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Penispirozines A-H, Three Classes of Dioxopiperazine Alkaloids with Spirocyclic Skeletons Isolated from the Mangrove-Derived Penicillium janthinellum.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-08-20 , DOI: 10.1021/acs.jnatprod.0c00451
Meilin Zhu 1, 2 , Zhen Yang 3 , Haotian Wang 2 , Qi Gan 1 , Guojian Zhang 1, 4 , Qian Che 1 , Tianjiao Zhu 1 , Qianqun Gu 1 , Bingnan Han 3 , Dehai Li 1, 4
Affiliation  

Eight new dioxopiperazine alkaloids, penispirozines A–H (18), were discovered from the mangrove-derived fungus Penicillium janthinellum HDN13-309. Their structures were elucidated by spectroscopic analysis, TDDFT-ECD calculations, and X-ray diffraction. Compound 1 had an unusual pyrazino[1,2]oxazadecaline coupled with a thiophane ring system, and compound 2 possessed a 6/5/6/5/6 pentacyclic ring system with two rare spirocyclic centers. Interestingly, compounds 38 were distinguished by not only the existence of a spiro-thiophane or spiro-furan ring system but also the chirality of the pentacyclic moiety. Compounds 3 and 4 increased the expression of the two relevant phase II detoxifying enzymes SOD2 and HO-1 at 10 μM.

中文翻译:

Penispirozines AH,三类具有螺环骨架的二氧哌嗪生物碱,从红树林衍生的 Penicillium janthinellum 中分离出来。

从红树林来源的真菌Penicillium janthinellum HDN13-309中发现了八种新的二氧哌嗪生物碱,penispirozines A–H ( 18 ) 。通过光谱分析、TDDFT-ECD 计算和 X 射线衍射阐明了它们的结构。化合物1具有与噻吩环系统偶联的不寻常的吡嗪并[1,2]氧氮杂萘,化合物2具有具有两个稀有螺环中心的6/5/6/5/6五环系统。有趣的是,化合物3 - 8的区别不仅在于存在螺-噻吩或-呋喃环系统以及五环部分的手性。化合物34在 10 μM 时增加了两种相关的 II 期解毒酶 SOD2 和 HO-1 的表达。
更新日期:2020-09-25
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