Cannabinoid-like meroterpenoids from Peperomia incana

Author(s)

Hamed, Abdelaaty ; Yamaguchi, Lydia Fumiko ; Morante, Estela Ynes Valencia ; Spira, Beny ; Stammler, Hans Georg ; El Gaafary, Menna ; Ziegler, David ; Syrovets, Tatiana ; Simmet, Thomas ; Kato, Massuo Jorge

• Document type: Journal article
• Source: Phytochemistry; v. 207, p. 12-pg., 2023-01-12.

Abstract

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. (AU)

• FAPESP's process: 14/50316-7 - Dimensions US-Biota São Paulo: Chemically mediated multi-trophic interaction diversity across tropical gradients
• Grantee: Massuo Jorge Kato
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
• FAPESP's process: 19/27661-3 - Bioactive peptides from aquatic Portuguese amphibians
• Grantee: Abdelaaty Hamed Abdelaaty Mona
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 18/07999-7 - VIDA-FROG: valorization of molecules isolated from aquatic Portuguese amphibians
• Grantee: Massuo Jorge Kato
• Support Opportunities: Regular Research Grants