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Nitroaromatic betulin derivatives as redox cycling agents
Author(s) -
Miškiniene Vanda,
Dičkancaite Egle,
Nemeikaite Aušra,
Čenas Narimantas
Publication year - 1997
Publication title -
iubmb life
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.132
H-Index - 113
eISSN - 1521-6551
pISSN - 1521-6543
DOI - 10.1080/15216549700202791
Subject(s) - betulin , chemistry , cytotoxicity , stereochemistry , oxidative stress , triterpenoid saponin , antioxidant , redox , biochemistry , organic chemistry , saponin , in vitro , medicine , alternative medicine , pathology
We have synthesized nitroaromatic derivatives of triterpenoid betulin (lup‐20(29)‐ene‐3β,28‐diol), betulin‐(28)‐5′‐(aziridin‐l‐yl)‐2′,4′‐dinitrobenzoate and betulin‐(28)‐5′‐nitro‐2′‐furoate. These compounds were reduced in single‐electron way by ferredoxin: NADP+ reductase and flavocytochrome b2 at rates comparable with their simple structure analogs. Besides, these compounds were substrates for DT‐diaphorase. Their toxicity to bovine leukemia virus‐transformed lamb fibroblast culture was partly prevented by antioxidant N,N′‐diphenyl‐p‐phenylene diamine and desferrioxamine, indicating an involvement of oxidative stress in their cytotoxicity.