ABSTRACT
Phytochemical investigation on the fruits of Cydonia oblonga Mill., a traditional Uighur medicine, led to the isolation of seven undescribed and nine known megastigmane glycosides. Their structures including absolute configurations were characterized by an extensive analysis of spectroscopic data including HRESIMS and NMR, combined with ECD calculations. Additionally, compounds 1, 2, 4, and 6-16 exhibited anti-inflammatory activity by inhibiting the secretion of cytokines TNF-α and IL-6 in RAW264.7 cells induced by lipopolysaccharides (LPS) with inhibitory rates of 10.79%-44.58% at 20 µM.
Subject(s)
Cyclohexanones , Glycosides , Lipopolysaccharides , Norisoprenoids , Norisoprenoids/chemistry , Norisoprenoids/pharmacology , Norisoprenoids/isolation & purification , Mice , Glycosides/chemistry , Glycosides/isolation & purification , Glycosides/pharmacology , RAW 264.7 Cells , Animals , Cyclohexanones/chemistry , Cyclohexanones/pharmacology , Cyclohexanones/isolation & purification , Lipopolysaccharides/pharmacology , Lipopolysaccharides/antagonists & inhibitors , Molecular Structure , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Interleukin-6/antagonists & inhibitors , Interleukin-6/metabolism , Tumor Necrosis Factor-alpha/antagonists & inhibitors , Structure-Activity Relationship , Dose-Response Relationship, Drug , GlucosidesABSTRACT
Six undescribed clerodane diterpenoids along with five known ones were isolated from the aerial parts of Salvia deserta, a traditional Uygur medicine. Their chemical structures including absolute configurations were elucidated by extensive spectroscopic analysis (including 1D and 2D NMR, HRESIMS, and IR), combined with calculated ECD method and single-crystal X-ray diffraction analysis. All the compounds possessed a terminal α,ß-unsaturated-γ-lactone moiety, and were assayed for their immunosuppressive activity via inhibiting the secretion of cytokines TNF-α and IL-6 in macrophages RAW264.7. Among them, (5R,8R,9S,10R)-18-nor-cleroda-2,13-dien-16,15-olide-4-one obviously suppressed the secretion of TNF-α and IL-6 with IC50 values of 8.55 and 13.65 µM, respectively.