Bioactive beta-indoloquinazoline Alkaloids from Oricia renieri

Wansi J, Happi EN, Bavoua JLD, Devkota KP, Sewald N. Bioactive beta-indoloquinazoline Alkaloids from Oricia renieri. Planta Medica. 2012;78(01):71-75.Three new beta-indoloquinazoline alkaloids, orirenierine A (1), B (2) and C (4), together with eleven known compounds were isolated from the methanol extract of the stems of Oricia renieri. The structures of all compounds were determined by comprehensive analyses of their spectroscopic data and comparison with literature information. The alkaloids 9-11 were isolated for the first time from this genus. All compounds were tested for their activity against bacteria, fungi, and plant pathogen oomycetes using the paper disk agar diffusion assay. The agar diffusion test gave only low antimicrobial activities, corresponding to MICs > 1 mg/mL. However, compounds 1-4 and 11 exhibited a strong suppressive effect on phagocytosis response upon activation with serum opsonized zymosan in the range of IC(50) = 2.6-6.5 mu M, while low cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3 was observed with IC(50) values ranging from 22.9 to 39.4 mu M

O-Prenylated Acridone Alkaloids from the Stems of Balsamocitrus paniculata (Rutaceae)

Happi EN, Waffo AFK, Wansi JD, Ngadjui BT, Sewald N. O-Prenylated Acridone Alkaloids from the Stems of Balsamocitrus paniculata (Rutaceae). Planta Medica. 2011;77(09):934-938.Two new O-prenylated acridone alkaloids, balsacridone A (1) and B (2), together with eighteen known compounds were isolated from the methanol extract from the stems of Balsamocitrus paniculata, a Cameroonian medicinal plant. The structures of all compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral (EI and ESI) data, and chemical reactions. N-methyl-6-methoxybenzoxazolinone (16) was isolated for the first time from a natural source while compounds 13, 14, and 15 for the first time from this genus. Pure compounds were tested for their activity against bacteria, fungi, and plant pathogen oomycetes, using the paper disk agar diffusion assay. The agar diffusion test delivered low to missing antimicrobial activities, corresponding to MICs > 1 mg/mL. However, compounds 1-15 exhibited a strong suppressive effect on phagocytosis response upon activation with serum opsonized zymosan in the range of IC(50) = 0.5-7.2 mu M, and the acridone alkaloids (1-5), N-trans- p-coumaroyltyramine (13), and N-trans-p-coumaroyloctopamine (14) displayed weak cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3, with IC(50) values ranging from 69.8 to 99.0 mu M

Chemical Constituents of the Bark of Zanthoxylum gilletii (Rutaceae) and Their In Vitro Antiplasmodial and Molecular Docking Studies

The phytochemical investigations of the methanol extract of Zanthoxylum gilletii bark led to the isolation of thirteen compounds identified as two alkaloids including one acridone 5-hydroxynoracronycine (1) and one benzo [c] phenanthridine decarine (2), three lignans trans- and cis-fagaramide (3 and 4) and sesamin (5), two coumarins scoparone (6) and scopoletin (7), three pentacyclic triterpenoids fridelin (8), lupeol (9) and erythrodiol-3-O-palmitate (10), one phenolic compound vanillic acid (11) as well as two common steroids stigmasterol (12), and its derivative stigmasterol-3-O-β-D-glucopyranoside (13). The structures of all the isolated compounds were elucidated by means of their spectroscopic and spectrometric data (1D, 2D-NMR, MS) as well as the comparison of these data with those reported in the literature. Except for compounds 9 and 11–13, all the other isolated compounds are reported for the first time from Z. gilletii but have been already obtained from other Zanthoxylum species and in the Rutaceae family. Compounds 1, 3–5, and 9 were tested in vitro for their antiplasmodial potencies against Plasmodium falciparum 3D7, and the results revealed that all the tested compounds displayed an inhibition between 51.89% and 54.69% while only the mixture of 3 + 4 gave an IC50 lower than 10 000 nM (IC50 = 1333 nM). Furthermore, all the compounds have been evaluated in silico for their ability to inhibit the Plasmodium falciparum dihydroorotate dehydrogenase 5TBO. Sesamin (5) showed the greatest affinity to the antiplasmodium receptor than artemether® and chloroquine®. Further recorded data from their ADMET study, as well as their chemotaxonomy, are also discussed herein. The present study provides further information to enrich the chemistry of Z. gilletii and its qualification as an important source for good candidates in new antiplasmodial drug development

Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco)

Fomani M, Ngeufa Happi E, Nouga Bisoue A, et al. Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco). Bioorganic & Medicinal Chemistry Letters. 2015;26(2):306-309

