Show legend Show as text

Structure type: monomer
Trivial name: alangioside J
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 12701
  Skouroumounis GK, Gunata YZ, Baumes RL "Determination of the absolute stereochemistry of chiral secondary megastigmane alcohols from Shiraz leaves by NMR studies" - The Journal of Essential Oil Research 12(6) (2000) 661-666
  

  The configuration of the chiral secondary alcohols of a megastigmane-3,9-diol was determined using ROESY experiments performed on its peracetylated β-glucopyranosides, previously isolated from Vitis Vinifera Shiraz leaves. On the basis of the data available for structurally related disaccharides, the rules reported previously to determine the conformation of disaccharide linkage were applied to predict the applicability of this method to other chiral secondary alcohols with no or only one bulky substituent on the β-carbons. That would lend additional support to the applicability of the method based on the β-effects of glycosylation in 13C-NMR.

  glycosides, stereochemistry, Vitis vinifera, Shiraz vine leaves, secondary alcohols, glucopyranosides, megastigmanediol

  Publication DOI: 10.1080/10412905.2000.9712184
  Journal NLM ID: 9884355
  Publisher: Philadelphia, PA: Taylor & Francis
  Institutions: INRA IPV(Institut National de la Recherche Agronomique, Institut des Produits de la Vigne Jnité de Recherche Biopolymères Arômes), Montpellier, France
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
  
   
  
  Vitis vinifera cv. Shiraz
  CSDB ID 67941 (all data & tools)
• Article ID: 12702
  Skouroumounis GK, Gunata YZ, Baumes RL "Isolation of two megastigmane-3,9-diol glucosides from Shiraz leaves" - The Journal of Essential Oil Research 12(6) (2000) 653-660
  

  The water soluble methanol extract from Shiraz leaves, was passed through a XAD 2 column, and elution with methanol yielded a crude glycoconjugate composite. Further separation of this polar fraction using IIPLC semi preparative Cm18 column followed by acetylation and flash chromatography yielded Alangioside J and a new norisoprenoid β-glucopyranoside. Using 1II- and 13C-NMR techniques, the latter was shown to be the C-9 conjugate of the same (3S, 5R, 6S,9R)-megastigmane-3,9-diol as the C-3 conjugated former one.

  glycosides, Vitis vinifera, Shiraz vine leaves, glucopyranoside, trifluoroacetylation, megastigmane-3, 9-diol

  Publication DOI: 10.1080/10412905.2000.9712183
  Journal NLM ID: 9884355
  Publisher: Philadelphia, PA: Taylor & Francis
  Institutions: INRA IPV(Institut National de la Recherche Agronomique, Institut des Produits de la Vigne Jnité de Recherche Biopolymères Arômes), Montpellier, France
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
  
   
  
  Vitis vinifera cv. Shiraz
  CSDB ID 67943 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 12701
  Skouroumounis GK, Gunata YZ, Baumes RL "Determination of the absolute stereochemistry of chiral secondary megastigmane alcohols from Shiraz leaves by NMR studies" - The Journal of Essential Oil Research 12(6) (2000) 661-666
  

  The configuration of the chiral secondary alcohols of a megastigmane-3,9-diol was determined using ROESY experiments performed on its peracetylated β-glucopyranosides, previously isolated from Vitis Vinifera Shiraz leaves. On the basis of the data available for structurally related disaccharides, the rules reported previously to determine the conformation of disaccharide linkage were applied to predict the applicability of this method to other chiral secondary alcohols with no or only one bulky substituent on the β-carbons. That would lend additional support to the applicability of the method based on the β-effects of glycosylation in 13C-NMR.

  glycosides, stereochemistry, Vitis vinifera, Shiraz vine leaves, secondary alcohols, glucopyranosides, megastigmanediol

  Publication DOI: 10.1080/10412905.2000.9712184
  Journal NLM ID: 9884355
  Publisher: Philadelphia, PA: Taylor & Francis
  Institutions: INRA IPV(Institut National de la Recherche Agronomique, Institut des Produits de la Vigne Jnité de Recherche Biopolymères Arômes), Montpellier, France
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
  
   
  
  Vitis vinifera cv. Shiraz
  CSDB ID 67942 (all data & tools)
• Article ID: 12702
  Skouroumounis GK, Gunata YZ, Baumes RL "Isolation of two megastigmane-3,9-diol glucosides from Shiraz leaves" - The Journal of Essential Oil Research 12(6) (2000) 653-660
  

  The water soluble methanol extract from Shiraz leaves, was passed through a XAD 2 column, and elution with methanol yielded a crude glycoconjugate composite. Further separation of this polar fraction using IIPLC semi preparative Cm18 column followed by acetylation and flash chromatography yielded Alangioside J and a new norisoprenoid β-glucopyranoside. Using 1II- and 13C-NMR techniques, the latter was shown to be the C-9 conjugate of the same (3S, 5R, 6S,9R)-megastigmane-3,9-diol as the C-3 conjugated former one.

  glycosides, Vitis vinifera, Shiraz vine leaves, glucopyranoside, trifluoroacetylation, megastigmane-3, 9-diol

  Publication DOI: 10.1080/10412905.2000.9712183
  Journal NLM ID: 9884355
  Publisher: Philadelphia, PA: Taylor & Francis
  Institutions: INRA IPV(Institut National de la Recherche Agronomique, Institut des Produits de la Vigne Jnité de Recherche Biopolymères Arômes), Montpellier, France
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
  
   
  
  Vitis vinifera cv. Shiraz
  CSDB ID 67944 (all data & tools)