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The Carao (Cassia grandis L.): Its Potential Usage in Pharmacological, Nutritional, and Medicinal Applications

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Abstract

Recently, functional foods have generated a lot of attention among consumers, who are looking for healthy options that allow them to appreciate good consuming habits. For this reason, the study of natural sources of bioactive compounds has aroused growing interest in the scientific community. This chapter highlights the potential of carao (Cassia grandis) as a functional food and nutraceutical since its bioactive compounds are noteworthy to consider regarding nutritional, pharmacological, and medicinal purposes. The search of different studies determined that the carao fruit has higher concentrations of phenolic compounds and antioxidant activity in the seeds, which could exert a potential anticancer function by inhibiting cell aging. However, the pulp shows a higher content of carotenoids and it increases the production of vitamin A (retinol). Among the macro minerals content, the ones that stand out the most are magnesium and calcium, and iron and manganese are the most abundant among the micro minerals. For the extraction and determination of bioactive compounds from carao, the most efficient technique is through pressurized fluids, and, for its characterization, the method utilized is high-resolution liquid chromatography coupled to electrospray ionization-time-of-flight-mass spectrometry (HPLC-ESI-TOF/MS). For identification and quantification of phenolic compounds, the hydroxybenzoic acids, flavonoids (flavonols, flavanols, flavanones, and proanthocyanidins), and flavone derivatives. Therefore, Cassia grandis is an option to explore and examine its use in the development of drugs and fortified foods for consumers with special diets.Keywords Cassia grandis Phenolic compoundsCarotenoidsMineralsPressurized fluidsHigh-resolution liquid chromatographyMass spectrometryBioactive molecules

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... In South America, Cassia grandis (carao) is an exotic plant that has been used by indigenous tribes for centuries for treating anemia, skin ulcers, and diabetes [9]. Fuentes et al. [10] stated that carao has great potential for nutritional, pharmacological, and medicinal applications. Fuentes et al. [11] determined that in the pulp, seeds, and bark, there are high amounts of carotenoids, the precursors of vitamin A, which promote the formation and conservation of dental and bone tissues, mucous membranes, and skin. ...
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Carao is considered a functional ingredient since its bioactive compounds are meaningful in nutritional, pharmacological, and medicinal applications. The objective of this study was to determine the effects of carao pulp powder on the bacterial viability, acid tolerance, bile tolerance, and protease activity of S. thermophilus STI-06 and L. bulgaricus LB-12. M17 broth with 0.5% lactose and MRS broth were used for S. thermophilus and L. bulgaricus, respectively, for determining bacterial viability, acid tolerance, and bile tolerance. Skim milk was used to study the protease activity of both bacteria. The carao was added at 0 (control), 1.3, 2.6, and 5.3 (g/L) into the broths and skim milk. The broths were enumerated for bacterial viability (every 2 h), bile tolerance (every 4 h), and acid tolerance (every 30 min), and the skim milk was analyzed for protease activity (every 12 h). The General Linear Model (PROC GLM) was used to analyze the data. The 2.6 g/L and 5.3 g/L usage level of carao improved the acid tolerance of S. thermophilus. Carao did not affect the acid tolerance of L. bulgaricus. The usage of 5.3 g/L of carao significantly improved the bile tolerance and protease activity of both bacteria. However, carao did not affect the viability of either bacteria. Overall, 5.3 g/L of carao with these probiotics could be recommended in fermentation processes.
... Además, la fortificación de los alimentos es un método barato y de fácil aplicación, que garantiza la seguridad alimentaria y nutricional de la población 23 . Por lo que es indispensable considerar el uso de biomoléculas provenientes de plantas con potencial funcional para aumentar el contenido nutricional del ereba mediante su fortificación [24][25] . Asimismo, se aprovecharía el potencial medicinal y farmacológico de las plantas que se ubican en las zonas Garífunas de Honduras, por su contenido de aceites esenciales y polifenoles como antioxidantes, carotenoides, minerales y otras moléculas bioactivas que promuevan la soberanía alimentaria y la salud del pueblo Garífuna de Honduras [26][27][28][29][30] . ...
