RESUMEN
A study of diterpenoids as active ingredients against cancer from the active roots extract of Casearia barteri Mast. (IC50 = 1.57 µg mL-1) led to the isolation of six new clerodane diterpenoids, named as barterins A-F (1-6) alongside seven known compounds, caseamembrin A, caseamembrin E, casearlucin A, graveospene G, N-trans-feruloyltyramine, N-cis-feruloytyramine and sitosterol-3-O-ß-D-(6-O-palmitoyl)-glucopyranoside. Their structures were elucidated based on NMR spectroscopic data and mass spectrometry. The absolute configurations of 1-6 were established by the time-dependent density functional theory (TDDFT), electronic circular dichroism (ECD) calculations and experimental data analysis. The cytotoxic effects of compounds 1-6 were evaluated against a human cervix carcinoma cell line KB-3-1. Barterins A-D (1-4) showed cytotoxic effects against the KB-3-1 cell line with IC50 values ranging from 1.34-4.73 µM.
RESUMEN
The chemical investigation of the methanol extract of the roots of Caloncoba lophocarpa (Oliv.) Gilg. exhibited a new 30-norfriedelane triterpenoid, laphocarpanol (1), together with seven known compounds, caloncobalactone (2), friedelin (3), friedelanol (4), asperphernamate (5), stigmasterol (6), sitosterol (7) and sitosterol-3-O-ß-D-glucopyranoside (8). The structures of the compounds 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 antifungal and antibacterial activities. Compound 1 displayed weak antibacterial effect with MIC value of 62.5 µg/mL against Shigella flexineri. All the isolates were found to be inactive against the tested fungal strains.
RESUMEN
Two new 30-norfriedelane triterpenoids namely glaucalactone C (1) and glaucanoic acid (2) along with sixteen known compounds (3-18) have been isolated from the methanolic extracts of the stem bark and fruits of Caloncoba glauca (P.Beauv.) Gilg (Achariaceae). The structures of all the isolated compounds have been established with the aid of their extensive spectroscopic analyses (1D and 2D-NMR) as well as mass spectrometry. Six compounds (1-5, 9) were screened for antiplasmodial activity against two strains P. falciparum Dd2 and P. falciparum 3D7. The results showed that glaucanoic acid (2) was the most active one with IC50 values of (3.5 ± 0.1 µg/mL) and (4.6 ± 0.7 µg/mL) against PfDd2 and Pf3D7, respectively, while glaucalactone C (1) moderately inhibited PfDd2 (9.4 ± 0.1 µg/mL) and weakly Pf3D7 (15.9 ± 2.3 µg/mL). The molecular docking analyses of the isolated compounds showed that compounds 1-4 and 9-11 are potential drug targets and were further supported by their ADMET studies that revealed welwitschiilactones B and C (4 and 5) as well as ß-sitosterol (10) as the most qualified compounds to be safe as drugs. The results indicate that C. glauca is an important source of good candidates in new antiplasmodial drug development.
Asunto(s)
Antimaláricos , Malpighiales , Antimaláricos/farmacología , Antimaláricos/química , Extractos Vegetales/química , Frutas , Simulación del Acoplamiento Molecular , Corteza de la Planta/química , Estructura Molecular , Plasmodium falciparum , Relación Estructura-ActividadRESUMEN
In Cameroon, malaria is still the cause of several deaths yearly and leading to the continued search for new potent leads to fight against Plasmodium falciparum. Medicinal plants like Hypericum lanceolatum Lam. are introduced in local preparations for the treatment of affected people. The bioassay-guided fractionation of the crude extract of the twigs and stem bark of H. lanceolatum Lam. led to the identification of the dichloromethane-soluble fraction as the most active (with 32.6% of the parasite P. falciparum 3D7 survival) which was further purified by successive column chromatography to obtain four compounds identified by their spectrometric data as two xanthones 1,6-dihydroxyxanthone (1) and norathyriol (2) and two triterpenes betulinic acid (3) and ursolic acid (4). In the antiplasmodial assay against P. falciparum 3D7, the triterpenoids 3 and 4 displayed the most significant potencies with IC50 values of 2.8 ± 0.8 µg/mL and 11.8 ± 3.2 µg/mL, respectively. Furthermore, both compounds were also the most cytotoxic against P388 cell lines with IC50 values of 6.8 ± 2.2 µg/mL and 2.5 ± 0.6 µg/mL, respectively. Further insights on the inhibition method of the bioactive compounds and their drug-likeness were obtained from their molecular docking and ADMET studies. The results obtained help in identifying additional antiplasmodial agents from H. lanceolatum and support its use in folk medicine for the treatment of malaria. The plant might be considered as a promising source of new antiplasmodial candidates in new drug discovery.
