Concise synthesis of (+)-conduritol F and inositol analogues from naturally available (+)-proto-quercitol and their glucosidase inhibitory activity

Wisuttaya Worawalai; Eakkaphon Rattanangkool; Avassaya Vanitcha; Preecha Phuwapraisirisan; Sumrit Wacharasindhu

doi:10.1016/j.bmcl.2012.01.007

Concise synthesis of (+)-conduritol F and inositol analogues from naturally available (+)-proto-quercitol and their glucosidase inhibitory activity

Bioorg Med Chem Lett. 2012 Feb 15;22(4):1538-40. doi: 10.1016/j.bmcl.2012.01.007. Epub 2012 Jan 10.

Authors

Wisuttaya Worawalai¹, Eakkaphon Rattanangkool, Avassaya Vanitcha, Preecha Phuwapraisirisan, Sumrit Wacharasindhu

Affiliation

¹ Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.

PMID: 22290077
DOI: 10.1016/j.bmcl.2012.01.007

Abstract

An effective synthesis of (+)-conduritol F, (+)-chiro- and (+)-epi-inositols from naturally available (+)-proto-quercitol is described. This synthetic method provides a concise synthesis of cyclitols in enantiomerically pure form. Of the synthesized cyclitols, (+)-conduritol F potently inhibits type I α-glucosidase with an IC(50) value of 86.1 μM, which is five times greater than the standard antidiabetic drug, acarbose.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Enzyme Activation / drug effects
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / pharmacology*
Glucosides / chemical synthesis*
Glucosides / chemistry
Glucosides / pharmacology
Glycoside Hydrolase Inhibitors*
Humans
Inhibitory Concentration 50
Inositol / analogs & derivatives*
Inositol / chemical synthesis*
Inositol / chemistry
Molecular Structure
alpha-Glucosidases

Substances

Enzyme Inhibitors
Glucosides
Glycoside Hydrolase Inhibitors
conduritol F
proto-quercitol
Inositol
glucosidase I
alpha-Glucosidases