College of Pharmacy, Chungnam National University, Daejeon, Republic of Korea.
Bioorg Med Chem Lett. 2011 Mar 15;21(6):1777-81. doi: 10.1016/j.bmcl.2011.01.066. Epub 2011 Jan 22.
One new ursane-type triterpenoid glycoside, asiaticoside G (1), five triterpenoids, asiaticoside (2), asiaticoside F (3), asiatic acid (4), quadranoside IV (5), and 2α,3β,6β-trihydroxyolean-12-en-28-oic acid 28-O-[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl] ester (6), and four flavonoids, kaempferol (7), quercetin (8), astragalin (9), and isoquercetin (10) were isolated from the leaves of Centella asiatica. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. The structure of new compound 1 was determined to be 2α,3β,23,30-tetrahydroxyurs-12-en-28-oic acid 28-O-[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl] ester. The anti-inflammatory activities of the isolated compounds were investigated on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Asiaticoside G (1) potently inhibited the production of nitric oxide and tumor necrosis factor-α with inhibition rates of 77.3% and 69.0%, respectively, at the concentration of 100 μM.
从积雪草中分离得到一个新的五环三萜糖苷化合物积雪草苷 G（1），以及五个三萜类化合物，积雪草苷（2）、积雪草苷 F（3）、积雪草酸（4）、槐糖苷 IV（5）和 2α,3β,6β-三羟基齐墩果-12-烯-28-酸 28-O-[α-L-鼠李吡喃糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基]酯（6），以及四个黄酮类化合物，山奈酚（7）、槲皮素（8）、杨梅素（9）和异槲皮苷（10）。它们的化学结构通过质谱、1D 和 2D 核磁共振（NMR）光谱鉴定。新化合物 1 的结构被确定为 2α,3β,23,30-四羟基乌苏-12-烯-28-酸 28-O-[α-L-鼠李吡喃糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基]酯。对分离得到的化合物进行了抗炎活性研究，在 LPS 刺激的 RAW 264.7 细胞中进行。积雪草苷 G（1）在 100μM 浓度下，对一氧化氮和肿瘤坏死因子-α的产生具有显著的抑制作用，抑制率分别为 77.3%和 69.0%。
