title: (1S,3R,4S,5R)5-O-Caffeoylquinic acid: isolation, stereo-structure characterization and biological activity.
abstract: Sorbus domestica fruits (sorbs) are commonly harvested and consumed for their nutritious qualities and have long been used as natural remedy against diabetes in the popular medicine. Recently, sorbs have been described as sources of antioxidant compounds including polyphenols. Chemical analyses carried out on sorbs collected in Southern Italy have led to the isolation of a chlorogenic acid isomer as the main antioxidant compound contained in the fruit butanol extract. NMR studies have identified the isolated compound as (1S,3R,4S,5R)5-O-Caffeoylquinic acid. In comparison to chlorogenic acid, the isolated isomer features an inverted configuration at C4. Such configurational inversion causes the chlorogenic acid stereoisomer acid to assume a preferential conformation remarkably different from that of chlorogenic acid. This seems to account for the enhanced potency of (1S,3R,4S,5R)5-O-Caffeoylquinic acid to reduce both the glucose and cholesterol uptakes by the cell line HepG2 when compared to chlorogenic acid.
authors.affiliation: Department of Pharmacy, University of Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy. Electronic address: forino@unina.it.
authors.forename: Martino
authors.initials: M
authors.lastname: Forino
authors.affiliation: Department of Pharmacy, University of Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Gian Carlo
authors.initials: GC
authors.lastname: Tenore
authors.affiliation: Department of Pharmacy, University of Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Luciana
authors.initials: L
authors.lastname: Tartaglione
authors.affiliation: Department of Pharmacy, University of Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Dell'Aversano
authors.initials: D
authors.lastname: Carmela
authors.affiliation: Department of Pharmacy, University of Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Ettore
authors.initials: E
authors.lastname: Novellino
authors.affiliation: Department of Pharmacy, University of Napoli "Federico II", via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Patrizia
authors.initials: P
authors.lastname: Ciminiello
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001692:Biological Transport / Q000187:drug effects; D002726:Chlorogenic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry; D005947:Glucose / Q000378:metabolism; D056945:Hep G2 Cells; D006801:Humans; D007558:Italy; D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D031994:Sorbus / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000975:Antioxidants; D002726:Chlorogenic Acid; D005947:Glucose; D010936:Plant Extracts; D011801:Quinic Acid; C473200:5-caffeoylquinic acid
keywords: (1S,3R,4S,5R)5-O-Caffeoylquinic acid; Antioxidant activity; Chlorogenic acid; NMR; Sorbus domestica