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1.
Fitoterapia ; 175: 105863, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38373500

ABSTRACT

Thirty four compounds were identified in Sorbus torminalis (L.) fruit extracts of different maturity types by means of LC-DAD-MS (ESI+) fragmentation analysis. Both immature and mature fruits were rich in flavonoid glycosides esterified with hydroxycinnamic, phenolic and dicarboxylic acids along with benzoic, phenylpropanoic and cinnamoyl quinic acid derivatives with many of them being detected for the first time in Sorbus species and in literature. Extracts and fractions were tested for their antioxidant activity (DPPH, chemiluminescence, Rancimat assays) and the estimation of the phenolic content was carried out through Folin-Ciocalteu reagent. Ethyl acetate fraction exhibited the highest scavenging activity determined as EC50 = 1.58 ± 0.22 µg/mL and EC50 = 1.64 ± 0.24 µg/mL for immature and mature fruits respectively with the DPPH test. Chemiluminescence test indicated the same fraction having the strongest antioxidant activity with an IC50 0.41 ± 0.06 µg/mL and IC50 0.50 ± 0.02 µg/mL in both maturity types. The ethyl acetate fraction of the mature fruits is considered the most potent Aldose Reductase 2 (ALR2) inhibitor with 79% demonstrating the high nutritional value of Sorbus torminalis (L.) mature fruits as a defense mechanism against the onset of diabetes mellitus secondary complications leading to the utilization of the plant for nutritional and pharmaceutical purposes.


Subject(s)
Antioxidants , Fruit , Phytochemicals , Plant Extracts , Sorbus , Fruit/chemistry , Sorbus/chemistry , Antioxidants/pharmacology , Antioxidants/isolation & purification , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Plant Extracts/pharmacology , Plant Extracts/chemistry , Molecular Structure , Phenols/pharmacology , Phenols/isolation & purification , Phenols/analysis , Flavonoids/pharmacology , Flavonoids/isolation & purification
2.
Ultrason Sonochem ; 98: 106527, 2023 Aug.
Article in English | MEDLINE | ID: mdl-37478642

ABSTRACT

Currently, sustainability is one of the most critical issues confronting society today. The growing of macroalgae in ocean farms appears more sustainable than agriculture on land due to it does not require any fresh water, chemical fertiliser, or soil. Macroalgae have been shown to be a sustainable marine source of amino acids, novel bioactive phenolic and aroma compounds that can be exploitation in food, cosmetic, nutraceuticals, pharmacological applications. Despite starting the huge cultivation of macroalgae in world, bioactive compounds in the edible macroalgae have not been well characterized. Ultrasound assisted extraction (UAE) and conventional extraction (CE) techniques were compared and red macroalgae, L. papillosa extracts were characterized. The highest amount of amino acid was glutamic acid (GLU) and composed of 35% was essential amino acids. UAE at 10% amplitude for 15 min showed significantly highest (p < 0.05) phenolic (212.03±3.03 mg gallic acid equivalent/100 g) as well as antioxidant activity determined by DPPH (105.69±3.02 µmol Trolox/100 g), ABTS (238.69±2.23 µmol Trolox/100 g) radical assay and FRAP value (72.47±3.13 µmol Trolox/100 g) when in comparison with CE. Furthermore, bioactive compounds in extracts were indicated as phlorotannins, flavonoids, phenolic acids and other polyphenols using liquid chromatography coupled to diode array detection and electrospray ionisation tandem mass spectrometry (LC-DAD-ESI-MS/MS). This result confirmed higher antioxidant capacity detected with the UAE. A total of 46 volatile organic compounds were identified and quantified by GC-FID/MS with HS-SPME system. This study emerges as first report to novel extraction method used and deeply characterization of L papillosa. The results seem that significant potential application in the functional food, active packaging and nutraceuticals industry.


