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HPLC chromatogram of total alkaloids from Guiera senegalensis: (A) roots; (B) leaves, sample GsC (1 = tetrahydroharman; 2 = harmalan; 3 = harman; 4 = guieranone A).
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The chemical composition of total alkaloids from leaves and roots of Guiera senegalensis was investigated. Three beta-carboline alkaloids were purified: in addition to harman and tetrahydroharman, known in roots and leaves, harmalan (dihydroharman) was isolated for the first time from roots of Guiera senegalensis. Guieranone A, a naphthyl butenone,...
Context in source publication
Context 1
... chromatographic profiles of total alkaloids studied showed some differences in qualitative and quantitative compo- sition, especially between roots and leaves. Fig. 1 presented the chromatogram of alkaloids from roots and leaves (sample GsC). In the root extract, four compounds (1-4) were eluted with reten- tion time of 7.6 min (1), 9.1 min (2), 10.6 min (3) and 40.2 min (4). In the two leaves extracts, eight compounds were eluted. The compounds 1, 3 and 4 were present, with the same reten- tion ...
Citations
... For example, C. glutinosum and C. micranthum are known for their use in the treatment of malaria, whereas Terminalia leiocarpa and Terminalia avicennioides are used for external infections such as abscesses and wounds (Kerharo & Adam, 1974). The existing scientific literature confirms these traditional uses (Bosisio et al., 1997;Fiot et al., 2006;de Morais Lima et al., 2012;Bajaj et al., 2020). ...
... (MICs between 0.0185 and 0.0375 mg/mL) and an antimycobacterial activity against Mycobacterium marinum of a polar extract (IC 50 = 0.098 mg/mL) (Diop et al., 2018;Dirar and Devkota, 2021). β-Carboline alkaloids including harman and tetrahydroharman, naphthopyrones, as well as guieranone A, a naphthyl butanone, were previously identified in the leaves of G. senegalensis and showed antimicrobial and antimalarial activities (Silva and Gomes, 2003;Fiot et al., 2006). Different specialized metabolites were identified and purified from the leaves of Combretum glutinosum including methoxylated flavones (umuhengerine, 5-demethylsinensetin, corymbosin), hydrolyzable tannins (combreglutinin) and triterpenoids and phytosterols ((20S, 24R)-ocotillone, lupeol, β-sitosterol, oleanolic acid, betulinic acid) (Jossang et al., 1994;de Morais Lima et al., 2012;Sene et al., 2019). ...
... The cytotoxicity of guieranone A, one of the essential molecules of Guiera senegalensis, was performed on two cancer cell lines (HeLa and HCT-116) and fibroblasts of normal skin to study its anticancer potential. This component had considerable cytotoxic properties, with an IC 50 of 9.2 and 6.9 M on HeLa and HCT-116 cell lines, respectively [39]. Although the in vitro cytotoxic activity of the aqueous extract of the recipe «Acti-plus» is moderate, an in vivo evaluation is necessary to draw precise conclusions on the preventive and anticancer effects of this recipe. ...
... However, the mechanisms of action underlying guieranone A antifungal activity remain to be clarified. Furthermore, the presence of toxic alkaloids has been identified in different parts of G. senegalensis, including in the leaves and roots [8]. Thus, the valorization of G. senegalensis for new fungicide development requires the establishment of clear relationships between the chemical composition of the plant extracts and the antifungal activity. ...
... Several studies report the presence of β-carboline alkaloids in different parts of G. senegalensis, including in the leaves [8,15,16]. Thus, a preliminary screening for the presence of this class of compounds was carried out with the alkaloids reagents (Dragendorff, Mayer and Bertrand) in the G. senegalensis CME, EAF and MF, and the results were negative. Previous studies that report the presence of alkaloids in G. senegalensis are based on extracts that are generally obtained with solvents with lower polarity, such as dichloromethane and chloroform [8,15]. ...
... Thus, a preliminary screening for the presence of this class of compounds was carried out with the alkaloids reagents (Dragendorff, Mayer and Bertrand) in the G. senegalensis CME, EAF and MF, and the results were negative. Previous studies that report the presence of alkaloids in G. senegalensis are based on extracts that are generally obtained with solvents with lower polarity, such as dichloromethane and chloroform [8,15]. In fact, HPLC analysis of an alkaloid-directed extract obtained from leaves or from the solid residue of the CME confirmed the presence of these compounds in the G. senegalensis leaves and their absence in the CME ( Figure S1). ...
