Ent-kaurane glycosides and sesquiterpene lactones of the hirsutinolide type from Vernonia triflosculosa.
Investigation of the aerial parts of Vernonia triflosculosa afforded three hirsutinolides of which 8alpha-(4alpha-hydroxymethacryloyloxy)-10alpha-hydroxy-1,13-dimethoxy-hirsutinolide is new, three ent-kaurane diterpenes, among which the 19-[alpha-L-arabinopyranosyl-(1-->2)-beta-D-glucopyranosyl] esters of 16beta-hydroxy-ent-kauran-19-oic acid and of 16beta,17-hydroxy-ent-kauran-19-oic acid are also new. Diterpenes are reported here for the first time in the large genus Vernonia. Their structures were elucidated using 1D and 2D NMR measurement as well as ESI, CIMS, and HRMS analysis. Two hirsutinolides were studied for their NF-kappaB DNA binding activity in HaCaT cells (a human cell line similar to keratinocytes) and for their inhibition on IL-8 production in HeLa cells.
Kos
Olha
O
Institute of Pharmaceutical Sciences, Department of Pharmaceutical Biology and Biotechnology, Albert-Ludwigs-University of Freiburg, Stefan-Meier-Street 19, 79104 Freiburg, Germany.
Castro
Víctor
V
Murillo
Renato
R
Poveda
Luis
L
Merfort
Irmgard
I
D002478:Cells, Cultured; D018360:Crystallography, X-Ray; D004247:DNA / Q000187:drug effects / Q000378:metabolism; D004187:Disaccharides / Q000737:chemistry* / Q000302:isolation & purification; D045786:Diterpenes, Kaurane / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D016209:Interleukin-8 / Q000037:antagonists & inhibitors; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D008968:Molecular Conformation; D016328:NF-kappa B / Q000037:antagonists & inhibitors / Q000378:metabolism; D012015:Reference Standards; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013045:Species Specificity; D013237:Stereoisomerism; D035741:Vernonia / Q000737:chemistry*
C509538:16,17-dihydroxy-ent-kauran-19-oic acid-19-(arabinopyranosyl-1-2-glucopyranosyl) ester; C509537:16-hydroxy-ent-kauran-19-oic acid-19-(arabinopyranosyl-1-2-glucopyranosyl) ester; C509536:8-(4-hydroxymethacryloyloxy)-10-hydroxy-1,13-dimethoxyhirsutinolide; D004187:Disaccharides; D045786:Diterpenes, Kaurane; D006027:Glycosides; D016209:Interleukin-8; D007783:Lactones; D016328:NF-kappa B; D012717:Sesquiterpenes; D004247:DNA