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Screening UDP-Glycosyltransferases for Effectively Transforming Stevia Glycosides: Enzymatic Synthesis of Glucosylated Derivatives of Rubusoside
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2022-11-24 , DOI: 10.1021/acs.jafc.2c06185 Huayi Pan 1 , Liang Xiao 1 , Kexin Tang 1 , Haojun Xia 1 , Yan Li 1 , Honghua Jia 1 , Ping Wei 1 , Ming Yan 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2022-11-24 , DOI: 10.1021/acs.jafc.2c06185 Huayi Pan 1 , Liang Xiao 1 , Kexin Tang 1 , Haojun Xia 1 , Yan Li 1 , Honghua Jia 1 , Ping Wei 1 , Ming Yan 1
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Five plant-derived uridine diphosphate glycosyltransferases (UGTs) that catalyzed the glucosylation of stevia glycosides (SGs) were uncovered as the result of sequence mining considering the catalytic residues and conserved motifs of the known UGTs. Thereinto, LbUGT from Lycium barbarum with high activity toward rubusoside has been enzymatically characterized. The recombinant LbUGT was demonstrated to catalyze the β-1,6-glucosylation at C19 of rubusoside, producing a monoglucosyl derivative 13-[(O-β-d-glucopyranosyl) oxy] ent-kaur-16-en-19-oic acid-[(6-O-β-d-glucopyranosyl-β-d-glucopyranosyl) ester], which was then submitted to a β-1,2-glucosylation by LbUGT, resulting in a diglucosyl derivative 13-[(O-β-d-glucopyranosyl) oxy] ent-kaur-16-en-19-oic acid-[(2-O-β-d-glucopyranosyl-6-O-β-d-glucopyranosyl-β-d-glucopyranosyl) ester]. The di-glycosylated product of rubusoside showed an obvious increase in sweetness intensity (134 times sweeter than 5% sucrose) and almost eliminated the unpleasant bitter taste. This work will provide a reference for the taste improvement of SGs.
中文翻译：
筛选 UDP-糖基转移酶以有效转化甜叶菊糖苷：甜叶菊苷糖基化衍生物的酶促合成
考虑到已知 UGT 的催化残基和保守基序，序列挖掘的结果发现了五种植物来源的尿苷二磷酸糖基转移酶 (UGT)，它们催化甜菊糖苷 (SG) 的糖基化。其中，来自枸杞的Lb UGT对甜叶悬钩子苷具有高活性，已被酶促表征。重组Lb UGT 被证明可催化甜叶悬钩子苷 C19 的 β-1,6- 糖基化，产生单葡糖基衍生物 13-[( O -β- d -glucopyranosyl ) oxy] ent-kaur-16-en-19-oic酸-[(6- O -β- d -吡喃葡萄糖基-β- d-glucopyranosyl) ester]，然后通过Lb UGT 进行 β-1,2-glucosylation，产生二葡萄糖基衍生物 13-[( O -β- d -glucopyranosyl ) oxy] ent-kaur-16-en- 19-油酸-[(2 - O-β-d-吡喃葡萄糖基-6 - O -β- d-吡喃葡萄糖基-β- d-吡喃葡萄糖基)酯]。甜叶悬钩子苷的二糖基化产物甜味强度明显增加（比 5% 蔗糖甜 134 倍），几乎消除了令人不快的苦味。这项工作将为SGs的口味改进提供参考。
更新日期：2022-11-24
中文翻译：
筛选 UDP-糖基转移酶以有效转化甜叶菊糖苷：甜叶菊苷糖基化衍生物的酶促合成
考虑到已知 UGT 的催化残基和保守基序，序列挖掘的结果发现了五种植物来源的尿苷二磷酸糖基转移酶 (UGT)，它们催化甜菊糖苷 (SG) 的糖基化。其中，来自枸杞的Lb UGT对甜叶悬钩子苷具有高活性，已被酶促表征。重组Lb UGT 被证明可催化甜叶悬钩子苷 C19 的 β-1,6- 糖基化，产生单葡糖基衍生物 13-[( O -β- d -glucopyranosyl ) oxy] ent-kaur-16-en-19-oic酸-[(6- O -β- d -吡喃葡萄糖基-β- d-glucopyranosyl) ester]，然后通过Lb UGT 进行 β-1,2-glucosylation，产生二葡萄糖基衍生物 13-[( O -β- d -glucopyranosyl ) oxy] ent-kaur-16-en- 19-油酸-[(2 - O-β-d-吡喃葡萄糖基-6 - O -β- d-吡喃葡萄糖基-β- d-吡喃葡萄糖基)酯]。甜叶悬钩子苷的二糖基化产物甜味强度明显增加（比 5% 蔗糖甜 134 倍），几乎消除了令人不快的苦味。这项工作将为SGs的口味改进提供参考。
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