Coumarinolignoid and indole alkaloids from the roots of the hybrid plant citrus × paradisi Macfad (Rutaceae) Fanny-Aimée Essombe Malolo 1 , Ariane Dolly Kenmogne Kouam 1 , Judith Caroline Ngo Nyobe 2 , Lidwine Ngah 2 , Marcel Frese 3 , Jean Claude Ndom 1 , Moses K. Langat 4 , Bruno Ndjakou Lenta 3,5, Dulcie A. Mulholland 6 , Norbert Sewald 3 ,*Jean Duplex Wansi 1,3, * 1 Department of Chemistry, Faculty of Sciences, University of Douala, Cameroon, 2 Department of Pharmaceutical Sciences, Faculty of Medicine and Pharmaceutical Sciences, University of Douala, Cameroon, 3 Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Germany, 4 Royal Botanic Gardens, Kew, UK, 5 Department of Chemistry, Higher Teacher Training College, University of Yaoundé 1, Cameroon, 6 Natural Products Research Group, Department of Chemistry, University of Surrey, UK A phytochemical investigation of the roots of Citrus × paradisi Macfad. (Rutaceae) led to the isolation of two new compounds, namely 1-formyl-5-hydroxy-N-methylindolin-1-ium (1)and decyloxycleomiscosin D (2), along with ten known compounds: 1,1-dimethylpyrrolidin-1-ium-2-carboxylate (4), furan-2,3-diol (4), 5-methoxyseselin(5), umbelliferone (5), scopoletin (5), citracridone I(5), citracridone II (5), limonin (5), citracridone III (6) and lupeol (7). The structures were determined through the comprehensive spectroscopic analysis of 1D and 2D NMR and EI- and ESI-MS, as well as a comparison with the published data. Notably, compounds 3 and 4 from the genus Citrus are reported here for the first time. In addition, the MeOH extract of the roots and compounds 1–7 were screened against the human adenocarcinoma alveolar basal epithelial cell line A549 and the Caucasian prostate adenocarcinoma cell line PC3 using the MTT assay. While the extract showed significant activity, with IC 50 values of 35.2 and 38.1 µg/mL, respectively, compounds 1–7 showed weak activity, with IC 50 values of 99.2 to 250.2 µM and 99.5 to 192.7 µM, respectively. References 1. Nicolosi, E.; Deng, Z.N.; Gentile, A.; La Malfa, S.; Continella, G.; Tribulato, E. Citrus phylogeny and genetic origin of important species as investigated by molecular markers. Theor. Appl. Genet. 2000, 100, 1155–1166. 2. Gmitter, F.G., Jr. Origin, evolution, and breeding of the grapefruit. Plant Breed. Rev. 1995, 13, 345–363. 3. Adeneye, A.A. Hypoglycemic and hypolipidemic effects of methanol seed extract of Citrus paradisi M acfad (Rutaceae) in alloxan-induced diabetic Wistar rats. Nig. Q. J. Hosp. Med. 2008, 18, 211–215. 4. Dibong, S.; Mpondo Mpondo, E.; Ngoye, A.; Kwin, M.; Betti, J. Ethnobotanique et phytomédecine des plantes médicinales de Douala, Cameroun. J. Appl. Sci. 2011, 37, 2496–2507. 5. Malolo, F.-A.E.; Tabekoueng, G.B.; Tsopgni, W.D.T.; Chimeze, V.W.N.; Kouam, A.K.; Mas-Claret, E.; Langat, M.K.; Ndom, J.C.;Frese, M.; Sewald, N.; et al. Chemical constituents of the stem bark of the hybrid plant Citrus × paradisi Macfad. (Rutaceae). Chem.Biodivers. 2022, 19, e202101033. 6. Ahmad, V.U.; Basha, A.; Atta-ur-Rahman. Identification and C-13 NMR spectrum of stachydrine from Cadaba fruticosa. Phytochemistry 1975, 14, 292–293. 7. Fomani, M.; Ngeufa, E.H.; Nouga, A.B.; Ndom, J.C.; Kamdem, A.F.W.; Sewald, N.; Wansi, J.D. Oxidative burst inhibition,cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulata (Blanco). Bioorg. Med. Chem. Lett. 2016, 26, 306–309.
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