<jats:title>Abstract</jats:title><jats:p>Bioactivity‐guided fractionation of the cytotoxic extract of <jats:italic>Aspergillus niger</jats:italic>, an endophytic fungus from the Chinese liverwort <jats:italic>Heteroscyphus tener</jats:italic> (<jats:sc>Steph</jats:sc>.) <jats:sc>Schiffn</jats:sc>., afforded five new naphtho‐<jats:italic>γ</jats:italic>‐pyrones, rubrofusarin‐6‐<jats:italic>O</jats:italic>‐<jats:italic>α</jats:italic>‐<jats:sc>D</jats:sc><jats:italic>‐</jats:italic>ribofuranoside (<jats:bold>1</jats:bold>), (<jats:italic>R</jats:italic>)‐10‐(3‐succinimidyl)‐TMC‐256A1 (<jats:bold>2</jats:bold>), asperpyrone E (<jats:bold>3</jats:bold>), isoaurasperone A (<jats:bold>4</jats:bold>), and isoaurasperone F (<jats:bold>5</jats:bold>), as well as four known ones, dianhydroaurasperone C (<jats:bold>6</jats:bold>), aurasperone D (<jats:bold>7</jats:bold>), asperpyrone D (<jats:bold>8</jats:bold>), and asperpyrone A (<jats:bold>9</jats:bold>), together with a cytotoxic cyclic pentapeptide, malformin A<jats:sub>1</jats:sub> (<jats:bold>10</jats:bold>). Their structures were determined by extensive spectroscopic analysis. The absolute configurations of dimeric naphtho‐<jats:italic>γ</jats:italic>‐pyrones <jats:bold>3</jats:bold>–<jats:bold>9</jats:bold> were also determined by analysis of their respective CD spectra.