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Antimaláricos , Clusiaceae , Hypericum , Malaria Falciparum , Malaria , Triterpenos , Humanos , Antimaláricos/química , Hypericum/química , Extractos Vegetales/química , Simulación del Acoplamiento Molecular , Malaria/parasitología , Triterpenos/farmacología , Plasmodium falciparum , Malaria Falciparum/tratamiento farmacológico , BioensayoRESUMEN
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.
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Adenocarcinoma , Citrus paradisi , Citrus , Rutaceae , Masculino , Humanos , Rutaceae/química , Extractos Vegetales/química , Alcaloides Indólicos/análisis , Raíces de Plantas/química , Estructura MolecularRESUMEN
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 ± 2.13 µg/mL, RSa50of 42.60 ± 6.32 µg/mL and RC50 of 51.60 ± 7.71 µg/mL for the DPPH, ABTS and FRAP assay, respectively. Compound 13 displayed weak antifungal effect with MIC value of 125 µg/mL against Candida parapsilosis. Compound 8 showed weak antibacterial effect with MIC value of 125 µg/mL, against Shigella dysenteria. The present study, conclude that this species could be a promising source of antioxidant and antibacterial constituents.
Asunto(s)
Flacourtia , Salicaceae , Antioxidantes/química , Antifúngicos/farmacología , Antifúngicos/química , Salicaceae/química , Antibacterianos/química , Extractos Vegetales/farmacología , Extractos Vegetales/químicaRESUMEN
Phytochemical investigation of the aerial roots of Ficus sur, a Cameroonian medicinal plant, resulted in a previously undescribed cerebroside, suroside (1), in addition to its aglycon congener suramide (2). Moreover, six known natural products including alpinumisoflavone (3), wighteone metabolite (4), oleanolic acid (5), ß-sitosterol (6), ß-sitosterol-3-O-ß-D-glucopyranoside (7), and epi-ѱ-taraxastanolone (8) were identified. The structures of the previously undescribed compounds were determined by analysis of 1D and 2D-NMR (One and two dimensional nuclear magnetic resonance), mass spectrometry, chemical conversion, and by comparison of these data with those from the literature. Wighteone metabolite (4) exhibited a weak cytotoxic activity against the human HepG2 hepatocellular carcinoma cells with an IC50 value of 51.9 µM.
Asunto(s)
Ficus , Plantas Medicinales , Humanos , Ficus/química , Plantas Medicinales/química , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Cerebrósidos , Extractos Vegetales/farmacologíaRESUMEN
Phytochemical investigation of the methanolic extract of the trunk bark of Caloncoba welwitschii (Oliv.) Gilg (Achariaceae) led to the isolation of four new compounds, including three new 30-norfriedelane triterpenes, welwitschiilactones D-F (1-3), one new friedelane triterpene, welwitschioic acid (4) as well as ten known compounds: stigmastane-3,6-dione (7), a mixture of ß-sitosterol and stigmasterol (6a and 6b), a mixture of ß-sitosterol and stigmasterol glucoside (11a and 11b), (2S,3S,4R,5R)-N-(1,3,4,5-tetrahydroxyndecan-2-yl)tetradecanamide (10), 1-O-ß-D-glucopyranosyl-(2S,3R,8E)-2-[(2'R)-2-hydroxylpalmitoylamino]-8-octadecene-1,3-diol (12), 3ß,21ß-dihydroxy-27-oxo-30-nor-(D:A)-friedo-olean-20(29))en-27,19α-lactone (8), 21ß-hydroxy-3,27-dioxo-30-nor-(D:A)-friedo-olean-20(29)-en-27,19α-lactone (9) and 2ß,21ß-dihydroxy-27-oxo-30-nor-(D:A)-friedo-olean-20(29)-en-27,19α-lactone (5). The structures of all the isolated compounds were determined by extensive spectroscopic analyses (1D and 2D NMR as well as ESI-MS). The relative configuration of the 20-oxymethine in 1 as well as that of 19-oxymethine in 2 and 3 has been established using the NOESY spectrum. In an experiment, a sample of welwitschiilactone C (5) was chemically modified through reduction reaction to give a new hemi-synthetic derivative namely 2ß,3ß,21ß-trihydroxy-30-nor-(D:A)-friedo-olean-20(29)-en-27,19α-lactone (5a).
