In the course of our research on the oligoglycosidic constituents of Turkish Astragalus species, we have isolated a number of cycloartane-type triterpene glycosides. The current study examines the immunostimulatory effects of nineteen of these cycloartane-type compounds using a transcription-based bioassay for Nuclear Factor kappa B (NF-κB) activation in a human macrophage/monocyte cell line, THP-1. All compounds were inactive at 100 μg/ml except astragaloside I which increased NF-κB directed luciferase expression to levels about 65% as compared with maximal stimulation by E. coli lipopolysaccharide (LPS) at 10 μg/ml. None of the compounds were active at low dosage levels (0.1 μg/ml) in combination with 50 ng/ml LPS. Astragaloside I also increased mRNA expression of the inflammatory cytokines interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) as measured using reverse transcriptase-polymerase chain reaction (RT)-PCR. Based on these results it is clear that certain structural features are required for immunostimulation of cycloartane-type triterpene glycosides.

macrophage, immunostimulatory, THP-1, Astragalus, astragaloside I, nuclear factor kappa B (NF-κB)

• Compound ID: 31306
  

  b-D-Glcp-(1-22)-Subst Subst = macrophyllosaponins aglycon = SMILES O{3}[C@H]1C{1}[C@H](O)[C@]23C[C@]24CC[C@]5(C)C([C@@H](CC{21}[C@H](O){22}C(C)(O)C)C)CC[C@@]5(C)C4{7}[C@@H](O)CC3C1(C)C

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  Structure type: monomer
  Trivial name: macrophyllosaponin C
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus
  CSDB ID 64856 (all data & tools)
• Compound ID: 31307
  

  b-D-Xylp-(1-2)-b-D-Xylp-(1-3)-Subst Subst = macrophyllosaponins aglycon = SMILES O{3}[C@H]1C{1}[C@H](O)[C@]23C[C@]24CC[C@]5(C)C([C@@H](CC{21}[C@H](O){22}C(C)(O)C)C)CC[C@@]5(C)C4{7}[C@@H](O)CC3C1(C)C

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  Structure type: oligomer
  Trivial name: macrophyllosaponin D
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus
  CSDB ID 64857 (all data & tools)
• Compound ID: 28879
  

  b-D-Glcp-(1-6)-+ | b-D-Xylp-(1-3)-Subst Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  Trivial name: astragaloside IV, astragalus saponin AS I, cycloastragenol
  Compound class: saponin glycoside, glycoside, triterpenoid glycoside
  
   
  
  Astragalus microcephalus, Astragalus melanophrurius
  CSDB ID 64866 (all data & tools)
• Compound ID: 30252
  

  b-D-Glcp-(1-6)-Subst Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: monomer
  Trivial name: brachyoside B
  Compound class: saponin glycoside, glycoside, triterpenoid glycoside
  
   
  
  Astragalus microcephalus
  CSDB ID 64871 (all data & tools)
• Compound ID: 31310
  

  b-D-Glcp-(1-6)-+ | b-D-Xylp-(1-3)-Subst Subst = cyclocanthogenin = SMILES C[C@H](CC{24}[C@H](O){25}C(C)(C)O)[C@H]1{16}[C@@H](O)C[C@@]2(C)[C@@H]3C{6}[C@H](O)[C@H]4C(C)(C){3}[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C

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  Structure type: oligomer
  Trivial name: cyclocanthoside E
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus microcephalus
  CSDB ID 64860 (all data & tools)
• Compound ID: 31316
  

  b-D-Glcp-(1-6)-+ | b-D-Xylp-(1-3)-Subst Subst = 20,25-epoxy-3β,6α-dihydroxycycloartane-16β,24α-diol = SMILES C[C@@]6(C)O[C@@](C)([C@H]4{16}[C@@H](O)C[C@@]5(C)C2C{6}[C@H](O)C1[C@@](C)(C){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C)CC{24}[C@@H]6O

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  Structure type: oligomer
  Trivial name: cyclocephaloside I
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus microcephalus
  CSDB ID 64872 (all data & tools)
• Compound ID: 27852
  

  b-D-Glcp-(1-6)-+ | b-D-Xylp2Ac3Ac-(1-3)-Subst Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  C41H68O14
  Trivial name: astragaloside I, astragaloside I (astrasieversianin IV)
  Compound class: saponin glycoside, glycoside, triterpenoid glycoside
  
   
  
  Astragalus trojanus, Astragalus melanophrurius
  CSDB ID 64864 (all data & tools)
• Compound ID: 27853
  

  b-D-Xylp-(1-6)-+ | b-D-Xylp2Ac3Ac-(1-3)-Subst Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  C41H68O14
  Trivial name: astrasieversianin II
  Compound class: saponin glycoside, glycoside, triterpenoid glycoside
  
   
  
  Astragalus trojanus, Astragalus melanophrurius
  CSDB ID 64862 (all data & tools)
• Compound ID: 28886
  

  b-D-Glcp-(1-6)-+ | b-D-Xylp2Ac-(1-3)-Subst Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  Trivial name: astragaloside II
  Compound class: saponin glycoside, glycoside, triterpenoid glycoside
  