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Desde la cosmovisión de la antropología alimentaria, al estudiar los orígenes de los pueblos, se asume metafóricamente que los latinoamericanos “somos hombres de maíz y de yuca”; la comunidad Garífuna de Honduras es la principal consumidora de yuca y derivados como el ereba (casabe) y sobresale en la técnica gastronómica ancestral para su elaboración, lo que promueve la soberanía alimentaria. La Agenda 2030, impone a las universidades, la necesidad de dar respuesta a los objetivos de desarrollo sostenible (ODS), varios de ellos relacionados con la alimentación. Este artículo tiene por objetivo realizar como academia, una alerta a la comunidad Garífuna hondureña sobre el consumo de la yuca y el casabe para ayudar a garantizar la seguridad y la soberanía alimentaria de esta población desprotegida y pobre de Honduras, mediante una revisión bibliográfica exhaustiva, contribuyendo así a afrontar los retos de los ODS de la Agenda 2030, teniendo en cuenta la toxicidad de la yuca, las enfermedades provocadas por la posible intoxicación respecto a su consumo y los métodos de detoxificación ancestral utilizada para hacer casabe. Palabras clave: Compuestos Cianogénicos, Comunidad Garífuna, Toxicidad, Detoxificación.
... Medicinal plants provide many benefits for the human, and one of the most important is their contribution to health benefits due to their phytochemicals that are also known as bioactive compounds (Fuentes et al., 2020;Olivet et al., 2022). Lately, awareness of individuals has been increasing towards beneficial diets and healthy foods, which perspective has been paid close attention to bioactive compounds Marcía et al., 2021). Because of the content of bioactive molecules, African palm (E. ...
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... Medicinal plants provide many benefits for the human, and one of the most important is their contribution to health benefits due to their phytochemicals that are also known as bioactive compounds (Fuentes et al., 2020;Olivet et al., 2022). Lately, awareness of individuals has been increasing towards beneficial diets and healthy foods, which perspective has been paid close attention to bioactive compounds Marcía et al., 2021). Because of the content of bioactive molecules, African palm (E. ...
Article
Full-text available
African palm oil (Elaeis guineensis Jacq.) is an oil that contains phytosterols, which are rich antioxidants that are capable of decreasing the intestinal absorption of cholesterol in the human body. Freeze-drying is a technique commonly used in the drying and powdering of encapsulated essential oils since its benefits allow the preservation of its physical and chemical properties. The phytosterols are of medical interest due to their potential to treat hypercholesterolemia. Therefore, this study attempts to optimize the drying process of canola oil with phytosterols using the lyophilization process. Water/oil solution (85.2%), maltodextrin/sodium alginate mixture (12.8%) and soy lecithin (2%) were used to prepare the emulsion. A surface response methodology was applied to determine the effects of water/oil and maltodextrin/sodium alginate mixture on the phytosterols encapsulation efficiency, water activity, solubility, and oxidative stability index on the produced lyophilized product. For the optimization, these physical-chemical attributes were evaluated as the dependent variables and the proportions of water/oil ratios and maltodextrin/alginate concentrations as the independent variables. An optimal treatment was determined with concentrations of 13.5 grams of maltodextrin, 1.5 grams of alginate, 84.2 ml of water, and 15.7 ml of oil. A predictive phytosterols content of 40 mg was obtained per gram of lyophilized product, an induction time of 33.15 hours in oxidative stability and solubility of 59.96%.
... Otras investigaciones con plantas que se encuentran en Centroamérica y Cuba, como la Cassia grandis, han demostrado su efecto medicinal, nutricional y farmacológico, por la presencia de fitoquímicos con alta actividad antioxidante, contenido carotenoides y moléculas bioactivas, | 58 convirtiéndose en una alternativa para la producción agroindustrial, como fuentes de alimentos potencialmente funcionales [14]- [16]. ...