Subject(s)
Laurencia , Seaweed , Antioxidants/chemistry , Tandem Mass Spectrometry , Sugars , Amino Acids , Odorants/analysis , Chromatography, High Pressure Liquid , Phenols/analysis , Carbohydrates , Plant Extracts/chemistry
3.
Prev Nutr Food Sci ; 27(2): 223-233, 2022 Jun 30.
Article in English | MEDLINE | ID: mdl-35919565

ABSTRACT

Natural compounds are a good substitute for synthetic antioxidants. Attempts have been made to characterize the antioxidant capacity of natural resources (e.g., medicinal plants). Thus, the Rheum emodi Wall was evaluated using liquid chromatography with diode array detection and electrospray ionization-mass spectrometry. Three antioxidant compounds (i.e., myricitrin, myricetin-3-galloyl rhamnoside, and myricetin) were isolated, identified, and used to screen the antioxidant capacity of the new compounds. 2,2-Diphenyl-1-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), and superoxide dismutase assay results are presented in the half-maximal inhibitory concentration values ranging 1.50∼28.46, 102.01∼137.55, and 4.06∼15.74 µg/mL, respectively. Myricetin had the highest antioxidant activity among the other compounds. A significantly positive correlation was noted between the ethyl acetate fraction and the antioxidant compound. In a partial least squares-discriminant analysis model, identified antioxidant compounds were shown to play a role in the structure of the compound and its contents based on the antioxidant activity. The study suggests that myricetin from R. emodi possesses the most potent antioxidant activity, and thus is the most efficient in extracting antioxidant contents.

4.
Molecules ; 27(13)2022 Jun 21.
Article in English | MEDLINE | ID: mdl-35807222

ABSTRACT

This study aimed to investigate the phenolic profile and selected biological activities of the leaf and aerial extracts of three Ericaceae species, namely Erica multiflora, Erica scoparia, and Calluna vulgaris, collected from three different places in the north of Morocco. The phenolic composition of all extracts was determined by LC coupled with photodiode array and mass spectrometry detection. Among the investigated extracts, that of E. scoparia aerial parts was the richest one, with a total amount of polyphenols of 9528.93 mg/kg. Up to 59 phenolic compounds were detected: 52 were positively identified and 49 quantified-11 in C. vulgaris, 14 in E. multiflora, and 24 in E. scoparia. In terms of chemical classes, nine were phenolic acids and 43 were flavonoids, and among them, the majority belonged to the class of flavonols. The antioxidant activity of all extracts was investigated by three different in vitro methods, namely DPPH, reducing power, and Fe2+ chelating assays; E. scoparia aerial part extract was the most active, with an IC50 of 0.142 ± 0.014 mg/mL (DPPH test) and 1.898 ± 0.056 ASE/mL (reducing power assay). Further, all extracts were non-toxic against Artemia salina, thus indicating their potential safety. The findings attained in this work for such Moroccan Ericaceae species, never investigated so far, bring novelty to the field and show them to be valuable sources of phenolic compounds with interesting primary antioxidant properties.


Subject(s)
Calluna , Ericaceae , Scoparia , Antioxidants/chemistry , Chromatography, Liquid , Ericaceae/chemistry , Flavonoids/chemistry , Phenols/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology
5.
Molecules ; 27(7)2022 Mar 30.
Article in English | MEDLINE | ID: mdl-35408655

ABSTRACT

Rydingia michauxii (Briq.) Scheen and V.A.Albert (Lamiaceae) is used in Iranian traditional medicine to treat malaria, diabetes, hyperlipidemia, rheumatism and cardiovascular diseases. NMR and LC-DAD-MSn analyses were used to establish extract composition and phenylethanoid, flavonoid glycosides, lignans, labdane diterpenes and iridoids were identified and quantified. The main constituents were isolated, and structures were elucidated based on NMR, polarimetric and MS measurements. A new natural compound, ent-labda-8(17),13-dien-18-glucopyranosyl ester-15,16-olide is described here. The effects of ent-labda-8(17),13-dien-18-oic acid-15,16-olide (1), ent-labda-8(17),13-dien-18-glucopyranosyl es-ter-15,16-olide (2), antirrhinoside (3), echinacoside (4), verbascoside (5), and apigenin 6,8-di-C-glucoside (6), on the low-density lipoprotein receptor (LDLR) and proprotein convertase subtilisin/kexin type 9 (PCSK9), were studied in the human hepatocarcinoma cell line Huh7. Among the six constituents, (3) showed the strongest induction of the LDLR (3.7 ± 2.2 fold vs. control) and PCSK9 (3.2 ± 1.5 fold vs. control) at a concentration of 50 µM. The in vitro observations indicated a potential lipid lowering activity of (3) with a statin-like mechanism of action.


