Four new 3,4-seco-lupane-type triterpene glycosides (1−4) were isolated from the leaves of Acanthopanax senticosus forma inermis. The structures of 1−4 were established as 11α-hydroxy-3,4-seco-lup-4(23),20(30)-dien-3-oic acid methyl ester 28-oic acid 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside, designated as inermoside (1); 1-deoxychiisanoside (2); 24-hydroxychiisanoside (3); and 11-deoxyisochiisanoside (4) by 1H− 1H COSY and 1H−13C COSY(HMBC, HMQC) methods and FABMS.

glycosides, Acanthopanax senticosus f. inermis, seco-lupane-type triterpenes

NCBI PubMed ID: 11141103
Publication DOI: 10.1021/np000277c
Journal NLM ID: 7906882
Publisher: American Society of Pharmacognosy
Correspondence: Park S-Y <996p9052pharm.stud.kumamoto-u.ac.jp>
Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Kumamoto, Japan, College of Pharmacy, Kyung-Hee University, Seoul, South Korea, Korea Food and Drug Administration, Seoul, South Korea
Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, TLC, HPLC, extraction, evaporation, centrifugation, HR-EI-MS
 

• Compound ID: 32600
  

  a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst Subst = inermoside aglycon = SMILES O{28}C([C@]12CC[C@@H](C(C)=C)[C@@H]1[C@H]3C{11}[C@@H](O)[C@H]4[C@](CC[C@@H](C(C)=C)[C@@]4(CCC(OC)=O)C)(C)[C@]3(C)CC2)=O

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  Structure type: oligomer
  Trivial name: inermoside
  Compound class: glycoside
  
   
  
  Acanthopanax senticosus f. inermis
  CSDB ID 67304 (all data & tools)
• Compound ID: 32601
  

  a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst Subst = 1-deoxychiisanoside aglycon = SMILES O{28}C([C@]12CC[C@@H](C(C)=C)[C@@H]1[C@H]3C[C@@H]4[C@H]5[C@](CC[C@@H](C(C)=C)[C@]5(C)CCC(O4)=O)(C)[C@]3(C)CC2)=O

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  Structure type: oligomer
  Trivial name: 1-deoxychiisanoside
  Compound class: glycoside
  
   
  
  Acanthopanax senticosus f. inermis
  CSDB ID 67305 (all data & tools)
• Compound ID: 32602
  

  a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst Subst = 24-hydroxychiisanogenin = SMILES O{28}C([C@]12CC[C@@H](C(C)=C)[C@@H]1[C@H]3C[C@@H]4[C@H]5[C@](CC[C@@H](C({24}CO)=C)[C@]5(C){1}[C@H](O)CC(O4)=O)(C)[C@]3(C)CC2)=O

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  Structure type: oligomer
  Trivial name: 24-hydroxychiisanogenin
  Compound class: glycoside
  
   
  
  Acanthopanax senticosus f. inermis
  CSDB ID 67306 (all data & tools)
• Compound ID: 32603
  

  a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst Subst = 11-deoxyisochiisanoside aglycon = SMILES O{28}C([C@]12CC[C@@H](C(C)=C)[C@@H]1[C@H]3CC[C@H]4[C@](CC[C@@H]5[C@]4(C)[C@@H](C{3}C(O)=O)OC5(C)C)(C)[C@]3(C)CC2)=O

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  Structure type: oligomer
  Trivial name: 11-deoxyisochiisanoside
  Compound class: glycoside
  
   
  
  Acanthopanax senticosus f. inermis
  CSDB ID 67307 (all data & tools)