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1991 (1)
1982 (1)
1Author    Bernd Sorg, Erich HeckerRequires cookie*
 Title    Zur Chemie des Ingenols, II [1] Ester des Ingenols und des A 18 -Isoingenols On the Chemistry of Ingenol, II [1] Esters of Ingenol and Zl 7 -8 -Isoingenol  
  Reference    Z. Naturforsch. 37b, 748—756 (1982); eingegangen am 3. Februar 1982 
  Published    1982 
  Keywords    Cocarcinogens, Ingenol, Initiation-Promoter, Irritants, Diterpene Esters 
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 TEI-XML for    default:Reihe_B/37/ZNB-1982-37b-0748.pdf 
 Identifier    ZNB-1982-37b-0748 
 Volume    37 
2Author    R. Bagavathi3, Bernd Sorg, Erich HeckerRequires cookie*
 Title    On the Chemistry of Ingenol, IV [1] Ingenol from Seeds of Euphorbia lathyris L. and Preparation of (9 R)[(9 S)]-9-Deoxo-9-hydroxyingenol with some Corresponding 3-and 9-Esters  
 Abstract    A simple and fast procedure was worked out to prepare from the commercially available seeds of Euphorbia lathyris L. substantial am ounts of the polyfunctional tetracyclic diterpene ingenol (la). Ingenol-3,4:5,20-diacetonide (ld) was treated with five different bases at two different tem peratures to achieve epimerization to 8-epiingenol. In any case unchanged 1 d was obtained. By reduction o f ingenol-3,4:5,20-diacetonide (ld) with sodium in ether/2-propanol (9 R)-9-deoxo-9-hydroxyingenol-3,4:5,20-diacetonide (2 b) was obtained and converted to the corresponding 5,20-monoacetonide 2 e. Reduction of ingenol-5,20-acetonide (le) with LiAlH4 in tetrahydrofuran furnished the epimeric (9S)-9-deoxo-9-hydroxyingenol-5,20-acetonide (3c).The (9 R)-m onoacetonide 2e was used to prepare the 3-tetradecanoate 2c o f (9R)-9-deoxo-9-hydroxyingenol (2a). From the (9S)-monoacetonide 3c four 3-esters [butyrate (3d), tetradecanoate (3e), eicosanoate (3f), benzoate (3g)] of (9S)-9-deoxo-9-hydroxyingenol (3a) were synthesized. The 3,4:5,20-diacetonides of 2a and 3a, i.e. 2b/3b were used to provide the 9-hexadecanoates 2 f and 3j. The irritant activities of the 3-esters o f the (9S)-series depend strongly on the nature o f the acyl group, thus furnishing, e.g. the moderately irritant tetra­ decanoate 3e [compared to corresponding 3-esters lb of ingenol (la)] as well as the highly ac­ tive benzoate 3 g o f 3 a. The (9 R)-3-tetradecanoate 2c exhibits com parable activity as its (9S)-analogue 3e. Thus, the spatial orientation (R or S) of the 9-hydroxy function plays a signifi­ cant but not a crucial role for irritant activity. Both epimeric (9 R)/(9S)-hexadecanoates 2f/3j were non-irritant. 
  Reference    Z. Naturforsch. 46b, 1425—1433 (1991); received February 15 1991 
  Published    1991 
  Keywords    Conditional Cancerogens, Tum or Promoters, Skin Irritants, Ingenol, Structure-Bioactivity Relationships 
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 TEI-XML for    default:Reihe_B/46/ZNB-1991-46b-1425.pdf 
 Identifier    ZNB-1991-46b-1425 
 Volume    46