Isolation of glycosidase-inhibiting hyacinthacines and related alkaloids from Scilla socialis
Isolation of glycosidase-inhibiting hyacinthacines and related alkaloids from Scilla socialis
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DOI：
10.1021/np0700826
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发表时间：
2007-06-01
影响因子：
5.1
通讯作者：
Nash, Robert J.
中科院分区：
文献类型：
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作者：
Kato, Atsushi;Kato, Noriko;Nash, Robert J.
对水葫芦鳞茎进行检查，分离出11种风信子、2种吡咯烷和3种哌啶类植物。新生物碱的结构经波谱鉴定为：β-1-C-乙基脱氧甘露糖苷(5)、风信子B-7(10)、C-2(11)、C-3(12)、C-4(13)、C-5(14)和α-5-C-(3-羟基丁基)风信子A(2)(15)。虽然β-L-高亲和素(3)和α-7-脱氧高亲和素(α-7-脱氧-HNJ，4)是已知的生物碱，但它们在风信子科植物中的分布尚属首次报道。生物碱11对细菌β-葡萄糖苷酶和人胎盘α-L岩藻糖苷酶有较好的抑制作用，其IC50值分别为13和17mU M；生物碱12对α-L岩藻糖苷酶无抑制作用，但对牛肝β-半乳糖苷酶的抑制作用比11更强(IC_(50)=52mU M)。生物碱13和14对哺乳动物α-葡萄糖苷酶有抑制作用(IC_(50)分别为45和77mU M)，生物碱14对细菌β-葡萄糖苷酶有中等抑制作用(IC_(50)=48 mU M)。
An examination of the bulbs of Scilla socialis has resulted in the isolation of 11 hyacinthacines, two pyrrolidines, and three piperidines. The structures of the new alkaloids were elucidated by spectroscopic methods as beta-1-C-ethyldeoxymannojirimycin (5), hyacinthacines B-7 (10), C-2 (11), C-3 (12), C-4 (13), and C-5 (14), and alpha-5-C-(3-hydroxybutyl)hyacinthacine A(2) (15). Although, beta-L-homofuconojirimycin (3) and alpha-7-deoxyhomonojirimycin (alpha-7-deoxy-HNJ, 4) are previously known alkaloids, this is the first report of their occurrence in the plant family Hyacinthaceae. Alkaloid 11 was found to be a good inhibitor of bacterial beta-glucosidase and human placenta alpha-l-fucosidase, with IC50 values of 13 and 17 mu M, respectively, while alkaloid 12 showed no inhibitory activity toward alpha-l-fucosidase but was a more potent inhibitor of bovine liver beta-galactosidase (IC50 = 52 mu M) than 11. Alkaloids 13 and 14 were shown to be inhibitory toward mammalian alpha-glucosidase (IC50 = 45 and 77 mu M, respectively), and alkaloid 14 was demonstrated as a moderate inhibitor of bacterial beta-glucosidase (IC50 = 48 mu M).