CN100406465C - Anthraquinone glycoside compounds containing glucopyranoside group and use thereof - Google Patents
Anthraquinone glycoside compounds containing glucopyranoside group and use thereof Download PDFInfo
- Publication number
- CN100406465C CN100406465C CNB2005100189917A CN200510018991A CN100406465C CN 100406465 C CN100406465 C CN 100406465C CN B2005100189917 A CNB2005100189917 A CN B2005100189917A CN 200510018991 A CN200510018991 A CN 200510018991A CN 100406465 C CN100406465 C CN 100406465C
- Authority
- CN
- China
- Prior art keywords
- anthraquinone
- glucopyranoside
- silica gel
- column chromatography
- present
- 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.)
- Expired - Fee Related
Links
Abstract
The present invention relates to novel anthraquinone glycoside compounds containing glucopyranoside groups, and a usage of the anthraquinone glycoside compounds containing glucopyranoside groups. The compounds of the present invention are substances with the molecular formula of 1-methoxyl-2-methoxylmethyl-3-hydroxyl-9, 10-anthraquinone-3-O-beta-D-glucopyranoside. The compounds can be extracted from lasianthus acuminatissimus by adopting various separation methods including a macroporous resin column chromatography, a silicon gel column chromatography, etc., and one kind of anthraquinone monomer ingredients is obtained; the structure of the anthraquinone monomer is identified by a spectral analysis and physicochemical method, and is first separated new compounds in the nature world. The bioactivity test of the present invention shows that the present invention has strong action on preventing ovarian cancer. The inhibiting rate of the present invention to human ovary cancer OVCAR-2780 cells is 50.8%, and IC50 is 1 ug/ml (p is smaller than 0.05).
Description
Technical field
The present invention relates to a kind of new anthraquinone glycoside compound of glucopyranoside group and uses thereof that contains.
Background technology
The anthraquinone glycoside compound that contains glucopyranoside group that the present invention relates to is looked into newly through the CA retrieval, is the isolating first new compound of nature.
Summary of the invention
The object of the present invention is to provide a kind of new anthraquinone glycoside compound of glucopyranoside group and uses thereof that contains.
This anthraquinone glycoside compound that contains glucopyranoside group has the effect of stronger ovarian cancer resistance.
Technical scheme of the present invention is:
The anthraquinone glycoside compound that contains glucopyranoside group, its molecular formula is: 1-methoxyl group-2-methoxymethyl-9,10-anthraquinone-3-O-β-D-glucopyranoside, chemical structural formula following (I).
This compound is English by name: 1-methoxy-2-methoxymethyl-9,10-anthraquinone-3-O-β-D-glucopyranos ide.We are long-tail Root of Chinese Lasianthus glycosides B (I, Lasianthuoside B) with its name life again this new compound.
The ethanol of at first using 5 times of long-tail Root of Chinese Lasianthus (Lasianthus acuminatissimus Merr) medicinal material weight was with medicinal material refluxing extraction 3 times, each 1 hour; Centrifugal or the filtration with extracting solution then, it is 0.5g crude drug/ml that filtrate is evaporated to concentration at 55 ℃, refilters, and gets supernatant liquor; Supernatant liquor is joined on the macroporous adsorptive resins of handling well, water, 50% ethanol gradient elution is collected 50% ethanol eluate, is evaporated to driedly, obtains anthraquinone glycoside compound and be main extract 37.5 grams; Get the extract dissolve with ethanol, admix the silica gel of 3 times of amounts, separate with silica gel chromatographic column dry back, and the isolating eluting solvent of silica gel chromatographic column is 50: 50 a chloroform of volume ratio: methyl alcohol mixed liquor, elution flow rate are 500 milliliters/hour; Separate with gel column chromatography, the isolating eluting solvent of gel column chromatography is 60: 40 a methyl alcohol of volume ratio: water mixed liquid, elution flow rate are 60 milliliters/hour again; Thin-layer chromatography is checked, merges same section; Carry out a silica gel column chromatography again and separate, the isolating eluting solvent of silica gel chromatographic column is 50: 50 a chloroform of volume ratio: methyl alcohol mixed liquor, elution flow rate are 300 milliliters/hour; Promptly make the name life and be the anthraquinone glycoside compound that contains glucopyranoside group of long-tail Root of Chinese Lasianthus glycosides B.
