Seco and Nor-seco Isodhilarane-Type Meroterpenoids from Penicillium purpurogenum and the Configuration Revisions of Related Compounds.
Seco and Nor-seco Isodhilarane-Type Meroterpenoids from Penicillium purpurogenum and the Configuration Revisions of Related Compounds.
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DOI：
10.1021/acs.jnatprod.1c01025
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发表时间：
2022-01
影响因子：
5.1
通讯作者：
Yuzhuo Wu;Guiyang Xia;Huan Xia;Lingyan Wang;Yanan Wang;Li Li-Li;H. Shang;Sheng Lin
中科院分区：
文献类型：
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作者：
Yuzhuo Wu;Guiyang Xia;Huan Xia;Lingyan Wang;Yanan Wang;Li Li-Li;H. Shang;Sheng Lin
Seco和non - Seco isodhilarane-type meroterpenoids （SIMs和NSIMs）主要存在于青霉属真菌中，具有高度密集的多环骨架和广泛的生物活性。然而，由于其复杂的多环系统和多手性中心，一些SIMs和NSIMs的构型分配不一致。在本文中，我们描述了从紫霉菌EtOAc提取物中分离的8个SIMs和NSIMs，这导致purpurogenolide C (1a)， berkeley缩醛B (2a), chrygenolide F （3a）和berkeley缩醛C （4a）的构型修改，分别为化合物1-4。此外，对已报道的39个SIMs和NSIMs的实验和计算13C NMR化学位移进行了广泛的重新评估，为确定C-9的相对构型提供了一种经验方法，根据C-9的13C NMR化学位移，这有助于对另外三个SIMs （5a和6a）和NSIMs （7a）的构型进行修正，分别表示为化合物5-7。生物实验表明，化合物3对HepG2和A549细胞株具有细胞毒活性，IC50值分别为5.58和6.80 μM。化合物2-4、8、9和32在apap诱导的HepG2细胞损伤模型中表现出10 μM的中度肝保护活性。
Seco and nor-seco isodhilarane-type meroterpenoids (SIMs and NSIMs) are mainly found in Penicillium fungi and have been characterized by highly congested polycyclic skeletons and a broad range of bioactivities. However, the literature reports inconsistent configuration assignments for some SIMs and NSIMs, due to their complex polycyclic systems and multichiral centers. Herein, we described eight SIMs and NSIMs isolated from the EtOAc extract of Penicillium purpurogenum, which led to the configuration revisions of purpurogenolide C (1a), berkeleyacetal B (2a), chrysogenolide F (3a), and berkeleyacetal C (4a) as compounds 1-4, respectively. Furthermore, extensive re-evaluation of the experimental and computational 13C NMR chemical shifts of the reported 39 SIMs and NSIMs provided an empirical approach for determining the C-9 relative configuration, according to the 13C NMR chemical shifts of C-9, which contributed to the configuration revisions of another three SIMs (5a and 6a) and NSIMs (7a), denoted as compounds 5-7, respectively. Biological assays indicated that compound 3 exhibited cytotoxic activity against HepG2 and A549 cell lines with IC50 values of 5.58 and 6.80 μM, respectively. Compounds 2-4, 8, 9, and 32 showed moderate hepatoprotective activity at 10 μM in the APAP-induced HepG2 cell injury model.