Novel 3,4-seco-3,19-dinorspongian and 5,17-epoxy-19-norspongian diterpenes from the marine sponge Spongia sp.,Organic Chemistry Frontiers

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Novel 3,4-seco-3,19-dinorspongian and 5,17-epoxy-19-norspongian diterpenes from the marine sponge Spongia sp.
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-09-17 , DOI: 10.1039/d0qo00977f
Yong-Qian Liang _{1,

2,

3,

4,

5} , Xiao-Jian Liao _{1,

2,

3,

4,

5} , Bing-Xin Zhao _{1,

2,

3,

4,

5} , Shi-Hai Xu _{1,

2,

3,

4,

5}

Affiliation

Twelve new norspongian diterpenes, dinorspongians A–F (1–6) and epoxynorspongians A–F (7–12), were isolated from the marine sponge Spongia sp. Compounds 1–6 were the first examples of dinorspongian diterpenes bearing the unprecedented 3,4-seco-3,19-dinorspongian diterpene skeleton. Compounds 7–12 were the new 19-norspongian diterpenes possessing a 5,17-epoxy unit firstly. The structures with absolute configurations of these compounds were elucidated by the methods of NMR, X-ray diffraction and quantum chemical calculation. The biogenetic routes of 1–12 were also proposed, which suggested that the 19-norspongian diterpenes might be the intermediates of 3,4-seco-3,19-dinorspongian diterpenes. It was the first time to discuss the biosynthetic relationship between these two types of norspongian diterpenes. In addition, all the compounds were evaluated for their cytotoxic activities against several cancer cell lines. Compound 11 showed moderate activities against the PC3 and PBL-2H3 cell lines with IC₅₀ values of 24.8 and 27.2 μM, respectively.

中文翻译：

来自海洋海绵Spongia sp。的新型3,4-seco-3,19-dinorspongian和5,17-epoxy-19-norspongian二萜。

从海洋海绵海绵宝宝中分离出了十二种新的挪威海绵体二萜，犬齿海绵体A–F（1–6）和环氧norspongians A–F（7–12）。化合物1–6是带有非同寻常的3,4-seco-3,19-dinorspongian二萜骨架的dinorspongian二萜的第一个实例。化合物7–12是首先具有5,17-环氧单元的新的19-北半球二萜。通过NMR，X射线衍射和量子化学计算等方法阐明了这些化合物的绝对构型。1–12的生物发生途径还提出，这表明19-北海绵体二萜可能是3,4-seco-3,19-二海绵体二萜的中间体。这是第一次讨论这两种类型的六面体二萜之间的生物合成关系。另外，评估了所有化合物对几种癌细胞系的细胞毒性活性。化合物11对PC3和PBL-2H3细胞系表现出中等活性，IC ₅₀值分别为24.8和27.2μM。

更新日期：2020-10-13

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