CN102058613A - New application of antineoplastic constituent compound in solanum nigrum - Google Patents
New application of antineoplastic constituent compound in solanum nigrum Download PDFInfo
- Publication number
- CN102058613A CN102058613A CN2011100053503A CN201110005350A CN102058613A CN 102058613 A CN102058613 A CN 102058613A CN 2011100053503 A CN2011100053503 A CN 2011100053503A CN 201110005350 A CN201110005350 A CN 201110005350A CN 102058613 A CN102058613 A CN 102058613A
- Authority
- CN
- China
- Prior art keywords
- solamargine
- solasonine
- group
- weight ratio
- injection
- 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
- 244000061457 Solanum nigrum Species 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 title abstract description 3
- 235000002594 Solanum nigrum Nutrition 0.000 title description 2
- 230000000118 anti-neoplastic effect Effects 0.000 title 1
- 239000000470 constituent Substances 0.000 title 1
- 239000003814 drug Substances 0.000 claims abstract description 8
- 201000007270 liver cancer Diseases 0.000 claims abstract description 6
- 208000014018 liver neoplasm Diseases 0.000 claims abstract description 6
- MBWUSSKCCUMJHO-ZGXDEBHDSA-N Solamargine Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(NC[C@H](C)CC1)O5)C)[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O MBWUSSKCCUMJHO-ZGXDEBHDSA-N 0.000 claims description 34
- MBWUSSKCCUMJHO-DVDUUUGDSA-N Solamargine Natural products O([C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O2)[C@H](CO)O[C@@H]1O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]5[C@@H](C)[C@@]6(O[C@H]5C4)NC[C@H](C)CC6)CC3)CC=2)CC1)[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](C)O1 MBWUSSKCCUMJHO-DVDUUUGDSA-N 0.000 claims description 33
- QCTMYNGDIBTNSK-XEAAVONHSA-N α-Solamarine Chemical compound O([C@H]1[C@@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@H](O)[C@@H](O)[C@H](C)O1)O)O[C@@H]1CC2=CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(NC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QCTMYNGDIBTNSK-XEAAVONHSA-N 0.000 claims description 31
- KNLOWJPFLKGYGQ-UHFFFAOYSA-N Solasodine 3-O-??-L-rhamnopyranosyl (1‘Â∆2)-O-[??-D-glucopyranosyl (1‘Â∆4)]-??-D-glucopyranoside Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C(C1O)OC2C(C(O)C(O)C(C)O2)O)OC(CO)C1OC1OC(CO)C(O)C(O)C1O KNLOWJPFLKGYGQ-UHFFFAOYSA-N 0.000 claims description 30
- QCTMYNGDIBTNSK-UHFFFAOYSA-N Solasonin Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C1OC2C(C(O)C(O)C(C)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O QCTMYNGDIBTNSK-UHFFFAOYSA-N 0.000 claims description 30
- QCTMYNGDIBTNSK-QCNFCIKQSA-N Solasonine Natural products O([C@@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O2)[C@@H](O[C@@H]2CC=3[C@@](C)([C@@H]4[C@H]([C@H]5[C@@](C)([C@H]6[C@@H](C)[C@@]7(O[C@H]6C5)NC[C@H](C)CC7)CC4)CC=3)CC2)O[C@@H](CO)[C@@H]1O)[C@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 QCTMYNGDIBTNSK-QCNFCIKQSA-N 0.000 claims description 30
- RCTKRNCKOYYRIO-UHFFFAOYSA-N alpha-Solamarine Natural products O1C2(NCC(C)CC2)C(C)C(C2(CCC3C4(C)CC5)C)C1CC2C3CC=C4CC5OC(C1O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O RCTKRNCKOYYRIO-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 14
- 239000005414 inactive ingredient Substances 0.000 claims 1
- 239000000284 extract Substances 0.000 abstract description 3
- 229940090044 injection Drugs 0.000 description 25
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- 206010028980 Neoplasm Diseases 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000002131 composite material Substances 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000011580 nude mouse model Methods 0.000 description 8
- 241000699660 Mus musculus Species 0.000 description 7
- 239000000178 monomer Substances 0.000 description 6
- 230000035755 proliferation Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- 230000000857 drug effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 description 2
- JXWLYDNHVXFBJA-UHFFFAOYSA-N solasodine Natural products CC1CCC2(NC1)NC3CC4C5CC=C6CC(O)CCC6(C)C5CCC4(C)C3C2C JXWLYDNHVXFBJA-UHFFFAOYSA-N 0.000 description 2
- 229930003352 steroid alkaloid Natural products 0.000 description 2
- 230000005909 tumor killing Effects 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- 238000011728 BALB/c nude (JAX™ mouse strain) Methods 0.000 description 1
