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Chemical Study on Structure and Activity of Cucurbitane type Triterpene Glycosides.

葫芦烷型三萜苷的结构和活性的化学研究。

基本信息

批准号：
62570940
负责人：
TANAKA Osamu
金额：
$ 1.09万
依托单位：
HIROSHIMA 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：
1987
资助国家：
日本
起止时间：
1987 至 1988
项目状态：
已结题

项目摘要

Isolation and structure elucidation of cucurbitane glycosides from Chinese cucubitaceous plants, were conducted.From tubers of Hemsleya carnosiflora. eight new glycoside named carnosifloside I-VI(C-I-CI) were isolated and their structures were established. From tubers of H.panacis-scandens, seven new glycosides named scandenoside R1-7(S-R1-7) were isolated together with C-1-III, V and VI. Structures of S-R1-7 were elucidated.From fruits of Siraitia siamensis, mogrosides-IV and V sweet principles of Siraitia grosvenorii (=Mordica grosvenori) together with two new glycosides, the structures of which were assigned as 11-keto-mogroside-V and 3-0-B-glucosyl-26-0-[B-glucosyl-(1 2)]-[B-glucosyl-(1 6)]-B-glucosyl-mogro, respectively.For these natural glycosides as well as compounds derived from the natural glycosides by chemical or enzymic procedures, the relationship between taste and structure was investigated. (1) Compounds with only one or two glucosyl units such as C-i, S-R1-4, are tasteless. (2) 11 -0H glycosides with more than three glucosyl units such as mogroside-V,C-V, -VI and S-R6, are sweet. (3) 11B-0H glycoside a such as S-R7 are tasteless even if they have more than three glucosyl units. (4) 11-keto glycoside a taste bitter. However, the increase of glucosyl unit results in change of taste from bitter to sweet. For example, 11-keto-mogroside V is a glucopentoside, exhibiting sweetss. The bitterness of an 11-keto glucotrioside, C-III is decreased by enzymic glucosylation at the 26-gentiobiosyl moiety with starch and cyclodextrin-glucosyl transferase.

从中国葫芦科植物中分离鉴定了葫芦烷苷类化合物。分离得到8个新苷类化合物，命名为carnosifloside I-VI（C-I-CI），并确定了它们的结构。从人参（H.panacis-scandens）块茎中分离得到7个新苷类化合物，命名为Scandenoside R1-7（S-R1-7）和C-1-III、V、VI。S-R1-7的结构已被鉴定。从罗汉果果实中分离得到罗汉果甜甙-IV和罗汉果甜甙-V（=Mordica grosvenori）以及两种新的糖苷，其结构被指定为11-酮基-罗汉果苷-V和3-0-β-葡糖基-26-0-[β-葡糖基-（1 2）]-[β-葡糖基-（1 6）]-β-葡糖基-罗汉果苷，研究了这些天然糖苷及其通过化学或酶法衍生的化合物的结构与味道的关系。(1)仅具有一个或两个葡糖基单元的化合物如C1、S-R1-4是无味的。(2)具有多于三个葡糖基单元的11-OH糖苷如罗汉果苷-V、C-V、-VI和S-R6是甜的。(3)11B-OH糖苷a如S-R7是无味的，即使它们具有多于三个葡糖基单元。(4)11-酮苷味苦。然而，葡萄糖基单元的增加导致味道从苦到甜的变化。例如，11-酮-罗汉果苷V是一种葡戊糖苷，表现出甜味。11-酮基葡萄糖三苷C-III的苦味通过用淀粉和环糊精-葡萄糖基转移酶在26-龙胆糖基部分进行酶促糖基化而减少。