Structures and In Vitro Antihepatic Fibrosis Activities of Prenylated Dihydrostilbenes and Flavonoids from Glycyrrhiza uralensis Leaves
Structures and In Vitro Antihepatic Fibrosis Activities of Prenylated Dihydrostilbenes and Flavonoids from Glycyrrhiza uralensis Leaves
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乌拉尔甘草叶中异戊二烯化二氢芪和黄酮类化合物的结构及其体外抗肝纤维化活性
DOI：
10.1111/1750-3841.14592
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发表时间：
2019-05-01
影响因子：
3.9
通讯作者：
Ma, Chao-Mei
中科院分区：
文献类型：
--
作者：
Fan, Yu-Hong;Ye, Rigui;Ma, Chao-Mei
甘草是甘草的主要植物来源。为了更好地利用其地上部分，本研究旨在从该植物的叶片中鉴定生物活性物质。对叶的乙醇提取物进行重复层析，得到15种化合物。根据它们的各种光谱数据，确定其结构为三个新的二氢芪类化合物：glycypytilbene A（1），glycydipytilbene（2），glycypytilbene B（3）和12个已知化合物：α，α '-二氢-3，5，4'-三羟基-4，3 '-二异戊烯基芪（4），α，α'-二氢-3，5，3 '，4'-四羟基-2，5 '-二异戊烯基芪（5），6-异戊烯基圣草酚（6）、5 ′-异戊烯基圣草酚（7）、6-异戊烯基槲皮素-3-Me醚（8）、5 ′-异戊烯基槲皮素（9）、6-异戊烯基槲皮素（10）、6-异戊烯基柚皮素（11）、3 ′-异戊烯基柚皮素（12）、S形草素C（13）、8-[（E）-3-羟甲基-2-丁烯基]-圣草酚（14）和槲皮素-3-Me醚（15）。这些化学成分中的大多数抑制α-葡糖苷酶活性，其中两种异戊烯化槲皮素衍生物（9至10）具有最大活性（IC 50 < 4.0 μ g/mL）。化合物1、3至4、6至7、9至12阻碍人肝星状细胞的生长，其中异戊二烯化的类黄酮（6至7、9至12）比它们的未异戊二烯化的对应物更稳健。实际应用本研究发现，甘草叶中含有异戊二烯化二氢芪类化合物和黄酮类化合物，对α-葡萄糖苷酶和人肝星状细胞的增殖具有抑制作用，这将促进甘草的发展。甘草叶是具有抗糖尿病或预防肝纤维化作用的健康产品。
Glycyrrhiza uralensis is the major plant source of licorice. This study was to identify bioactive compounds from the plant's leaves in order to make better use of its aerial part. An ethanol extract of the leaves was subjected to repeated chromatography to yield 15 compounds. The structures were determined to be three novel dihydrostilbenes, based on their various spectroscopic data-glycypytilbene A (1), glycydipytilbene (2), and glycypytilbene B (3)-and 12 known compounds, alpha,alpha '-dihydro-3,5,4 '-trihydroxy-4,3 '-diisopentenylstilbene (4), alpha,alpha '-dihydro-3,5,3 ',4 '-tetrahydroxy-2,5 '-diisopentenylstilbene (5), 6-prenyleriodictyol (6), 5 '-prenyleriodictyol (7), 6-prenylquercetin-3-Me ether (8), 5 '-prenylquercetin (9), 6-prenylquercetin (10), 6-prenylnaringenin (11), 3 '-prenylnaringenin (12), sigmoidin C (13), 8-[(E)-3-hydroxymethyl-2- butenyl]-eriodictyol (14), and quercetin-3-Me ether (15). Most of these chemical constituents inhibited alpha-glucosidase activity, with the two prenylated quercetin derivatives (9 to 10) being the greatest active (IC50 < 4.0 mu g/mL). Compounds 1, 3 to 4, 6 to 7, 9 to 12 impeded the growth of human hepatic stellate cells, with the prenylated flavonoids (6 to 7, 9 to 12) being more robust than their unprenylated counterparts. Practical Applications This study found that Glycyrrhiza uralensis leaves contain prenylated dihydrostilbenes and flavonoids with inhibiting effects on alpha-glucosidase and on the proliferation of human hepatic stellate cells, which should prompt the development of G. uralensis leaves for healthy products with anti-diabetic or liver fibrosis-preventing effects.