Appears in the Three Kingdoms-era
《三国志·魏书·鲍勋传》 describing the alliance between Wu and Shu:
吴、
蜀唇齿相依 - 'Wu and Shu are as close as lips and teeth.' Related to
唇亡齿寒 (if the lips perish, the teeth grow cold), which emphasizes the danger when one side falls.