Proscillaridin (BioDeep_00000000871)
Secondary id: BioDeep_00000182666
natural product PANOMIX_OTCML-2023 Chemicals and Drugs Toxin Antitumor activity
代谢物信息卡片
化学式: C30H42O8 (530.288)
中文名称: 原海葱甙A
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 33.33%
分子结构信息
SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])(C5=COC(=O)C=C5)CC[C@]4(O)[C@]3([H])CCC2=C[C@@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O2)C1
InChI: InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21-,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1
描述信息
Proscillaridin is an organic molecular entity.
Proscillaridin is a cardiac glycoside that is derived from plants of the genus Scilla and in Drimia maritima (Scilla maritima). Studies suggest the potential cytotoxic and anticancer property of proscillaridin, based on evidence of the drug potently disrupting topoisomerase I and II activity at nanomolar drug concentrations and triggering cell death and blocking cell proliferation of glioblastoma cell lines.
Proscillaridin is a natural product found in Drimia indica with data available.
A cardiotonic glycoside isolated from Scilla maritima var. alba (Squill).
C - Cardiovascular system > C01 - Cardiac therapy > C01A - Cardiac glycosides > C01AB - Scilla glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002301 - Cardiac Glycosides
D020011 - Protective Agents > D002316 - Cardiotonic Agents > D002018 - Bufanolides
C78274 - Agent Affecting Cardiovascular System > C78322 - Cardiotonic Agent
D002317 - Cardiovascular Agents
D004791 - Enzyme Inhibitors
Proscillaridin A is a potent poison of topoisomerase I/II activity with IC50 values of 30 nM and 100 nM, respectively[1].
Proscillaridin A is a potent poison of topoisomerase I/II activity with IC50 values of 30 nM and 100 nM, respectively[1].
同义名列表
85 个代谢物同义名
5-[(3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one; BUFA-4,20,22-TRIENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-14-HYDROXY-, (3.BETA.)-; Bufa-4,20,22-trienolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-14-hydroxy-, (3-beta)-; Bufa-4,20,22-trienolide, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-14-hydroxy-, (3beta)-; (3beta)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide; 3-beta-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-14-hydroxybufa-4,20,22-trienolide; Bufa-4,20,22-trienolide,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-14-hydroxy-, (3b)-; Bufa-4,20,22-trienolide, 3-beta-((6-deoxy-alpha-L-mannosyl)oxy)-14-hydroxy-; 3-O-(alpha-L-rhamnopyranosyl)-3beta,14beta-dihydroxybufa-4,20,22-trienolide; ((6-Deoxy-.alpha.-L-mannopyranosyl)oxy)-14-hydroxybufa-4,20,22-trienolide; ((6-Deoxy-alpha-L-mannopyranosyl)oxy)-14-hydroxybufa-4,20,22-trienolide; 3-beta-Rhamnosido-14-beta-hydroxy-delta(sup 4,20,22)-bufatrienolide; 3-beta,14-beta-Dihydroxybufa-4,20,22-trienolide 3-rhamnoside; 14-Hydroxy-3-beta-(rhamnosyloxy)bufa-4,20,22-trienolide; 14-Hydroxy-3beta-(rhamnosyloxy)bufa-4,20,22-trienolide; Rhamnopyranoside, scillarenin-3, alpha-L-; Scillarenin, 3-alpha-L-rhamnopyranoside; Scillarenin, 3alpha-L-rhamnopyranoside; Proscillaridin [USAN:INN:BAN:JAN]; Proscillaridin (JAN/USAN/INN); Scillarenin-rhamnose [German]; Scillarenin 3-beta-rhamnoside; Proscillaridinum [INN-Latin]; Scillarenin 3beta-rhamnoside; Proscillaridine [INN-French]; Proscilaridina [INN-Spanish]; MYEJFUXQJGHEQK-ALRJYLEOSA-N; Scillarenin 3-O-rhamnoside; PROSCILLARIDIN [WHO-DD]; Rhamnoside, Scillarenin; Proscillaridina [DCIT]; PROSCILLARIDIN [MART.]; Scillarenin Rhamnoside; Proscilardyna [Polish]; PROSCILLARIDIN [USAN]; Transvaalin, degluco-; PROSCILLARIDIN [JAN]; PROSCILLARIDIN [INN]; Desglucotransvaaline; Desgluco-transvaalin; Scillarenin-rhamnose; PROSCILLARIDIN [MI]; Desglucotransvaalin; Herzo proscillan; Proscillaridin A; Proscillaridinum; Proscillaridina; UNII-KC6BL281EN; Proscillaridine; Proscilaridina; Tox21_110442_1; Proscillaridin; Proscilardyna; Scilla didier; Tox21_110442; Talusin (TN); Scillacrist; Digitalysat; Proslladin; Purosin-TC; Sandoscill; KC6BL281EN; Cardiovite; Proscillan; Stellarid; Procardin; Caradrine; Solestril; Prostosin; Talucard; Procilan; Tradenal; Wirnesin; Scillase; Protasin; Caradrin; Carmazon; Cardion; Talusin; Proszin; Urgilan; Coratol; Simeon; Herzo; Proscillaridin
数据库引用编号
39 个数据库交叉引用编号
- ChEBI: CHEBI:32065
- KEGG: C12816
- KEGGdrug: D01379
- PubChem: 52931497
- PubChem: 5284613
- PubChem: 4951
- DrugBank: DB13307
- ChEMBL: CHEMBL600325
- Wikipedia: Proscillaridin
- LipidMAPS: LMST01130008
- MeSH: Proscillaridin
- ChemIDplus: 0000466068
- CAS: 466-06-8
- MoNA: WA002525
- MoNA: WA002524
- MoNA: WA002523
- MoNA: WA002522
- MoNA: VF-NPL-QEHF010101
- MoNA: VF-NPL-QEHF010100
- MoNA: VF-NPL-QEHF010099
- MoNA: VF-NPL-QEHF010098
- MoNA: VF-NPL-QEHF010097
- MoNA: VF-NPL-QEHF010096
- MoNA: VF-NPL-QEHF010095
- MoNA: VF-NPL-QEHF010094
- MoNA: VF-NPL-QEHF010093
- MoNA: VF-NPL-QEHF010092
- MoNA: VF-NPL-QEHF010091
- MoNA: VF-NPL-QEHF010090
- MoNA: VF-NPL-QEHF010089
- MoNA: VF-NPL-QEHF010088
- MoNA: VF-NPL-QEHF010087
- medchemexpress: HY-N2331
- PMhub: MS000001753
- PubChem: 583205
- RefMet: Proscillaridin A
- LOTUS: LTS0096772
- LOTUS: LTS0269036
- LOTUS: LTS0053662
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
39 个相关的物种来源信息
- 40552 - Asparagaceae: LTS0053662
- 40552 - Asparagaceae: LTS0096772
- 40552 - Asparagaceae: LTS0269036
- 510735 - Crataegus pinnatifida Bge.: -
- 65772 - Drimia: LTS0053662
- 65772 - Drimia: LTS0096772
- 65772 - Drimia: LTS0269036
- 81800 - Drimia indica: 10.1016/0031-9422(81)80065-9
- 81800 - Drimia indica: 10.1055/S-2007-969946
- 81800 - Drimia indica: LTS0053662
- 81800 - Drimia indica: LTS0269036
- 82070 - Drimia maritima: 10.1002/HLCA.19330160198
- 82070 - Drimia maritima: 10.1002/HLCA.193401701162
- 82070 - Drimia maritima: 10.1016/0031-9422(95)00876-4
- 82070 - Drimia maritima: 10.1016/S0367-326X(99)00142-2
- 82070 - Drimia maritima: 10.1055/S-2006-960924
- 82070 - Drimia maritima: 10.1248/CPB.49.282
- 2759 - Eukaryota: LTS0053662
- 2759 - Eukaryota: LTS0096772
- 2759 - Eukaryota: LTS0269036
- 44985 - Hyacinthaceae: LTS0053662
- 44985 - Hyacinthaceae: LTS0096772
- 44985 - Hyacinthaceae: LTS0269036
- 4447 - Liliopsida: LTS0053662
- 4447 - Liliopsida: LTS0096772
- 4447 - Liliopsida: LTS0269036
- 3398 - Magnoliopsida: LTS0053662
- 3398 - Magnoliopsida: LTS0096772
- 3398 - Magnoliopsida: LTS0269036
- 33090 - Plants: -
- 35493 - Streptophyta: LTS0053662
- 35493 - Streptophyta: LTS0096772
- 35493 - Streptophyta: LTS0269036
- 58023 - Tracheophyta: LTS0053662
- 58023 - Tracheophyta: LTS0096772
- 58023 - Tracheophyta: LTS0269036
- 33090 - Viridiplantae: LTS0053662
- 33090 - Viridiplantae: LTS0096772
- 33090 - Viridiplantae: LTS0269036
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Umesh Chandra Dash, Sandeep Kumar Swain, Atala Bihari Jena, Jagnehswar Dandapat, Atish Kumar Sahoo. The ameliorative effect of Piper trioicum in attenuating cognitive deficit in scopolamine induced neurotoxicity in experimental rats.