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Malpighiales , Triterpenos , Corteza de la Planta/química , Triterpenos/química , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
The triterpenes represent one of the most reported subclasses of specialized metabolites from the plant kingdom. They play a key role in the protection of plants and their metabolism in addition to displaying a high structural diversity and large scale of biological activities. The scaffold can undergo several reactions like oxidation or substitution at different positions of the skeleton leading to the formation of several types of compounds. More specifically, triterpene dimer is a small group of compounds found in nature (from plants precisely). Until 2021, the chemical and pharmacological works reported in the literature indicated the identification of 90 natural dimeric triterpenes and 11 synthetic derivatives from 19 plants species and very few of them have been biologically evaluated for their antibacterial, antioxidant, antiproliferative or molluscicide activities. This review aims to compile the literature on the occurrence, chemistry and biological activities of the triterpenoid dimers. To attend this goal, a literature survey has been done in a number of online libraries including Scifinder, PubMed, Web of Science and Google Scholar using keywords terpene, triterpene, dimer, celastroloid without language restriction. This paper provides the easiest access to the information on triterpene dimers for readers and researchers in view to enhancing the continuity of research works on this topic.
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Triterpenos , Antibacterianos/metabolismo , Antibacterianos/farmacología , Plantas/química , Triterpenos/químicaRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Malaria remains one of the greatest threats to human life especially in the tropical and sub-tropical regions where it claims hundreds of thousands of lives of young children every year. Meliaceae represent a large family of trees and shrubs, which are widely used in African traditional medicine for the treatment of several ailments including fever due to malaria. The in vitro and in vivo antiplasmodial as well as insecticidal investigations of their extracts or isolated compounds have led to promising results but to the best of our knowledge, no specific review on the traditional uses, phytochemistry of the antiplasmodial, insecticidal and cytotoxic lead compounds and extracts of Meliaceae plants has been compiled. AIMS: To review the literature up to 2021 on the Meliaceae family with antiplasmodial, insecticidal and cytotoxic activity. MATERIALS AND METHODS: A number of online libraries including PubMed, Scifinder, Google Scholar and Web of Science were used in searching for information on antiplasmodial metabolites from Meliaceous plants. The keywords Meliaceae, malaria, Plasmodium, Anopheles and antiplasmodial were used to monitor and refine our search without language restriction. RESULTS: The phytochemical investigations of genera of the family Meliaceae led to the isolation and characterization of a wide range of structural diversity of compounds, 124 of which have been evaluated for their antiplasmodial potency against 11 chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains. A total of 45 compounds were reported with promising insecticidal potentials against two efficient vector species, Anopheles stephensi Liston and A. gambiae Giles. Limonoids were the most abundant (51.6%) reported compounds and they exhibited the most promising antiplasmodial activity such as gedunin (3) which demonstrated an activity equal to quinine or azadirachtin (1) displaying promising larvicidal, pupicidal and adulticidal effects on different larval instars of A. stephensi with almost 100% larval mortality at 1 ppm concentration. CONCLUSION: Studies performed so far on Meliaceae plants have reported compounds with significant antiplasmodial and insecticidal activity, lending support to the use of species of this family in folk medicine, for the treatment of malaria. Moreover, results qualified several of these species as important sources of compounds for the development of eco-friendly pesticides to control mosquito vectors. However, more in vitro, in vivo and full ADMET studies are still required to provide additional data that could guide in developing novel drugs and insecticides.
