CN1398901A - Prepn and use of curcuma oligosaccharide sulfate derivative - Google Patents
Prepn and use of curcuma oligosaccharide sulfate derivative Download PDFInfo
- Publication number
- CN1398901A CN1398901A CN 01108650 CN01108650A CN1398901A CN 1398901 A CN1398901 A CN 1398901A CN 01108650 CN01108650 CN 01108650 CN 01108650 A CN01108650 A CN 01108650A CN 1398901 A CN1398901 A CN 1398901A
- Authority
- CN
- China
- Prior art keywords
- curcuma
- oligosaccharide
- ethanol
- concentration
- sulfate
- 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
Links
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 54
- -1 curcuma oligosaccharide sulfate derivative Chemical class 0.000 title claims abstract description 41
- 235000014375 Curcuma Nutrition 0.000 title claims description 53
- 244000164480 Curcuma aromatica Species 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 75
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 16
- 230000000840 anti-viral effect Effects 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims abstract description 8
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 5
- UFWWAKOWSBGGCP-UHFFFAOYSA-N pyridine;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.C1=CC=NC=C1 UFWWAKOWSBGGCP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 241000407170 Curcuma Species 0.000 claims description 52
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 28
- 229960004756 ethanol Drugs 0.000 claims description 28
- 241000700605 Viruses Species 0.000 claims description 19
- 150000002482 oligosaccharides Chemical class 0.000 claims description 18
- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 claims description 16
- 238000001556 precipitation Methods 0.000 claims description 12
- 208000030507 AIDS Diseases 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 7
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000004062 sedimentation Methods 0.000 claims description 7
- 238000013019 agitation Methods 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 5
- 239000006228 supernatant Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 208000002352 blister Diseases 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 208000006454 hepatitis Diseases 0.000 claims description 3
- 231100000283 hepatitis Toxicity 0.000 claims description 3
- 206010022000 influenza Diseases 0.000 claims description 3
- 230000007505 plaque formation Effects 0.000 claims description 3
- 229960004249 sodium acetate Drugs 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000011951 anti-virus test Methods 0.000 claims description 2
- 150000003463 sulfur Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 3
- 241000756042 Polygonatum Species 0.000 abstract 3
- 235000008737 Polygonatum biflorum Nutrition 0.000 abstract 3
- 230000008021 deposition Effects 0.000 abstract 1
- 238000002386 leaching Methods 0.000 abstract 1
- 229920001282 polysaccharide Polymers 0.000 description 9
- 239000005017 polysaccharide Substances 0.000 description 9
- 150000004804 polysaccharides Chemical class 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229930091371 Fructose Natural products 0.000 description 7
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 7
- 239000005715 Fructose Substances 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 210000003501 vero cell Anatomy 0.000 description 5
- MYKOKMFESWKQRX-UHFFFAOYSA-N 10h-anthracen-9-one;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 MYKOKMFESWKQRX-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- 241000725303 Human immunodeficiency virus Species 0.000 description 4
- 102100034349 Integrase Human genes 0.000 description 4
- 241000700584 Simplexvirus Species 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 241000701024 Human betaherpesvirus 5 Species 0.000 description 3
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 3
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 2
- 108010003533 Viral Envelope Proteins Proteins 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 150000002772 monosaccharides Chemical group 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000000452 restraining effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
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- 238000004809 thin layer chromatography Methods 0.000 description 2
- 108010041397 CD4 Antigens Proteins 0.000 description 1
- 229920002558 Curdlan Polymers 0.000 description 1
- 239000001879 Curdlan Substances 0.000 description 1
