Asperorydines A–M: Prenylated Tryptophan-Derived Alkaloids with Neurotrophic Effects from Aspergillus oryzae,The Journal of Organic Chemistry

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Asperorydines A–M: Prenylated Tryptophan-Derived Alkaloids with Neurotrophic Effects from Aspergillus oryzae
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-01-09 00:00:00 , DOI: 10.1021/acs.joc.7b02802
Li Liu _{1,

2} , Li Bao _{1,

2} , Long Wang ₁ , Ke Ma _{1,

2} , Junjie Han _{1,

2} , Yanlong Yang ₁ , Ruixing Liu _{1,

2} , Jinwei Ren ₁ , Wenbing Yin _{1,

2} , Wenzhao Wang ₁ , Hongwei Liu _{1,

2}

Affiliation

As part of our program to discover new bioactive agents from fungi, 13 new alkaloids accompanying 13 known related alkaloids were isolated from a wild strain of Aspergillus oryzae L1020. Compounds 1 and 2 have unprecedented 6/6/5/7/5 and 6/6/6/5/5 chemical skeletons, representing new members of quinoline alkaloids. Compound 3 is a new macrolactam with an unusual 6/5/6/8 ring system. Compounds 4–13 are new α-cyclopiazonic acid-related alkaloids. The absolute configurations of 1–4, 8, and 9 were assigned by electronic circular dichroism calculations. Compounds 2, 5, 6, 11, 14, 22, and 26 exhibit pronounced neurite outgrowth-promoting effects on PC12 cells in the range of 25–100 μM.

中文翻译：

Asperorydines A–M：米曲霉神经营养作用的烯丙基化色氨酸衍生生物碱

作为我们从真菌中发现新生物活性剂的计划的一部分，从野生米曲霉L1020菌株中分离出13种新生物碱和13种已知相关生物碱。化合物1和2具有前所未有的6/6/5/7/5和6/6/6/5/5化学骨架，代表了喹啉生物碱的新成员。化合物3是一种新的大内酰胺，具有不寻常的6/5/6/8环系统。化合物4 - 13是新的α-环匹阿尼酸相关的生物碱。的绝对构型1 - 4，8，和9是由电子圆二色性的计算分配。化合物2，5，6，11，14，22，和26显示出显着的神经突伸展促进在25-100微米的范围内对PC12细胞的影响。

更新日期：2018-01-09

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