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Antimaláricos/farmacología , Insecticidas/farmacología , Meliaceae/química , Fitoterapia , Extractos Vegetales/farmacología , Animales , Antimaláricos/química , Humanos , Insecticidas/química , Fitoquímicos/química , Fitoquímicos/farmacología , Extractos Vegetales/químicaRESUMEN
The stem bark of Ancistrocarpus densispinosus Oliv. exhibited triterpenoids, including the rare fernane-type, fern-9(11)-ene-2α,3ß-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.
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Malvaceae , Fitosteroles , Triterpenos , Bacterias , Línea Celular Tumoral , Humanos , Malvaceae/química , Fitosteroles/química , Extractos Vegetales , Triterpenos/químicaRESUMEN
The chemical investigation of the root barks leaves and stem barks of Brucea antidysenterica J. F. Mill. (Simaroubaceae) led to the isolation of a new pregnane glycoside, named Bruceadysentoside A or 3-O-ß-L-arabinopyranosyl-pregn-5-en-20-one (1) together with seventeen known compounds. Their structures were established from spectral data, mainly HRESIMS, 1 D and 2 D NMR and by comparison with literature data. Compounds 1, 2, 5, 6, 8, 10, 12 and 13 were tested 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. No substantial activities were recorded for 2, 10, 12 and 13 (up to 10 µM concentration). 1, 5 and 8 did not show strong anti-proliferative effects up to 100 µM, however, 6 exhibited a stronger anti-proliferative effect with IC50 values of â¼ 100 µM against PC-3 and â¼ 200 µM against HT-29.
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Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Brucea/metabolismo , Brucea/química , Ensayos de Selección de Medicamentos Antitumorales , Glicósidos/química , Células HT29 , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Células PC-3 , Extractos Vegetales/química , Hojas de la Planta/química , Pregnanos/química , Metabolismo Secundario , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
We report the chemistry and biological activities of a Cameroonian Citrus clementina Hort. Ex Tanaka, a vegetatively propagated species. The compounds isolated from this plant were determined to be the known 5-hydroxy-6,7,8,3',4'-pentamethoxyflavone (1), tangerine (3), nobilletin (4), 5,7,8,4'-tetramethoxyflavone (5), citracridone I (6), 5-hydroxynoracronycine (7), citracridone III (8), xanthyletin (10), suberosin (9), E-suberenol (11), E-methoxysuberenol (13), 6-formylumbelliferone (12), aurantiamide acetate (2), limonin (14), stigmasterol, ß-sitosterol and ß-sitosterol-3-O-ß-D-glucoside. The structures of the compounds were established on the basis of their NMR spectroscopic data and comparison with published data. Methanol leaf extract and compounds 1, 2, 4, 6, 7 and 10 were evaluated for their anti-inflammatory, antioxidant, urease and anti-diabetic effects. Compound 10 showed antioxidant activity, anti-inflammatory effect, urease activity and anti-diabetic activity with IC50 values of 47.3 µM, 33.5 µM, 25.2 µM and 33.9 µM respectively, values that were comparable to the respective positive standards.
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Citrus , Rutaceae , Antiinflamatorios , Antioxidantes/farmacología , Extractos Vegetales/farmacologíaRESUMEN
The phytochemical investigation of the methanolic extracts of roots, stem bark, leaves and twigs of Manilkara obovata has led to the isolation of one new friedelane triterpene, lacefriedelic acid or 3ß,23-dihydroxy D:A-friedooleanan-28-oic acid (1) and one new prenylated xanthone, lacexanthone or 4,7-dihydroxy-2,3,3,9,9-pentamethyl-2,2-dihydrofurano[2,3-a]pyrano[2,3-i]xanthen-13(9H)-one (2) alongside twenty-four known compounds. Compounds 1-11 are reported here for the first time from the genus Manilkara. The structures of all compounds were determined by spectroscopic analyses and X-ray crystallography. The methanolic extracts of twigs and leaves showed anti-oxidant activity of 93.2 and 91.1%, respectively, at 100 µg/mL when measured by DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate), while the twig extract displayed 86.3% at 100 µg/mL against the urease inhibition assay. Some isolated compounds (1-4, 15 and 20) showed significant to moderate anti-oxidant activity and urease inhibition assay. It is estimated that significantly active anti-oxidants and urease inhibitors metabolized by the plant may find future application in food industry.
