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

doi:10.1016/j.carres.2013.08.004

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

Pediatrics

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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 language	English (US)
Pages (from-to)	130-136
Number of pages	7
Journal	Carbohydrate Research
Volume	380
DOIs	https://doi.org/10.1016/j.carres.2013.08.004
State	Published - 2013

Funding

This research was conducted as part of Multistate Projects W-168 (NY-C 125-423), W-1168 (NY-C 125-802), and W-2168 (NY-C 125-852) and was supported in part by an undergraduate research grant from the President’s Council of Cornell Women to B.A.L., Dextra and Hatch/Multistate Undergraduate Research Grants to W.G., a grant from Minn-Dak Growers Ltd. to R.L.O., and Cornell University Agricultural Experiment Station federal formula funds received from the National Institutes for Food and Agriculture (NIFA), U.S. Department of Agriculture. Any opinions, findings, conclusions, or recommendations expressed in this publication are those of the authors and do not necessarily reflect the view of the U.S. Department of Agriculture. This work made use of the Polymer Characterization Facility of the Cornell Center for Materials Research (CCMR), with support from the National Science Foundation Materials Research Science and Engineering Centers (MRSEC) program (DMR 1120296). Particular acknowledgement is made for the use of the MALDI-TOF mass spectrometer to obtain HRMS data for compounds 1 – 4 .

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

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

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.",

keywords = "Buckwheat seed, Digalactosyl myo-inositol, Fagopyritol B3, Galactosyl cyclitol, N-(β-glucopyranosyl)-nicotinic acid, Trigalactosyl myo-inositol",

author = "Wei Gui and Lemley, {Bethan A.} and Ivan Keresztes and Condo, {Anthony M.} and Steadman, {Kathryn J.} and Obendorf, {Ralph L.}",

note = "Funding Information: This research was conducted as part of Multistate Projects W-168 (NY-C 125-423), W-1168 (NY-C 125-802), and W-2168 (NY-C 125-852) and was supported in part by an undergraduate research grant from the President{\textquoteright}s Council of Cornell Women to B.A.L., Dextra and Hatch/Multistate Undergraduate Research Grants to W.G., a grant from Minn-Dak Growers Ltd. to R.L.O., and Cornell University Agricultural Experiment Station federal formula funds received from the National Institutes for Food and Agriculture (NIFA), U.S. Department of Agriculture. Any opinions, findings, conclusions, or recommendations expressed in this publication are those of the authors and do not necessarily reflect the view of the U.S. Department of Agriculture. This work made use of the Polymer Characterization Facility of the Cornell Center for Materials Research (CCMR), with support from the National Science Foundation Materials Research Science and Engineering Centers (MRSEC) program (DMR 1120296). Particular acknowledgement is made for the use of the MALDI-TOF mass spectrometer to obtain HRMS data for compounds 1 – 4 . ",

year = "2013",

doi = "10.1016/j.carres.2013.08.004",

language = "English (US)",

volume = "380",

pages = "130--136",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier Ltd",

}

TY - JOUR

T1 - Purification and molecular structure of digalactosyl myo-inositol (DGMI), trigalactosyl myo-inositol (TGMI), and fagopyritol B3 from common buckwheat seeds by NMR

AU - Gui, Wei

AU - Lemley, Bethan A.

AU - Keresztes, Ivan

AU - Condo, Anthony M.

AU - Steadman, Kathryn J.

AU - Obendorf, Ralph L.

N1 - Funding Information: This research was conducted as part of Multistate Projects W-168 (NY-C 125-423), W-1168 (NY-C 125-802), and W-2168 (NY-C 125-852) and was supported in part by an undergraduate research grant from the President’s Council of Cornell Women to B.A.L., Dextra and Hatch/Multistate Undergraduate Research Grants to W.G., a grant from Minn-Dak Growers Ltd. to R.L.O., and Cornell University Agricultural Experiment Station federal formula funds received from the National Institutes for Food and Agriculture (NIFA), U.S. Department of Agriculture. Any opinions, findings, conclusions, or recommendations expressed in this publication are those of the authors and do not necessarily reflect the view of the U.S. Department of Agriculture. This work made use of the Polymer Characterization Facility of the Cornell Center for Materials Research (CCMR), with support from the National Science Foundation Materials Research Science and Engineering Centers (MRSEC) program (DMR 1120296). Particular acknowledgement is made for the use of the MALDI-TOF mass spectrometer to obtain HRMS data for compounds 1 – 4 .

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

KW - Buckwheat seed

KW - Digalactosyl myo-inositol

KW - Fagopyritol B3

KW - Galactosyl cyclitol

KW - N-(β-glucopyranosyl)-nicotinic acid

KW - Trigalactosyl myo-inositol

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UR - http://www.scopus.com/inward/citedby.url?scp=84883650353&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2013.08.004

DO - 10.1016/j.carres.2013.08.004

M3 - Article

C2 - 24036233

AN - SCOPUS:84883650353

SN - 0008-6215

VL - 380

SP - 130

EP - 136

JO - Carbohydrate Research

JF - Carbohydrate Research

ER -

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

Abstract

Funding

Keywords

ASJC Scopus subject areas

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