50 北五加皮成分の研究(第4報) : Glycoside H_1の構造
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概要
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Examinations were made on the chemical structure of glycoside H_1, colorless needles from MeOH -AcOEt saturated with water, C_<56>H_<92>O_<24> mp 182° isolated from Chinese crude drug, Bei-Wujiapi (cortex of Periploca sepium Bge. (Asclepiadaceae)) in crystalline state. The structure was established as represented by formula (1). On hydrolysis with 0.05N H_2SO_4-MeOH, (1) afforded three main products, Δ^5 -pregnene-3β,20α-diol(20)-β-D-glucopyranosyl-(1_<glu>→6_<glu>)-β-D-glucopyranosyl(1_<glu>→2_<dig>)-β-D-digitalopyranoside (2), methyl 4-O-(2-O-acetyl-β-D-digitalosyl)-β-D-cymaroside (3) and 4-O-(2-O-acetyl-β-D-digitalosyl) -D-cymarose (4). Oxydative cleavage of (1) by the modified Smith method gave Δ^5-pregnene-3β,20α-diol trioside (6). The total structure of (1) was deduced from the chemical structures of (2), (3), (4) and (6) as formula (1). The configurations of five sugars were assigned by the comparison of chemical shifts and the coupling constants of each anomeric protons of (1), (2), (3), (4) and (6) by NMR and the application of Klyne's rule to compare the molecular optical rotation of each products. It should be noted that (1) is the first example of the pregnane type glycoside whose sugar moiety links to both C-3 and C-20 hydroxyl groups of the aglycone.
- 天然有機化合物討論会の論文
- 1970-10-01
著者
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庄司 順三
昭和大・薬
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佐久間 聖一
School of Pharmaceutical Sciences, Showa University
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川西 幸子
School Of Pharmaceutical Sciences Showa University
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佐久間 聖一
School Of Pharmaceutical Sciences Showa University
-
佐久間 聖一
昭和大・薬
-
川西 幸子
昭和大・薬
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