Journal of ethnopharmacology.
2023 Jul; ?(?):116911. doi:
10.1016/j.jep.2023.116911
. [PMID: 37451488] - S Aishwarya, K Gunasekaran, A Anita Margret. Computational gene expression profiling in the exploration of biomarkers, non-coding functional RNAs and drug perturbagens for COVID-19.
Journal of biomolecular structure & dynamics.
2022 05; 40(8):3681-3696. doi:
10.1080/07391102.2020.1850360
. [PMID: 33228475] - Shuo Fang, Hai Tao, Kezhou Xia, Weichun Guo. Proscillaridin A induces apoptosis and inhibits the metastasis of osteosarcoma in vitro and in vivo.
Biochemical and biophysical research communications.
2020 01; 521(4):880-886. doi:
10.1016/j.bbrc.2019.11.012
. [PMID: 31708095] - Francisco Triana-Martínez, Pilar Picallos-Rabina, Sabela Da Silva-Álvarez, Federico Pietrocola, Susana Llanos, Verónica Rodilla, Enrica Soprano, Pablo Pedrosa, Alba Ferreirós, Marta Barradas, Fernanda Hernández-González, Marta Lalinde, Neus Prats, Cristina Bernadó, Patricia González, María Gómez, Maria P Ikonomopoulou, Pablo J Fernández-Marcos, Tomás García-Caballero, Pablo Del Pino, Joaquín Arribas, Anxo Vidal, Miguel González-Barcia, Manuel Serrano, María I Loza, Eduardo Domínguez, Manuel Collado. Identification and characterization of Cardiac Glycosides as senolytic compounds.
Nature communications.
2019 10; 10(1):4731. doi:
10.1038/s41467-019-12888-x
. [PMID: 31636264] - Elnaz Gozalpour, Martijn J Wilmer, Albert Bilos, Rosalinde Masereeuw, Frans G M Russel, Jan B Koenderink. Heterogeneous transport of digitalis-like compounds by P-glycoprotein in vesicular and cellular assays.
Toxicology in vitro : an international journal published in association with BIBRA.
2016 Apr; 32(?):138-45. doi:
10.1016/j.tiv.2015.12.009
. [PMID: 26708294] - Hesham R El-Seedi, Robert Burman, Ahmed Mansour, Zaki Turki, Loutfy Boulos, Joachim Gullbo, Ulf Göransson. The traditional medical uses and cytotoxic activities of sixty-one Egyptian plants: discovery of an active cardiac glycoside from Urginea maritima.
Journal of ethnopharmacology.
2013 Feb; 145(3):746-57. doi:
10.1016/j.jep.2012.12.007
. [PMID: 23228916] - Heidrun Weidemann. 'The Lower Threshold' phenomenon in tumor cells toward endogenous digitalis-like compounds: Responsible for tumorigenesis?.
Journal of carcinogenesis.
2012; 11(?):2. doi:
10.4103/1477-3163.92999
. [PMID: 22438768] - Jenny Felth, Linda Rickardson, Josefin Rosén, Malin Wickström, Mårten Fryknäs, Magnus Lindskog, Lars Bohlin, Joachim Gullbo. Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.
Journal of natural products.
2009 Nov; 72(11):1969-74. doi:
10.1021/np900210m
. [PMID: 19894733] - Yutaka Komiyama, Xian Hui Dong, Noriko Nishimura, Hiroya Masaki, Masamichi Yoshika, Midori Masuda, Hakuo Takahashi. A novel endogenous digitalis, telocinobufagin, exhibits elevated plasma levels in patients with terminal renal failure.
Clinical biochemistry.
2005 Jan; 38(1):36-45. doi:
10.1016/j.clinbiochem.2004.08.005
. [PMID: 15607315] - R Schneider, R Antolovic, H Kost, B Sich, U Kirch, M Tepel, W Zidek, W Schoner. Proscillaridin A immunoreactivity: its purification, transport in blood by a specific binding protein and its correlation with blood pressure.