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p>En los últimos años, ha habido una tendencia global hacia el consumo de alimentos que proporcionen efectos beneficiosos para la salud. Las principales investigaciones demuestran que el uso de compuestos bioactivos derivados de plantas como fuente de ingredientes funcionales en los productos alimenticios puede disminuir el riesgo de enfermedades cardiovasculares y neurodegenerativas. Estos beneficios han orientado las investigaciones principalmente a la caracterización de diferentes tipos de frutas y su contenido de componentes antioxidantes específicos, sin embargo, la mayoría se han centrado en las frutas de clima templado. Por lo tanto, esta revisión se centra en exponer el contenido de compuestos bioactivos presentes en frutas tropicales, evidenciando sus beneficios sobre la salud humana a través su aprovechamiento agroindustrial en productos alimenticios, jugos con antioxidantes, en general fuentes bioactivos para la industria. </p
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ABSTRACT Introduction: The species Cassia grandis L. f. (cañandonga) is recognized by the Cuban Health System and the population for its antianemic properties, in spite of the unpleasant odor of its fruit. Objectives: to perform a bibliographic update about the chemical, toxicological and pharmacologic characteristics of the study species. Methods: an extensive review was conducted in international databases such as HighWire, DOAJ, EBSCO, Scielo, Scopus, Chemical Abstract, Medline, PudMed, and Pharmaceutical Abstract, in addition to the national database CuMed from the year 1900 until 2012. Results: There are still not enough studies that certify its usefulness and pharmaco-toxicological safety as antianemic, and few pharmaceutical formulations have been developed. The fruit is the most studied organ of the species. Conclusions: It is necessary to carry out new investigations to certify its antianemic effect and develop new therapeutic alternatives to eliminate the unpleasant odor of Cassia grandis L. f. fruit formulations
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Resumen Cassia grandis L. popularmente conocida como Cañandonga, es un árbol al cual se le atribuyen propiedades antianémicas. Para el uso medicinal de esta especie se elaboraron 3 formas farmacéuticas las cuales se nombraron Ferroscassia droga seca, polvo para infusión e instaferross. En el presente estudio se evaluó la toxicidad aguda oral de estas 3 formulaciones con el objetivo de avalar su posterior uso en humanos. Dicha evaluación se llevó a cabo en un ensayo de prueba límite a una dosis de 2 000 mg/kg de peso corporal en ratas Wistar de ambos sexos por vía oral. El estudio agudo realizado demostró que las 3 formulaciones ensayadas pueden clasificarse como no tóxicas ya que no se evidenció toxicidad alguna a la dosis administrada. Descriptores DeCS: PLANTAS MEDICINALES; RATAS DE CEPAS CONSANGUINEAS; MEDICINA TRADICIONAL; TESTS DE TOXICIDAD. Summary Cassia grandis L. (folk name: Cañandonga), is a tree with attributable antianemic properties. For medicinal use of this plant, we processed three pharmaceutical forms, which were named as dry drug Ferroscassia, infusion powders, and instaferross. In present study, oral acute toxicity of these three formulations was assessed to guarantee subsequent use in humans. Such assessment was done in a trial of limit test at a dose of 2 000 mg/kg of body weight (bw) in Wistar rats of both sexes. Acute study, carried out, showed that the three formulations tested, may be classified as non-toxic since it wasn´t demonstrate toxicity using doses above mentioned.
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A manufacturing design and control of bioactive ingredients from Aloysia citriodora was performed applying microwave-assisted extraction (MAE). Thus, a Response Surface Methodology based on Central Composite Design 2³ model was performed to monitor the matrix behavior. The factors were extraction time, percentage of solvent and temperature. The chosen responses were extraction yield and phytochemicals recovery. The design allowed to find the optimal conditions for each response and to validate them in order to attain high quality ingredients. These results pointed out that MAE is a novel technique which could be used to improve the new functional ingredient development.
