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MS/MS-based molecular networking showed differences in the chemical profiles, especially the terpenoid-coupled-phloroglucinol clusters, of Psidium guajava grown in Jeju Island of South Korea ("Jejuguava"), Vietnam and China. A chemical investigation of the 95% EtOH extract of Jejuguava leaves revealed meroterpenoids characterized by a dihydropyran ring junction between an acylphloroglucinol structure and terpenoid, and named jejuguajavones A–J (1 – 10). Compounds (±)- 8 –(±)- 10 are racemic mixtures that were separated using a chiral HPLC column. The chemical structures of all the isolated compounds (1 – 10) were determined by analyzing the spectroscopic data and performing electronic circular dichroism calculations. Among the isolates, compounds 1 – 4 exhibit inhibitory activity against the protein tyrosine phosphatase 1B (PTP1B) enzyme, and this result was confirmed by molecular docking simulations. [Display omitted] • Ten Psidium meroterpenoids were isolated from P. guajava grown in Jeju Island, Korea. • PTP1B inhibitory activity of all isolates and molecular docking were analysed. • Ecological and adaptive variations in plants also affect their chemical composition. [ABSTRACT FROM AUTHOR]