Bistachybotrysins L–V, bioactive phenylspirodrimane dimers from the fungus Stachybotrys chartarum,Organic Chemistry Frontiers

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Bistachybotrysins L–V, bioactive phenylspirodrimane dimers from the fungus Stachybotrys chartarum
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2019/12/26 , DOI: 10.1039/c9qo01284b
Jimei Liu _{1,

2,

3,

4,

5} , Xiaona Jia _{1,

2,

3,

4,

5} , Jinlian Zhao _{1,

2,

3,

4,

5} , Jiamin Feng _{1,

2,

3,

4,

5} , Minghua Chen _{5,

6,

7,

8,

9} , Ridao Chen _{1,

2,

3,

4,

5} , Kebo Xie _{1,

2,

3,

4,

5} , Dawei Chen _{1,

2,

3,

4,

5} , Yan Li _{1,

2,

3,

4,

5} , Dan Zhang _{1,

2,

3,

4,

5} , Ying Peng _{1,

2,

3,

4,

5} , Shuyi Si _{5,

6,

7,

8,

9} , Jungui Dai _{1,

2,

3,

4,

5}

Affiliation

Bistachybotrysins L–V (1–11), eleven novel dimeric phenylspirodrimanes, were isolated from the fungus Stachybotrys chartarum CGMCC 3.5365. Among them, 1 and 2, a pair of stereoisomeric dimers represent an unusual aromatic [5,6]-spiroketal skeleton with a central 2-methoxy-1,6-dioxaspiro[4.5]decane core fused with two phenyl units. Their structures, including absolute configurations, were elucidated using extensive spectroscopic data, single-crystal X-ray diffraction (Cu Kα), and calculated electronic circular dichroism (ECD) analyses. Biological assay revealed that 2 showed potent cytotoxicity against five human tumor cell lines with IC₅₀ values in the range of 1.8–3.5 μM; 2, 3, and 9 displayed neuroprotective effects toward the glutamate-induced toxicity in SK-N-SH cells by increasing cell viability 17.4%–17.6% at 10.0 μM; and 8 exhibited anti-inflammatory activity by suppressing LPS-induced NO production in BV2 cells with an inhibition rate of 54.2% at 10.0 μM. Furthermore, the possible biogenetic pathways of these compounds are proposed.

中文翻译：

Bistachybotrysins L–V，来自真菌Stachybotrys chartarum的生物活性苯基螺嘧啶二聚体

从真菌Stachybotrys chartarum CGMCC 3.5365中分离出11种新颖的二聚苯基螺螺旋体Bistachybotrysins L–V（1-11）。其中1和2是一对立体异构体二聚体，代表不寻常的芳香族[5,6]-螺骨架，中心为2-甲氧基-1,6-二氧杂螺环[4.5]癸烷核心，并带有两个苯基单元。使用广泛的光谱数据，单晶X射线衍射（CuKα）和计算的电子圆二色性（ECD）分析，阐明了它们的结构，包括绝对构型。生物学分析表明，有2种药物对5种人类肿瘤细胞系具有有效的细胞毒性，IC ₅₀值在1.8–3.5μM之间。2，3和9显示朝向SK-N-SH细胞中的谷氨酸盐诱导的毒性的神经保护作用通过增加细胞活力17.4％-17.6％的10.0μM; 8和8通过抑制LPS诱导的BV2细胞中NO的产生具有抗炎活性，在10.0μM时抑制率为54.2％。此外，提出了这些化合物的可能的生物遗传途径。

更新日期：2020-02-13

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