ABSTRACT
Aerial parts of Daphne oleoides Schreber ssp. oleoides (Thymelaeaceae) are used to treat rheumatoid arthritis and lumbago in Turkish folk medicine. In order to evaluate folkloric utilization, in vitro inhibitory effects of the ethyl acetate extract and fractions obtained from this extract on interleukin 1 (IL-1alpha, IL-1beta) and tumour necrosis factor (TNF-alpha) biosynthesis were studied. Through chemical isolation techniques and activity-guided fractionation process, seventeen compounds were isolated and their structures were elucidated (numbered 1-17). Diterpenoids genkwadaphnin (3) and 1,2-dehydrodaphnetoxin (6) and a coumarin derivative daphnetin (9) showed potent inhibitory activity and were found to be the main active ingredients. Furthermore, gnidilatin (4), gnidilatin-20 palmitate (5), genkwadaphnin-20-palmitate (7) and gnidicin-20-palmitate (8), having diterpenoid structure, and eudesmine (12), wikstromol (13) and matairesinol (14), having lignan structure, were determined to possess moderate inhibitory activity and may have a contributory role in the effect of the remedy.
Subject(s)
Cytokines/metabolism , Plant Extracts/pharmacology , Acetates/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Diterpenes/pharmacology , Dose-Response Relationship, Drug , Enzyme-Linked Immunosorbent Assay , Free Radical Scavengers/pharmacology , Furans/pharmacology , Humans , Interleukin-1/biosynthesis , Interleukin-1/blood , Lignans/pharmacology , Models, Chemical , Plants, Medicinal/chemistry , Tumor Necrosis Factor-alpha/biosynthesis , Umbelliferones/pharmacologyABSTRACT
From the fresh stem of Stephanotis lutchuensis var. japonica, five new oleanane-type triterpenoid glycosides named sitakisosides VI-X (1-5) were isolated. Their structures were determined on the basis of spectroscopic data and chemical evidence. Sitakisosides VI and VII are 3-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranosyl(1-->6)-beta-D- glucopyranosido-21-O-(6-N-methylanthranilyl)-beta-D-glucopyr anosyl and 3-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranosyl(1-->6)-beta-D- glucopyranosido-21-O-(4-N-methylanthranilyl)-beta-D-glucopyr anosyl sitakisogenin, respectively. Sitakisoside VIII is 3-O-beta-D-xylopyranosyl(1-->6)-beta-D- glucopyranosyl(1-->6)-beta-D-glucopyranosido-21-O-N-methylanthr anilyl- 3 beta,16 beta,21 beta,28-tetrahydroxyolean-12-ene-22-one. Sitakisoside IX is 3-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranosyl(1-->6)-beta-D- glucopyranosido-21-O-(6-N-methylanthranilyl)-beta-D-glucopyr anosyl gymnestrogenin. Sitakisoside X is 3-O-beta-D-xylopyranosyl(1-->6)-beta-D- glucopyranosyl(1-->6)-beta-D-glucopyranosyl longispinogenin.
Subject(s)
Flavoring Agents/chemical synthesis , Glycosides/chemical synthesis , Plant Stems/chemistry , Plants/chemistry , Triterpenes/chemical synthesis , Flavoring Agents/pharmacology , Glycosides/pharmacology , Humans , Molecular Conformation , Sucrose/antagonists & inhibitors , Sucrose/pharmacology , Taste/drug effects , Triterpenes/pharmacologyABSTRACT
From the fresh stem of Stephanotis lutchuensis var. japonica, we have isolated five new oleane glycosides named sitakisosides I-V (1-5). Their structures were determined on the basis of spectroscopic data and chemical evidence. Sitakisoside V showed the strongest antisweet activity among sitakisosides I-V.
