CN102000097B - Bunge auriculate root C21 total steroidal glycoside degradation product and antitumor effect thereof - Google Patents
Bunge auriculate root C21 total steroidal glycoside degradation product and antitumor effect thereof Download PDFInfo
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- CN102000097B CN102000097B CN201010505530A CN201010505530A CN102000097B CN 102000097 B CN102000097 B CN 102000097B CN 201010505530 A CN201010505530 A CN 201010505530A CN 201010505530 A CN201010505530 A CN 201010505530A CN 102000097 B CN102000097 B CN 102000097B
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Abstract
The invention relates to the field of natural medicines, in particular to a bunge auriculate root C21 total steroidal glycoside degradation product, which is characterized by being prepared by the following steps of: degrading dry powder of the C21 total steroidal glycoside of bunge auriculate root in the presence of acid or alkali, regulating the PH to be 7, extracting by using an organic solvent, and recovering the organic solvent. The bunge auriculate root C21 total steroidal glycoside degradation product has strong antitumor effect.
Description
Technical field
The present invention relates to natural medicine field, be specifically related to a kind of Radix Cynanchi Auriculati C
21Steroid total glycosides catabolite, and in the application of anti-tumor aspect.
Background technology
Radix Cynanchi Auriculati is one of motherland's Chinese medicine, and the medicine source is mainly from the tuber of asclepiadaceae Cynanchum plant cynanchum auriculatum Royle (Cynanchum auriculatum), mountain on the other way round cynanchum auriculatum Royle ex Wight (C.wifordii) and Bunge Swallowwort Root (C.bungei).Radix Cynanchi Auriculati is considered as the anti-old treasure of health preserving in history as tonification Chinese medicine by ancient Chinese medicine doctor, effects such as the liver benefiting that nourishes blood, the benefit of reinforcing the kidney essence, strengthening the tendons and bones, pitch-black beard and hair and life lengthening.
C
21Sterioside is that a class aglycon is the chemical compound that derivatives of pregnane and 2-desoxy sugar etc. form, and is the main medicinal ingredient in the Radix Cynanchi Auriculati, also is to find a more compounds in the Radix Cynanchi Auriculati.Radix Cynanchi Auriculati C
21The sterioside aglycon mainly contains to accuse and reaches booth, kidjolanin, Herba seu radix metaplexis aglycon and Jia Jiaming etc., and its mixture abbreviates C as
21Steroid total glycosides, sugar mostly are 2 greatly, and the 6-desoxy sugar as 2-desoxy-D-altromethylose, 2-deoxidation 3-methyl-D-fucose., oleandrose, cymarose, much is connected with glucose endways.All link to each other with 1 → 4 glycosidic bond between the sugar, sugar chain 1-7 is not waited.Inventor's early-stage Study shows that Caudatin .-3-O-β-D-Apocynum cannabinum glucosides has stronger anti-tumor activity, especially hepatocarcinoma is had very strong inhibition effect (seeing Chinese patent ZL200710020032.8).Although monomeric pharmacological effect is good, because its extracting method more complicated, yield is low, has therefore limited it and has applied.
Summary of the invention
The invention discloses a kind of Radix Cynanchi Auriculati C
21The catabolite of steroid total glycosides, it has excellent anti-tumor activity, and preparation method is simple, is fit to industrialized great production.
The present invention is with Radix Cynanchi Auriculati C
21The steroid total glycosides adds acid or alkali is degraded, and PH=7 is regulated in the degraded back, uses organic solvent extraction, reclaims organic solvent and promptly gets Radix Cynanchi Auriculati C
21Steroid total glycosides catabolite.The preferred glacial acetic acid of acid that is used for degrading or alkali, hydrochloric acid or sodium hydroxide.More preferably glacial acetic acid.When using glacial acetic acid or salt acid degradation, its concentration is preferred 0.1%～10%, is weight percentage, and the percentage ratio among the present invention all is weight percentage.When using the sodium hydroxide degraded, its concentration preferred 5%～10%.
Preferred chloroform of the organic solvent that is used to extract or ethyl acetate.With preferred further washing and dehydration behind the organic solvent extraction.
Preferred 60 ℃～100 ℃ of the temperature of degraded.
Preferred 2～6 hours of degradation time.
