Molecular structure of fagopyritol Al (O-α-D-galactopyranosyl-(1→3)-D-chiro-inositol) by NMR

被引:33
作者
Obendorf, RL [1 ]
Steadman, KJ
Fuller, DJ
Horbowicz, M
Lewis, BA
机构
[1] Cornell Univ, Dept Crop & Soil Sci, Ithaca, NY 14853 USA
[2] Cornell Univ, Dept Chem & Chem Bio, NMR Facil, Ithaca, NY 14853 USA
[3] Cornell Univ, Agr Expt Stn, Div Nutr Sci, Ithaca, NY 14853 USA
[4] Res Inst Vegetables Crops, PL-96100 Skierniewice, Poland
关键词
Fagopyrum esculentum; buckwheat; seed; fagopyritol A1; fagopyritol B1; D-chiro-inositol; galactosyl cyclitol;
D O I
10.1016/S0008-6215(00)00133-6
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The molecular structure of fagopyritol A1, a novel galactopyranosyl cyclitol from buckwheat seeds, was determined to be O-alpha-D-galactopyranosyl-(1-->2)-D-chiro-inositol by H-1 and C-13 NMR. Fagopyritol Al is a positional isomer of fagopyritol B1 (O-alpha-D-galactopyranosyl-(1-->2)-D-chiro-inositol), representing a different series of fagopyritol oligomers. Trimethylsilyl derivatives of both compounds have similar mass spectra, but each may be identified by different abundance ratios of fragments with m/z 305/318 and 318/319. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:623 / 627
页数:5
相关论文
共 12 条
[1]   GLYCOSYL-INOSITOL DERIVATIVES .2. SYNTHESIS OF 2-AMINO-2-DEOXY-D-GALACTOSYL-ALPHA-1,3-D-CHIRO-INOSITOL [J].
BERLIN, WK ;
WANG, SN ;
SHEN, TY .
TETRAHEDRON LETTERS, 1990, 31 (08) :1109-1112
[2]   C-13 NUCLEAR MAGNETIC-RESONANCE DATA FOR OLIGOSACCHARIDES [J].
BOCK, K ;
PEDERSEN, C ;
PEDERSEN, H .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1984, 42 :193-225
[3]   Fagopyritol B1, O-α-D-galactopyranosyl-(1→-2)-D-chiro-inositol, a galactosyl cyclitol in maturing buckwheat seeds associated with desiccation tolerance [J].
Horbowicz, M ;
Brenac, P ;
Obendorf, RL .
PLANTA, 1998, 205 (01) :1-11
[4]   Seed desiccation tolerance and storability: Dependence on flatulence-producing oligosaccharides and cyclitols-review and survey [J].
Horbowicz, Marcin ;
Obendorf, Ralph L. .
SEED SCIENCE RESEARCH, 1994, 4 (04) :385-405
[5]   RAT-LIVER INSULIN MEDIATOR WHICH STIMULATES PYRUVATE-DEHYDROGENASE PHOSPHATASE CONTAINS GALACTOSAMINE AND D-CHIROINOSITOL [J].
LARNER, J ;
HUANG, LC ;
SCHWARTZ, CFW ;
OSWALD, AS ;
SHEN, TY ;
KINTER, M ;
TANG, G ;
ZELLER, K .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1988, 151 (03) :1416-1426
[6]   DIRECT GAS-CHROMATOGRAPHIC RESOLUTION OF DL-MYO-INOSITOL 1-PHOSPHATE AND OTHER SUGAR ENANTIOMERS AS SIMPLE DERIVATIVES ON A CHIRAL CAPILLARY COLUMN [J].
LEAVITT, AL ;
SHERMAN, WR .
CARBOHYDRATE RESEARCH, 1982, 103 (02) :203-212
[7]   A new glycoside, 1D-2-O-alpha-D-galactopyranosyl-chiro-inositol from jojoba beans [J].
Ogawa, K ;
Watanabe, T ;
Ikeda, Y ;
Kondo, S .
CARBOHYDRATE RESEARCH, 1997, 302 (3-4) :219-221
[8]   D-CHIRO-INOSITOL METABOLISM IN DIABETES-MELLITUS [J].
OSTLUND, RE ;
MCGILL, JB ;
HERSKOWITZ, I ;
KIPNIS, DM ;
SANTIAGO, JV ;
SHERMAN, WR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (21) :9988-9992
[9]   Structure of galactosylononitol [J].
Richter, A ;
Peterbauer, T ;
Brereton, I .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (08) :749-751
[10]   PURIFICATION AND STRUCTURE DETERMINATION OF 3 ALPHA-D- GALACTOPYRANOSYLCYCLITOLS FROM SOYA BEAN [J].
SCHWEIZER, TF ;
HORMAN, I .
CARBOHYDRATE RESEARCH, 1981, 95 (01) :61-71