- 206010011831 Cytomegalovirus infection Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 102100038132 Endogenous retrovirus group K member 6 Pro protein Human genes 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 208000001688 Herpes Genitalis Diseases 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 108010090054 Membrane Glycoproteins Proteins 0.000 description 1
- 102000012750 Membrane Glycoproteins Human genes 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 241001633680 Polygonatum odoratum Species 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100036011 T-cell surface glycoprotein CD4 Human genes 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- 230000003602 anti-herpes Effects 0.000 description 1
- 230000000798 anti-retroviral effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940078035 curdlan Drugs 0.000 description 1
- 235000019316 curdlan Nutrition 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 150000002240 furans Chemical class 0.000 description 1
- 201000004946 genital herpes Diseases 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
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- 230000001524 infective effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
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- 235000019833 protease Nutrition 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical group 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 01108650 CN1256349C (en) | 2001-07-19 | 2001-07-19 | Prepn and use of curcuma oligosaccharide sulfate derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 01108650 CN1256349C (en) | 2001-07-19 | 2001-07-19 | Prepn and use of curcuma oligosaccharide sulfate derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1398901A true CN1398901A (en) | 2003-02-26 |
CN1256349C CN1256349C (en) | 2006-05-17 |
Family
ID=4657451
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 01108650 Expired - Fee Related CN1256349C (en) | 2001-07-19 | 2001-07-19 | Prepn and use of curcuma oligosaccharide sulfate derivative |
Country Status (1)
Country | Link |
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CN (1) | CN1256349C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1330670C (en) * | 2004-02-02 | 2007-08-08 | 中南大学湘雅二医院 | Process for extracting polygonatum polysaccharides, preparing process for medical preparation and use thereof |
CN100363373C (en) * | 2005-01-14 | 2008-01-23 | 庄茅 | Preparation method of isomalto loigosaccharide sulphate (IMOS) |
CN100404557C (en) * | 2005-12-09 | 2008-07-23 | 武汉理工大学 | Preparation method of umbellate pore fungus polysaccharide sulphate |
CN103627612A (en) * | 2013-09-30 | 2014-03-12 | 浙江致中和实业有限公司 | White spirit cold-soaking and countercurrent extraction method of polygonatum odoratum polysaccharide in brewing technique and online quality control method thereof |
CN112125983A (en) * | 2020-09-30 | 2020-12-25 | 华南理工大学 | Water-soluble polygonatum odoratum polysaccharide, sulfated polygonatum odoratum polysaccharide thereof, and preparation method and application of water-soluble polygonatum odoratum polysaccharide |
-
2001
- 2001-07-19 CN CN 01108650 patent/CN1256349C/en not_active Expired - Fee Related
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1330670C (en) * | 2004-02-02 | 2007-08-08 | 中南大学湘雅二医院 | Process for extracting polygonatum polysaccharides, preparing process for medical preparation and use thereof |
CN100363373C (en) * | 2005-01-14 | 2008-01-23 | 庄茅 | Preparation method of isomalto loigosaccharide sulphate (IMOS) |
CN100404557C (en) * | 2005-12-09 | 2008-07-23 | 武汉理工大学 | Preparation method of umbellate pore fungus polysaccharide sulphate |
CN103627612A (en) * | 2013-09-30 | 2014-03-12 | 浙江致中和实业有限公司 | White spirit cold-soaking and countercurrent extraction method of polygonatum odoratum polysaccharide in brewing technique and online quality control method thereof |
CN103627612B (en) * | 2013-09-30 | 2015-07-29 | 浙江致中和实业有限公司 | The white wine cold soaking of fragrant solomonseal rhizome polyoses, countercurrent extraction method and line Quality Control method thereof in wine-making technology |
CN112125983A (en) * | 2020-09-30 | 2020-12-25 | 华南理工大学 | Water-soluble polygonatum odoratum polysaccharide, sulfated polygonatum odoratum polysaccharide thereof, and preparation method and application of water-soluble polygonatum odoratum polysaccharide |
CN112125983B (en) * | 2020-09-30 | 2022-03-18 | 华南理工大学 | Water-soluble polygonatum odoratum polysaccharide, sulfated polygonatum odoratum polysaccharide thereof, and preparation method and application of water-soluble polygonatum odoratum polysaccharide |
Also Published As
Publication number | Publication date |
---|---|
CN1256349C (en) | 2006-05-17 |
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