title: Concise synthesis of (+)-conduritol F and inositol analogues from naturally available (+)-proto-quercitol and their glucosidase inhibitory activity.
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.
authors.affiliation: Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, Thailand.
authors.forename: Wisuttaya
authors.initials: W
authors.lastname: Worawalai
authors.forename: Eakkaphon
authors.initials: E
authors.lastname: Rattanangkool
authors.forename: Avassaya
authors.initials: A
authors.lastname: Vanitcha
authors.forename: Preecha
authors.initials: P
authors.lastname: Phuwapraisirisan
authors.forename: Sumrit
authors.initials: S
authors.lastname: Wacharasindhu
mesh_terms: D000818:Animals; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors; D006801:Humans; D020128:Inhibitory Concentration 50; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000520:alpha-Glucosidases
chemical_list: D004791:Enzyme Inhibitors; D005960:Glucosides; D065089:Glycoside Hydrolase Inhibitors; C417483:conduritol F; C483225:proto-quercitol; D007294:Inositol; C042059:glucosidase I; D000520:alpha-Glucosidases