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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
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

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
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.
1992 May 29
[The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives].
2001
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
Effect of a homeopathic drug, Chelidonium, in amelioration of p-DAB induced hepatocarcinogenesis in mice.
2002 Apr 10
[Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood].
2002 Jan-Feb
NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial.
2002 Mar
[Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs].
2003
Ukrain - a new cancer cure? A systematic review of randomised clinical trials.
2005 Jul 1
[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
Intestinal spasmolytic effects of STW 5 (Iberogast) and its components.
2006
Effect of Ukrain on matrix metalloproteinase-2 and Secreted Protein Acidic and Rich in Cysteine (SPARC) expression in human glioblastoma cells.
2006 Feb
Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway.
2006 Jan 17
Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression.
2006 Jul 26
Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine.
2006 Jun 8
[Effect of alkaloids from celandine on calcium accumulation and oxidative phosphorylation in mitochondria depending on their DNA intercalating properties].
2006 Mar-Apr
Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells.
2008 Feb
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
Name Type Language
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)-REL-
Systematic Name English
CHELIDONINE (±)-FORM [MI]
Common Name English
DIPHYLLINE (ALKALOID)
Common Name English
(±)-CHELIDONINE
Common Name English
Code System Code Type Description
MERCK INDEX
m3322
Created by admin on Sat Dec 16 09:19:31 GMT 2023 , Edited by admin on Sat Dec 16 09:19:31 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
Chelidonine
Created by admin on Sat Dec 16 09:19:31 GMT 2023 , Edited by admin on Sat Dec 16 09:19:31 GMT 2023
PRIMARY
FDA UNII
4UDG3LY0GT
Created by admin on Sat Dec 16 09:19:31 GMT 2023 , Edited by admin on Sat Dec 16 09:19:31 GMT 2023
PRIMARY
CAS
20267-87-2
Created by admin on Sat Dec 16 09:19:31 GMT 2023 , Edited by admin on Sat Dec 16 09:19:31 GMT 2023
PRIMARY
PUBCHEM
197810
Created by admin on Sat Dec 16 09:19:31 GMT 2023 , Edited by admin on Sat Dec 16 09:19:31 GMT 2023
PRIMARY