Phytochemical examination of the fresh bulbs of Allium schubertii led to the isolation of four new steroidal saponins together with a known saponin. The structures of the new saponins were established by spectroscopic data, hydrolysis and chemical correlation as (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-benzoyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[3-O-benzoyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glu-copyranosyl-(1→4)-β-d-galactopyranoside, (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaroyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside and 26-O-β-d-glucopyranosyl-(25R and S)-5α-furostan-2α,3β,6β,22ξ,26-pentol 3-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, respectively.

steroidal saponins, furostanol saponin, Allium schubertii, Liliaccae, bulbs, spirostanol saponins, aginoside, turoside A, benzoic acid esters, 3-hydroxy-3-methylglutaric acid ester

• Compound ID: 24998
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-2)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = 5α-spirostan-2α,3β,6β-triol = SMILES [H][C@]1(O[C@@]2(OCC(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]

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  Structure type: oligomer ; 1066 [M]-
  C50H82O24
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:2190, CBank-STR:12124
  
   
  
  Allium schubertii
  CSDB ID 145889 (all data & tools)
• Compound ID: 24999
  

  b-D-Glcp-(1-2)-+ | b-D-Xylp4Bz-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = 5α-spirostan-2α,3β,6β-triol = SMILES [H][C@]1(O[C@@]2(OCC(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]; Bz = benzoic acid

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  Structure type: oligomer ; 1152 [M-H2O]-
  C57H86O25
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:2195, CBank-STR:13130
  
   
  
  Allium schubertii
  CSDB ID 145891 (all data & tools)
• Compound ID: 25000
  

  b-D-Glcp-(1-2)-+ | b-D-Xylp3Bz-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = 5α-spirostan-2α,3β,6β-triol = SMILES [H][C@]1(O[C@@]2(OCC(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]; Bz = benzoic acid

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  Structure type: oligomer ; 1170 [M]-
  C57H86O25
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:2210, CBank-STR:13132
  
   
  
  Allium schubertii
  CSDB ID 145893 (all data & tools)
• Compound ID: 25001
  

  b-D-Glcp-(1-2)-+ | 3HO3MeGlt-(1-4)-b-D-Xylp-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = 5α-spirostan-2α,3β,6β-triol = SMILES [H][C@]1(O[C@@]2(OCC(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]

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  Structure type: oligomer ; 1209 [M-H]-
  C58H90O28
  Trivial name: configuration at aglycon C25 is unknown
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:2251, CBank-STR:13137
  
   
  
  Allium schubertii
  CSDB ID 145896 (all data & tools)
• Compound ID: 25002
  

  b-D-Glcp-(1-2)-+ | 3HO3MeGlt5Me-(1-4)-b-D-Xylp-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst Subst = 5α-spirostan-2α,3β,6β-triol = SMILES [H][C@]1(O[C@@]2(OCC(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]

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  Structure type: oligomer
  Compound class: saponin glycoside
  
   
  
  Allium schubertii
  CSDB ID 245896 (all data & tools)
• Compound ID: 25003
  

  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)-Subst Subst = 5α-furostan-2α,3β,6β,22,26-pentol = SMILES [H][C@]1(O{22}C(CCC(C){26}CO)(O)[C@H]2C)C[C@@]3([H])[C@]4([H])C{6}[C@@H](O)[C@@]5([H])C{3}[C@@H](O){2}[C@H](O)C[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@]12[H]

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  Structure type: oligomer ; 1245 [M-H]-
  C56H94O30
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:28259, CBank-STR:14275
  
   
  
  Allium schubertii
  CSDB ID 145898 (all data & tools)

Four new (22S)-hydroxycholestane glycosides, schubertosides A - D, have been isolated from the bulbs of Allium schubertii. Their structures were determined by spectroscopic analaysis and hydrolysis. The advanced Mosher's method was applied to determined the C-22 absolute configuration.

Liliaceae, Allium schubertii, (22S)-hydroxycholestane glycoside, schubertoside

• Compound ID: 25740
  

  a-L-Rhap-(1-3)-a-D-Galp-(1-16)-Subst Subst = 16β,22S-dihydroxycholest-4-en-3-one = SMILES CC(C)CC{22}[C@H](O)[C@@H](C)[C@H]1{16}[C@@H](O)C[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O

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  Structure type: oligomer ; 725 [M+H]+
  C39H64O12
  Trivial name: schubertoside A
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:31066, CBank-STR:3842
  
   
  
  Allium schubertii
  CSDB ID 119852 (all data & tools)
• Compound ID: 25741
  

  a-L-Rhap-(1-3)-a-D-Galp-(1-16)-Subst Subst = cholest-5-ene-3β,16β,22S-triol = SMILES CC(C)CC{22}[C@H](O)[C@@H](C)[C@H]1{16}[C@@H](O)C[C@@]2([H])[C@]3([H])CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

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  Structure type: oligomer ; 749 [M+Na]+
  C39H66O12
  Trivial name: schubertoside B
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:31067, CBank-STR:3841
  
   
  
  Allium schubertii
  CSDB ID 119853 (all data & tools)
• Compound ID: 25742
  

  a-D-Glcp-(1-3)-+ | a-L-Rhap-(1-3)-a-D-Galp-(1-16)-Subst Subst = cholest-5-ene-3β,16β,22S-triol = SMILES CC(C)CC{22}[C@H](O)[C@@H](C)[C@H]1{16}[C@@H](O)C[C@@]2([H])[C@]3([H])CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

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  Structure type: oligomer ; 911 [M+Na]+
  C45H76O17
  Trivial name: schubertoside C
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:31068, CBank-STR:5777
  
   
  
  Allium schubertii
  CSDB ID 119854 (all data & tools)
• Compound ID: 25743
  

  a-L-Rhap-(1-1)-+ | a-L-Rhap-(1-3)-a-D-Galp-(1-16)-Subst Subst = cholest-5-ene-1β,3β,16β,22S-tetrol = SMILES CC(C)CC{22}[C@H](O)[C@@H](C)[C@H]1{16}[C@@H](O)C[C@@]2([H])[C@]3([H])CC=C4C{3}[C@@H](O)C{1}[C@@H](O)[C@]4(C)[C@@]3([H])CC[C@]12C

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  Structure type: oligomer ; 890 [M+2H]+
  C45H76O17
  Trivial name: schubertoside D
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:31069, CBank-STR:5277
  
   
  
  Allium schubertii
  CSDB ID 119855 (all data & tools)