American Chemical Society
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Alkaloids and Polyketides from Penicillium citrinum, an Endophyte Isolated from the Moroccan Plant Ceratonia siliqua

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journal contribution
posted on 2016-02-19, 04:51 authored by Mona El-Neketi, Weaam Ebrahim, Wenhan Lin, Sahar Gedara, Farid Badria, Hassan-Elrady A. Saad, Daowan Lai, Peter Proksch
The endophytic fungus Penicillium citrinum was isolated from a fresh stem of the Moroccan plant Ceratonia siliqua. Extracts of P. citrinum grown on rice and white bean media yielded five new compounds, namely, citriquinochroman (1), tanzawaic acids G and H (2 and 3), 6-methylcurvulinic acid (4), 8-methoxy-3,5-dimethylisoquinolin-6-ol (5), and one new natural product, 1,2,3,11b-tetrahydroquinolactacide (6), which had previously been described as a synthetic compound. In addition, 13 known compounds including seven alkaloids and six polyketides were isolated. The structures of the new compounds were unambiguously determined on the basis of one- and two-dimensional NMR spectroscopy as well as by high-resolution mass spectrometry. Citriquinochroman (1) features a new skeleton, consisting of quinolactacide and (3S)-6-hydroxy-8-methoxy-3,5-dimethylisochroman linked by a C–C bond. 1,2,3,11b-Tetrahydroquinolactacide (6) may be a biogenetic precursor of quinolactacide. Citriquinochroman (1) showed cytotoxicity against the murine lymphoma L5178Y cell line with an IC50 value of 6.1 μM, while the other compounds were inactive (IC50 >10 μM) in this assay.