title: Clerodane diterpenoids from Tinospora sagittata (Oliv.) Gagnep.
abstract: Three new clerodane diterpene glycosides, tinospinosides A (1), B (2), and C (3) were isolated from the roots of Tinospora sagittata (Oliv.) Gagnep. Their structures were determined to be (2 S,4a R,6a R,9 R,10a S,10b S)-2-(3-furanyl)-9-( β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (1), (2 S,4a S,6a R,9 R,10a R,10b S)-2-(3-furanyl)-9-( β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4a-hydroxyl-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (2) and (2 S,4a R,6a R,9 R,10a R,10b S)-2-(3-furanyl)-9-( β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4a-hydroxyl-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (3), by various spectroscopic analyses, chemical reactions, and computer-assisted calculations. The inhibitory activities of NO production by these compounds and their chemical derivatives in lipopolysaccharide and TNF γ-activated macrophage-like cell line J774.1 were tested. Tinospin A, 12- EPI-tinospin A, tinospinoside B, and tinospinoside C showed inhibitory activities of NO production with the IC(50) values of 162, 182, 290, and 218 µM, respectively.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toho University, Funabashi, Chiba, Japan. liwei@phar.toho-u.ac.jp
authors.forename: Wei
authors.initials: W
authors.lastname: Li
authors.forename: Chao
authors.initials: C
authors.lastname: Huang
authors.forename: Songpei
authors.initials: S
authors.lastname: Li
authors.forename: Fenghua
authors.initials: F
authors.lastname: Ma
authors.forename: Qin
authors.initials: Q
authors.lastname: Li
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Asada
authors.forename: Kazuo
authors.initials: K
authors.lastname: Koike
mesh_terms: D000818:Animals; D002460:Cell Line; D004224:Diterpenes / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides; D008264:Macrophages / Q000187:drug effects* / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors*; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology; D018517:Plant Roots; D031610:Tinospora / Q000737:chemistry*; D048069:Tumor Necrosis Factors
chemical_list: D004224:Diterpenes; D008070:Lipopolysaccharides; D010936:Plant Extracts; D048069:Tumor Necrosis Factors; C572589:tinospinoside A; C572592:tinospinoside B; C572591:tinospinoside C; D009569:Nitric Oxide