N-benzylideneaniline and N-benzylaniline are potent inhibitors of lignostilbene-α, β-dioxygenase, a key enzyme in oxidative cleavage of the central double bond of lignostilbene
N-benzylideneaniline and N-benzylaniline are potent inhibitors of lignostilbene-α, β-dioxygenase, a key enzyme in oxidative cleavage of the central double bond of lignostilbene
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DOI：
10.1080/1475636031000080207
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发表时间：
2003-05-26
影响因子：
5.6
通讯作者：
Asami, T
中科院分区：
文献类型：
--
作者：
Han, SY;Inoue, H;Asami, T
木二烯-α，β-双加氧酶(LSD，EC 1.13.11.43)参与木二烯中心双键的氧化裂解，形成相应的醛，其作用机制与9-顺式环氧卡洛烯双加氧酶和β-胡萝卜素15，15‘-双加氧酶相似，分别是脱落酸生物合成和维生素A生物合成的关键酶。在本研究中，我们合成了几种N-亚苄基苯胺和胺，并考察了它们作为LSD抑制剂的效果。N-(4-羟基亚甲基)-3-甲氧基苯胺是一种有效的缓蚀剂，其IC50为0.3um，N-(4-羟基苄基)-3-甲氧基苯胺的IC50为10um。从结构-活性关系研究中获得的信息有助于发现脱落酸和维生素A生物合成的抑制剂。
Lignostilbene-alpha, beta-dioxygenase (LSD, EC 1.13.11.43) is involved in oxidative cleavage of the central double bond of lignostilbene to form the corresponding aldehydes by a mechanism similar to those of 9-cis-epoxycarotenoid dioxygenase and beta-carotene 15,15'-dioxygenase, key enzymes in abscisic acid biosynthesis and vitamin A biosynthesis, respectively. In this study, several N-benzylideneanilines and amine were synthesized and examined for their efficacy as inhibitors of LSD. N-(4-Hydroxybenzylidene)-3-methoxyaniline was found to be a potent inhibitor with IC50=0.3 muM and N-(4-hydroxybenzyl)-3-methoxyaniline was also active with IC50=10 muM. The information obtained from the structure-activity relationships study here can aid in discovering inhibitors of both abscisic acid and vitamin A biosynthesis.