Geranylation of Chalcones by a Fungal Aromatic Prenyltransferase,Journal of Agricultural and Food Chemistry

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Geranylation of Chalcones by a Fungal Aromatic Prenyltransferase
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-03-09 , DOI: 10.1021/acs.jafc.2c08743
Qianqian Ran _{1,

2} , Linlan Tao ₃ , Xiang Zhou ₄ , Shu-Ming Li ₅ , Chun-Mao Yuan ₃ , Song Yang ₄ , Kang Zhou _{1,

2}

Affiliation

Geranylated chalcones mainly exist in plants, and many of them have attracted attention because of their diverse pharmacological and biological activities. Herein, we report geranylation of eight chalcones by the Aspergillus terreus aromatic prenyltransferase AtaPT. Ten new mono-geranylated enzyme products (1G–5G, 6G1, 6G2, 7G, 8G1, and 8G2) were obtained. Most of the products are C-geranylated products with prenyl moieties at ring B. In comparison, plant aromatic prenyltransferases usually catalyze the geranylation at ring A. Therefore, AtaPT can be used complementarily for chalcone geranylation to increase the structural diversity of small molecules. In addition, seven compounds (1G, 3G, 4G, 6G1, 7G, 8G1, and 8G2) exhibited a potential inhibitory effect on α-glucosidase with the IC₅₀ values ranging from 45.59 ± 3.48 to 82.85 ± 2.15 μg/mL. Among them, compound 7G (45.59 ± 3.48 μg/mL) was the most potential α-glucosidase inhibitor, which is about seven times stronger than the positive control acarbose (IC₅₀ = 346.63 ± 15.65 μg/mL).

中文翻译：

真菌芳香异戊二烯基转移酶对查尔酮的香叶化

香叶基查耳酮主要存在于植物中，其中许多因其具有多种药理和生物学活性而备受关注。在此，我们报告了Aspergillus terreus芳香族异戊二烯基转移酶 AtaPT对八种查耳酮的香叶基化。获得了十种新的单香叶基化酶产品（1G – 5G 、 6G1、6G2、7G 、 8G1和8G2 ）。大多数产品是C-B环上带有异戊烯基部分的香叶基化产物。相比之下，植物芳香族异戊二烯基转移酶通常催化A环上的香叶基化。因此，AtaPT可以互补地用于查尔酮香叶基化，以增加小分子的结构多样性。此外，7 种化合物（1G、3G、4G、6G1、7G、8G1和8G2）对 α-葡萄糖苷酶具有潜在的抑制作用，IC ₅₀值范围为 45.59 ± 3.48 至 82.85 ± 2.15 μg/ mL 。其中，复合7G_{(45.59 ± 3.48 μg/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 (IC 50} = 346.63 ± 15.65 μg/mL)强约七倍。

更新日期：2023-03-09

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