CN1308298C - Guanido vitriol compound and its extraction and separation method - Google Patents
Guanido vitriol compound and its extraction and separation method Download PDFInfo
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- CN1308298C CN1308298C CNB2004100507544A CN200410050754A CN1308298C CN 1308298 C CN1308298 C CN 1308298C CN B2004100507544 A CNB2004100507544 A CN B2004100507544A CN 200410050754 A CN200410050754 A CN 200410050754A CN 1308298 C CN1308298 C CN 1308298C
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Abstract
The present invention relates to a guanidyl sulfate compound and a method for extracting and separating the guanidyl sulfate compound, which has the structural formula disclosed in the specification, and column separation technology is adopted. The compound of the present invention has the advantages of novel structure, simple and feasible method and fine application prospect.
Description
Technical field
The present invention relates to isolated compound from sponge, specifically a kind of guanidine sulfate based compound and extraction and separation method thereof.
Background technology
Sponge is the low multicellular animals of waiting, and is maximum natural product source.From sponge, isolated multiple natural product at present, mainly contain terpene, alkaloid, bromine-containing compound, steroid class etc., many unique chemical structures that have are wherein arranged, and have tangible activity, and have some to enter the clinical experiment stage at antibiotic, anti-inflammatory, aspect such as antitumor.
Sulphur is the fourth-largest element in the seawater, therefore contain a large amount of sulfocompounds in the marine organisms, it is not a lot of separating the sulfocompound that obtains comparatively speaking from sponge, having the compound of nearly 100 sulfur acid groups to separate from sponge obtains, (document 1:Jean-Michel Kornprobst, ClaireSallenave and Gilles Barnathan, Sulfated compounds from marine organisms, Comp.Biochem.Physiol, 1998,119B:1-15), compound is mainly terpene, aromatic series and steroid, activity show the anti-HIV-1 isoreactivity.The compound that contains guanidine radicals also is the natural product of often finding in the sponge, aspect (document 2:Boberto G.S.Berlinck such as that its activity is mainly reflected in is antibiotic, antiviral, anti-malarial, Natural guanidine derivatives, Natural ProductsReports, 2002,19:617-649).But do not find also that up to the present a kind of compound contains sulphur and guanidine radicals simultaneously.
Summary of the invention
The purpose of this invention is to provide a kind of new guanidine radicals sulphate and extraction and separation method thereof.
Technical solution of the present invention is as follows:
A kind of guanidine radicals sulphate, Chinese are 2-(N-methyl-guanidine radicals)-ethane sulfuric acid, and English name is 2-(N-methyl-guanidino)-ethanesulfonic acid, and its structural formula is as follows:
Its extraction and separation method is as follows: adopt the post isolation technique, use eluent solvent, the normal-phase chromatography post combines with the reversed phase chromatography post, separation and Extraction operation as follows: with the soft sponge of many wrinkles (Halichondria rugosa Ridley﹠amp; Dendy) be raw material, get 2～3 kilograms of lyophilize choppings, stir extraction with 1000～2000 milliliters methyl alcohol, extract is concentrated into soup compound and evenly spreads in 100～200ml water, water-soluble extract, use hexanaphthene, ethyl acetate, propyl carbinol with water-soluble extract equivalent to extract successively from small to large respectively according to organic solvent polarity again; The extraction liquid of the butanol extraction liquid gained of polarity maximum is concentrated after silica gel column chromatography and reversed phase column chromatography separate, obtain the white needle-like crystals product.
Described being extracted as: extract 3～5 times with 1000～2000 milliliters methyl alcohol stirring at normal temperature, each 3-5 hour, be scattered in isopyknic water after united extraction thing and underpressure distillation are concentrated into 100～200 milliliters, again according to the extraction successively from small to large of organic solvent polarity;
The post isolation technique is: enriched material when silica gel column chromatography, with the methylene chloride-methanol gradient elution, the cut underpressure distillation of methylene dichloride 60%, concentrated solution is again through an ODS reversed-phase column column chromatography, use the water-methanol gradient elution, the cut underpressure distillation that obtains removes and desolvates, and obtains the white powder product.
The present invention compared with prior art has following beneficial effect:
1. compound structure novelty.Adopt extraction and separation process of the present invention, from the soft sponge of many wrinkles, obtain and determined the structure of active compound first; Has novel structural characteristics.
2. method is simple and feasible.The present invention only separates with the reversed phase chromatography post by positive in sepn process, can obtain pure new compound.
3. have a good application prospect.The compounds of this invention is a kind of activity and anti-tumor activity with extremely strong anti-HIV-1 virus, can be used as anti-HIV-1 virus and antineoplastic lead compound.This compound molecular weight is little simultaneously, has water-solublely, and this class character has remarkable advantages as lead compound research.
