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A previously unreported secoiridoid glycoside, cruciatoside ( 1 ) was isolated from the aerial parts of  Gentiana cruciata  L. along with ten known compounds eustomoside ( 2 ), eustomorusside ( 3 ), gentiopicroside ( 4 ), 6'- O -β-D-glucopyranosyl gentiopicroside ( 5 ), loganic acid ( 6 ), isoorientin ( 7 ), isovitexin ( 8 ), isovitexin 2'' -(E)- ferulate ( 9 ), mangiferin ( 10 ), and 2-methyl-inositol ( 11 ). The chemical structures of the isolates were elucidated based on extensive 1 D and 2 D NMR experiments as well as HRMS analysis. All isolates were evaluated for their  in vitro  anti-inflammatory and analgesic activities. Compounds  9 ,  4 , and  7  (200 µM) showed moderate anti-inflammatory activity by inhibiting nitrite production from LPS-induced RAW 264.7 macrophage cells, with the inhibition rates of 39.5%, 25.8% and 22.9% respectively without exhibiting substantial cytotoxicity. Besides,  1 ,  2 ,  4 , and  7  exerted the highest decrease in IL-6 levels. Moreover, compound  4  showed  in vitro  analgesic activity by decreasing the PGE 2  level comparable to the reference drugs.

Secondary metabolites from Gentiana cruciata L. and their anti-inflammatory and analgesic activities