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Further studies of a new vitamin E analogue more active than α‐tocopherol in the rat curative myopathy bioassay
Author(s) -
Ingold K.U.,
Burton G.W.,
Foster D.O.,
Hughes L.
Publication year - 1990
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(90)80288-t
Subject(s) - bioassay , chemistry , vitamin e , tocopherol , stereochemistry , vitamin , myopathy , biochemistry , antioxidant , medicine , biology , genetics
The bioactivities of the acetates of 2 R ,4' R ,8' R ‐ and 25,4' R ,8' R ‐2,4,6,7‐tetramethyl‐2‐(4',8',12'‐trimethyltridecyl)‐5‐hydroxy‐3,4‐dihydrobenzofuran ( RRR ‐ and SRR ‐1‐Ac) have been measured in the rat curative myopathy bioassay and compared with the RRR and SRR stereoisomers of α‐tocopheryl acetate ( RRR ‐ and SRR ‐2‐Ac). Each stereoisomer of 1 is only slightly more active than the corresponding stereoisomer of 2( RRR ‐1‐Ac/ RRR ‐2‐Ac = 110; SRR ‐1‐Ac/ SRR ‐2‐Ac = 1.16). This finding contrasts with our earlier finding [(1986) FEBS Lett. 205, 117 120], confirmed in the present study, that all‐rac ‐1‐Ac is 1.5‐1.9 as active as all ‐ rac ‐2‐ Ac . We suggest that the stereochemistry ( S vs R ) at the 4' and 8' tail carbons is of less biological importance in 1 than in 2.