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Berberrubine chloride

$97

  • Brand : BIOFRON

  • Catalogue Number : AV-H24061

  • Specification : 98%

  • CAS number : 15401-69-1

  • Formula : C19H16NO4.Cl

  • Molecular Weight : 321.33

  • PUBCHEM ID : 72703

  • Volume : 20mg

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Catalogue Number

AV-H24061

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

321.33

Appearance

Red needle crystal

Botanical Source

Thalictrum aquilegifolium Linn. var. sibiricum Regel et Tiling; Berberis heteropoda Schtenk /Alkaloid from the twigs of Berberis actinacantha and from the stems of Berberis darwinii and Berberis valdiviana. Also from Berberis vulgaris, Thalictrum polygamum and Fibraurea chloroleuca (Berberidaceae, Ranunculaceae, Menispermaceae)

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)O.[Cl-]

Synonyms

berberoline chloride/berberrubine/2,3-methylenedioxy-9-hydroxy-10-methoxyprotoberberine chloride/Berberrubine chloride/5,6-Dihydro-9-hydroxy-10-methoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium chloride/9-Hydroxy-10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride/Beroline chloride/berberrubine hydrochloride/beberrubine chloride/9-Demethoxy-9-hydroxyberberinium chloride/Chileninone/hydrochloride berberrubine/Berberubine hydrochloride/1,3-Benzodioxolo[5,6-a]benzo[g]quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-, chloride (1:1)/9-Berberoline chloride

IUPAC Name

17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol;chloride

Applications

Berberrubine chloride is an active metabolite of berberine, attenuates ulcerative colitis in mice model[1].

Density

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

Boiling Point

Melting Point

245℃ (DEC.)

InChl

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

InChl Key

GYFSYEVKFOOLFZ-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:15401-69-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29538417

Abstract

Ulcerative colitis (UC) is a chronic relapsing disease without satisfactory treatments, in which intestinal inflammation and disrupted intestinal epithelial barrier are two main pathogeneses triggering UC. Berberrubine (BB) is deemed as one of the major active metabolite of berberine (BBR), a naturally-occurring isoquinoline alkaloid with appreciable anti-UC effect. This study aimed to comparatively investigate the therapeutic effects of BB and BBR on dextran sodium sulfate (DSS)-induced mouse colitis model, and explore the potential underlying mechanism. Results revealed that BB (20 mg/kg) produced a comparable therapeutic effect as BBR (50 mg/kg) and positive control sulfasalazine (200 mg/kg) by significantly reducing the disease activity index (DAI) with prolonged colon length and increased bodyweight as compared with the DSS group. BB treatment was shown to significantly ameliorate the DSS-induced colonic pathological alternations and decreased histological scores. In addition, BB markedly attenuated colonic inflammation by alleviating inflammatory cell infiltration and inhibiting myeloperoxidase (MPO) and cytokines (TNF-α, IFN-γ, IL-1β, IL-6, IL-4 and IL-10) productions in DSS mice. Furthermore, BB treatment substantially upregulated the expression of tight junction (TJ) proteins (zonula occludens-1, zonula occludens-2, claudin-1, occludin) and mRNA expression of mucins (mucin-1 and mucin-2), and decreased the Bax/Bcl-2 ratio. In summary, BB exerted similar effect to its analogue BBR and positive control in attenuating DSS-induced UC with much lower dosage and similar mechanism. The protective effect observed may be intimately associated with maintaining the integrity of the intestinal mucosal barrier and mitigating intestinal inflammation, which were mediated at least partially, via favorable modulation of TJ proteins and mucins and inhibition of inflammatory mediators productions in the colonic tissue. This is the first report to demonstrate that BB possesses pronounced anti-UC effect similar to BBR and sulfasalazine with much smaller dosage. BB might have the potential to be further developed into a promising therapeutic option in the treatment of UC.

Title

Berberrubine attenuates mucosal lesions and inflammation in dextran sodium sulfate-induced colitis in mice.

Author

Yu XT1, Xu YF2, Huang YF3, Qu C3, Xu LQ3, Su ZR3,4, Zeng HF1, Zheng L5, Yi TG5, Li HL5, Chen JP5, Zhang XJ2.

