Three new cyclolanostanol xylosides were isolated from a batch of commercial Cimicifuga Rhizome, cimicifugoside H-1 (1), C_<35>H_<52>O_9,mp 260-262℃, [α]_D -43.5°, cimicifugoside H-2 (2), C_<35>H_<54>O_<10>, mp 227-229℃, [α]_D -38.8°, and cimicifugoside H-5 (3), C_<35>H_<52>O_<10>, mp 262-264℃, [α]_D -22.9°, together with known glycosides, actein and 27-deoxyactein. Their structures were determined on the basis of chemical and spectrometric evidence including an X-ray crystallographic analysis. The structure of cimicifugoside H-1 (1) was established as (20R, 24R)-24,25-epoxy-11β-hydroxy-3-β-(β-D-xylopyranosyloxy)-9,19-cyclolanost-7-ene-16,23-dione. Cimicifugoside H-5 (3) is the 15-hydroxylated derivative of 1. Since 1 changed into cimicifugoside H-2 (2) on treatment with p-toluenesulfonic acid, 2 has a 24R, 25-diol structure derived from 1 by opening its epoxy ring.

9, cimicifugoside H-1, cimicifugoside H-2, cimicifugoside H-5, Cimicifuga Rhizome, 19-cyclolanostanol, triterpenol glycoside

• Compound ID: 26801
  

  b-D-Xylp-(1-3)-Subst Subst = 20R,24R-24,25-epoxy-3β,11β-dihydroxy-9,19-cyclolanost-7-en-16,23-dione = SMILES C[C@@H]([C@H]1C(C[C@]2(C)[C@]1(C)C{11}[C@H](O)[C@]34C2=CC[C@@H]5[C@@]3(CC{3}[C@H](O)C5(C)C)C4)=O)CC([C@H]6C(C)(C)O6)=O

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  Structure type: monomer ; 639 [M+Na]+
  C35H52O9
  Trivial name: cimicifugoside H-1
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:42546, CBank-STR:870
  
   
  
  Cimicifuga simplex
  CSDB ID 120608 (all data & tools)
• Compound ID: 26802
  

  b-D-Xylp-(1-3)-Subst Subst = 20R,24R-3β,11β,24,25-tetrahydroxy-9,19-cyclolanost-7-en-16,23-dione = SMILES C[C@H](CC({24}[C@H](O){25}C(C)(C)O)=O)[C@H]1C(C[C@@]2([C@@]1(C{11}[C@@H]([C@]34C2=CC[C@@H]5[C@]3(C4)CC{3}[C@@H](C5(C)C)O)O)C)C)=O

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  Structure type: monomer ; 635 [M+H]+
  C35H55O10
  Trivial name: cimicifugoside H-2
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:42547, CBank-STR:875
  
   
  
  Cimicifuga simplex
  CSDB ID 120609 (all data & tools)
• Compound ID: 26803
  

  b-D-Xylp-(1-3)-Subst Subst = 20R,24R-24,25-epoxy-3β,11β,15-trihydroxy-9,19-cyclolanost-7-en-16,23-dione = SMILES C[C@H](CC([C@H](O1)C1(C)C)=O)[C@H]2C({15}C(O)[C@@]3([C@@]2(C{11}[C@@H]([C@]45C3=CC[C@@H]6[C@]4(C5)CC{3}[C@@H](C6(C)C)O)O)C)C)=O

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  Structure type: monomer ; 655 [M+Na]+
  C35H52O10
  Trivial name: cimicifugoside H-5
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:42548, CBank-STR:871
  
   
  
  Cimicifuga simplex
  CSDB ID 120610 (all data & tools)
• Compound ID: 26804
  

  b-D-Xylp-(1-3)-Subst12Ac Subst = acteol = SMILES C[C@@H]1C[C@]2(O[C@@H]3[C@H]1[C@@]4(C){12}[C@H](O)C[C@@]56C[C@@]57CC{3}[C@H](O)C(C)(C)[C@@H]7CC[C@H]6[C@]4(C)C3)[C@@H]8[C@@]({27}[C@@H](O)O2)(C)O8

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  Structure type: monomer
  Trivial name: actein
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:50569, CBank-STR:857
  
   
  
  Cimicifuga simplex
  CSDB ID 120611 (all data & tools)
• Compound ID: 26805
  

  b-D-Xylp-(1-3)-Subst12Ac Subst = 27-deoxyacetylacteol = SMILES C[C@@H]1C[C@]2(O[C@@H]3[C@H]1[C@@]4(C){12}[C@H](O)C[C@@]56C[C@@]57CC{3}[C@H](O)C(C)(C)[C@@H]7CC[C@H]6[C@]4(C)C3)[C@@H]8[C@@](CO2)(C)O8

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  Structure type: monomer
  Trivial name: 27-deoxyactein
  Compound class: saponin glycoside
  Reference(s) to other database(s): CCSD:50570, CBank-STR:866
  
   
  
  Cimicifuga simplex
  CSDB ID 120612 (all data & tools)