Show legend Show as text

Structure type: oligomer
Trivial name: entada saponin II
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_167188,IEDB_174332,IEDB_983931,SB_192,SB_61

• Article ID: 10392
  Okada Y, Shibata S, Javellana AMJ, Kamo O "Entada saponins (ES) II and IV from the bark of Entada phaseoloides" - Chemical and Pharmaceutical Bulletin 36 (1988) 1264-1269
  

  The structures of entada saponins II and IV, isolated from the bark of Entada phaseoloides (L.) MERRILL (Leguminosae), were elucidated as 3-O-[β-D-xylopyranosyl(1→2)-α-L-arabinopyranosyl-(1→6)][β-D-glucopyranosyl(1→4)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-28-O-[β-D-apiofuranosyl(1→3)-β-D-xylopyranosyl(1→2)][2-O-acetyl)-β-D-glucopyranosyl(1→4)-6-O-((6R)-6-hydroxy-2,6-dimethyl-(2E)-2,7-octadienoyl)-β-D-glucopyranosyl oleanolic acid (1) and entagenic acid (3).

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003626909
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Meiji College of Pharmacy, Japan, Ateneo de Manila University, Manila, Philippines, JEOL Ltd., Japan
  
   
  
  Entada phaseoloides
  CSDB ID 119433 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: entada saponin IV
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_167188,IEDB_174332,IEDB_983931,SB_192,SB_61

• Article ID: 10392
  Okada Y, Shibata S, Javellana AMJ, Kamo O "Entada saponins (ES) II and IV from the bark of Entada phaseoloides" - Chemical and Pharmaceutical Bulletin 36 (1988) 1264-1269
  

  The structures of entada saponins II and IV, isolated from the bark of Entada phaseoloides (L.) MERRILL (Leguminosae), were elucidated as 3-O-[β-D-xylopyranosyl(1→2)-α-L-arabinopyranosyl-(1→6)][β-D-glucopyranosyl(1→4)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-28-O-[β-D-apiofuranosyl(1→3)-β-D-xylopyranosyl(1→2)][2-O-acetyl)-β-D-glucopyranosyl(1→4)-6-O-((6R)-6-hydroxy-2,6-dimethyl-(2E)-2,7-octadienoyl)-β-D-glucopyranosyl oleanolic acid (1) and entagenic acid (3).

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003626909
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Meiji College of Pharmacy, Japan, Ateneo de Manila University, Manila, Philippines, JEOL Ltd., Japan
  
   
  
  Entada phaseoloides
  CSDB ID 119434 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_167188,IEDB_174332,IEDB_983931,SB_192,SB_61

• Article ID: 10411
  Okada Y, Shibata S, Ikekawa T, Javellana AMJ, Kamo O "Entada saponin III, a saponin isolated from the bark of Entada phaseoloides" - Phytochemistry 26 (1987) 2789-2796
  

  The structure of Entada saponin (ES)-III, one of the main saponins of Entada phaseoloides bark, was established to be 3-O-[β-d-xylopyranosyl(1→2)-α-l-arabinopyranosyl(1→6)] [β-d-glucopyranosyl(1→4)]-2-acetamido-2-deoxy-β-d-glucopyranosyl-28-O-[β-d-apiofuranosyl(1→3)-β-d-xylopyranosyl(1→2)] [(2-O-acetoxyl)-β-d-glucopyranosyl-(1→4)] (6−O(R)(−)2,6-dimethyl-2-trans-2,7-octadienoyl)-β-d-glucopyranosyl echinocystic acid.