The present invention utilizes multiple separation means, comprise macroporous resin column chromatography, silica gel column chromatography, reversed-phase silica gel column chromatography, Sephadex column chromatography and preparation type high performance liquid phase column chromatography etc. have been furtherd investigate the chemical ingredients in the medicinal material rhizome, therefrom separate and obtain a kind of anthraquinone monomer component, utilize spectroscopic analysis and physico-chemical process to identify its structure, and look into newly, prove the isolating first new compound of nature through the CA retrieval.
Biological activity test shows that long-tail Root of Chinese Lasianthus glycosides B has the effect of stronger ovarian cancer resistance.It is 50.8% to human ovarian cancer OVCAR-2780 cell inhibiting rate, IC
50Be 1ug/ml, (P＜0.05) has shown the biological activity of ovarian cancer resistance.
The invention has the advantages that: separate the new compound that has obtained new effect with ovarian cancer resistance.
Its physico-chemical property and various wave spectrum feature are as follows:
This compound is yellow needle crystal, fusing point: 224-226 ℃, easily is dissolved in organic solvents such as methyl alcohol, dimethyl sulfoxide (DMSO), pyridine.
UVmax(MeOH)nm(logε)：207.2(3.96)，265.8(4.06)，331.6(3.06)，358.0(2.99).
IRmax(KBr)cm
-1：3435(OH，br)，1674(C＝O)，1599，1539，(Ar)，1385，1282，1080，1043.
HRFAB-MS (m/z) is (%): 461.1427[M+H]
+(calculated value is 461.1447, and molecular formula is C
23H
25O
10).
ESI-MSm/z(％)：483[M+Na]
+(100)，469[M+Na-CH
2]
+(4)，455[M+Na-2CH
2]
+(1)，320[M+Na-1-glc]
+(8).
1HNMR(DMSO-d
6，500MHz)δ：
(8.14-8.19 2H, m, H-5,8), 7.87-7.94 (2H, m, H-6,7), 7.75 (1H, s, H-4), 5.07 (1H, d, J=5.5Hz, H-1 '), 4.53,4.63 (each 1H, d, J=10.0Hz, AB systems, H-11), 3.89 (3H, s, MeO), 3.29 (3H, s, MeO), 3.25-3.70 (m, proton on the glucose).
13C-NMR(DMSO-d
6，125MHz)：
161.60(C-1)，128.48(C-2)，162.23(C-3)，109.34(C-4)，136.94(C-4a)，126.96(C-5)，134.41(C-6)，135.44(C-7)，127.46(C-8)，135.10(C-8a)，181.05(C-9)，120.35(C-9a)，182.79(C-10)，132.75(C-10a)，63.49(C-11)，62.66(OMe
1)，58.63(OMe
2)，101.38(C-1’)，73.96(C-2’)，77.01(C-3’)，70.07(C-4’)，78.08(C-5’)，61.13(C-6’).
DEPT, HMQC and HMBC result are as shown in table 1.
Nmr spectrum data (the DMSO-d of table 1 long-tail Root of Chinese Lasianthus glycosides B (Lasianthuoside B)
6)
The anti-human ovarian carcinoma active testing:
Adopt mtt assay, measure long-tail Root of Chinese Lasianthus glycosides B (I) human ovarian cancer OVCAR-2780 cell inhibiting rate and IC
50Value.Get 96 hole flat boards, every hole adds OVCAR-2780 cell suspension 100ul, and flat board is put 37 ℃ of CO
2(5%) incubator is 24 hours, experimental group adds is tried anthraquinone monomer (with the RPMI-1640 dilution), control group adds isopyknic RPMI-1640, flat board is put and is hatched 48 hours in the incubator, hatched 4 hours after adding 0.5%MTT liquid in every hole again, and the sucking-off supernatant liquor adds the DMSO dissolving, shake up with dull and stereotyped shaking table, measure the optical density(OD) OD of each aperture with the dull and stereotyped reader of automatization spectrophotometric at 550nm rice.
