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Structure and Physiological Activity of DDMP Saponins in Leguminous Plant

豆科植物DDMP皂苷的结构及生理活性

基本信息

批准号：
05660128
负责人：
OKUBO Kazuyoshi
金额：
$ 1.34万
依托单位：
TOHOKU UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1993
资助国家：
日本
起止时间：
1993 至 1994
项目状态：
已结题

项目摘要

The composition and the structures of group B saponins in native soybean seeds were investigated. Five kinds of saponins named soyasaponins alphag, betag, betaa, gammag and gammaa according to elution order from HPLC were isolated, and the structures were characterized as having a 2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) group attached by acetal linkage to C-22 of the aglycones soyasaponines V,I,II,III and IV,respectively. These DDMP cojugated saponins are considered to be the genuine saponins in native soybean seeds, and soyasaponins I,II,III,IV and V are artifacts produced by heating during the extraction or concentration process. The DDMP saponins are widely distributed in the leguminous plant such as soyasaponin betag isolated from rootstock of the American groundnut. And new DDMP saponins were isolated from Phaseolus coccineus and Dolichos lablab, named as soyasaponin alphaa and lablab saponine I respectively. A high concentration of DDMP saponin was observed around the cell in fibrovascular bundles connecting the stem to the plumule.The chemiluminescence (CL) of catechins were measured in the presence of active oxygen species and acetaldehyde (MeCHO). (-)-Epigallocatechin (EGC) exhibited the strongest CL among flavonoids, anthocyanins and catechins. The CL intensity, P,was dependent on the concentrations of active oxygen species, X,such as H_2O_2, catalytic species, Y,such as EGC and receptive species, Z,such as MeCHO as follows ; p=k[X][Y][Z] (k, photon constant). DDMP saponins showed oxygen-radical-scavenging activity assayd by using the xanthin oxidase-NH2OH methods, ESR and chemiluminescence. One milligram of DDMP saponin/mg exhibited superoxide-scavenging activity of a degree equvalent to 17.1 units of superoxide dismutase/ml measured by the ESR spin trapping method. We have found that group A and DDMP saponins are Y equivalent to EGC and Z equivalent to MeCHO,respectively.

研究了大豆种子中B组皂苷的组成和结构。从大豆皂甙中分离得到5种皂甙，按HPLC洗脱顺序分别命名为大豆皂甙α g、β tag、β a、γ mag和γ a，其结构分别为大豆皂甙V、I、II、III和IV的C-22位通过缩醛键连接有2，3-二氢-2，5-二羟基-6-甲基-4H-吡喃-4-酮（DALO）。认为这些大豆皂苷缀合物是天然大豆种子中的真正皂苷，并且大豆皂苷I、II、III、IV和V是在提取或浓缩过程中通过加热产生的人工产物。大豆皂甙广泛分布于豆科植物中，如从美国花生根茎中分离得到的大豆皂甙β。从红小豆和扁豆中分离得到两个新的大豆皂甙，分别命名为大豆皂甙α a和扁豆皂甙I。儿茶素类化合物在活性氧和乙醛（MeCHO）存在下的化学发光（CL）研究结果表明，儿茶素类化合物的化学发光强度与儿茶素类化合物的化学发光强度有关。表没食子儿茶素（EGC）在黄酮类、花色苷类和儿茶素类化合物中表现出最强的化学发光。化学发光强度P与活性氧物种X（如H_2O_2）、催化物种Y（如EGC）和受体物种Z（如MeCHO）的浓度有关，P=k[X][Y][Z]（k为光子常数）。用黄嘌呤氧化酶-NH_2OH法、ESR和化学发光法测定了黄芪皂苷对氧自由基的清除活性。用ESR自旋捕集法测得，1 mg/mg丹参皂苷的超氧化物清除活性相当于17.1单位/ml超氧化物歧化酶。我们发现，A组皂苷和丹参皂苷分别与EGC和MeCHO的Y等价。