis giganteae suspension and petroleum ether respectively, with petroleum ether to after Radix Calotropis giganteae suspension re-extract, retain the aqueous phase after petroleum ether extraction;
C, filtered by the aqueous phase after petroleum ether extraction, filtrate be separated with D-101 macroporous adsorbent resin column chromatography, and use water and methanol-eluted fractions successively, collect meoh eluate, concentrating under reduced pressure obtains methanol extract after reclaiming methanol;
D, by methanol extract through decompression silica gel column chromatography, be respectively 100:1,50:1,25:1,10:1,5:1,2:1 and 0:100 as eluant using the volume ratio of chloroform and methanol, gradient elution carried out to decompression silicagel column, respectively must crude extract Fr.1 ~ Fr.7;
E, by step D gained crude extract Fr.4 through silica gel column chromatography, be respectively 10:1,8:1,6:1,4:1,2:1,0:1 as eluant using the volume ratio of chloroform and methanol, gradient elution carried out to silicagel column, obtain 6 part Fr.4-1 ~ Fr.4-6;
F, by the Fr.4-2 of E step through silica gel column chromatography, adopt chloroform and acetone to carry out eluting as eluant, adopt TLC thin layer chromatography to collect identical composition during eluting, obtain 6 part Fr.4-2-1 ~ Fr.4-2-6; Fr.4-2-3 is carried out successively Sephadex LH-20 gel filtration chromatography, reversed phase column chromatography and silica gel column chromatography again, finally obtain cardiac glycoside compound 12 β-hydroxycalotropin.
In steps A of the present invention, the mass volume ratio of Radix Calotropis giganteae stem and ethanol is 1kg:1 ~ 3L; The volumn concentration of described ethanol is 92 ~ 98%.
In step B of the present invention with petroleum ether to after Radix Calotropis giganteae suspension re-extract 3 times, retain the aqueous phase after petroleum ether extraction.
In step F of the present invention, the volume ratio of chloroform and acetone is 4:5; The gel column adopted during gel filtration chromatography is Sephadex LH-20 gel column, and during gel filtration chromatography, eluting solvent adopts volumn concentration to be the ethanol of 95%; The chloroform of the eluting solvent again adopted during silica gel column chromatography to be volume ratio be 11:1:1, methanol and acetone mixed solvent.
The solvent adopted in above-mentioned steps A, B, C, D, E, F such as petroleum ether, chloroform, methanol, ethanol etc. are technical grade solvent, use after heavily steaming.
Silicagel column, gel column and the reversed-phase column etc. that use in above-mentioned D, E, F step are conventional equipment of the prior art.
Tool of the present invention has the following advantages: cardiac glycoside compound 12 β-hydroxycalotropin provided by the invention has significant anti-tumor activity, can be used as the lead compound for the treatment of tumor; Meanwhile, extraction separation method provided by the invention is simple, and cost is low, and efficiency is high, and yield is high, and extract quality is good.
Detailed description of the invention
Below in conjunction with instantiation, the present invention is further elaborated, but do not limit the present invention.
Embodiment 1
A, by Radix Calotropis giganteae (Calotropis gigantea) stem 25.4kg natural air drying pulverize after, by Radix Calotropis giganteae sample: ethanol water is about the mass/volume ratio (kg/L) of 1:2, by 50L volume fraction be 95% ethanol water fully mix with 25.4kg Radix Calotropis giganteae sample, sealing, in room temperature lixiviate 3 times, each 7 days, filter and merge lixiviating solution, be evaporated to and obtain ethanol extraction without alcohol taste;
