来自风信子的含氮呋喃糖和吡喃糖类似物。

Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.

作者信息

Asano N, Kato A, Miyauchi M, Kizu H, Kameda Y, Watson A A, Nash R J, Fleet G W

机构信息

Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa 920-11, Japan.

出版信息

J Nat Prod. 1998 May;61(5):625-8. doi: 10.1021/np9705726.

DOI:10.1021/np9705726

PMID:9599261

Abstract

Aqueous methanol extracts from the bulbs of Hyacinthusorientalis were subjected to various ion-exchange column chromatographic steps to give 2(R),5(R)-bis(hydroxymethyl)-3(R),4(R)-dihydroxypyrrolidine (DMDP) (1), 2,5-dideoxy-2,5-imino-dl-glycero-d-manno-heptitol (homoDMDP) (2), 2,5-imino-2,5,6-trideoxy-d-manno-heptitol (6-deoxy-homoDMDP) (3), 2,5-imino-2,5,6-trideoxy-d-gulo-heptitol (4), 1-deoxynojirimycin (5), 1-deoxymannojirimycin (6), alpha-homonojirimycin (7), beta-homonojirimycin (8), alpha-homomannojirimycin (9), beta-homomannojirimycin (10), and 7-O-beta-d-glucopyranosyl-alpha-homonojirimycin (MDL 25,637) (11). The structures of the new natural products 3 and 4 were determined by spectroscopic analysis, including extensive 1D and 2D NMR studies. Compound 2 was found to be a potent inhibitor of bacterial beta-glucosidase, mammalian beta-galactosidases, and mammalian trehalases, while 3 was a potent inhibitor of rice alpha-glucosidase and rat intestinal maltase. Compound 4 was observed to be a good inhibitor of alpha-l-fucosidase.

摘要

对风信子鳞茎的甲醇水提取物进行了各种离子交换柱色谱步骤，得到了2(R),5(R)-双(羟甲基)-3(R),4(R)-二羟基吡咯烷(DMDP)(1)、2,5-二脱氧-2,5-亚氨基-dl-甘油-d-甘露庚糖醇(高同型DMDP)(2)、2,5-亚氨基-2,5,6-三脱氧-d-甘露庚糖醇(6-脱氧-高同型DMDP)(3)、2,5-亚氨基-2,5,6-三脱氧-d-古洛庚糖醇(4)、1-脱氧野尻霉素(5)、1-脱氧甘露野尻霉素(6)、α-高同型野尻霉素(7)、β-高同型野尻霉素(8)、α-高同型甘露野尻霉素(9)、β-高同型甘露野尻霉素(10)以及7-O-β-d-吡喃葡萄糖基-α-高同型野尻霉素(MDL 25,637)(11)。新天然产物3和4的结构通过光谱分析确定，包括广泛的一维和二维核磁共振研究。发现化合物2是细菌β-葡萄糖苷酶、哺乳动物β-半乳糖苷酶和哺乳动物海藻糖酶的有效抑制剂，而化合物3是水稻α-葡萄糖苷酶和大鼠肠道麦芽糖酶的有效抑制剂。观察到化合物4是α-L-岩藻糖苷酶的良好抑制剂。