title: Raw coffee based dietary supplements contain carboxyatractyligenin derivatives inhibiting mitochondrial adenine-nucleotide-translocase.
abstract: Capsules, powders and tablets containing raw coffee extract are advertised to the consumer as antioxidant rich dietary supplements as part of a healthy diet. We isolated carboxyatractyligenin (4), 2-O-β-d-glucopyranosyl carboxyatractyligenin (6) and 3'-O-β-d-glucopyranosyl-2'-O-isovaleryl-2β-(2-desoxy-carboxyatractyligenin)-β-d-glucopyranoside (8) from green coffee and found strong inhibitory effects on phosphorylating respiration in isolated mitochondria similar to the effects of the known phytotoxin carboxyatractyloside. LC-MS/MS analysis of commercial green coffee based dietary supplements revealed the occurrence of carboxyatractyligenin, 3'-O-β-d-glucopyranosyl-2'-O-isovaleryl-2β-(2-desoxy-carboxyatractyligenin)-β-d-glucopyranoside, and 2-O-β-d-glucopyranosyl carboxyatractyligenin in concentrations up to 4.0, 5.7, and 41.6μmol/g, respectively. These data might help to gain first insight into potential physiological side-effects of green coffee containing dietary supplement.
authors.affiliation: Chair of Food Science and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, 85354 Freising, Germany. Electronic address: roman.lang@tum.de.
authors.forename: Roman
authors.initials: R
authors.lastname: Lang
authors.affiliation: ZIEL Unit Molecular Nutritional Medicine, Technische Universität München, Gregor-Mendel-Str 2, 85350 Freising, Germany.
authors.forename: Tobias
authors.initials: T
authors.lastname: Fromme
authors.affiliation: Chair of Food Science and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, 85354 Freising, Germany.
authors.forename: Anja
authors.initials: A
authors.lastname: Beusch
authors.affiliation: Chair of Food Science and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, 85354 Freising, Germany.
authors.forename: Tatjana
authors.initials: T
authors.lastname: Lang
authors.affiliation: ZIEL Unit Molecular Nutritional Medicine, Technische Universität München, Gregor-Mendel-Str 2, 85350 Freising, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Klingenspor
authors.affiliation: Chair of Food Science and Molecular Sensory Science, Technische Universität München, Lise-Meitner-Str. 34, 85354 Freising, Germany; ZIEL Bioanalytics Unit, Technische Universität München, Alte Akademie 10, 85354 Freising, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Hofmann
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000494:pharmacology; D001278:Atractyloside / Q000031:analogs & derivatives* / Q000494:pharmacology; D002853:Chromatography, Liquid; D003069:Coffee / Q000737:chemistry*; D019587:Dietary Supplements; D005511:Food Handling; D008297:Male; D051379:Mice; D008928:Mitochondria / Q000187:drug effects / Q000201:enzymology; D000226:Mitochondrial ADP, ATP Translocases / Q000037:antagonists & inhibitors / Q000378:metabolism*; D010766:Phosphorylation; D011208:Powders / Q000737:chemistry; D053719:Tandem Mass Spectrometry
chemical_list: D000975:Antioxidants; D003069:Coffee; D011208:Powders; C462123:atractyligenine; D001278:Atractyloside; D000226:Mitochondrial ADP, ATP Translocases
keywords: Carboxyatractyligenin; Dietary supplement; Green coffee; HPLC-MS/MS