Chelidonine (BioDeep_00000003017)

 

Secondary id: BioDeep_00000374167

natural product PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol

化学式: C20H19NO5 (353.12631640000006)
中文名称: 白屈菜碱, 白屈菜宁
谱图信息: 最多检出来源 Viridiplantae(plant) 9.38%

分子结构信息

SMILES: CN1CC2=C(C=CC3=C2OCO3)C4C1C5=CC6=C(C=C5CC4O)OCO6
InChI: InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3

描述信息

Chelidonine is an alkaloid fundamental parent, a benzophenanthridine alkaloid and an alkaloid antibiotic.
Chelidonine is a natural product found in Sarcocapnos baetica, Sarcocapnos saetabensis, and other organisms with data available.
Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.
See also: Chelidonium majus flowering top (part of).
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2255
Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity[1][2][3].
Chelidonine, an isoquinoline alkaloid, can be isolated from Chelidonium majus L.. Chelidonine causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, and prevents cell cycle progression of stem cells in Dugesia japonica. Chelidonine has cytotoxic activity against melanoma cell lines. with anticancer and antiviral activity[1][2][3].

同义名列表

49 个代谢物同义名

(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol; (5BR-(5B.ALPHA.,6.BETA.,12B.ALPHA.))-5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL(1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL; (5BR-(5Balpha,6beta,12Balpha))-5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL(1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL; Rel-(5bR,6R,12bS)-13-methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4,5:4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol; (5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro-[1,3]dioxolo[4,5:4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol; (1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL, 5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL-, (5BR,6S,12BS)-REL-; [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-rel-; (1,3)BENZODIOXOLO(5,6-C)-1,3-DIOXOLO(4,5-I)PHENANTHRIDIN-6-OL, 5B,6,7,12B,13,14-HEXAHYDRO-13-METHYL-, (5BR,6S,12BS)-; [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-; 5b,6,7,12b,13,14-Hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenan-thridin-6-ol; Chelidonine ((+)-Chelidonine); Chelidonine, >=97.0\\% (HPLC); GHKISGDRQRSCII-ZOCIIQOWSA-N; CHELIDONINE (+/-)-FORM [MI]; chelidonine hydrochloride; CHELIDONINE (+)-FORM [MI]; DIPHYLLINE (ALKALOID); chelidonine bisulfate; chelidonine tartrate; CHELIDONINE (+)-FORM; Chelidoniny [Polish]; CHELIDONINE [WHO-DD]; chelidonine sulfate; Chelidonin [German]; CHELIDONINE, (+/-)-; CHELIDONINE [INCI]; Prestwick1_000587; Chelidonine (+-)-; Prestwick0_000587; Prestwick2_000587; Prestwick3_000587; (+/-)-chelidonine; CHELIDONINE (+); (1)-Chelidonine; UNII-8K7EK8446J; (+)-Chelidonine; UNII-4UDG3LY0GT; MEGxp0_001421; BPBio1_000478; Stylophorine; ACon1_000007; Stylophorin; Chelidonine; Chelidoniny; 8K7EK8446J; Khelidonin; 4UDG3LY0GT; Helidonine; Chelidonin



