Towards the elusive structure of kotalanol, a naturally occurring glucosidase inhibitor.

B Mario Pinto, Sankar Mohan

Journal: Natural product reports 2010;27(4):481-8

PMID: 20336233

Full Text on Royal Society of Chemistry View on PubMed

Abstract

This Highlight describes the detailed approach used to determine the absolute stereochemistry of the stereogenic centers in the acyclic side chain of kotalanol, a naturally occurring glucosidase inhibitor isolated from the plant Salacia reticulata. The plant extract itself is used in Ayurvedic medicine for the treatment of Type 2 diabetes. We highlight the syntheses of proposed candidates based on structure-activity relationships, the total synthesis of kotalanol, and crystallographic studies of kotalanol and its de-O-sulfonated derivative complexed with recombinant human maltase glucoamylase (MGA), a critical intestinal glucosidase involved in the breakdown of glucose oligomers into glucose.

Address: Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada.

DOI: 10.1039/b925950c

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MeSH Terms: Biological Products, Diabetes Mellitus, Type 2, Glucosidases, Glycoside Hydrolase Inhibitors, Humans, Intestines, Medicine, Ayurvedic, Molecular Structure, Monosaccharides, Salacia, Stereoisomerism, Structure-Activity Relationship, Sulfates, alpha-Glucosidases