title: Antioxidant glucosylated caffeoylquinic acid derivatives in the invasive tropical soda apple, Solanum viarum.
abstract: Eggplant and related Solanum species contain abundant caffeoylquinic acid (CQA) derivatives. Fruit of the invasive species Solanum viarum Dunal contain numerous complex CQA derivatives, but only a few have been identified. The structures of two new compounds isolated from methanolic extracts of S. viarum fruit by C(18)-HPLC-DAD were determined using 2D NMR and MS data. Both include two 5-CQA molecules joined by glucose via ester and glycosidic linkages. The structures of compounds 1 and 2 (viarumacids A and B) are, respectively, 5-caffeoyl- and 3-malonyl-5-caffeoyl-[4-(1β-[6-(5-caffeoyl)quinate]glucopyranosyl)]quinic acid. The antioxidant activities determined by ABTS(•+) and DPPH(•) assays were in the order 1 > 2 > 5-CQA.
authors.affiliation: Department of Biological Sciences, Lehman College, 250 Bedford Park Boulevard West, Bronx, New York 10468, USA.
authors.forename: Shi-Biao
authors.initials: SB
authors.lastname: Wu
authors.forename: Rachel S
authors.initials: RS
authors.lastname: Meyer
authors.forename: Bruce D
authors.initials: BD
authors.lastname: Whitaker
authors.forename: Amy
authors.initials: A
authors.lastname: Litt
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Kennelly
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D052160:Benzothiazoles; D002851:Chromatography, High Pressure Liquid; D005638:Fruit / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D058865:Introduced Species; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D032322:Solanum / Q000737:chemistry*; D032323:Solanum melongena / Q000737:chemistry; D013451:Sulfonic Acids
chemical_list: D000975:Antioxidants; D052160:Benzothiazoles; D005960:Glucosides; D013451:Sulfonic Acids; C472707:caffeoylquinic acid; C578549:viarumacid A; C578550:viarumacid B; D011801:Quinic Acid; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid