[砂仁果实中的萜类化合物及其降血糖活性]
[Terpenoids from fruits of Amomum villosum and their hypoglycemic activity].
作者信息
Ding Min, Wu Sheng-Li, He Xiao-Feng, Zhang Xue-Mei, Geng Chang-An
机构信息
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany,Chinese Academy of Sciences Kunming 650201, China University of Chinese Academy of Sciences Beijing 100049, China.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany,Chinese Academy of Sciences Kunming 650201, China School of Life Sciences, Yunnan University Kunming 650500, China.
出版信息
Zhongguo Zhong Yao Za Zhi. 2022 Nov;47(21):5849-5854. doi: 10.19540/j.cnki.cjcmm.20220411.203.
Eight terpenoids were isolated from the fruits of Amomum villosum by silica gel, Sephadex LH-20, Rp-C_(18), MCI GEL CHP20 P column chromatography, preparative TLC, and HPLC. Their structures were identified by HR-ESI-MS, 1H and ~(13)C-NMR, IR, UV, [α]_D, and ECD spectroscopic data as kravanhin A 3-O-β-D-glucopyranoside(1), kravanhin B(2), 6-eudesmene-1β,4β-diol(3), oplodiol(4), vicodiol(5),(1R,2S,4R,7S)-vicodiol 9-O-β-D-glucopyranoside(6),(1R,2S,4S,5R)-angelicoidenol 2-O-β-D-glucopyranoside(7), and(1S,2S,4R,6S)-bornane-2,6-diol 2-O-β-D-glucopyranoside(8). Compound 1 was a new compound, and compounds 2-5 were isolated from A. villosum for the first time. Their hypoglycemic activity was tested based on STC-1 cell model and two enzymatic models(GPa and PTP1 B). The results showed that compounds 1, 7, and 8 could stimulate GLP-1 with the secretion rates of 692.8%, 398.6%, and 483.3% at 25.0 μmol·L(-1), and compound 6 showed inhibitory activity against GPa with an IC_(50) value of 78.6 μmol·L~(-1).
通过硅胶柱色谱、葡聚糖凝胶LH-20柱色谱、反相C₁₈柱色谱、MCI GEL CHP20 P柱色谱、制备薄层色谱和高效液相色谱从阳春砂果实中分离得到8个萜类化合物。通过高分辨电喷雾电离质谱、¹H和¹³C核磁共振谱、红外光谱、紫外光谱、比旋光度和电子圆二色光谱数据鉴定它们的结构分别为缩砂苷A 3-O-β-D-吡喃葡萄糖苷(1)、缩砂苷B(2)、6-桉叶-1β,4β-二醇(3)、蛇床二醇(4)、维考二醇(5)、(1R,2S,4R,7S)-维考二醇9-O-β-D-吡喃葡萄糖苷(6)、(1R,2S,4S,5R)-当归素醇2-O-β-D-吡喃葡萄糖苷(7)和(1S,2S,4R,6S)-冰片-2,6-二醇2-O-β-D-吡喃葡萄糖苷(8)。化合物1为新化合物，化合物2 - 5为首次从阳春砂中分离得到。基于STC-1细胞模型和两种酶模型（葡萄糖磷酸酶和蛋白酪氨酸磷酸酶1B）对它们的降血糖活性进行了测试。结果表明，化合物1、7和8在25.0 μmol·L⁻¹时可刺激胰高血糖素样肽-1分泌，分泌率分别为692.8%、398.6%和483.3%，化合物6对葡萄糖磷酸酶具有抑制活性，半数抑制浓度值为78.6 μmol·L⁻¹。
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