Subject(s)
Biological Products , Lamiaceae , Liver Neoplasms , Biological Products/pharmacology , Chromatography, Liquid , Humans , Iran , Lamiaceae/metabolism , Plant Extracts/pharmacology , Proprotein Convertase 9/metabolism , Receptors, LDL/metabolism , Tandem Mass Spectrometry
6.
Molecules ; 27(6)2022 Mar 16.
Article in English | MEDLINE | ID: mdl-35335294

ABSTRACT

Products based on plants containing hydroxyanthracene derivatives (HADs)­such as Rheum, Cassia, and Aloe species­are widely used in food supplements or nutraceuticals due to their laxative effects. A more restricted control of HAD contents in food supplements has been implemented by EU Regulation 2021/468, in order to increase the safety of these preparations. Due to their toxicity, aloin A, aloin B, aloe emodin, emodin, and the synthetic derivative danthron have been listed as prohibited substances in food supplements, being tolerated in amounts < 1 mg kg−1 in marketed products. In this work, we report the development of a sensitive and fast LC−DAD−MS-based procedure for the determination of these five compounds in food supplements and plant materials or extracts. The entire procedure includes a simple sample preparation step, where target analytes are concentrated by means of solvent extraction and evaporative concentration (solid samples), or by lyophilisation (liquid samples). The average LOQ of 0.10 mg/L, LOD of 0.03 mg/L, accuracy, and precision with CVs below 12.72 were obtained for the studied analytes. This method is suitable for assessing the compliance of commercial products and raw materials with EU Regulation 2021/468. Furthermore, the proposed method can represent a starting point for the development of a unique and standardised analytical approach for the determination of other HADs under the attention of EU authorities.


Subject(s)
Aloe , Chromatography, Liquid , Dietary Supplements , Mass Spectrometry , Research Design
7.
Nat Prod Res ; 36(22): 5868-5871, 2022 Nov.
Article in English | MEDLINE | ID: mdl-35068274

ABSTRACT

Morinda citrifolia is a plant that grows in Brazilian northeast and presented a wide range of therapeutic, industrial and technological applications. Based on this, the aim of this work was to study the chemical composition, main biological activities and potential toxicity of its extracts, aiming their industrial application. Important compounds were identified in the methanolic extracts obtained by ultrasonic and Soxhlet extractions from leaves and fruits. GC × GC allowed for the identification of phytosterols, fatty acids and methyl esters, besides others (scopoletin, hydrocarbons, alcohols, terpenes). By HPLC-DAD, compounds like catechin, rutin, quercetin could be also identified and quantified. Their content of polyphenols and flavonoids was considered between the international standards. The extracts showed high antioxidant activities (EC50 ∼ 300 µg mL-1, using DPPH assay) compared with those from the literature. The extracts did not show toxicity or mutagenicity, but presented cytotoxicity, which can indicate their use safely in phytotherapic or nutritional applications.


Subject(s)
Antineoplastic Agents , Morinda , Morinda/chemistry , Fruit/chemistry , Methanol , Plant Extracts/chemistry , Plant Leaves/chemistry , Antineoplastic Agents/analysis
8.
Nat Prod Res ; 36(22): 5910-5915, 2022 Nov.
Article in English | MEDLINE | ID: mdl-35019791

ABSTRACT

Ephedra (Ephedraceae) is used in medicine for various purposes as having, antioxidant, anticarcinogen, antibacterial, anti-inflammatory hepatoprotective, anti-obesity, antiviral and diuretic activities. In this study the aim was to investigate chemical constituents of Ephedra alata and understand the possible effects of those constituents in antioxidant activity and alzheimer's disease essay. For this purpose, natural compounds from E.alata were characterized by LC-DAD-ESI-MS/MS using negative and positive ionization modes, while the bioactivity was assessed by acetylcholinesterase (AChE) inhibition study and determining of antioxidant activity; DPPH radical scavenging and ß-carotene bleaching assays were used to assess the antioxidant potential. The proposed method of spectrometry provided tentative identification of 27 compounds including alkaloids and phenolic compounds as flavonoids. The methanolic extract showed high contents of total phenolic and exhibited an important antioxidant potential and demonstrated a potent inhibitory effect against acetylcholinesterase (IC50: 11,25 ± 0,25 µg/mL). The results showed that the plant possesses a therapeutic effect.


