Cannabinoid-like meroterpenoids from Peperomia incana

Hamed A, Yamaguchi LF, Valencia Morante EY, Spira B, Stammler H-G, El Gaafary M, Ziegler D, Syrovets T, Simmet T, Kato MJ (2022)
Phytochemistry.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Autor*in
Hamed, Abdelaaty; Yamaguchi, Lydia Fumiko; Valencia Morante, Estela Ynes; Spira, Beny; Stammler, Hans-GeorgUniBi; El Gaafary, Menna; Ziegler, David; Syrovets, Tatiana; Simmet, Thomas; Kato, Massuo Jorge
Abstract / Bemerkung
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 muM, 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. Copyright © 2022. Published by Elsevier Ltd.
Erscheinungsjahr
2022
Zeitschriftentitel
Phytochemistry
eISSN
1873-3700
Page URI
https://pub.uni-bielefeld.de/record/2967681

Zitieren

Hamed A, Yamaguchi LF, Valencia Morante EY, et al. Cannabinoid-like meroterpenoids from Peperomia incana. Phytochemistry. 2022.
Hamed, A., Yamaguchi, L. F., Valencia Morante, E. Y., Spira, B., Stammler, H. - G., El Gaafary, M., Ziegler, D., et al. (2022). Cannabinoid-like meroterpenoids from Peperomia incana. Phytochemistry. https://doi.org/10.1016/j.phytochem.2022.113551
Hamed, Abdelaaty, Yamaguchi, Lydia Fumiko, Valencia Morante, Estela Ynes, Spira, Beny, Stammler, Hans-Georg, El Gaafary, Menna, Ziegler, David, Syrovets, Tatiana, Simmet, Thomas, and Kato, Massuo Jorge. 2022. “Cannabinoid-like meroterpenoids from Peperomia incana”. Phytochemistry.
Hamed, A., Yamaguchi, L. F., Valencia Morante, E. Y., Spira, B., Stammler, H. - G., El Gaafary, M., Ziegler, D., Syrovets, T., Simmet, T., and Kato, M. J. (2022). Cannabinoid-like meroterpenoids from Peperomia incana. Phytochemistry.
Hamed, A., et al., 2022. Cannabinoid-like meroterpenoids from Peperomia incana. Phytochemistry.
A. Hamed, et al., “Cannabinoid-like meroterpenoids from Peperomia incana”, Phytochemistry, 2022.
Hamed, A., Yamaguchi, L.F., Valencia Morante, E.Y., Spira, B., Stammler, H.-G., El Gaafary, M., Ziegler, D., Syrovets, T., Simmet, T., Kato, M.J.: Cannabinoid-like meroterpenoids from Peperomia incana. Phytochemistry. (2022).
Hamed, Abdelaaty, Yamaguchi, Lydia Fumiko, Valencia Morante, Estela Ynes, Spira, Beny, Stammler, Hans-Georg, El Gaafary, Menna, Ziegler, David, Syrovets, Tatiana, Simmet, Thomas, and Kato, Massuo Jorge. “Cannabinoid-like meroterpenoids from Peperomia incana”. Phytochemistry (2022).
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