  Structure determination, Leguminosae, triterpenoid saponin, echinocystic acid, Entada phaseoloides, Entada saponin (ES)-III

  Publication DOI: 10.1016/S0031-9422(00)83592-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: National Cancer Center Research Institute, Tokyo, Japan, Meiji College of Pharmacy, Tokyo, Japan, Ateneo de Manila University, Manila, Philippines, Jeol Ltd, Tokyo, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, FAB-MS, GC-MS, acid hydrolysis, methanolysis, HPLC, alkaline hydrolysis, partial methanolysis, CC
  
   
  
  Entada phaseoloides
  CSDB ID 145537 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_167188,IEDB_174332,IEDB_983931,SB_192,SB_61

• Article ID: 10411
  Okada Y, Shibata S, Ikekawa T, Javellana AMJ, Kamo O "Entada saponin III, a saponin isolated from the bark of Entada phaseoloides" - Phytochemistry 26 (1987) 2789-2796
  

  The structure of Entada saponin (ES)-III, one of the main saponins of Entada phaseoloides bark, was established to be 3-O-[β-d-xylopyranosyl(1→2)-α-l-arabinopyranosyl(1→6)] [β-d-glucopyranosyl(1→4)]-2-acetamido-2-deoxy-β-d-glucopyranosyl-28-O-[β-d-apiofuranosyl(1→3)-β-d-xylopyranosyl(1→2)] [(2-O-acetoxyl)-β-d-glucopyranosyl-(1→4)] (6−O(R)(−)2,6-dimethyl-2-trans-2,7-octadienoyl)-β-d-glucopyranosyl echinocystic acid.

  Structure determination, Leguminosae, triterpenoid saponin, echinocystic acid, Entada phaseoloides, Entada saponin (ES)-III

  Publication DOI: 10.1016/S0031-9422(00)83592-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: National Cancer Center Research Institute, Tokyo, Japan, Meiji College of Pharmacy, Tokyo, Japan, Ateneo de Manila University, Manila, Philippines, Jeol Ltd, Tokyo, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, FAB-MS, GC-MS, acid hydrolysis, methanolysis, HPLC, alkaline hydrolysis, partial methanolysis, CC
  
   
  
  Entada phaseoloides
  CSDB ID 245537 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_167188,IEDB_174332,IEDB_983931,SB_192,SB_61

• Article ID: 10411
  Okada Y, Shibata S, Ikekawa T, Javellana AMJ, Kamo O "Entada saponin III, a saponin isolated from the bark of Entada phaseoloides" - Phytochemistry 26 (1987) 2789-2796
  

  The structure of Entada saponin (ES)-III, one of the main saponins of Entada phaseoloides bark, was established to be 3-O-[β-d-xylopyranosyl(1→2)-α-l-arabinopyranosyl(1→6)] [β-d-glucopyranosyl(1→4)]-2-acetamido-2-deoxy-β-d-glucopyranosyl-28-O-[β-d-apiofuranosyl(1→3)-β-d-xylopyranosyl(1→2)] [(2-O-acetoxyl)-β-d-glucopyranosyl-(1→4)] (6−O(R)(−)2,6-dimethyl-2-trans-2,7-octadienoyl)-β-d-glucopyranosyl echinocystic acid.

  Structure determination, Leguminosae, triterpenoid saponin, echinocystic acid, Entada phaseoloides, Entada saponin (ES)-III

  Publication DOI: 10.1016/S0031-9422(00)83592-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: National Cancer Center Research Institute, Tokyo, Japan, Meiji College of Pharmacy, Tokyo, Japan, Ateneo de Manila University, Manila, Philippines, Jeol Ltd, Tokyo, Japan
  Methods: 13C NMR, 1H NMR, EI-MS, FAB-MS, GC-MS, acid hydrolysis, methanolysis, HPLC, alkaline hydrolysis, partial methanolysis, CC
  
   
  
  Entada phaseoloides
  CSDB ID 245538 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 651 [M+Na]+
C₃₂H₅₂O₁₂
Trivial name: anatolioside A
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10520
  Calis I, Yuruker A, Ruegger H, Wright AD, Sticher O "Anatoliosides: Five Novel acyclic monoterpene glycosides from Viburnum orientale" - Helvetica Chimica Acta 76 (1993) 416-424
  

