20-nor-Isopimarane and isopimarane diterpenoids produced by Aspergillus sp. WT03,Organic & Biomolecular Chemistry

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20-nor-Isopimarane and isopimarane diterpenoids produced by Aspergillus sp. WT03
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2023-02-01 , DOI: 10.1039/d3ob00005b
Qiaoqiao Tao ₁ , Yining Sang ₁ , Tao Han ₁ , Hongling Zhou ₁ , Peng Zhang ₁ , Xiaofeng Cai _{1,

2}

Affiliation

Five new uncommon 20-nor-isopimarane diterpenoids, aspewentins N–R (1–5), and three related known congeners (6–8), along with an isopimarane diterpenoid, sphaeropsidin C (9), were isolated from a Coptis chinensis Franch. rhizosphere soil-derived fungal strain, Aspergillus sp. WT03. The structures of compounds 1–9 were characterized based on the comprehensive analysis of the spectroscopic data, and their absolute configurations were elucidated by single crystal X-ray diffraction and time-dependent density functional theory (TDDFT)-ECD calculations. Compounds 1–5 represent rare examples of 20-nor-isopimarane analogues featuring a 1,2,3,4-tetrahydronaphthalene and 3,4-dihydronaphthalen-1(2H)-one moiety. The biosynthetic pathway of these diterpenoids was also proposed. Additionally, compounds 1, 3 and 4 showed moderate cytotoxic activity against MCF-7, A549 and HT-29 cell lines.

中文翻译：

由曲霉菌产生的 20-nor-Isopimarane 和 isopimarane 二萜类化合物。WT03

五种新的不常见的 20- nor -isopimarane 二萜类化合物，aspewentins N-R ( 1-5 )，和三种相关的已知同源物 ( 6-8 )，以及一种 isopimarane 二萜类化合物 sphaeropsidin C ( 9 )，是从黄连中分离出来的. 根际土壤来源的真菌菌株，曲霉菌属。WT03。基于光谱数据的综合分析表征了化合物 1-9 的结构，并通过单晶 X 射线衍射和瞬态密度泛函理论 (TDDFT)-ECD 计算阐明了它们的绝对构型。化合物1-5代表 20- nor的罕见例子-isopimarane 类似物，具有 1,2,3,4-四氢萘和 3,4-二氢萘-1(2 H )-一个部分。还提出了这些二萜类化合物的生物合成途径。此外，化合物1、3和4显示出针对 MCF-7、A549 和 HT-29 细胞系的中等细胞毒活性。

更新日期：2023-02-01

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