Cell survival rate=(dosing cell OD/ control cells OD) * 100
Long-tail Root of Chinese Lasianthus glycosides B (I) is to human ovarian cancer OVCAR-2780 cell inhibiting rate and IC
50Value sees Table 2.
The inhibiting rate and the IC to OVCAR-2780 of table 2 long-tail Root of Chinese Lasianthus glycosides
50Value
Embodiment
Embodiment 1
The ethanol of at first using 5 times of long-tail Root of Chinese Lasianthus (Lasianthus acuminatissimus Merr) medicinal material weight was with medicinal material refluxing extraction 3 times, each 1 hour; Centrifugal or the filtration with extracting solution then, it is 0.5g crude drug/ml that filtrate is evaporated to concentration at 55 ℃, refilters, and gets supernatant liquor; Supernatant liquor is joined on the macroporous adsorptive resins of handling well, water, 50% ethanol gradient elution is collected 50% ethanol eluate, is evaporated to driedly, obtains anthraquinone glycoside compound and be main extract 37.5 grams; Get the extract dissolve with ethanol, admix the silica gel of 3 times of amounts, separate with silica gel chromatographic column dry back, and the isolating eluting solvent of silica gel chromatographic column is 50: 50 a chloroform of volume ratio: methyl alcohol mixed liquor, elution flow rate are 500 milliliters/hour; Separate with gel column chromatography, the isolating eluting solvent of gel column chromatography is 60: 40 a methyl alcohol of volume ratio: water mixed liquid, elution flow rate are 60 milliliters/hour again; Thin-layer chromatography is checked, merges same section; Carry out a silica gel column chromatography again and separate, the isolating eluting solvent of silica gel chromatographic column is 50: 50 a chloroform of volume ratio: methyl alcohol mixed liquor, elution flow rate are 300 milliliters/hour; Promptly make the anthraquinone glycoside compound that contains glucopyranoside group.
This contains the anthraquinone glycoside compound chemical structural formula following (I) of glucopyranoside group.
Claims (2)
1. anthraquinone glycoside compound that contains glucopyranoside group is characterized in that its molecular formula is: 1-methoxyl group-2-methoxymethyl-9, and 10-anthraquinone-3-0-β-D-glucopyranoside, chemical structural formula following (I):
2. the preparation method who contains the anthraquinone glycoside compound of glucopyranoside group according to claim 1, the ethanol that it is characterized in that at first using 5 times of long-tail Root of Chinese Lasianthus medicinal material weight was with medicinal material refluxing extraction 3 times, each 1 hour; Centrifugal or the filtration with extracting solution then, it is 0.5g crude drug/ml that filtrate is evaporated to concentration at 55 ℃, refilters, and gets supernatant liquor; Supernatant liquor is joined on the macroporous adsorptive resins of handling well, water, 50% ethanol gradient elution is collected 50% ethanol eluate, is evaporated to driedly, obtains anthraquinone glycoside compound and be main extract; Get the extract dissolve with ethanol, admix the silica gel of 3 times of amounts, separate with silica gel chromatographic column dry back, and the isolating eluting solvent of silica gel chromatographic column is 50: 50 a chloroform of volume ratio: methyl alcohol mixed liquor, elution flow rate are 500 milliliters/hour; Separate with gel column chromatography, the isolating eluting solvent of gel column chromatography is 60: 40 a methyl alcohol of volume ratio: water mixed liquid, elution flow rate are 60 milliliters/hour again; Thin-layer chromatography is checked, merges same section; Carry out a silica gel column chromatography again and separate, the isolating eluting solvent of silica gel chromatographic column is 50: 50 a chloroform of volume ratio: methyl alcohol mixed liquor, elution flow rate are 300 milliliters/hour; Promptly make the anthraquinone glycoside compound that contains glucopyranoside group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100189917A CN100406465C (en) | 2005-06-24 | 2005-06-24 | Anthraquinone glycoside compounds containing glucopyranoside group and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100189917A CN100406465C (en) | 2005-06-24 | 2005-06-24 | Anthraquinone glycoside compounds containing glucopyranoside group and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1721426A CN1721426A (en) | 2006-01-18 |