  Five new acyclic monoterpene glycosides 1–5 were isolated from the leaves of Viburnum orientale (Caprifoliaceae). Anatolioside (1) is a monoterpene diglycoside and its structure was elucidated as linalo-6-yl 2′-O-(α-l-rhamnopyranosyl)β-d-glucopyranoside (arbitrary numbering of linalool moiety). Compounds 2–5 are all derivatives of 1, containing additional monoterpene and sugar units, connected by ester and glycoside bonds. Their structures were established as linalo-6-yl O-[(2E,6R)-6-hydroxy-2, 6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″‴→2″″)-β-d-glucopyranoside ( = anatolioside A; 2), linalo-6-yl O-β-d-glucopyranosyl-(1‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)–β-d-glucopyranoside ( = anatolioside B; 3), linalo-6-yl O-β-dribo-hexopyranos-3-ulosyl-(1′‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)-β-d-glucopyranoside ( = anatolioside C; 4) and linalo-6-yl O-[(2E, 6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1″‴→2″″)-O-β-d-glucopyranosly-(1″″→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl(1″→2′)-β-d-glucopyranoside ( = anatolioside d; 5). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation and methylation).

  Publication DOI: 10.1002/hlca.19930760125
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zürich, Laboratory of Inorganic Chemistry, Zürich, Switzerland, Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, acid hydrolysis, alkaline hydrolysis, UV, MPLC, acetylation analysis
  
   
  
  Viburnum orientale
  CSDB ID 129525 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 813 [M+Na]+
C₃₈H₆₂O₁₇
Trivial name: anatolioside B
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10520
  Calis I, Yuruker A, Ruegger H, Wright AD, Sticher O "Anatoliosides: Five Novel acyclic monoterpene glycosides from Viburnum orientale" - Helvetica Chimica Acta 76 (1993) 416-424
  

  Five new acyclic monoterpene glycosides 1–5 were isolated from the leaves of Viburnum orientale (Caprifoliaceae). Anatolioside (1) is a monoterpene diglycoside and its structure was elucidated as linalo-6-yl 2′-O-(α-l-rhamnopyranosyl)β-d-glucopyranoside (arbitrary numbering of linalool moiety). Compounds 2–5 are all derivatives of 1, containing additional monoterpene and sugar units, connected by ester and glycoside bonds. Their structures were established as linalo-6-yl O-[(2E,6R)-6-hydroxy-2, 6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″‴→2″″)-β-d-glucopyranoside ( = anatolioside A; 2), linalo-6-yl O-β-d-glucopyranosyl-(1‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)–β-d-glucopyranoside ( = anatolioside B; 3), linalo-6-yl O-β-dribo-hexopyranos-3-ulosyl-(1′‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)-β-d-glucopyranoside ( = anatolioside C; 4) and linalo-6-yl O-[(2E, 6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1″‴→2″″)-O-β-d-glucopyranosly-(1″″→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl(1″→2′)-β-d-glucopyranoside ( = anatolioside d; 5). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation and methylation).

  Publication DOI: 10.1002/hlca.19930760125
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zürich, Laboratory of Inorganic Chemistry, Zürich, Switzerland, Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, acid hydrolysis, alkaline hydrolysis, UV, MPLC, acetylation analysis
  
   
  
  Viburnum orientale
  CSDB ID 229525 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 811 [M+Na]+
C₃₈H₆₀O₁₇
Trivial name: anatolioside C
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10520
  Calis I, Yuruker A, Ruegger H, Wright AD, Sticher O "Anatoliosides: Five Novel acyclic monoterpene glycosides from Viburnum orientale" - Helvetica Chimica Acta 76 (1993) 416-424
  

