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Chemoenzymatic Synthesis and α-Glucosidase Inhibitory Activity of Dimeric Neolignans Inspired by Magnolol.
Pulvirenti, Luana; Muccilli, Vera; Cardullo, Nunzio; Spatafora, Carmela; Tringali, Corrado.
Afiliação
  • Pulvirenti L; Dipartimento di Scienze Chimiche, Università degli Studi di Catania , Viale A. Doria 6, I-95125 Catania, Italy.
  • Muccilli V; Dipartimento di Scienze Chimiche, Università degli Studi di Catania , Viale A. Doria 6, I-95125 Catania, Italy.
  • Cardullo N; Dipartimento di Scienze Chimiche, Università degli Studi di Catania , Viale A. Doria 6, I-95125 Catania, Italy.
  • Spatafora C; Dipartimento di Scienze Chimiche, Università degli Studi di Catania , Viale A. Doria 6, I-95125 Catania, Italy.
  • Tringali C; Dipartimento di Scienze Chimiche, Università degli Studi di Catania , Viale A. Doria 6, I-95125 Catania, Italy.
J Nat Prod ; 80(5): 1648-1657, 2017 05 26.
Article em En | MEDLINE | ID: mdl-28497968
A chemoenzymatic synthesis of a small library of dimeric neolignans inspired by magnolol (1) is reported. The 2-iodoxybenzoic acid (IBX)-mediated regioselective ortho-hydroxylation of magnolol is described, affording the bisphenols 6 and 7. Further magnolol analogues (12, 13, 15-17, 19-23) were obtained from eugenol (3), tyrosol (4), and homovanillic alcohol (5), through horseradish peroxidase (HRP)-mediated oxidative coupling and regioselective ortho-hydroxylation or ortho-demethylation in the presence of IBX, followed by reductive treatment with Na2S2O4. A chemoselective protection/deprotection of the alcoholic group of 4 and 5 was carried out by lipase-mediated acetylation/deacetylation. The dimeric neolignans, together with 1 and honokiol (2), were evaluated as inhibitors of yeast α-glucosidase, in view of their possible utilization and optimization as antidiabetic drugs. The synthetic analogues of magnolol showed a strong inhibitory activity with IC50 values in the range 0.15-4.1 µM, much lower than those of honokiol and the reference compounds quercetin and acarbose. In particular, a very potent inhibitory activity, with an IC50 of 0.15 µM, was observed for 1,1'-dityrosol-8,8'-diacetate (15), and comparable inhibitory activities were also shown by bisphenols 6 (0.49 µM), 13 (0.50 µM), and 22 (0.86 µM). A kinetic study showed that 15 acts as a competitive inhibitor, with a Ki value of 0.86 µM.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Álcool Feniletílico / Compostos de Bifenilo / Eugenol / Lignanas / Alfa-Glucosidases / Hipoglicemiantes / Iodobenzoatos Idioma: En Ano de publicação: 2017 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Álcool Feniletílico / Compostos de Bifenilo / Eugenol / Lignanas / Alfa-Glucosidases / Hipoglicemiantes / Iodobenzoatos Idioma: En Ano de publicação: 2017 Tipo de documento: Article