Total of eighteen steroidal saponins were isolated from the rhizomes of Hosta sieboldii, one of which appeared to be the first isolation from a plant source and six to be new compounds. The structures of the new saponins were determined by spectral data and a few chemical transformations to be (25R)-2 alpha,3 beta-dihydroxy-5 alpha-spirostan-12-one (manogenin) 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(l-->4)-beta-D-galacltopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-5 alpha-spirost-9-en-12-one (9,11-dehydromanogenin) 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, 9,11-dehydromanogenin 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-26-beta-D-glucopyranosyloxy-22-methoxy-5 alpha-furostan-12-one 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside}, (25R)-2 alpha,3 beta-dihydroxy-26-beta-D-glucopyranosyloxy-22-methoxy-5 alpha-furost-9-en-12-one 3-O-{O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} and (25R)-5 alpha-spirostan-2 alpha,3 beta,12 beta-triol 3-O-(O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranoside), respectively. Cytostatic activity of the isolated saponins on leukaemia HL-60 cells was examined.

steroidal saponins, Liliaceae, cytostatic activity, furostanol saponins, spirostanol saponins, rhizomes, HL-60 cells, Hosta sieboldii

• Compound ID: 23888
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = gitogenin = SMILES C[C@@H]1[C@]2(OC[C@H](C)CC2)O[C@@]3([H])C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]31[H]

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  Structure type: oligomer
  Trivial name: F-gitonin
  Compound class: saponin glycoside, glycoside, triterpenoid glycoside
  Reference(s) to other database(s): CCSD:20155, CBank-STR:12106
  
   
  
  Hosta sieboldii
  CSDB ID 61559 (all data & tools)
• Compound ID: 28944
  

  b-D-Galp-(1-3)-Subst Subst = gitogenin = SMILES C[C@@H]1[C@]2(OC[C@H](C)CC2)O[C@@]3([H])C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]31[H]

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  Structure type: monomer ; 593 [M-H]-
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61554 (all data & tools)
• Compound ID: 28945
  

  a-L-Rhap-(1-2)-b-D-Galp-(1-3)-Subst Subst = gitogenin = SMILES C[C@@H]1[C@]2(OC[C@H](C)CC2)O[C@@]3([H])C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]31[H]

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  Structure type: oligomer
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61555 (all data & tools)
• Compound ID: 28946
  

  b-D-Glcp-(1-4)-+ | a-L-Rhap-(1-2)-b-D-Galp-(1-3)-Subst Subst = gitogenin = SMILES C[C@@H]1[C@]2(OC[C@H](C)CC2)O[C@@]3([H])C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]31[H]

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  Structure type: oligomer
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61556 (all data & tools)
• Compound ID: 28947
  

  b-D-Glcp-(1-4)-+ | a-L-Rhap-(1-2)-b-D-Galp-(1-3)-Subst Subst = tigogenin = 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: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61928 (all data & tools)
• Compound ID: 28948
  

  b-D-Glcp-(1-26)-+ | a-L-Rhap-(1-2)-b-D-Galp-(1-3)-Subst22Me Subst = 25R-5α-furostan-2α,3β,22,26-tetrol = SMILES C[C@H]1[C@H]2[C@@H](O{22}C1(O)CC[C@H]({26}[CH2]O)C)C[C@@H]3[C@]2(C)CC[C@H]4[C@H]3CC[C@@H]5[C@]4(C)C[C@@H](O){3}[C@H](O)C5

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  Structure type: oligomer
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61557 (all data & tools)
• Compound ID: 28949
  

  b-D-Glcp-(1-26)-+ | b-D-Glcp-(1-4)-+ | | | a-L-Rhap-(1-2)-b-D-Galp-(1-3)-Subst22Me Subst = 25R-5α-furostan-2α,3β,22,26-tetrol = SMILES C[C@H]1[C@H]2[C@@H](O{22}C1(O)CC[C@H]({26}[CH2]O)C)C[C@@H]3[C@]2(C)CC[C@H]4[C@H]3CC[C@@H]5[C@]4(C)C[C@@H](O){3}[C@H](O)C5

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  Structure type: oligomer
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61558 (all data & tools)
• Compound ID: 28950
  

  a-L-Rhap-(1-2)-b-D-Galp-(1-3)-Subst Subst = 25R-5α-spirostan-2α,3β,12β-triol = SMILES CC1CCC6(CC1)CC5CC4C3CCC2C{3}[C@@H](O){2}[C@H](O)C[C@]2(C)C3C{12}[C@@H](O)[C@]4(C)C5[C@H]6C

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  Structure type: oligomer ; 755 [M-H]-
  C39H64O14
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61929 (all data & tools)
• Compound ID: 28951
  

  b-D-Glcp-(1-2)-+ | a-L-Rhap-(1-4)-b-D-Xylp-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = gitogenin = SMILES C[C@@H]1[C@]2(OC[C@H](C)CC2)O[C@@]3([H])C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]31[H]

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  Structure type: oligomer
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61560 (all data & tools)
• Compound ID: 28952
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = hecogenin = SMILES C[C@@H]1CC[C@]2(O[C@@]3([H])C[C@@]([C@@]4(C)[C@@]3([H])[C@@H]2C)([H])[C@]5([H])CC[C@@]6([H])C{3}[C@@H](O)CC[C@]6(C)[C@@]5([H])CC4=O)OC1

