Antimicrobial Benzyltetrahydroisoquinoline-Derived Alkaloids from the Leaves of Doryphora aromatica
journal contributionposted on 05.03.2021, 20:04 by Miaomiao Liu, Jianying Han, Yunjiang Feng, Gordon Guymer, Paul I. Forster, Ronald J. Quinn
Four new alkaloids, (R)-nomimantharine trifluoroacetate (2), 12-demethylphaeantharine trifluoroacetate (3), nominanthranal trifluoroacetate (4), and the enolic form of 1-hydroxy-6,7-dimethoxy-2-methylisoquinoline trifluoroacetate (5), together with the known dimeric alkaloid phaeantharine trifluoroacetate (1), have been isolated from the extract of the leaves of the rainforest tree Doryphora aromatica (Monimiaceae). The structures of these compounds were elucidated by HRMS and 1D and 2D NMR data. (R)-Nomimantharine trifluoroacetate (2) contains an ether linkage connecting a benzylisoquinoline unit with a tetrahydroisoquinoline, a novel class of dimeric alkaloid. The absolute configuration of (R)-nomimantharine trifluoroacetate (2) was established via electronic circular dichroism data. The compounds isolated were subjected to in vitro antimicrobial assays against a panel of pathogenic microorganisms, including Mycobacterium smegmatis, M. tuberculosis, Escherichia coli, Staphylococcus aureus (SA), and five clinical isolates of oxacillin/methicillin-resistant S. aureus (MRSA). Phaeantharine trifluoroacetate (1) and (R)-nomimantharine trifluoroacetate (2) showed moderate inhibitory activities against Mycobacteria and MRSA strains.
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benzylisoquinoline unit2 D NMR dataAntimicrobial Benzyltetrahydroisoqu...dimeric alkaloidrainforest tree Doryphora aromaticaPhaeantharine trifluoroacetatedimeric alkaloid phaeantharine trif...enolic formMRSA strainsDoryphora aromaticaEscherichia coliantimicrobial assays1 DMycobacterium smegmatisether linkageStaphylococcus aureusdichroism datanovel classHRMS