Esculin is a polyphenol with multiple bioactivities and poor lipophilicity. Therefore, a whole-cell catalytic strategy for esculin acylation was developed to improve its lipophilicity. A total of 12 strains were tested, among which Pseudomonas stutzeri exhibited the highest catalytic activity and mono-acylated regioselectivity. The conversion reached the highest level of 92.7% at 24 h under the optimal conditions, when vinyl acetate was used as an acyl donor. The catalytic ability of P. stutzeri remained above 60% after three cycles. Subsequently, five esculin esters with different lengths of fatty chains were synthesized and structurally identified. Of them, esculin-6′-O-octanoate, esculin-6′-O-laurate, and esculin-6′-O-myristate exhibited cytotoxicity on LO2 cells by inducing apoptosis and necrosis. The cytotoxicity of these three esters may attribute to their membrane-disrupting properties. This study provides a novel whole-cell biocatalytic strategy for the acylation of esculin and insight for application of esculin esters as a food additive or drug.

七叶素是一种多酚，具有多种生物活性，亲脂性较差。因此，开发了七叶苷酰化的全细胞催化策略以提高其亲脂性。共测试了 12 株菌株，其中施氏假单胞菌表现出最高的催化活性和单酰化区域选择性。在最佳条件下，当使用乙酸乙烯酯作为酰基供体时，转化率在 24 小时时达到最高水平 92.7%。P. stutzeri的催化能力三个周期后仍保持在 60% 以上。随后，合成了五种具有不同长度脂肪链的七叶苷酯并对其进行了结构鉴定。其中，esculin-6'-O-octanoate、esculin-6'-O-laurate和esculin-6'-O-myristate通过诱导细胞凋亡和坏死对LO2细胞表现出细胞毒性。这三种酯的细胞毒性可能归因于它们的膜破坏特性。该研究为七叶苷酰化提供了一种新的全细胞生物催化策略，并为七叶苷酯作为食品添加剂或药物的应用提供了见解。