Isolation and pharmacological activity of phenylpropanoid esters from Marrubium vulgare.
The isolation and identification of major phenylpropanoid esters from Marrubium vulgare: (+) (E)-caffeoyl-L-malic acid 1, acteoside 2, forsythoside B 3, arenarioside 4, ballotetroside 5, as well as their anti-inflammatory activity are reported for the first time. We evaluated the inhibitory effects of these five compounds on cyclooxygenase (Cox) catalysed prostaglandin biosynthesis activity. Only the glycosidic phenylpropanoid esters showed an inhibitory activity towards the Cox-2 enzyme and three of them: acteoside 2, forsythoside B 3, arenarioside 4, exhibited higher inhibitory potencies on Cox-2 than on Cox-1. These results are of interest, as Cox-2 is mainly associated with inflammation and the Cox-1 inhibition with adverse side effects often observed with non-steroidal anti-inflammatory drugs. The occurrence of these phenylpropanoid esters could also explain some other pharmacological properties of M. vulgare.
Sahpaz
Sevser
S
Laboratoire de Pharmacognosie, Faculté des Sciences Pharmaceutiques et Biologiques, B.P. 83, F-59006, Lille, Cedex, France.
Garbacki
Nancy
N
Tits
Monique
M
Bailleul
Francois
F
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000494:pharmacology; D002109:Caffeic Acids / Q000737:chemistry / Q000494:pharmacology; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004952:Esters; D006027:Glycosides / Q000737:chemistry / Q000494:pharmacology; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D008293:Malates / Q000737:chemistry / Q000494:pharmacology; D027522:Marrubium / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018514:Plant Structures / Q000737:chemistry; D020005:Propanols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D011451:Prostaglandin-Endoperoxide Synthases / Q000378:metabolism
D000894:Anti-Inflammatory Agents, Non-Steroidal; D002109:Caffeic Acids; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D004952:Esters; D006027:Glycosides; D007527:Isoenzymes; D008293:Malates; D010936:Plant Extracts; D020005:Propanols; C099798:caffeoylmalic acid; C439395:1-phenylpropanol; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases; C058049:forsythiaside