Four new oleanane-type triterpene glycosides, proceraosides A-D (1-4), were isolated from the seeds of Albizia procera. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and a monoterpenic carboxylic acid linked to a monoterpene quinovoside as the acyl moiety at C-21. The common oligosaccharide moiety linked to C-28 in 1-3 was determined as α-L- arabinofuranosyl(l→4)-[β-D-glucopyranosyl-(l→3)]-α-L-rhamnopyranosyl- (l→2)-β-D-glucopyranosyl ester. These compounds differed in the C-3-linked sugar unit or in the configuration of C-6' of the inner monoterpene moiety in the C-21-linked acyl unit. Compound 4 was established as the 16-deoxy analogue of 1.

saponins, medicinal plants, magnetic resonanse spectroscopy, Albizia procera

• Compound ID: 29697
  

  S-Menthiafolic-(1-4)-b-D-Quip-(1-6)-Subst-(1-21)-+ | a-L-Araf-(1-4)-+ | | | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1 | b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ Subst = 2,3-dihydro-S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CCCC(C){1}C(=O)O; Subst1 = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5

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  Structure type: oligomer ; 2034 [M+Na]+
  C96H154O44
  Trivial name: proceraoside A
  Compound class: triterpenoid glycoside
  
   
  
  Albizia procera
  CSDB ID 63427 (all data & tools)
• Compound ID: 29698
  

  b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-Subst Subst = acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@](O6)([H])C[C@@](C6=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H]

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  Structure type: oligomer
  Trivial name: julibroside A2
  Compound class: triterpenoid glycoside
  
   
  
  Albizia procera
  CSDB ID 63437 (all data & tools)
• Compound ID: 29699
  

  b-D-Xylp-(1-2)-a-L-Arap-(1-6)-b-D-Glcp-(1-3)-Subst Subst = acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@](O6)([H])C[C@@](C6=O)5{16}[C@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H]

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  Structure type: oligomer
  Trivial name: albiziasaponin A
  Compound class: triterpenoid glycoside
  
   
  
  Albizia procera
  CSDB ID 63658 (all data & tools)
• Compound ID: 29700
  

  b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-Subst Subst = machaerinic acid = SMILES O{3}[C@H]1CC[C@@]2([C@]3(CC=C4[C@@]5(CC({21}[C@@H](O)C[C@@]5(CC[C@]4([C@@]3(CC[C@@]2([H])C1(C)C)C)C){28}C(O)=O)(C)C)[H])[H])C

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  Structure type: oligomer ; 911 [M-H]-
  C47H76O17
  Compound class: triterpenoid glycoside
  
   
  
  Albizia procera
  CSDB ID 63659 (all data & tools)
• Compound ID: 29701
  

  b-D-Quip-(1-6)-Subst Subst = 2,3-dihydro-R/S-menthiafolic acid = SMILES C=C{6}C(C)(O)CCCC(C){1}C(=O)O

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  Structure type: monomer ; 331 [M-H]-
  
   
  
  Albizia procera
  CSDB ID 63660 (all data & tools)
• Compound ID: 29702
  

  S-Menthiafolic-(1-4)-b-D-Quip-(1-6)-Subst-(1-21)-+ | a-L-Araf-(1-4)-+ | | | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1 | b-D-Xylp-(1-2)-a-L-Arap-(1-6)-b-D-Glcp-(1-3)-+ Subst = 2,3-dihydro-S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CCCC(C){1}C(=O)O; Subst1 = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5

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  Structure type: oligomer ; 2020 [M+Na]+
  C95H154O44
  Trivial name: proceraoside B
  Compound class: triterpenoid glycoside
  
   
  
  Albizia procera
  CSDB ID 63661 (all data & tools)
• Compound ID: 29703
  

  S-Menthiafolic-(1-4)-b-D-Quip-(1-6)-Subst-(1-21)-+ | a-L-Araf-(1-4)-+ | | | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1 | b-D-Xylp-(1-2)-a-L-Arap-(1-6)-b-D-Glcp-(1-3)-+ Subst = 2,3-dihydro-R-menthiafolic acid = SMILES C=C{6}[C@](C)(O)CCCC(C){1}C(=O)O; Subst1 = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5

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  Structure type: oligomer ; 2020 [M+Na]+
  C95H152O44
  Trivial name: proceraoside C
  Compound class: triterpenoid glycoside
  
   
  
  Albizia procera
  CSDB ID 63662 (all data & tools)
• Compound ID: 29704
  

  S-Menthiafolic-(1-4)-b-D-Quip-(1-6)-Subst-(1-21)-+ | a-L-Araf-(1-4)-+ | | | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1 | b-D-Xylp-(1-2)-b-D-Fucp-(1-6)-b-D-Glcp-(1-3)-+ Subst = 2,3-dihydro-S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CCCC(C){1}C(=O)O; Subst1 = machaerinic acid = SMILES O{3}[C@H]1CC[C@@]2([C@]3(CC=C4[C@@]5(CC({21}[C@@H](O)C[C@@]5(CC[C@]4([C@@]3(CC[C@@]2([H])C1(C)C)C)C){28}C(O)=O)(C)C)[H])[H])C

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  Structure type: oligomer ; 2018 [M+Na]+
  C96H154O43
  Trivial name: proceraoside D
  Compound class: triterpenoid glycoside
  
   
  
  Albizia procera
  CSDB ID 63663 (all data & tools)