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

Acridone Alkaloids and Coumarins from the Stem Bark of Citropsis articulata (Rutaceae)

Meva'a LM, Songue JL, Wansi J, et al. Acridone Alkaloids and Coumarins from the Stem Bark of Citropsis articulata (Rutaceae). Zeitschrift für Naturforschung B. 2010;65(4):525-527.A new acridone alkaloid, citropsine A (1), and thirteen known compounds (2-14) were isolated from the MeOH extract of the stem bark of Citropsis articulata. Structures of all compounds were determined by detailed analyses of their ID and 2D NMR spectra, mass spectrometric data and by comparison with previously known analogs

Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta

Ekon JPL, Bissoue AN, Fomani M, et al. Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta. Zeitschrift für Naturforschung B. 2015;70(11):837-842.Two new 24-nor-ursane-type triterpenoids, 2 alpha, 3 beta, 19 alpha-trihydroxy-24-norurs-4(23), 12-dien-28-oic acid (1) and 3 beta-acetoxy-2 alpha, 19 alpha-dihydroxy-24-norurs-4(23), 12-dien-28-oic acid (2), along with 15 known compounds were isolated from the methanol extract of the twigs of Mostuea hirsuta. While 2-hydroxymethylbenzamide (13) was isolated for the first time from the natural source, compounds 3-12 are reported here for the first time from the genus Mostuea. Their structures were elucidated by means of spectroscopic analyses including 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometric data as well as comparison with data from the literature. Compounds 1, 2, 4-9 and 13 were tested against bacteria, fungi and plant pathogen oomycetes by the paper disk agar diffusion assay resulting in missing to low activities corresponding with minimum inhibitory concentrations (MICs) > 1 mg mL(-1). However, the respective compounds 1, 2, 8, 9 and 13 exhibited moderate cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3, with IC50 10.6-16.5 mu m compared to the standard doxorubicin with IC50 0.9 mu m

The chemical constituents of <i>Penianthus longifolius</i> Miers

Fourteen compounds were isolated from the roots, leaves and twigs of Penianthus longifolius Miers (Menispermaceae), including two previously unreported neo-clerodane diterpenoids, penianthin (1), its C-8 epimer (2). In addition, the previously reported O-methylmoschatoline (3), taraxerol (4), taraxerone (5), rubrosterone, (6), panuosterone (7), 22-epi-20-hydroxyecdysone (8), ergosterol peroxide (9), stigmast-5-ene-3,7-dione (10), stigmasterol (11), β-sitosterol (12), stigmasterol glucoside (13) and β-sitosterol glucoside (14) were isolated. The structures of the compounds were determined by means of NMR spectroscopic and mass spectrometric analysis. The absolute configurations of 1 and 2 were determined by circular dichroism analysis. Compounds 1 and 2 were screened against the NCI60 cancer cell panel but showed no significant activity at 10 μM

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 &amp; 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 constituents from Flacourtia vogelii Hook.f. (Flacourtiaceae)

Tsopgni WDT, Ehawa Essoung FR, Makam Kuetche P, et al. Bioactive constituents from Flacourtia vogelii Hook.f. (Flacourtiaceae). Natural Product Research . 2023.The chemical investigation of the methanolic root extract of Flacourtia vogelii led to the isolation of a new arylbenzoate derivative, vogelinal (1), together with thirteen known compounds (2-14). The structures of the isolates were elucidated by extensive spectroscopic and spectrometric analyses (1D and 2D NMR, ESI-MS) and by comparison with previously reported data. All the compounds were tested for their antioxidant, antifungal and antibacterial activities. Compound 7 exhibited the highest antioxidant potential, with RSa50of 11.80±2.13g/mL, RSa50of 42.60±6.32g/mL and RC50 of 51.60±7.71g/mL for the DPPH, ABTS and FRAP assay, respectively. Compound 13 displayed weak antifungal effect with MIC value of 125mug/mL against Candida parapsilosis. Compound 8 showed weak antibacterial effect with MIC value of 125mug/mL, against Shigella dysenteria. The present study, conclude that this species could be a promising source of antioxidant and antibacterial constituents