Subject(s)
Antioxidants , Ephedra , Antioxidants/chemistry , Cholinesterase Inhibitors/chemistry , Ephedra/chemistry , Acetylcholinesterase , Chromatography, High Pressure Liquid/methods , Tandem Mass Spectrometry , Algeria , Plant Extracts/chemistry , Phenols/analysis
9.
Viruses ; 13(6)2021 06 07.
Article in English | MEDLINE | ID: mdl-34200316

ABSTRACT

Owing to the richness of bioactive compounds, Olea europea leaf extracts exhibit a range of health effects. The present research evaluated the antibacterial and antiviral effect of leaf extracts obtained from Olea europea L. var. sativa (OESA) and Olea europea var. sylvestris (OESY) from Tunisia. LC-DAD-ESI-MS analysis allowed the identification of different compounds that contributed to the observed biological properties. Both OESA and OESY were active against Gram-positive bacteria (MIC values between 7.81 and 15.61 µg/mL and between 15.61 and 31.25 µg/mL against Staphylococcus aureus ATCC 6538 for OESY and OESA, respectively). The antiviral activity against the herpes simplex type 1 (HSV-1) was assessed on Vero cells. The results of cell viability indicated that Olea europea leaf extracts were not toxic to cultured Vero cells. The half maximal cytotoxic concentration (CC50) values for OESA and OESY were 0.2 mg/mL and 0.82 mg/mL, respectively. Furthermore, both a plaque reduction assay and viral entry assay were used to demonstrate the antiviral activity. In conclusion, Olea europea leaf extracts demonstrated a bacteriostatic effect, as well as remarkable antiviral activity, which could provide an alternative treatment against resistant strains.


Subject(s)
Anti-Bacterial Agents/pharmacology , Antiviral Agents/pharmacology , Herpesvirus 1, Human/drug effects , Olea/chemistry , Plant Extracts/pharmacology , Plant Leaves/chemistry , Animals , Cell Survival , Chlorocebus aethiops , Gram-Positive Bacteria/classification , Gram-Positive Bacteria/drug effects , Herpes Simplex/drug therapy , Phytochemicals , Plant Extracts/chemistry , Vero Cells
10.
Plants (Basel) ; 10(4)2021 Apr 07.
Article in English | MEDLINE | ID: mdl-33916934

ABSTRACT

Hyssopus officinalis L. is a well-known aromatic plant used in traditional medicine and the food and cosmetics industry. The aim of this study is to assess the antioxidant, genotoxic, antigenotoxic and cytotoxic properties of characterized hyssop essential oils and methanol extracts. Chemical composition was analyzed by gas chromatography - mass spectrometry (GC-MS) and liquid chromatography with diode array detection and mass spectrometry (LC-DAD-MS), respectively. Antioxidant activity was examined by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing/antioxidant power (FRAP) tests; genotoxic and antigenotoxic activity were examined by the comet assay, while cytotoxicity was evaluated by the 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide dye (MTT) test against tumor cell lines (SW480, MDA-MB 231, HeLa) and non-transformed human lung fibroblast cell lines (MRC-5). The essential oils were rich in monoterpene hydrocarbons (e.g., limonene; 7.99-23.81%), oxygenated monoterpenes (1,8-cineole; 38.19-67.1%) and phenylpropanoids (methyl eugenol; 0.00-28.33%). In methanol extracts, the most abundant phenolics were chlorogenic and rosmarinic acid (23.35-33.46 and 3.53-17.98 mg/g, respectively). Methanol extracts expressed moderate to weak antioxidant activity (DPPH IC50 = 56.04-199.89 µg/mL, FRAP = 0.667-0.959 mmol Fe2+/g). Hyssop preparations significantly reduced DNA damage in human whole blood cells, induced by pretreatment with hydrogen peroxide. Methanol extracts exhibited selective and potent dose- and time-dependent activity against the HeLa cell line. Results of the current study demonstrated notable H. officinalis medicinal potential, which calls for further investigation.

