Synthesis, structural revision, and tyrosinase inhibitory activity of proposed phloretin-4-O-β-D-glucopyranoside from Homalium stenophyllum

Phloretin-4-O-β-D-glucopyranoside (1), isolated from Homalium stenophyllum, was synthesized for the first time through aldol condensation and Schmidt glycosylation reactions aiming to develop a novel hydrophilic tyrosinase inhibitor. However, the specific rotation of synthetic 1 was found to be nega...

Full description

Saved in:
Bibliographic Details
Published in:Natural product research 2022-04, Vol.36 (7), p.1803-1811
Main Authors: Shimakage, Ryo, Nihei, Ken-ichi
Format: Article
Language:English
Subjects:
aldol reaction
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Glucosides - pharmacology
L-glucoside
Monophenol Monooxygenase
Phloretin
Phloretin glycoside
Salicaceae
Schmidt glycosylation
tyrosinase inhibitor
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Phloretin-4-O-β-D-glucopyranoside (1), isolated from Homalium stenophyllum, was synthesized for the first time through aldol condensation and Schmidt glycosylation reactions aiming to develop a novel hydrophilic tyrosinase inhibitor. However, the specific rotation of synthetic 1 was found to be negative and different from that reported for natural product 1. Thus, L-glucoside 2 was chemically synthesized using the established synthetic route of 1, suggesting that the configuration of the natural product 1 was the same as that of 2, as their specific rotation and spectroscopic data were also the same. In addition, the evaluation of the inhibitory activity of 1 and 2 against tyrosinase indicated that 2 was 1.4 times more potent than 1, but they were both relatively weak. Therefore, the enantiomeric analogues 1 and 2 were proved to be unique tyrosinase inhibitors due to the chiral recognition from the tyrosinase active site.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2020.1817922