- 208000030808 Clear cell renal carcinoma Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 229940105442 cisplatin injection Drugs 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000000205 computational method Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930008677 glyco alkaloid Natural products 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000012109 statistical procedure Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110005350.3A CN102058613B (en) | 2011-01-12 | 2011-01-12 | The purposes of anti-tumor active ingredient compositions in Herba Solani Nigri |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110005350.3A CN102058613B (en) | 2011-01-12 | 2011-01-12 | The purposes of anti-tumor active ingredient compositions in Herba Solani Nigri |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102058613A true CN102058613A (en) | 2011-05-18 |
CN102058613B CN102058613B (en) | 2015-12-16 |
Family
ID=43994239
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201110005350.3A Active CN102058613B (en) | 2011-01-12 | 2011-01-12 | The purposes of anti-tumor active ingredient compositions in Herba Solani Nigri |
Country Status (1)
Country | Link |
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CN (1) | CN102058613B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112957364A (en) * | 2021-03-29 | 2021-06-15 | 杭州立效生物医药科技有限公司 | Medicine for treating renal tubular injury and application thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040247715A1 (en) * | 2003-06-05 | 2004-12-09 | G & E Herbal Biotechnology Co., Ltd. | Water soluble extract from plant of solanum genus and the preparation process thereof, and pharmaceutical composition containing the water soluble extract |
-
2011
- 2011-01-12 CN CN201110005350.3A patent/CN102058613B/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040247715A1 (en) * | 2003-06-05 | 2004-12-09 | G & E Herbal Biotechnology Co., Ltd. | Water soluble extract from plant of solanum genus and the preparation process thereof, and pharmaceutical composition containing the water soluble extract |
Non-Patent Citations (1)
Title |
---|
KAP-RANG LEE, ET AL.: "Glycoalkaloids and Metabolites Inhibit the Growth of Human Colon (HT29) and Liver (HepG2) Cancer Cells", 《J. AGRIC. FOOD CHEM.》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112957364A (en) * | 2021-03-29 | 2021-06-15 | 杭州立效生物医药科技有限公司 | Medicine for treating renal tubular injury and application thereof |
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Publication number | Publication date |
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CN102058613B (en) | 2015-12-16 |
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Legal Events
Date | Code | Title | Description |
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C06 | Publication | ||
PB01 | Publication | ||
C53 | Correction of patent of invention or patent application | ||
CB02 | Change of applicant information |
Address after: 210042 Xuanwu District, Xuanwu District, Jiangsu, Nanjing No. 699 -18 Applicant after: Jiangsu Simcere Pharmaceutical Research Company Limited Address before: 210042 -18, Xuanwu Avenue, Xuanwu District, Jiangsu, Nanjing, 669 Applicant before: Jiangsu Simcere Pharmaceutical Research Company Limited |
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C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
ASS | Succession or assignment of patent right |
Owner name: JIANGSU SIMCERE PHARMACEUTICAL CO., LTD. Effective date: 20150625 |
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C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20150625 Address after: 210042 Xuanwu District, Xuanwu District, Jiangsu, Nanjing No. 699 -18 Applicant after: Jiangsu Simcere Pharmaceutical Research Company Limited Applicant after: Jiangsu Simcere Pharmaceutical Co., Ltd. Address before: 210042 Xuanwu District, Xuanwu District, Jiangsu, Nanjing No. 699 -18 Applicant before: Jiangsu Simcere Pharmaceutical Research Company Limited |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20160711 Address after: 210042 Xuanwu District, Xuanwu District, Jiangsu, Nanjing No. 699 -18 Patentee after: Jiangsu Simcere Pharmaceutical Co., Ltd. Address before: 210042 Xuanwu District, Xuanwu District, Jiangsu, Nanjing No. 699 -18 Patentee before: Jiangsu Simcere Pharmaceutical Research Company Limited Patentee before: Jiangsu Simcere Pharmaceutical Co., Ltd. |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20201229 Address after: 570311 No. 2 Yaogu No. 3 Road, Xiuying District, Haikou City, Hainan Province Patentee after: Hainan Simcere Pharmaceutical Co.,Ltd. Address before: 210042 699 Xuanwu Road, Xuanwu District, Nanjing, Jiangsu -18 Patentee before: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. |