Structure of indole-3-acetic acid myoinositol esters and pentamethyl-myoinositols

Abstract

GC-MS properties of three isomeric esters of indole-3-acetic acid and myoinositol, three esters of indole-3-acectic acid and myoinositol arabinoside and three esters of indole-3-acetic acid and myoinositol galactoside are presented. MS fragmentation patterns for the four possible pentamethyl myoinositols are also shown. These data indicated that the arabinose, and galactose of the glycosides were in the pyranose form and that C-1 of the sugar was linked to the 5 hydroxyl of myoinositol. Homologies in fragmentation patterns for the esters and the glycoside esters, together with knowledge of the properties of 2- O-indole-3-acetyl-myoinositol, permitted identification of one of the arabinosides as 5- O- l-arabinopyranosyl-2- O-indole-3-acetyl-myoinositol and one of the galactosides as 5- O- d- galactopyranosyl-2- O-indole-3-acetyl-myoinositol. The remaining two GLC peaks observed for the arabinoside were then, most likely, the two mixtures of diastereoisomers 1 d- and 1 l-5- O- l-arabinopryranosyl-1- O-indole-3-acetyl myoinositol and 1 d- and 1 l-5- O- l-arabinopyranosyl-4- O-indole-3-acetyl-myoinositol. The remaining two GLC peaks observed for the galactoside would then be the 1 d and 1 l-5- O- d-galactopyranosyl-1- O-indole-3-acetyl-myoinositol and 1 d- and 1 l-5- O- d- galactopyranosyl-4- O-indoleacetyl-myoinositol.