  Five new acyclic monoterpene glycosides 1–5 were isolated from the leaves of Viburnum orientale (Caprifoliaceae). Anatolioside (1) is a monoterpene diglycoside and its structure was elucidated as linalo-6-yl 2′-O-(α-l-rhamnopyranosyl)β-d-glucopyranoside (arbitrary numbering of linalool moiety). Compounds 2–5 are all derivatives of 1, containing additional monoterpene and sugar units, connected by ester and glycoside bonds. Their structures were established as linalo-6-yl O-[(2E,6R)-6-hydroxy-2, 6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″‴→2″″)-β-d-glucopyranoside ( = anatolioside A; 2), linalo-6-yl O-β-d-glucopyranosyl-(1‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)–β-d-glucopyranoside ( = anatolioside B; 3), linalo-6-yl O-β-dribo-hexopyranos-3-ulosyl-(1′‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)-β-d-glucopyranoside ( = anatolioside C; 4) and linalo-6-yl O-[(2E, 6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1″‴→2″″)-O-β-d-glucopyranosly-(1″″→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl(1″→2′)-β-d-glucopyranoside ( = anatolioside d; 5). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation and methylation).

  Publication DOI: 10.1002/hlca.19930760125
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zürich, Laboratory of Inorganic Chemistry, Zürich, Switzerland, Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, acid hydrolysis, alkaline hydrolysis, UV, MPLC, acetylation analysis
  
   
  
  Viburnum orientale
  CSDB ID 279525 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 979 [M+Na]+
C₄₈H₇₆O₁₉
Trivial name: anatolioside D
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10520
  Calis I, Yuruker A, Ruegger H, Wright AD, Sticher O "Anatoliosides: Five Novel acyclic monoterpene glycosides from Viburnum orientale" - Helvetica Chimica Acta 76 (1993) 416-424
  

  Five new acyclic monoterpene glycosides 1–5 were isolated from the leaves of Viburnum orientale (Caprifoliaceae). Anatolioside (1) is a monoterpene diglycoside and its structure was elucidated as linalo-6-yl 2′-O-(α-l-rhamnopyranosyl)β-d-glucopyranoside (arbitrary numbering of linalool moiety). Compounds 2–5 are all derivatives of 1, containing additional monoterpene and sugar units, connected by ester and glycoside bonds. Their structures were established as linalo-6-yl O-[(2E,6R)-6-hydroxy-2, 6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″‴→2″″)-β-d-glucopyranoside ( = anatolioside A; 2), linalo-6-yl O-β-d-glucopyranosyl-(1‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)–β-d-glucopyranoside ( = anatolioside B; 3), linalo-6-yl O-β-dribo-hexopyranos-3-ulosyl-(1′‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)-β-d-glucopyranoside ( = anatolioside C; 4) and linalo-6-yl O-[(2E, 6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1″‴→2″″)-O-β-d-glucopyranosly-(1″″→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl(1″→2′)-β-d-glucopyranoside ( = anatolioside d; 5). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation and methylation).

  Publication DOI: 10.1002/hlca.19930760125
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zürich, Laboratory of Inorganic Chemistry, Zürich, Switzerland, Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, acid hydrolysis, alkaline hydrolysis, UV, MPLC, acetylation analysis
  
   
  
  Viburnum orientale
  CSDB ID 279526 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: anatolioside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 10520
  Calis I, Yuruker A, Ruegger H, Wright AD, Sticher O "Anatoliosides: Five Novel acyclic monoterpene glycosides from Viburnum orientale" - Helvetica Chimica Acta 76 (1993) 416-424
  

