Extraction of Bioactive Compounds from the Fruits of Jambolan (Syzygium cumini (L.)) Using Alternative Solvents.

This work demonstrates the effectiveness of using alternative solvents to obtain jambolan extracts with a high content of bioactive compounds compared to conventional organic solvents, being the first study to evaluate the best ecological solvent alternative for Syzygium cumini (L.) Skeels. Five alternative solvents were used for extraction: water at 25 °C (W25), water at 50 °C (W50), water at 75 °C (W75), water with citric acid at 2.4% (CA2), and water with citric acid at 9.6% (CA9) in comparison with three conventional solvents: ethanol (EtOH), water with ethanol at 50% (WE), and water with methanol at 50% (WM). A protocol was then established for the extraction and concentration of samples obtained with these solvents. The highest content of total phenolic compounds (TPCs) in the extracts was obtained with the solvent W75 (1347.27 mg GAE/100 g), while in the concentrates it was the solvents EtOH (3823.03 mg GAE/100 g) and WM (4019.39 mg GAE/100 g). Total monomeric anthocyanins (TMAs) increased by 209.31% and 179.95% in extractions with CA2 and CA9, respectively, compared to pulp (35.57 mg eq c-3-g/100 g), demonstrating that they are the most efficient alternative solvents in this extraction. The levels of bioactive compounds and antioxidant activity varied according to the solvents used. Delphinidin 3,5-diglucoside, cyanidin 3,5-diglucoside, delphinidin 3-glucoside, petunidin 3,5-diglucoside, cyanidin 3-glucoside, peonidin 3,5-diglucoside, malvidin 3,5-diglucoside, petunidin 3-glucoside, and malvidin 3-glucoside were identified in most of the samples by UPLC-MS/MS. This study suggests that a simple procedure using alternative solvents can be used as an environmentally friendly strategy to achieve efficient extraction of bioactive compounds in jambolan.

Efficiency of Different Solvents in the Extraction of Bioactive Compounds from Plinia cauliflora and Syzygium cumini Fruits as Evaluated by Paper Spray Mass Spectrometry.

Jabuticaba (Plinia cauliflora) and jambolan (Syzygium cumini) fruits are rich in phenolic compounds with antioxidant properties, mostly concentrated in the peel, pulp, and seeds. Among the techniques for identifying these constituents, paper spray mass spectrometry (PS-MS) stands out as a method of ambient ionization of samples for the direct analysis of raw materials. This study aimed to determine the chemical profiles of the peel, pulp, and seeds of jabuticaba and jambolan fruits, as well as to assess the efficiency of using different solvents (water and methanol) in obtaining metabolite fingerprints of different parts of the fruits. Overall, 63 compounds were tentatively identified in the aqueous and methanolic extracts of jabuticaba and jambolan, 28 being in the positive ionization mode and 35 in the negative ionization mode. Flavonoids (40%), followed by benzoic acid derivatives (13%), fatty acids (13%), carotenoids (6%), phenylpropanoids (6%), and tannins (5%) were the groups of substances found in greater numbers, producing different fingerprints according to the parts of the fruit and the different extracting solvents used. Therefore, compounds present in jabuticaba and jambolan reinforce the nutritional and bioactive potential attributed to these fruits, due to the potentially positive effects performed by these metabolites in human health and nutrition.

Characterization of odor-active volatile compounds of jambolan [Syzgium cumini (L.) Skeels] wine.

Volatile constituents in jambolan [Syzgium cumini (L.) Skeels] wine were isolated by headspace-solid phase microextraction (HS-SPME) and analyzed by gas chromatography-flame ionization detector (GC-FID), gas chromatography-mass spectrometry (GC-MS), and gas chromatography-olfactometry (GC-O). The composition of the jambolan wine included 52 esters, 20 terpenes, 13 alcohols, 12 acids, 11 aldehydes, 4 ketones, 4 oxides, and 5 miscellaneous compounds. Aroma extract dilution analysis and odor activity units were used for the determination of odor-active compounds. A total of 19 odor-active compounds were found as odor-active volatiles, from which (E)-ß-ionone, phenylacetaldehyde, ethyl acetate, ethyl hexanoate, and ethyl benzoate were the most important. The similar results of the GC-O and OAV approaches suggests that HS-SPME-GC-O could be used as a fast and simple tool to quality control of the jambolan wine aroma.

