Abstract
Chemical investigation on the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475 led to the isolation of a previously undescribed (roquefortine J, 1) and four known (2−5) roquefortine alkaloids, along with six ergosterol analogues (6−11). The planar structure of 1 was established mainly on the basis of extensive analysis of its 1D, 2D NMR, and HRESIMS spectra. The absolute configuration of 1 was determined by comparison of the calculated and experimental electronic circular dichroism spectra. Compounds 5, 6, and 7 exhibited potent anti-proliferative effects against HepG2 tumor cells with IC50 values of 7.0, 8.6, and 8.2 μM, respectively.
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References
Soldatou S, Baker BJ. Cold-water marine natural products, 2006 to 2016. Nat Prod Rep. 2017;34:585–626.
Rateb ME, Ebel R. Secondary metabolites of fungi from marine habitats. Nat Prod Rep. 2011;28:290–344.
Elissawy AM, et al. Bioactive terpenes from marine-derived fungi. Mar Drugs. 2015;13:1966–92.
Agrawal S, et al. Marine fungi: an untapped bioresource for future cosmeceuticals. Phytochem Lett. 2018;23:15–20.
Navarri M, et al. Deep subseafloor fungi as an untapped reservoir of amphipathic antimicrobial compounds. Mar Drugs. 2016;14:50.
Skropeta D, Wei L. Recent advances in deep-sea natural products. Nat Prod Rep. 2014;31:999–1025.
Niu S, et al. Spiromastilactones: a new class of influenza virus inhibitors from deep-sea fungus. Eur J Med Chem. 2016;108:229–44.
Niu S, et al. Sesquiterpenes from a deep-sea-derived fungus Graphostroma sp. MCCC 3A00421. Tetrahedron. 2017;73:7267–73.
Niu S, et al. Cyclopiane-type diterpenes from the deep-sea-derived fungus Penicillium commune MCCC 3A00940. Tetrahedron Lett. 2018;59:375–8.
Niu S, et al. Spirograterpene A, a tetracyclic spiro-diterpene with a fused 5/5/5/5 ring system from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475. J Nat Prod. 2017;80:2174–7.
Scott PM, Polonsky J, Merrien MA. Configuration of the 3,12 double bond of roquefortine. J Agric Food Chem. 1979;27:201–2.
Trimble LA, et al. Characterization of (16R) and (16S)-hydroxyroquefortine C; diastereomeric metabolites from Penicillium crustosum DAOM 215343. Tetrahedron Lett. 2012;53:956–8.
Du L, et al. New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp. Tetrahedron. 2009;65:1033–9.
Kawai K, et al. Studies on fungal products. VII. The structures of meleagrin and 9-O-p-bromobenzoylmeleagrin. Chem Pharm Bull. 1984;32:94–8.
Chen S, Snyder JK. Diosgenin-bearing, molluscicidal saponins from Allium vineale: an NMR approach for the structural assignment of oligosaccharide units. J Org Chem. 1989;54:3679–89.
Gao S, et al. Penicisteroids A and B, antifungal and cytotoxic polyoxygenated steroids from the marine alga-derived endophytic fungus Penicillium chrysogenum QEN-24S. Bioorg Med Chem Lett. 2011;21:2894–7.
Igarashi Y, et al. Anicequol, a novel inhibitor for anchorage-independent growth of tumor cells from Penicillium aurantiogriseum Dierckx TP-F0213. J Antibiot. 2002;55:371–6.
Hu J, Kelly M, Hamann MT. 26-Nor-25-isopropyl-ergosta-5,7,22E-trien-3β-ol: a new C29 sterol from the sponge Agelas sceptrum from Jamaica. Steroids. 2002;67:743–7.
Kang J, Wang H, Chen R. Studies on the constituents of the mycelium produced by fermenting culture of Flammulina velutipes (W. Curt.:Fr.) Singer (Agaricomycetideae). Int J Med Mushrooms. 2003;5:391–6.
Sgarbi DBDG, et al. Isolation of ergosterol peroxide and its reversion to ergosterol in the pathogenic fungus Sporothrix schenckii. Mycopathologia. 1997;139:9–14.
Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983;65:55–63.
Acknowledgements
This study was supported by grants from the Science and Technology Research Program of Fujian Province, China (2017Y0060), the Fundamental Research for the Central University (2072016117), and the National Natural Science Foundation of China (41606185, 41676130, and 21372233).
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Niu, S., Wang, N., Xie, CL. et al. Roquefortine J, a novel roquefortine alkaloid, from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475. J Antibiot 71, 658–661 (2018). https://doi.org/10.1038/s41429-018-0046-y
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DOI: https://doi.org/10.1038/s41429-018-0046-y