B, at room temperature, ethanol extraction is scattered in water and makes suspension, by ethanol extract: the volume ratio of petroleum ether=1:3,1:2,1:1, with petroleum ether to ethanol extract re-extract 3 times, concentrating under reduced pressure obtains petroleum ether extractum (254.1g) after reclaiming petroleum ether;
C, filtered by the water liquid after petroleum ether extraction, be separated by filtrate D-101 macroporous adsorbent resin column chromatography, use water and methanol-eluted fractions successively, collect meoh eluate, concentrating under reduced pressure reclaims after methanol, obtains methanol extract (255.7g);
D, by methanol extract through decompression silica gel column chromatography, with chloroform: the eluant of methanol=100:1,50:1,25:1,10:1,5:1,2:1,0:100 volume ratio, carry out gradient elution, obtain 7 part Fr.1 ~ Fr.7 respectively;
E, by D step chloroform: the Fr.4 (38.4g) that methanol=10:1 eluting obtains through silica gel column chromatography, with chloroform: methanol=10:1,8:1, the eluant of 6:1,4:1,2:1 volume ratio carries out gradient elution, finally use methanol-eluted fractions, obtain 6 part Fr.4-1 ~ Fr.4-6;
F, by the Fr.4-2 (16.7g) of E step through silica gel column chromatography, with chloroform: the eluant of acetone=4:5 volume ratio carries out eluting, then TLC thin layer chromatography is adopted to collect identical composition, obtain 6 parts, the 3rd part in these 6 parts, namely Fr.4-2-3, Fr.4-2-3 (2.0g) is carried out successively Sephadex LH-20 gel filtration chromatography (volume fraction is the ethanol elution of 95%), reversed phase column chromatography, and silica gel column chromatography (chloroform: methanol: acetone=11:1:1 eluting), finally obtain cardiac glycoside compound 12 β-hydroxycalotropin (98.2mg).
Embodiment 2
By the Fr.4-1 (3.2g) of E step in embodiment 1 after column chromatography, with chloroform: the eluant of methanol=25:1 volume ratio carries out eluting, adopt TLC thin layer chromatography to collect identical composition, obtain 7 part Fr.4-1-1 ~ Fr.4-1-7; By Fr.4-1-4 (869.5mg) through silica gel column chromatography, use chloroform successively: methanol=40:1, chloroform: the eluant of acetone=6:2 volume ratio carries out eluting, finally obtain cardiac glycoside compound calotropin (109.9mg).Research finds, the carbon that the difference on this compound and object compound structure of the present invention is 12 does not have hydroxyl, and the carbon of object compound of the present invention 12 has hydroxyl to replace.The anti-IC of these two compounds is found in further anti tumor activity in vitro test 50value significant difference (see table 2).
Embodiment 3
The Structural Identification of cardiac glycoside compound 12 β-hydroxycalotropin:
Utilize spectral technique, comprise ultraviolet, infrared, nuclear magnetic resonance, NMR and high resolution mass spectrum analysis, identify the structure of the cardiac glycoside compound 12 β-hydroxycalotropin in embodiment 1.Use 2D-NMR technology to the cardiac glycoside compound 12 β-hydroxycalotropin's of Late Cambrian in Radix Calotropis giganteae stem 13c-NMR, 1h-NMR data have carried out belonging to (seeing the following form 1).
Be below the physicochemical constant of cardiac glycoside compound 12 β-hydroxycalotropin:
12 β-hydroxycalotropin:C 29h 40o 10, white amorphous powder (methanol), 10% ethanol solution of sulfuric acid shows brown.M.p.214-216 DEG C; [α] d+ 6.4 ° (c=0.045, MeOH); HR-ESI-MS:m/z [M+Na] +583.2318 (calcd.For C 29h 40o 10cl, 583.2310); IR λ max(cm -1): 3433cm -1, 2957cm -1, 2923cm -1, 2852cm -1, 1712cm -1, 1655cm -1, 1648cm -1, 1638cm -1, 1630cm -1, 1459cm -1, 1262cm -1, 1105cm -1, 1025cm -1; UV λ maxnm (MeOH): 218nm. 13c-NMR and 1h-NMR sees the following form 1.
The carbon spectrum of table 1 cardiac glycoside compound 12 β-hydroxycalotropin and hydrogen modal data
Embodiment 4
