New dimeric compounds of avenanthramide phytoalexin in oats
New dimeric compounds of avenanthramide phytoalexin in oats
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DOI：
10.1021/jo0701740
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发表时间：
2007-05-11
影响因子：
3.6
通讯作者：
Iwamura, Hajime
中科院分区：
文献类型：
--
作者：
Okazaki, Yozo;Ishizuka, Akihiro;Iwamura, Hajime
燕麦虫胺B是燕麦在应对病原体攻击和诱导时产生的一种植物抗菌素。我们发现在诱导的燕麦叶片中形成新的二聚体（1-5）。该二聚体是在过氧化氢存在下，由过氧化物酶和阿维那甲酰胺B反应合成的。通过光谱分析、化学衍生化和N-15标记确定了1-5的结构。化合物1是具有丁烷内酰胺骨架的avenanthramide B的脱氢二聚体，而2-4是具有丁烷内酰胺结构的一水合脱氢二聚体。化合物5也是一水合脱氢二聚体，但具有四氢呋喃结构。所有化合物都被归类为木脂素酰胺，由两个avenanthramide B单元之间的8 ‘-8 ’偶联反应形成。
[GRAPHICS]Avenanthramide B is an oat phytoalexin produced in response to pathogen attack and elicitation. We found the formation of new dimers (1-5) of avenanthramide B in elicited oat leaves. The dimers were synthesized by a reaction of peroxidase and avenanthramide B in the presence of hydrogen peroxide. The structures of 1-5 were determined by spectroscopic analyses, chemical derivatization, and N-15 labeling. Compound 1 was a dehydrodimer of avenanthramide B with a bisbutane lactam skeleton, while 2-4 were monohydrated dehydrodimers with butane lactam structures. Compound 5 was also a monohydrated dehydrodimer but with a tetrahydrofuran structure. All the compounds were classified into lignanamides that were formed by an 8 '-8 ' coupling reaction between two avenanthramide B units.