Chemical constituents of malagasy liverworts, part V: prenyl bibenzyls and clerodane diterpenoids with nitric oxide inhibitory activity from Radula appressa and Thysananthus spathulistipus.
3Beta,4beta:15,16-diepoxy-13(16),14-clerodadiene (1) and a new clerodane diterpenoid designated thysaspathone (2) were isolated from the liverwort Thysananthus spathulistipus, while Radula appressa produced radulannin A (3), radulannin L (4), 2-geranyl-3,5-dihydroxybibenzyl (5), 2(S)-2-methyl-2-(4-methyl-3-pentenyl)-7-hydroxy-5-(2-phenylethyl) chromene (o-cannabichromene) (6), 6-hydroxy-4-(2-phenylethyl) benzofuran (7), and o-cannabicyclol (8). All of the isolated compounds inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and the greatest inhibition was attributed to compound 5, with an IC50 value of 4.5 microM.
Harinantenaina
Liva
L
Faculty of Pharmaceutical Sciences, Tokushima Bunri University; Yamashiro-cho, Tokushima 770-8514, Japan.
Takahara
Yusuke
Y
Nishizawa
Takashi
T
Kohchi
Chie
C
Soma
Gen-Ichiro
G
Asakawa
Yoshinori
Y
D000818:Animals; D001632:Bibenzyls / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D002478:Cells, Cultured; D045785:Diterpenes, Clerodane / Q000737:chemistry* / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical; D035926:Hepatophyta / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D009387:Neoprene / Q000737:chemistry* / Q000494:pharmacology; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000737:chemistry
D001632:Bibenzyls; D045785:Diterpenes, Clerodane; C016077:prenyl; D009569:Nitric Oxide; D009387:Neoprene