A rotameric tryptamide alkaloid from the roots of Vepris lecomteana (Pierre) Cheek & T. Heller (Rutaceae)

Kouam ADK, Kenmogne SB, Lobe JS, et al. A rotameric tryptamide alkaloid from the roots of Vepris lecomteana (Pierre) Cheek & T. Heller (Rutaceae). FITOTERAPIA. 2019;135:9-14.A rotameric tryptamide alkaloid (1a-1b) was isolated from the methanolic extract of the roots of Vepris lecomteana together with the known compounds anhydroevoxine (2), lecomtequinoline C (3), evoxine (4), N-methylflindersine (5), evoxanthine (6), hesperidin, lupeol, beta-sitosterol and stigmasterol. The previously not reported 7-(3-anilino-2-hydroxyprenyloxy)-8-methoxydictamine (2a) was obtained by opening the epoxide of anhydroevoxine (2). The structures of above compounds were determined by comprehensive spectroscopic analyses of 1D and 2D NMR, EI-/ESI-MS, X-ray crystallography and comparison with the reported data. At room temperature, H-1 and C-13 NMR spectra show two rotamers (1a and 1b) with integrated intensities of 2/3, whereas at around 60 degrees C, only the 1b conformer was observed. Furthermore, the crystal structure of 1 was determined by the direct method of single crystal X-ray diffraction. The suggested biosynthesis for the formation of the new rotameric tryptamide alkaloid 1 is presented. Some of the isolated compounds (1, 2 and 2a) were tested in vitro against bacteria, resulting in weak for (1 and 2) to moderate activity for (2a) against Micrococcus Mulls and Escherichia coli with MIC values of 15.3 and 15.3 mu g/mL, respectively

Antimicrobial Furoquinoline Alkaloids from Vepris lecomteana (Pierre) Cheek & T. Heller (Rutaceae)

Three new prenylated furoquinoline alkaloids named lecomtequinoline A (1), B (2), and C (3), together with the known compounds anhydroevoxine (4), evoxine (5), dictamnine (6), N-methylflindersine (7), evoxanthine (8), hesperidin, lupeol, β-sitosterol, stigmasterol, β-sitosterol-3-O-β-d-glucopyranoside, stearic acid, and myristyl alcohol, were isolated by bioassay-guided fractionation of the methanolic extracts of leaves and stem of Vepris lecomteana. The structures of compounds were determined by spectroscopic methods (NMR, MS, UV, and IR) and by comparison with previously reported data. Crude extracts of leaves and stem displayed high antimicrobial activity, with Minimum Inhibitory Concentration (MIC) (values of 10.1–16.5 and 10.2–20.5 µg/mL, respectively, against Escherichia coli, Bacillus subtilis, Pseudomonas agarici, Micrococcus luteus, and Staphylococcus warneri, while compounds 1–6 showed values ranging from 11.1 to 18.7 µg/mL or were inactive, suggesting synergistic effect. The extracts may find application in crude drug preparations in Western Africa where Vepris lecomteana is endemic, subject to negative toxicity results in vivo

A New Aromatic Amide from the Roots of Zanthoxylum tessmannii (Rutaceae).

Kenmoe Djeukeu C, Kouam Kenmogne A, Guy Blaise Azebaze A, et al. A New Aromatic Amide from the Roots of Zanthoxylum tessmannii (Rutaceae). Chemistry & biodiversity. 2019;16(4):e1800590.Phytochemical investigation of the methanolic extract of the roots of Zanthoxylum tessmannii Zepernick and Timler (Rutaceae) led to the isolation and characterization of one new aromatic amide named tessmamide (1) along with twelve known compounds, N-benzoyltyramine methyl ether (2), 7,8,9-trimethoxycoumarin (3), 7,8-dimethoxycoumarin (4), integrifoliodiol (5), robustin (6), skimmianine (7), lupeol (8), lupenone (9), a mixture of stigmasterol and beta-sitosterol, and a mixture of their glucosides. The structures of all compounds were determined by comprehensive spectroscopic analyses (1D- and 2D-NMR, EI-MS, and ESI-MS) and comparison with known analogs. The determination of the radical scavenging activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay gave moderate antioxidant values for the crude extracts of the roots of Zanthoxylum tessmannii (IC50 0.8 mg/mL), tessmamide (1; IC50 31.8 mum), and 7,8,9-trimethoxycoumarin (3; IC50 29.3 mum), compared to the standard ascorbic acid (IC50 11.6 mum). © 2019 Wiley-VHCA AG, Zurich, Switzerland

Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant Citrus × paradisi Macfad (Rutaceae)

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 IC50 values of 35.2 and 38.1 µg/mL, respectively, compounds 1–7 showed weak activity, with IC50 values of 99.2 to 250.2 µM and 99.5 to 192.7 µM, respectively

Chemical Constituents of the Stem Bark of the Hybrid Plant Citrus * paradisi Macfad. (Rutaceae)

Essombe Malolo F-A, Bellier Tabekoueng G, Dongmo Tekapi Tsopgni W, et al. Chemical Constituents of the Stem Bark of the Hybrid Plant Citrus * paradisi Macfad. (Rutaceae). Chemistry & biodiversity. 2022: e202101033.The stem bark of Citrus * paradisi Macfad. (Rutaceae) gave (23S)-isolimonexic acid (1), limonin (2), citracridone II (3), citpressine II (4), citpressine I (5), grandisine (6), 2-hydroxynoracronycine (7), citracridone I (8), 5-methoxyseselin (9), umbelliferone (10), scopoletin (11), naringenin (12), apigenin (13), friedelin (14), agrostophyllinone (15) and stigmasterol-3-O-beta-D-glucopyranoside (16). The structures of the compounds were determined using NMR and MS spectroscopic data, and by comparison with published data. The relative configuration of 1 was proposed as (23S)-isolimonexic acid using NOE studies. Hydrogenation reaction of compound 3 led to the new derivative 3',4'-dihydrocitracridone II (3a). Cytotoxicity activities against the human adenocarcinoma alveolar basal epithelial cell lines A549 and the Caucasian prostate adenocarcinoma cell lines PC3, using the MTT assays showed that the methanol crude extract was significant with IC50 values of 30.1 and 31.7 mug/mL, respectively, with the positive control, doxorubicin giving an IC50 of 0.9 muM. In addition, compounds 3, 7 and 8 gave moderate cytotoxic activities with IC50 values of 33.1, 31.2 and 32.5 muM for A549 cells and 35.7, 33.8 and 34.9 muM for PC3 cells, respectively. The hydrogenated 3a was less active than 3, suggesting that the presence of the double bond in pyrans is important for structure-activity relationship. © 2022 Wiley-VHCA AG, Zurich, Switzerland