环糊精葡萄糖基转移酶在天然产物糖基化修饰中的应用

doi:10.13560/j.cnki.biotech.bull.1985.2021-0642

摘要/Abstract

摘要：

环糊精葡萄糖基转移酶（cyclodextrin glucosyltransferase,CGTase）是一种可催化淀粉或多糖中α-1, 4键断裂并环化形成环糊精（cyclodextrins,CDs）的α-淀粉酶。CGTase在工业上主要用于制造环糊精,近年来利用其转糖基作用改造天然产物的性质取得了令人瞩目的研究进展,正成为CGTase应用颇有前途的发展方向。本文结合CGTase的来源、蛋白结构及催化机制等相关研究,重点介绍近年来CGTase在天然产物糖基化修饰中的应用,为CGTase在该领域的深入研究及应用提供参考。

关键词: 环糊精葡萄糖基转移酶, 蛋白结构, 天然产物, 糖基化反应

Abstract:

Cyclodextrin glucosyltransferase（CGTase）is a kind of α-amylase that can catalyze the cleavage and cyclization of α-1, 4 bonds in starch or polysaccharides to form cyclodextrins（CDs）. CGTase is mainly used in industry to produce cyclodextrins. In recent years,There has been remarkable progress in the use of the transglycosylation effect of CGTase to modify the properties of natural products,which is becoming a promising development direction. This review introduces the source,protein structure and catalytic mechanism of CGTase,and focuses on its application in glycosylation modification of natural products in recent years,aiming to provide references for the in-depth research and application of CGTase in this field.

Key words: cyclodextrin glucosyltransferase, protein structure, natural products, glycosylation reaction

张国宁, 冯婧娴, 杨颖博, 陈万生, 肖莹. 环糊精葡萄糖基转移酶在天然产物糖基化修饰中的应用[J]. 生物技术通报, 2022, 38(3): 246-255.

ZHANG Guo-ning, FENG Jing-xian, YANG Ying-bo, CHEN Wan-sheng, XIAO Ying. Application of Cyclodextrin Glucosyltransferase in the Glycosylation Modification of Natural Products[J]. Biotechnology Bulletin, 2022, 38(3): 246-255.

图/表 7

参考文献 69

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底物 Substrate	结构类型 Structure type	CGTase来源 CGTase source	糖基供体 Glycosyl donor	糖苷化产物应用 Application of glycosylation products	参考文献 Reference
木犀草素	黄酮类	Bacillus circulans	α-环糊精	水溶性增加,增强了其在医疗实践中的应用	[32]
柚皮苷	黄酮类	Alkalophilic Bacillus sp	麦芽煳精	溶解度提高1.0×10³倍,扩大其在食品工业中的应用范围	[33]
新橙皮苷	黄酮类	Alkalophilic Bacillus	β-环糊精	溶解度提高1.5×10³倍,扩大其在食品工业中的应用范围	[33]
芦丁	黄酮醇类	Bacillus macerans	糊精	溶解度提高3×10⁴倍	[34]
苯并[H]喹唑啉类化合物	杂环化合物	Thermophilic Bacterial	γ-环糊精	增高水溶性,提高制剂生物活性和生物利用度	[35]
槐糖苷	异黄酮类	Paenibacillus macerans	α-环糊精或麦芽糖	糖链增长水溶性增加,扩大在食品和制药行业中的应用范围	[36]
槲皮素-3-葡萄糖;低聚葡萄糖基柚皮素-7-葡萄糖;低聚葡萄糖基橙皮素-7-葡萄糖	黄酮醇、二氢黄酮	B. macerans	α-环糊精 α-cyclodextrin	糖苷产物水溶性增强,扩大在食品和制药行业中的应用范围	[37]
（-）-表儿茶素（EC）	黄烷-3醇类	Paenibacillus sp.	β-环糊精（最佳）;淀粉;麦芽七糖（G7）	糖苷产物水溶性增强,扩大在食品行业中的应用范围	[38]
没食子儿茶素没食子酸（EGCG）	黄烷-3醇类	Thermoanaerobacter sp	淀粉	植物多酚糖基化,提高溶解度和生物利用度	[39]
橙皮苷	二氢黄酮	A. Bacillus	可溶性淀粉	水溶性提高300倍,扩大应用范围	[40]
葛根素	异黄酮	Bacillus licheniformis	α-cyclodextrin	PU-G、PU-2G以及PU-3G与PU相比,溶解度分别增强16.5、100.9和179.1倍	[41]