11.
Food Chem ; 354: 129518, 2021 Aug 30.
Article in English | MEDLINE | ID: mdl-33756324

ABSTRACT

The main objective of the present work was to develop a method for the simultaneous and comprehensive analysis of (poly-)phenolic and flavonoid compounds with liquid chromatography with diode array and mass spectrometric detection and its application to green asparagus samples. To this end, a representative set of polyphenols was used to develop the method. A through method validation was carried out with these. The method was applied to asparagus samples known as a healthy vegetable being rich in bioactive compounds. Polyphenol contents of asparagus samples were determined by carrying out quantitative and qualitative analyses by LC-DAD-ESI/MS. In this context asparagus sample extracts were obtained using solvents of different polarity. The results were evaluated statistically and showed that rutin is the major phenolic compound in asparagus. This demonstrates the versatility of this rapid and sensitive method for the simultaneous analysis of (poly-)phenolic and flavonoid compounds which was successfully applied to asparagus samples.


Subject(s)
Asparagus Plant/chemistry , Flavonoids/chemistry , Polyphenols/chemistry , Chromatography, High Pressure Liquid , Mass Spectrometry , Plant Extracts/chemistry , Rutin/chemistry
12.
Electrophoresis ; 42(1-2): 58-67, 2021 01.
Article in English | MEDLINE | ID: mdl-32628775

ABSTRACT

Pyrolysis processes are an alternative to minimize the environmental problem associated to agrifood industrial wastes. The main product resulting from these processes is a high-value liquid product, called bio-oil. Recently, the use of comprehensive two-dimensional liquid chromatography (LC × LC) has been demonstrated as a useful tool to improve the characterization of the water-soluble phases of bio-oils, considering their complexity and high water content. However, the precise composition of bio-oils from different agrifood byproducts is still unknown. In the present study, the qualitative and quantitative screening of eight aqueous phases from different biomasses, not yet reported in the literature, using LC × LC is presented. The two-dimensional approach was based on the use of two reverse phase separations. An amide column in the first dimension together with a C18 column in the second dimension were employed. Thanks to the use of diode array and mass spectrometry detection, 28 compounds were identified and quantified in the aqueous phase samples with good figures of merit. Samples showed a distinct quali-quantitative composition and a great predominance of compounds belonging to aldehydes, ketones and phenols, most of them with high polarity.


Subject(s)
Chromatography, Liquid/methods , Phenols , Plant Oils , Pyrolysis , Biofuels , Biomass , Limit of Detection , Linear Models , Phenols/analysis , Phenols/chemistry , Phenols/isolation & purification , Plant Oils/analysis , Plant Oils/chemistry , Plant Oils/isolation & purification , Reproducibility of Results
13.
Nat Prod Res ; 34(17): 2545-2553, 2020 Sep.
Article in English | MEDLINE | ID: mdl-30600731

ABSTRACT

Smilax brasiliensis is a medicinal species of the Brazilian Cerrado. The extract and fractions of this plant were analysed by LC-DAD-MS. Identified constituents included glycosylated and non-glycosylated flavonoids, especially quercetin, and phenylpropanoids, such as chlorogenic acids. The antioxidant activity was significantly more pronounced for the methanol extract and fractions than that of the commercial antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT). Maximum larvicidal activity of 85.83% was recorded in the dichloromethane fraction (LC50 = 469.78 µg mL-1). The methanol extract and fractions presented low toxicity to larvae of the shrimp brine Artemia salina, indicating selectivity for C. quinquefasciatus. These results contribute to the phytochemical study of S. brasiliensis. These compounds were identified for the first time in this species and encourage additional work on the isolation of compounds present in the extract and fractions of S. brasiliensis to evaluate the possibility of using them as natural sources of antioxidants, since cytotoxic effects were not demonstrated.


Subject(s)
Antioxidants/isolation & purification , Larva/drug effects , Phenols/pharmacology , Plant Leaves/chemistry , Smilax/chemistry , Animals , Antioxidants/pharmacology , Artemia/drug effects , Brazil , Chlorogenic Acid/analysis , Chlorogenic Acid/isolation & purification , Flavonoids/chemistry , Flavonoids/isolation & purification , Phenols/chemistry , Phenols/isolation & purification , Plant Extracts/chemistry , Quercetin/isolation & purification , Quercetin/pharmacology
14.
Nat Prod Res ; 34(4): 558-562, 2020 Feb.
Article in English | MEDLINE | ID: mdl-30388891

