title: Computer-Assisted Structure Elucidation of Black Chokeberry (Aronia melanocarpa) Fruit Juice Isolates with a New Fused Pentacyclic Flavonoid Skeleton.
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.
authors.affiliation: †Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, Ohio 43210, United States.
authors.forename: C Benjamin
authors.initials: CB
authors.lastname: Naman
authors.affiliation: †Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, Ohio 43210, United States.
authors.forename: Jie
authors.initials: J
authors.lastname: Li
authors.affiliation: ‡Advanced Chemistry Development, Inc., Toronto Department, 8 King Street East, Suite 107, Toronto, ON M5C1B5, Canada.
authors.forename: Arvin
authors.initials: A
authors.lastname: Moser
authors.affiliation: ‡Advanced Chemistry Development, Inc., Toronto Department, 8 King Street East, Suite 107, Toronto, ON M5C1B5, Canada.
authors.forename: Jeffery M
authors.initials: JM
authors.lastname: Hendrycks
authors.affiliation: †Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, Ohio 43210, United States.
authors.forename: P Annécie
authors.initials: PA
authors.lastname: Benatrehina
authors.affiliation: †Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, Ohio 43210, United States.
authors.forename: Heebyung
authors.initials: H
authors.lastname: Chai
authors.affiliation: §Nuclear Magnetic Resonance Facility, Campus Chemical Instrument Center, The Ohio State University, Columbus, Ohio 43210, United States.
authors.forename: Chunhua
authors.initials: C
authors.lastname: Yuan
authors.affiliation: ∥Nature's Sunshine Products, Inc., 1655 North Main Street, Spanish Fork, Utah 84660, United States.
authors.forename: William J
authors.initials: WJ
authors.lastname: Keller
authors.affiliation: †Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, Ohio 43210, United States.
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000975:Antioxidants / Q000737:chemistry* / Q000302:isolation & purification*; D003198:Computer Simulation; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification*; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification*; D005638:Fruit / Q000737:chemistry*; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000737:chemistry*; D010084:Oxidation-Reduction; D046936:Photinia / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification*; D011083:Polycyclic Compounds / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D005419:Flavonoids; D016166:Free Radical Scavengers; D010936:Plant Extracts; D011083:Polycyclic Compounds; C000602700:melanodiol; C000602699:melanodiol 4'-O-protocatechuate; D016660:NAD(P)H Dehydrogenase (Quinone)