Publish date

2018 Mar 14

PMID

29411090

Abstract

Berberine (BBR) is a natural alkaloid obtained from Berberis species plants, known for its protective effects against several diseases. Among the primary BBR metabolites, berberrubine (M1) showed the highest plasma concentration but few and conflicting data are available regarding its concentration in biological fluids related to its new potential activity on vascular cells. A combined analytical approach was applied to study biodistribution of M1 in comparison with BBR. The optimization of sample clean-up combined with a fully validated HPLC-ESI-MS/MS tailored for M1 allows sufficient detectability and accuracy to be reached in the different studied organs even when administered at low dose, comparable to that assumed by human. A predictive human vascular endothelial cell-based assay to measure intracellular xanthine oxidase has been developed and applied to study unexplored activities of M1 alongside other common activities. Results showed that oral M1 treatment exhibits higher plasma levels than BBR, reaching maximum concentration 400-fold higher than BBR (204 vs 0.5 ng/mL); moreover, M1 exhibits higher concentrations than BBR also in all the biological compartments analyzed. Noteworthy, the two compounds follow two different excretion routes: M1 through urine, while BBR through feces. In vitro studies demonstrated that M1 inhibited intracellular xanthine oxidase activity, one of the major sources of reactive oxygen species in vasculature, with an IC50 = 9.90 ± 0.01 μg/mL and reduced the expression of the inflammatory marker ICAM-1. These peculiar characteristics allow new perspectives to be opened up for the direct use of M1 instead of BBR in endothelial dysfunction treatment.

KEYWORDS

Berberrubine; Biodistribution; Chemiluminescent cell-based assay; Endothelial dysfunction; Mass spectrometry; Xanthine oxidase

Title

Combined analytical approaches to define biodistribution and biological activity of semi-synthetic berberrubine, the active metabolite of natural berberine.

Author

Porru E1, Franco P1, Calabria D2, Spinozzi S1, Roberti M3, Caliceti C4,5,6, Roda A1,2,7.

Publish date

2018 Jun;

PMID

29351921

Abstract

Berberrubine (BRB) has a strong lipid-lowering effect and can be extensively metabolized into berberrubine-9-O-β-d-glucuronide (BRBG) in vivo. Recently, pharmacokinetics studies showed that the production of BRBG was significantly decreased in the urine of mice fed with a high-fat diet (HFD), indicating a decreased glucuronidation capacity. Based on the UDP-glucuronosyltransferase (UGT) isoform identification, hepatic and renal microsomal incubation, glucuronidation was examined to suggest the metabolism of BRB in liver and kidneys. The results showed that the renal UGT activity for metabolizing BRB markedly decreased, which may be highly related to the decreased expression and activity of renal Ugt1a7c. Surprisingly, in vitro studies revealed neither BRB nor BRBG inhibited the renal UGT activity. By employing an integrated strategy of metabolomics and pharmacokinetics, we identified and confirmed for the first time the inhibitory effect of some potential endogenous molecules on the renal glucuronidation of C57BL/6J mice, such as glutaric acid (GA) and linoleic acid (LA). By employing recombinant human UGTs, we found that GA and LA efficiently affect the activity of recombinant human UGT1A7, 1A9, and 1A8 at their normal or abnormal physiologic levels in vivo. GA (2 mM) markedly inhibited the activity of UGT1A7 by 89.4% and UGT1A9 by 32.8%. The inhibition rates reached 99.3% for UGT1A9, 48.3% for UGT1A7, and 46.8% for UGT1A8 with LA at 200 μM. It has been suggested that the endogenous molecules have the potential to affect the efficiency of glucuronidation, which might be a key factor contributing to individual differences in drug metabolism.

Copyright ? 2018 by The American Society for Pharmacology and Experimental Therapeutics.

Title

Inhibitory Effects of Endogenous Linoleic Acid and Glutaric Acid on the Renal Glucuronidation of Berberrubine in Mice and on Recombinant Human UGT1A7, 1A8, and 1A9.

Author

Yang N1, Li S1, Yan C1, Sun R1, He J1, Xie Y1, Peng Y1, Wang G2, Aa J2.

Publish date

2018 Mar