Cannabinoid-like meroterpenoids from Peperomia incana

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

doi:10.1016/j.phytochem.2022.113551

Cannabinoid-like meroterpenoids from Peperomia incana

Phytochemistry. 2023 Mar:207:113551. doi: 10.1016/j.phytochem.2022.113551. Epub 2022 Dec 9.

Affiliations

¹ Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City-Cairo, 11884, Egypt; Institute of Chemistry, University of São Paulo, Av.Prof.Lineu Prestes, 748, São Paulo, 05508-000, SP, Brazil.
² Institute of Chemistry, University of São Paulo, Av.Prof.Lineu Prestes, 748, São Paulo, 05508-000, SP, Brazil.
³ Institute of Biomedical Sciences, University of São Paulo, Av.Prof.Lineu Prestes, 2415, São Paulo, 05508-000, SP, Brazil.
⁴ Inorganic and Structural Chemistry, Bielefeld University, Department of Chemistry, D-33501, Bielefeld, Germany.
⁵ Department of Pharmacognosy, College of Pharmacy, Cairo University, Cairo, 11562, Egypt; Institute of Pharmacology of Natural Products and Clinical Pharmacology, Ulm University, Ulm, D-89081, Germany.
⁶ Institute of Pharmacology of Natural Products and Clinical Pharmacology, Ulm University, Ulm, D-89081, Germany.
⁷ Institute of Chemistry, University of São Paulo, Av.Prof.Lineu Prestes, 748, São Paulo, 05508-000, SP, Brazil. Electronic address: majokato@iq.usp.br.

PMID: 36509184
DOI: 10.1016/j.phytochem.2022.113551

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 μM, 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.

Keywords: Antibacterial activity; Cytotoxicity; Incanabinoids; Meroterpenes chromenes; Peperomia incana; Piperaceae; Structural elucidation.

MeSH terms

Antineoplastic Agents* / pharmacology
Cannabinoids*
Carcinoma, Non-Small-Cell Lung*
Humans
Lung Neoplasms*
Methicillin-Resistant Staphylococcus aureus*
Molecular Structure
Peperomia* / chemistry

Substances

Cannabinoids
Antineoplastic Agents