根皮素广泛存在于水果中,具有多种生物活性。这里,我们证明了二甲基烯丙基化,胚芽化,和法尼基化,特别是真菌异戊二烯基转移酶AnaPT及其突变体在根皮素(1)的非芳香族碳上的第一个二甲基烯丙基化。F265被鉴定为与根皮素的非芳香族碳上的二甲基烯丙基化相关的关键氨基酸残基。突变体AnaPT_F265D,AnaPT_F265G,AnaPT_F265P,AnaPT_F265C,和AnaPT_F265Y被发现通常将异戊二烯化活性增加到1。AnaPT_F265G在C-2'羟基上选择性催化O-香叶化,它涉及与1的羰基的分子内氢键。七种产品,1D5、1D7-1D9、1G2、1G4和1F2在本研究之前没有报道。12种化合物,1D3-1D9,1G1-1G3和1F1-1F2对α-葡萄糖苷酶表现出潜在的抑制作用,IC50值为11.45±0.87至193.80±6.52μg/mL。其中,1G1的IC50值为11.45±0.87μg/mL是最有潜力的α-葡萄糖苷酶抑制剂,比阳性对照阿卡波糖强约30倍,IC50值为346.63±15.65μg/mL。
Phloretin is widely found in fruit and shows various biological activities. Here, we demonstrate the dimethylallylation, geranylation, and farnesylation, particularly the first dimethylallylation at the nonaromatic carbon of phloretin (1) by the fungal prenyltransferase AnaPT and its mutants. F265 was identified as a key amino acid residue related to dimethylallylation at the nonaromatic carbon of phloretin. Mutants AnaPT_F265D, AnaPT_F265G, AnaPT_F265P, AnaPT_F265C, and AnaPT_F265Y were discovered to generally increase prenylation activity toward 1. AnaPT_F265G catalyzes the O-geranylation selectively at the C-2\' hydroxyl group, which involves an intramolecular hydrogen bond with the carbonyl group of 1. Seven products, 1D5, 1D7-1D9, 1G2, 1G4, and 1F2, have not been reported prior to this study. Twelve compounds, 1D3-1D9, 1G1-1G3, and 1F1-1F2, exhibited potential inhibitory effects on α-glucosidase with IC50 values ranging from 11.45 ± 0.87 to 193.80 ± 6.52 μg/mL. Among them, 1G1 with an IC50 value of 11.45 ± 0.87 μg/mL was the most potential α-glucosidase inhibitor, which is about 30 times stronger than the positive control acarbose with an IC50 value of 346.63 ± 15.65 μg/mL.