| CN100406465C true CN100406465C (en) | 2008-07-30 |
Family
ID=35912080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100189917A Expired - Fee Related CN100406465C (en) | 2005-06-24 | 2005-06-24 | Anthraquinone glycoside compounds containing glucopyranoside group and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100406465C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1546451A (en) * | 2003-12-05 | 2004-11-17 | 中山大学 | Hydroxyanthraquinone derivatives and their application in preparation of anticancer medicines |
-
2005
- 2005-06-24 CN CNB2005100189917A patent/CN100406465C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1546451A (en) * | 2003-12-05 | 2004-11-17 | 中山大学 | Hydroxyanthraquinone derivatives and their application in preparation of anticancer medicines |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1721426A (en) | 2006-01-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Rayyan et al. | Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug ‘crataegi folium cum flore’(hawthorn) | |
| RU2769512C2 (en) | Method for isolating eight compounds from composition based on chinese medicine drugs | |
| Deng et al. | Isolation and purification of three flavonoid glycosides from the leaves of Nelumbo nucifera (Lotus) by high-speed counter-current chromatography | |
| CN104860912B (en) | Dimer ketone compound and preparation method and application thereof | |
| Zhang et al. | Comparative evaluation of three methods based on high-performance liquid chromatography analysis combined with a 2, 2′-diphenyl-1-picrylhydrazyl assay for the rapid screening of antioxidants from Pueraria lobata flowers | |
| Xie et al. | Separation of flavonol glycosides from Flaveria bidentis (L.) Kuntze by high-speed counter-current chromatography | |
| Schaufelberger et al. | Chemistry and pharmacology of Gentiana lactea | |
| CN105503786A (en) | Secolignan compound-nettle secolignan glucoside E and preparation method thereof | |
| CN109320571B (en) | Method for extracting luteolin compound and cynaropicrin | |
| CN105481754A (en) | Indole alkaloid type compound and preparation method and application thereof | |
| CN105131063B (en) | From Meconopsis integrifolia spend in and meanwhile the method that isolates and purifies a variety of flavones ingredients | |
| CN100406465C (en) | Anthraquinone glycoside compounds containing glucopyranoside group and use thereof | |
| CN105669790B (en) | A kind of Bibenzyl compound and extracting method thereof | |
| CN106831892B (en) | Preparation method of flavone monomer in hawthorn leaves | |
| CN106928309B (en) | A kind of spirosolane type glycoalkaloid and preparation method thereof and purposes | |
| CN104844545B (en) | A kind of flavone compound and its extraction process | |
| Zhou et al. | Optimization, extraction, and purification of three bioactive compounds from Entada phaseoloides by high‐speed countercurrent chromatography | |
| CN105601600A (en) | Coumarins compound and extracting method thereof | |
| CN103113439A (en) | Method for preparing kaempferol-3-O-Beta-D-glucuronide in euphorbia sororia | |
| CN111793050A (en) | New compound in Iris tenuifolia and antioxidant activity thereof | |
| CN107325069B (en) | Extraction method of sesquiterpenoids | |
| CN106632197B (en) | Single plumage fire cylinder tree anticancer activity position LA-D and its pharmaceutical composition is separated with its chemical component and identification method | |
| CN105294812B (en) | A kind of preparation method of Ardisia mamillata triterpenoid saponin reference substance | |
| CN101343274B (en) | Carbazoles alkaloid, preparation and application thereof | |
| CN109490448A (en) | A kind of preparation method of digoxin standard substance |
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 | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080730 |