ABSTRACT

Methanol extract of Indigofera hirsuta, was evaluated for its antiradical potential and capacity in inhibiting lipoxygenase and aldose/aldehyde reductase enzymes. The ethyl acetate fraction derived from the methanol extract partition, showed the greatest antioxidant capacity, while the butanol was the strongest inhibitor of lipoxygenase enzyme. All fractions (diethyl ether, ethyl acetate, butanol and the aqueous residue) exhibited strong inhibition capacity of both aldose/aldehyde reductase enzymes, which comes in agreement with the ethnomedicinal plant utilization as an antidiabetic agent. LC-DAD-MS(ESI+) fraction analysis verified the findings above, leading to a conclusion regarding the biological activities attributed to the main compounds. Phytochemical analysis led to the identification of an indolic dimer, cinnamic acids, phenolics, flavonoid glycosides, a cyclic polyol, the rare sugar 1-methyl-ß-D-glucopyranoside and glycerol. Many of these compounds were isolated for the first time in Indigofera species while the indolic dimer was isolated for the first time in the Fabaceae family.


Subject(s)
Antioxidants/isolation & purification , Enzyme Inhibitors/isolation & purification , Indigofera/chemistry , Phytochemicals/analysis , Plant Extracts/chemistry , Aldehyde Reductase/antagonists & inhibitors , Antioxidants/chemistry , Antioxidants/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Flavonoids/analysis , Glycosides/analysis , Humans , Lipoxygenase Inhibitors , Phenols/analysis , Phenols/chemistry , Phytochemicals/isolation & purification , Plant Components, Aerial/chemistry
15.
Chem Biodivers ; 16(9): e1900314, 2019 Sep.
Article in English | MEDLINE | ID: mdl-31397975

ABSTRACT

In this study, we investigated the phenolic composition of the crude extract (MeOH 80 %) of Alnus cordata (Loisel.) Duby stem bark (ACE) and its antioxidant and skin whitening properties. RP-LC-DAD analysis showed a high content of hydroxycinnamic acids (47.64 %), flavanones (26.74 %) and diarylheptanoids (17.69 %). Furthermore, ACE exhibited a dose-dependent antioxidant and free-radical scavenging activity, expressed as half-maximal inhibitory concentration (IC50 ): Oxygen radical absorbance capacity (ORAC, IC50 1.78 µg mL-1 )>Trolox equivalent antioxidant capacity (TEAC, IC50 3.47 µg mL-1 )>2,2-Diphenyl-1-picrylhydrazyl (DPPH, IC50 5.83 µg mL-1 )>ß-carotene bleaching (IC50 11.58 µg mL-1 )>Ferric reducing antioxidant power (FRAP, IC50 17.28 µg mL-1 ). Moreover, ACE was able to inhibit in vitro tyrosinase activity (IC50 77.44 µg mL-1 ), l-DOPA auto-oxidation (IC50 39.58 µg mL-1 ) and in an in vivo model it exhibited bleaching effects on the pigmentation of zebrafish embryos (72 h post fertilization) without affecting their development and survival. In conclusion, results show that A. cordata stem bark may be considered a potential source of agents for the treatment of skin disorders due to its bleaching properties and favorable safety profiles, associated to a good antioxidant power.


Subject(s)
Alnus/chemistry , Antioxidants/pharmacology , Enzyme Inhibitors/pharmacology , Polyphenols/pharmacology , Skin/drug effects , Animals , Antioxidants/chemistry , Antioxidants/isolation & purification , Biphenyl Compounds/antagonists & inhibitors , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Monophenol Monooxygenase/antagonists & inhibitors , Monophenol Monooxygenase/metabolism , Picrates/antagonists & inhibitors , Plant Bark/chemistry , Plant Extracts/chemistry , Polyphenols/chemistry , Polyphenols/isolation & purification , Zebrafish
16.
Toxicol Rep ; 6: 616-624, 2019.
Article in English | MEDLINE | ID: mdl-31316897

