chelidonine

[5bR-(5ba,6b,12b4a)]-5b,6,7,12b,13,14-hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-di oxolo[4,5-i]phenanthridin-6-ol

CAS: 476-32-4 C20 H19 N O5 MW: 353.37443000

Identification

Namechelidonine
CAS Number476-32-4
EINECS207-504-1
FDA UNII8K7EK8446J
Molecular FormulaC20 H19 N O5
Molecular Weight353.37443000
MDL NumberMFCD00069660
Nikkaji NumberJ5.974I
Beilstein4275089

Regulatory

Physical Properties

Appearance chocolate brown powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 135.50 °C. @ 760.00 mm Hg
Boiling Point 507.39 °C. @ 760.00 mm Hg (est)
Flash Point 501.00 °F. TCC ( 260.70 °C. ) (est)
logP (o/w) 2.899 (est)
Soluble in water, 196.4 mg/L @ 25 °C (est)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesskin conditioning

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintravenous-mouse LD50 35 mg/kg
Dermal Toxicitysubcutaneous-cat LD50 140 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic agents
Recommendation for chelidonine usage levels up tonot for fragrance use.
Recommendation for chelidonine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

found in nature

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)- chelidonin helidonine [5bR-(5ba,6b,12b4a)]-5b,6,7,12b,13,14- hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-di oxolo[4,5-i]phenanthridin-6-ol khelidonin (5bR,6S,12bS)-13- methyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol (5bR,6S,12bS)-13- methyl-5b,6,7,12b,13,14-hexahydro[1,3]dioxolo[4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol stylophorin stylophorine (1S,12S,13R)-24- methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol PubMed: Poly (lactide-co-glycolide) nano-encapsulation of chelidonine, an active bioingredient of greater celandine (Chelidonium majus), enhances its ameliorative potential against cadmium induced oxidative stress and hepatic injury in mice. PubMed: Cytotoxicity and apoptotic signalling cascade induced by chelidonine-loaded PLGA nanoparticles in HepG2 cells in vitro and bioavailability of nano-chelidonine in mice in vivo. PubMed: [The reactivity of liver monoamine oxidase in the ringed seal Phoca hispida ladogensis]. PubMed: [Study on the separation process of pharmacological active total alkaloids from Chelidonium majus L. growing in Georgia]. PubMed: Capillary electrophoretic study of the synergistic biological effects of alkaloids from Chelidonium majus L. in normal and cancer cells. PubMed: A sensitive and selective liquid chromatography-tandem mass spectrometry method for simultaneous determination of five isoquinoline alkaloids from Chelidonium majus L. in rat plasma and its application to a pharmacokinetic study. PubMed: Modulation of multidrug resistance in cancer cells by chelidonine and Chelidonium majus alkaloids. PubMed: Chelidonine isolated from ethanolic extract of Chelidonium majus promotes apoptosis in HeLa cells through p38-p53 and PI3K/AKT signalling pathways. PubMed: Total syntheses of chelidonine and norchelidonine via an enamide-benzyne-[2 + 2] cycloaddition cascade. PubMed: The in vivo effect of chelidonine on the stem cell system of planarians. PubMed: Chelidonium majus leaves methanol extract and its chelidonine alkaloid ingredient reduce cadmium-induced nephrotoxicity in rats. PubMed: Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells. PubMed: Capillary electrophoresis with LED-induced native fluorescence detection for determination of isoquinoline alkaloids and their cytotoxicity in extracts of Chelidonium majus L. PubMed: In vivo anthelmintic activity of chelidonine from Chelidonium majus L. against Dactylogyrus intermedius in Carassius auratus. PubMed: Benzo[c]phenanthridine alkaloids exhibit strong anti-proliferative activity in malignant melanoma cells regardless of their p53 status. PubMed: Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Chelidonium majus (Papaveraceae). PubMed: [Comparative substrate-inhibitor analysis of liver monoamine oxidases of minks]. PubMed: Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection. PubMed: Transcriptional down regulation of hTERT and senescence induction in HepG2 cells by chelidonine. PubMed: A decisive role of mitochondria in defining rate and intensity of apoptosis induction by different alkaloids. PubMed: Concise enantioselective total syntheses of (+)-homochelidonine, (+)-chelamidine, (+)-chelidonine, (+)-chelamine and (+)-norchelidonine by a Pd II-catalyzed ring-opening strategy. PubMed: Differential effect of sanguinarine, chelerythrine and chelidonine on DNA damage and cell viability in primary mouse spleen cells and mouse leukemic cells. PubMed: Apoptogenic activity of two benzophenanthridine alkaloids from Chelidonium majus L. does not correlate with their DNA damaging effects. PubMed: Ukrain modulates glial fibrillary acidic protein, but not connexin 43 expression, and induces apoptosis in human cultured glioblastoma cells. PubMed: [Effect of alkaloids from celandine on calcium accumulation and oxidative phosphorylation in mitochondria depending on their DNA intercalating properties]. PubMed: [Experimental study of the inhibitory effects of Chelidonium majus L. extractive on Streptococcus mutans in vitro]. PubMed: Intestinal spasmolytic effects of STW 5 (Iberogast) and its components. PubMed: Effect of Ukrain on matrix metalloproteinase-2 and Secreted Protein Acidic and Rich in Cysteine (SPARC) expression in human glioblastoma cells. PubMed: Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. PubMed: [Effect of some isoquinoline alkaloids on enzymatic activity of acetylcholinesterase and monoamine oxidase]. PubMed: Identification and quantification of isoquinoline alkaloids in the genus Sarcocapnos by GC-MS. PubMed: Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. PubMed: [Inhibition of liver mitochondrial monoamine oxidase activity by alkaloids isolated from Chelidonium and Macleaya and by their derivative drugs]. PubMed: Preliminary evaluation of CNS effects of 6-O-substituted chelidonine derivatives. PubMed: Cytotoxic activity and quality control determinations on Chelidonium majus. PubMed: 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. PubMed: [Inhibition by various alkaloids of acetylcholinesterase and butyrylcholinesterase from human blood]. PubMed: NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial. PubMed: [The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives]. PubMed: Synthesis and biological activity of O-acyl and O-alkyl chelidonine derivatives. PubMed: A method for determination of Ukrain in blood plasma for monitoring and pharmacokinetic study. PubMed: Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain. PubMed: Synthesis of a [18F]labeled chelidonine derivative as a possible antitumor agent. PubMed: The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways. PubMed: Chemical analyses of Ukrain, a semi-synthetic Chelidonium majus alkaloid derivative, fail to confirm its trimeric structure. PubMed: [Minor alkaloids from the capsule of Papaver nudicaule L]. PubMed: Effect of sample handling on alkaloid and mineral content of aqueous extracts of greater celandine (Chelidonium majus L.). PubMed: Inhibition of Candida rugosa lipase by berberine and structurally related alkaloids, evaluated by high-performance liquid chromatography. PubMed: Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pig ileum. PubMed: Benzophenanthridine alkaloids of Chelidonium majus; II. Potent inhibitory action against the growth of human keratinocytes. PubMed: Benzophenanthridine alkaloids of Chelidonium majus; I. Inhibition of 5- and 12-lipoxygenase by a non-redox mechanism. PubMed: Pharmacological activities of Chelidonium majus L. (Papaveraceae). PubMed: Ukrain therapy in a frontal anaplastic grade III astrocytoma (case report). PubMed: [The greater celandine (Chelidonium majus L.)--review of present knowledge]. PubMed: Antimicrotubule properties of benzophenanthridine alkaloids. PubMed: [HPTLC separation and fluorodensitometric determination of isoquinoline alkaloids in Chelidonine majus L]. PubMed: Chelidonium majus L. (Ukrain) in the treatment of cancer patients. PubMed: Stepwise gradient in thin-layer chromatography of Chelidonium alkaloids. PubMed: Studies on the participation of the dopaminergic system in the central effects of chelidonine. PubMed: Preliminary pharmacological evaluation of chelidonine in rodents. PubMed: Separation and Quantification of Some Alkaloids from Fumaria parviflora by Capillary Isotachophoresis1. PubMed: [Basic electron optical characteristics of chelidonine hydrochloride]. PubMed: THE ANTITUMOR FACTORS PRESENT IN CHELIDONIUM MAJUS L. I. CHELIDONINE AND PROTOPINE. PubMed: [Partition of chelidonine and protopine by means of countercurrent cascade extraction]. PubMed: [On the pharmacology of chelidonine and sanguinarine]. PubMed: [Recent data on the pharmacology of chelidonine and sanguinarine]. PubMed: [The configurations of chelidonine and homchelidonine]. PubMed: Separation and determination of the dissociation constants of chelidonine and protopine by paper chromatography. PubMed: [Chelidonine in liver and gallbladder diseases]. PubMed: [Studies on paper electrophoresis; paper electrophoresis of morphine and chelidonine in natural mixtures].