Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H19NO5 |
Molecular Weight | 353.3686 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12[C@@H](O)CC3=CC4=C(OCO4)C=C3[C@@]1([H])N(C)CC5=C2C=CC6=C5OCO6
InChI
InChIKey=GHKISGDRQRSCII-ZOCIIQOWSA-N
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
Molecular Formula | C20H19NO5 |
Molecular Weight | 353.3686 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11211931
https://www.ncbi.nlm.nih.gov/pubmed/26626193
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11211931
https://www.ncbi.nlm.nih.gov/pubmed/26626193
Chelidonine is the major alkaloid component of Chelidonium majus. Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase (a nonspecific cholinesterase) inhibitory activity. It showed strong cytotoxicity in cancer cells. While several modes of death have been identified, most of anti-cancer attempts have focused on stimulation of cells to undergo apoptosis. Chelidonine seems to trigger multiple mechanisms in MCF-7 breast cancer cells. It induces both apoptosis and autophagy modes of cell death in a dose dependent manner. Alteration of expression levels of bax/bcl2, and dapk1a by increasing concentration of chelidonine approves switching the death mode from apoptosis induced by very low to autophagy by high concentrations of this compound. On the other hand, submicromolar concentrations of chelidonine strongly suppressed telomerase at both enzyme activity and hTERT transcriptional level. Long exposure of the cells to 50 nanomolar concentration of chelidonine considerably accelerated senescence. Altogether, chelidonine may provide a promising chemistry from nature to treat cancer. Chelidonine exhibits a broad spectrum of pharmacological properties, such as anti-inflammatory and antiviral activities Its biological activities and clinical applications have been extensively investigated. Especially the usage of chelidonine as an anticancer drug is very important lately. It also has profound inhibitory effects on airway inflammation, which means chelidonine can improve allergic asthma in mice and may also work for human medicine.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
34.51 µM [IC50] | |||
Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27420038 |
3.85 µM [IC50] | ||
Target ID: CHEMBL614909 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26677104 |
23.13 µM [IC50] | ||
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213973 |
26.8 µM [IC50] | ||
Target ID: CHEMBL1914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21213973 |
31.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Studies on the participation of the dopaminergic system in the central effects of chelidonine. | 1990 Sep-Oct |
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Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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[The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives]. | 2001 |
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The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways. | 2001 Jan |
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Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain. | 2001 Mar |
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Synthesis of a [18F]labeled chelidonine derivative as a possible antitumor agent. | 2001 Mar |
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Synthesis and biological activity of O-acyl and O-alkyl chelidonine derivatives. | 2001 Nov-Dec |
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Effect of a homeopathic drug, Chelidonium, in amelioration of p-DAB induced hepatocarcinogenesis in mice. | 2002 Apr 10 |
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[Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood]. | 2002 Jan-Feb |
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NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial. | 2002 Mar |
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Preliminary evaluation of CNS effects of 6-O-substituted chelidonine derivatives. | 2003 Mar-Apr |
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Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS. | 2005 Sep-Oct |
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Effect of Ukrain on matrix metalloproteinase-2 and Secreted Protein Acidic and Rich in Cysteine (SPARC) expression in human glioblastoma cells. | 2006 Feb |
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Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. | 2006 Jun 8 |
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Ukrain modulates glial fibrillary acidic protein, but not connexin 43 expression, and induces apoptosis in human cultured glioblastoma cells. | 2007 Jul |
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Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a Pd II-catalyzed ring-opening strategy. | 2008 |
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A decisive role of mitochondria in defining rate and intensity of apoptosis induction by different alkaloids. | 2008 Apr 1 |
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Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells. | 2008 Feb |
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Apoptogenic activity of two benzophenanthridine alkaloids from Chelidonium majus L. does not correlate with their DNA damaging effects. | 2008 Mar |
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Polymorphic nucleic Acid binding of bioactive isoquinoline alkaloids and their role in cancer. | 2010 |
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Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection. | 2010 Apr |
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Cytotoxic activity of proteins isolated from extracts of Corydalis cava tubers in human cervical carcinoma HeLa cells. | 2010 Dec 17 |
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Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). | 2010 Nov |
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[Comparative substrate-inhibitor analysis of liver monoamine oxidases of minks]. | 2010 Sep-Oct |
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Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line. | 2014 Nov 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23850776
Mice: mice were fed once/day for 14 consecutive days of the experimental period, respectively, with 50 mg/kg, 75 mg/kg and 100 mg/kg body weight (bw) of chelidonine dissolved in sterile saline.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27420038
2.5 uM chelidonine arrested the cell cycle in the G2/M
phase with an increase from 25.67% to 88.27% in HeLa cells
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 09:19:31 GMT 2023
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admin
on
Sat Dec 16 09:19:31 GMT 2023
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Record UNII |
4UDG3LY0GT
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Record Status |
Validated (UNII)
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Record Version |
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m3322
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Chelidonine
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4UDG3LY0GT
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20267-87-2
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197810
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