Oxyberberrubine

Oxyberberrubine, a novel liver microsomes-mediated secondary metabolite of berberine, alleviates hyperuricemic nephropathy in mice.[Pubmed:36334387]

Phytomedicine. 2023 Jan;108:154521.

BACKGROUND: Berberrubine (BRB), one of the major metabolites of berberine (BBR), exerts an anti-hyperuricemic effect even superior to BBR. Liver is an important location for drug transformation. Nevertheless, there are few studies on the bioactivities and metabolites of BRB. PURPOSE: We investigated whether Oxyberberrubine (OBR), a liver metabolite of BRB, exerted urate-lowering and reno-protective effects in hyperuricemic mice. METHODS: Liver microsomes were used to incubate BRB for studying its biotransformation. We isolated and identified its new metabolite OBR, and investigated its anti-hyperuricemic and reno-protective effects. In this work, the hyperuricemic mice model was established by receiving potassium oxonate (PO) and hypoxanthine (HX) for 7 consecutive days. 1 h after modeling, different dosages of OBR (5, 10 and 20 mg/kg), BRB (20 mg/kg) or febuxostat (Fex, 5 mg/kg) were given mice by gavage. RESULTS: Results showed that OBR possessed potent anti-hyperuricemic and reno-protective effects in hyperuricemic mice. Serum uric acid (UA) level was lowered, and the activities of xanthine oxidase (XOD) as well as adenosine deaminase (ADA) in the liver were suppressed after treatment with OBR. Hepatic expressions of XOD were remarkably decreased at mRNA and protein levels by OBR treatment. In addition, OBR prominently alleviated renal injury, embodied in markedly reduced serum creatinine and blood urea nitrogen (BUN) levels, decreased inflammatory mediators (TNF-alpha, IL-1beta, IL-6 and IL-18) levels, mRNA expression of CYP27B1 and repairment of renal tissues damage. Besides, OBR down-regulated renal expression of urate transporter 1 (URAT1), glucose transporter 9 (GLUT9), NOD-like receptor 3 (NLRP3), apoptosis-associated speck-like protein containing CARD (ASC), and caspase-1 at mRNA and protein levels. CONCLUSIONS: In short, our study indicated that OBR possessed superior anti-hyperuricemic and reno-protective effects, at least in part, through the inhibition of XOD, URAT1, GLUT9 and NLRP3 inflammasome signaling pathway in the kidney.

Total syntheses of (+/-)-gusanlung a, (+/-)-gusanlung D and 8-oxyberberrubine and the uncertainty concerning the structures of (-)-gusanlung A, (-)-gusanlung D and 8-oxyberberrubine.[Pubmed:19214157]

Molecules. 2009 Feb 12;14(2):726-37.

(+/-)-Gusanlung A, 8-Oxyberberrubine and (+/-)-gusanlung D have been synthesized by radical cyclisation of the corresponding 2-aroyl-1-methylenetetra- hydroisoquinolines. The (1)H and (13)C spectra of (-)-gusanlung D were found to be different from those of synthetic (+/-)-gusanlung D. Careful analyses of the (13)C spectra of (-)-gusanlung A and natural 8-Oxyberberrubine also cast doubt on the correctness of the structures previously assigned to these two compounds. (+/-)-Gusanlung A and (+/-)-gusanlung D were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028.

Oxyberberrubine (CAS 29580-82-3) is a natural product offered by BioCrick for research applications. Customers can buy or order Oxyberberrubine from BioCrick, a supplier and manufacturer of research chemicals, with product specifications, purity, packaging, and pricing information available upon request.