Contribution à la phytochimie de genre Gentiana. XXIV.. Nouveaux C‐glycosides flavoniques dans les feuilles de Gentiana asclepiadeaL.

Abstract

p-Hydroxybenzoyl-2"-isoorientin-4'-O-~-~-glucoside(1) was isolated from the leaves of Gentiana asclepiadea L. by means of column chromatography. This is the first occurrence in nature of a p-hydroxybenzoate of isoorientin. p-Hydroxybenzoyl-2"-isoorientin (2) was also shown to be present in the same plant. asclepiadea L. (section Pneumonanthe). Cela pourrait avoir une signification particulitxe si l'on se rkf&re aux relations phylogknktiques prkconisees par Scharfetter [ 91. Les auteurs remercient vivement Monsieur le Prof. Cl. Favarger de son aide dans l'identification du materiel vkgktal, Monsieur le Prof. R. Tabacchi de l'interet qu'il a port6 A ce travail et Monsieur J.-L. Boss de son aide technique precieuse. 11s expriment leur gratitude A la maison Hofmann-La Roche et Co. A Bale (laboratoire du Prof. W. Boguth) pour le releve du spectre RMN. Partie exp6rimentaleGenPralitCs. Voir [ 11. 350 g de feuilles sechees de Gentiana asclepiadea L. ont fourni 15 mg de 1. -CCM.: systtme A= polyamide Macherey-Nagel DC,,, MeOH/H20 9: 1; systtme B= cellulose F50 Merck, AcOH 10%; systtme C= silicagel 60 F254 Merck, AcOEt/MeOH/H20 21:4:3.ComposP 1. F. 204-5", recristallis6 dans MeOH: Rf=0,68 (systtme A): Rf=0,70 (systtme B): Rf=0,38 (systtme C). Compose 2. Rf= 0,28 (systtme A): Rf= 0,63 (systtme B). Acides p-hydroxybenzo'ique et anisique. -CCM.: silicagel 60 F254, tolutne/pyridine 85: 15; cellulose F s~ Merck, AcOH 4% et tolutne/AcOH/H20 125:72: 3. Revelateur: Echtrotsalz B (Fluka) 0,2% H20.

Caucasian Gentiana Species: Untargeted LC-MS Metabolic Profiling, Antioxidant and Digestive Enzyme Inhibiting Activity of Six Plants

“…This was based on its deprotonated ion with m / z 729 and ions with m / z 609 and 447 that were caused by the loss of p -hydroxybenzoyl and hexosyl fragments, respectively. A flavone glycoside with a similar structure was isolated from G. asclepiadea and known as isoorientin-4′- O -(2″- O - p -hydroxybenzoyl)-glucoside [25].…”

“…Some chemical aspects of five species ( G. asclepiadea , G. cruciata , G. gelida , G. pneumonanthe , G. septemfida ) were shown previously, but G. paradoxa is still an unstudied species. The known data include information about flavonoids (flavones only) in four species [11,12,13,14,15,16,17,18,19,20,21,22,23,24,25], xanthones (mangiferin, gentisin and its glycosides) in three species [15,16,17,18,20,26,27], iridoid glycosides in five species [18,19,22,27,28,29,30,31,32], monoterpenes in G. pneumonanthe [32], and triterpenes and naphthodipyranodione in G. asclepiadea [32,33]. In total, thirty-nine compounds were found in five gentians with most diverse classes of flavonoids and iridoid glycosides (Table S2).…”

Iridoids and flavonoids from the aerial parts of Gentiana asclepiadea L. with anti-inflammatory and analgesic activities

“…Recent pharmacological studies on G. asclepiadea extracts demonstrated a wide range of bioactivities including antioxidant, antimicrobial, antigenotoxic, and hepatoprotective effects [12][13][14][15]. Few previous phytochemical investigations on this species indicated the presence of secoiridoids, flavonoids, and xanthone derivatives, [16][17][18][19]. However, no detailed study has been conducted on the isolation of its secondary metabolites and their in vitro anti-inflammatory and analgesic activities.…”