National Research Institute of Chinese Medicine, Ministry of Health and Welfare , No. 155-1, Sec. 2, Li-Nung Street, Peitou, Taipei 11221, Taiwan.
Department of Cosmetic Science, Chang Gung University of Science and Technology , Taoyuan 33302, Taiwan.
J Nat Prod. 2017 Feb 24;80(2):246-253. doi: 10.1021/acs.jnatprod.5b01164. Epub 2017 Feb 7.
Chemical investigation of the rhizomes of Helminthostachys zeylanica led to the isolation of eight new flavonoids including six cyclized geranylflavonoids, ugonins V-X (1-3), (10R,11S)-ugonin N (4), (10R,11S)-ugonin S (5), and ugonin Y (6), as well as two quercetin glucosides, quercetin-4'-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (7) and quercetin-3-O-β-d-glucopyranosyl-4'-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (8). The structures of these compounds were established by spectroscopic analyses and acid hydrolysis of the sugar moiety. Among the isolated compounds, 1, 2, 5, 6, ugonins J-S (9-13), ugonstilbene A (14), and ugonin L (23) were evaluated for their anti-inflammatory activity on lipopolysaccharide-induced nitric oxide (NO) production in microglial cells. Except for 1, 5, and 13, all other compounds inhibited NO production with IC values of 6.2-10.1 μM and were more potent than the positive control, pyrrolidine dithiocarbamate. Compounds 1, 2, 5, 6, and 10-13 were tested for antiosteoporotic activities, and ugonin K (10) exhibited the highest inhibitory activity against RANKL-induced osteoclast differentiation in RAW264.7 cells with an IC value of 1.8 ± 0.2 μM.
从 Helminthostachys zeylanica 的根茎中分离得到了 8 种新的类黄酮化合物，包括 6 种环化香叶基类黄酮，ugonins V-X（1-3）、(10R,11S)-ugonin N（4）、(10R,11S)-ugonin S（5）和 ugonin Y（6），以及 2 种槲皮素葡萄糖苷，槲皮素-4'-O-β-d-吡喃葡萄糖基-(1→2)-β-d-吡喃葡萄糖苷（7）和槲皮素-3-O-β-d-吡喃葡萄糖基-4'-O-β-d-吡喃葡萄糖基-(1→2)-β-d-吡喃葡萄糖苷（8）。这些化合物的结构通过光谱分析和糖部分的酸水解确定。在所分离的化合物中，1、2、5、6、ugonins J-S（9-13）、ugonstilbene A（14）和 ugonin L（23）被评估了对脂多糖诱导的小胶质细胞中一氧化氮（NO）产生的抗炎活性。除了 1、5 和 13，所有其他化合物均抑制 NO 产生，IC 值为 6.2-10.1 μM，比阳性对照吡咯烷二硫代氨基甲酸盐更有效。化合物 1、2、5、6 和 10-13 被测试了抗骨质疏松活性，ugonin K（10）在 RAW264.7 细胞中对 RANKL 诱导的破骨细胞分化表现出最高的抑制活性，IC 值为 1.8 ± 0.2 μM。
