Journal
JOURNAL OF NATURAL PRODUCTS
Volume 63, Issue 8, Pages 1140-1145Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np000166d
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Flavonolignans represent natural compounds whose biosynthesis presumes a radical coupling of a ring B catecholic flavonoid with a molecule of coniferyl alcohol or an analogue. Many natural flavonolignans can exist as regioisomers, depending on how the coupled coniferyl alcohol moiety orients to the flavonoid. These regioisomers are often difficult to separate and have virtually identical NMR spectra. Structural assignments for some have changed with time or have been given without proof. We here report syntheses of both regioisomers of the flavonolignan hydnocarpin and one isomer of a plant isolate previously known as 5'-methoxyhydnocarpin. This isomer, here renamed 5'-methoxyhydnocarpin-D, was recently shown to be a potent inhibitor of a Staphylococcus aureus multidrug resistant efflux pump.
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