Tirucallane triterpenoids from the stem bark of Araliopsis synopsis

Happi EN, Tcho AT, Sirri JC, et al. Tirucallane triterpenoids from the stem bark of Araliopsis synopsis. Phytochemistry Letters. 2012;5(3):423-426.Two new tirucallane triterpenoids, 21-methoxy-21,23-epoxy-tirucalla-7,24-dien-3 alpha-ol (1) and 21-methoxy-21,23-epoxy-tirucalla-7,24-diene-1 alpha,3 alpha-diol (2), together with thirteen known compounds were isolated from the CH2Cl2 extract of the stem bark of Araliopsis synopsis. The structures of the compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral (EI and ESI) data and comparison with previously known analogs. Compounds 1-10 were tested against bacteria, fungi and plant pathogen oomycetes by the paper disk agar diffusion assay resulting in missing to low activities corresponding with MICs > 1 mg/mL. However, compounds 5-10 exhibited high cytotoxic activity against the human Caucasian prostate adenocarcinoma cell PC-3 line, with IC50 8.5-12.5 mu M compared to the standard Doxorubicin with IC50 = 0.9 mu M, while compounds 1, 3 and 4 showed low activity. (C) 2012 Published by Elsevier B.V. on behalf of Phytochemical Society of Europe

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

Mesomeric form of quaternary indoloquinazoline alkaloid and other constituents from the Cameroonian Rutaceae Araliopsis soyauxii Engl.

Noulala CGT, Fotso GW, Rennert R, et al. Mesomeric form of quaternary indoloquinazoline alkaloid and other constituents from the Cameroonian Rutaceae Araliopsis soyauxii Engl. BIOCHEMICAL SYSTEMATICS AND ECOLOGY. 2020;91: UNSP 104050.A mesomeric form of quaternary indoloquinazoline alkaloid, soyauxinium chloride (1) was obtained through the chemical investigation of stem bark and roots of Araliopsis soyauxii Engl. [syn. Vepris soyauxii (Engl.) Mziray] (Rutaceae) together with fifteen known compounds, including three furoquinoline alkaloids, three 2-quinolones, two limonoids, two triterpenes, two steroids, a coumarin, an acridone alkaloid, and a flavonoid glycoside. Their structures were established by comprehensive spectroscopic and spectrometric analyses (1D and 2D NMR, ESI-HR-MS) and by comparison with previously reported data. C-13 NMR data of araliopsinine are also reported here for the first time. The isolated compounds were screened in vitro for their effects on the viability of two different human cancer cell lines, namely prostate PC-3 adenocarcinoma cells and colorectal HT-29 adenocarcinoma cells. However, none of the tested compounds exhibited strong anti-proliferative or cytotoxic activities, to either prostate PC-3 cells or colon HT-29 cells. At 100 mu M, the furoquinoline maculine showed a slightly increased anti-proliferative effect, however, exclusively on HT-29 cells. The chemotaxonomic significance of the isolated compounds has also been discussed

Oxidative Burst Inhibitory and Cytotoxic Activity of Constituents of the Fruits of Odyendyea gabonensis

Donkwe SMM, Happi EN, Wansi J, et al. Oxidative Burst Inhibitory and Cytotoxic Activity of Constituents of the Fruits of Odyendyea gabonensis. Planta Medica. 2012;78(18):1949-1956.The methanol extract of dried fruits of Odyendyea gabonensis afforded one new quassinoid [(-)-odyendanol (1)], one new canthin-6-one alkaloid [9-hydroxy-5-methoxycanthin-6-one (4)], and two new steroids [22E, 24R-stigmasta-5,22-diene-3,7-dione (7) and 22E,24R-stigmast-22-ene-3,7-dione (8)] along with fourteen known compounds. The structures of all compounds were established by analyzing the spectroscopic data. The C-13-NMR values of (-)-odyendene (2) and (-)-odyendane (3), as well as the single-crystal X-ray structure of 5-methoxycanthin-6-one (6) are also reported. The oxidative burst inhibitory activity of pure compounds 1-12 was determined by the chemo-luminescence assay, and cytotoxic activities of compounds 2-6 against the human prostate cancer cell PC-3 line were evaluated. Compounds 1-6 exhibited a clear suppressive effect on the phagocytosis response upon activation with serum-opsonized zymosan in the range of IC50 = 0.9-2.0 mu M versus ibuprofen with IC50 = 12.1 mu M, while all canthin-6-one alkaloids (4-6) displayed moderate cytotoxic activity against the human prostate cancer cell PC-3 line, with IC50 values ranging from 13.5-15.4 mu M versus doxorubicine with IC50 = 1.5 mu M

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

Bioactive Phenylethanoids and Coumarines from Basalmocitrus cameroonensis

Wansi J, Bavoua JLD, Happi EN, et al. Bioactive Phenylethanoids and Coumarines from Basalmocitrus cameroonensis. Zeitschrift für Naturforschung B. 2009;64(4):452-458.Two new phenylethanoids, basalethanoid A (1) and B (2), and one new ceramide, basalamide A (3), together with eleven known compounds (4-14) were isolated from the MeOH extract of the stem barks of Basalmocitrus cameroonensis. The structures of all compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral (EI and ESI) data, chemical reactions, and comparison with previously known analogs. Compounds 1, 2, 5, and 7-10 demonstrated a strong inhibition on reactive Oxygen species (ROS) production in the oxidative burst activity of whole blood on activation with serum opsonized zymosan in the range of IC50 = 0.06-12.30 mu g mL(-1)