Six novel triterpenoid saponins, named saponariosides C-H, were isolated from the whole plants of Saponaria officinalis. Their structures were established as saponarioside C (1), 3-O-β-D-xylopyranosyl-gypsogenic acid-28-O-α-D-galactopyranosyl-(1→6)-β-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside; saponarioside D (2), 3-O-β-D-xylopyranosyl-gypsogenic acid-28-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside; saponarioside E (3), 3-O-β-D-glucopyranosyl-gypsogenic acid-28-O-β-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside; saponarioside F (4), 3-O-β-D-xylopyranosyl-16α-hydroxygypsogenic acid-28-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside; saponarioside G (5), 3-O-β-D-xylopyranosyl-16α-hydroxygypsogenic acid-28-O-β-D-glucopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside; and saponarioside H (6), 3-O-β-D-xylopyranosyl-gypsogenic acid-28-O-β-D-glucopyranoside, by a combination of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC, and NOESY) studies and chemical degradation.

triterpenoid saponin, Saponaria officinalis, saponarioside C

• Compound ID: 30585
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-3)-+ | | | a-D-Galp-(1-6)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst Subst = gypsogenic acid = SMILES C[C@]12CC{3}[C@H](O)[C@@](C)({23}C(O)=O)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)CC[C@]5({28}C(O)=O)[C@H]4CC(C)(C)CC5

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  Structure type: oligomer ; 1289 [M+Na]+
  C59H94O29
  Trivial name: saponarioside C
  Compound class: saponin glycoside
  
   
  
  Saponaria officinalis
  CSDB ID 63150 (all data & tools)
• Compound ID: 30586
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-3)-+ | | | b-D-Glcp-(1-2)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst Subst = gypsogenic acid = SMILES C[C@]12CC{3}[C@H](O)[C@@](C)({23}C(O)=O)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)CC[C@]5({28}C(O)=O)[C@H]4CC(C)(C)CC5

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  Structure type: oligomer ; 1265 [M+H]-
  C59H94O29
  Trivial name: saponarioside D
  Compound class: saponin glycoside
  
   
  
  Saponaria officinalis
  CSDB ID 63151 (all data & tools)
• Compound ID: 30587
  

  b-D-Glcp-(1-3)-+ | b-D-Glcp-(1-3)-+ | | | b-D-Glcp-(1-2)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst Subst = gypsogenic acid = SMILES C[C@]12CC{3}[C@H](O)[C@@](C)({23}C(O)=O)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)CC[C@]5({28}C(O)=O)[C@H]4CC(C)(C)CC5

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  Structure type: oligomer ; 1319 [M+Na]+
  C60H96O30
  Trivial name: saponarioside E
  Compound class: saponin glycoside
  
   
  
  Saponaria officinalis
  CSDB ID 63152 (all data & tools)
• Compound ID: 30588
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-3)-+ | | | b-D-Glcp-(1-2)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst Subst = 16α-hydroxygypsogenic acid = SMILES CC1(C)CC[C@@]2({28}C(=O)O)[C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC{3}[C@H](O)[C@@](C)({23}C(=O)O)[C@@H]4CC[C@@]3(C)[C@]1(C)C{16}[C@H]2O

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  Structure type: oligomer ; 1305 [M+Na]+
  C59H94O30
  Trivial name: saponarioside F
  Compound class: saponin glycoside
  
   
  
  Saponaria officinalis
  CSDB ID 63153 (all data & tools)
• Compound ID: 30589
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-6)-+ | | | b-D-Glcp-(1-3)-b-D-Glcp-(1-28)-Subst Subst = 16α-hydroxygypsogenic acid = SMILES CC1(C)CC[C@@]2({28}C(=O)O)[C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC{3}[C@H](O)[C@@](C)({23}C(=O)O)[C@@H]4CC[C@@]3(C)[C@]1(C)C{16}[C@H]2O

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  Structure type: oligomer ; 1143 [M+Na]+
  C53H84O25
  Trivial name: saponarioside G
  Compound class: saponin glycoside
  
   
  
  Saponaria officinalis
  CSDB ID 63154 (all data & tools)
• Compound ID: 30590
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-28)-Subst Subst = 16α-hydroxygypsogenic acid = SMILES CC1(C)CC[C@@]2({28}C(=O)O)[C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC{3}[C@H](O)[C@@](C)({23}C(=O)O)[C@@H]4CC[C@@]3(C)[C@]1(C)C{16}[C@H]2O

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  Structure type: oligomer ; 803 [M+Na]+
  C41H64O14
  Trivial name: saponarioside H
  Compound class: saponin glycoside
  
   
  
  Saponaria officinalis
  CSDB ID 63155 (all data & tools)