Antidiabetic effects of Syzygium cumini leaves: A non-hemolytic plant with potential against process of oxidation, glycation, inflammation and digestive enzymes catalysis.

ETHNOPHARMACOLOGICAL RELEVANCE: Plant materials are commonly used in traditional medicine in order to treat various diseases such as Diabetes mellitus. Some plants, such as Syzygium cumini, have the capability to act controlling oxidative stress and protein glycation besides their potential to decrease hyperglycemia and hyperlipidemia by the inhibition of the catalysis of digestive enzymes. The aim of this study was to evaluate the antioxidant and antiglicant activity of S. cumini leaves fractions, their capacity to inhibit hydrolases and lipase enzymes, as well as the cytotoxicity effects against erythrocytes and comparate these results with isolate quercetin flavonoid. MATERIAL AND METHODS: Ethnobotanical researches, carried out by academic studies at the Federal University of Uberlandia, led us to choose S. cumini as a potential plant for treatment of Diabetes mellitus. Fractions from ethanolic extract of S. cumini (hexane/Hex, dichloromethane/DCM, ethyl acetate/EtOAc, n-butanol/ButOH and water/H2O) were used to evaluate their antioxidant (DPPH, ORAC and FRAP) and antiglycant (BSA/fructose, BSA/methylglyoxal and Arginine/Methylglyoxal) activity as well as the inhibitory potential against α-amylase, α-glucosidase and lipase. In addition, identification of the main bioactive compounds of S. cuimini leaves by HPLC-ESIMS/MS analysis was carried out. RESULTS: Our results indicate that all fractions, for exception Hex, present noteworthy antioxidant activity, mainly in EtOAc and ButOH fractions (FRAP 1154.49 ± 67.37 and 1178.27 ± 21.26 µmol trolox eq g-1, respectively; ORAC 1224.63 ± 58.16 and 1313.53 ± 85.23 µmol trolox eq g-1, respectively; DPPH IC50 15.7 ± 2.4 and 23.5 ± 2.7 µg mL-1, respectively). Regarding the antiglycant activity (BSA/fructose and Arginine/Methylglyoxal models), all fraction, for exception Hex, presented inhibition higher than 85%. All fractions were capable to inhibit 100% of α-amylase and the fractions DCM, EtOAc and ButOH inhibited α-glucosidase more than 50%. Regarding the lipase assay, DCM and Hex had the best activity (31.5 ± 14.3 and 44.3 ± 4.5 µg mL-1, respectively). Various biomolecules known as potent antioxidants were identified in these fractions, such as quercetin, kaempferol, luteolin and (Epi)catechin. CONCLUSION: S. cumini fractions and quercetin presented promising antioxidant and antiglycation properties as well as the ability to inhibit digestive enzymes. This study presents new biological activities not yet described for S. cumini which provide new possibilities for further studies in order to assess the antidiabetic potential of S. cumini fractions especially EtOAc and ButOH.

Polyphenol-Rich Extract of Syzygium cumini Leaf Dually Improves Peripheral Insulin Sensitivity and Pancreatic Islet Function in Monosodium L-Glutamate-Induced Obese Rats.

Syzygium cumini (L.) Skeels (Myrtaceae) has been traditionally used to treat a number of illnesses. Ethnopharmacological studies have particularly addressed antidiabetic and metabolic-related effects of extracts prepared from its different parts, especially seed, and pulp-fruit, however. there is a lack of studies on phytochemical profile and biological properties of its leaf. As there is considerable interest in bioactive compounds to treat metabolic syndrome and its clustered risk factors, we sought to characterize the metabolic effects of hydroethanolic extract of S. cumini leaf (HESc) on lean and monosodium L-glutamate (MSG)-induced obese rats. HPLC-MS/MS characterization of the HESc polyphenolic profile, at 254 nm, identified 15 compounds pertaining to hydrolysable tannin and flavanol subclasses. At 60 days of age, both groups were randomly assigned to receive HESc (500 mg/kg) or vehicle for 30 days. At the end of treatment, obese+HESc exhibited significantly lower body weight gain, body mass index, and white adipose tissue mass, compared to obese rats receiving vehicle. Obese rats treated with HESc showed a twofold increase in lipolytic activity in the periepididymal fat pad, as well as, brought triglyceride levels in serum, liver and skeletal muscle back to levels close those found in lean animals. Furthermore, HESc also improved hyperinsulinemia and insulin resistance in obese+HESc rats, which resulted in partial reversal of glucose intolerance, as compared to obese rats. HESc had no effect in lean rats. Assessment of ex vivo glucose-stimulated insulin secretion showed HESc potentiated pancreatic function in islets isolated from both lean and obese rats treated with HESc. In addition, HESc (10-1000 µg/mL) increased glucose stimulated insulin secretion from both isolated rat islets and INS-1E ß-cells. These data demonstrate that S. cumini leaf improved peripheral insulin sensitivity via stimulating/modulating ß-cell insulin release, which was associated with improvements in metabolic outcomes in MSG-induced obese rats.

