Computer-Assisted Structure Elucidation of Black Chokeberry
(<i>Aronia melanocarpa</i>) Fruit Juice Isolates with a
New Fused Pentacyclic Flavonoid Skeleton
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Abstract
Melanodiol 4″-<i>O</i>-protocatechuate (<b>1</b>) and melanodiol (<b>2</b>)
represent novel flavonoid
derivatives isolated from a botanical dietary supplement ingredient,
dried black chokeberry (<i>Aronia melanocarpa</i>) fruit
juice. These noncrystalline compounds possess an unprecedented fused
pentacyclic core with two contiguous hemiketals. Due to having significant
hydrogen deficiency indices, their structures were determined using
computer-assisted structure elucidation software. The in vitro hydroxyl
radical-scavenging and quinone reductase-inducing activity of each
compound are reported, and a plausible biogenetic scheme is proposed