Structure of indole-3-acetic acid myoinositol esters and pentamethyl-myoinositols |
| |
Authors: | Minoru Ueda Robert S Bandurski |
| |
Institution: | Department of Botany and Plant Pathology, Michigan State University, East Lansing, MI 48823, U.S.A. |
| |
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. |
| |
Keywords: | corn indole-3-acetic acid esters myoinositol myoinositol glycosides MS: trimethylsilyl ethers: pentamethyl-myoinositols myoinositol arabinoside myoinositol galactoside IAA (or ROH for figs and tables)—indole-3-acetic acid TMS (or T for figs and tables)—trimethylsilyl TMSOH (or TOH for figs and tables)—trimethylsilanol M—the molecular ion G—the sugar moiety of the glycosides or GOH if the departing group retains a bridge oxygen plus hydrogen I—the inositol moiety |
本文献已被 ScienceDirect 等数据库收录! |