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Manilkara , Antioxidantes/farmacología , Fitoquímicos , Extractos Vegetales/farmacología , Hojas de la PlantaRESUMEN
The phytochemical exploration of the Entandrophragma candollei stem bark extract led to the isolation and identification of twenty compounds including three undescribed phragmalin-class limonoids named encandollens C-E (1-3), the undescribed protolimonoid 5 together with sixteen known compounds. The structures of all the isolated compounds were determined by interpretation of their spectroscopic and spectrometric data including HRMS, 1D and 2D NMR analyses. The assignment of the absolute and relative stereochemistry of the undescribed compounds was achieved using SC-XRD analyses as well as NOESY experiments. The previously reported structure of odoratone (5a) was corrected as 23 R,24 S-dihydroxy-22 S,25-epoxytirucall-7-en-3-one (5) based on its NMR and SC-XRD data. Prieurianin (4) exhibited high cytotoxic activity on KB3-1 cell lines with an IC50 of 1.47 µM compared to the reference griseofulvin (IC50 = 17-21 µM). The results of the in silico docking of compound 4 supported and delivered further insights on its cytotoxicity.
Asunto(s)
Limoninas , Meliaceae , Limoninas/farmacología , Estructura Molecular , Corteza de la PlantaRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Species of the genus Vepris are used in traditional African pharmacopeia for the treatment of various conditions, including chronic diseases and other parasitic. Further uses are against whooping cough and colic in children and as an antidote against snakebite. Data presented will enable the interested scientists to work on this genus applying the so-called "ethnopharmacologic approach", which may lead towards the discovery of the effective, safe plant medicinal products. AIM OF THE REVIEW: This review article aims to collate and analyse the available information on the traditional uses, phytochemistry, pharmacology, and toxicological aspects of Vepris species in order to explore the trends and perspectives for further studies. METHODOLOGY: The present review paper collected the literature published prior to August 2020 on the ethnomedicinal uses, phytochemistry, and pharmacology of the genus Vepris. The available information about the genus Vepris was collected via Google Books, Google Scholar, PubMed, ScienceDirect, SciFinder, Web of Science, and other internet sources. The Global Biodiversity Information Facility (www.gbif.org), Plants of the world online (www.plantsoftheworldonline.org), and The Plant List (www.theplantlist.org) databases were used to verify the scientific names and provide distribution information of Vepris species. RESULTS: Comprehensive analysis of the literature provided information on ethnopharmacological uses of 30 species out of 83 members in the genus. A total of 213 compounds - predominantly alkaloids - were reported together with results from antioxidant, cytotoxic, antimicrobial, antiplasmodial, antitrypanosomal, antileishmanial, antidiabetic, antipyretic, analgesic, insect antifeedant, and toxicity assays. Arborinine (49) and skimmianine (4) isolated from the leaves of V. trichocarpa were tested toxic in rat skeletal myoblast cell line L6, a stable skeletal muscle progenitor cell line, while the leaves of V. heterophylla, the stem bark of V. louisii, and the roots of V. uguenensis were shown to be toxic against model organisms T. castaneum (Tenebrionidae), H. bakeri (Trychostrongylidae), and M. domestica (Muscidae), respectively. In addition, 6,7-methylenedioxy-5-hydroxy-8-methoxy-dictamnine (40) isolated from the leaves of a combined sample of V. renieri + V. suaveolens displayed an extremely low IC50 of 0.67 µM against the normal fibroblastic lung cell line MRC-5 indicating high toxicity. Thus, medical use of these plant parts, as well of the stem bark of V. verdoorniana used locally in poison fishing, should be avoided if alternative treatments exist. Furthermore, a good number of significantly in vitro bioactive compounds have been reported from the genus Vepris: against malaria and against microbial infections. CONCLUSIONS: Various Vepris species were found to be used in traditional African pharmacopeia. However, few of these species were studied for their bioactive chemical constituents with even fewer bioassay-guided isolation studies being reported. Moreover, detailed pharmacological studies in animal models to explore their mode of action were not reported. Therefore, future studies should focus on these aspects. In addition, we would like to recommend further research on some significantly bioactive crude extracts that were identified in this review: V. leandriana; V. lanceolata; V. nobilis; and V. trichocarpa, as well as those plants reported to be used against chronic diseases.