The contrast experiment of cardiac glycoside compound 12 β-hydroxycalotropin and the test of calotropin anti tumor activity in vitro:
Mtt assay is adopted to test cardiac glycoside compound 12 β-hydroxycalotropin and calotropin, to gastric carcinoma cells (SGC-7901), human gastric adenocarcinoma (KKLS, MKN-28, MKN-45), people's chronic myeloid leukemia cells (K562), human mouth epidermal carcinoma cell (KB), human breast cancer cell (MCF7), human lung carcinoma cell (NCI-H187), people's fibrosarcoma of bone cell (HT-1080), human osteosarcoma cell (G-292), human osteosarcoma cell (KHOS/NP), the anti tumor activity in vitro (the results are shown in Table 2) of the cell strains such as Human Prostate Cancer Cells (LNCap).
Activity test method is as follows:
Negative control group (water), DMSO solvent control group, positive controls (ametycin) and 8 variable concentrations (0.1,0.3,0.9,2.7,8.1,24.3 μ gmL are established in experiment -1) testing sample, IC 50value < 0.1 μ gmL -1testing sample continue down to dilute, then establish 6 variable concentrations (0.0003,0.001,0.004,0.011,0.033 and 0.100 μ gmL -1), each concentration establish 3 parallel.Collect exponential phase cell, blood counting chamber counts, and is inoculated in the 96 flat Tissue Culture Plates in hole, is placed in 5%CO by 4500, every hole cancerous cell amount 2, cultivate in humidity more than 90%, 37 DEG C of incubators.Take out after 24h and add a certain amount of testing sample, take out after continuing to cultivate 72h and be placed in the every porocyte form of basis of microscopic observation, record cellular morphology situation of change, then every hole adds MTT solution (being dissolved in balanced salt solution PBS) the 15 μ L of 5mg/mL, after 37 DEG C of reaction 4h, by cell culture fluid sucking-off, every hole adds 100 μ L DMSO and is fully dissolved by Formazane, Tissue Culture Plate is placed in MK3 microplate reader, survey the absorbance (A) in each hole with 570nm wavelength, ask growth inhibition ratio by following formula.
Be abscissa with sample concentration, take suppression ratio as vertical coordinate, utilize origin software to simulate suppression ratio curve chart according to Concentraton gradient, the sample concentration when suppression ratio is 50% is the IC of cytotoxic activity 50value, sample activity result is namely with half-inhibition concentration (IC 50) represent.
As can be seen from Table 2, the structural difference of cardiac glycoside compound 12 β-hydroxycalotropin and calotropin and then anti-tumor activity also also exist significant difference.Cardiac glycoside compound anti-tumor activity of the present invention is obviously strong than calotropin.
The external tumor suppression result of table 2 cardiac glycoside compound 12 β-hydroxycalotropin
Embodiment 5
Cardiac glycoside compound 12 β-hydroxycalotropin 8g embodiment 1 prepared mixes with microcrystalline Cellulose 75g and magnesium stearate 7g, and mixture single punch tablet machine breaks into diameter 5mm, the tablet of weight 100mg.In this tablet, every sheet is containing 12 β-hydroxycalotropin 8mg.In conjunction with disease, each 1-2 sheet, daily 2-3 time.
Embodiment 6
Cardiac glycoside compound 12 β-hydroxycalotropin 20g embodiment 1 prepared mixes with lactose 95g and magnesium stearate 6g, with every 300mg filled capsules.In this capsule, each capsule is containing 12 β-hydroxycalotropin 25mg.In conjunction with disease, each 1-2, daily 3-4 time.
The specific embodiment more than enumerated is the explanation carried out the present invention.It is pointed out that above embodiment is only for the invention will be further described, do not represent protection scope of the present invention, the nonessential amendment that other people prompting according to the present invention is made and adjustment, still belong to protection scope of the present invention.

