Further studies of a new vitamin E analogue more active than alpha-tocopherol in the rat curative myopathy bioassay.
The bioactivities of the acetates of 2R,4'R,8'R- and 2S,4'R,8'R-2,4,6,7-tetramethyl-2-(4',8',12'-trimethyltridecyl)-5-h ydroxy-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 alpha-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 = 1.10; 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.
Ingold
K U
KU
Division of Chemistry, National Research Council of Canada, Ottawa, Ont.
Burton
G W
GW
Foster
D O
DO
Hughes
L
L
D000818:Animals; D001681:Biological Assay; D055598:Chemical Phenomena; D002621:Chemistry; D008297:Male; D011770:Pyruvate Kinase / Q000097:blood; D051381:Rats; D011919:Rats, Inbred Strains; D013237:Stereoisomerism; D014810:Vitamin E / Q000031:analogs & derivatives* / Q000494:pharmacology; D014811:Vitamin E Deficiency / Q000097:blood
D014810:Vitamin E; D011770:Pyruvate Kinase