Colletotrichalasin A: a hepatoprotective decalin-tetramic acid derivative featuring a pentacyclic 6/6/5/6/5 ring skeleton from the endophytic fungus Colletotrichum gloeosporioides MT-51 of Huperzia serrata

IF 1.5 4区化学 Q3 CHEMISTRY, ORGANIC

Tetrahedron Letters Pub Date : 2025-06-04 DOI:10.1016/j.tetlet.2025.155691

Bei-Bei Zhang , Hong-Yun Yang , Xiao-Yun Yan , Na Xiong , Lin Zhang , Xiao Liu , Pei-Cheng Zhang , She-Po Shi , Xu Zhang , Juan Wang

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Abstract

A hepatoprotective decalin-tetramic acid derivative colletotrichalasin A (1) which possesses a unique pentacyclic 6/6/5/6/5 fused ring system was isolated from the endophytic fungus Colletotrichum gloeosporioides MT-51 of Huperzia serrata. Besides, three known alkaloids (2–4) were also obtained. Their planar structures were established through integrative NMR, UV, IR, and HRESIMS spectroscopic analysis. The absolute configuration of compound 1 was determined using GIAO ¹³C NMR DP4+ analysis and electronic circular dichroism (ECD) calculations. Compound 1 exhibited significant hepatoprotective activity with 74.6 % cell viability (p < 0.0001) at a concentration of 10 μM. A plausible biosynthetic pathway for 1 was proposed based on its PK-NRP hybrid scaffold.

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炭疽菌素A：一种保护肝脏的十钙素四羧酸衍生物，其五环骨架为6/6/5/6/5，来自胡杉属内生真菌炭疽菌MT-51

从serrata石杉内生真菌Colletotrichum gloeosporioides MT-51中分离得到一种具有独特五环6/6/5/6/5融合环体系的保肝十钙素四酸衍生物colletotrichalasin A(1)。此外，还得到了3种已知的生物碱（2-4）。通过核磁共振、紫外、红外和hresms光谱综合分析，确定了它们的平面结构。采用GIAO 13C NMR DP4+分析和电子圆二色性（ECD）计算确定了化合物1的绝对构型。化合物1具有显著的肝保护作用，细胞存活率为74.6% (p <；0.0001)，浓度为10 μM。基于其PK-NRP杂交支架，提出了1的生物合成途径。

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来源期刊

Tetrahedron Letters 化学-有机化学

CiteScore

3.50

自引率

5.60%

发文量

521

审稿时长

28 days

期刊介绍： Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.