底物 Substrate	结构类型 Structure type	CGTase来源 CGTase source	糖基供体 Glycosyl donor	糖苷化产物应用 Application of glycosylation products	参考文献 Reference
木犀草素	黄酮类	Bacillus circulans	α-环糊精	水溶性增加,增强了其在医疗实践中的应用	[32]
柚皮苷	黄酮类	Alkalophilic Bacillus sp	麦芽煳精	溶解度提高1.0×10³倍,扩大其在食品工业中的应用范围	[33]
新橙皮苷	黄酮类	Alkalophilic Bacillus	β-环糊精	溶解度提高1.5×10³倍,扩大其在食品工业中的应用范围	[33]
芦丁	黄酮醇类	Bacillus macerans	糊精	溶解度提高3×10⁴倍	[34]
苯并[H]喹唑啉类化合物	杂环化合物	Thermophilic Bacterial	γ-环糊精	增高水溶性,提高制剂生物活性和生物利用度	[35]
槐糖苷	异黄酮类	Paenibacillus macerans	α-环糊精或麦芽糖	糖链增长水溶性增加,扩大在食品和制药行业中的应用范围	[36]
槲皮素-3-葡萄糖;低聚葡萄糖基柚皮素-7-葡萄糖;低聚葡萄糖基橙皮素-7-葡萄糖	黄酮醇、二氢黄酮	B. macerans	α-环糊精 α-cyclodextrin	糖苷产物水溶性增强,扩大在食品和制药行业中的应用范围	[37]
（-）-表儿茶素（EC）	黄烷-3醇类	Paenibacillus sp.	β-环糊精（最佳）;淀粉;麦芽七糖（G7）	糖苷产物水溶性增强,扩大在食品行业中的应用范围	[38]
没食子儿茶素没食子酸（EGCG）	黄烷-3醇类	Thermoanaerobacter sp	淀粉	植物多酚糖基化,提高溶解度和生物利用度	[39]
橙皮苷	二氢黄酮	A. Bacillus	可溶性淀粉	水溶性提高300倍,扩大应用范围	[40]
葛根素	异黄酮	Bacillus licheniformis	α-cyclodextrin	PU-G、PU-2G以及PU-3G与PU相比,溶解度分别增强16.5、100.9和179.1倍	[41]

底物 Substrate	结构类型 Structure type	CGTase来源 CGTase source	糖基供体 Glycosyl donor	糖苷化产物应用 Application of glycosylation products	参考文献 Reference
熊果苷arbutin	苯酚类	Bacillus macerans	淀粉	对人酪氨酸酶抑制活性增强	[42]
α-生育酚-β-葡萄糖苷、δ-生育酚-β-葡萄糖苷	多酚类	不明确	淀粉	对大鼠腹膜肥大细胞产生IgE抗体和增强组胺释放抑制作用	[43]
对苯二酚（HQ）	苯酚类	Thermoanaerobacter sp	麦芽糊精	抗褐变能力增强	[44-45]
α-L-鼠李糖	糖类	Bacillus circulans 251	麦芽糖糊精	可能应用于针对细菌性痢疾的合成候选疫苗	[46]
槲皮素-3-葡萄糖;低聚葡萄糖基柚皮素-7-葡萄糖;低聚葡萄糖基橙皮素-7-葡萄糖	黄酮醇、二氢黄酮	B. macerans	α-环糊精	对Cu²⁺氧化降解的抵抗能力大大增强	[37]
（+）儿茶素	黄烷-3醇类	B. macerans	淀粉	抑制蘑菇中酪氨酸酶的活性	[47]
辣木提取物中的多酚类化合物	多酚类	Trichoderma viride	小麦淀粉	抗氧化和清除自由基能力增强	[7]
月桂酸蔗糖	糖类	不明确	糊精	潜在的抗肿瘤和杀虫活性	[48]
橙皮素苷（3'-, 5-,and 7-O-glucosides）	二氢黄酮	不明确	淀粉	对IgE抗体和大鼠嗜中性白细胞产生O₂具有抑制作用	[49]
辣椒素的β葡萄糖苷	芳香烃类	不明确	淀粉	抑制IgE抗体的形成	[50]
白藜芦醇	多酚类	Thermoanaerobacter sp	淀粉	具有表面活性剂性质	[51]
水杨醇	酚类	B. macerans	α-环糊精	促进吸收,并可作为温和有效的解热镇痛药前体	[52]
（-）-表儿茶素（EC）	黄烷-3醇类	Paenibacillus sp.	β-环糊精（最佳）;淀粉;麦芽七糖（G7）	糖苷产物抗紫外线褐变能力增强	[38]
橙皮苷	二氢黄酮类	Alkalophilic Bacillus	可溶性淀粉	糖苷产物吸收紫外线以稳定食品中的色素	[40]
Anhydro-D-fructose	糖类	不明确	β-环糊精	降低了与牛血清白蛋白的氨基羰基反应活性	[53]
1, 5-Anhydro-D-fructose	糖类	Bacillus stearothermophilus	β-环糊精	为提高食物蛋白溶解性和稳定性以及蛋白酶抗性提供新的手段	[54]
D-pinitol L-chiro-inositol D-chiro-Inositol muco-inositol allo-inositol	脂环醇	Thermoanaerobacter sp	β-环糊精	肌醇糖基化衍生物在细胞功能中具有多种生理作用	[55]
肌醇（myoinositol）	脂环醇	Bacillus ohbensis.	β-环糊精	肌醇糖基化衍生物在细胞功能中具有多种生理作用	[55]