Radix Cynanchi Auriculati C of the present invention
21Steroid total glycosides chemical degradation product comprises: kidjolanin-3-O-β-D-digoxigenin glucosides, kidjolanin-3-O-α-L-diginose-(1 → 4)-β-D-Apocynum cannabinum glucosides, Caudatin .-3-O-β-D-Apocynum cannabinum glucosides and Caudatin. etc., its part chemical structural formula is as follows, wherein R, R
1Be sugar chain:
Radix Cynanchi Auriculati C
21The preparation of steroid total glycosides can be referring to literature method, also available embodiment 1 method preparation.
Chemical degradation product of the present invention has following advantage:
1, the anti-tumor in vivo activity is stronger.The Radix Cynanchi Auriculati C of the present invention's preparation
21The catabolite of steroid total glycosides is in animal body in the antitumor test, compared to Radix Cynanchi Auriculati C
21The steroid total glycosides has more obvious inhibitory action to mice transplanted tumor H22 liver-cancer solid tumor and Lewis lung cancer solid tumor.The drug effect of acetolysis product is the strongest.
2, content of effective is higher.Radix Cynanchi Auriculati C among the present invention
21Caudatin. in the steroid total glycosides-3-O-β-D-Apocynum cannabinum glucosides, Caudatin. aglycon, kidjolanin-3-O-β-D-digoxigenin glucosides and kidjolanin-3-O-α-L-diginose-(1 → 4)-β-D-Apocynum cannabinum glucosides account for total mass ratio 5.53%.By restricted degraded Radix Cynanchi Auriculati C
21The steroid total glycosides, the degradation of long sugar chain in a large number become aglycon or contain the chemical compound of 1-2 saccharide residue, thereby make the content of kidjolanin-3-O-β-D-digoxigenin glucosides in the Radix Cynanchi Auriculati, kidjolanin-3-O-α-L-diginose-(1 → 4)-β-D-Apocynum cannabinum glucosides, Caudatin. aglycon and Caudatin .-3-O-β-D-Apocynum cannabinum glucosides increase.Containing active component, to account for total mass ratio be 10%～55%.
Be part pharmacological experiment and result below.
(1) Radix Cynanchi Auriculati C
21Steroid total glycosides and Radix Cynanchi Auriculati C
21The acetic acid catabolite of steroid total glycosides is tested mice H22 solid tumor anti-tumor in vivo
Get the mice transplanted tumor H22 ascites of growth 8d under aseptic condition, by 3: 1 dilution proportion, it was subcutaneous to be inoculated in healthy mice right fore axillary fossa, every 0.2mL with physiological saline solution.Inoculation random packet next day, 10 every group.If lotus tumor matched group, the variable concentrations dosage group of the acetic acid catabolite of radix cynanchi bungei total glucoside, radix cynanchi bungei total glucoside and the sodium hydroxide catabolite of radix cynanchi bungei total glucoside, cyclophosphamide (CTX) group.Inoculation rises next day, radix cynanchi bungei total glucoside group, radix cynanchi bungei total glucoside acetic acid catabolite group, radix cynanchi bungei total glucoside sodium hydroxide catabolite group intraperitoneal injection every day 1 time, and logotype 10 days, CTX organizes in the 4th day intraperitoneal injection of inoculation.Lotus tumor matched group lumbar injection is with the distilled water of volume.Drug withdrawal animal next day is weighed, and strips tumor tissue after the execution, claims tumor heavy.Be calculated as follows inhibition rate of tumor growth.
Tumour inhibiting rate=(the average tumor of the average tumor weight/matched group of 1-experimental group is heavy) * 100%.
This test is carried out three batches altogether.The results are shown in Table 1.The gained data represent with mean+SD, and with the t method of inspection significant difference between each group relatively.
Acetic acid/sodium hydroxide hydrolysis the product of table 1. Radix Cynanchi Auriculati C21 steroid total glycosides is to the inhibitory action of murine sarcoma H22
Annotate: compare with lotus tumor matched group,
*P＜0.01
By table 1 as seen, catabolite tumour inhibiting rate of the present invention is apparently higher than radix cynanchi bungei total glucoside, and wherein the catabolite effect of acetic acid is better than the drug effect of the catabolite of sodium hydroxide again.