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  Structure type: oligomer
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61561 (all data & tools)
• Compound ID: 28953
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = manogenin = SMILES C[C@@H]1CC[C@]2(OC1)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@]3(C)C(C[C@H]5[C@H]4CC[C@@H]6[C@]5(C)C{2}[C@@H](O){3}[C@H](O)C6)=O)O2

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  Structure type: oligomer
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61562 (all data & tools)
• Compound ID: 28954
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = 9,11-dehydromanogenin = SMILES C[C@@H]1CC[C@]2(OC1)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@]3(C)C(C=C5[C@H]4CC[C@@H]6[C@]5(C)C{2}[C@@H](O){3}[C@H](O)C6)=O)O2

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  Structure type: oligomer
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61563 (all data & tools)
• Compound ID: 28955
  

  b-D-Glcp-(1-2)-+ | a-L-Rhap-(1-4)-b-D-Xylp-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = manogenin = SMILES C[C@@H]1CC[C@]2(OC1)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@]3(C)C(C[C@H]5[C@H]4CC[C@@H]6[C@]5(C)C{2}[C@@H](O){3}[C@H](O)C6)=O)O2

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  Structure type: oligomer
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61564 (all data & tools)
• Compound ID: 28956
  

  b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = manogenin = SMILES C[C@@H]1CC[C@]2(OC1)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@]3(C)C(C[C@H]5[C@H]4CC[C@@H]6[C@]5(C)C{2}[C@@H](O){3}[C@H](O)C6)=O)O2

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  Structure type: oligomer ; 931 [M-H]-
  C45H72O20
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61565 (all data & tools)
• Compound ID: 28957
  

  b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = 9,11-dehydromanogenin = SMILES C[C@@H]1CC[C@]2(OC1)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@]3(C)C(C=C5[C@H]4CC[C@@H]6[C@]5(C)C{2}[C@@H](O){3}[C@H](O)C6)=O)O2

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  Structure type: oligomer ; 929 [M-H]-
  C45H70O20
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61566 (all data & tools)
• Compound ID: 28958
  

  b-D-Glcp-(1-2)-+ | a-L-Rhap-(1-4)-b-D-Xylp-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = 9,11-dehydromanogenin = SMILES C[C@@H]1CC[C@]2(OC1)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@]3(C)C(C=C5[C@H]4CC[C@@H]6[C@]5(C)C{2}[C@@H](O){3}[C@H](O)C6)=O)O2

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  Structure type: oligomer ; 1207 [M-H]-
  C56H88O28
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61567 (all data & tools)
• Compound ID: 28959
  

  b-D-Xylp-(1-3)-+ b-D-Glcp-(1-26)-+ | | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst22Me Subst = 25R-2α,3β,22,26-tetrahydroxy-5α-spirostan-12-one = SMILES C[C@@H]({26}CO)CC{22}[C@]5(O)OC4CC3C2CCC1C{3}[C@@H](O){2}[C@H](O)C[C@]1(C)C2CC(=O)[C@]3(C)C4[C@H]5C

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  Structure type: oligomer ; 1257 [M-H]-
  C57H94O30
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61568 (all data & tools)
• Compound ID: 28960
  

  b-D-Xylp-(1-3)-+ b-D-Glcp-(1-26)-+ | | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst22Me Subst = 25R-2α,3β,22,26-tetrahydroxy-5α-spirostan-9-en-12-one = SMILES C[C@@H]({26}CO)CC{22}[C@]5(O)OC4CC3C2CCC1C{3}[C@@H](O){2}[C@H](O)C[C@]1(C)/C2=C\C(=O)[C@]3(C)C4[C@H]5C

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  Structure type: oligomer ; 1255 [M-H]-
  C57H92O30
  Compound class: triterpenoid glycoside
  
   
  
  Hosta sieboldii
  CSDB ID 61569 (all data & tools)

Squarroside C (1), a new cycloartane 3,21-bisdesmoside, was isolated from the above-ground parts of Thalictrum squarrosum. The structure of 1 was established as 3-O-[O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl]-21-O-β-D-glucopyranosyl-21(S),22(S),23(R),3β,21α,22β,30-tetrahydroxy-21,23-epoxycycloart-24-ene by 2D NMR spectroscopy and FAB-MS.

squarroside C, cycloartene bisdesmoside, Thalictrum squarrosum

• Compound ID: 30768
  

  b-D-Glcp-(1-21)-+ | a-L-Rhap-(1-6)-b-D-Glcp-(1-3)-Subst Subst = 21S,22S,23R,3β,21α,22β,30-tetrahydroxy-21,23-epoxycycloart-24-ene = SMILES CC(C)=C[C@H]1O{21}[C@@H](O)[C@@H]([C@H]2CC[C@@]3(C)[C@@H]4CC[C@H]5[C@@](C)({30}CO){3}[C@@H](O)CC[C@@]56C[C@@]46CC[C@]23C){22}[C@@H]1O

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  Structure type: oligomer ; 981 [M+Na]+
  C48H78O19
  Trivial name: squarroside C
  Compound class: saponin glycoside
  
   
  
  Thalictrum squarrosum
  CSDB ID 63372 (all data & tools)