Show legend Show as text

Structure type: monomer
Trivial name: tetraphyllin A, deidaclin, linamarin
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11435
  Andersen L, Adsersen A, Jaroszewski JW "Cyanogenesis of Passiflora foetida" - Phytochemistry 47(6) (1998) 1049-1050
  

  Five cyanohydrin glycosides with a cyclopentene ring, tetraphyllin A, tetraphyllin B, tetraphyllin B sulphate, deidaclin and volkenin, were isolated from Passiflora foetida grown from seeds collected on the Galápagos Islands. By contrast, P. foetida collected on Réunion Island contained the valine-derived glycoside linamarin, along with the cyclopentanoids tetraphyllin B, volkenin and tetraphyllin B sulphate. The chemical differences between the two populations were accompanied by pronounced morphological differences. This is the first report of two populations of the same species, having different patterns of cyclopentanoid and valine-derived glycosides. Two populations of Passiflora foetida were found to have different pattern of cyclopentanoid and valine-derived glycosides, and to be morphologically different.

  linamarin, Passiflora foetida, Passifloraceae, chemical varieties, cyanohydrin glycosides, sulphate esters, tetraphyllin A and B, deidaclin, volkenin, Galapagos Islands, Reunion Island

  Publication DOI: 10.1016/S0031-9422(98)80070-8
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Medicinal Chemistry, Royal Danish School of Pharmacy, Copenhagen, Denmark
  Methods: 13C NMR, 1H NMR, HPLC, extraction, acetylation, desulfation
  
   
  
  Passiflora foetida
  CSDB ID 61738 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: deidaclin
Compound class: glycoside, cyanogenic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 12790
  Vetter J "Plant cyanogenic glycosides" - Toxicon 38(1) (2000) 11-36
  

  The cyanogenic glycosides belong to the products of secondary metabolism, to the natural products of plants. These compounds are composed of an alpha-hydroxynitrile type aglycone and of a sugar moiety (mostly D-glucose). The distribution of the cyanogenic glycosides (CGs) in the plant kingdom is relatively wide, the number of CG-containing taxa is at least 2500, and a lot of such taxa belong to families Fabaceae, Rosaceae, Linaceae, Compositae and others. Different methods of determination are discussed (including the indirect classical photometrical and the new direct chromatographic ones). The genetic control of cyanogenesis has no unique mechanism, the plants show variation in the amount of the produced HCN. The production of HCN depends on both the biosynthesis of CGs and on the existence (or absence) of its degrading enzymes. The biosynthetic precursors of the CGs are different L-amino acids, these are hydroxylated then the N-hydroxylamino acids are converted to aldoximes, these are turned into nitriles. The last ones are hydroxylated to alpha-hydroxynitriles and then they are glycosilated to CGs. The generation of HCN from CGs is a two step process involving a deglycosilation and a cleavage of the molecule (regulated by beta-glucosidase and alpha-hydroxynitrilase). The tissue level compartmentalisation of CGs and their hydrolysing enzymes prevents large-scale hydrolysis in intact plant tissue. The actual level of CGs is determined by various factors both developmental and ecological ones, which are reviewed too. The last part of the present work demonstrates the biological roles of CGs in plant physiological processes and in plant defence mechanisms as well. The effect of CGs (HCN) on different animals, the symptoms of poisonings are discussed to cows, sheep, donkeys, horses and chicks. Finally, the poisonous effects of cassava (Manihot esculenta) roots are summarised on experimental animals and on the human organism.

  cyanogenesis, plant cyanogenic glycosides, biosynthetic precursors

  NCBI PubMed ID: 10669009
  Publication DOI: 10.1016/s0041-0101(99)00128-2
  Journal NLM ID: 1307333
  Publisher: Pergamon Press for International Society On Toxinology
  Institutions: Department of Botany, University of Veterinary Sciences, Budapest, Hungary
  
   
  
  Deidamia
  CSDB ID 68354 (all data & tools)