Embodiment
Embodiment 1
A kind of guanidine radicals sulphate structural formula is as follows:
Its extraction and separation method is with the soft sponge of the many wrinkles of South China Sea (Halichondria rugosaRidley﹠amp; Dendy) be raw material, the method that adopts normal phase column to combine with reversed-phase column, can operate as follows:
Gather the soft sponge of the many wrinkles of South China Sea (Halichondria rugosa Ridley﹠amp; Dendy), after the collection immediately in-20 ℃ of freezing preservations of refrigerator, lyophilize during use (100g), pulverize, mechanical stirring is extracted in methyl alcohol, repeats 4 times, and united extraction thing and underpressure distillation are concentrated into soup compound, soup compound is dispersed in the 100ml water, use the hexanaphthene of equivalent respectively, ethyl acetate, propyl carbinol extracts 3 times successively, and n-butyl alcohol extract is through concentrating under reduced pressure, and enriched material is through silica gel (Qingdao Haiyang chemical industry subsidiary factory, the 300-400 order) column chromatography, successively with the methylene chloride-methanol (100%, 80%, 60% of 500ml different ratios, 40%, 20%, 0) wash-out, the cut underpressure distillation of methylene dichloride 60%, concentrated solution is again through an ODS reversed-phase column (5g, the import packing, Beijing Jin Ouya company, 40-60 micron) column chromatography, with 50ml water-methanol (100%, 50%, 0) wash-out, the cut underpressure distillation that obtains removes and desolvates, obtain white powder 10mg, purity reaches 90%.
Structure is identified:
Physical constant: fusing point:＞300 ℃; Solvability: soluble in water;
Spectroscopic data: UV spectrum: do not have uv-absorbing under the＞200nm wavelength; Infrared spectra υ
Max(KBr, cm
-1): 3363,3220,3177,2926,2853,1661,1638,1543,1462,1376,1264,1205,1108,1053,1040,1024,1002,825,782,727,629,562,526,468; Nuclear magnetic resonance spectrum: δ
1 H(D
2O, TMS) ppm:3.83 (2H, t), 3.29 (2H, t), 3.12 (3H, s); δ
13 C(D
2O/CD
3OD, TMS) ppm:158.00,48.23,47.21,36.68; Electrospray ionization mass spectrum: positive ion mode: 204[M+Na]
+, 385[2M+Na]
+Negative ion mode: 180[M-H]
-, 361[2M-H]
-It is 182.05946 that high resolution mass spec (HRMS) obtains molecular weight, and molecular formula is: C
4H
11N
3O
3S
Physiologically active: compound has the obvious suppression effect to HIV-1 inductive C8166 cytopathy, active (EE
50) be 29ug/ml, to the then less (CC of the toxicity of host cell
50)＞200ug/ml.
Embodiment 2
With the 2 kilograms of choppings of fresh sponge that collect, directly stir extraction with 2000 ml methanol, extraction liquid is concentrated into 1000 milliliters, and identical with embodiment 1 again method extracts successively and separates, and obtains colourless acicular crystal.
Claims (3)
1. guanidine radicals sulphate, it is characterized in that: structural formula is as follows,
2. the extraction and separation method of the described guanidine radicals sulphate of claim 1, it is characterized in that: adopt the post isolation technique, use eluent solvent, separation and Extraction operation as follows, with the soft sponge of many wrinkles is raw material for 2～3 kilograms, the lyophilize chopping, stir extraction with 1000～2000 milliliters methyl alcohol, extract is concentrated into soup compound, soup compound is dispersed in 100～200ml water, gets water-soluble extract, use hexanaphthene respectively with water-soluble extract equivalent, ethyl acetate, propyl carbinol extracts successively, n-butyl alcohol extract concentrates after silica gel column chromatography separates with the reversed phase chromatography post, obtains the white needle-like crystals product; Enriched material when silica gel column chromatography, with methylene dichloride-methyl alcohol gradient elution, the cut underpressure distillation of methylene dichloride 60%, concentrated solution is again through an ODS reversed-phase column column chromatography, water-methyl alcohol gradient elution, the cut underpressure distillation that obtains removes and desolvates, and obtains the white powder product.
3. according to the described extraction and separation method of claim 2, it is characterized in that: extract 3～5 times with 1000～2000 milliliters methyl alcohol stirring at normal temperature, each 3-5 hour, after being concentrated into 100～200 milliliters, united extraction thing and underpressure distillation be scattered in isopyknic water, again according to the extraction successively from small to large of organic solvent polarity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100507544A CN1308298C (en) | 2004-10-29 | 2004-10-29 | Guanido vitriol compound and its extraction and separation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100507544A CN1308298C (en) | 2004-10-29 | 2004-10-29 | Guanido vitriol compound and its extraction and separation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1765881A CN1765881A (en) | 2006-05-03 |
| CN1308298C true CN1308298C (en) | 2007-04-04 |
Family
ID=36742023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100507544A Expired - Fee Related CN1308298C (en) | 2004-10-29 | 2004-10-29 | Guanido vitriol compound and its extraction and separation method |
Country Status (1)
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| CN (1) | CN1308298C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1141624A (en) * | 1994-02-22 | 1997-01-29 | 花王株式会社 | Taurine derivatives for use in cleanser compositions |
-
2004
- 2004-10-29 CN CNB2004100507544A patent/CN1308298C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1141624A (en) * | 1994-02-22 | 1997-01-29 | 花王株式会社 | Taurine derivatives for use in cleanser compositions |
Non-Patent Citations (1)
| Title |
|---|
| 中国海绵天然产物的研究 薛松等，天然产物研究与开发，第15卷第4期 2003 * |
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| Publication number | Publication date |
|---|---|
| CN1765881A (en) | 2006-05-03 |
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Granted publication date: 20070404 Termination date: 20091130 |