Glycosylation of Stilbene Compounds by Cultured Plant Cells
Glycosylation of Stilbene Compounds by Cultured Plant Cells
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DOI：
10.3390/molecules25061437
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发表时间：
2020-03-02
期刊：
影响因子：
4.6
通讯作者：
Hamada, Hiroki
中科院分区：
文献类型：
--
作者：
Shimoda, Kei;Kubota, Naoji;Hamada, Hiroki
氧化白藜芦醇和买麻藤醇是天然存在的二苯乙烯类化合物，具有多种药理活性。这些化合物的水不溶性限制了它们的进一步药理学开发。生物活性化合物的糖基化可以提高其水溶性、理化稳定性、肠道吸收和生物半衰期，并改善其生物学和药理学性质。植物细胞培养是稀有植物繁殖和次生代谢产物生物合成研究的理想体系。此外，各种有机化合物的生物转化已经作为植物细胞培养系统的生物技术应用中的目标进行了研究。培养的植物细胞不仅可以糖基化内源代谢中间产物，还可以糖基化外源物质。在植物中，糖基化反应对降低外源物质的毒性起作用。到目前为止，已经有一些研究通过培养的甘薯和羊角拗植物细胞对外源给予的二苯乙烯化合物在3 '和4 '位置的糖基化进行了研究。但利用培养的植物细胞对二苯乙烯类化合物的2 ' -羟基进行糖基化反应的研究却很少受到关注。在这项工作中，描述了氧化白藜芦醇（3，5，2 '，4' -四羟基芪）通过用培养的商陆细胞生物转化转化为氧化白藜芦醇的3-、2 '-和4 '-β-葡糖苷.另一方面，买麻藤醇（3，5，2 '，6' -四羟基二苯乙烯）通过培养的美洲大蠊细胞转化为买麻藤醇的2 '-β-葡萄糖苷.氧化白藜芦醇2 '-β-葡萄糖苷和买麻藤醇2 '-β-葡萄糖苷是两个新化合物.本文首次报道了二苯乙烯类化合物在培养的植物细胞中的2 ' -位糖基化反应。
Oxyresveratrol and gnetol are naturally occurring stilbene compounds, which have diverse pharmacological activities. The water-insolubility of these compounds limits their further pharmacological exploitation. The glycosylation of bioactive compounds can enhance their water-solubility, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio- and pharmacological properties. Plant cell cultures are ideal systems for propagating rare plants and for studying the biosynthesis of secondary metabolites. Furthermore, the biotransformation of various organic compounds has been investigated as a target in the biotechnological application of plant cell culture systems. Cultured plant cells can glycosylate not only endogenous metabolic intermediates but also xenobiotics. In plants, glycosylation reaction acts for decreasing the toxicity of xenobiotics. There have been a few studies of glycosylation of exogenously administrated stilbene compounds at their 3- and 4 ' -positions by cultured plant cells of Ipomoea batatas and Strophanthus gratus so far. However, little attention has been paid to the glycosylation of 2 ' -hydroxy group of stilbene compounds by cultured plant cells. In this work, it is described that oxyresveratrol (3,5,2 ' ,4 ' -tetrahydroxystilbene) was transformed to 3-, 2 '-, and 4 '-beta -glucosides of oxyresveratrol by biotransformation with cultured Phytolacca americana cells. On the other hand, gnetol (3,5,2 ' ,6 ' -tetrahydroxystilbene) was converted into 2 '-beta -glucoside of gnetol by cultured P. americana cells. Oxyresveratrol 2 '-beta -glucoside and gnetol 2 '-beta -glucoside are two new compounds. This paper reports, for the first time, the glycosylation of stilbene compounds at their 2 ' -position by cultured plant cells.