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

Gui, Wei, Lemley, Bethan A., Keresztes, Ivan, Condo, Anthony M., Jr., Steadman, Kathryn J. and Obendorf, Ralph L. (2013) Purification and molecular structure of digalactosyl myo-inositol (DGMI), trigalactosyl myo-inositol (TGMI), and fagopyritol B3 from common buckwheat seeds by NMR. Carbohydrate Research, 380 130-136. doi:10.1016/j.carres.2013.08.004


Author Gui, Wei
Lemley, Bethan A.
Keresztes, Ivan
Condo, Anthony M., Jr.
Steadman, Kathryn J.
Obendorf, Ralph L.
Title Purification and molecular structure of digalactosyl myo-inositol (DGMI), trigalactosyl myo-inositol (TGMI), and fagopyritol B3 from common buckwheat seeds by NMR
Journal name Carbohydrate Research   Check publisher's open access policy
ISSN 0008-6215
1873-426X
Publication date 2013-10-18
Year available 2013
Sub-type Article (original research)
DOI 10.1016/j.carres.2013.08.004
Volume 380
Start page 130
End page 136
Total pages 7
Place of publication Oxford, United Kingdom
Publisher Pergamon
Collection year 2014
Language eng
Formatted 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.
Keyword Buckwheat seed
Digalactosyl myo-inositol
Trigalactosyl myo-inositol
Fagopyritol B3
Galactosyl cyclitol
N-(beta-glucopyranosyl)-nicotinic acid
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Queensland Alliance for Agriculture and Food Innovation
Official 2014 Collection
School of Pharmacy Publications
 
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