An aporphine alkaloid with diverse biological activities
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Crebanine

Item No. 36176

Technical Information
Formal Name
(7R)-6,7,7a,8-tetrahydro-9,10-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline
CAS Number
25127-29-1
Synonyms
  • (–)-Crebanine
Molecular Formula
C20H21NO4
Formula Weight
Purity
≥98%
A solid
DMF: 12 mg/mlDMSO: 10 mg/mlEthanol: Slightly soluble
λmax
217, 280 nm
SMILES
CN1[C@@]2([H])C3=C(CC1)C=C(OCO4)C4=C3C5=CC=C(OC)C(OC)=C5C2
InChi Code
InChI=1S/C20H21NO4/c1-21-7-6-11-8-16-20(25-10-24-16)18-12-4-5-15(22-2)19(23-3)13(12)9-14(21)17(11)18/h4-5,8,14H,6-7,9-10H2,1-3H3/t14-/m1/s1
InChi Key
UVDQDNQWGQFIAO-CQSZACIVSA-N
Origin
Plant/Stephania yunnanensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Crebanine is an aporphine alkaloid that has been found in Stephania venosa and has diverse biological activities.1,2,3,4,5 It is an antagonist of α7 nicotinic acetylcholine receptors (nAChRs; IC50 = 19.1 µM) and inhibits sodium currents (INa) in isolated guinea pig ventricular myocytes (IC50 = 283 µM).1,2 Crebanine is active against the Gram-positive bacteria M. lysodeikticus, B. cereus, B. megaterium, B. subtilis, and S. aureus (MICs = 0.312, 0.213, 0.312, 0.312, and 0.312 g/L, respectively). It inhibits the LPS-induced production of TNF-α, IL-6, nitric oxide (NO), and prostaglandin E2 (PGE2; Item No. 14010) in RAW 264.7 macrophages when used at a concentration of 29.5 µM.4 Crebanine inhibits the proliferation of A549 lung, MDA-MB-231 and MCF-7 breast, and SKOV3 and Caov-3 ovarian cells and reduces TNF-α induced invasion and migration of A549 cells in a concentration-dependent manner.5 It prevents scopolamine-induced memory deficits in the Morris water maze in mice when administered at a dose of 25 mg/kg.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rojsanga, P., Boonyarat, C., Utsintong, M., et alThe effect of crebanine on memory and cognition impairment via the alpha-7 nicotinic acetylcholine receptor. Life Sci. 91(3-4), 107-114 (2012).

    2. Xiao-Shan, H., Qing, L., Yun-Shu, M., et alCrebanine inhibits voltage-dependent Na+ current in guinea-pig ventricular myocytes. Chin. J. Nat. Med. 12(1), 20-23 (2014).

    3. Deng, Y., Yu, Y., Luo, H., et alAntimicrobial activity of extract and two alkaloids from traditional Chinese medicinal plant Stephania dielsiana. Food Chem. 124(4), 1556-1560 (2011).

    4. Intayoung, P., Limtrakul, P., and Yodkeeree, S. Antiinflammatory activities of crebanine by inhibition of NF-κB and AP-1 activation through suppressing MAPKs and Akt signaling in LPS-induced RAW264.7 macrophages. Biol. Pharm. Bull. 39(1), 54-61 (2016).

    5. Yodkeeree, S., Pompimon, W., and Limtrakul, P. Crebanine, an aporphine alkaloid, sensitizes TNF-α-induced apoptosis and suppressed invasion of human lung adenocarcinoma cells A549 by blocking NF-κB-regulated gene products. Tumour Biol. 35(9), 8615-8624 (2014).