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Medicinas Tradicionales Africanas , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Rutaceae , Animales , Etnobotánica , Humanos , Fitoquímicos/aislamiento & purificación , Fitoquímicos/toxicidad , Fitoterapia , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Rutaceae/química , Rutaceae/toxicidadRESUMEN
A phytochemical study of the root and bark of Brucea antidysenterica J. F. Mill. (Simaroubaceae) afforded three new compounds, including a stilbene glycoside bruceanoside A (1), and two canthinone alkaloids bruceacanthinones A (3) and B (4), along with ten known secondary metabolites, rhaponticin (2), 1,11-dimethoxycanthin-6-one (5), canthin-6-one (6), 1-methoxycanthin-6-one (7), 2-methoxycanthin-6-one (8), 2-hydroxy-1,11-dimethoxycanthin-6-one (9), ß-carboline-1-propionic acid (10), cleomiscosin C (11), cleomiscosin A (12), and hydnocarpin (13). The structures of all the compounds were determined using spectrometric and spectroscopic methods including 1D and 2D NMR, and HRSEIMS. The identities of the known compounds were further confirmed by comparison of their data with those reported in the literature. The root and bark methanolic extracts, the dichloromethane and ethyl acetate soluble fractions, and the isolated compounds (3-13), were assessed for their cytotoxicity against the cancer cell lines A-549, MCF-7, and PC-3. The results suggested that compounds in the extracts might possess a synergic action in their cytotoxicity.
Asunto(s)
Alcaloides/farmacología , Antineoplásicos Fitogénicos/farmacología , Brucea/química , Medicamentos Herbarios Chinos/farmacología , Estilbenos/farmacología , Células A549 , Alcaloides/química , Antineoplásicos Fitogénicos/química , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Sinergismo Farmacológico , Medicamentos Herbarios Chinos/química , Humanos , Células MCF-7 , Estructura Molecular , Células PC-3 , Extractos Vegetales/química , Extractos Vegetales/farmacología , Metabolismo Secundario , Estilbenos/químicaRESUMEN
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, ß-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, 1H and 13C NMR spectra show two rotamers (1a and 1b) with integrated intensities of 2/3, whereas at around 60⯰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 luteus and Escherichia coli with MIC values of 15.3 and 15.3⯵g/mL, respectively.
Asunto(s)
Alcaloides/farmacología , Escherichia coli/efectos de los fármacos , Micrococcus luteus/efectos de los fármacos , Niacinamida/análogos & derivados , Rutaceae/química , Triptaminas/farmacología , Alcaloides/química , Alcaloides/aislamiento & purificación , Cristalografía por Rayos X , Estructura Molecular , Niacinamida/química , Niacinamida/aislamiento & purificación , Niacinamida/farmacología , Raíces de Plantas/química , Triptaminas/química , Triptaminas/aislamiento & purificaciónRESUMEN
One new depsidone, polyanthadepsidone A (1), together with four known compounds were isolated from the dichloromethane extract of the leaves of Garcinia polyantha. The structures of all compounds were determined by comprehensive analyses of their 1D and 2D NMR and EI mass spectral data. All the isolates exhibited suppressive effect on phagocytosis response upon activation with serum opsonised zymosan in the IC50 range of 4.5-23.80 µM, tested in vitro for oxidative burst studies of whole blood.
Asunto(s)
Depsidos/química , Garcinia/química , Lactonas/química , Evaluación Preclínica de Medicamentos/métodos , Humanos , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Estructura Molecular , Fagocitosis/efectos de los fármacos , Extractos Vegetales/química , Hojas de la Planta/química , Estallido Respiratorio/efectos de los fármacos , Zimosan/farmacologíaRESUMEN
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, ß-sitosterol, stigmasterol, ß-sitosterol-3-O-ß-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.