数据库引用编号

58 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

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

  • Sneha Singh, Nandini Pathak, Eram Fatima, Arvind Singh Negi. Plant isoquinoline alkaloids: Advances in the chemistry and biology of berberine. European journal of medicinal chemistry. 2021 Dec; 226(?):113839. doi: 10.1016/j.ejmech.2021.113839. [PMID: 34536668]
  • Ling Qian, Kun Chen, Changhong Wang, Zhen Chen, Zhiqiang Meng, Peng Wang. Targeting NRAS-Mutant Cancers with the Selective STK19 Kinase Inhibitor Chelidonine. Clinical cancer research : an official journal of the American Association for Cancer Research. 2020 07; 26(13):3408-3419. doi: 10.1158/1078-0432.ccr-19-2604. [PMID: 32156748]
  • Zhong-Min Zhao, Xiao-Fei Shang, Raymond Kobla Lawoe, Ying-Qian Liu, Rui Zhou, Yu Sun, Yin-Fang Yan, Jun-Cai Li, Guan-Zhou Yang, Cheng-Jie Yang. Anti-phytopathogenic activity and the possible mechanisms of action of isoquinoline alkaloid sanguinarine. Pesticide biochemistry and physiology. 2019 Sep; 159(?):51-58. doi: 10.1016/j.pestbp.2019.05.015. [PMID: 31400784]
  • Thomas Kopp, Mona Abdel-Tawab, Martin Khoeiklang, Boris Mizaikoff. Development of a Selective Adsorbing Material for Binding of Pyrrolizidine Alkaloids in Herbal Extracts, Based on Molecular Group Imprinting. Planta medica. 2019 Sep; 85(13):1107-1113. doi: 10.1055/a-0961-2658. [PMID: 31382302]
  • Yuyang Liu, Ying Peng, Zhengyu Zhang, Xiucai Guo, Mingshan Ji, Jiang Zheng. In vitro and in vivo studies of the metabolic activation of chelidonine. Chemico-biological interactions. 2019 Aug; 308(?):155-163. doi: 10.1016/j.cbi.2019.05.012. [PMID: 31102647]
  • Cuiting Wu, Xin Wang, Ming Xu, Youping Liu, Xin Di. Intracellular Accumulation as an Indicator of Cytotoxicity to Screen Hepatotoxic Components of Chelidonium majus L. by LC-MS/MS. Molecules (Basel, Switzerland). 2019 Jun; 24(13):. doi: 10.3390/molecules24132410. [PMID: 31261913]
  • Yuyang Liu, Tiantian Cui, Ying Peng, Mingshan Ji, Jiang Zheng. Mechanism-based inactivation of cytochrome P450 2D6 by chelidonine. Journal of biochemical and molecular toxicology. 2019 Feb; 33(2):e22251. doi: 10.1002/jbt.22251. [PMID: 30368994]
  • Jialiang Pan, Yang Yang, Rui Zhang, Hanwen Yao, Kangkang Ge, Manyin Zhang, Ling Ma. Enrichment of chelidonine from Chelidonium majus L. using macroporous resin and its antifungal activity. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Dec; 1070(?):7-14. doi: 10.1016/j.jchromb.2017.10.029. [PMID: 29102247]
  • Rica Capistrano I, An Wouters, Filip Lardon, Claudia Gravekamp, Sandra Apers, Luc Pieters. In vitro and in vivo investigations on the antitumour activity of Chelidonium majus. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 Dec; 22(14):1279-87. doi: 10.1016/j.phymed.2015.10.013. [PMID: 26626193]
  • Okhwa Kim, Cheol Hwangbo, Junhyeong Kim, Dong-Hao Li, Byung-Sun Min, Jeong-Hyung Lee. Chelidonine suppresses migration and invasion of MDA-MB-231 cells by inhibiting formation of the integrin-linked kinase/PINCH/α-parvin complex. Molecular medicine reports. 2015 Aug; 12(2):2161-8. doi: 10.3892/mmr.2015.3621. [PMID: 25890994]
  • Avijit Paul, Jayeeta Das, Sreemanti Das, Asmita Samadder, Anisur Rahman Khuda-Bukhsh. Poly (lactide-co-glycolide) nano-encapsulation of chelidonine, an active bioingredient of greater celandine (Chelidonium majus), enhances its ameliorative potential against cadmium induced oxidative stress and hepatic injury in mice. Environmental toxicology and pharmacology. 2013 Nov; 36(3):937-47. doi: 10.1016/j.etap.2013.08.008. [PMID: 24035924]
  • A D Bozhadze, V Iu Vachnadze, M S Dzhokhadze, D T Berashvili, A Dzh Bakuridze. [Study on the separation process of pharmacological active total alkaloids from Chelidonium majus L. growing in Georgia]. Georgian medical news. 2013 Apr; ?(217):61-5. doi: . [PMID: 23676491]
  • Mahmoud Zaki El-Readi, SafaaYehia Eid, Mohamed Lotfy Ashour, Ahmad Tahrani, Michael Wink. Modulation of multidrug resistance in cancer cells by chelidonine and Chelidonium majus alkaloids. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Feb; 20(3-4):282-94. doi: 10.1016/j.phymed.2012.11.005. [PMID: 23238299]
  • Khaled M M Koriem, Mahmoud S Arbid, Gihan F Asaad. Chelidonium majus leaves methanol extract and its chelidonine alkaloid ingredient reduce cadmium-induced nephrotoxicity in rats. Journal of natural medicines. 2013 Jan; 67(1):159-67. doi: 10.1007/s11418-012-0667-6. [PMID: 22484604]