Pest resistance against fungicides is a widespread and increasing problem, with impact on crop production and public health, making the development of new fungicides an urgent need. Chemical analyses of a crude methanol extract (CME) of Guiera senegalensis leaves revealed the presence of sugars, phospholipids, phytosterols, guieranone A, porphyrin-containing compounds, and phenolics. To connect chemical composition with biological effects, solid-phase extraction was used to discard water-soluble compounds with low affinity for the C18 matrix and obtain an ethyl acetate fraction (EAF) that concentrates guieranone A and chlorophylls, and a methanol fraction (MF) dominated by phenolics. While the CME and MF exhibited poor antifungal activity against Aspergillus fumigatus, Fusarium oxysporum and Colletotrichum gloeosporioides, the EAF demonstrated antifungal activity against these filamentous fungi, particularly against C. gloeosporioides. Studies with yeasts revealed that the EAF has strong effectiveness against Saccharomyces cerevisiae, Cryptococcus neoformans and Candida krusei with MICs of 8, 8 and 16 μg/mL, respectively. A combination of in vivo and in vitro studies shows that the EAF can function as a mitochondrial toxin, compromising complexes I and II activities, and as a strong inhibitor of fungal tyrosinase (Ki = 14.40 ± 4.49 µg/mL). Thus, EAF appears to be a promising candidate for the development of new multi-target fungicides.
... Prostaglandins also suppress NSAID-induced gastric injury largely via inhibiting gastric acid secretion. [28] It also reduces epithelial permeability to acid. [25] Additionally, prostaglandins down-regulate the release of some inflammatory mediators implicated in mucosal injury. ...
Gastric lesions and ulcerations are predominantly induced by aggressive factors such as stress, alcohol consumption, and Helicobacter pylori infection due to the use of non-steroidal anti-inflammatory drugs. The use of phyto-therapy in management of gastric ulcerations and lesions dates back centuries ago. So many plant-derived compounds are employed clinically to manage diseases and they were also the basis of drug discovery. Plant products with gastro-protective and cyto-protective properties are widely employed globally due to their natural source and minimal adverse effects. Secondary metabolites found in these plants can be utilized for the management of various ailments. Some examples of plant bioactive compounds are alkaloids, flavonoids, carnitine, choline, phenolic acids, saponin, glycosides, polyphenols and taurine. However, vitamins and minerals elicit pharmacological activity and are categorized as bioactive agents. Some of these bioactive compounds/ secondary metabolites are found in food.
... [6]-Gingerol (Nigam et al., 2009) 6. Anticarcinogenic 6. Non-volatile pungent principles (gingerols, shogaols, paradols and zingerone) (Kundu et al., 2009) (Fiot et al., 2006) 3. 5-methyldihdroflavasperone (Mosa et al., 2022) 65 (Tragoolpua and Jatisatienr, 2007) 3. Antimicrobial, antioxidant, antifungal, antiviral activity, anti-inflammatory, cytotoxic, insect repellent. and anesthetic 3. Essential oil phenylpropanoids (carvacrol, thymol, eugenol, and cinnamaldehyde) (Chaieb et al., 2007) 76 ...
... Despite the known antimalarial activity of quinoline alkaloids, another subclass of indole alkaloids, the β-carbolines, has been highlighted since some studies have demonstrated its efficacy in vitro and in vivo against Plasmodium spp. [16,55,56,60,61,[71][72][73][74]. ...
... Some β-carboline derivatives were in vitro active against both sensitive or multiresistant P. falciparum strains, showing low IC 50 and important SI values [71,74]. In the in vivo trials, these studies used non-severe malaria induced by the P. berghei NK65 model, and an antiplasmodial activity was observed. ...
Malaria is an infectious disease widespread in underdeveloped tropical regions. The most severe form of infection is caused by Plasmodium falciparum, which can lead to development of cerebral malaria (CM) and is responsible for deaths and significant neurocognitive sequelae throughout life. In this context and considering the emergence and spread of drug-resistant P. falciparum isolates, the search for new antimalarial candidates becomes urgent. β-carbolines alkaloids are good candidates since a wide range of biological activity for these compounds has been reported. Herein, we designed 20 chemical entities and performed an in silico virtual screening against a pool of P. falciparum molecular targets, the Brazilian Malaria Molecular Targets (BRAMMT). Seven structures showed potential to interact with PfFNR, PfPK7, PfGrx1, and PfATP6, being synthesized and evaluated for in vitro antiplasmodial activity. Among them, compounds 3–6 and 10 inhibited the growth of the W2 strain at µM concentrations, with low cytotoxicity against the human cell line. In silico physicochemical and pharmacokinetic properties were found to be favorable for oral administration. The compound 10 provided the best results against CM, with important values of parasite growth inhibition on the 5th day post-infection for both curative (67.9%) and suppressive (82%) assays. Furthermore, this compound was able to elongate mice survival and protect them against the development of the experimental model of CM (>65%). Compound 10 also induced reduction of the NO level, possibly by interaction with iNOS. Therefore, this alkaloid showed promising activity for the treatment of malaria and was able to prevent the development of experimental cerebral malaria (ECM), probably by reducing NO synthesis.
