Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Yunnan Characteristic Plant Extraction Laboratory, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P. R. China.
Yunnan University of Chinese Medicine, Kunming, 650500, P. R. China.
Chem Biodivers. 2023 Apr;20(4):e202300004. doi: 10.1002/cbdv.202300004. Epub 2023 Mar 16.
The endophyte Nemania primolutea, inhibited the growth of Penicillium chrysogenum in the coculture system. Four new compounds, nemmolutines A-B (1-2), and penigenumin (3) from N. primolutea, penemin (4) from P. chrysogenum were isolated from the coculture. On the other hand, P. chrysogenum inhibited the Aspergillus fumigatus in the coculture. Induced metabolites (13-16) with monasone naphthoquinone scaffolds including a new one from P. chrysogenum were produced by the coculture of P. chrysogenum, and A. fumigatus. Interesting, cryptic metabolites penicichrins A-B isolated from wild P. chrysogenum induced by host Ziziphus jujuba medium were also found in induced P. chrysogenum cultured in PDB ordinary medium. So the induction of penicichrin production by supplementing with host extract occurred in the fungus P. chrysogenum not the host medium. The productions of penicichrins were the spontaneous metabolism, and the metabolites (13-16) were the culture driven. Compounds 4, 6, 8, 10, 11, 14, and 15 showed significant antifungal activities against the phytopathogen Alternaria alternata with MIC of 1-8 μg/mL, and compounds 7, 9, and 12 indicated significant antifeedant activities against silkworms with feeding deterrence indexes (FDIs) of 92 %, 66 %, and 64 %. The carboxy group in 4-(2-hydroxybutynoxy)benzoic acid derivatives, and xylabisboeins; the hydroxy group in mellein derivatives; and the quinoid in monasone naphthoquinone increased the antifungal activities.
内生真菌 Nemania primolutea 在共培养体系中抑制了 Penicillium chrysogenum 的生长。从 N. primolutea 中分离得到了四个新化合物，nemmolutines A-B（1-2）和 penigenumin（3），从 P. chrysogenum 中分离得到了 penemin（4）。另一方面，P. chrysogenum 在共培养体系中抑制了 Aspergillus fumigatus 的生长。通过 P. chrysogenum 和 A. fumigatus 的共培养，产生了具有 monasone naphthoquinone 支架的诱导代谢物（13-16），其中包括一个来自 P. chrysogenum 的新化合物。有趣的是，从野生 P. chrysogenum 中分离得到的隐色代谢物 penicichrins A-B 也在普通 PDB 培养基中培养的诱导 P. chrysogenum 中被发现。因此，penicichrin 的产生是通过补充宿主提取物而不是宿主培养基来诱导的。penicichrins 的产生是自发代谢，而代谢物（13-16）是培养驱动的。化合物 4、6、8、10、11、14 和 15 对植物病原菌Alternaria alternata 表现出显著的抗真菌活性，MIC 为 1-8 μg/mL，化合物 7、9 和 12 对家蚕表现出显著的拒食活性，摄食抑制指数（FDIs）分别为 92%、66%和 64%。4-（2-羟基丁炔氧基）苯甲酸衍生物、xylabisboeins 中的羧基；mellein 衍生物中的羟基；monasone naphthoquinone 中的醌增加了抗真菌活性。
