title: 2-O-β-D-Glucopyranosyl-carboxyatractyligenin from Coffea L. inhibits adenine nucleotide translocase in isolated mitochondria but is quantitatively degraded during coffee roasting.
abstract: Atractyloside (1) and carboxyatractyloside (2) are well-known inhibitors of the adenine nucleotide translocase (ANT) in mitochondria, thus effectively blocking oxidative phosphorylation. Structurally related derivatives atractyligenin (3), 2-O-β-D-glucopyranosyl-atractyligenin (4), 3'-O-β-D-glucopyranosyl-2'-O-isovaleryl-2β-(2-desoxy-atractyligenin)-β-D-glucopyranoside (5), and 2-O-β-D-glucopyranosyl-carboxyatractyligenin (6) were isolated from raw beans of Coffea L. and the impact of 1-6 on ANT activity was evaluated in isolated mitochondria. Among the coffee components, 6 significantly inhibited ANT activity leading to reduced respiration. Quantitative analysis in commercial coffees, experimental roastings of coffee, and model experiments using purified compound 6 consistently revealed a complete degradation during thermal treatment. In comparison, raw coffee extracts were found to contain high levels of 6, which are therefore expected to be present in food products enriched with raw coffee extracts. This implies the necessity of analytically controlling the levels of 6 in raw coffee extracts when used as additives for food products.
authors: Chair of Food Science and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, 85354 Freising, Germany.
authors: Roman
authors: R
authors: Lang
authors: Tobias
authors: T
authors: Fromme
authors: Anja
authors: A
authors: Beusch
authors: Anika
authors: A
authors: Wahl
authors: Martin
authors: M
authors: Klingenspor
authors: Thomas
authors: T
authors: Hofmann
mesh_terms: D000818:Animals; D001278:Atractyloside / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D040503:Coffea / Q000737:chemistry*; D003296:Cooking; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D008930:Mitochondria, Liver / Q000187:drug effects / Q000201:enzymology* / Q000378:metabolism; D000226:Mitochondrial ADP, ATP Translocases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D013997:Time Factors
chemical_list: C586988:2-O-beta-D-glucopyranosyl-carboxyatractyligenin; D004791:Enzyme Inhibitors; D001278:Atractyloside; D000226:Mitochondrial ADP, ATP Translocases
keywords: 2-O-β-d-Glucopyranosyl-carboxyatractyligenin; Adenine nucleotide translocator; Coffea L.; Coffee; Rubiaceae; UPLC-Time-of-Flight-MS quantification