Show legend Show as text

Structure type: oligomer ; 1045 [M+Na]+
C₅₅H₇₄O₁₈
Trivial name: sarcovimiside B
Compound class: glycoside
Contained glycoepitopes: IEDB_139965

• Article ID: 10871
  Vleggaar R, van Heerden FR, Anderson LAP, Erasmus GL "Toxic constituents of the asclepiadaceae. Structure elucidation of sarcovimiside A-C, pregnane glycosides of Sarcostemma viminale" - Journal of the Chemical Society, Perkin Transactions 1 (1993) 483-487
  

  The structure elucidation of three related pregnane glycosides, sarcovimiside A, B, and C from Sarcostemma viminale, is based on a detailed study of their highfield 1H and 13C NMR spectra. The results show that all the sugars are (1→4)-linked and both (β-D- and α-L-cymarose residues are present in each glycoside chain. The aglycone of sarcovimiside A was identified as 12β-benzoyloxy-3β,8β,14.17-tetrahydroxy-14β,17α-pregn-5-en-20-one whereas in the case of both sarcovimiside B and C, oxidative cleavage of the C(8)–C(14) bond occurred and the aglycone is the 12,20-O,O-dibenzoyl derivative of (20S)-3β,5,12β,17,20-pentahydroxy-8,14-seco-5β,17α-pregn-6-ene-8,14-dione. Sarcovimiside C is the β-(1→4)-glucopyranosyl derivative of sarcovimiside B.

  Publication DOI: 10.1039/P19930000483
  Journal NLM ID: 7505598
  Publisher: Chemical Society
  Institutions: Department of Chemistry, University of Pretoria, Pretoria, South Africa, Department of Chemistry and Biochemistry, Rand Afrikaans University, Auckland Park, South Africa, Department of Toxicology, Onderstepoort, Veterinary Institute, Onderstepoort, South Africa
  Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, enzymatic digestion, PLC, CC
  
   
  
  Sarcostemma viminale
  CSDB ID 138562 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1207 [M+Na]+
C₆₁H₈₄O₂₃
Trivial name: sarcovimiside C
Compound class: glycoside
Contained glycoepitopes: IEDB_139965,IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 10871
  Vleggaar R, van Heerden FR, Anderson LAP, Erasmus GL "Toxic constituents of the asclepiadaceae. Structure elucidation of sarcovimiside A-C, pregnane glycosides of Sarcostemma viminale" - Journal of the Chemical Society, Perkin Transactions 1 (1993) 483-487
  

  The structure elucidation of three related pregnane glycosides, sarcovimiside A, B, and C from Sarcostemma viminale, is based on a detailed study of their highfield 1H and 13C NMR spectra. The results show that all the sugars are (1→4)-linked and both (β-D- and α-L-cymarose residues are present in each glycoside chain. The aglycone of sarcovimiside A was identified as 12β-benzoyloxy-3β,8β,14.17-tetrahydroxy-14β,17α-pregn-5-en-20-one whereas in the case of both sarcovimiside B and C, oxidative cleavage of the C(8)–C(14) bond occurred and the aglycone is the 12,20-O,O-dibenzoyl derivative of (20S)-3β,5,12β,17,20-pentahydroxy-8,14-seco-5β,17α-pregn-6-ene-8,14-dione. Sarcovimiside C is the β-(1→4)-glucopyranosyl derivative of sarcovimiside B.

  Publication DOI: 10.1039/P19930000483
  Journal NLM ID: 7505598
  Publisher: Chemical Society
  Institutions: Department of Chemistry, University of Pretoria, Pretoria, South Africa, Department of Chemistry and Biochemistry, Rand Afrikaans University, Auckland Park, South Africa, Department of Toxicology, Onderstepoort, Veterinary Institute, Onderstepoort, South Africa
  Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, enzymatic digestion, PLC, CC
  
   
  
  Sarcostemma viminale
  CSDB ID 138563 (all data & tools)