Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H19NO5 |
| Molecular Weight | 353.3686 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CC2=C(C=CC3=C2OCO3)[C@H]4[C@@H](O)CC5=C(C=C6OCOC6=C5)[C@@H]14
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 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line. | 2014-11-05 |
|
| Cytotoxic activity of proteins isolated from extracts of Corydalis cava tubers in human cervical carcinoma HeLa cells. | 2010-12-17 |
|
| [Comparative substrate-inhibitor analysis of liver monoamine oxidases of minks]. | 2010-11-11 |
|
| Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). | 2010-11 |
|
| Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection. | 2010-04 |
|
| Polymorphic nucleic Acid binding of bioactive isoquinoline alkaloids and their role in cancer. | 2010 |
|
| Transcriptional down regulation of hTERT and senescence induction in HepG2 cells by chelidonine. | 2009-08-07 |
|
| A decisive role of mitochondria in defining rate and intensity of apoptosis induction by different alkaloids. | 2008-04-01 |
|
| Apoptogenic activity of two benzophenanthridine alkaloids from Chelidonium majus L. does not correlate with their DNA damaging effects. | 2008-03 |
|
| Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells. | 2008-02 |
|
| Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a Pd II-catalyzed ring-opening strategy. | 2008 |
|
| Ukrain modulates glial fibrillary acidic protein, but not connexin 43 expression, and induces apoptosis in human cultured glioblastoma cells. | 2007-07 |
|
| [Effect of alkaloids from celandine on calcium accumulation and oxidative phosphorylation in mitochondria depending on their DNA intercalating properties]. | 2006-11-15 |
|
| Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006-07-26 |
|
| Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. | 2006-06-08 |
|
| [Experimental study of the inhibitory effects of Chelidonium majus L. extractive on Streptococcus mutans in vitro]. | 2006-06 |
|
| Effect of Ukrain on matrix metalloproteinase-2 and Secreted Protein Acidic and Rich in Cysteine (SPARC) expression in human glioblastoma cells. | 2006-02 |
|
| Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. | 2006-01-17 |
|
| Intestinal spasmolytic effects of STW 5 (Iberogast) and its components. | 2006 |
|
| [Effect of some isoquinoline alkaloids on enzymatic activity of acetylcholinesterase and monoamine oxidase]. | 2005-12-13 |
|
| Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS. | 2005-10-15 |
|
| Ukrain - a new cancer cure? A systematic review of randomised clinical trials. | 2005-07-01 |
|
| Preliminary evaluation of CNS effects of 6-O-substituted chelidonine derivatives. | 2003-09-19 |
|
| Cytotoxic activity and quality control determinations on Chelidonium majus. | 2003-02 |
|
| [Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs]. | 2003 |
|
| 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. | 2002-09 |
|
| [Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood]. | 2002-04-23 |
|
| Effect of a homeopathic drug, Chelidonium, in amelioration of p-DAB induced hepatocarcinogenesis in mice. | 2002-04-10 |
|
| NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial. | 2002-03 |
|
| Synthesis and biological activity of O-acyl and O-alkyl chelidonine derivatives. | 2002-01-05 |
|
| Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain. | 2001-03 |
|
| Synthesis of a [18F]labeled chelidonine derivative as a possible antitumor agent. | 2001-03 |
|
| The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways. | 2001-01 |
|
| [The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives]. | 2001 |
|
| HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products. | 1992-05-29 |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991-01-01 |
|
| Studies on the participation of the dopaminergic system in the central effects of chelidonine. | 1990-09-01 |
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
by
admin
on
Edited
Mon Mar 31 17:46:51 GMT 2025
by
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on
Mon Mar 31 17:46:51 GMT 2025
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| Record UNII |
8K7EK8446J
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| Record Status |
Validated (UNII)
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SUB13313MIG
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100000076349
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207-504-1
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