The structures of two new monodesmosidic spirostanosides and a new bisdesmosidic furostanol glycoside isolated from the roots of Asparagus africanus Lam. (Liliaceae) have been elucidated as (25R)-3β-hydroxy-5β-spirostan-12-one 3-O-{β-D-glucopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→6)]-[β-D-glucopyranoside} (1), (25R)-5β-spirostan-3β-ol 3-O-{β- D-glucopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→6)]-[β-D-glucopyranoside} (2) and 26-O-β-D-glucopyranosyl]-22α-methoxy(25R)-furostan-3β,26-diol 3-O-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranoside} (3), respectively, by the combined use of one and two dimensional NMR experiments. The complete 13C and 1H assignments of the peracetyl spirostanosides and the furostanol oligoside were derived. The interconversions between the methoxyl and hydroxyl group at C-22 of the furostanol glycoside was investigated and the genuine furostanol oligoside of A. africanus appears to be the hydroxyl type based on the comparative study of the methanol, pyridine and dioxane extracts.

Liliaceae, Asparagus africanus, spirostanol glycoside furostanol glycoside, gloriogenin, smilagenin

• Compound ID: 30254
  

  a-L-Arap-(1-6)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst Subst = (25R)-3β-hydroxy-5β-spirostan-12-one = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@@H](C)[C@@]1([C@]34C)[H])C[C@@]3([H])[C@]5([H])CC[C@]6([H])C{3}[C@@H](O)CC[C@]6(C)[C@@]5([H])CC4=O

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  Structure type: oligomer ; 909 [M+Na]+
  C44H70O18
  Compound class: saponin glycoside
  
   
  
  Asparagus africanus
  CSDB ID 62722 (all data & tools)
• Compound ID: 30255
  

  a-L-Arap2Ac3Ac4Ac-(1-6)-+ | b-D-Glcp2Ac3Ac4Ac6Ac-(1-2)-b-D-Glcp3Ac4Ac-(1-3)-Subst Subst = (25R)-3β-hydroxy-5β-spirostan-12-one = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@@H](C)[C@@]1([C@]34C)[H])C[C@@]3([H])[C@]5([H])CC[C@]6([H])C{3}[C@@H](O)CC[C@]6(C)[C@@]5([H])CC4=O

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  Structure type: oligomer
  Compound class: saponin glycoside
  
   
  
  Asparagus africanus
  CSDB ID 62723 (all data & tools)
• Compound ID: 30256
  

  a-L-Arap-(1-6)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst Subst = (25R)-5β-spirostan-3β-ol = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC[C@]6([H])C{3}[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H]

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  Structure type: oligomer ; 896 [M+Na]+
  C44H72O17
  Compound class: saponin glycoside
  
   
  
  Asparagus africanus
  CSDB ID 62724 (all data & tools)
• Compound ID: 30257
  

  a-L-Arap2Ac3Ac4Ac-(1-6)-+ | b-D-Glcp2Ac3Ac4Ac6Ac-(1-2)-b-D-Glcp3Ac4Ac-(1-3)-Subst Subst = (25R)-5β-spirostan-3β-ol = SMILES [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC[C@]6([H])C{3}[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H]

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  Structure type: oligomer
  Compound class: saponin glycoside
  
   
  
  Asparagus africanus
  CSDB ID 62725 (all data & tools)
• Compound ID: 30258
  

  b-D-Glcp-(1-26)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst22Me Subst = 25R-5β-furostan-3β,22α,26-triol = SMILES C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@@H]5C{3}[C@@H](O)CC[C@]5(C)[C@H]4CC[C@@]32C)O{22}[C@]1(O)CC[C@@H](C){26}CO

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  Structure type: oligomer ; 936 [M+H]+
  C46H78O19
  Compound class: saponin glycoside
  
   
  
  Asparagus africanus
  CSDB ID 62726 (all data & tools)
• Compound ID: 30259
  

  b-D-Glcp-(1-26)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Subst Subst = 25R-5β-furostan-3β,22α,26-triol = SMILES C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC[C@@H]5C{3}[C@@H](O)CC[C@]5(C)[C@H]4CC[C@@]32C)O{22}[C@]1(O)CC[C@@H](C){26}CO

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  Structure type: oligomer
  Compound class: saponin glycoside
  
   
  
  Asparagus africanus
  CSDB ID 62727 (all data & tools)