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The extraction of total phenolics (TPC), total flavonoids content (TFC), total saponins content (TSC), and caffeic acid (AC) contents of asparagus roots extract (ARE) from New Zealand and Chinese AR cultivars was optimized following a microwave-assisted extraction combined with central composite design. The determination of AC was conducted by HPLC in samples extracted under the optimum extraction conditions. The optimal variables for ethanol extraction generated a maximum TPC, TFC and TSC of optimal results for 68.6 mg GAE/g, 11.9 mg RE/g and 0.7 mg SE/g as well as antioxidant power towards β-carotene bleaching assay (%βsc) (57.2%), superoxide anion radical (%O 2−sc ) scavenging capacity (20.1%) and ferric reducing antioxidant power assay (FRAP) (1.63 µmol/g). For methanol, optimum extraction conditions obtained maximum TPC (62.6 mg GAE/g) TFC (10.7 mg RE/g), TSC (0.68 mg SE/g) with %βsc (53.9%), %O 2−sc (19.1%) and FRAP (0.63 µmol/g). The content of caffeic acid from ARE ranged from 0.46 to 2.89 mg/g with ethanol and from 0.41 to 2.64 mg/g with methanol.
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Cassia grandis trypsin inhibitor (CgTI) is a novel plant serine proteinase inhibitor. This study sets out to purify a thermostable inhibitor from the seeds of Cassia grandis and to provide biochemical information about a novel peptide belonging to the Kunitz family. Moreover, toxicity assays against Artemia, Aedes aegypti larvae-L4 and Nasutitermes corniger are evaluated. The purification process was performed using acetone precipitation, Trypsin-Sepharose-CL4B and Superdex-G75. The inhibitor showed an apparent molecular mass of around 19.8 kDa on Superdex-G75 gel filtration, and a mass of around 19.0 kDa visualized by SDS-PAGE under reducing conditions, and it also showed the protein consists of two polypeptide chains. N-terminal sequencing by Edman's degradation of 16 residues revealed a sequence of amino acids SVVLDTSGEPIRNGGG. 2D-electrophoresis identified a pI value of 6.3 and a 1:1 stoichiometric ratio was noted during CgTI-trypsin complex formation. The inhibitor retained the inhibitory activity over a broad range of pH (5-10) and showed thermostable activity at temperatures 30-80 °C. Furthermore, in vivo assays showed no lethality effect against Artemia and Aedes aegypti larvae, but mortality against Nasutitermes corniger with termiticidal activity LC50 of 0.685 mg/mL on workers and 0.765 mg/mL on soldiers. Preliminary investigations of CgTI revealed it to be a promising biotechnological and biomedical candidate.
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Vicia faba L. pods are a by-product generated from the industrial processing of beans for human and animal consumption. As phenolic compounds may play important roles in health, the present work envisaged the phenolic characterization of seven European varieties and cultivars of V. faba (major and minor) pods and the assessment of their antioxidant activity. The V. faba methanolic extracts were characterized by HPLC-DAD-MS/MS for identification of polyphenolic compounds. The total phenolic content and antioxidant capacity of the extracts were evaluated by colorimetric methods (Folin-Ciocalteu, DPPH scavenging capacity assay, and FRAP assay). Main compounds identified by HPLC-DAD-MS/MS were derivatives of caffeic acid, coumaric acid and kaempferol. The broad bean Jögeva variety presented the highest content of free and esterified phenolics (26.3 and 26.7 mg 100 g-1 dry weight, respectively), followed by the horse bean varieties Bauska and Lielplatones. These results were corroborated by the analysis of total phenolic content, DPPH scavenging capacity and FRAP. This study confirmed the rich phenolic content of V. faba pods suggesting to be an interesting novel source for animal nutrition, promoting product quality and consumers' health.