(2) Radix Cynanchi Auriculati C
21Steroid total glycosides and Radix Cynanchi Auriculati C
21The chemical degradation product of steroid total glycosides is tested Mice Bearing Lewis solid tumor anti-tumor in vivo
Get the C57BL/6 tumor-bearing mice of inoculation Lewis lung cancer 14d, taking off cervical vertebra puts to death, get tumor tissue under the aseptic condition, add normal saline (1: 3) with glass homogenizer and grind into cell suspension, getting 0.2ml/, only to be inoculated in the right axillary fossa of C57BL/6 healthy mice subcutaneous, after the inoculation with the animal random packet, every group 10, be respectively the variable concentrations dosage group of lotus tumor matched group, radix cynanchi bungei total glucoside group, radix cynanchi bungei total glucoside acetic acid catabolite group, radix cynanchi bungei total glucoside sodium hydroxide catabolite group, cyclophosphamide (CTX) group.Inoculation rises next day, radix cynanchi bungei total glucoside group, radix cynanchi bungei total glucoside acetic acid catabolite group, radix cynanchi bungei total glucoside sodium hydroxide catabolite group intraperitoneal injection every day 1 time, logotype 12 days, the CTX group adopts the interruption method to be administered three times, respectively at administration in the 1st, 5,9 day behind the inoculated tumour.Lotus tumor matched group lumbar injection is with the distilled water of volume.Drug withdrawal animal next day is weighed, and strips tumor tissue after the execution, claims tumor heavy.Be calculated as follows inhibition rate of tumor growth.Tumour inhibiting rate=(the average tumor of the average tumor weight/matched group of 1-experimental group is heavy) * 100%.
This test is carried out three batches altogether.The results are shown in Table 2.The gained data represent with mean+SD, and with the t method of inspection significant difference between each group relatively.
Acetic acid/sodium hydroxide hydrolysis the product of table 2. Radix Cynanchi Auriculati C21 steroid total glycosides is to the inhibitory action of Lewis solid tumor
Annotate: compare with lotus tumor matched group,
*P＜0.001
By table 2 as seen, catabolite tumour inhibiting rate of the present invention is apparently higher than radix cynanchi bungei total glucoside, and wherein the catabolite effect of acetic acid is better than the drug effect of the catabolite of sodium hydroxide again.
(3) Radix Cynanchi Auriculati C
21Steroid total glycosides and Radix Cynanchi Auriculati C
21The acute toxicity test of steroid total glycosides acetic acid catabolite
Get 120 of mices, 10 every group, the medicine of various dose is given in the abdominal cavity, observes continuously 7 days, counts dead mice.Calculate LD50, result of the test sees Table 3.
Table 3 The acute toxicity tests
By table 3 as seen, the toxicity of catabolite of the present invention is less than the toxicity of its total glycosides.
Description of drawings
Fig. 1 is the HPLC figure of reference substance solution
Fig. 2 is Radix Cynanchi Auriculati C
21Steroid total glycosides HPLC figure
Fig. 3 is Radix Cynanchi Auriculati C of the present invention
21Steroid total glycosides acetic acid catabolite HPLC figure
The specific embodiment
Radix Cynanchi Auriculati C among the present invention
21The assay of steroid total glycosides chemical degradation product, content with active component Caudatin .-3-O-β-D-Apocynum cannabinum glucosides, Caudatin., kidjolanin-3-O-β-D-digoxigenin glucosides and kidjolanin-3-O-α-L-diginose-(1 → 4)-β-D-Apocynum cannabinum glucosides is testing index, adopt high performance liquid chromatography (HPLC) to measure, adopt external standard method quantitative.Adopt Waters2695 liquid-phase chromatographic analysis system, analysis condition is as follows: LichrospherC18 chromatographic column (250mm * 4.6mm, 5 μ m); Adopt gradient elution, flow velocity 1.0mL/min; Column temperature is 25 ℃; Detect wavelength 223nm.
