Asano N, Oseki K, Tomioka E, Kizu H, Matsui K
Faculty of Pharmaceutical Sciences, Hokuriku University, Ishikawa, Japan.
Carbohydr Res. 1994 Jun 17;259(2):243-55. doi: 10.1016/0008-6215(94)84060-1.
The reexamination of N-containing sugars from the roots of Morus alba by improved purification procedures led to the isolation of eighteen N-containing sugars, including seven that were isolated from the leaves of Morus bombycis. These N-containing sugars are 1-deoxynojirimycin (1), N-methyl-1-deoxynojirimycin (2), fagomine (3), 3-epi-fagomine (4), 1,4-dideoxy-1,4-imino-D-arabinitol (5), 1,4-dideoxy-1,4-imino-D-ribitol (6), calystegin B2 (1 alpha,2 beta,3 alpha,4 beta-tetrahydroxy-nor-tropane, 7), calystegin C1 (1 alpha,2 beta,3 alpha,4 beta,6 alpha-pentahydroxy-nor-tropane, 8), 1,4-dideoxy-1,4-imino-(2-O-beta-D-glucopyranosyl)-D-arabinitol (9), and nine glycosides of 1. These glycosides consist of 2-O- and 6-O-alpha-D-galactopyranosyl-1-deoxynojirimycins (10 and 11, respectively), 2-O-, 3-O- and 4-O-alpha-D-glucopyranosyl-1-deoxynojirimycins (12, 13, and 14, respectively), and 2-O-, 3-O-, 4-O- and 6-O-beta-D-glucopyranosyl-1-deoxynojirimycins (15, 16, 17, and 18, respectively). Compound 4 is a new member of polyhydroxylated piperidine alkaloids, and the isolation of 6 is the first report of its natural occurrence. It has recently been found that the polyhydroxy-nor-tropane alkaloids possess potent glycosidase inhibitory activities. Calystegin A3 is the trihydroxy-nor-tropane, and calystegins B1 and B2 are the tetrahydroxy-nor-tropane. Calystegin C1, a new member of calystegins, is the first naturally occurring pentahydroxy-nor-tropane alkaloid. The inhibitory activities of these compounds were investigated against rat digestive glycosidases and various commercially available glycosidases.
通过改进的纯化程序对桑树根中的含氮糖类进行重新检测，分离出了18种含氮糖类，其中7种是从家桑的叶子中分离得到的。这些含氮糖类包括1-脱氧野尻霉素（1）、N-甲基-1-脱氧野尻霉素（2）、法戈明（3）、3-表-法戈明（4）、1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇（5）、1,4-二脱氧-1,4-亚氨基-D-核糖醇（6）、加州地锦苷B2（1α,2β,3α,4β-四羟基降托烷，7）、加州地锦苷C1（1α,2β,3α,4β,6α-五羟基降托烷，8）、1,4-二脱氧-1,4-亚氨基-（2-O-β-D-吡喃葡萄糖基）-D-阿拉伯糖醇（9）以及1的9种糖苷。这些糖苷包括2-O-和6-O-α-D-吡喃半乳糖基-1-脱氧野尻霉素（分别为10和11）、2-O-、3-O-和4-O-α-D-吡喃葡萄糖基-1-脱氧野尻霉素（分别为12、13和14）以及2-O-、3-O-、4-O-和6-O-β-D-吡喃葡萄糖基-1-脱氧野尻霉素（分别为15、16、17和18）。化合物4是多羟基哌啶生物碱的新成员，6的分离是其天然存在的首次报道。最近发现多羟基降托烷生物碱具有强大的糖苷酶抑制活性。加州地锦苷A3是三羟基降托烷，加州地锦苷B1和B2是四羟基降托烷。加州地锦苷C1是加州地锦苷类的新成员，并是首个天然存在的五羟基降托烷生物碱。研究了这些化合物对大鼠消化糖苷酶和各种市售糖苷酶的抑制活性。