Clinical and experimental hypertension (New York, N.Y. : 1993).
1998 Jul; 20(5-6):593-9. doi:
10.3109/10641969809053237
. [PMID: 9682915] - S Li, C Eim, U Kirch, R E Lang, W Schoner. Bovine adrenals and hypothalamus are a major source of proscillaridin A- and ouabain-immunoreactivities.
Life sciences.
1998; 62(11):1023-33. doi:
10.1016/s0024-3205(98)00023-x
. [PMID: 9515560] - B Sich, U Kirch, M Tepel, W Zidek, W Schoner. Pulse pressure correlates in humans with a proscillaridin A immunoreactive compound.
Hypertension (Dallas, Tex. : 1979).
1996 May; 27(5):1073-8. doi:
10.1161/01.hyp.27.5.1073
. [PMID: 8621199] - A T Nguyen, P A Doris. Role of endogenous cardiac glycosides in the spontaneously hypertensive rat--antagonism by active immunization.
American journal of hypertension.
1996 Jan; 9(1):81-5. doi:
10.1016/0895-7061(95)00291-x
. [PMID: 8834711] - T Tanase, N Murakami, A Nagatsu, S Nagai, J Sakakibara, H Ando, Y Hotta, K Takeya, M Asano. [Studies on cardiac ingredients of plants. X. Preparation of nitrates of tetrahydroproscillaridin and their pharmacological activities].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
1992 Nov; 112(11):792-803. doi:
10.1248/yakushi1947.112.11_792
. [PMID: 1336548] - T Tanase, N Murakami, S Nagai, T Ueda, J Sakakibara, H Ando, Y Hotta, K Takeya. Studies on cardiac ingredients of plants. IX. Chemical transformation of proscillaridin by utilizing its 1,4-cycloadducts as key compounds and biological activities of their derivatives.
Chemical & pharmaceutical bulletin.
1992 Feb; 40(2):327-32. doi:
10.1248/cpb.40.327
. [PMID: 1318790] - N Murakami, Y Sato, T Tanase, S Nagai, T Ueda, J Sakakibara, H Ando, Y Hotta, K Takeya, M Asano. [Studies on cardiac ingredients of plants. VIII. Preparation of nitrates of proscillaridin and their pharmacological activities].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
1991 Aug; 111(8):436-44. doi:
10.1248/yakushi1947.111.8_436
. [PMID: 1665512] - N Murakami, T Tanase, S Nagai, Y Sato, T Ueda, J Sakakibara, H Ando, Y Hotta, K Takeya. Studies on cardiac ingredients of plants. VII: Chemical transformation of proscillaridin by means of the Diels-Alder reaction and biological activities of its derivatives.
Chemical & pharmaceutical bulletin.
1991 Aug; 39(8):1962-6. doi:
10.1248/cpb.39.1962
. [PMID: 1839142] - K Kojima, K Yamamoto, Y Terauchi, A Kagemoto, S Naruto, Y Nakanishi. Determination of proscillaridin in plasma by radioimmunoassay.
Journal of pharmacobio-dynamics.
1986 Aug; 9(8):665-71. doi:
10.1248/bpb1978.9.665
. [PMID: 3783410] - H D Lehmann. [Effect of plant glycosides on resistance and capacitance vessels].
Arzneimittel-Forschung.
1984; 34(4):423-9. doi:
. [PMID: 6540100]
- K Burkert, H Beckmann. [Plasma concentration and elimination behavior of the cardiac glycoside meproscillarin in patients with liver cirrhosis].
Zeitschrift fur Gastroenterologie.
1983 Jan; 21(1):34-40. doi:
NULL
. [PMID: 6845784] - U Peters. Pharmacokinetic review of digitalis glycosides.
European heart journal.
1982 Dec; 3 Suppl D(?):65-78. doi:
NULL
. [PMID: 6761129] - J Bonelli. [Therapy of chronic cardiac insufficiency with cardiac glycosides].
Wiener medizinische Wochenschrift (1946).
1982 Oct; 132(19):442-9. doi:
NULL
. [PMID: 7179995] - M Rupp, H Brass, D Glöckler. [Problems of glycoside therapy in kidney insufficiency and uremia].
Die Medizinische Welt.
1981 Jan; 32(4):115-22. doi:
NULL
. [PMID: 7207142] - H Beckmann, G G Belz, E Quellhorst. [Meproscillarin in patients with renal failure and concomitant heart failure (author's transl)].