New anthraquinone derivatives from the stem barks of Morinda lucida Benth

Ekon JPL, Zra T, Songue JL, et al. New anthraquinone derivatives from the stem barks of Morinda lucida Benth. Phytochemistry Letters. 2020;39:94-98.Three new anthraquinone derivatives including (2S, 3R)-1,2,3,4-tetrahydro-2,3,6-trihydroxy-2-methylan-thracene-9,10-dione (1), 3,6-dihydroxy-1,2-dimethoxyanthraquinone (2) and 1,6-dihydroxy-2-hydroxymethyl5-methoxyanthraquinone (3) together with thirteen known compounds including eleven anthraquinones and two triterpenes were isolated from the methanolic crude extract of the stem barks of Morinda lucida. The structures of the new compounds were unambiguously elucidated on the basis of modern NMR spectroscopic methods, as well as by high-resolution mass spectrometry. The known compounds were identified on the basis of their spectral characteristics and by comparison with literature data. The antimicrobial activities of (2S, 3R)1,2,3,4-tetrahydro-2,3,6-trihydroxy-2-methylanthracene-9,10-dione (1), the methanolic crude extract and its fractions were evaluated against five bacteria and four fungi. The lowest values of the MIC (256 mu g/mL) were recorded on Candida parapsilosis, Cryptococcus neoformans for the methanolic crude extract and on Salmonella typhi for the ethyl acetate fraction

Acridone alkaloids from Vepris verdoorniana (Excell & Mendonca) Mziray (Rutaceae)

Atangana AF, Toze FAA, Langat MK, et al. Acridone alkaloids from Vepris verdoorniana (Excell &amp; Mendonca) Mziray (Rutaceae). Phytochemistry Letters. 2017;19:191-195.Two new acridone alkaloids, verdoocridone A (1) and B (4), together with fifteen known compounds were isolated from methanol extracts of the roots and leaves of Vepris verdoorniana. The structures of all compounds were determined by comprehensive spectroscopic analyses (1D and 2D NMR, EI-and ESIMS). The C-13 NMR values of 1,2,3,5-tetramethoxy-N-methylacridone (2) and 5-methoxyaborinine (3) are also reported. The crude extracts and compounds (1-6) were tested for their antimicrobial activity. The test delivered moderate activities for crude extracts and compounds 1, 5 and 6 against the bacterium Staphylococcus aureus and the fungi Mucor meihei and Candida albicans with MIC values between 115 and 180 mu g/mL for extracts and between 21.3 and 29.4 mu M for compounds, compared to gentamycin with 0.2 mu M and nystatin with 5.2 mu M against both fungi. The determination of the radical scanvenging activity using 1,1-dephenyl-2-picrylhydrazyl (DPPH) assay gave moderate antioxidant values for all tested compounds, with IC50 between 0.29 and 0.41 mu M, compared to the standard 3-t-butyl-4hydroxyanisole (BHA) displaying 0.03 mu M. (C) 2017 Phytochemical Society of Europe. Published by Elsevier Ltd. All rights reserved

First report of compounds from an Ancistrocarpus species: Triterpenoids from A. densispinosus Oliv. (Malvaceae).

Peyeino JH, Djomkam HLM, Kenmogne SB, et al. First report of compounds from an Ancistrocarpus species: Triterpenoids from A. densispinosus Oliv. (Malvaceae). Natural product research. 2020.The stem bark of Ancistrocarpus densispinosus Oliv. exhibited triterpenoids, including the rare fernane-type, fern-9(11)-ene-2alpha,3beta-diol (1) a possible chemotaxonomically distinct biomolecule for the genus. Other triterpenoids that were isolated from this plant include the ursane-type ursolic acid (2) and corosolic acid (3), friedelane-type friedelin (4) and canophyllol (5), lupane-type lupeol (6), betulin (7), betulinic acid (8) and hennadiol (9), oleanoic acid (10), maslinic acid (11) and taraxerol (12) and three sterols. This is the first report of the chemistry of a plant of the Ancistrocarpus. The structures of the compounds were elucidated based on their NMR, IR and MS techniques and by comparisons of their experimental data with those reported. The twelve triterpenoids 1-12 were found to be inactive against five bacterial strains Escherichia coli, Bacillus subtilis, Pseudomonas agarici, Micrococcus luteus and Staphylococcus warneri; inactive against KB-3-1 cervix carcinoma cancer cell line and inactive as antioxidants in the DPPH assay