A series of new ester saponins, elliptosides A-J, has been isolated from the tropical plant Archidendron ellipticum (Leguminosae). These saponins were particularly cytotoxic to certain renal and melanoma cancer cell lines in the NCI's 60-cell line human tumor screen. The structures of elliptosides A, E, and F were elucidated by spectroscopic and chemical means. Elliptoside A showed in vivo antitumor activity against the LOX melanoma cell line.

NCBI PubMed ID: 9313857
Publication DOI: 10.1016/S0968-0896(97)00098-9
Journal NLM ID: 9413298
Publisher: Elsevier
Correspondence: mb93jnih.gov
Institutions: Laboratory of Drug Discovery Research & Development, National Cancer Institute, Frederick, MD, USA 21702-1201, USA
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, GC-MS, sugar analysis, biological assays, NMR-1D, HPLC, peracetylation
 

• Compound ID: 27717
  

  Xylp-(1-2)-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 ; 951 [M+Na]+
  C47H77O18
  Trivial name: prosaponin, julibroside A3
  Compound class: saponin glycoside
  
   
  
  Archidendron ellipticum
  CSDB ID 60140 (all data & tools)
• Compound ID: 27718
  

  Xylp-(1-2)-Fucp-(1-6)-b-D-GlcpNAc-(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 ; 992 [M+Na]+
  C49H80NO18
  Trivial name: prosaponin, julibroside A3
  Compound class: saponin glycoside
  
   
  
  Archidendron ellipticum
  CSDB ID 60141 (all data & tools)
• Compound ID: 27719
  

  a-L-Araf-(1-4)-+ | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-1)-Allyl

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  Structure type: oligomer
  C26H45O19
  Compound class: saponin glycoside
  
   
  
  Archidendron ellipticum
  CSDB ID 60142 (all data & tools)
• Compound ID: 27720
  

  a-L-Quip-(1-6)-+ | Xylp-(1-2)-Fucp-(1-6)-b-D-GlcpNAc-(1-3)-+ | | | a-L-Araf-(1-4)-+ | | | | | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-Menthiafolic 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
  C88H141ONO43Cs
  Trivial name: monodesmonoterpenyl elliptoside A
  Compound class: saponin glycoside
  
   
  
  Archidendron ellipticum
  CSDB ID 60143 (all data & tools)
• Compound ID: 27721
  

  Menthiafolic-(1-4)-a-L-Quip-(1-6)-+ | Xylp-(1-2)-Fucp-(1-6)-b-D-GlcpNAc-(1-3)-+ | | | a-L-Araf-(1-4)-+ | | | | | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-Menthiafolic 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 ; 2089 [M+Na]+
  C98H155ONO45Cs
  Trivial name: elliptoside A
  Compound class: saponin glycoside
  
   
  
  Archidendron ellipticum
  CSDB ID 60144 (all data & tools)
• Compound ID: 27722
  

  Subst2-(1-4)-a-L-Quip-(1-6)-+ | Xylp-(1-2)-Fucp-(1-6)-b-D-GlcpNAc-(1-3)-+ | | | a-L-Araf-(1-4)-+ | | | | | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-Menthiafolic 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; Subst2 = (E)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid = SMILES C=CC(C)(O)CC/C=C(CO)/{1}C(O)=O

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  Structure type: oligomer ; 2105 [M+Na]+
  C98H155ONO46Cs
  Trivial name: elliptoside E
  Compound class: saponin glycoside
  
   
  
  Archidendron ellipticum
  CSDB ID 60145 (all data & tools)
• Compound ID: 27723
  

  Subst2-(1-4)-a-L-Quip-(1-6)-+ | Xylp-(1-2)-Fucp-(1-6)-b-D-Glcp-(1-3)-+ | | | a-L-Araf-(1-4)-+ | | | | | b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-Subst1-(21-1)-Menthiafolic 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; Subst2 = (E)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoic acid = SMILES C=CC(C)(O)CC/C=C(CO)/{1}C(O)=O

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  Structure type: oligomer
  C96H152OO46Cs
  Trivial name: elliptoside F
  Compound class: saponin glycoside
  
   
  
  Archidendron ellipticum
  CSDB ID 60146 (all data & tools)