Depsides and other polar constituents from Origanum dictamnus L. and their in vitro antimicrobial activity in clinical strains.
Phytochemical investigation of the polar extracts of the aerial parts of Origanum dictamnus afforded 15 secondary metabolites. One new depside was isolated, to which the trivial name salvianolic acid P (1) was given, in addition to the known depsides rosmarinic acid (2) and rosmarinic acid methyl ester (3), as well as two monoterpenes, thymoquinone (4) and thymoquinol 2-O-beta-glucopyranoside (5); two simple phenolic acids, oresbiusin A (6) and E-caffeic acid (7); six flavonoids, namely, apigenin (8), kaempferol (9), quercetin (10), eriodictyol (11), taxifolin (12), naringenin (13); and two alicyclic derivatives, that is, 12-hydroxyjasmonic acid (14) and its 12-O-beta-d-glucoside (15). The structures of all isolated compounds were established by spectroscopic methods, mainly 1D and 2D NMR, as well as HPLC-DAD-MS and HR-MS spectrometric analyses. The absolute configuration of compound 1 was determined by CD measurements as 7'R, 7''S, 8''S. Compound 1 is interesting as it contains a benzodioxane ring, which is unusual in natural products. Moreover, it has been proved to be active against the Gram-negative clinical strains Acinetobacter hemolyticus , Empedobacter brevis , Pseudomonas aeruginosa , and Klebsiella pneumoniae .
Chatzopoulou
Aliki
A
Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, Panepistimiopolis, Zografou, 157 71 Athens, Greece.
Karioti
Anastasia
A
Gousiadou
Chrysoula
C
Lax Vivancos
Vanesa
V
Kyriazopoulos
Panagiotis
P
Golegou
Stamatina
S
Skaltsa
Helen
H
D000890:Anti-Infective Agents / Q000494:pharmacology*; D002934:Cinnamates / Q000494:pharmacology; D053630:Depsides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005419:Flavonoids / Q000494:pharmacology; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D062385:Hydroxybenzoates / Q000494:pharmacology; D039821:Monoterpenes / Q000494:pharmacology; D031341:Origanum / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry; D000097123:Rosmarinic Acid
D000890:Anti-Infective Agents; D002934:Cinnamates; D053630:Depsides; D005419:Flavonoids; D062385:Hydroxybenzoates; D039821:Monoterpenes; D010936:Plant Extracts; D000097123:Rosmarinic Acid