... Initial works showed that leaves and roots of G. senegalensis restrain Harman, tetrahydroharman, harmalan and Guieranone A. [1] The plant has been found to prevail alkaloids, carbohydrates, flavonoids, mucilage, steroids, saponins, and tannins. [24,26] Ficarra et al., in 1997 ascertain four flavonoids in the leaves of G. senegalensis, specifically contain catechin, myricitrin, rutin and querterin. ...
... [27] Guieranone A from Guiera senegalensis exhibits a strong antiplasmodial activity associated with a high cytotoxicity toward human monocytes. [1] Methanol fraction from leaves extract possess only antiplasmodial property. [28] ...
... Both 5-methylflavasperone and rhamnetin are reported to induce inhibitory effects on 5-lipoxygenase and the hydroxyl radical (Bucar et al. 1998). Other identified compounds include guieranone A, an antifungal compound, and the indole alkaloids: harman, harmalan and tetrahydroharman (Fiot et al. 2006;Silva & Gomes 2003). ...
Background: Guiera senegalensis (Ghibaish) is a medicinal plant extensively used in central and west Africa for the management of various diseases.
Aim: This study aimed to determine the antioxidant activity of the ethanol leaf extract of the plant.
Method: The ethanol leaf extract was sequentially sub-fractionated using liquid–liquid extraction, vacuum-liquid chromatography and preparative thin layer chromatography. Ultra-performance liquid chromatography with accurate mass spectrometry and nuclear magnetic resonance were employed to isolate and confirm the identity of the most abundant compound. The antioxidant activity of the fractions and isolated compound was assessed by bioautography analysis and the 2,2-diphenyl-1-picrylhydrazyl hydrate (DPPH) radical scavenging assay.
Results: The dichloromethane subfraction contained the most promising antioxidant activity (IC50 = 3.18 µg/mL). Purification of this subfraction led to the isolation of a brown crystalline compound, which was identified as 5-methyldihydroflavasperone (IC50 4000 µg/mL).
Conclusion: This is the first report of the isolation of 5-methyldihydroflavasperone from the ethanol leaf extracts of G. senegalensis. This compound was not found to be responsible for the antioxidant activity observed. Further research is warranted to identify the compound responsible for the antioxidant activity.
... (1) Ancolio et al. (2002) (2) Fiot et al. (2006) Psidium guajava L. ...
Malaria is a major health burden among populations with poor economic status in tropical and subtropical regions of the world. Ineffective cost of drugs, multi-drug resistance of malaria parasites and inadequate health facilities are the major factors responsible for high mortality rates in these regions. These has prompted the need to identify new, efficient, safe and cheap drugs. This study was carried out to collect and
document information on medicinal plants and how they are traditionally applied in the treatment of malaria in Kafin Hausa. Questionnaires were used for data collection by means of oral interview. Analysis of data collected was done using ethnobotanical indices.
Forty-three (43) respondents were interviewd and 15 plant species were mentioned. The plants were classified into 12 families with Buseraceae having the largest number of species. Senna occidentalis had the highest RFC (75.7%). Boswellia dalzielii, Boswellia serrata, Azadirachta indica and Vitex doniana all had fidelity level of 100%. Informant consensus factor of 0.87 was recorded. Literature search on antimalarial activities of the medicinal plants mentioned, showed that extracts from these medicinal plants had IC50 values ranging from 2.3 - <50 μg/ml, while isolated compounds from some of the mentioned plants had IC50 values between 0.7 - 24 μg/ml. This research has provided background data on the medicinal plants traditionally employed for malaria treatment in Kafin Hausa. These findings could serve as a basis for the advancement of pharmacological studies on these medicinal plants with emphasis on safety, standardization and dosage.
... Previous studies indicated the presence in leaves Guiera senegalensis of two alkaloids, flavonoids, naphthyl butenone (guieranone A), naphthopyrans and tannins [28]. The phytochemical screening was conducted and the result revealed that Gs crude extract contains ...
The effects of Guiera senegalensis leaves extract as a potential green corrosion inhibitor for Aluminum (Al) in HCl acid solution was investigated using weight loss, LPR, FT-IR, and scanning electron microscope techniques at varying experimental conditions. The result indicates that the percentage inhibition efficiency increases with increase in concentration of the inhibitor and decreased with increase in temperature and immersion period. SEM images showed that the Al metal is protected by the inhibitor molecules, while FT-IR spectra indicates the mechanism of physical adsorption of inhibitors onto Al surface. LPR result showed that the inhibition efficiency of the inhibitor was moderate and act as mixed-type inhibitor. The data obtained from the thermodynamic parameters were fitted into various adsorption isotherms, Freundlich adsorption isotherm was observed to be the best fitted isotherm.