Correlación del contenido de fenoles y antocianinas con la capacidad antioxidante Syzygium cumini (L. ) Skeels, (jambolan) / Phenol and anthocyanin content and correlation with the antioxidant capacity of Syzygium cumini (L.) Skeels, (jambolan)

Introducción: la especie Syzygium cumini (L.) Skeels, (jambolam), sin. Eugenia jambolana L, es una planta rica en metabolitos secundarios con un elevado potencial biológico, medicinal, entre otros y que pueden estar asociados con las propiedades terapéuticas reportadas para S. cumini. Objetivo: comparar capacidad antioxidante de extractos del fruto, pulpa y semilla de S. cumini, con respecto al contenido de polifenoles y antocianinas. Métodos: fruto, pulpa y semillas S. cumini deshidratados y macerados se sometieron a extracción sólido-líquido; el contenido de fenoles se evaluó por el método de Folin-Ciocalteu, el de antocianinas por el método de diferencial de pH y el potencial antioxidante in vitro se evaluó con base en los métodos del radical estable 1,1-difenil­2-picrilhidracil, el radical catión 2,2´-azino-bis(3-etilbenzotiazolin-6-sulphonic ácido) y poder antioxidante de reducción del ion férrico. Resultados: el contenido de fenoles obtenidos tanto en los extractos metanólicos como etanólicos fue muy similar en fruto y pulpa, mientras que en las semillas se observó un incremento hasta 5 veces con respecto a la pulpa, presentó correlación con el efecto de protección antioxidante entre los extractos evaluados. Conclusiones: la elevada presencia de fenoles determinada en todos los extractos afectó de manera positiva la capacidad protectora contra radicales libres, y los frutos de S. cumini, podrían ser considerados como una fuente potencial de compuestos biaoctivos con aplicaciones terapéuticas(AU)

Introduction: Syzygium cumini (L.) Skeels, (jambolam), sin. Eugenia jambolana L, is considered as a source of secondary metabolites with a biological and medicinal potential and these can be associated with its therapeutics properties. Objetive: to correlated the content of polyphenols and anthocyanins with antioxidant capacity in ethanolic and methanolic extracts of S. cumini. Methods: dehydrated and powered fruits, pulp and seeds of S. cumini was subjected to solid-liquid extraction. Total phenolis content was determined by Folin-Cicoulteau method, anthocyanin content was determined by the pH differential method and the potential antioxidant was evaluated using 1,1-difenil­2-picrilhidracil radical stable, 2,2´-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid radical cation and ferric reducing/antioxidant power tests. Results: all extracts showed an important correlation between total phenolis content and antioxidant capacity values, however, in the seed total phenolis content was almost 5 times higher than that obtained in fruit and pulp. Conclusions: all extracts exhibited a considerable antioxidant potential against free radical, and S. cumini could be used as an alternative source of natural bioactive compounds with application in therapeutic research area(AU)

In vitro antibacterial and non-stick activity of extracts from leaves of Psidium guineense Sw. and Syzygium cumini (L.) Skeels on oralmicroorganisms / Atividade antibacteriana e antiaderente in vitro dos extratos das folhas de Psidium guineense Sw. e Syzygium cumini (L.) Skeels sobre microrganismos orais

