Inoue T, Mimaki Y, Sashida Y, Kobayashi M
School of Pharmacy, Tokyo University of Pharmacy and Life Science, Japan.
Chem Pharm Bull (Tokyo). 1995 Jul;43(7):1162-6. doi: 10.1248/cpb.43.1162.
The full structures of the two steroidal saponins from Narthecium asiaticum MAXIM. We previously identified as toxic substances by monitoring the toxicity in guinea pigs were phytochemically reinvestigation on the aerial parts of the plant. The desired toxic saponins (6,7) were isolated together with two known lignan glucosides (1,2), a known flavonoid glucoside (3), a new furanone glucoside (4), a known steroidal saponin (5) and a new steroidal saponin (8). The structures of the new furanone glucoside, toxic saponins and new saponin were determined on the basis of spectroscopic data and acid- or enzymatic-catalyzed hydrolysis to be (S)-5-beta-D-glucopyranosyloxy-4-methoxyfuran-2(5H)-one (4), (25R,S)-5 beta-spirostan-3 beta-ol 3-O-[O-beta-D-glucopyranosyl-(1-->2)-] O-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-galactopyranoside] (6), (25R,S)-5 beta-spirostan-3 beta-ol 3-}O[O-beta-D-glucopyranosyl-(1-->2- O-[beta-D-xylopyranosyl-(1-->3)]-beta-D-galactopyranoside] (7) and (24S,25R)-5 beta-spirostan-3 beta,24-diol 3-O-[O-beta-D- glucopyranosyl-(1-->2)-O-]alpha-L-arabinopyranosyl-(1-->3)]-beta-D - galactopyranoside] (8), respectively.
对亚洲纳茜菜（Narthecium asiaticum MAXIM.）中的两种甾体皂苷进行了全结构研究。我们之前通过监测豚鼠的毒性将其鉴定为有毒物质，此次对该植物地上部分进行了植物化学再研究。从该植物地上部分分离得到了所需的有毒皂苷（6,7），以及两种已知的木脂素糖苷（1,2）、一种已知的黄酮糖苷（3）、一种新的呋喃酮糖苷（4）、一种已知的甾体皂苷（5）和一种新的甾体皂苷（8）。基于光谱数据以及酸催化或酶催化水解，确定了新呋喃酮糖苷、有毒皂苷和新皂苷的结构分别为（S）-5-β-D-吡喃葡萄糖氧基-4-甲氧基呋喃-2(5H)-酮（4）、（25R,S）-5β-螺旋甾烷-3β-醇3-O-[O-β-D-吡喃葡萄糖基-(1→2)-]O-[α-L-阿拉伯吡喃糖基-(1→3)]-β-D-吡喃半乳糖苷（6）、（25R,S）-5β-螺旋甾烷-3β-醇3-O-[O-β-D-吡喃葡萄糖基-(1→2)-O-[β-D-吡喃木糖基-(1→3)]-β-D-吡喃半乳糖苷（7）和（24S,25R）-5β-螺旋甾烷-3β,24-二醇3-O-[O-β-D-吡喃葡萄糖基-(1→2)-O-]α-L-阿拉伯吡喃糖基-(1→3)]-β-D-吡喃半乳糖苷（8）。
