Abstract
Melanodiol 4″-O-protocatechuate (1) and melanodiol (2) represent novel flavonoid derivatives isolated from a botanical dietary supplement ingredient, dried black chokeberry (Aronia melanocarpa) 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.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Antioxidants / chemistry*
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Antioxidants / isolation & purification*
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Computer Simulation
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Flavonoids / chemistry*
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Flavonoids / isolation & purification*
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Free Radical Scavengers / chemistry*
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Free Radical Scavengers / isolation & purification*
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Fruit / chemistry*
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Molecular Structure
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NAD(P)H Dehydrogenase (Quinone) / chemistry*
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Oxidation-Reduction
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Photinia / chemistry*
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Plant Extracts / chemistry*
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Plant Extracts / isolation & purification*
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Polycyclic Compounds / chemistry*
Substances
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Antioxidants
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Flavonoids
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Free Radical Scavengers
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Plant Extracts
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Polycyclic Compounds
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melanodiol
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melanodiol 4'-O-protocatechuate
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NAD(P)H Dehydrogenase (Quinone)