The present paper investigates the influence of microstructural inhomogeneities of brittle grains on grain crushing in cohesionless, frictional granular materials, using the discrete element method. Macrograins are modelled as assemblies of bonded micrograins of different sizes and bond strengths to simulate crushed sandstone. A method is suggested to incorporate fracture mechanical properties in the model through the selection of bond properties. Normal distribution of bond strengths, as well as degraded bonds are assumed to simulate bond defects. Their effects are first examined through single macrograin crushing tests. Then monotonic oedometer compression tests on macrograin ensembles are simulated for a wide range of pressures and different initial void ratios. The paper also explores the applicability of Bauer's macroscopic compression law to the results of simulations of monotonic, oedometric compression tests. Correlations between the properties of individual macrograins, such as crushing strength and bonding defects, and the properties of the grain ensemble, such as granular hardness and grain size distribution are investigated.