Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant ICitrus × paradisi/I Macfad

• Published in: Molecules (Basel, Switzerland) Vol. 28; no. 3
• Main Authors: Essombe Malolo, Fanny-Aimée, Kouam, Ariane Dolly Kenmogne, Nyobe, Judith Caroline Ngo, Ngah, Lidwine, Frese, Marcel, Ndom, Jean Claude, Langat, Moses K, Lenta, Bruno Ndjakou, Mulholland, Dulcie A, Sewald, Norbert, Wansi, Jean Duplex
• Format: Journal Article
• Language: English
• Published: MDPI AG 01.01.2023
• Subjects: Alkaloids; Citrus; Citrus fruits; Composition; Coumarins; Diseases and pests; Genetic aspects; Growth; Health aspects; Europe
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28031078

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 (3), furan-2,3-diol (4), 5-methoxyseselin (5), umbelliferone (6), scopoletin (7), citracridone I (8), citracridone II (9), citracridone III (10), limonin (11) and lupeol (12). 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[sub.50] values of 35.2 and 38.1 µg/mL, respectively, compounds 1–7 showed weak activity, with IC[sub.50] values of 99.2 to 250.2 µM and 99.5 to 192.7 µM, respectively.