Acylation of flavonol glycosides using protein extracts of Croton species (Euphorbiaceae)

Autor(es)

Oliani, Jocimar ^[1] ; Cesarino, Igor ^[1] ; Faria Salatino, Maria Luiza ^[1] ; Salatino, Antonio ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Biosci, Dept Bot, Rua Matao 277, BR-05508090 Sao Paulo, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Rev. bras. Bot.; v. 44, n. 3 SEP 2021.
• Citações Web of Science: 0

Resumo

Acylation of flavonoid glycosides enhances their chemical stability, lipo-solubility and antioxidant activity, improving their medicinal potential. Enzymatic acylation of flavonoid glycosides is advantageous compared to chemical procedures, as these reactions proceed at mild conditions and the acyl group is inserted at specific positions. In the present work, enriched leaf protein extracts of Croton floribundus Spreng and C. urucurana Baillon (Euphorbiaceae) were used as sources of enzymes in approaches to obtain p-coumaroyl derivatives of 3-O-glycosides of kaempferol and quercetin, as well as 7-O-quercetagetin glucoside. Tiliroside (1), helichrysoside (2) and quercetin-3-O-(6 `'-p-coumaroyl)-galactoside (3) were detected by HPLC-DAD and UPLC/MS as products of acylation reaction, using protein extracts of C. urucurana and either p-coumaroyl-CoA or p-coumaric acid plus CoA and ATP. Protein extracts of C. floribundus Spreng were effective toward the acylation of kaempferol-3-O-glucoside. Although acyltransferases seem to be ubiquitous in Croton, the ability to acylate different flavonol glycosides might largely depend on the species. Acyltransferases in the protein extracts are versatile at acylating flavonoids with distinct aglycones and distinct sugar substituents. The failure to attain acylated products of quercetagetin-7-O-glucoside indicates that Croton acyltransferases are regioselective, with a target on 3-O-sugars of flavonoids. (AU)

• Processo FAPESP: 07/02518-6 - Química, potencial farmacológico e filogenia molecular de Croton (Euphorbiaceae), com ênfase em espécies nativas
• Beneficiário: Antonio Salatino
• Modalidade de apoio: Auxílio à Pesquisa - Regular