Purification and molecular structure of digalactosyl myo-inositol (DGMI), trigalactosyl myo-inositol (TGMI), and fagopyritol B3 from common buckwheat seeds by NMR

Wei Gui, Bethan A. Lemley, Ivan Keresztes, Anthony M. Condo, Kathryn J. Steadman, Ralph L. Obendorf*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Three galactosyl cyclitols, digalactosyl myo-inositol (assigned the trivial name DGMI), trigalactosyl myo-inositol (assigned the trivial name TGMI), and trigalactosyl d-chiro-inositol (fagopyritol B3), were isolated from common buckwheat (Fagopyrum esculentum Moench) seeds. Structures of the three compounds were determined by 2D NMR spectroscopy. DGMI is α-d-galactopyranosyl- (1→6)-α-d-galactopyranosyl-(1→1)-1l-myo-inositol, TGMI is α-d-galactopyranosyl-(1→6)-α-d-galactopyranosyl-(1→6) -α-d-galactopyranosyl-(1→1)-1l-myo-inositol, and fagopyritol B3 is α-d-galactopyranosyl-(1→6)-α-d-galactopyranosyl-(1→6) -α-d-galactopyranosyl-(1→2)-1d-chiro-inositol. DGMI and TGMI are higher oligomers of galactinol, a major galactosyl donor in plant seeds. Fagopyritol B3 is a higher oligomer of the fagopyritol B series and one of six fagopyritols found in buckwheat seeds and in the bran milling fraction. Samples of TGMI and fagopyritol B3 also contained the compounds N-(β- glucopyranosyl)-nicotinic acid and β-d-apiofuranosyl-(1→6)-β-d- (1-O-methyl)-glucopyranoside.

Original languageEnglish (US)
Pages (from-to)130-136
Number of pages7
JournalCarbohydrate Research
Volume380
DOIs
StatePublished - 2013

Keywords

  • Buckwheat seed
  • Digalactosyl myo-inositol
  • Fagopyritol B3
  • Galactosyl cyclitol
  • N-(β-glucopyranosyl)-nicotinic acid
  • Trigalactosyl myo-inositol

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Purification and molecular structure of digalactosyl myo-inositol (DGMI), trigalactosyl myo-inositol (TGMI), and fagopyritol B3 from common buckwheat seeds by NMR'. Together they form a unique fingerprint.

Cite this