A convenient and scalable synthetic approach has been developed for the synthesis of acyl-C-β-d-glucosides and benzyl-C-β-d-glucosides. The use of Weinreb-amide (WA) functionality was crucial for this accomplishment as the other apparently capable alternatives, had severe limitations for the access to acyl-C-glucosides. The synthesized compounds, acyl and benzyl-C-glucosides promote glucose-uptake activity in the C2C12 (mouse skeletal muscle) cell lines through PPAR-γ mediated GLUT4 expression. The developed synthetic scheme for acyl-and benzyl-C-β-d-glucosides and biostudies evaluating their activity as glucose-uptake promoters are disclosed herein. © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Indrapal Singh Aidhen

Department Of Chemistry

Mukesh Doble

Department Of Biotechnology

Mannem Rajeswara Reddy

Shanmugam Hemaiswarya

Harikrishna Kommidi

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

European Journal of Organic Chemistry

Convenient synthesis of 2-β-d-Glucopyranosylpyridines has been achieved by using Bohlmann–Rahtz heteroannulation reaction between a sugar alkynone and ethyl β-aminocrotonate. The synthesized compounds are analogues of Dapagaliflozin, an approved drug for lowering of blood glucose levels through inhibition of sodium-glucose transporters in the kidney. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Convenient Access to 2-β-d-Glucopyranosylpyridines by Using Bohlmann–Rahtz Heteroannulation

The methanol extract of pomegranate peels was re-extracted with ethyl acetate. It was then evaporated to dryness. It was found to have a profound effect on the glucose uptake in L6 myotubes. The major constituents of this extract were ellagic acid and its glycosides and so further studies were carried out with pure commercial ellagic acid. Its effect on glucose uptake and expression of genes involved in the insulin signalling were investigated individually and in combination with a commercial drug, pioglitazone. They interact synergistically to increase insulin stimulated glucose uptake. Ellagic acid increases the expression of glucose transporter type 4 (GLUT4) and peroxisome proliferator-activated receptor gamma (PPAR-γ). Activation of the latter by pioglitazone upregulates adiponectin, but when combined with pure ellagic acid, this upregulation is achieved at lower concentrations of the drug. The current study proves that insulin sensitising activity of pioglitazone can be enhanced at low doses by combining it with ellagic acid. © 2015 Elsevier Ltd.

Journal of Functional Foods

Ellagic acid potentiates insulin sensitising activity of pioglitazone in L6 myotubes

ACS Central Science

Acyl Glycosides through Stereospecific Glycosyl Cross-Coupling: Rapid Access to C(sp3)-Linked Glycomimetics

PLOS ONE

Anti-Diabetic Effects of Jiang Tang Xiao Ke Granule via PI3K/Akt Signalling Pathway in Type 2 Diabetes KKAy Mice

European Journal of Medicinal Chemistry

Thiazolidinediones and PPAR orchestra as antidiabetic agents: From past to present

Acyl and Benzyl-C-β-D-Glucosides: Synthesis and Biostudies for Glucose-Uptake-Promoting Activity in C2C12 Mytotubes

Journal	Data powered by TypesetEuropean Journal of Organic Chemistry
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	1434193X
Open Access	No