An alkaloid with diverse biological activities
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Isomer(s)
29243Fangchinoline
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Oxyacanthine (hydrochloride)

Item No. 44504

Product Insert (PDF)
Technical Information
Formal Name
3,4,4aR,5,16aS,17,18,19-octahydro-21,22,26-trimethoxy-4,17-dimethyl-2H-1,24:12,15-dietheno-6,10-metheno-16H-pyrido[2′,3′:17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinolin-9-ol, dihydrochloride
Molecular Formula
C37H40N2O6 • 2HCl
Formula Weight
646.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile:Water (1:1): Slightly soluble: 0.1-1 mg/ml
SMILES
COC1=C(OC(C=C2[C@@]3([H])CC4=CC=C5O)=C(C=C2CCN3C)OC)C([C@]6([H])CC7=CC=C(OC5=C4)C=C7)=C(CCN6C)C=C1OC.Cl.Cl
InChi Code
InChI=1S/C37H40N2O6.2ClH/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)17-23-8-11-30(40)31(18-23)44-26-9-6-22(7-10-26)16-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33;;/h6-11,18-21,28-29,40H,12-17H2,1-5H3;2*1H/t28-,29+;;/m1../s1
InChi Key
CJTFLIHOOZSHBJ-WIFSAEPPSA-N
Origin
Plant/Berberidis radix
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    Oxyacanthine is an alkaloid that has been found in B. crataegina and has diverse biological activities.1,2,3 It inhibits viral replication in Vero E6 cells infected with severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2; IC50 = 14.5 µM).1 Oxyacanthine induces relaxation of potassium-precontracted rat aortic rings (EC50 = 17.4 µM) and inhibits norepinephrine-, phenylephrine-, or serotonin-induced contractions in rat aortic rings in a concentration-dependent manner.2 In vivo, oxyacanthine (100 and 200 mg/kg) reduces acetic acid-induced vascular permeability but also induces gastric ulcers in mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lu, J., Cheng, Y., Zhang, Y., et al. Design, synthesis, and evaluation of novel oxyacanthine derivatives for anti-SARS-CoV-2 activity. Bioorg. Med. Chem. Lett. 113, 129951 (2024).

    2. Sotníková, R., Kost'álová, D., and Vaverková, S. Effect of bisbenzylisoquinoline alkaloids from Mahonia aquifolium on the isolated rat aorta. Gen. Pharmacol. 25(7), 1405-1410 (1994).

    3. Küpeli, E., Koşar, M., Yeşilada, E., et al. A comparative study on the anti-inflammatory, antinociceptive and antipyretic effects of isoquinoline alkaloids from the roots of Turkish Berberis species. Life Sci. 72(6), 645-657 (2002).