Meroterpenoids from the leaves of Psidium guajava (guava) cultivated in Korea using MS/MS-based molecular networking

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.

Automated summary

MS/MS-based molecular networking revealed differences in chemical profiles of Psidium guajava grown in Jeju Island, Vietnam, and China, particularly in the terpenoid-coupled-phloroglucinol clusters. A chemical investigation of the 95% EtOH extract of Jejuguava leaves led to the discovery of new meroterpenoids named jejuguajavones A-J, with some compounds exhibiting inhibitory activity against the protein tyrosine phosphatase 1B (PTP1B) enzyme.