Purification and molecular structure of two digalactosyl D-chiro-inositols and two trigalactosyl D-chiro-inositols from buckwheat seeds.

Carbohydr Res

Department of Crop and Soil Sciences, Seed Biology, Cornell University Agricultural Experiment Station, Cornell University, Ithaca, NY 14853-1901, USA.

Published: March 2001

Two digalactosyl D-chiro-inositols and two trigalactosyl D-chiro-inositols, members of the fagopyritol A series and fagopyritol B series, were isolated from buckwheat (Fagopyrum esculentum Moench) seeds. Structures of the first three were determined by 1H and 13C NMR. Fagopyritol B2 is alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->2) -1D-chiro-inositol, and fagopyritol A2 is alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->3)- 1D-chiro-inositol. Fagopyritol A3, a trigalactosyl D-chiro-inositol, is alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1 -->6) -alpha-D-galactopyranosyl-(1-->3)- 1 D-chiro-inositol. From analysis of hydrolysis products, the second trigalactosyl D-chiro-inositol, fagopyritol B3, isalpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->6) -alpha-D-galactopyranosyl-(1-->2)-1D-chiro-inositol.

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http://dx.doi.org/10.1016/s0008-6215(00)00320-7DOI Listing

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Purification and molecular structure of two digalactosyl D-chiro-inositols and two trigalactosyl D-chiro-inositols from buckwheat seeds.

Carbohydr Res

March 2001

Department of Crop and Soil Sciences, Seed Biology, Cornell University Agricultural Experiment Station, Cornell University, Ithaca, NY 14853-1901, USA.

Two digalactosyl D-chiro-inositols and two trigalactosyl D-chiro-inositols, members of the fagopyritol A series and fagopyritol B series, were isolated from buckwheat (Fagopyrum esculentum Moench) seeds. Structures of the first three were determined by 1H and 13C NMR. Fagopyritol B2 is alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->2) -1D-chiro-inositol, and fagopyritol A2 is alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->3)- 1D-chiro-inositol.

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Article Synopsis
  • Buckwheat embryos contain a significant soluble carbohydrate, fagopyritol B1, making up 40% of their total composition and associated with five other related alpha-galactosyl D-chiro-inositols.
  • The presence of all fagopyritols is confirmed to be easily hydrolyzable by alpha-galactosidase, indicating their structural linkage.
  • Higher levels of fagopyritol B1 during seed development enhance desiccation tolerance and storability, with its accumulation linked to better seed vigor under cooler growth conditions.
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