Chelidonin

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CHELIDONINE Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R25:Giftig beim Verschlucken.
  R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

• S-Sätze Betriebsanweisung:

  S20:Bei der Arbeit nicht essen und trinken.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
  S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.

• Beschreibung

  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

• Beschreibung

  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.

• Chemische Eigenschaften

  White, crystalline powder alkaloid.

• Physikalische Eigenschaften

  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°.

• History

  Chelidonine was isolated from Chelidonium majus. L in 1824 for the first time. Pharmacological studies found that it exerted antitumor effect via different mechanisms. However, its poor bioavailability limited its application. Some researchers developed a chelidonine/polylactic acid copolymer nanoparticle using nanotechnology. The nano-chelidonine showed good tissue distribution without causing any toxicity in mice and could enter into the brain tissues, showing great application potential. In addition, nano-chelidonine showed protective effect on liver injury induced by cadmium in mice .
  In 1981, an Austrian researcher isolated a novel compound ukrain (phosphorothioate derivative of chelidonine) from Chelidonium majus. L. Ukrain could inhibit tumor cell proliferation through a variety of mechanisms. Currently, ukrain is used as an antitumor drug for the clinical treatment of lung cancer, breast cancer, prostate cancer, and pancreatic cancer . In 2004, quarter amine chelidonine phosphorothioate derivatives have been applied for an invention patent as anticancer drugs in China.
  Chelidonine has morphine-like analgesic effects suggesting that its analgesic effect is mainly peripheral and cannot be antagonized by the morphine receptor antagonist naloxone . The 6-alkoxy and 6-acyloxy derivatives of chelidonine can inhibit the central nervous system, especially for nerve terminal, and show sedative and hypnotic effects .

• Verwenden

  Poison; central nervous system depres- sant causing sleepiness, depression, slowing of the pulse, coma and circulatory failure.

• Definition

  ChEBI: Chelidonine is an alkaloid fundamental parent, a benzophenanthridine alkaloid and an alkaloid antibiotic.

• Biochem/physiol Actions

  Inhibits tubulin polymerisation (IC50=24 μM), thereby disrupting microtubule structure in cells and inducing a G2/M mitotic arrest.

• Pharmakologie

  Chelidonine has a variety of pharmacological effects, mainly manifested in the following aspects:
  1. The effect on nervous system (analgesia, sedation)
  Chelidonine, as a protopine, has analgesia effect similar to that of morphine. After intragastric administration (5–20 mg/kg) to mice, it showed a dose-dependent analgesic effect, which could sustain 4–48 h . Chelidonine derivatives also have sedative and hypnotic effects .
  2. The effect on cardiovascular systemChelidonine has many effects on cardiovascular system, including exciting heart, expanding coronary blood vessels, and increasing blood pressure. Chelidonine (0.01–0.02 mg) leads to the excitement of frog heart in vitro, as well as slowdown of heart beat. Higher dosage (0.05 mg) of chelidonine could cause arrhythmia and diastolic cardiac arrest .
  3. The antitumor effect
  Chelidonine is a toxic substance that can influence mitosis. In vitro studies have shown that chelidonine had significant inhibitory effects for gastric cancer, leukemia, nasopharyngeal carcinoma, and hepatoma carcinoma cells. It also could delay the growth of malignant tumors. Its antitumor effects were mediated by different mechanisms, which still need further studies .
  4. The effect on smooth muscle
  Chelidonine has spasmolytic and diastolic effects and can inhibit a variety of smooth muscle spasm. Obvious spasmolytic effects for gastrointestinal tract and bronchial and urinary system have been reported .
  5. The antibacterial effect
  Chelidonine has antibacterial effect. It inhibits Mycobacterium tuberculosis in vivo and inhibits alpha Streptococcus, Diplococcus pneumoniae, and other gram-positive bacteria in vitro. In addition, chelidonine also shows inhibitory effect on Kauffman-Wolf Trichophyta and Epidermophyton floccosum .
  6. Other pharmacological effects
  Chelidonine showed protective effects on cadmium chloride-induced liver and kidney toxicity in rats. Chelidonine can inhibit the growth of human keratinocytes. Guinea pig test confirmed that chelidonine (4–10 mg/kg) could prevent or delay the anaphylactic shock. In addition, chelidonine has anti-mite effect and good synergistic effect with trichlorfon or omethoate to prevent cotton bollworm.

• 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.

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