Claims (5)

1. cardiac glycoside compound 12 β-hydroxycalotropin is preparing the purposes in the medicine with treatment and prophylaxis of tumours effect, and the molecular formula of described cardiac glycoside compound 12 β-hydroxycalotropin is C 29h 40o 10, structural formula is as follows:
Described tumor is oral cancer, pulmonary carcinoma or Human Prostate Cancer Cells LNCap.
2. cardiac glycoside compound 12 β-hydroxycalotropin according to claim 1 is preparing the purposes in the medicine with treatment and prophylaxis of tumours effect, it is characterized in that: the preparation method of described cardiac glycoside compound 12 β-hydroxycalotropin is as follows:
A, choose Radix Calotropis giganteae stem, after pulverizing, add ethanol, lixiviate 3 ~ 4 times, each 6 ~ 8 days, merge lixiviating solution, be evaporated to the ethanol extraction obtaining Radix Calotropis giganteae without alcohol taste;
B, the ethanol extraction of Radix Calotropis giganteae is scattered in water and makes Radix Calotropis giganteae suspension, be 1:3,1:2 and 1:1 by the volume ratio of Radix Calotropis giganteae suspension and petroleum ether respectively, with petroleum ether to after Radix Calotropis giganteae suspension re-extract, retain the aqueous phase after petroleum ether extraction;
C, filtered by the aqueous phase after petroleum ether extraction, filtrate be separated with D-101 macroporous adsorbent resin column chromatography, and use water and methanol-eluted fractions successively, collect meoh eluate, concentrating under reduced pressure obtains methanol extract after reclaiming methanol;
D, by methanol extract through decompression silica gel column chromatography, be respectively 100:1,50:1,25:1,10:1,5:1,2:1 and 0:100 as eluant using the volume ratio of chloroform and methanol, gradient elution carried out to decompression silicagel column, respectively must crude extract Fr.1 ~ Fr.7;
E, by step D gained crude extract Fr.4 through silica gel column chromatography, be respectively 10:1,8:1,6:1,4:1,2:1,0:1 as eluant using the volume ratio of chloroform and methanol, gradient elution carried out to silicagel column, obtain 6 part Fr.4-1 ~ Fr.4-6;
F, by the Fr.4-2 of E step through silica gel column chromatography, adopt chloroform and acetone to carry out eluting as eluant, adopt TLC thin layer chromatography to collect identical composition during eluting, obtain 6 part Fr.4-2-1 ~ Fr.4-2-6; Fr.4-2-3 is carried out successively Sephadex LH-20 gel filtration chromatography, reversed phase column chromatography and silica gel column chromatography again, finally obtain cardiac glycoside compound 12 β-hydroxycalotropin.
3. cardiac glycoside compound 12 β-hydroxycalotropin according to claim 1 is preparing the purposes in the medicine with treatment and prophylaxis of tumours effect, it is characterized in that: in steps A, the mass volume ratio of Radix Calotropis giganteae stem and ethanol is 1kg:1 ~ 3L; The volumn concentration of described ethanol is 92 ~ 98%.
4. cardiac glycoside compound 12 β-hydroxycalotropin according to claim 1 is preparing the purposes in the medicine with treatment and prophylaxis of tumours effect, it is characterized in that: in step B with petroleum ether to after Radix Calotropis giganteae suspension re-extract 3 times, retain the aqueous phase after petroleum ether extraction.
5. cardiac glycoside compound 12 β-hydroxycalotropin according to claim 1 is preparing the purposes in the medicine with treatment and prophylaxis of tumours effect, it is characterized in that: in step F, the volume ratio of chloroform and acetone is 4:5; The gel column adopted during gel filtration chromatography is Sephadex LH-20 gel column, and during gel filtration chromatography, eluting solvent adopts volumn concentration to be the ethanol of 95%; The chloroform of the eluting solvent again adopted during silica gel column chromatography to be volume ratio be 11:1:1, methanol and acetone mixed solvent.
CN201410662253.5A 2013-04-11 2013-04-11 Application of cardiac glycoside compound 12beta-hydroxycalotropin Active CN104398532B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410662253.5A CN104398532B (en) 2013-04-11 2013-04-11 Application of cardiac glycoside compound 12beta-hydroxycalotropin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201410662253.5A CN104398532B (en) 2013-04-11 2013-04-11 Application of cardiac glycoside compound 12beta-hydroxycalotropin
CN201310124216.4A CN103191143B (en) 2013-04-11 2013-04-11 New application of cardiac glycoside compound

