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<i>Vanderbylia robiniophila</i> (Huaier in Chinese) has been used as a traditional herbal medicine in China for over 1600 years. However, the secondary metabolites of <i>V. robiniophila</i> have not been systematically examined. Corresponding chemical investigation in this study led to the discovery of two new compounds, (22<i>E</i>, 24<i>R</i>)-6<i>β</i>, 7<i>α</i>-dimethoxyergosta-8(14), 22-diene-3<i>β</i>, 5<i>α</i>-diol (<b>1</b>) and vanderbyliolide A (<b>8</b>), along with eight known ones (<b>2</b>–<b>7</b>, <b>9</b>–<b>10</b>). Their structures were determined by extensive spectroscopic analyses and electronic circular dichroism (ECD) calculations. The tyrosinase inhibitory activity of all isolated compounds was evaluated, and compound <b>10</b> showed a potential tyrosinase inhibitory effect with an IC₅₀ value of 60.47 ± 2.63 μM. Kinetic studies of the inhibition reactions suggested that <b>10</b> provides the inhibitory ability on tyrosinase in an uncompetitive way.