DOUBLY ALLYLIC HYDROPEROXIDE FORMED IN THE REACTION BETWEEN STEROL 5,7‐DIENES AND SINGLET OXYGEN

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書誌事項

公開日
1994-10
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1111/j.1751-1097.1994.tb05109.x
公開者
Wiley

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説明

<jats:p><jats:bold>Abstract</jats:bold> Ergosterol and 7‐dehydrocholesterol, common 5,7‐conjugated diene sterols, react with photochemically produced singlet oxygen very efficiently to yield, in parallel pathways, the corresponding 5,8‐endoperoxides and the 7β‐hydroperoxy‐5,8(9),22‐trienol or ‐5, 8(9)‐dienol, respectively. The hydroperoxides decompose in an acid‐catalyzed reaction to generate hydrogen peroxide and the 5, 7, 9(1 1), 22‐tetraenol or 5, 7, 9(11) trienol, respectively, with 1:l stochiometry. The molar ratio of endoperoxide to hydroperoxide was constant (16:5) with two different reaction solvents, two different photosensitizers, and at all time points between 5 min and 3 h from the start of irradiation. Ergosterol did not react with either hydrogen peroxide or superoxide ion under our reaction conditions. Inhibition studies with nitrogen, 2,5‐dimethylfuran, βcarotene, and <jats:italic>tert</jats:italic>‐butanol confirmed the involvement of singlet oxygen in these reactions. The unstable hydroperoxide would be expected to have undesirable biological consequences if formed <jats:italic>in vivo</jats:italic>.</jats:p>

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