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A series of meroterpenoids with rearranged skeletons from an endophytic fungus Penicillium sp. GDGJ-285

: Mo, T.-X.; Huang, X.-S.; Zhang, W.-X.; Schäberle, T.F.; Qin, J.-K.; Zhou, D.-X.; Qin, X.-Y.; Xu, Z.-L.; Li, J.; Yang, R.-Y.


Organic chemistry frontiers 8 (2021), Nr.10, S.2232-2241
ISSN: 2052-4129
ISSN: 2052-4110
Fraunhofer IME ()

Under the guidance of MS/MS based molecular networking, five new meroterpenoids (1–5), including three novel skeleton meroterpenoids, peniclactones A–C (1–3), and two new isoaustinone analogues, 6-hydroxyisoaustinone (4) and 6-ketoisoaustinone (5), were isolated from the fungus Penicillium sp. GDGJ-285. Their structures were elucidated by HRMS and NMR spectroscopy, and their absolute configurations were determined by X-ray single-crystal diffraction analysis. Peniclactones A–C (1–3) represent the first meroterpenoids featuring a 6/5/6/6/5/6 (1), 6/5/6/6/5/5 (2), and 6/5/6/5/5/6 (3) hexacyclic ring system, respectively. Bioassays showed that compound 3 inhibited nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells with an IC50 value of 39.03 μM.