Cannabinoid-like meroterpenoids from Peperomia incana

Ten previously undescribed metabolites were isolated from Peperomia incana (Haw.) A. Dietr. (Piperaceae), among which four contained a chromene moiety, two were identified as meroterpene lactones, and four were cannabinoid-like compounds. While the chemical structures of the compounds were assigned based on HRESIMS and 1D and 2D-NMR spectra analyses, the relative and absolute configurations were assigned from NOE correlations and a combination of ECD data and X-ray single crystal analyses, respectively. In a cytotoxic assay against a panel of seven human cancer cell lines (A549, MDA-MB-231, HeLa, DU 145, 5637, Hep G2, and MIA PaCa-2, which represent non-small cell lung cancer, as well as breast, cervical, prostate, bladder, liver, and pancreas carcinomas, respectively) most of the isolated compounds showed promising cytotoxic activities. The incanachromenes B, and incanabinoids A and C exhibited the highest cytotoxicity toward all tested cancer cell lines with IC50 values in the range of 5.0-10.0 & mu;M, whereas incanolides A, B, and incanabinoid B showed the lowest cytotoxic activity. In addition, incanachromene C and incanabinoid C produced a significant antibacterial effect toward planktonic cells and biofilms of multidrug-resistant Staphylococcus aureus strains.

Automated summary

Ten new metabolites were discovered in Peperomia incana, including chromene-containing compounds, meroterpene lactones, and cannabinoid-like compounds. Their chemical structures were determined using various spectroscopic methods, and their cytotoxic activity against seven human cancer cell lines was evaluated. Some of the compounds showed promising cytotoxicity, with incanachromenes B and incanabinoids A and C exhibiting the highest activity. In addition, incanachromene C and incanabinoid C showed significant antibacterial effects against multidrug-resistant Staphylococcus aureus strains.