Phloroglucinol-meroterpenoids from the leaves of Eucalyptus camaldulensis Dehnh.

Fourteen undescribed phloroglucinol-meroterpenoids, namely eucalypcamals A-N, were isolated from a CHCl extract of the leaves of Eucalyptus camaldulensis Dehnh. In addition, from the same extract, twelve known phloroglucinols, three known flavonoids, and four known phenolic compounds were also isolated. The structures of the undescribed compounds were analyzed by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and high resolution electrospray ionization mass spectrometry (HRESIMS). The assignments of the absolute configurations were performed by comparing the experimental electronic circular dichroism (ECD) data with the calculated values. Eucalyprobusal E was found to be cytotoxic against HCT116, Jurkat, and MDA-MB-231 cell lines with IC values of 17.6, 9.44, and 17.9 μM, respectively. Eucalrobusone F exhibited antibacterial activity against methicillin-resistant S. aureus (MRSA) and S. aureus with minimum inhibitory concentration/minimum bactericidal concentration (MIC/MBC) values of 4/4 μg/mL while euglobal Ia showed antifungal activity with MIC/MFC values of 16/16 μg/mL.