Abstract

A new megastigmane glycoside, (3S,4R,7E)-megastigma-5,7-diene-9-one-3,4-diol 3-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside (1) and a new cyanogenic glycosyl derivative, (S)-2-(6′-O-R-rosmarinoyl-β-D-glucopyranosyloxy)-phenylacetonitrile (2) were isolated from the methanol extract of the Elsholtzia ciliata together with twelve known compounds, 1-O-β-D-glucopyranosyl-2-hydroxy-4-allylbenzene (3), citrusin C (4), 1,2-di-O-β-D-glucopyranosyl-4-allylbenzene (5), manglieside B (6), 4-allyl-2-hydroxyphenyl 1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (7), (-)-isolariciresinol 3α-β-D-glucopyranoside (8), 7R,8R-threo-4,7,9-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan-9′-O-β-D-glucopyranoside (9), 7R,8R-threo-4,7,9,9′-tetrahydroxy-3-methoxy-8-O-4′-neolignan-9′-O-β-D-glucopyranoside (10), cedrusin-4-O-β-D-glucopyranoside (11), icariside E₃ (12), everlastoside L (13) and rosmarinic acid (14). Their chemical structures were elucidated on the basic of extensive 1D and 2D-NMR experiments, as well as their mass spectroscopic data. The absolute configurations of the compounds 1 and 2 were successfully indicated by both theoretical and calculated CD spectra. Compounds 3–7, 9 and 10 potential inhibited NO production in LPS-activated RAW264.7 cells with IC₅₀ values of 6.71, 8.97, 12.38, 14.27, 16.13, 13.54, 16.27 µM, respectively, compared to that of the positive control of N^G-monomethyl-L-arginine acetate (L-NMMA), IC₅₀ = 32.51 µM.

摘要

一种新的巨豆苷，(3 S ,4 R, 7 E) -megastigma-5,7-diene-9-one-3,4-diol 3 -O-β -D-apiofuranosyl-(1→2)- β从香薷甲醇提取物中分离出-D-吡喃葡萄糖苷 ( 1 ) 和一种新的氰基糖基衍生物 ( S )-2-(6′ -OR-迷迭香酰基- β -D-吡喃葡萄糖氧基)-苯基乙腈 ( 2 )与十二种已知化合物，1 -O-β -D-吡喃葡萄糖基-2-羟基-4-烯丙基苯（3），柑橘素C（4），1,2-二-O-β- D-吡喃葡萄糖基-4-烯丙基苯（5 ), manglieside B ( 6 ), 4-烯丙基-2-羟基苯基 1 -O -β -D-apiofuranosyl-(1→6)- β -D-吡喃葡萄糖苷 ( 7 ), (-)-异落叶松树脂醇 3α- β - D-吡喃葡萄糖苷 ( 8 ), 7 R ,8 R -苏型-4,7,9-三羟基-3,3'-二甲氧基-8 -O- 4'-新木脂素-9' -O-β -D-吡喃葡萄糖苷 ( 9 ), 7 R ,8 R -苏型-4,7,9,9'-四羟基-3-甲氧基-8 -O- 4'-新木脂素-9' -O-β -D-吡喃葡萄糖苷 ( 10 ), 雪松素-4 -O-β -D-吡喃葡萄糖苷 ( 11 )、淫羊藿苷 E ₃ ( 12 )、everlastoside L ( 13 ) 和迷迭香酸 ( 14 )。它们的化学结构是在广泛的一维和二维核磁共振实验以及质谱数据的基础上阐明的。理论和计算CD光谱成功地表明了化合物1和2的绝对构型。与阳性对照相比，化合物3 – 7、9和10可能抑制 LPS 激活的 RAW264.7 细胞中 NO 的产生，IC 50_{值分别为 6.71、8.97、12.38、14.27、16.13、13.54、16.27 µM} NG-^单甲基-L-精氨酸乙酸酯 (L-NMMA)，IC ₅₀ = 32.51 µM。