Study on Improved Utilization of Sweet Natural Glycosides by Enzymic Transglycosylation

酶转糖基提高甜味天然糖苷利用率的研究

• 批准号: 63870091
• 负责人: TANAKA Osamu
• 金额: $ 4.74万
• 依托单位: HIROSHIMA UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Developmental Scientific Research
• 财政年份: 1988
• 资助国家: 日本
• 起止时间: 1988 至 1989
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-63870091/
• 关键词: steviol sweet glycoside; enzymic transglycosylation; sweetener; stevioside; rubusoside; structure-sweetness relationship; cyclodextringlucosyltransferase; galactosidase; 甘味ステビオ-ル配糖体; ステビオシド; ステビオール甘味配糖体; 酵素的糖転移反応; 甘味改良研究; 天然甘味剤; シクロデキストリングルコ

In order to improve intensity and quality of sweetness, enzymic transglucosylation of sweet natural glycosides, stevioside(S) and rubusoside(R) has been investigated.The complete separation and identification of alpha-1,4-glucosylated products from S and R with soluble starch and cycloddxtringlucosyltransferase (CGTase) were achieved.The beta-glucosyl ester group at 19-carboxylic acid of S and R was chemically replaced by a beta-galactosyl group as a blocker against the glucosylation with CGTase. Both the galactosyl esters were regioselectively glucosylated on the 13-glycosyl moiety with CGTase.The evaluation of sweetness of all of the above glucosylated products revealed the following structure-sweetness relationship of glycosides of this series. Remarkable improvement in both the intensity and quality of sweetness was observed for the products which have three or four glucosyl groups at the 13-position. It was noted that the products having more glucosyl groups at the 13-position sho … More wed less sweetness. Transglucosylation at the 19-position also resulted in the decrease of sweetness.The regioselective control of the enzymic transglycosylation of S has been studied under the various conditions. It was found that in the presence of tubeimoside-I which has the potent inclusion property, the glucosylation of S at the 19-position was suppressed, leading to the decrease of the production of the worse sweeteners.Blocking of the 4-hydroxyl group of the 19-COO-beta-glucosyl group of R against glucosylation with CGTase has been investigated extensively by galactosylation with a variety of alpha- and beta-galactosidases. It was disclosed that beta-galactosylation of R with lactose and beta-galactosidase produced by Bacillus circulans effectively afforded the 19--COO-beta-galactosyl-(l--4)-beta-glucoside. Transgiucosylation of this compound with CGTase followed by de-galactosylation with beta-galactosidase yielded the better sweeteners which were mono-, di- or tri-glucosylated exclusively at 13-position.Solubilization of alpha-tochopherol in water was observed for sweet Stevia glycosides, S and rebaudioside-A. Less

为了提高甜菊糖的甜度和品质，研究了甜菊糖甙（S）和甜茶甙（R）的酶促转糖基化反应。用可溶性淀粉和环己基葡萄糖基转移酶（CGTase）对S和R进行4-葡萄糖基化，将S和R的19-位羧酸上的β-葡萄糖酯基化学取代为β-葡萄糖酯基。半乳糖基作为CGT酶葡糖基化的阻断剂。这两种半乳糖基酯均在13-糖基部分上用CGTase区域选择性地进行了糖基化。所有上述糖基化产物的甜度评价揭示了该系列糖苷的以下结构-甜度关系。对于在13位具有三个或四个葡糖基的产物，观察到甜味强度和质量的显著改善。在13-位葡萄糖基较多的产物中， ...更多信息 少一点甜蜜。在19位的转糖基化也导致了甜度的降低。在各种条件下研究了S的酶促转糖基化的区域选择性控制。发现在具有强包合性质的土贝母苷-I存在下，19位S的葡萄糖基化被抑制，导致不良甜味剂的产生减少。已经公开了R与乳糖和环状芽孢杆菌产生的β-半乳糖苷酶的β-半乳糖基化有效地提供了19-β-COO-β-半乳糖基-（1 - 4）-β-葡糖苷。该化合物用CGTase转葡糖基化，然后用β-半乳糖苷酶去半乳糖基化，产生仅在13位单-、二-或三-葡糖基化的较好甜味剂。少

项目成果

福永裕一郎: "Enzymic Transglucosylation products of Stevioside: Separation and Sweetness-Evaluation." Agricultural and Biological Chemistry. 53. 1603-1607 (1989)

Yuichiro Fukunaga：“甜菊苷的酶转葡萄糖基化产物：分离和甜味评估。” 53. 1603-1607 (1989)

北畑寿美雄: "Production of Rubusoside Derivatives by Transgalactosylation of Various β-Galactosidases." Agricultural and Biological Chemistry. 53. 2923-2928 (1989)

Sumio Kitahata：“通过各种 β-半乳糖苷酶的转半乳糖基化生产悬钩子苷衍生物。”农业和生物化学。 53. 2923-2928 (1989)

田中治: "甘味ステビオ-ル配糖体のバイオインダストリ-" バインダストリ-. (1990)

Osamu Tanaka：“甜菊糖苷的生物工业”Bindustry (1990)。

福永裕一郎: Agricultural and Biological Chemistry. 55. (1989)

福永雄一郎：农业和生物化学 55。（1989）

Sumio Kitahata, Hiroshi Ishikawa, Takeshi Miyata, Osamu Tanaka: "Production of Rubusoside Derivatives by Transgalactosylation of Various alpha-Galactosidases" Agric. Biol. Chem. 53(11), 2929-2934 (1989).

Sumio Kitahata、Hiroshi Ishikawa、Takeshi Miyata、Osamu Tanaka：“通过各种 α-半乳糖苷酶的转半乳糖基化生产悬钩子苷衍生物”Agric。