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CN201310124216.4A Division CN103191143B (en) 2013-04-11 2013-04-11 New application of cardiac glycoside compound

Publications (2)

Publication Number Publication Date
CN104398532A true CN104398532A (en) 2015-03-11
CN104398532B CN104398532B (en) 2017-02-22

Family

ID=52636241

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410662253.5A Active CN104398532B (en) 2013-04-11 2013-04-11 Application of cardiac glycoside compound 12beta-hydroxycalotropin

Country Status (1)

Country Link
CN (1) CN104398532B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114349722A (en) * 2022-01-24 2022-04-15 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) Cardiac glycoside compound and preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1711099A (en) * 2002-10-09 2005-12-21 优尼拜尔斯金股份有限公司 Extract with anti-tumor and anti-poisonous activity
CN101156865A (en) * 2007-10-26 2008-04-09 中国热带农业科学院热带生物技术研究所 Antineoplastic new usage of cardiac glycoside compound in antiar

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1711099A (en) * 2002-10-09 2005-12-21 优尼拜尔斯金股份有限公司 Extract with anti-tumor and anti-poisonous activity
CN101156865A (en) * 2007-10-26 2008-04-09 中国热带农业科学院热带生物技术研究所 Antineoplastic new usage of cardiac glycoside compound in antiar

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JUN-ZHU LI,等: "Cytotoxicity of cardenolides and cardenolide glycosides from Asclepias curassavica", 《BIOORGANIC ＆ MEDICINAL CHEMISTRY LETTERS》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114349722A (en) * 2022-01-24 2022-04-15 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) Cardiac glycoside compound and preparation method and application thereof
CN114349722B (en) * 2022-01-24 2023-04-14 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) Cardiac glycoside compound and preparation method and application thereof

Also Published As

Publication number Publication date
CN104398532B (en) 2017-02-22

Similar Documents

Publication Publication Date Title
CN103130644B (en) Method of obtaining and separating rosmarinic acid, apigenin and luteolin from elsholtzia haichowensis
CN113307785B (en) Abietane diterpenoid compound with anti-tumor effect, preparation method, pharmaceutical composition and application
CN108003214A (en) A kind of saponin compound and its methods and applications extracted from the rhizoma bolbostemmae
CN104817432A (en) Anti-tumor drug of diterpenoid compound, and preparation method and application thereof
CN111184713A (en) Application of eudesmane type sesquiterpene lactone epimer in preparation of anti-breast cancer medicine
CN103191143B (en) New application of cardiac glycoside compound
CN104873570B (en) A kind of method for extraction and purification of Prunella vulgaris general flavone and its application
CN102000066B (en) Inula helianthus-aquatica extract, anti-tumor medicament using same as active ingredient, preparation method and application thereof
CN101880306B (en) Stauntonia brachyanthera Hand-Mazz saponins components as well as preparation method and application thereof
CN101028322B (en) Use of Maoliefengdou extract for preparing anti-cancer medicine
CN105712963B (en) A kind of coumarin dimer and its preparation method and application
CN104398532B (en) Application of cardiac glycoside compound 12beta-hydroxycalotropin
CN104857245A (en) Preparation method and application of total saponins from flos hosta ventricosa
CN104324043A (en) Use of cardiac glycoside compound
CN109456163B (en) Cycloalkenone compound with symmetrical structure and preparation method and application thereof
CN109091602B (en) Effective component of semen allii tuberosi, extraction method and application thereof in preparing liver injury protection medicine
CN101537027A (en) Extract with anti-lung cancer activity of streptocaulon juventas (Loureiro) Merrill and preparation process of compounds thereof
CN111499605B (en) Isopentene chromone compound and preparation method and application thereof
CN107880084A (en) The method that middle extraction preparation high-purity acteoside is spent from platymiscium of reaching the clouds
CN107213176B (en) Hydrangea macrophylla leaf extract, and pharmaceutical composition, preparation method and application thereof
CN105037470A (en) Novel triterpenoid compound, preparation method and medical application thereof
CN104788291A (en) Antitumor drug prepared from diterpenoid compound isolated from Chinese azalea flower, method and use
CN109705183A (en) Smelly seven secondary metabolites and its pharmaceutical composition and preparation method and its application
CN107936001A (en) 8 C β D xylosides of apiolin and its preparation method and application
CN109180632A (en) A kind of noval chemical compound isolated from tripterygium wilfordii and preparation method thereof and medical usage

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant