Penispirozines A-H, Three Classes of Dioxopiperazine Alkaloids with Spirocyclic Skeletons Isolated from the Mangrove-Derived Penicillium janthinellum.,Journal of Natural Products

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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 (1–8), 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 3–8 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 ( 1 – 8 ) 。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-噻吩或螺-呋喃环系统以及五环部分的手性。化合物3和4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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