Biocatalytic Synthesis of Lipophilic Baicalin Derivatives as Antimicrobial Agents

Enzymatic acylation is commonly used to increase the lipophilicity of flavonoids. However, the absence of primary hydroxyl groups makes it challenging to acylate baicalin using traditional acylation methods. In this study, an enzymatic esterification strategy was developed to introduce fatty-acid ch...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of agricultural and food chemistry 2019-10, Vol.67 (42), p.11684-11693
Hauptverfasser: Xin, Xuan, Zhang, Mengmeng, Li, Xiao-Feng, Zhao, Guanglei
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Enzymatic acylation is commonly used to increase the lipophilicity of flavonoids. However, the absence of primary hydroxyl groups makes it challenging to acylate baicalin using traditional acylation methods. In this study, an enzymatic esterification strategy was developed to introduce fatty-acid chains into baicalin at its carboxyl group, hence successfully synthesizing a new series of baicalin ester derivatives in nonaqueous media. Under the optimal reaction conditions, up to 95% conversion of baicalin was achieved. Antimicrobial evaluation of the baicalin ester derivatives indicated a corresponding increase to that of C log P values, with a cutoff effect at C log P = 5.2. Baicalin ester derivatives with C log P values of 4.9–5.2 exhibited the most potent antimicrobial activity. Interestingly, the introduction of medium-length fatty alcohol chains not only increased lipophilicity but also endowed them with membrane-disrupting properties. This study, therefore, provides an understanding of the esterification of flavonoid glycosides and a prospective application of the ester derivatives.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.9b04667