  Five new acyclic monoterpene glycosides 1–5 were isolated from the leaves of Viburnum orientale (Caprifoliaceae). Anatolioside (1) is a monoterpene diglycoside and its structure was elucidated as linalo-6-yl 2′-O-(α-l-rhamnopyranosyl)β-d-glucopyranoside (arbitrary numbering of linalool moiety). Compounds 2–5 are all derivatives of 1, containing additional monoterpene and sugar units, connected by ester and glycoside bonds. Their structures were established as linalo-6-yl O-[(2E,6R)-6-hydroxy-2, 6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″‴→2″″)-β-d-glucopyranoside ( = anatolioside A; 2), linalo-6-yl O-β-d-glucopyranosyl-(1‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)–β-d-glucopyranoside ( = anatolioside B; 3), linalo-6-yl O-β-dribo-hexopyranos-3-ulosyl-(1′‴→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl-(1″→2′)-β-d-glucopyranoside ( = anatolioside C; 4) and linalo-6-yl O-[(2E, 6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1″‴→2″″)-O-β-d-glucopyranosly-(1″″→6‴)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1‴→4″)-O-α-l-rhamnopyranosyl(1″→2′)-β-d-glucopyranoside ( = anatolioside d; 5). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation and methylation).

  Publication DOI: 10.1002/hlca.19930760125
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zürich, Laboratory of Inorganic Chemistry, Zürich, Switzerland, Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, acid hydrolysis, alkaline hydrolysis, UV, MPLC, acetylation analysis
  
   
  
  Viburnum orientale
  CSDB ID 279527 (all data & tools)
• Article ID: 10521
  Calis I, Yuruker A, Ruegger H, Wright AD, Sticher O "Anatolioside E: A new acyclic monoterpene glycoside from Viburnum orientale" - Helvetica Chimica Acta 76 (1993) 2563-2569
  

  A new open-chain monoterpene glycoside, anatolioside E (1), was isolated from the leaves of Viburnum orientale in addition to three known acyclic monoterpene glycosides, betulalbusides A (2) and B (3), and 2(E)-2,6-dimethyl-2,7-octadien-1,6-diol-6-O-β-d-glucopyranoside(4). The structure of anatolioside E (1) was elucidated on the basis of chemical and spectral data as 6-O-[β-d-glucopyransoyl-(1‴‴→6‴″)-2-(E),6(R),2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1‴″→2″″)-β-d-glucopyranosyl-(1″″→6‴)-2-(E),6(R),2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1‴→4″)-α-l-rhamnopyranosyl-(1″″→2′)-β-d-glucopyranosyl]linalool.

  Publication DOI: 10.1002/hlca.19930760716
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zürich, Laboratory of Inorganic Chemistry, Zürich, Switzerland, Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, alkaline hydrolysis, UV, MPLC, acetylation analysis
  
   
  
  Viburnum orientale
  CSDB ID 279536 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1141 [M+Na]+
C₅₄H₈₆O₂₄
Trivial name: anatolioside E
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10521
  Calis I, Yuruker A, Ruegger H, Wright AD, Sticher O "Anatolioside E: A new acyclic monoterpene glycoside from Viburnum orientale" - Helvetica Chimica Acta 76 (1993) 2563-2569
  

  A new open-chain monoterpene glycoside, anatolioside E (1), was isolated from the leaves of Viburnum orientale in addition to three known acyclic monoterpene glycosides, betulalbusides A (2) and B (3), and 2(E)-2,6-dimethyl-2,7-octadien-1,6-diol-6-O-β-d-glucopyranoside(4). The structure of anatolioside E (1) was elucidated on the basis of chemical and spectral data as 6-O-[β-d-glucopyransoyl-(1‴‴→6‴″)-2-(E),6(R),2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1‴″→2″″)-β-d-glucopyranosyl-(1″″→6‴)-2-(E),6(R),2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1‴→4″)-α-l-rhamnopyranosyl-(1″″→2′)-β-d-glucopyranosyl]linalool.

  Publication DOI: 10.1002/hlca.19930760716
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zürich, Laboratory of Inorganic Chemistry, Zürich, Switzerland, Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, alkaline hydrolysis, UV, MPLC, acetylation analysis
  
   
  
  Viburnum orientale
  CSDB ID 129533 (all data & tools)

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Structure type: monomer ; 329 [M-H]-
C₁₆H₂₅O₇
Trivial name: monoterpene glycoside
Compound class: saponin glycoside

• Article ID: 11144
  Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" - Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
  

  From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.