  • Ji Eun Park, To Dao Cuong, Tran Manh Hung, IkSoo Lee, MinKyun Na, Jin Cheol Kim, SungWoo Ryoo, Jeong Hyung Lee, Jae Sue Choi, Mi Hee Woo, Byung Sun Min. Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells. Bioorganic & medicinal chemistry letters. 2011 Dec; 21(23):6960-3. doi: 10.1016/j.bmcl.2011.09.128. [PMID: 22024033]
  • Jia-Yun Yao, Zhi-Ming Zhou, Xiao-yi Pan, Gui-jie Hao, Xi-Lian Li, Yang Xu, Jin-Yu Shen, Hong-shun Ru, Wen-lin Yin. In vivo anthelmintic activity of chelidonine from Chelidonium majus L. against Dactylogyrus intermedius in Carassius auratus. Parasitology research. 2011 Nov; 109(5):1465-9. doi: 10.1007/s00436-011-2416-2. [PMID: 21537985]
  • Maria Kulp, Olga Bragina, Priit Kogerman, Mihkel Kaljurand. Capillary electrophoresis with LED-induced native fluorescence detection for determination of isoquinoline alkaloids and their cytotoxicity in extracts of Chelidonium majus L. Journal of chromatography. A. 2011 Aug; 1218(31):5298-304. doi: 10.1016/j.chroma.2011.06.016. [PMID: 21726876]
  • Joabe Gomes de Melo, Ariane Gaspar Santos, Elba Lúcia Cavalcanti de Amorim, Silene Carneiro do Nascimento, Ulysses Paulino de Albuquerque. Medicinal plants used as antitumor agents in Brazil: an ethnobotanical approach. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):365359. doi: 10.1155/2011/365359. [PMID: 21528006]
  • Robert Nawrot, Maria Wolun-Cholewa, Wojciech Bialas, Danuta Wyrzykowska, Stanislaw Balcerkiewicz, Anna Gozdzicka-Jozefiak. Cytotoxic activity of proteins isolated from extracts of Corydalis cava tubers in human cervical carcinoma HeLa cells. BMC complementary and alternative medicine. 2010 Dec; 10(?):78. doi: 10.1186/1472-6882-10-78. [PMID: 21167042]
  • Lucie Cahlíková, Lubomír Opletal, Milan Kurfürst, Katerina Macáková, Andrea Kulhánková, Anna Hostálková. Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). Natural product communications. 2010 Nov; 5(11):1751-4. doi: . [PMID: 21213973]
  • Motilal Maiti, Gopinatha Suresh Kumar. Polymorphic nucleic Acid binding of bioactive isoquinoline alkaloids and their role in cancer. Journal of nucleic acids. 2010; 2010(?):. doi: 10.4061/2010/593408. [PMID: 20814427]
  • Vitaliy Kaminskyy, Kah-Wai Lin, Yevhen Filyak, Rostyslav Stoika. Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells. Cell biology international. 2008 Feb; 32(2):271-7. doi: 10.1016/j.cellbi.2007.09.004. [PMID: 18029203]
  • Rui-bo Cheng, Xu Chen, Shu-jie Liu, Xiao-fang Zhang, Guang-he Zhang. [Experimental study of the inhibitory effects of Chelidonium majus L. extractive on Streptococcus mutans in vitro]. Shanghai kou qiang yi xue = Shanghai journal of stomatology. 2006 Jun; 15(3):318-20. doi: ". [PMID: 16862371]
  • H Heinle, D Hagelauer, U Pascht, O Kelber, D Weiser. Intestinal spasmolytic effects of STW 5 (Iberogast) and its components. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2006; 13 Suppl 5(?):75-9. doi: 10.1016/j.phymed.2006.03.013. [PMID: 16709451]
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  • H Saglam, G Arar. Cytotoxic activity and quality control determinations on Chelidonium majus. Fitoterapia. 2003 Feb; 74(1-2):127-9. doi: 10.1016/s0367-326x(02)00312-x. [PMID: 12628406]
  • Catherina Caballero-George, Patrick M L Vanderheyden, Sandra Apers, Hilde Van den Heuvel, Pablo N Solis, Mahabir P Gupta, Magda Claeys, Luc Pieters, Georges Vauquelin, Arnold J Vlietinck. Inhibitory activity on binding of specific ligands to the human angiotensin II AT(1) and endothelin 1 ET(A) receptors: bioactive benzo[c]phenanthridine alkaloids from the root of Bocconia frutescens. Planta medica. 2002 Sep; 68(9):770-5. doi: 10.1055/s-2002-34406. [PMID: 12357384]
  • Surjyo Jyoti Biswas, Anisur Rahman Khuda-Bukhsh. Effect of a homeopathic drug, Chelidonium, in amelioration of p-DAB induced hepatocarcinogenesis in mice. BMC complementary and alternative medicine. 2002 Apr; 2(?):4. doi: 10.1186/1472-6882-2-4. [PMID: 11943072]
  • Frank Gansauge, Marco Ramadani, Jochen Pressmar, Susanne Gansauge, Bernd Muehling, Kerstin Stecker, Gregor Cammerer, Gerd Leder, Hans G Beger. NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial. Langenbeck's archives of surgery. 2002 Mar; 386(8):570-4. doi: 10.1007/s00423-001-0267-5. [PMID: 11914932]
  • A Panzer, A M Joubert, P C Bianchi, E Hamel, J C Seegers. The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways. European journal of cell biology. 2001 Jan; 80(1):111-8. doi: 10.1078/0171-9335-00135. [PMID: 11211931]
  • K O Hiller, M Ghorbani, H Schilcher. Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum. Planta medica. 1998 Dec; 64(8):758-60. doi: 10.1055/s-2006-957576. [PMID: 9933996]
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