底物 Substrate	结构类型 Structure type	CGTase来源 CGTase source	糖基供体 Glycosyl donor	糖苷化产物应用 Application of glycosylation products	参考文献 Reference
熊果苷arbutin	苯酚类	Bacillus macerans	淀粉	对人酪氨酸酶抑制活性增强	[42]
α-生育酚-β-葡萄糖苷、δ-生育酚-β-葡萄糖苷	多酚类	不明确	淀粉	对大鼠腹膜肥大细胞产生IgE抗体和增强组胺释放抑制作用	[43]
对苯二酚（HQ）	苯酚类	Thermoanaerobacter sp	麦芽糊精	抗褐变能力增强	[44-45]
α-L-鼠李糖	糖类	Bacillus circulans 251	麦芽糖糊精	可能应用于针对细菌性痢疾的合成候选疫苗	[46]
槲皮素-3-葡萄糖;低聚葡萄糖基柚皮素-7-葡萄糖;低聚葡萄糖基橙皮素-7-葡萄糖	黄酮醇、二氢黄酮	B. macerans	α-环糊精	对Cu²⁺氧化降解的抵抗能力大大增强	[37]
（+）儿茶素	黄烷-3醇类	B. macerans	淀粉	抑制蘑菇中酪氨酸酶的活性	[47]
辣木提取物中的多酚类化合物	多酚类	Trichoderma viride	小麦淀粉	抗氧化和清除自由基能力增强	[7]
月桂酸蔗糖	糖类	不明确	糊精	潜在的抗肿瘤和杀虫活性	[48]
橙皮素苷（3'-, 5-,and 7-O-glucosides）	二氢黄酮	不明确	淀粉	对IgE抗体和大鼠嗜中性白细胞产生O₂具有抑制作用	[49]
辣椒素的β葡萄糖苷	芳香烃类	不明确	淀粉	抑制IgE抗体的形成	[50]
白藜芦醇	多酚类	Thermoanaerobacter sp	淀粉	具有表面活性剂性质	[51]
水杨醇	酚类	B. macerans	α-环糊精	促进吸收,并可作为温和有效的解热镇痛药前体	[52]
（-）-表儿茶素（EC）	黄烷-3醇类	Paenibacillus sp.	β-环糊精（最佳）;淀粉;麦芽七糖（G7）	糖苷产物抗紫外线褐变能力增强	[38]
橙皮苷	二氢黄酮类	Alkalophilic Bacillus	可溶性淀粉	糖苷产物吸收紫外线以稳定食品中的色素	[40]
Anhydro-D-fructose	糖类	不明确	β-环糊精	降低了与牛血清白蛋白的氨基羰基反应活性	[53]
1, 5-Anhydro-D-fructose	糖类	Bacillus stearothermophilus	β-环糊精	为提高食物蛋白溶解性和稳定性以及蛋白酶抗性提供新的手段	[54]
D-pinitol L-chiro-inositol D-chiro-Inositol muco-inositol allo-inositol	脂环醇	Thermoanaerobacter sp	β-环糊精	肌醇糖基化衍生物在细胞功能中具有多种生理作用	[55]
肌醇（myoinositol）	脂环醇	Bacillus ohbensis.	β-环糊精	肌醇糖基化衍生物在细胞功能中具有多种生理作用	[55]

底物 Substrate	结构类型 Structure type	CGTase来源 CGTase source	糖基供体 Glycosyl donor	糖苷化产物应用 Application of glycosylation products	参考文献 Reference
新橙皮苷	黄酮类	Alkalophilic Bacillus	可溶性淀粉	苦味降低10倍	[33]
Neohesperidin	Flavonoid		Soluble starch	10 times lower of bitterness
甜叶悬钩子苷	二萜类	Bacillus circulans	可溶性淀粉	甜度增加	[60]
Rubusoside	Diterpenoid		Soluble starch	Increased sweetness
罗汉果V Mogroside V	四环三萜类 Tetracyclic triterpenoid	Paenibacillus macerans Geobacillus sp. Thermoanaerobacter sp.	麦芽糊精 Maltodextrin	甜度增加 Increased sweetness	[61-62]
甘油 Glycerin	脂肪醇 Fatty alcohol	Geobacillus（Bacillus）stearothermophilus（效果较好 Good effect） Thermoanaerobacter sp.（效果较好 Good effect）Bacillus circulans	淀粉Starch	有望应用于食品以改善口感It is expected to be used to improve the taste of food	[63]