ABSTRACT

Fruit peels of Plinia cauliflora (Mart.) Kausel are widely used in Brazilian traditional medicine, but no studies have proved the safety of its pharmacological effects on the respiratory, cardiovascular, and central nervous systems. The present study assessed the safety pharmacology of P. cauliflora in New Zealand rabbits. First, an ethanol extract (EEPC) was selected for the pharmacological experiments and chemical characterization. Then, different groups of rabbits were orally treated with EEPC (200 and 2000 mg/kg) or vehicle. Acute behavioral and physiological alterations in the modified Irwin test, respiratory rate, arterial blood gas, and various cardiovascular parameters (i.e., heart rate, blood pressure, and electrocardiography) were evaluated. The main secondary metabolites that were identified in EEPC were ellagic acid, gallic acid, O-deoxyhexosyl quercetin, and the anthocyanin O-hexosyl cyanidin. No significant behavioral or physiological changes were observed in any of the groups. None of the doses of EEPC affected respiratory rate or arterial blood gas, with no changes on blood pressure or electrocardiographic parameters. The present study showed that EEPC did not cause any significant changes in respiratory, cardiovascular, or central nervous system function. These data provide scientific evidence of the effects of this species and important safety data for its clinical use.

17.
Food Chem ; 300: 125184, 2019 Dec 01.
Article in English | MEDLINE | ID: mdl-31351261

ABSTRACT

The study evaluated bioaccumulation capacity of macro- and microelements, their impact on the production of glucosinolates and phenolic acids and antioxidant properties in a microshoot culture model of Nasturtium officinale. Elements: calcium, chromium, copper, iron, lithium, magnesium, selenium and zinc were supplemented in different salt concentrations to culture media. Bioaccumulation of elements [mg/100 gDW] varied from 1.24 (Li,1 mg/l) to 498.62 (Cr,50 mg/l) and was dependent on the type of element and its concentration. The bioconcentration factor (BCF) ranged from 11.37 (Li,25 mg/l) to 4467.00 (Ca,1 mg/l). The total glucosinolate contents [mg/100gDW] varied from 108.11 (Cr,1 mg/l) to 172.90 (Ca,1 mg/l). The presence of four phenolic acids was confirmed in the microshoots. Their total contents [mg/100gDW] ranged from 19.35 (Mg,10 mg/l) to 139.21 (Fe,50 mg/l). The highest antioxidant activity [nM trolox/mgDW], as evaluated by CUPRAC and QUENCHER-CUPRAC methods, was equal to 55.50 (Cu,1 mg/l) and 161.10 (Li,5 mg/l), respectively. The results proved good correlations between all studied parameters.


Subject(s)
Antioxidants/pharmacology , Glucosinolates/metabolism , Hydroxybenzoates/metabolism , Metals/pharmacokinetics , Nasturtium/metabolism , Antioxidants/metabolism , Nasturtium/cytology , Nasturtium/drug effects , Plant Extracts/chemistry , Plant Extracts/pharmacology , Tissue Culture Techniques
18.
Chem Biodivers ; 16(7): e1900141, 2019 Jul.
Article in English | MEDLINE | ID: mdl-31087758

ABSTRACT

Bioguided fractionation of Xylopia sericea antiplasmodial dichloromethane leaves extract led to the isolation of (-)-7-oxo-ent-kaur-16-en-19-oic acid (C20 H28 O3 ) that was identified by a combination of 1D and 2D NMR experiments (COSY, HMBC, HSQC, HSQC-TOCSY, HSQC-NOESY and NOESY) and by X-ray crystallography. A feature to be pointed out is its (4R) configuration that was inferred from the NOE experiments (HSQC-NOESY and NOESY) and X-ray crystallography. In vitro evaluation of this rare diterpene acid against the chloroquine-resistant strain Plasmodium falciparum W2 by the PfLDH method showed it disclosed a low antiplasmodial activity and was not cytotoxic to HepG2 cells (CC50 862.6±6.7 µm) by the MTT assay. The unequivocal NMR signals assignments, the X-ray crystallographic structure, the assessment to the bioactivities and the occurrence this diterpene in X. sericea are reported here for the first time.


