An isoquinoline alkaloid with diverse biological activities
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Parent Compound(s)
10006427Berberine (chloride)
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Berberrubine (chloride)

Item No. 42515

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,6-dihydro-9-hydroxy-10-methoxy-bnzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, monochloride
CAS Number
15401-69-1
Molecular Formula
C19H16NO4 • Cl
Formula Weight
357.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlEthanol: Slightly soluble: 0.1-1 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
OC1=C(C=CC2=CC3=[N+](C=C12)CCC4=CC5=C(OCO5)C=C34)OC.[Cl-]
InChi Code
InChI=1S/C19H15NO4.ClH/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21;/h2-3,6-9H,4-5,10H2,1H3;1H
InChi Key
GYFSYEVKFOOLFZ-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $52

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    10 mg

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    25 mg

    $207

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    50 mg

    $311

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    Cayman Chemical
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    Product Description

    Berberrubine is an isoquinoline alkaloid that has been found in C. chinensis and has diverse biological activities.1,2,3,4,5,6,7 It is also an active metabolite of berberine (Item No. 10006427).1,2 Berberrubine (600 µM) scavenges hydroxyl radicals and chelates ferrous iron in cell-free assays.3 It potentiates topoisomerase II-induced cleavage of isolated E. coli DNA when used at a concentration of 10 µM.4 Berberrubine inhibits N-methyl-4-phenylpyridinium (MPP+) uptake in MDCK cells expressing human organic cation transporter 1 (OCT1), OCT2, or OCT3 (IC50s = 1.26, 8.3, and 4.88 µM, respectively).5 It decreases triglyceride levels without inducing cytotoxicity in HepG2 liver cells when used at a concentration of 15 µM.6 In vivo, berberrubine (20 mg/kg per day) increases intestinal length, decreases disease severity and colonic epithelial deterioration, reduces colonic TNF-α, IFN-γ, IL-6, IL-1β, IL-4, and IL-10 levels, and decreases colonic myeloperoxidase (MPO) activity in a mouse model of ulcerative colitis induced by dextran sodium sulfate (DSS).7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, Y., Ren, G., Wang, Y.X., et al. Bioactivities of berberine metabolites after transformation through CYP450 isoenzymes. J. Transl. Med. 9, 62 (2011).

    2. Zuo, F., Nakamura, N., Akao, T., et al. Pharmacokinetics of berberine and its main metabolites in conventional and pseudo germ-free rats determined by liquid chromatography/ion trap mass spectrometry. Drug Metab. Dispos. 34(12), 2064-2072 (2006).

    3. Jang, M.H., Kim, H.Y., Kang, K.S., et al. Hydroxyl radical scavenging activities of isoquinoline alkaloids isolated from Coptis chinensis. Arch. Pharm. Res. 32(3), 341-345 (2009).

    4. Kobayashi, Y., Yamashita, Y., Fujii, N., et al. Inhibitors of DNA topoisomerase I and II isolated from the Coptis rhizomes. Planta Med. 61(5), 414-418 (1995).

    5. Li, L., Sun, S., Weng, Y., et al. Interaction of six protoberberine alkaloids with human organic cation transporters 1, 2 and 3. Xenobiotica 46(2), 175-183 (2016).

    6. Cao, S., Zhou, Y., Xu, P., et al. Berberine metabolites exhibit triglyceride-lowering effects via activation of AMP-activated protein kinase in Hep G2 cells. J. Ethnopharmacol. 149(2), 576-582 (2013).

    7. Yu, X.T., Xu, Y.F., Huang, Y.F., et al. Berberrubine attenuates mucosal lesions and inflammation in dextran sodium sulfate-induced colitis in mice. PLoS One 13(3), e0194069 (2018).