Two new benzophenones and one new natural amide alkaloid isolated from a mangrove-derived Fungus Penicillium citrinum

Abstract

Two new compounds penibenzophenones A-B (1-2), and the synthetic α,β-unsaturated amide alkaloid (E)-tert-butyl(3-cinnamamidopropyl)carbamate (4), newly identified as a natural product, alone with three known ones (3, 5-6) were isolated from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea. Compound 1 was a chlorinated benzophenone. The structures of 1-6 were elucidated by extensive NMR spectral interpretation, MS data and X-ray analysis. The new compound 2 displayed cytotoxic activity against human A549 cell lines with an IC value of 15.7 μg/mL, and 1 showed antibacterial activity against Staphylococcus aureus with a MIC value of 20 μg/mL.

Molecular Phylogenetics and Biological Potential of Fungal Endophytes From Plants of the Sundarbans Mangrove

“…However, this is the first report of the isolation of Penicillium citrinum and Aspergillus fumigatus from A. alba and A. marina, respectively. Penicillium citrinum and Pestalotiopsis foedan are present in Bruguiera sexangula (Xu et al, 2016;Zheng et al, 2019). We report here for the first time the presence of Aspergillus species, including A. oryzae and A. terreus in Bruguiera sexangula.…”

Biological Activities of Some New Secondary Metabolites Isolated from Endophytic Fungi: A Review Study

“…Two new compounds penibenzophenones A-B 208-209 (Figure 6), were isolated from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Bruguiera sexangula var. rhynchopetala collected in the South China Sea [66]. Two new isochromanone derivatives, (3S,4S)-3,8-dihydroxy-6-methoxy-3,4,5trimethylisochroman-1-one 210 (Figure 6) and methyl (S)-8-hydroxy-6-methoxy-5-methyl-4a-(3-oxobutan-2-yl)benzoate 211 (Figure 6), were isolated from the cultures of an endophytic fungus Phoma sp.…”

“…A synthetic α,β-unsaturated amide alkaloid (E)-tert-butyl(3-cinnamamidopropyl) carbamate 217 (Figure 7), newly identified as a natural product, was isolated from the EtOAc extract of the endophytic fungus Penicillium citrinum HL-5126 isolated from the mangrove Bruguiera sexangula var. Rhynchopetala [66]. A new alkaloid, 1, 2-dihydrophenopyrrozin 218 (Figure 7), was isolated from an axenic culture of the endophytic fungus, Bionectria sp., obtained from seeds of the tropical plant Raphia taedigera [70].…”

Mangrove-Associated Fungi: A Novel Source of Potential Anticancer Compounds

“…rhynchopetala collected in the South China Sea. The new compound 108 displayed cytotoxic activity against human A549 cell lines with an IC 50 value of 15.7 µg/mL [ 60 ].…”