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Structure type: monomer ; 657.3652 [M+Na]+
C₃₅H₅₄O₁₀
Trivial name: tumacoside A
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11393
  Saez J, Cardona W, Espinal D, Blair S, Mesa J, Bocar M, Jossang A "Five new steroids from Solanum nudum" - Tetrahedron 54(36) (1998) 10771-10778
  

  Five new steroids, the cholest-4-ene-3,22-diones : tumacone A (1), tumacone B (2), tumacoside A (3), tumacoside B (4), and a furostenone: tumaquenone (5), besides diosgenone (6), were isolated from the aerial parts of Solanum nudum. Their structures were determined by 2D NMR, MS analyses and chemical correlations. Steroid 3 and 5 displayed in vitro antimalarial activity against a Plasmodium falciparum chloroquine-resistant FCB-1 strain (IC50 27 and 16 mu M). The observed stereodependent cyclization into spiroketals of two 16-O isomers is discussed.

  antimalarial, steroids, Solanum nudum, cholest-4-en-3, 22-dione, tumacones A and B, tumacosides A and B, tumaquenone, stereodependent cyclization

  Publication DOI: 10.1016/S0040-4020(98)00632-2
  Journal NLM ID: 2984170R
  Publisher: Pergamon Press
  Institutions: Laboratoire de Chimie, URA 401 CNRS, Muséum National d'Histoire Naturelle, Paris, France, Department of Chemistry, Faculty of Sciences, University of Antioquia, Medellin, Colombia, Department of Parasitology, Faculty of Medicine, University of Antioquia, Medellin, Colombia
  Methods: 13C NMR, 1H NMR, EI-MS, IR, optical rotation measurement, acetylation, CC, HMBC, DEPT, NOESY, HR-FAB-MS, extraciton, HETCOR
  
   
  
  Solanum nudum
  CSDB ID 61588 (all data & tools)

Show legend Show as text

Structure type: monomer ; 615.3467 [M+Na]+
C₃₃H₅₂O₉
Trivial name: tumacoside B
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11393
  Saez J, Cardona W, Espinal D, Blair S, Mesa J, Bocar M, Jossang A "Five new steroids from Solanum nudum" - Tetrahedron 54(36) (1998) 10771-10778
  

  Five new steroids, the cholest-4-ene-3,22-diones : tumacone A (1), tumacone B (2), tumacoside A (3), tumacoside B (4), and a furostenone: tumaquenone (5), besides diosgenone (6), were isolated from the aerial parts of Solanum nudum. Their structures were determined by 2D NMR, MS analyses and chemical correlations. Steroid 3 and 5 displayed in vitro antimalarial activity against a Plasmodium falciparum chloroquine-resistant FCB-1 strain (IC50 27 and 16 mu M). The observed stereodependent cyclization into spiroketals of two 16-O isomers is discussed.

  antimalarial, steroids, Solanum nudum, cholest-4-en-3, 22-dione, tumacones A and B, tumacosides A and B, tumaquenone, stereodependent cyclization

  Publication DOI: 10.1016/S0040-4020(98)00632-2
  Journal NLM ID: 2984170R
  Publisher: Pergamon Press
  Institutions: Laboratoire de Chimie, URA 401 CNRS, Muséum National d'Histoire Naturelle, Paris, France, Department of Chemistry, Faculty of Sciences, University of Antioquia, Medellin, Colombia, Department of Parasitology, Faculty of Medicine, University of Antioquia, Medellin, Colombia
  Methods: 13C NMR, 1H NMR, EI-MS, IR, optical rotation measurement, acetylation, CC, HMBC, DEPT, NOESY, HR-FAB-MS, extraciton, HETCOR
  
   
  
  Solanum nudum
  CSDB ID 61589 (all data & tools)