ABSTRACT
One new canthinone glycoside (1), together with six known compounds (2-7) including three lignans (2-4), two coumarins (5-6) and one phenol (7) was isolated from the root barks of Ailanthus altissima. The structure of new compound 1 was established by the interpretation of UV, IR, MS and NMR data, while its absolute configuration was determined by acid hydrolysis and GIAO NMR calculations with DP4+ probability analysis. The inhibitory effects of all compounds on Nitric oxide (NO) production were investigated in lipopolysaccharide (LPS)-induced RAW 264.7 cells. Results showed that compounds 2 and 5 displayed NO production inhibitory activity with IC50 values of 30.1 and 15.3 µM, respectively.
Subject(s)
Ailanthus , Glycosides , Lipopolysaccharides , Nitric Oxide , Plant Bark , Plant Roots , Ailanthus/chemistry , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Mice , Molecular Structure , Animals , Plant Bark/chemistry , Plant Roots/chemistry , RAW 264.7 Cells , Glycosides/pharmacology , Glycosides/chemistry , Glycosides/isolation & purification , Lipopolysaccharides/pharmacology , Lignans/pharmacology , Lignans/chemistry , Lignans/isolation & purification , Drugs, Chinese Herbal/pharmacology , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/isolation & purification , Coumarins/pharmacology , Coumarins/chemistry , Coumarins/isolation & purification , Nuclear Magnetic Resonance, BiomolecularABSTRACT
Three new monomeric (1-3) and two newdimeric guaianolides (4 and 5), along with three known analogues (6-8) were isolated from the aerial part of Achillea alpina L. Compounds 1-3 were three novel 1,10-seco-guaianolides, while 4 and 5 were two novel 1,10-seco-guaianolides involved heterodimeric [4 + 2] adducts. The new structures were elucidated by analysis of spectroscopic data and quantum chemical calculations. All isolates were evaluated for their hypoglycemic activity with a glucose consumption model in palmitic acid (PA)-induced HepG2-insulin resistance (IR) cells, and compound 1 showed the most promising activity. A mechanistic study revealed that compound 1 appeared to mediate hypoglycemic activity via inhibition of the ROS/TXNIP/NLRP3/caspase-1 pathway.