Subject(s)
Antimalarials/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Diterpenes, Kaurane/pharmacology , Diterpenes/pharmacology , Plant Extracts/pharmacology , Plant Leaves/chemistry , Plasmodium falciparum/drug effects , Xylopia/chemistry , Antimalarials/chemistry , Antimalarials/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Crystallography, X-Ray , Diterpenes/chemistry , Diterpenes/isolation & purification , Diterpenes, Kaurane/chemistry , Diterpenes, Kaurane/isolation & purification , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Magnetic Resonance Spectroscopy , Models, Molecular , Molecular Conformation , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Structure-Activity Relationship
19.
Molecules ; 24(7)2019 Apr 10.
Article in English | MEDLINE | ID: mdl-30974893

ABSTRACT

Eurycoma longifolia is a popular folk medicine in South East Asia. This study was focused on saccharide-containing compounds including saponins, mainly because of their medical potentials. Different organic solvents such as ethyl acetate, butanol, and chloroform were used to fractionate the phytochemical groups, which were consequently precipitated in cold acetone. Solvent fractionation was found to increase the total saponin content based on colorimetric assay using vanillin and sulfuric acid. Ethyl acetate fraction and its precipitate were showed to have the highest crude saponins after acetone precipitation. The samples were shown to have anti-proliferative activity comparable with tamoxifen (IC50 = 110.6 µg/mL) against human breast cancer cells. The anti-proliferative activities of the samples were significantly improved from crude extract (IC50 = 616.3 µg/mL) to ethyl acetate fraction (IC50 = 185.4 µg/mL) and its precipitate (IC50 = 153.4 µg/mL). LC-DAD-MS/MS analysis revealed that the saccharide-containing compounds such as m/z 497, 610, 723, 836, and 949 were abundant in the samples, and they could be ionized in negative ion mode. The compounds consisted of 226 amu monomers with UV-absorbing property at 254 nm, and were tentatively identified as formylated hexoses. To conclude, solvent fractionation and acetone precipitation could produce saccharide-containing compounds including saponins with higher anti-proliferative activity than crude extract against MCF-7 cells. This is the first study to use non-toxic solvents for fractionation of bioactive compounds from highly complex plant extract of E. longifolia.


Subject(s)
Acetone/chemistry , Antineoplastic Agents, Phytogenic , Breast Neoplasms/drug therapy , Eurycoma/chemistry , Saponins , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Breast Neoplasms/metabolism , Breast Neoplasms/pathology , Cell Line, Tumor , Female , Humans , Saponins/chemistry , Saponins/isolation & purification , Saponins/pharmacology
20.
J Sci Food Agric ; 99(3): 1046-1054, 2019 Feb.
Article in English | MEDLINE | ID: mdl-30014572

ABSTRACT

BACKGROUND: Quince (Cydonia oblonga) fruits can be considered as starting material for the extraction of health-promoting phytochemicals, to be exploited in food and nutraceuticals. In the present work, liquid chromatography coupled with diode array detection and tandem mass spectrometry analysis allowed the study of the phytochemical composition of quince fruits and to compare it with those of six commercial apple varieties. RESULTS: The distribution and quantification of secondary metabolites in peel and pulp were studied and compared with six commercial apple varieties. Furthermore the in vitro antioxidant activity was determined by 2,2-diphenyl-2-picrylhydrazyl (DPPH) assay. Quince fruit presented significant amounts of shikimic and quinic acid derivatives, as well as flavonoids and procyanidins. Compared with apple, quince fruit composition was characterized by the presence of 4-caffeoylshikimic acid, 4-caffeoyl quinic acid, quercetin-3,7-diglucoside, kaempferol-3-O-rhamnoside and kaempferol-7-O-glucoside, and the dihydrochalcones were not detectable. The peel showed the highest contents of phenolics, whereas 3-O-caffeoylquinic acid was the most abundant compound in the quince pulp. The Pearson correlation index was calculated considering the quantitative amount of the phenolic constituents and the radical scavenging activity toward DPPH· both for peel and pulp extracts. CONCLUSIONS: This study highlighted the presence of significant amounts of valuable secondary metabolites in quince fruit, in particular the procyanidins and caffeoyl esters with shikimic and quinic acid. Notably, owing to the higher content in phenolic compounds and the stronger antioxidant capacity compared with the other fruits considered, the use of C. oblonga as a source of antioxidant can be valuable in nutraceuticals, revealing new possible applications of quince fruit. © 2018 Society of Chemical Industry.


Subject(s)
Antioxidants/analysis , Fruit/chemistry , Rosaceae/chemistry , Chlorogenic Acid/analysis , Chromatography, High Pressure Liquid/methods , Dietary Supplements , Functional Food , Malus/chemistry , Proanthocyanidins/analysis , Tandem Mass Spectrometry/methods
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