Medizinische Klinik.
1979 Nov; 74(47):1761-6. doi:
NULL
. [PMID: 522817] - B Bergdahl. Disposition rate of proscillaridin A in man after multiple oral doses.
Arzneimittel-Forschung.
1979; 29(2):343-5. doi:
. [PMID: 582147]
- D S Regal. [Effect of proscillaridin on adenosine triphosphatase in kidney tissue in the rat. Electron microscopy demonstration and significance for calcium metabolism].
Zentralblatt fur Veterinarmedizin. Reihe A.
1978 Nov; 25(9):704-17. doi:
. [PMID: 153691]
- J Bonelli. [Modern cardiac glycoside therapy].
Wiener medizinische Wochenschrift (1946).
1978; 128(22):689-96. doi:
NULL
. [PMID: 735108] - K E Andersson, B Bergdahl, H Dencker, G Wettrell. Proscillaridin activity in portal and peripheral venous blood after oral administration to man.
European journal of clinical pharmacology.
1977 Apr; 11(4):277-81. doi:
10.1007/bf00607677
. [PMID: 862648] - B Bergdahl, K E Andersson. Stability in vitro of methylproscillaridin.
European journal of clinical pharmacology.
1977 Apr; 11(4):267-71. doi:
10.1007/bf00607675
. [PMID: 16755] - K E Andersson, B Bergdahl, G Wettrell. Biliary excretion and enterochepatic recycling of proscillaridin A after oral adminstration to man.
European journal of clinical pharmacology.
1977 Apr; 11(4):273-6. doi:
10.1007/bf00607676
. [PMID: 862647] - K E Andersson, B Bergdahl, H Dencker, G Wettrell. Activities of proscillaridin A in thoracic duct lymph after single oral doses in man.
Acta pharmacologica et toxicologica.
1977 Feb; 40(2):280-4. doi:
10.1111/j.1600-0773.1977.tb02079.x
. [PMID: 576557] - K E Andersson, B Bergdah, A Bertler, A Redfors. On the absorption of proscillaridin A after single oral doses to normal and achlorhydric subjects.
Acta pharmacologica et toxicologica.
1977 Jan; 40(1):153-60. doi:
10.1111/j.1600-0773.1977.tb02063.x
. [PMID: 576356] - G Neugebauer. [Influence of high intravenous doses of D-penicillamine on toxic actions of cardiac glycosides in the guinea pig. Short communication (author's transl)].
Arzneimittel-Forschung.
1977; 27(11):2073-4. doi:
NULL
. [PMID: 580003] - G G Belz, H Schreiter, G K Wolf. Pharmacokinetics and pharmacodynamics of methyl proscillaridin in healthy man.
European journal of clinical pharmacology.
1976 Jun; 10(2):101-8. doi:
10.1007/bf00609467
. [PMID: 786669] - G G Belz, H Nübling, G Belz. Plasma concentrations during repeated intravenous and oral methyl-proscillaridin application in man.
Arzneimittel-Forschung.
1976 Feb; 26(2):277-8. doi:
NULL
. [PMID: 947212] - R Staud, N Rietbrock, H P Fassbender. Excretion of methylproscillaridin in patients with a biliary fistula.
European journal of clinical pharmacology.
1975 Dec; 9(2-3):99-103. doi:
10.1007/bf00614004
. [PMID: 1233271] - K E Andersson, A Bertler, A Redfors. On the pharmacokinetics of proscillaridin A in man.
European journal of clinical pharmacology.
1975 Aug; 8(6):421-5. doi:
10.1007/bf00562316
. [PMID: 1233243] - N Rietbrock, R Staud. Metabolism and excretion of methylproscillaridin by man.
European journal of clinical pharmacology.
1975 Aug; 8(6):427-32. doi:
10.1007/bf00562317
. [PMID: 1233244] - G G Belz, H Nübling, M Strauch. [Effect and plasma level of methylproscillaridin and beta-acetyldigitoxin following long term administration in man].
Verhandlungen der Deutschen Gesellschaft fur Kreislaufforschung.
1975; 41(?):315-9. doi:
NULL
. [PMID: 821263] - H Nishida. [Studies on direct effects of proscillaridin A on the electrolyte excretion and transport ATPase in dog kidneys (author's transl)].
[Hokkaido igaku zasshi] The Hokkaido journal of medical science.
1974 Jul; 49(4):302-6. doi:
. [PMID: 4281758]