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Introduction: Cassia grandis Lf fruits are ethnobotanically used for digestive disorders, anemia, and for reducing blood glucose. However, there are no studies about the antidiabetic activity nor the oral toxicity of the plant fruit-extracts. This paper aims to evaluate the hypoglycemic effect of C. grandis fruits extract in vivo, and assess the acute oral toxicity, and sub-acute oral toxicity. The antioxidant activity and the α-glycosidase inhibitor effect were also evaluated. Methods: The extract was obtained by maceration of the fruit pulp with 70% hydroalcoholic solution (1:2, m:v). The extractive solution was concentrated in a vacuum rotary evaporator, up to a drug: solvent ratio of 2:1 (g/ml). Soluble solids, relative density, refractive index, pH, total phenolics, and flavonoids were determined. A preliminary phytochemical screening was made, followed by the quantitation of volatiles by GC/MS. The acute and sub-acute oral toxicity was evaluated in Sprague Dawley rats, by using biochemical and hematological parameters. The radical scavenging activity (DPPH, ABTS) and α-glycosidase inhibitory effect were tested. The hypoglycemic effect was assessed in alloxan-induced diabetic rats. Results: The extract of C. grandis contains alkaloids, coumarins, flavonoids, free amino acids, amines, phenols, tannins, reduced sugars, resins, saponins, steroids, and triterpenes, plus 38 volatile compounds, being linalool the most abundant (1,66%). The extract exhibited an LD50 > 2000 mg/kg, and after a continuous administration (1000 mg/kg, 28-days), the hematological and biochemical parameters were normal. The extract showed hypoglycemic effect, being the dose 200 mg/kg no statistically different from glibenclamide at 25 mg/kg. Good antioxidant activity and a potent α-glycosidase inhibitory effect were also observed. Conclusion: C. grandis extract is an excellent hypoglycemic and non-toxic plant product. The hypoglycemic mechanism could be associated with the antioxidant effect and with the α-glycosidase inhibition. Up to the best of our knowledge, this is the first report on the hypoglycemic effect in vivo of C. grandis fruits extract.
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The extraction of bioactive compounds from Lippia citriodora leaves (Lc) has been evaluated by comparison between Pressurized Liquid Extraction (PLE) and conventional extrations combined with HPLC-ESI-TOF-MS in order to maximize recovery of phytochemicals and to know the efficiency of both methods. To achieve these goals, conventional extractions were carried out using different concentrations of ethanol and water. On the other hand, pressurized liquid extractions were performed by a Response Surface Methodology (RSM) based on a Central Composite Design 2³ model to address the bioactive compounds extraction. The independent variables selected were temperature, percentage of solvent (ethanol and water) and extraction time. The response variables were extraction yield and recovery of bioactive compounds. Thus, the optimum values to maximize yield was 200 °C, 46% ethanol and 17 min. In addition, the design versatility allowed found the optimal conditions for each chemical group and to validate them. This experimental model followed by HPLC-ESI-TOF/MS analysis offer for the first time an easy, rapid, and objective manner to optimize extraction of bioactive compounds from Lc leaves by PLE, which could be used as methodology for development functional ingredients.
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Ethnopharmacological relevance: Cassia abbreviata is a small to medium sized branched umbrella-shaped deciduous tree. It is widely spread in the tropics, especially in Africa, having a long history in traditional medicine for the treatment of numerous conditions such as headaches, diarrhea, constipation, some skin diseases, malaria, syphilis, pneumonia, stomach troubles, uterine pains, and against gonorrhea. Aim of the study: We investigated the phytochemical constituents of a root extract from Cassia abbreviata using HPLC-PDA-ESI-MS/MS. We also determined the antioxidant activities in vitro and in vivo using the nematode Caenorhabditis elegans as a model organism. The hepatoprotective activities in case of D-galactosamine (D-GaIN)-induced hepatotoxicity were studied in a rat model. Materials and methods: HPLC-PDA-ESI-MS/MS analysis allowed the identification of the secondary metabolites of the methanol extract. DPPH and FRAP assays were used to determine the antioxidant activities in vitro. Using the C. elegans model, survival rates under juglone induced oxidative stress, intracellular ROS content, quantification of Phsp-16.2: GFP expression and subcellular DAF-16: GFP localization were investigated to determine the antioxidant activities in vivo. The in vivo hepatoprotective potential of the root extract was evaluated for D-galactosamine (D-GaIN)-induced hepatotoxicity in rats. The activity of the liver enzymes alanine aminotransferase (ALT), aspartate aminotransferase (AST) and gamma-glutamyltransferase (GGT), in addition to liver peroxidation product malondialdehyde (MDA) and glutathione content (GSH) as well as albumin and total bilirubin concentration were determined. A histopathological study was also performed. Results and conclusion: C. abbreviata root extract is rich in polyphenolics, particularly proanthocyanidins. HPLC-PDA-ESI-MS/MS analysis resulted in the identification of 57 compounds on the bases of their mass spectra. (epi)-Catechin, (epi)-afzelechin, (epi)-guibourtinidol, and (ent)-cassiaflavan monomers as well as their dimers, trimers, and their diastereomers are the main components of the extract. The total phenolic content amounted for 474mg/g root extract expressed as gallic acid equivalent using the Folin-Ciocalteu method. The extract exhibited powerful antioxidant activity with EC50 of 6.3μg/mL in DPPH and 19.15mM FeSO4 equivalent/mg sample in FRAP assay. In C. elegans model the extract (200μg/mL) was able to increase the survival rate by 44.56% and reduced the ROS level to 61.73%, compared to control group. Pretreatment of rats with 100mg extract/kg (b. wt.) reduced MDA by 47.36% and elevated GSH by 59.1%. The extract caused a significant reduction of ALT, AST and GGT activities by 11, 35.7 and 65%, respectively. The findings of this study suggest that the proanthocyanidin-rich extract from C. abbreviata may be an interesting candidate for hepatoprotective activity in case of hepatocellular injury.
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Galactomannan extracted from Cassia grandis seeds was used for the production of films containing different concentrations of the bioactive compounds lactoferrin (LF), bioactive peptides (BAPs), and phytosterols. SEM, FTIR, mechanical and thermal properties, colour, moisture content (MC), solubility, water vapour permeability (WVP), and contact angle (CA) were performed evaluating the effect of increasing concentrations of bioactive compounds on the films' physicochemical properties. The immobilization of bioactive compounds leads to films with roughness on their surface, as observed by SEM. The thermal events demonstrated that bioactive compounds avoided the establishment of more hydrogen bonds when compared to galactomannan control film; this behaviour was also confirmed by FTIR. All the studied films had a strong whiteness tendency as well as a yellowish appearance. The addition of Lf reduced MC and solubility values and leads to an increase of WVP and CA values, while the addition of BAPs and phytosterols did not changed the filmś solubility. The mechanical properties were affected by the addition of bioactive compounds, which improved the stiffness of the films. Galactomannan-based films from C. grandis showed to be a promising structure for the immobilization of biomolecules, pointing at a significant number of possible applications in food and pharmaceutical industries.
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Chemical investigation of Cassia grandis leaves resulted in the isolation of the new 2-methoxy 6,7,216'-tetrahy-droxy flavanone 6-O-beta-glucoside together with the known flavonol glycosides, kaempferol-3-O-alpha-rhamnoside, and quercetin 3-O-alpha-rhamnoside. The structure assignments were based on conventional analytical methods and confirmed by HRFTESIMS, H-1 and C-13 NMR, COSY, HSQC and HMBC data. The total phenolic content of the extract was estimated by Folin-Ciocalteu's method. The antioxidant capacity was investigated using DPPH radical scavenging assay. The ethyl acetate and the n-butanol fractions showed poor cytotoxic activity only at high concentrations against the three different cancer cell lines, hepatocellular (HepG-2), breast (MCF-7), and prostate (PC3) by the neutral red uptake assay.
