| Summary: | Three new azaphilone alkaloids containing glutamine residues, namely <i>N</i>-glutarylchaetoviridins A−C (<b>1</b>−<b>3</b>), together with two related compounds (<b>4</b> and <b>5</b>) were isolated from the extract of <i>Chaetomium globosum</i> HDN151398, a fungus isolated from a deep-sea sediment sample collected in South China Sea. Their structures were elucidated on the basis of extensive 1D and 2D NMR as well as HRESIMS spectroscopic data and chemical analysis. <i>N</i>-glutarylchaetoviridins A−C (<b>1</b>−<b>3</b>) represent the first class of chaetoviridins characterized by embedded glutamate residues. Amino acids incubation experiments produced five azaphilone laden different amino acids residues (<b>6</b>−<b>10</b>) which indicated that this method can enhanced the structural diversity of this strain by culturing with amino acids. Cytotoxicity of the isolated compounds were evaluated against a panel of human cancer cell lines.
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