Abstract
Two new polyketides, penifellutins A (1) and B (2), possessing a 22 carbon linear skeleton, were isolated from a co-culture of the deep-sea-derived fungi Penicillium crustosum PRB-2 and Penicillium fellutanum HDN14-323. Meanwhile, two esterification products of 1, penifellutins C (3) and D (4), were obtained because compound 1 could be esterified spontaneously when stored in methanol. Their configurations were difficult to determine because of chiral central crowdedness, structural flexibility and instability. As such, we solved this issue by comprehensively using Mo2(OAc)4-based CD experiments, density functional theory calculation of 13C NMR, DP4 + probability analysis and many chemical reactions, including making acetonide derivative, Mosher’s method, PGME method, etc. Compounds 1 and 2 show obvious inhibitory activity on the liver hyperplasia of zebrafish larvae at a concentration of 10 μmol/L, while 3 and 4 show no activity, indicating that two carboxyls in the structure are important active sites.
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Acknowledgements
This work was financially supported by the National Natural Science Foundation of China (41806167, 81670709), Project funded by China Postdoctoral Science Foundation (2017M622286), Qingdao Postdoctoral Applied Research Project Financially Supported by Qingdao Municipal Bureau of Human Resource and Social Security, Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology (LMDBKF201805), and High-level Talents Research Fund of Qingdao Agricultural University (Grants 665/1120034). We thank Dr. Zhiyuan Gong (National Univeristy of Singapore) for the gift of Tg (Fabp10-rtTA:TRE-eGFPKRASV12) transgenic line.
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GY and PS contributed equally. DL and ML conceived and designed the experiments; GY and PS performed the experiments; RA, CS, ZZ, QC, GZ, TZ, QG participated in the experimental process and result discussion. GY analyzed the data and wrote the paper.
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This article does not contain any studies with human participants. All procedures on animals have been approved by the Xiamen University Institutional Animal Care and Use Committee (Protocol XMULAC20160089, 10 March 2016).
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Yu, G., Sun, P., Aierken, R. et al. Linear polyketides produced by co-culture of Penicillium crustosum and Penicillium fellutanum. Mar Life Sci Technol 4, 237–244 (2022). https://doi.org/10.1007/s42995-021-00125-8
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DOI: https://doi.org/10.1007/s42995-021-00125-8