Abstract
A new meroterpenoid, taladrimanin A (1), was isolated from a marine-derived fungus Talaromyces sp. HM6-1–1, together with eleven biogenetically related compounds (2–12). A plausible biosynthetic pathway for the meroterpenoids (1–4) was proposed. The planar structure of 1 was assigned by HRESIMS and NMR. Its relative configuration was established by quantum chemical NMR calculation of two possible isomers and analyzed by DP4 + method. Finally, X-ray diffraction unambiguously confirmed the relative configuration and revealed the absolute configuration of compound 1. 2–12 were assigned by comparing their NMR data with those reported in the literature. 1 was the first drimane-type meroterpenoid with a C10 polyketide unit bearing an 8R-configuration. In the bioactive assay, 1 exhibited antitumor activity against gastric cancer cells MGC803 and MKN28; it also inhibited the colony formation and induced apoptosis in MGC803 cells both in a concentration-dependent manner. Additionally, 1 displayed selective antibacterial activity against Staphylococcus aureus 6538P, and low activities towards strains of Vibrio parahaemolyticus and Escherichia coli in this study.
Key points
• Twelve compounds were obtained from Talaromyces sp., including four meroterpenoids, one of which was new.
• The new compound taladrimanin A (1) inhibits the growth of gastric cancer cells MGC803 and MKN28 as well as the pathogenic bacteria Staphylococcus aureus 6538P.
• The biosynthetic pathway of the meroterpenoids was proposed.
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Data availability
All data generated or analyzed during this study are included in this published article and its supplementary information files. The strain used in this study was deposited in the Marine Culture Collection of China (MCCC) with an accession number of MCCC M27416. The deposition number for the X-ray crystallography data of compound 1 was CCDC 2,126,900.
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Acknowledgements
We are grateful to Dr. Xu Ran, for his contribution to the logic of language in this paper.
Funding
This research was supported by the Natural Science Foundation of Fujian Province (2021J01509), Scientific Research Foundation of Third Institute of Oceanography SOA (2018021), National Natural Science Foundation of China (41906104), Deep Sea Habitats Discovery Project (DY-XZ-04), Research project on education and teaching reform in undergraduate colleges and universities of Fujian Province (FBJG20190201), Natural Science Foundation of Zhejiang Province (LR21H280001, Q22H287247), National Natural Science Foundation of China (81903842), COMRA program (DY135-B2-01 & DY135-B2-05), and Scientific Research Foundation of Third Institute of Oceanography MNR (2019021).
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Investigation, X.H., X.G., W.W., D.Y.; resources, Q.L., Z.C., X.F., C.C.; data analysis, B.Z., W.W., J.X.; writing—original draft preparation, W.W., J.-J.Q.; writing—revision, Z.S., J.X..
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253_2022_11914_MOESM1_ESM.pdf
Supplementary file1 NMR spectra compound 1 as well as computation data for (8′R*)-1 and (8′S*)-1 are provided in Figs. S1 to S110 and Tables S1 and S15. (PDF 1517 KB)
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Hong, X., Guan, X., Lai, Q. et al. Characterization of a bioactive meroterpenoid isolated from the marine-derived fungus Talaromyces sp.. Appl Microbiol Biotechnol 106, 2927–2935 (2022). https://doi.org/10.1007/s00253-022-11914-1
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DOI: https://doi.org/10.1007/s00253-022-11914-1