Saponin and Sapogenol. XLII. : Structures of Acetyl-soyasaponins A_1,A_2,and A_3,Astringent Partially Acetylated Bisdesmosides of Soyasapogenol A, from American Soybean, the Seeds of Glycine max MERRILL.

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By means of high performance liquid chromatography and other methods, three new partially acetylated soyasaponins, named acetyl-soyasaponin A_1 (6a), acetyl-soyasaponin A_2 (7a), and acetyl-soyasaponin A_3 (8a), were isolated from American soybeans, the seeds of Glycine max MERRILL., together with hitherto known soyasaponins I (3), II (4), and III (5). Acetyl-soyasaponins A_1,A_2,and A_3 are noteworthy due to their bitter and astringent tastes, although their parent saponins, soyasaponins A_1 (6), A_2 (7), and A_3 (8), do not show such tastes.By virtue of the photochemical degradation method for the glucuronide linkage and on the basis of ^1H- and ^<13>C-nuclear magnetic resonance and secondary ion mass spectrum analyses, structures of acetyl-soyasaponins A_1,A_2,and A_3 have been elucidated as 3-O-[β-D-glucopyranosyl-(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]-22-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (6a), 3-O-[β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl]-22-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soyasapogenol A (7a), and 3-O-[α-L-arabinopyranosyl(1→2)-β-D-glucuronopy-ranosyl]-22-O-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl(1→3)-α-L-arabinopyranosyl]soya-sapogenol A (8a), respectively.
公益社団法人日本薬学会の論文
1988-08-25