Objective: This study determined the Minimum Inhibitory Concentration and the Minimum Inhibitory Concentration of Adherence of hydroalcoholic extracts of the leaves of strawberry guava (Psidium guineense Sw.) and of the jambolan (Syzygium cumini (L.) Skeels) against Streptococcus mutans (ATCC 25175), Streptococcus oralis (ATCC 10557), Streptococcus parasanguis (ATCC 903), Streptococcus salivarius (ATCC 7073), Streptococcus sp (ATCC 15300), and Lactobacillus casei (ATCC 9595). Methods: Strains were seeded on blood agar plates to determine the Minimum Inhibitory Concentration by the agar-diffusion technique. The inclined tubes technique was used for Minimum Inhibitory Concentration of Adherence evaluation in the presence of 5% of sucrose, in Mueller-Hinton broth. The same procedures were accomplished with the 0.12% chlorhexidine digluconate (positive control). Assays were performed in duplicate. The plates and the tubes were maintained in microaerophillia at 37ºC for 24 hours. Results: The Minimum Inhibitory Concentration obtained for strawberry guava extract ranged from 275 to 1100 mg.ml-1. Jambolan values were 242.5 to 485 mg.mL-1; and 0.12% chlorhexidine digluconate were 75x10-3 to 9x10-3 mg.ml-1. The Minimum Inhibitory Concentration of Adherence reported the following values : strawberry guava (1.81 to 28.94 mg.ml-1); jambolan (1.60 to 12.76 mg.ml-1) and 0.12% chlorhexidine didigluconate (4.93 x10-4 to 19.70 x10-4 mg.ml-1). Conclusion: It was concluded that the hydroalcoholic extracts from the leaves of P. guineense Sw. and S. cumini (L.) Skeels presented antimicrobial and nonstick effect on the tested lineages; further studies are needed to confirm these extracts to be natural antibacterial agents for use in controlling dental caries.

Objetivo: Determinar a Concentração Inibitória Mínima e a Concentração Inibitória Mínima de Aderência dos extratos hidroalcoólicos das folhas do araçá (Psidium guineense Sw.) e do jambolão (Syzygium cumini (L.) Skeels) frente à Streptococcus mutans (ATCC 25175), Streptococcus oralis (ATCC 10557), Streptococcus parasanguis (ATCC 903), Streptococcus salivarius (ATCC 7073), Streptococcus sp (ATCC 15300) e Lactobacillus casei (ATCC 9595). Métodos: As cepas foram semeadas em placas de ágar sangue para determinação da CIM pela técnica de ágar-difusão. Utilizou-se a técnica dos tubos inclinados para avaliação da Concentração Inibitória Mínima de Aderência ao vidro, na presença de 5% de sacarose, em caldo Mueller-Hinton. Os mesmos procedimentos foram realizados com o digluconato de clorexidina à 0,12% (controle positivo). Os ensaios foram realizados em duplicata. As placas e os tubos foram mantidos em microaerofilia a 37ºC por 24 horas. Os dados foram analisados descritivamente. Resultados: As Concentrações Inibitórias Mínimas obtidas para o extrato do araçá variaram de 275 a 1100 mg.ml-1. Para o extrato do jambolão apresentaram valores de 242,5 a 485 mg.ml-1. E quanto ao digluconato de clorexidina à 0,12% foram de 9x10-3 a 75x10-3 mg.ml-1. Quanto às Concentrações Inibitórias Mínimas de Aderência, registrou-se os seguintes valores: araçá (1,81 a 28,94 mg.ml-1); jambolão (1,60 a 12,76 mg.ml-1) e digluconato de clorexidina à 0,12% (4,93x10-4 a 19,70x10-4 mg.ml-1). Conclusão: Conclui-se que os extratos hidroalcoólicos das folhas de P. guineense Sw. e S. cumini (L.) Skeels apresentaram efeito antimicrobiano e antiaderente sobre as linhagens testadas, sendo necessários estudos complementares que confirmem ser estes extratos alternativas de antibacterianos naturais no controle da cárie dentária.