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The present study deals with the phytochemical, antioxidant and anti microbial activities of two medicinal plants, namely, Cassia tora and Trichodesma indicum. Choloroform, ethyl acetate, ethanol and hydroethanolic solvents were used to extract the phytochemicals present in these two plants. The extracts were studied for the presence of different phytochemicals. Further, the antioxidant and antimicrobial properties of these extracts were studies following standard procedures. It was found that tannins, steroids and triterpinoids were present in all the extracts of both the plants whereas flavonoids, anthraquinones, cardiac glycosides, proteins, amino acids were absent in all the extracts of both plants. Cassia tora indicated more antibacterial and antifungal activities as compared to Trichodesma indicum. The antioxidant property of Trichodesma indicum was interestingly more as compared to Cassia tora. Further study on these parameters will be useful to develop medicines with these plant extracts to avoid the use of chemicals as drugs. © 2016, International Journal of Pharmacy and Technology. All rights reserved.
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It is an effort of making the analysis of the five species which are Cassia obtusifolia, Cassia auriculata, Tephrosia purpurea, Centella asiatica and Helictres isora. Ethanolic extract of leaves, stem, seeds and roots of Cassia obtusifolia and Cassia auriculata revealed the presence of alkaloids, flavonoids, tannins and anthroquinones while, it is found that the saponins were absent. Phytochemical analysis in the ethanolic leaf extract of Centella asiatica and Tephrosia purpurea showed the presence of flavonoids, tannins, saponins, while alkaloids were absent. The phytochemical constituents like tannins, flavonoids, anthroquinones and saponins were not detected, while, only alkaloids were detected in the ethanolic extract of fruit material of Helictres isora. The study establishes some concordance between the local medicinal applications of the plants investigated and their constituent phytochemical groups which are relevant to the pharmaceutical industry. The experiment carried out by using different plant parts of the plants revealed the presence of different types of phytochemical constituents.
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In this research, a non-selective extraction procedure followed by a RP-HPLC–ESI–QTOF/MS2 method was applied to evaluate the metabolic profile of these extracts, allowing the identification of a total of 95 compounds belonging to the chemical classes of organic acids, polyphenols, fatty acid derivatives, and others, most of these being identified for the first time in these extracts. These proved far richer in polyphenols, and more specifically in proanthocyanidins. This methodology successfully detected from monomers up to dimers of (epi)catechin, (epi)gallocatechin, and (epi)afzelechin units with one or two galloyl residues. A very high degree of galloylation was found, which may serve in the bioactivity attributed to these extracts. The chromatographic method had sufficient resolving power to separate up to six isomeric forms of several compounds, and the structure of some of these isomeric compounds has been elucidated. Therefore, the methodology applied proved useful for the metabolite profiling of Sclerocarya birrea stem–bark extracts, providing essential information that could be used to explain the plethora of ethnotherapeutic properties and pharmacological actions that have been attributed to this African tree.
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Phenolic compounds are secondary metabolites widely found in fruits, mostly represented by flavonoids and phenolic acids. The growing interest in these substances is mainly because of their antioxidant potential and the association between their consumption and the prevention of some diseases. The health benefits of these phytochemicals are directly linked to a regular intake and their bioavailability. Studies have shown the importance of the regular consumption of fruits, especially for preventing diseases associated with oxidative stress. In the present review, the most recent articles dealing with polyphenols in fruits are reviewed, focusing on their occurrence, main methods of extraction, quantification and antioxidant assays. In addition, the health benefits and bioaccessibility/bioavailability of phenolic compounds in fruits are addressed.
