Natural Product Communications ( IF 1.5 ) Pub Date : 2020-09-17 , DOI: 10.1177/1934578x20944666 Yuya Fujitaka 1 , Hiroki Hamada 1 , Hatsuyuki Hamada 2 , Takafumi Iwaki 3 , Kei Shimoda 4 , Yuya Kiriake 5 , Tomohiro Saikawa 6
Glucosyltransferase from Phytolacca americana (Phytolaccaceae), glucosylated α-tocopherol, daidzein, resveratrol, hesperetin, naringenin, and chrysin to α-tocopherol 6-β-d-glucoside, daidzein 7-β-d-glucoside, resveratrol 3-β-d-glucoside, hesperetin 7-β-d-glucoside, naringenin 7-β-d-glucoside, and chrysin 7-β-d-glucoside, respectively. The antiallergic activity of the glycosides and their aglycons was examined by an in vivo immunoglobulin E (IgE) antibody formation-suppression bioassay using rat. It was found that α-tocopherol 6-β-d-glucoside showed much higher antiallergic activity against glutenin than the positive control, hydrocortisone. On the other hand, daidzein 7-β-d-glucoside had much higher antiallergic activity toward 7S-globulin than hydrocortisone. These glycosides inhibited O2 − generation from rat neutrophils, which leads to the suppression of histamine release from rat peritoneal mast cells, resulting in the decrease of IgE antibody formation in rat. Chrysin 7-β-d-glucoside had stronger antityrosinase activity than chrysin. Cultured P. americana cells regioselectively introduced methoxyl and glucosyl residues on exogenously administrated chrysin to give 8-methoxychrysin and chrysin 7-β-d-glucoside. This is the first report on methoxylation of flavone compound at its eighth position by cultured plant cells.
中文翻译:
α-生育酚,大豆苷元,白藜芦醇,橙皮苷,柚皮素和菊花素的糖苷的合成作为抗过敏功能食品和化妆品
从葡糖美洲商陆(商陆),糖化α生育酚,大豆黄素,白藜芦醇,橙皮素,柚皮素,白杨素和α到生育酚6-β- d葡糖苷,黄豆苷原7-β- d葡糖苷,白藜芦醇3-β- d -葡糖苷,橙皮素7-β- d-葡糖苷,柚皮素7-β- d-葡糖苷和chrysin7-β- d-葡糖苷。使用大鼠通过体内免疫球蛋白E(IgE)抗体形成抑制生物测定法检查了糖苷及其苷元的抗过敏活性。发现α-生育酚6-β- d-葡萄糖苷对谷蛋白的抗过敏活性远高于阳性对照氢化可的松。另一方面,黄豆苷元7-β- d-葡糖苷对7S-球蛋白的抗过敏活性比氢化可的松高。这些甙抑制ö 2 -来自大鼠嗜中性粒细胞,产生导致的组胺释放的从大鼠腹膜肥大细胞,导致IgE抗体的形成在大鼠的降低抑制。菊花链7-β- d-葡萄糖苷的抗酪氨酸酶活性比菊花链强。培养的美洲P.细胞在外源施用的菊花素上区域选择性地引入甲氧基和葡糖基残基,得到8-甲氧基菊花素和菊花素7-β- d-葡萄糖苷。这是关于培养的植物细胞在其第八位置上的黄酮化合物的甲氧基化的首次报道。