Natural Product Research ( IF 2.2 ) Pub Date : 2022-11-08 , DOI: 10.1080/14786419.2022.2144301 Rima Konya 1 , Rengin Reis 2 , Hande Sipahi 3 , Anita Barta 4 , Judit Hohmann 4, 5 , Hasan Kırmızıbekmez 1
Abstract
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 PGE2 level comparable to the reference drugs.
中文翻译:
十字花龙胆次生代谢产物及其抗炎镇痛活性
摘要
从Gentiana cruciata L.的地上部分分离出一种先前未报道的环烯醚萜苷,十字花苷 ( 1 ) ,以及 10 种已知化合物 eustomoside ( 2 )、eustomorusside ( 3 )、龙胆苦苷 ( 4 )、6'- O -β-D-吡喃葡萄糖龙胆苦苷 ( 5 )、马钱酸 ( 6 )、异荠草苷 ( 7 )、异牡荆素 ( 8 )、异牡荆素 2'' -(E)-阿魏酸盐( 9 )、芒果苷 ( 10 ) 和 2-甲基肌醇 ( 11 ) 。基于广泛的 1 D 和 2 D NMR 实验以及 HRMS 分析,阐明了分离物的化学结构。评估所有分离株的体外抗炎和镇痛活性。化合物9、4和7 ( 200 µM) 通过抑制 LPS 诱导的 RAW 264.7 巨噬细胞产生亚硝酸盐而表现出中等的抗炎活性,抑制率分别为 39.5%、25.8% 和 22.9%,且没有表现出明显的细胞毒性。此外,1、2、4和7对IL-6水平的降低幅度最大。此外,与参考药物相当,化合物4通过降低PGE 2水平而显示出体外镇痛活性。