ChemInform Abstract: Allergenic α-Methylene-γ-butyrolactones. Study of the Capacity of β-Acetoxy- and β-Hydroxy-α-methylene-γ-butyrolactones to Induce Allergic Contact Dermatitis in Guinea Pigs.

1986 ◽  
Vol 17 (38) ◽  
Author(s):  
P. BARBIER ◽  
C. BENEZRA
Ensho ◽  
1993 ◽  
Vol 13 (6) ◽  
pp. 571-574
Author(s):  
Yoko Shoji ◽  
Tadashi Fukumura ◽  
Toshitaka Kudo ◽  
Akira Yanagawa ◽  
Jingoro Shimada ◽  
...  

1993 ◽  
Vol 48 (3) ◽  
pp. 387-393 ◽  
Author(s):  
Wilfried A. König. ◽  
Holger Faasch ◽  
Holger Heitsch ◽  
Cornelia Colberg ◽  
Björn M. Hausen

Benzoquinones such as primin (2-methoxy-6-pentyl-1,4-benzoquinone) from Primula obconica HANCE (Primulaceae) are known to be strong sensitizers and thus the source of severe allergic contact dermatitis (cell-mediated type of allergy). In order to determine the relationship between sensitizing capacity and chemical structure the synthesis of 19 side-chain-modified analogues of primin was carried out. With each of these primin derivatives 10 guinea pigs were sensitized using a modified FCA-method (FCA = Freund’s complete adjuvant). Elicitation was done open epicutaneously with 0.001 molar concentrations. In these sensitization experiments 2-methoxy-6-alkyl-1,4-benzoquinones (chain length C1-C15) showed ascending sensitizing potency with increasing number of the side chain carbon atoms reaching maximum activity at an alkyl chain of 10 to 11 carbons. Beyond this point a decrease of the sensitizing potency in correlation with a further prolongation of the side chain was observed.


1978 ◽  
Vol 56 (3) ◽  
pp. 153-157 ◽  
Author(s):  
Gilbert Schlewer ◽  
Jean-Luc Stampf ◽  
Claude Benezra

Three new lactones, 2-oxo-3-methylene-4,7-methanobenzofuran and two α-methylene spirolactones, 3′,3′-dimethylspiro(2-oxo-3-methylenefuran-5,2′-norbornane), were synthesized and their skin activity was tested on one human volunteer and on guinea pigs. The man, sensitized to Frullania, was found sensitive to the above lactones and also reacted to frullanolide and alantolactone. The guinea pigs, experimentally sensitized to alantolactone, cross-reacted to 2-oxo-3-methylene-4,7-methanobenzofuran and the two α-methylene spirolactones, and also to isolantolactone and frullanolide.


1989 ◽  
Vol 20 (1) ◽  
pp. 10-16 ◽  
Author(s):  
Catherine A. Biren ◽  
Ronald J. Barr ◽  
Grace S. Ganderup ◽  
Lucille L. Emus ◽  
Jerry L. McCullough

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