Iridoid glucosides and a C₁₃-norisoprenoid from Lamiophlomis rotata and their effects on NF-κB activation.
Four new iridoid glucosides, 7-dehydroxyzaluzioside (1), 6'-O-syringylphlorigidoside C (2), barlerin-6″-hydroxy-2″,6″-dimethylocta-2″,7″-dienate ester (3), 6β-n-butoxy-7,8-dehydropenstemonoside (4), and a new C(13)-norisoprenoid derivative, 5β,6α-dihydroxy-3β-(β-D-glucoyranosyloxy)-7-megastigmen-9-one (5), together with 16 known iridoid glucosides, were isolated from Lamiophlomis rotata. The structures of these new compounds were elucidated by HRMS, 1D and 2D NMR spectroscopy. A stable nuclear factor kappaB (NF-κB)-luciferase-expressing human embryonic kidney 293 cell line was used in the luciferase assay for monitoring the anti-inflammatory activity of the compounds. It was found that 6β-n-butoxy-7,8-dehydropenstemonoside (4) and two known compounds (8-epi-7-deoxyloganin and 7,8-dehydropenstemonoside) had a significant inhibitory effect on lipopolysaccharide-stimulated NF-κB activation.
Department of Pharmacy, Changzheng Hospital, Second Military Medical University, 415 Fengyang Road, Shanghai 200003, PR China.
Feng
F
Zhang
Zhi-Jun
ZJ
Wu
Lian-na
LN
Sun
Jun
J
Wang
Xia
X
Tao
Wan-Sheng
WS
Chen
D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005809:Genes, Regulator / Q000187:drug effects; D057809:HEK293 Cells; D006801:Humans; D057888:Iridoid Glucosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D019686:Lamiaceae / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000633:toxicity; D008156:Luciferases / Q000235:genetics / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D016328:NF-kappa B / Q000378:metabolism*; D045792:Norisoprenoids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
D000893:Anti-Inflammatory Agents; D057888:Iridoid Glucosides; D008070:Lipopolysaccharides; D016328:NF-kappa B; D045792:Norisoprenoids; D008156:Luciferases