Rotenoids from Mirabilis multiflora

Rotenoids and Other Specialized Metabolites from the Roots of Mirabilis multiflora: Opioid and Cannabinoid Receptor Radioligand Binding Affinities

“…Primary screening of rotenoids from M. multiflora was conducted at a final concentration of 10 μM for competitive binding to the corresponding receptor using the reported methodology. − For the cannabinoid subtype receptor assays, rotenoids were added into a 96-well plate loaded with CHO-K1 cells, followed by 0.6 nM [ 3 H]-CP-55,940 and 10 μg of a cannabinoid membrane resuspended in 50 mM Tris (pH 7.4), 154 mM NaCl, and 20 mM Di-Na-EDTA supplemented with 0.02% BSA. Saturation experiments were performed to determine the optimal radioligand ([ 3 H]-enkephlin and [ 3 H]-DAMGO) and membrane concentrations for the opioid receptor subtype assays.…”

“…348 nm, reminiscent of a (6a S ,12a R ) absolute configuration. − Based on the above spectroscopic data, the structure of multiferone B ( 7 ) was assigned unequivocally as (6 R ,6a S ,12a R )-11,12a-dihydroxy-4,6,9-trimethoxy-10-methylrotenone (Figure ). This compound was described by us in 2013, but without defining its absolute configuration and reporting its physical data. These issues have been fully addressed herein.…”

“…The isolated rotenoids 2 – 7 were evaluated for in vitro binding assays using opioid receptor subtypes μ (MOR), κ (KOR), and δ (DOR) and cannabinoid receptors CB1 and CB2, employing methods described previously. − The results are shown in Tables and and indicated that the rotenoids showed moderate binding affinities especially toward the μ-MOR subtype, but no affinity toward the CB1 and CB2 receptor subtypes. Boeravinone A ( 4 ), isolated for the first time from M. multiflora , showed the highest binding affinity (64.5%) toward the μ-MOR subtype and selective inhibition of the specific binding of [ 3 H]-enkephalin to CHO-K1 membranes expressing the human μ-opioid receptor subtype at a concentration of 10 μM.…”