Chemical Property of Chelidonine
Chemical Property:
- Vapor Pressure:4.06E-11mmHg at 25°C
- Melting Point:135-140 °C
- Refractive Index:1.667
- Boiling Point:507.4 °C at 760 mmHg
- PKA:14.11±0.20(Predicted)
- Flash Point:260.7 °C
- PSA：60.39000
- Density:1.422 g/cm3
- LogP:2.26920
- Storage Temp.:2-8°C
- XLogP3:2.2
- Hydrogen Bond Donor Count:1
- Hydrogen Bond Acceptor Count:6
- Rotatable Bond Count:0
- Exact Mass:353.12632271
- Heavy Atom Count:26
- Complexity:560
- Purity/Quality:
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99% *data from raw suppliers
Chelidonine *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xn
- Hazard Codes:Xn
- Statements:
25-20/21/22
- Safety Statements:
20-45-36/37
- MSDS Files:
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Total 1 MSDS from other Authors
Useful:
- Canonical SMILES:CN1CC2=C(C=CC3=C2OCO3)C4C1C5=CC6=C(C=C5CC4O)OCO6
- Isomeric SMILES:CN1CC2=C(C=CC3=C2OCO3)[C@@H]4[C@H]1C5=CC6=C(C=C5C[C@@H]4O)OCO6
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Description
Chelidonine, also named ranunculine, is a benzophenanthridine alkaloid isolated from the whole plant of Chelidonium majus. L. It has been used as a painkiller in clinical treatment based on its morphine-like analgesic effect. Pharmacological researches in recent years have demonstrated that chelidonine played a role in antitumor, antibacterial, spasmolysis activities, and so on. And the antitumor activity is drawing more and more attention. However, its mechanisms of function remain unclear, which needs to be clarified in the future.
Chelidonine is an alkaloid fundamental parent, a benzophenanthridine alkaloid and an alkaloid antibiotic. Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity . Chelidonine is a benzophenanthridine alkaloid that has been isolated from C. majus. It induces Bcl-2- and caspase-dependent apoptosis in HepG2 human liver carcinoma cells with an LC50 value of 12 μM and in Jurkat human T cells when used at a concentration of 1 μM. Chelidonine also downregulates hTERT expression in HepG2 cells, reduces telomerase activity, and induces cell senescence. Chelidonine, also named ranunculine, is a kind of alkaloid isolated from the whole
plant of Chelidonium majus. L . As a kind of traditional Chinese medicine,
Chelidonium majus. L was firstly recorded in Chiu Huang Pen Ts’ao of Ming
dynasty. In the seventeenth century, it has been used for the treatment of jaundice,
biliary colic, and cholelithiasis. In 1941, a researcher from Soviet Union reported
that it showed good effect for the treatment of cutaneous tuberculosis. This plant has
multiple effects on different diseases, including anti-inflammatory, analgesia,
relieving cough, inducing diuresis, anticancer, antifungal, relieving asthma, and
detoxification. It was recorded in the Pharmacopoeia of the People’s Republic of
China (1977) .The material basis for Chelidonium majus. L is alkaloid. Among which, chelidonine,
a benzophenanthridine alkaloid, is the main effective ingredient . Although
great progresses have been made in the chemical synthesis of chelidonine recently,
the biosynthetic pathways of chelidonine remain unclear, which still need in-depth
study and exploration in the future
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Uses
Chelidonine is the major alkaloid component of Chelidonium majus. Chelidonium majus L. is the only species of the tribe Chelidonieae of the Papaveraceae family. The Papaveraceae family is rich in specific alkaloids. C. majus contains various isoquinoline alkaloids with protopine, protoberberine and benzophenanthridine structures. This benzophenanthridine alkaloid can induce apoptosis in some transformed or malignant cell lines. D-Chelidonine, the main alkaloid of Chelidonium majus, was first isolated in 1839.?
Chelidonine is a major bioactive, isoquinoline alkaloid ingredient in Chelidonium majus. Benzylisoquinoline alkaloids (BIAs) are a structurally diverse group of plant specialized metabolites with a long history of investigation. A restricted number of enzyme families have been implicated in BIA metabolism. Whereas some enzymes exhibit a relatively broad substrate range, others are highly substrate specific. A small number of plant species, including opium poppy (Papaver somniferum) and other members of the Ranunculales, have emerged as model systems to study BIA metabolism. Recently, the emergence of transcriptomics, proteomics and metabolomics has expedited the discovery of new BIA biosynthetic genes. Poison; central nervous system depres-
sant causing sleepiness, depression, slowing of the
pulse, coma and circulatory failure.
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Physical properties
Appearance: white crystal or crystalline powder, monoclinic prism crystal.
Solubility: insoluble in water; soluble in ethanol, chloroform, and amyl alcohol.
Melting point: 135–136 °C. Boiling point: 220 °C. Specific optical rotation: +115°.
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Clinical Use
Chelidonine has been used as a painkiller in clinical application due to its significant
analgesic effect. Chelidonine phosphate can be used for treatment of gastrointestinal
and ulcer pain, as a substitute of morphine preparations. Wei Tong Shu capsule
is used to treat pain caused by gastric convulsion, chronic gastritis, gastric ulcer, and
duodenal ulcer. Its main effective compositions are chelidonine and protopine. Fu
Fang Zhong Yao Tong An injection has collateral dredging and analgesic effects and
can be used for the treatment of moderate pain caused by chemoradiotherapy or
non-chemoradiotherapy of gastric cancer, lung cancer, and liver cancer. Its two
main components are chelidonine and sinomenine. Ukrain (NSC-631570), a phosphorothioate
derivative of chelidonine, has been used in clinical treatment as an
effective antitumor drug for the treatment of lung cancer, breast cancer, prostate
cancer, and pancreatic cancer.
