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New Antibacterial Dihydropyrones Induced by Co-Culture of Penicillium crustosum PRB-2 and Penicillium citrinum HDN11-186

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Abstract

Two new dihydropyrones, rhytismatones C (1) and D (2), and a known compound, penicillenol A1 (3), were isolated from the co-culture broth of the deep-sea-derived fungus Penicillium crustosum PRB-2 and Suaeda salsa-derived endophytic fungus Penicillium citrinum HDN11-186. Their structures were elucidated through comprehensive analysis of nuclear magnetic resonance (NMR) spectra and mass spectra. The absolute configurations of new compounds were determined by calculating the electronic circular dichroism (ECD) spectrum. UPLC-MS data showed that compounds 13 could only be detected in the media of co-culture, suggesting new biosynthetic pathways were activated in the co-cultured fungi. Compound 1 showed obvious antibacterial activities against Proteus sp. MMBC-1002 and Bacillus subtilis MMBC-1004 with minimum inhibitory concentration (MIC) both at 25 µmol L−1.

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References

  • Boddy, L., 2000. Interspecific combative interactions between wood-decaying basidiomycetes. FEMS Microbiology Ecology, 31(3): 185–194.

    Article  Google Scholar 

  • Cho, J. Y., and Kim, M. S., 2012. Induction of antifouling diterpene production by Streptomyces cinnabarinus PK209 in co-culture with marine-derived Alteromonas sp. KNS-16. Bioscience, Biotechnology, and Biochemistry, 76(10): 1849–1854.

    Article  Google Scholar 

  • Knowles, S. L., Raja, H. A., Roberts, C. D., and Oberlies, N. H., 2022. Fungal-fungal co-culture: A primer for generating chemical diversity. Natural Product Reports, 39(8): 1557–1573.

    Article  Google Scholar 

  • Knowles, S. L., Raja, H. A., Wright, A. J., Lee, A. M. L., Caesar, L. K., Cech, N. B., et al., 2019. Mapping the fungal battlefield: Using in situ chemistry and deletion mutants to monitor interspecific chemical interactions between fungi. Frontiers in Microbiology, 10: 285.

    Article  Google Scholar 

  • Li, C., Wang, J., Luo, C., Ding, W., and Cox, D. G., 2014. A new cyclopeptide with antifungal activity from the co-culture broth of two marine mangrove fungi. Natural Product Research, 28(9): 616–621.

    Article  Google Scholar 

  • McMullin, D. R., Green, B. D., Prince, N. C., Tanney, J. B., and Miller, J. D., 2017. Natural products of Picea endophytes from the Acadian forest. Journal of Natural Products, 80(5): 1475–1483.

    Article  Google Scholar 

  • Moody, S. C., 2014. Microbial co-culture: Harnessing intermicrobial signaling for the production of novel antimicrobials. Future Microbiology, 9(5): 575–578.

    Article  Google Scholar 

  • Qu, Q., Yang, F., Zhao, C., and Shi, X., 2019. Analysis of the bacteria community in wild Cordyceps cicadae and its influence on the production of HEA and nucleosides in Cordyceps cicadae. Journal of Applied Microbiology, 127(6): 1759–1767.

    Article  Google Scholar 

  • Sengoku, T., Wierzejska, J., Takahashi, M., and Yoda, H., 2010. First stereoselective synthesis of Penicillenol A1 via novel O-to C-acyl rearrangement of O-acyltetramic acid. Synlett, 2010(19): 2944–2946.

    Article  Google Scholar 

  • Watanabe, T., Izaki, K., and Takahashi, H., 1982. New polyenic antibiotics active against gram-positive and -negative bacteria. I. Isolation and purification of antibiotics produced by Gluconobacter sp. W-315. Journal of Antibiotics, 35(9): 1141–1147.

    Article  Google Scholar 

  • Wu, G., Ma, H., Zhu, T., Li, J., Gu, Q., and Li, D., 2012. Penilactones A and B, two novel polyketides from Antarctic deep-sea derived fungus Penicillium crustosum PRB-2. Tetrahedron, 68: 9745–9749.

    Article  Google Scholar 

  • Wu, G., Qian, X., Huang, Y., Liu, Y., Zhou, L., Wang, W., et al., 2022. Nonenzymatic self-assembly access to diverse ortho-quinone methide-based pseudonatural products. Organic Letters, 24(28): 5235–5239.

    Article  Google Scholar 

  • Yu, G., Sun, P., Aierken, R., Sun, C., Zhang, Z., Che, Q., et al., 2022. Linear polyketides produced by co-culture of Penicillium crustosum and Penicillium fellutanum. Marine Life Science & Technology, 4(2): 237–244.

    Article  Google Scholar 

  • Yu, G., Sun, Z., Peng, J., Zhu, M., Che, Q., Zhang, G., et al., 2019. Secondary metabolites produced by combined culture of Penicillium crustosum and a Xylaria sp. Journal of Natural Products, 82(7): 2013–2017.

    Article  Google Scholar 

  • Yu, G., Wu, G., Sun, Z., Zhang, X., Che, Q., Gu, Q., et al., 2018. Cytotoxic tetrahydroxanthone dimers from the mangrove-associated fungus Aspergillus versicolor HDN1009. Marine Drugs, 16(9): 335.

    Article  Google Scholar 

  • Yu, G., Zhou, G., Zhu, M., Wang, W., Zhu, T., Gu, Q., et al., 2016. Neosartoryadins A and B, fumiquinazoline alkaloids from a mangrove-derived fungus Neosartorya udagawae HDN13313. Organic Letters, 18(2): 244–247.

    Article  Google Scholar 

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 41806167), the High-Level Talents Research Fund of Qingdao Agricultural University (No. 665/1120034), the NSFC-Shandong Joint Fund (No. U1906212), the Major Project of the 14th Five-Year Plan (No. 2022QNLM030003-1), the Natural Science Foundation of Shandong Province (No. ZR2021ZD28), the Hainan Provincial Joint Project of Sanya Yazhou Bay Science and Technology City (No. 2021CXLH0012), and the Youth Innovation Plan of Shandong Province (No. 2019KJM004).

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Correspondence to Guihong Yu.

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Yu, G., Zhou, L., Wu, G. et al. New Antibacterial Dihydropyrones Induced by Co-Culture of Penicillium crustosum PRB-2 and Penicillium citrinum HDN11-186. J. Ocean Univ. China 23, 216–220 (2024). https://doi.org/10.1007/s11802-023-5676-4

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  • DOI: https://doi.org/10.1007/s11802-023-5676-4

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