Synthesis and pharmacological evaluation of glycosides of resveratrol, pterostilbene, and piceatannol
Synthesis and pharmacological evaluation of glycosides of resveratrol, pterostilbene, and piceatannol
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DOI：
10.1111/nyas.12836
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发表时间：
2015-01-01
期刊：
影响因子：
--
通讯作者：
Hamada, Hiroki
中科院分区：
文献类型：
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作者：
Shimoda, Kei;Kubota, Naoji;Hamada, Hiroki
为了提高它们的水溶性和药理活性，芪类化合物白藜芦醇、紫檀芪和云杉醇通过培养细胞和环糊精葡聚糖转移酶（CGTase）被糖基化为它们的单葡萄糖苷（β-葡萄糖苷）和二糖苷（β-麦芽糖苷）。美洲商陆培养细胞和葡萄糖基转移酶（PaGT）能够将白藜芦醇葡萄糖基化为3-和4 '-β-葡萄糖苷。Pterostilbene被P.美洲细胞在三种底物中，云杉醇最容易转化为云杉醇4 '-β-葡萄糖苷，产率最高。白藜芦醇的3-和4 '-β-葡萄糖苷通过CGTase进一步糖基化，得到3-和4'-β-麦芽糖苷衍生物。通过β-葡萄糖基化和/或β-麦芽糖基化（即，白藜芦醇的3-和4 ′-β-葡糖苷、白藜芦醇的3-和4 ′-β-麦芽糖苷以及紫檀芪的4 ′-β-葡糖苷对组胺释放的抑制活性分别高于相应的糖苷配基、白藜芦醇和紫檀芪的抑制活性）。此外，白藜芦醇和紫檀芪的磷酸二酯酶（PDE）抑制活性通过β-葡糖基化和/或β-麦芽糖基化（即，白藜芦醇的3-和4 ′-β-葡萄糖苷、白藜芦醇的4 ′-β-麦芽糖苷和紫檀芪的4 ′-β-葡萄糖苷的PDE抑制活性分别高于相应的糖苷配基、白藜芦醇和紫檀芪的PDE抑制活性）。
To enhance their water solubility and pharmacological activities, the stilbenes resveratrol, pterostilbene, and piceatannol were glycosylated to their monoglucosides (beta-glucosides) and diglycosides (beta-maltosides) by cultured cells and cyclodextrin glucanotransferase (CGTase). Cultured cells of Phytolacca americana and glucosyltransferase (PaGT) were capableof glucosylationof resveratrol toits 3-and 4'-beta-glucosides. Pterostilbenewas slightly transformedintoits 4'-beta-glucoside byP. americana cells. Piceatannolwas readily converted into piceatannol 4'-beta-glucoside, with the highest yield among the three substrates. The 3-and 4'-beta-glucosides of resveratrol were subjected to further glycosylation byCGTase to give 3- and 4'-beta-maltoside derivatives. The inhibitory action of resveratrol and pterostilbene toward histamine release induced with compound 48/80 from rat peritonealmast cells was improved by beta-glucosylation and/or beta-maltosylation (i.e., the inhibitory activity for histamine release of the 3- and 4'-beta-glucosides of resveratrol, the 3- and 4'-beta-maltosides of resveratrol, and the 4'-beta-glucoside of pterostilbene was higher than that of the corresponding aglycones, resveratrol and pterostilbene, respectively). In addition, the phosphodiesterase (PDE) inhibitory activity of resveratrol and pterostilbene was enhanced by beta-glucosylation and/or beta-maltosylation (i.e., the PDE inhibitory activities of the 3- and 4'-beta-glucosides of resveratrol, the 4'-beta-maltoside of resveratrol, and the 4'-beta-glucoside of pterostilbene were higher than those of the corresponding aglycones, resveratrol and pterostilbene, respectively).