Anti-austeric Activity of Phenolic Constituents of Seeds of Arctium lappa
Anti-austeric Activity of Phenolic Constituents of Seeds of Arctium lappa
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DOI：
10.1177/1934578x1300800414
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发表时间：
2013-04
影响因子：
1.8
通讯作者：
Y. Tezuka;Kei-ichi Yamamoto;S. Awale;Feng Li;S. Yomoda;S. Kadota
中科院分区：
文献类型：
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作者：
Y. Tezuka;Kei-ichi Yamamoto;S. Awale;Feng Li;S. Yomoda;S. Kadota
从牛蒡（Arctium lappa L.）（菊科），我们得到了牛蒡苷元（1）、牛蒡苷（2）、绿原酸（3）、4，5-二咖啡酰奎宁酸（4）、3，5-二咖啡酰奎宁酸（5）、3，4-二咖啡酰奎宁酸（6）、matairesinol（11）、异拉帕酚A（12）、拉帕酚F（14）和拉帕酚B（15），以及1：1异拉帕酚C（7）与拉帕酚C（8）、牛蒡子苷E（9）与牛蒡子苷D（10）、12与拉帕酚A（13）的混合物;通过厌氧微生物代谢1，得到3′-二-O-去甲基-4 ′-去羟基牛蒡子苷元（17）和3-O-去甲基牛蒡子苷元（18）。然后，我们评估了这些纯化合物和1：1混合物，连同肠二醇（19）和肠内酯（20），对人胰腺癌PANC-1细胞在营养剥夺培养基（NDM）中的体外优先细胞毒活性。其中，1和18表现出强活性，其PC 50值分别为1.75和4.38 μ M，而11、15和17表现出弱活性，其PC 50值分别为31.1、30.9和38.7 μ M。通过比较它们的结构和PC 50值，可以得出以下结构部分对于1的优先细胞毒性是重要的：1）γ-丁内酯环上2位的3-羟基-4-甲氧基苯基，2）γ-丁内酯环上3位的极性较小的取代基，和3）γ-丁内酯环。
From seeds of Arctium lappa L. (Asteraceae) we obtained arctigenin (1), arctiin (2), chlorogenic acid (3), 4,5-dicaffeoylquinic acid (4), 3,5-dicaffeoylquinic acid (5), 3,4-dicaffeoylquinic acid (6), matairesinol (11), isolappaol A (12), lappaol F (14), and lappaol B (15), together with 1:1 mixtures of isolappaol C (7) and lappaol C (8), arctignan E (9) and arctignan D (10), and 12 and lappaol A (13), while 3,3′,4′-tri-O-demethylarctigenin (16), 3,3′-di-O-demethyl-4′-dehydroxyarctigenin (17), and 3-O-demethylarctigenin (18) were obtained by anaerobic microbiological metabolism of 1. Then, we evaluated the in vitro preferential cytotoxic activity of these pure compounds and 1:1 mixtures, together with enterodiol (19) and enterolactone (20), against human pancreatic cancer PANC-1 cells in nutrient-deprived medium (NDM). Among them, 1 and 18 showed potent activity, with PC50 values of 1.75 and 4.38 μ M, respectively, while 11, 15, and 17 showed mild activity with PC50 values of 31.1, 30.9, and 38.7 μ/M, respectively. By comparing their structures and PC50 values, the following structural moieties could be concluded to be important for the preferential cytotoxicity of 1: 1) the 3-hydroxy-4-methoxyphenyl group at the 2-position on the γ-butyrolactone ring, 2) the less polar substituent at the 3-position on the γ-butyrolactone ring, and 3) the γ-butyrolactone ring.