Atividade antibacteriana de extrato hidro-alcoólico de folhas de jambolão (Syzygium cumini (L.) Skells)

The antimicrobial activity of medicinal plants has been searched in diverse species, as much in Brazil as in other countries. The aim of this study was to evaluate the existence of hydro-alcoholic extract jambolan leaves 10% (w/v) antibacterial effect. Seventeen Gram positive and Gram negative isolated bacterial were used. The antibacterial action was evaluated through the inoculation of Mueller Hinton agar plates, with a bacterial inoculate of 3x10(8) cell/ mL, with four paper discs, being the first of commercial antimicrobial and the others embedded with 25mL of the extract, saline or ethanol. The plates were incubated at 37°C for 24 hours, and their reading of inhibition hales diameter was done. The extract inhibited the growth of 100% of the tested bacteria; the Gram positive isolates had presented an average hale of 19.5mm, while of the Gram negative was of 18.8mm. There was not significant inhibition of growth in treatments with saline and ethanol. As verified in this study, the tested extract presents antibacterial activity against all the isolates, without sensitivity difference among Gram positive and Gram negative microorganisms.

A atividade antimicrobiana de plantas medicinais tem sido pesquisada em diversas espécies, tanto no Brasil quanto em outros países. O objetivo deste trabalho foi o de avaliar a existência de efeito antibacteriano de extrato hidro-alcoólico a 10% (m/v) de folhas de jambolão. Utilizaram-se 17 isolados bacterianos, Gram positivos e Gram negativos. A ação antibacteriana foi avaliada através da inoculação de placas de ágar Mueller Hinton, com um inóculo bacteriano de 1x10(6) ufc mL-1, onde se colocaram quatro discos de papel; o primeiro de antimicrobiano comercial e os demais embebidos em 25mL do extrato, de solução salina ou de etanol. As placas foram incubadas a 37°C por 24 horas, sendo posteriormente realizada a leitura do diâmetro dos halos de inibição. O extrato inibiu o crescimento de 100% das bactérias testadas e os isolados Gram positivos apresentaram um halo médio de 19,5mm, enquanto o dos Gram negativos foi de 18,8mm. Não houve inibição significativa de crescimento nos tratamentos com salina e etanol. Conforme os resultados deste estudo, o extrato testado apresenta atividade antibacteriana frente às amostras testadas, sem diferença de sensibilidade entre microrganismos Gram positivos e Gram negativos.

Atividade antibacteriana de extrato hidro-alcoólico de folhas de jambolão (Syzygium cumini (L.) Skells)

The antimicrobial activity of medicinal plants has been searched in diverse species, as much in Brazil as in other countries. The aim of this study was to evaluate the existence of hydro-alcoholic extract jambolan leaves 10% (w/v) antibacterial effect. Seventeen Gram positive and Gram negative isolated bacterial were used. The antibacterial action was evaluated through the inoculation of Mueller Hinton agar plates, with a bacterial inoculate of 3x10(8) cell/ mL, with four paper discs, being the first of commercial antimicrobial and the others embedded with 25mL of the extract, saline or ethanol. The plates were incubated at 37°C for 24 hours, and their reading of inhibition hales diameter was done. The extract inhibited the growth of 100% of the tested bacteria; the Gram positive isolates had presented an average hale of 19.5mm, while of the Gram negative was of 18.8mm. There was not significant inhibition of growth in treatments with saline and ethanol. As verified in this study, the tested extract presents antibacterial activity against all the isolates, without sensitivity difference among Gram positive and Gram negative microorganisms.

A atividade antimicrobiana de plantas medicinais tem sido pesquisada em diversas espécies, tanto no Brasil quanto em outros países. O objetivo deste trabalho foi o de avaliar a existência de efeito antibacteriano de extrato hidro-alcoólico a 10% (m/v) de folhas de jambolão. Utilizaram-se 17 isolados bacterianos, Gram positivos e Gram negativos. A ação antibacteriana foi avaliada através da inoculação de placas de ágar Mueller Hinton, com um inóculo bacteriano de 1x10(6) ufc mL-1, onde se colocaram quatro discos de papel; o primeiro de antimicrobiano comercial e os demais embebidos em 25mL do extrato, de solução salina ou de etanol. As placas foram incubadas a 37°C por 24 horas, sendo posteriormente realizada a leitura do diâmetro dos halos de inibição. O extrato inibiu o crescimento de 100% das bactérias testadas e os isolados Gram positivos apresentaram um halo médio de 19,5mm, enquanto o dos Gram negativos foi de 18,8mm. Não houve inibição significativa de crescimento nos tratamentos com salina e etanol. Conforme os resultados deste estudo, o extrato testado apresenta atividade antibacteriana frente às amostras testadas, sem diferença de sensibilidade entre microrganismos Gram positivos e Gram negativos.