Chelidonin (BioDeep_00000374167)

Main id: BioDeep_00000003017

 

PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


Chelidonine

化学式: C20H19NO5 (353.1263)
中文名称: 白屈菜宁
谱图信息: 最多检出来源 () 0%

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/t14-,18-,19+/m0/s1

描述信息

Annotation level-1
http://casmi-contest.org/examples.shtml; CASMI2012 Example 1
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.627
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.621
Acquisition and generation of the data is financially supported by the Max-Planck-Society
IPB_RECORD: 2461; CONFIDENCE confident structure
IPB_RECORD: 921; CONFIDENCE confident structure
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

3 个代谢物同义名

Chelidonine; Chelidonin; Chelidonine



数据库引用编号

25 个数据库交叉引用编号

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)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 16 ABCB1, AIMP2, ANXA5, BCL2, BCL2L1, BIRC5, CASP3, CASP8, CASP9, CAT, CCNB1, PLK1, PTGS2, RELA, STAT3, TUBB4B
Peripheral membrane protein 4 ACHE, ANXA5, CYP1B1, PTGS2
Endoplasmic reticulum membrane 3 BCL2, CYP1B1, PTGS2
Mitochondrion membrane 1 BCL2L1
Nucleus 13 ACHE, AIMP2, BCL2, BIRC5, CASP3, CASP8, CASP9, CCNB1, FOXM1, PLK1, RELA, STAT3, TUBB4B
cytosol 14 AIMP2, ANXA5, BCL2, BCL2L1, BIRC5, CASP3, CASP8, CASP9, CAT, CCNB1, PLK1, RELA, STAT3, TUBB4B
centrosome 3 BCL2L1, CCNB1, PLK1
nucleoplasm 8 BIRC5, CASP3, CASP8, CCNB1, FOXM1, PLK1, RELA, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 3 ABCB1, ACHE, TNF
Cytoplasmic side 1 BCL2L1
lamellipodium 1 CASP8
Multi-pass membrane protein 1 ABCB1
Synapse 1 ACHE
cell surface 3 ABCB1, ACHE, TNF
glutamatergic synapse 2 CASP3, RELA
Golgi apparatus 1 ACHE
mitochondrial inner membrane 1 BCL2L1
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 AIMP2, BCL2L1
plasma membrane 4 ABCB1, ACHE, STAT3, TNF
synaptic vesicle membrane 1 BCL2L1
Membrane 8 ABCB1, ACHE, AIMP2, ANXA5, BCL2, CAT, CCNB1, CYP1B1
apical plasma membrane 1 ABCB1
caveola 1 PTGS2
extracellular exosome 4 ABCB1, ANXA5, CAT, TUBB4B
endoplasmic reticulum 3 BCL2, BCL2L1, PTGS2
extracellular space 2 ACHE, TNF
perinuclear region of cytoplasm 1 ACHE
mitochondrion 6 BCL2, BCL2L1, CASP8, CASP9, CAT, CYP1B1
protein-containing complex 6 BCL2, BIRC5, CASP8, CASP9, CAT, PTGS2
intracellular membrane-bounded organelle 2 CAT, CYP1B1
Microsome membrane 2 CYP1B1, PTGS2
postsynaptic density 1 CASP3
Secreted 1 ACHE
extracellular region 5 ACHE, ANXA5, CAT, TNF, TUBB4B
Mitochondrion outer membrane 2 BCL2, BCL2L1
Single-pass membrane protein 2 BCL2, BCL2L1
mitochondrial outer membrane 3 BCL2, BCL2L1, CASP8
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 3 BCL2L1, CAT, CCNB1
Extracellular side 1 ACHE
transcription regulator complex 2 RELA, STAT3
centriolar satellite 1 PLK1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 BCL2L1, PLK1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 2 BCL2, BCL2L1
nuclear membrane 2 BCL2, BCL2L1
external side of plasma membrane 2 ANXA5, TNF
Extracellular vesicle 1 TUBB4B
microtubule cytoskeleton 3 BIRC5, PLK1, TUBB4B
midbody 2 BIRC5, PLK1
recycling endosome 1 TNF
spindle midzone 1 PLK1
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ABCB1
Cell projection, lamellipodium 1 CASP8
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 TUBB4B
Cytoplasm, cytoskeleton, spindle 2 BIRC5, PLK1
focal adhesion 2 ANXA5, CAT
microtubule 2 BIRC5, TUBB4B
spindle 2 BIRC5, PLK1
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 ANXA5
interphase microtubule organizing center 1 BIRC5
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 4 FOXM1, PLK1, RELA, STAT3
phagocytic cup 1 TNF
mitotic spindle 1 TUBB4B
Chromosome 1 BIRC5
cytoskeleton 2 CASP8, TUBB4B
centriole 2 BIRC5, PLK1
spindle pole 2 CCNB1, PLK1
nuclear chromosome 1 BIRC5
Lipid-anchor, GPI-anchor 1 ACHE
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
Chromosome, centromere 1 BIRC5
Chromosome, centromere, kinetochore 1 BIRC5
axonemal microtubule 1 TUBB4B
cell body 1 CASP8
side of membrane 1 ACHE
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 PTGS2
kinetochore 2 BIRC5, PLK1
mitotic spindle pole 1 PLK1
azurophil granule lumen 1 TUBB4B
apoptosome 1 CASP9
chromosome, centromeric region 1 BIRC5
outer kinetochore 2 CCNB1, PLK1
vesicle membrane 1 ANXA5
chromosome passenger complex 1 BIRC5
cytoplasmic microtubule 1 BIRC5
synaptic cleft 1 ACHE
spindle microtubule 1 BIRC5
survivin complex 1 BIRC5
external side of apical plasma membrane 1 ABCB1
synaptonemal complex 1 PLK1
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
cyclin B1-CDK1 complex 1 CCNB1
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
NF-kappaB p50/p65 complex 1 RELA
[Isoform H]: Cell membrane 1 ACHE
NF-kappaB complex 1 RELA
caspase complex 1 CASP9
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
  • E Ernst, K Schmidt. Ukrain - a new cancer cure? A systematic review of randomised clinical trials. BMC cancer. 2005 Jul; 5(?):69. doi: 10.1186/1471-2407-5-69. [PMID: 15992405]
  • 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]
  • Y Zhang, H Pan, S Chen, Y Meng, S Kang. [Minor alkaloids from the capsule of Papaver nudicaule L]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1997 Sep; 22(9):550-1, 576. doi: ". [PMID: 11038947]
  • J Wolff, L Knipling. Antimicrotubule properties of benzophenanthridine alkaloids. Biochemistry. 1993 Dec; 32(48):13334-9. doi: 10.1021/bi00211a047. [PMID: 7902132]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]