   
  
  Astragalus trojanus, Astragalus melanophrurius
  CSDB ID 64865 (all data & tools)
• Compound ID: 30251
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-25)-Subst | b-D-Glcp-(1-6)-+ Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  Trivial name: astragaloside VII
  Compound class: saponin glycoside, glycoside, triterpenoid glycoside
  
   
  
  Astragalus trojanus, Astragalus melanophrurius
  CSDB ID 64868 (all data & tools)
• Compound ID: 31314
  

  b-D-Glcp-(1-6)-+ | b-D-Xylp-(1-3)-Subst16Ac Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  Trivial name: trojanoside A
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus trojanus
  CSDB ID 64869 (all data & tools)
• Compound ID: 31315
  

  b-D-Glcp-(1-6)-+ | a-L-Arap-(1-2)-b-D-Xylp-(1-3)-Subst Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  Trivial name: trojanoside H
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus trojanus
  CSDB ID 64870 (all data & tools)
• Compound ID: 31305
  

  b-D-Xylp-(1-3)-Subst Subst = macrophyllosaponins aglycon = SMILES O{3}[C@H]1C{1}[C@H](O)[C@]23C[C@]24CC[C@]5(C)C([C@@H](CC{21}[C@H](O){22}C(C)(O)C)C)CC[C@@]5(C)C4{7}[C@@H](O)CC3C1(C)C

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  Structure type: monomer
  Trivial name: macrophyllosaponin B
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus oleifolius
  CSDB ID 64855 (all data & tools)
• Compound ID: 31308
  

  b-D-Glcp-(1-16)-+ | a-L-Arap-(1-2)-b-D-Xylp-(1-3)-Subst Subst = cyclocanthogenin = SMILES C[C@H](CC{24}[C@H](O){25}C(C)(C)O)[C@H]1{16}[C@@H](O)C[C@@]2(C)[C@@H]3C{6}[C@H](O)[C@H]4C(C)(C){3}[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C

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  Structure type: oligomer
  Trivial name: askendoside G
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus prusianus
  CSDB ID 64858 (all data & tools)
• Compound ID: 31309
  

  b-D-Xylp-(1-3)-+ | b-D-Glcp-(1-16)-Subst Subst = cyclocanthogenin = SMILES C[C@H](CC{24}[C@H](O){25}C(C)(C)O)[C@H]1{16}[C@@H](O)C[C@@]2(C)[C@@H]3C{6}[C@H](O)[C@H]4C(C)(C){3}[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C

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  Structure type: oligomer
  Trivial name: cyclocanthoside D
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus cephalotes
  CSDB ID 64859 (all data & tools)
• Compound ID: 31311
  

  b-D-Glcp-(1-16)-+ | b-D-Xylp-(1-24)-Subst | b-D-Xylp-(1-3)-+ Subst = cyclocanthogenin = SMILES C[C@H](CC{24}[C@H](O){25}C(C)(C)O)[C@H]1{16}[C@@H](O)C[C@@]2(C)[C@@H]3C{6}[C@H](O)[C@H]4C(C)(C){3}[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C

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  Structure type: oligomer
  Trivial name: cephalatoside A
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus cephalotes
  CSDB ID 64861 (all data & tools)
• Compound ID: 31312
  

  b-D-Xylp-(1-6)-+ | b-D-Xylp-(1-3)-Subst Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  Trivial name: astrasieversianin X
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus melanophrurius
  CSDB ID 64863 (all data & tools)
• Compound ID: 31313
  

  b-D-Glcp-(1-6)-+ | b-D-Glcp-(1-2)-b-D-Xylp-(1-3)-Subst Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H]

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  Structure type: oligomer
  Trivial name: astragaloside VI
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus melanophrurius
  CSDB ID 64867 (all data & tools)

Macrophyllosaponin E, a novel cycloartane-type triterpene, has been isolated from the roots of Astragalus oleifolius. The structure elucidation of the compound was achieved by a combination of one- and two-dimensional NMR techniques [1H-1H-correlation spectroscopy (COSY), 1H-13C-heteronuclear multiple guantum correlation spectroscopy (HMQC), and 1H-13C-heteronuclear multiple-bond correlation spectroscopy (HMBC)l and high resolution electrospray ionization Fourier transformation mass spectrometry (HR-ESI-FT-MS).

Leguminosae, cycloartane-type triterpene, Astragalus oleifolius, macrophyllosaponin E

• Compound ID: 31325
  

  b-D-Glcp-(1-3)-+ | b-D-Glcp-(1-22)-Subst Subst = macrophyllosaponins aglycon = SMILES O{3}[C@H]1C{1}[C@H](O)[C@]23C[C@]24CC[C@]5(C)C([C@@H](CC{21}[C@H](O){22}C(C)(O)C)C)CC[C@@]5(C)C4{7}[C@@H](O)CC3C1(C)C

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  Structure type: oligomer ; 839.4721 [M+Na]+
  C42H75O15
  Trivial name: macrophyllosaponin E
  Compound class: glycoside, triterpenoid glycoside
  
   
  
  Astragalus oleifolius
  CSDB ID 64882 (all data & tools)