A tertiary hexahydro-benzophenanthridine alkaloid
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Chelidonine

Item No. 25097

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5bR,6S,7,12bS,13,14-hexahydro-13-methyl-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol
CAS Number
476-32-4
Molecular Formula
C20H19NO5
Formula Weight
353.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
241, 290 nm
SMILES
CN1CC2=C(C=CC3=C2OCO3)[C@@]4([H])[C@@H](O)CC5=CC6=C(OCO6)C=C5[C@]41[H]
InChi Code
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
InChi Key
GHKISGDRQRSCII-ZOCIIQOWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

    $523

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    Cayman Chemical
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    Product Description

    Chelidonine is a benzophenanthridine alkaloid that has been isolated from C. majus.1,2 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.1,3 Chelidonine also downregulates hTERT expression in HepG2 cells, reduces telomerase activity, and induces cell senescence.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Noureini, S.K., and Wink, M. Transcriptional down regulation of hTERT and senescence induction in HepG2 cells by chelidonine. World J. Gastroenterol. 15(29), 3603-3610 (2009).

    2. Och, A., Szewczyk, K., Pecio, Ł., et al. UPLC-MS/MS profile of alkaloids with cytotoxic properties of selected medicinal plants of the Berberidaceae and Papaveraceae families. Oxid. Med. Cell. Longev. 2017:9369872, (2017).

    3. Habermehl, D., Kammerer, B., Handrick, R., et al. Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway. BMC Cancer 6:14, (2006).