The HPLC method is measured Radix Cynanchi Auriculati C
21The eluent gradient of steroidal glycoside sees Table 4
Table 4. eluent gradient
Radix Cynanchi Auriculati C
21Steroid total glycosides preparation method
Get Radix Cynanchi Auriculati crude drug decoction pieces 10kg, with 95% alcohol reflux of 7 times of volumes 3 times, each 2h merges three extracting solution decompression recycling ethanols to there not being the alcohol flavor, gets 1.0 kilograms of alcohol-extracted extracts.Get alcohol-extracted extract and add an amount of aqueous dispersion for 1.0 kilograms, use petroleum ether successively, chloroform, each 2.0L extraction of n-butyl alcohol 3 times merges extract respectively 3 times, reclaims organic solvent, obtains petroleum ether, chloroform, n-butanol portion respectively.Get D101 macroporous adsorptive resins on the n-butanol portion, water and 95% ethanol elution are collected ethanol elution successively, and decompression recycling ethanol gets n-butyl alcohol macroporous resin column absorb-elute part.Get chloroform extract and n-butyl alcohol macroporous resin column absorb-elute partly merges, promptly get Radix Cynanchi Auriculati C
21Steroidal total glycosides 250g.
The preparation method of radix cynanchi bungei total glucoside acetic acid catabolite
Get Radix Cynanchi Auriculati C
21Steroid total glycosides powder 1g, the accurate title, decide, and adds 5% acetum 50mL, put in 100 ℃ of water-baths, reflux 5h takes out, cooling, the sodium hydroxide solution with 10% is regulated PH=7, uses chloroform extraction 3 times, each 50mL, extract merges, and washes with water twice, each 100mL abandons water lotion, the extract anhydrous sodium sulfate dehydration, reclaim the acetic acid catabolite 250mg that chloroform gets Radix Cynanchi Auriculati C21 steroid total glycosides, wherein to account for total mass ratio be 41% to four kinds of active component.
The preparation method of radix cynanchi bungei total glucoside sodium hydroxide catabolite
Get Radix Cynanchi Auriculati C
21Steroid total glycosides powder 1g, the accurate title, decide, and adds 10% sodium hydroxide solution 50mL, put in 100 ℃ of water-baths, reflux 4h takes out, cooling, the hydrochloric acid solution with 10% is regulated PH=7, uses chloroform extraction 3 times, each 50mL, extract merges, and washes with water twice, each 100mL abandons water lotion, the extract anhydrous sodium sulfate dehydration, reclaim the sodium hydroxide catabolite 100mg that chloroform gets Radix Cynanchi Auriculati C21 steroid total glycosides, wherein to account for total mass ratio be 11% to four kinds of active component.
Claims (5)
1. Radix Cynanchi Auriculati C
21Steroid total glycosides catabolite is characterized in that by following method preparation: with Radix Cynanchi Auriculati C
21Steroid total glycosides dried powder adds in the degradation solution degrades, pH=7 is regulated in the degraded back, use organic solvent extraction, reclaim organic solvent promptly, wherein degradation solution is glacial acetic acid, hydrochloric acid or sodium hydroxide, and the concentration of glacial acetic acid or hydrochloric acid is 0.1%～10%, concentration sodium hydroxide is 5%～10%, all be weight percentage, organic solvent is chloroform or ethyl acetate, and the temperature of degraded is 60 ℃～100 ℃.
2. the catabolite of claim 1, wherein degradation solution is a glacial acetic acid.
3. the catabolite of claim 1, wherein degradation time is 2～6 hours.
4. the catabolite of claim 1 is wherein washed and dehydration with also comprising behind the organic solvent extraction.
5. the catabolite of claim 1 is used to prepare the purposes of antitumor drug.
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| CN103585216A (en) * | 2013-12-04 | 2014-02-19 | 江南大学 | Use of C21 steroidal glycoside of root tubers of Cynanchun auriculatum Royle ex Wight, Cynanchum bungei Decne and Cynanchum wifordii Hemsl in activation of tyrosinase |
| CN112588318B (en) * | 2020-12-15 | 2022-02-15 | 江南大学 | Green and efficient preparation method of short-sugar-chain C21 steroid glycoside of radix cynanchi bungei |
| CN113912662A (en) * | 2021-11-02 | 2022-01-11 | 盐城师范学院 | C in fermentation liquor21Method for purifying steroid compound |
| CN113817614B (en) * | 2021-11-02 | 2023-06-27 | 盐城师范学院 | High-efficiency synthesis C 21 Alternaria alternata Z-44 of steroid glycoside and application thereof |
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