Saponins in bulbs of a mutant of elephant garlic were investigated, and three new steroidal saponins named yayoisaponins A-C were obtained together with the known dioscin and aginoside. Their structures, including the relative stereochemistry, were elucidated by spectral data interpretation, while the absolute stereochemistry of the sugar moieties was assigned on the basis of a chiral gas chromatographic analysis of the acid hydrolysates. Yayoisaponins A-C and aginoside exhibited not only in vitro cytotoxicity against P388 cells at 2.1 μg/ml, but also antifungal activity against Mortierella ramanniana at 10 μg/disk.

mutant, cytotoxicity, antifungal, elephant garlic, saponin

• Compound ID: 23679
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = agigenin = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])C{6}[C@@H](O)[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H]

  Show graphically

  Show legend Show as text

  Structure type: oligomer
  C56H91O29
  Trivial name: aginoside
  Compound class: saponin glycoside, triterpenoid glycoside
  Reference(s) to other database(s): CCSD:40123, CBank-STR:12125
  
   
  
  Allium ampeloprasum (Yayoi No. 1)
  CSDB ID 63548 (all data & tools)
• Compound ID: 29589
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-3)-b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = agigenin = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])C{6}[C@@H](O)[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H]

  Show graphically

  Show legend Show as text

  Structure type: oligomer
  C56H91O29
  Trivial name: yayoisaponin A
  Compound class: triterpenoid glycoside
  
   
  
  Allium ampeloprasum (Yayoi No. 1)
  CSDB ID 62184 (all data & tools)
• Compound ID: 29590
  

  b-D-Glcp-(1-3)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = agigenin = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])C{6}[C@@H](O)[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H]

  Show graphically

  Show legend Show as text

  Structure type: oligomer
  C56H91O29
  Trivial name: yayoisaponin C
  Compound class: triterpenoid glycoside
  
   
  
  Allium ampeloprasum (Yayoi No. 1)
  CSDB ID 63547 (all data & tools)
• Compound ID: 29591
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-3)-b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = yayoisaponin B aglycon = SMILES C[C@@H]1CCC6(OC1)OC5CC4C3C{6}[C@@H](O)C2C{3}[C@@H](O)C(=O)C[C@]2(C)C3CC[C@]4(C)C5[C@@H]6C

  Show graphically

  Show legend Show as text

  Structure type: oligomer
  C56H91O29
  Trivial name: yayoisaponin B
  Compound class: triterpenoid glycoside
  
   
  
  Allium ampeloprasum (Yayoi No. 1)
  CSDB ID 63549 (all data & tools)
• Compound ID: 29592
  

  a-L-Rhap-(1-4)-+ | a-L-Rhap-(1-2)-b-D-Galp-(1-3)-Diosgenin

  Show graphically

  Show legend Show as text

  Structure type: oligomer
  C56H91O29
  Trivial name: dioscin
  Compound class: triterpenoid glycoside
  
   
  
  Allium ampeloprasum (Yayoi No. 1)
  CSDB ID 63550 (all data & tools)