A three-enzyme-system to degrade curcumin to natural vanillin.
A three-enzyme-system to degrade curcumin to natural vanillin.
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DOI：
10.3390/molecules20046640
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发表时间：
2015-04-14
期刊：
影响因子：
--
通讯作者：
Berger RG
中科院分区：
文献类型：
--
作者：
Esparan V;Krings U;Struch M;Berger RG
姜黄素的对称结构包括两个4-羟基-3-甲氧基苯亚基。漆酶催化苯酚自由基的形成、自由基的迁移和苯基位上的氧插入可导致香兰素的形成。由于香兰素本身是漆酶的首选酚类底物，一旦香兰素被释放，香兰素低聚物和聚合物的形成是不可避免的。为了减缓齐聚反应，通过乙酰化保护了其中一个酚羟基。以南极假丝酵母脂肪酶(CAL)为底物，主要乙酰化产物为单乙酰姜黄素，摩尔产率约为49%。在第二步中，将单乙酰姜黄素与各种担子菌的漆酶在两相体系(乙醚/水缓冲液)中孵育。黄腐菌漆酶(LccFtr)具有较高的转化率(姜黄素单乙酸酯的摩尔转化率为46%)，可转化为香草醛。无保护的香兰素部分与较高分子产物的混合物反应。在第三步中，使用杏鲍菇的阿魏酸酯酶(PeFaeA)从香草醛醋酸酯中去除保护基团(摩尔产率为68%)。氨基酸序列的比对表明，高势漆酶在该介体和无辅因子反应中表现得更好。
The symmetrical structure of curcumin includes two 4-hydroxy-3-methoxyphenyl substructures. Laccase catalyzed formation of a phenol radical, radical migration and oxygen insertion at the benzylic positions can result in the formation of vanillin. As vanillin itself is a preferred phenolic substrate of laccases, the formation of vanillin oligomers and polymers is inevitable, once vanillin becomes liberated. To decelerate the oligomerization, one of the phenolic hydroxyl groups was protected via acetylation. Monoacetyl curcumin with an approximate molar yield of 49% was the major acetylation product, when a lipase from Candida antarctica (CAL) was used. In the second step, monoacetyl curcumin was incubated with purified laccases of various basidiomycete fungi in a biphasic system (diethyl ether/aqueous buffer). A laccase from Funalia trogii (LccFtr) resulted in a high conversion (46% molar yield of curcumin monoacetate) to vanillin acetate. The non-protected vanillin moiety reacted to a mixture of higher molecular products. In the third step, the protecting group was removed from vanillin acetate using a feruloyl esterase from Pleurotus eryngii (PeFaeA) (68% molar yield). Alignment of the amino acid sequences indicated that high potential laccases performed better in this mediator and cofactor-free reaction.
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