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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
Structure of CHELIDONINE

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

HIDE SMILES / InChI

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

Description
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.

Originator

Curator's Comment: First isolation of chelidonine, a partially hydrogenated base, from Papaveraceous plant, was reported in 1839

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives].
2001
The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways.
2001 Jan
Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain.
2001 Mar
Synthesis of a [18F]labeled chelidonine derivative as a possible antitumor agent.
2001 Mar
Synthesis and biological activity of O-acyl and O-alkyl chelidonine derivatives.
2001 Nov-Dec
[Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood].
2002 Jan-Feb
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 Sep
[Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs].
2003
Preliminary evaluation of CNS effects of 6-O-substituted chelidonine derivatives.
2003 Mar-Apr
[Effect of some isoquinoline alkaloids on enzymatic activity of acetylcholinesterase and monoamine oxidase].
2005 Mar-Apr
Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS.
2005 Sep-Oct
Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway.
2006 Jan 17
[Experimental study of the inhibitory effects of Chelidonium majus L. extractive on Streptococcus mutans in vitro].
2006 Jun
Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine.
2006 Jun 8
Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a Pd II-catalyzed ring-opening strategy.
2008
Transcriptional down regulation of hTERT and senescence induction in HepG2 cells by chelidonine.
2009 Aug 7
Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection.
2010 Apr
Cytotoxic activity of proteins isolated from extracts of Corydalis cava tubers in human cervical carcinoma HeLa cells.
2010 Dec 17
Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae).
2010 Nov
[Comparative substrate-inhibitor analysis of liver monoamine oxidases of minks].
2010 Sep-Oct
Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line.
2014 Nov 5
Patents

Sample Use Guides

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
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 Fri Dec 15 15:06:44 GMT 2023
Edited
by admin
on Fri Dec 15 15:06:44 GMT 2023
Record UNII
8K7EK8446J
Record Status Validated (UNII)
Record Version
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Name Type Language
CHELIDONINE
INCI   WHO-DD  
INCI  
Official Name English
CHELIDONINE (+)-FORM [MI]
Common Name English
CHELIDONINE (+)-FORM
MI  
Common Name English
CHELIDONIN
Common Name English
(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
Common Name English
CHELIDONINE [INCI]
Common Name English
STYLOPHORINE
Common Name English
STYLOPHORIN
Common Name English
(+)-CHELIDONINE
Common Name English
(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)-
Systematic Name English
Chelidonine [WHO-DD]
Common Name English
Code System Code Type Description
EVMPD
SUB13313MIG
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
SMS_ID
100000076349
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID10878474
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
MERCK INDEX
m3322
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY Merck Index
MESH
C062047
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
CAS
476-32-4
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
CHEBI
31389
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
FDA UNII
8K7EK8446J
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
PUBCHEM
197810
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-504-1
Created by admin on Fri Dec 15 15:06:44 GMT 2023 , Edited by admin on Fri Dec 15 15:06:44 GMT 2023
PRIMARY
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