Phenanthrenoids from Juncus acutus L., new natural lipopolysaccharide-inducible nitric oxide synthase inhibitors.
The novel natural product juncutol (1), 1,4,7-trimethyl-8,9-dihydro-4H-cyclopenta[def]phenanthrene-2,6-diol, along with the three related metabolites juncusol (2), dehydrojuncusol (3), and 6-hydroxymethyl-1-methyl-5-vinyl-9,10-dihydrophenanthrene-2-ol (4), were isolated from the rhizomes of Juncus acutus L. (Juncaceae) growing in Egypt. The structural identity of 1 was determined on the basis of spectroscopic analyses, including 2D NMR spectroscopy. The inhibitory effect of these natural products on the expression of inducible nitric oxide synthase (iNOS) in lipopolysaccharide-stimulated RAW264.7 macrophage cells was determined for the first time. The unprecedented symmetrical compound juncutol (1) was found to be the most potent inhibitor against the induction of the proinflammatory iNOS protein.
Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt.
Fathi Abdelmohsen Abdelhalim
FA
Behery
Zain Elabdin Metwally
ZE
Naeem
Galal Taha
GT
Maatooq
Mohamed Mahmoud Abdelfattah
MM
Amer
Zhi-Hong
ZH
Wen
Jyh-Horng
JH
Sheu
Atallah Fouad
AF
Ahmed
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000494:pharmacology; D004534:Egypt; D004591:Electrophoresis, Polyacrylamide Gel; D004791:Enzyme Inhibitors; D008070:Lipopolysaccharides / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors*; D010616:Phenanthrenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018517:Plant Roots / Q000737:chemistry; D010944:Plants / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000894:Anti-Inflammatory Agents, Non-Steroidal; D004791:Enzyme Inhibitors; D008070:Lipopolysaccharides; D010616:Phenanthrenes; D052247:Nitric Oxide Synthase Type II