(+)-Chelidonine
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(+)-Chelidonine
structure -
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CAS No:
476-32-4
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Formula:
C20H19NO5
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Chemical Name:
(+)-Chelidonine
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Synonyms:
[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)-;Chelidonine;[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-(5bα,6β,12bα)]-;(5bR,6S,12bS)-5b,6,7,12b,13,14-Hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol;Stylophorine;[5bR-(5bα,6β,12bα)]-5b,6,7,12b,13,14-Hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol;Chelidonin;(+)-Chelidonine;5907-33-5;10367-14-3;47476-03-9;52503-79-4;855174-41-3
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CAS No:
Description
Chelidonine is an isoquinoline alkaloid isolated from Chelidonium majus L., causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, with anticancer and antiviral activity[1].
Characteristics
60.4
2.75
1.4±0.1 g/cm3
135.5 °C
bp0.002 220° (air-bath temp)
260.7±30.1 °C
1.667
2-8°C
4.06E-11mmHg at 25°C
Subcutaneous-rat LDL0: 300 mg/kg; intravenous-mouse LD50: 35 mg/kg
In case of heat, open flame burning; thermal decomposition to emit toxic nitrogen oxide fumes
D22 +115 ±3° (ethanol); D20 +117° (c = 3 in CHCl3)
Safety Information
2811
3
25-20/21/22
20-45-36/37
FL9450000
Xn
Treasury is low-temperature, ventilated and dry; protected from open flames and high temperatures; stored separately from food materials and oxidants
P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P312, P321, P322, P330, P363, P405, P501
H301
(+)-Chelidonine Use and Manufacturing
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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