Chemoenzymatic Synthesis and α-Glucosidase Inhibitory Activity of Dimeric Neolignans Inspired by Magnolol

Journal of Natural Products
Luana PulvirentiCorrado Tringali

Abstract

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 act...Continue Reading

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Citations

Jul 12, 2017·Organic & Biomolecular Chemistry·Andrea BaschieriCorrado Tringali
Jun 27, 2019·BioMed Research International·Jianhong ZhangLonghuo Wu
Sep 25, 2020·International Journal of Molecular Sciences·Giuseppe FlorestaCorrado Tringali
Feb 13, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nunzio CardulloCorrado Tringali
Jul 28, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nunzio CardulloCorrado Tringali
Jan 31, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Safa OufensouGiovanna Delogu
Mar 2, 2021·Journal of Natural Products·Nunzio CardulloCorrado Tringali
Apr 6, 2021·Frontiers in Pharmacology·Yiping LinYing Song
Feb 21, 2019·Journal of Natural Products·Nunzio CardulloCorrado Tringali

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