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The natural flavonoids, especially their glycosides, are the most abundant polyphenols in foods and have diverse bioactivities. The biotransformation of flavonoid aglycones into their glycosides is vital in flavonoid biosynthesis. The main biological strategies that have been used to achieve flavonoid glycosylation in the laboratory involve metabolic pathway engineering and microbial biotransformation. In this review, we summarize the existing knowledge on the production and biotransformation of flavonoid glycosides using biotechnology, as well as the impact of glycosylation on flavonoid bioactivity. Uridine diphosphate glycosyltransferases play key roles in decorating flavonoids with sugars. Modern metabolic engineering and proteomic tools have been used in an integrated fashion to generate numerous structurally diverse flavonoid glycosides. In vitro, enzymatic glycosylation tends to preferentially generate flavonoid 3- and 7-O-glucosides; microorganisms typically convert flavonoids into their 7-O-glycosides and will produce 3-O-glycosides if supplied with flavonoid substrates having a hydroxyl group at the C-3 position. In general, O-glycosylation reduces flavonoid bioactivity. However, C-glycosylation can enhance some of the benefits of flavonoids on human health, including their antioxidant and anti-diabetic potential.
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Flavonoids, which are polyphenolic compounds, are a class of plant secondary metabolites possessing a broad spectrum of pharmacological activity including anti-cancer activities. They have been reported to interfere in the initiation, promotion and progression of cancer by modulating different enzymes and receptors in signal transduction pathways related to cellular proliferation, differentiation, apoptosis, inflammation, angiogenesis, metastasis and reversal of multidrug resistance. Due to their multiple molecular mechanisms of action, flavonoids (both natural and synthetic analogues) are being investigated for their potential applications in anti-cancer therapies. In this review article, the main molecular mechanisms of action of flavonoids attributing to their potential anti-cancer activities have been discussed and the key structural features required for their activity are highlighted.
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Industrial Crops and Products j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / i n d c r o p a b s t r a c t The structures of condensed tannin from Pinus brutia bark were characterized by means of GC–MS, solid and liquid state 13 C NMR and MALDI-TOF MS analyses. The results indicated that the monomeric units building up the condensed tannin of brutia pine bark are mainly composed of catechin/epicatechin, gallo-catechin/epigallocatechin units accompanied by possibly tri-or tetra hydroxyl-flavanols. Some oligomers appear to present p-hydroxy-or 3,4-dihydroxy benzoic acid residues or glucose at their terminal unit. Apart from oligomers, monomeric flavanoids were also present in the brutia bark extract. Taxifolin was especially found in appreciable amounts. Additionally, in this tannin procyanidin oligomers predom-inated while prodelphinidin units were present to a lesser extent. The NMR results showed that the oligomers in brutia pine bark tannin Exhibit 2,3-cis stereochemistry and C4–C6 bonds with a notice-able portion of C4–C8 interflavonoid links being present. The MALDI-TOF MS showed a series of peaks corresponding to flavonoid hexamers of the condensed tannin (1750 Da).
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Litchi (Litchi chinensis Sonn.) is widely accepted as a delicious fruit in China and its seeds have been commonly used in traditional Chinese medicine to relieve neuralgic pain. In the present study, chemical investigation of the 95% ethanol extract of Litchi chinensis seeds led to the isolation of four new compounds, 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β-8-catechin) (5), 2β,3β-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4α-8-epicatechin) (7), litchiol A (9) and litchiol B (12), together with 11 known ones, 2,5-dihydroxy-hexanoic acid (1), soscopoletin (2), coumaric acid (3), protocatechuic acid (4), 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β−8)-epicatechin (6), pterodontriol d-6-O-β-d-glucopyranoside (8), Narirutin (10), naringin (11), dihydrocharcone-4′-O-β-d-glucopyranoside (13), pinocembrin-7-rutinoside (14), pinocembrin-7-neohesperidoside (15). Their structures were mainly elucidated on the basis of NMR, MS, IR, CD and UV spectral evidences. Antioxidant activities of 14 compounds were determined by DPPH radical-scavenging assay and Trolox equivalent antioxidant capacity assay, and the results showed that four compounds, protocatechuic acid (4), 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β-8-catechin (5), 2α,3α-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4β−8)-epicatechin (6), 2β,3β-epoxy-5,7,3′,4′-tetrahydroxyflavan-(4α-8)-epicatechin (7), exhibited moderate antioxidant activities.