Yoshiki Y, Kim J H, Okubo K, Nagoya I, Sakabe T, Tamura N
Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, Miyagi, Japan.
Phytochemistry. 1995 Jan;38(1):229-31. doi: 10.1016/0031-9422(94)00571-a.
A new 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP)-conjugated saponin, lablab saponin I, was isolated from the hypocotyl of hyacinth bean (Dolichos lablab). The structure was elucidated by 1H NMR and 13C NMR spectroscopy and chemical techniques as 3-O-[alpha-L-rhamnopyranosyl- (1-->2)-beta-D-galactopyranosyl(1-->2)-beta-D-glucuronopyranosyl(1 -->)]-22-O- [2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one(2'-->)]-3 beta, 22 beta, 24-trihy-droxyolean-12-en-28-al. SOD (superoxide dismutase)-like activity depended upon the DDMP group and the aldehyde group (C-28) of the aglycone was observed in the order of lablab saponin I > glutathione > soyasaponin beta g > maltol. The soybean saponin Bb, lacking the DDMP moiety was found not to exhibit the SOD-like activity.
从扁豆(Dolichos lablab)的下胚轴中分离出一种新的2,3 - 二氢 - 2,5 - 二羟基 - 6 - 甲基 - 4H - 吡喃 - 4 - 酮(DDMP)共轭皂苷——扁豆皂苷I。通过¹H NMR和¹³C NMR光谱以及化学技术确定其结构为3 - O - [α - L - 鼠李吡喃糖基 - (1→2) - β - D - 吡喃半乳糖基(1→2) - β - D - 吡喃葡萄糖醛酸基(1→)] - 22 - O - [2,3 - 二氢 - 2,5 - 二羟基 - 6 - 甲基 - 4H - 吡喃 - 4 - 酮(2'→)] - 3β, 22β, 24 - 三羟基齐墩果 - 12 - 烯 - 28 - 醛。超氧化物歧化酶(SOD)样活性取决于DDMP基团,并且观察到苷元的醛基(C - 28)的SOD样活性顺序为:扁豆皂苷I>谷胱甘肽>大豆皂苷βg>麦芽酚。缺乏DDMP部分的大豆皂苷Bb未表现出SOD样活性。