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酪氨酸酶催化4-烯丙基儿茶酚氧化过程中醌-醌甲基化物互变异构的直接证据。

Direct evidence for quinone-quinone methide tautomerism during tyrosinase catalyzed oxidation of 4-allylcatechol.

作者信息

Sugumaran M, Bolton J

机构信息

Department of Biology, University of Massachusetts at Boston 02125, USA.

出版信息

Biochem Biophys Res Commun. 1995 Aug 15;213(2):469-74. doi: 10.1006/bbrc.1995.2155.

DOI:10.1006/bbrc.1995.2155
PMID:7646501
Abstract

The hapatotoxicity of safrole and related compounds has been attributed to the electrophilic compounds generated from the oxidation of these chemicals. In this paper, for the first time using quasi pre-steady state conditions, we present direct evidence for the rapid production of electrophilic allyl o-quinone and its tautomerization to more stable and reactive vinyl p-quinone methide during both the enzyme catalyzed and chemical mediated oxidation of 4-allylcatechol, an in vivo product of safrole metabolism.

摘要

黄樟素及相关化合物的肝毒性归因于这些化学物质氧化产生的亲电化合物。在本文中,我们首次在准预稳态条件下,给出了亲电烯丙基邻醌快速生成及其在酶催化和化学介导的4-烯丙基儿茶酚(黄樟素代谢的体内产物)氧化过程中向更稳定且反应性更强的乙烯基对醌甲基化物互变异构的直接证据。

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Direct evidence for quinone-quinone methide tautomerism during tyrosinase catalyzed oxidation of 4-allylcatechol.酪氨酸酶催化4-烯丙基儿茶酚氧化过程中醌-醌甲基化物互变异构的直接证据。
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The reactivity of o-quinones which do not isomerize to quinone methides correlates with alkylcatechol-induced toxicity in human melanoma cells.不会异构化为醌甲基化物的邻醌的反应性与烷基儿茶酚在人黑色素瘤细胞中诱导的毒性相关。
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The influence of the p-alkyl substituent on the isomerization of o-quinones to p-quinone methides: potential bioactivation mechanism for catechols.对烷基取代基对邻醌异构化为对醌甲基化物的影响:儿茶酚潜在的生物活化机制。
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