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Structure type: oligomer ; 1409 [M-H]-
C₆₅H₁₀₂O₃₃
Trivial name: vaccaroside F
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_136044,IEDB_136105,IEDB_136907,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142489,IEDB_149135,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_86,SB_88

• Article ID: 11547
  Jia Z, Koike K, Kudo M, Li H, Nikaido T "Triterpenoid saponins and sapogenins from Vaccaria segetalis" - Phytochemistry 48(3) (1998) 529-536
  

  Four new triterpenoid saponins, vaccarosides E, F, G and H were isolated from the seeds of Vaccaria segetalis and were respectively defined to be 3- O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl] quillaic acid 28- O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L- arabinofuranosyl-(1 → 3)]-β-D-4-O-acetylfucopyranoside; 3-O-[β-D- galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl] 3β,4α,16α-trihydroxy- 23-norolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L- rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-4-O- acetylfucopyranoside; 3-O-[β-D-galactopyranosyl-(1 → 2)-β-D- glucuronopyranosyl] gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L- rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-4-O- acetylfucopyranoside; and 3-O-[β-D-galactopyranosyl-(1 → 2)-β-D- glucuronopyranosyl] 3β,4α-dihydroxy-23-norolean-12-en-28-oic acid 28-O-β- D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L- arabinofuranosyl-(1 → 3)]-β-D-4-O-acetylfucopyranoside. Their structures were established on the basis of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC AND NOESY), FAB-MS and ESI-MS studies as well as chemical strategies and enzymatic degradation. The new aglycones of two of the saponins have been designated as segetalic acid and vaccaric acid, respectively.

  triterpene, quillaic acid, triterpenoid saponin, seeds, gypsogenin, F, Caryophyllaceae, Vaccaria segetalis, nortriterpene, segetalic acid, vaccaric acid, vaccarosides E, G and H

  NCBI PubMed ID: 9654779
  Publication DOI: 10.1016/S0031-9422(97)01128-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Pharmacognosy, School of Pharmaceutical Sciences, Funabashi, Chiba, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, enzymatic hydrolysis, ESI-MS, acid hydrolysis, GLC, HPLC, alkaline hydrolysis, extraction, optical rotation measurement, melting point determination, HMBC, DEPT, COSY, NOESY, MPLC, HOHAHA, HETCOR
  
   
  
  Vaccaria segetalis
  CSDB ID 63571 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 835 [M+Na]+
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_190606,IEDB_423153,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 11547
  Jia Z, Koike K, Kudo M, Li H, Nikaido T "Triterpenoid saponins and sapogenins from Vaccaria segetalis" - Phytochemistry 48(3) (1998) 529-536
  

  Four new triterpenoid saponins, vaccarosides E, F, G and H were isolated from the seeds of Vaccaria segetalis and were respectively defined to be 3- O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl] quillaic acid 28- O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L- arabinofuranosyl-(1 → 3)]-β-D-4-O-acetylfucopyranoside; 3-O-[β-D- galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl] 3β,4α,16α-trihydroxy- 23-norolean-12-en-28-oic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L- rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-4-O- acetylfucopyranoside; 3-O-[β-D-galactopyranosyl-(1 → 2)-β-D- glucuronopyranosyl] gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L- rhamnopyranosyl-(1 → 2)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-4-O- acetylfucopyranoside; and 3-O-[β-D-galactopyranosyl-(1 → 2)-β-D- glucuronopyranosyl] 3β,4α-dihydroxy-23-norolean-12-en-28-oic acid 28-O-β- D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L- arabinofuranosyl-(1 → 3)]-β-D-4-O-acetylfucopyranoside. Their structures were established on the basis of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC AND NOESY), FAB-MS and ESI-MS studies as well as chemical strategies and enzymatic degradation. The new aglycones of two of the saponins have been designated as segetalic acid and vaccaric acid, respectively.

  triterpene, quillaic acid, triterpenoid saponin, seeds, gypsogenin, F, Caryophyllaceae, Vaccaria segetalis, nortriterpene, segetalic acid, vaccaric acid, vaccarosides E, G and H

  NCBI PubMed ID: 9654779
  Publication DOI: 10.1016/S0031-9422(97)01128-X
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Pharmacognosy, School of Pharmaceutical Sciences, Funabashi, Chiba, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, enzymatic hydrolysis, ESI-MS, acid hydrolysis, GLC, HPLC, alkaline hydrolysis, extraction, optical rotation measurement, melting point determination, HMBC, DEPT, COSY, NOESY, MPLC, HOHAHA, HETCOR
  
   
  
  Vaccaria segetalis
  CSDB ID 63575 (all data & tools)