Thirteen previously undescribed chromene meroterpenoids, capitachromenic acids A-M (<b>3</b>-<b>6</b>, <b>7a</b>, <b>7b</b>, <b>8a</b>, <b>8b</b>, <b>9a</b>, <b>9b</b>, <b>10a</b>, <b>10b</b>, and <b>11b</b>), were identified from an ethyl acetate extract of <i>Rhododendron capitatum</i>, using dual high-resolution α-glucosidase and PTP1B inhibition profiling in combination with HPLC-PDA-HRMS-SPE-NMR. In addition, one known chromene meroterpenoid, daurichromenic acid (<b>15</b>), and its biosynthetic precursor, grifolic acid (<b>12</b>), two <i>C</i>-methylated flavanones, (2<i>S</i>)-5,7,4'-trihydroxy-8-methylflavanone (<b>1</b>) and farrerol (<b>2</b>), and two triterpenoids, oleanolic acid (<b>14a</b>) and ursolic acid (<b>14b</b>), were identified. New structures were elucidated by extensive 1D and 2D NMR analysis, and absolute configurations of new chromene meroterpenoids were assigned by analysis of their ECD spectra on the basis of the empirical chromane helicity rule and from Rh<sub>2</sub>(OCOCF<sub>3</sub>)<sub>4</sub>-induced ECD spectra by applying the bulkiness rule. Compounds <b>5</b>, <b>9a</b>, <b>9b</b>, <b>12</b>, and <b>15</b> showed α-glucosidase inhibitory activity with IC<sub>50</sub> values ranging from 8.0 to 93.5 μM, while compounds <b>3</b>, <b>5</b>, <b>8b</b>, <b>9a</b>, <b>9b</b>, <b>10b</b>, <b>11b</b>, <b>12</b>, and <b>15</b> showed PTP1B inhibitory activity with IC<sub>50</sub> values ranging from 2.5 to 68.1 μM.