  13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside

  Publication DOI: 10.1248/cpb.45.807
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
  Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
  
   
  
  Acacia concinna
  CSDB ID 60323 (all data & tools)

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Structure type: monomer ; 315 [M-H]-
C₁₅H₂₃O₇
Trivial name: monoterpene glycoside
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332

• Article ID: 11144
  Kiuchi F, Gafur A, Obata T, Tachibana A, Tsuda Y "Acacia concinna saponins. II. Structures of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction" - Chemical and Pharmaceutical Bulletin 45(5) (1997) 807-812
  

  From the AcOEt-soluble fraction of the alkaline hydrolyzate of the highly polar saponin fraction of pods of Acacia concinna, two monoterpenes, (2E)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid (menthiafolic acid, 1) and (2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid (4), and their glycosides, (6R)- and (6S)-menthiafolic acid-6-O-β-D-quinovoside (2a and 2b) and (6R)- and (6S)-menthiafolic acid-6-O-β-D-xyloside (3a and 3b), were isolated. A more polar fraction gave, after methylation with diazomethane, (6R)- and (6S)-(2E)-6-hydroxy-2-hydroxymethyl-6-methyl-2,7-octadienoic acid-6-O-β-D-quinovoside as their methyl esters (5a and 5b). Compounds 2a, 3a, 4, 5a, and 5b are new. The structures of the above compounds were determined mainly by the application of spectroscopic methods.

  13C-NMR, monoterpene glycoside, Acacia concinna, menthiafolic acid, b-D-quinovoside, b-D-xyloside

  Publication DOI: 10.1248/cpb.45.807
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kanazawa University
  Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, enzymatic hydrolysis, chemical methods, HPLC, akaline hydrolysis
  
   
  
  Acacia concinna
  CSDB ID 60325 (all data & tools)

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Structure type: oligomer ; 2195 [M+K]+
C₁₀₁H₁₆₀O₄₉
Trivial name: julibroside J1
Compound class: glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_136907,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 12896
  Zou K, Zhao Y, Tu G, Cui J, Jia Z, Zhang R "Two diastereomeric saponins with cytotoxic activity from Albizia julibrissin" - Carbohydrate Research 324(3) (2000) 182-188
  

  Two diastereomeric saponins, julibrosides J1 (1) and J9 (2), both of which show cytotoxic activity, were obtained from the stem bark of Albizia julibrissin Durazz. On the basis of chemical and spectral evidence [L.B. Ma et al., Carbohydr. Res., 281 (1996) 35–46], the structure of 1 was revised as 3-O-[β-d-xylopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl]-21-O-{(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-[4-O-((6R)-2-trans-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)-2,7-octadienoyl)-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid-28-O-β-d-glucopyranosyl-(1→3)-[α-l-arabinofuranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester. The diastereoisomer 2 of 1 was identified as 3-O-[β-d-xylopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl]-21-O-{(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-[4-O-((6S)-2-trans-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)-2,7-octadienoyl)-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid-28-O-β-d-glucopyranosyl-(1→3)-[α-l-arabinofuranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl ester. Saponin 2 is a new saponin named julibroside J9. Both julibrosides J1 and J9 show good inhibitory action against the KB cancer cell line in vitro.

  cytotoxicity, diastereomer, Albizia julibrissin, julibroside J1, julibroside J9

  NCBI PubMed ID: 10724532
  Publication DOI: 10.1016/s0008-6215(99)00294-3
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: Zhao Y
  Institutions: Beijing Institute of Microchemistry, Beijing, China, School of Pharmaceutical Sciences, Division of Natural Medicinal Chemistry, Beijing Medical University, Beijing, China, Department of Pharmacognosy, Toho University, Chiba, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, acid hydrolysis, HPLC, extraction, CC, HR-ESI-MS, evaporation, centrifugation
  
   
  
  Albizia julibrissin
  CSDB ID 68897 (all data & tools)