An isoquinoline alkaloid with anticancer and gastroprotective activities
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Parent Compound(s)
28424Coptisine (chloride)
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8-Oxycoptisine

Item No. 34472

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6,7-dihydro-4H-bis[1,3]benzodioxolo[5,6-a:4′,5′-g]quinolizin-4-one
CAS Number
19716-61-1
Synonyms
  • 8-Oxocoptisine
Molecular Formula
C19H13NO5
Formula Weight
335.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: soluble
λmax
224, 348 nm
SMILES
O=C1C2=C(C=C3C4=CC5=C(C=C4CCN13)OCO5)C=CC6=C2OCO6
InChi Code
InChI=1S/C19H13NO5/c21-19-17-11(1-2-14-18(17)25-9-22-14)5-13-12-7-16-15(23-8-24-16)6-10(12)3-4-20(13)19/h1-2,5-7H,3-4,8-9H2
InChi Key
UCAFJBSQKXVPDX-UHFFFAOYSA-N
Origin
Plant/Thalictrum glandulosissimum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $103

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    5 mg

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    10 mg

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    Product Description

    8-Oxycoptisine is an isoquinoline alkaloid that has been found in Coptis chinensis and has anticancer and gastroprotective activities.1,2,3 It is an active metabolite of coptisine (Item No. 28424) formed by gut microbiota.1 8-Oxycoptisine is cytotoxic against NCI-N87 gastric, but not Caco-2 colon, cancer cells (IC50s = 20.31 and >100 µM, respectively).2 It reverses resistance to paclitaxel (Item No. 10461) in non-multidrug-resistant SKOV3 cells, as well as in HCT-15 cells, which endogenously express high levels of P-glycoprotein (P-gp), with EC50 values of 0.3 and 0.5 ng/ml, respectively.3 It reduces colonic shortening and inflammatory cell infiltration in a mouse model of ulcerative colitis induced by dextran sulfate (DSS; Item No. 23250) when administered at doses of 50 or 100 mg/kg.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ai, G., Huang, Z., Cheng, J., et al. Gut microbiota-mediated transformation of coptisine Into a novel metabolite 8-oxocoptisine: Insight into its superior anti-colitis effect. Front. Pharmacol. 12, 12:639020 (2021).

    2. Qian, P., and Yang, X.-W. Five new alkaloids from Coptidis Rhizoma-Euodiae Fructus couple and their cytotoxic activities against gastrointestinal cancer cells. Fitoterapia 93, 74-80 (2014).

    3. Min, Y.D., Yang, M.C.M., Lee, K.H., et al. Protoberberine alkaloids and their reversal activity of P-gp expressed multidrug resistance (MDR) from the rhizome of Coptis japonica Makino. Arch. Pharm. Res. 29(9), 757-761 (2006).