Bioactivity and chemical characterization in hydrophilic and lipophilic compounds of Chenopodium ambrosioides L.

The bioactive properties (antioxidant and antitumour activities, and hepatotoxicity) of the infusion and methanolic extracts of Chenopodium ambrosioides L., a plant commonly used in Portuguese folk medicine, were compared. The chemical composition in hydrophilic (sugars, organic acids and phenolic compounds) and lipophilic (fatty acids and tocopherols) fractions were determined. In general, the infusion revealed higher antioxidant activity, while the methanolic extract was the only one showing antitumour effects against colon, cervical and hepatocellular carcinoma cell lines. No toxicity in non-tumour cells was observed either for the infusion or the extract. The studied plant proved to be a good source of natural antioxidants and other bioactive compounds, which may have industrial use. As far as we know, this is the first detailed chemical characterization and bioactivity evaluation of C. ambrosioides methanolic extract and infusion.     

Nutrients,phytochemicals and bioactivity of wild Roman chamomile: A comparison between the herb and its preparations

Roman chamomile, Chamaemelum nobile L. (Asteraceae), has been used for medicinal applications, mainly through oral dosage forms (decoctions and infusions). Herein, the nutritional characterisation of C. nobile was performed, and herbal material and its decoction and infusion were submitted to an analysis of phytochemicals and bioactivity evaluation. The antioxidant activity was determined by free radicals scavenging activity, reducing power and inhibition of lipid peroxidation, the antitumour potential was tested in human tumour cell lines (breast, lung, colon, cervical and hepatocellular carcinomas), and the hepatotoxicity was evaluated using a porcine liver primary cell culture. C. nobile proved to be an equilibrated valuable herb rich in carbohydrates and proteins, and poor in fat, providing tocopherols, carotenoids and essential fatty acids (C18:2n6 and C18:3n3). Moreover, the herb and its infusion are a source of phenolic compounds (flavonoids such as flavonols and flavones, phenolic acids and derivatives) and organic acids (oxalic, quinic, malic, citric and fumaric acids) that showed antioxidant and antitumour activities, without hepatotoxicity. The most abundant compounds in the plant extract and infusion were 5-O-caffeoylquinic acid and an apigenin derivative. These, as well as other bioactive compounds, are affected in C. nobile decoction, leading to a lower antioxidant potential and absence of antitumour potential. The plant bioactivity could be explored in the medicine, food, and cosmetic industries.     

Antioxidant activity, ascorbic acid, phenolic compounds and sugars of wild and commercial Tuberaria lignosa samples: Effects of drying and oral preparation methods

The antioxidant activity and phytochemical composition (ascorbic acid, free sugars and phenolic compounds) of decoctions and infusions of wild and commercial samples of Tuberaria lignosa (Sweet) Samp. Aerial parts were evaluated and compared. Among wild samples, the effects of the drying method (freeze or shade-drying) on those parameters were studied. Infusion of the freeze-dried wild sample gave the highest levels of sugars, while infusion of shade-dried wild sample and decoction of the freeze-dried sample presented higher ascorbic acid and phenolic compounds content (including ellagitannins and flavonoids) than the other samples. The last two samples also revealed higher antioxidant activity, in some cases even higher than Trolox. Decoctions gave lower amounts of disaccharides than infusions, which seemed to be hydrolysed, increasing the content of monosaccharides. Commercial samples showed the lowest content in phenolic compounds, mainly in ellagitannins and flavonoids, and also the lowest antioxidant activity. This work gives scientific evidence to the traditional medicinal uses of wild Tuberaria lignosa, highlighting the interest of its decoctions and infusions as a source of bioactive compounds and functional beverages.     

Infusion and decoction of wild German chamomile: Bioactivity and characterization of organic acids and phenolic compounds

Natural products represent a rich source of biologically active compounds and are an example of molecular diversity, with recognised potential in drug discovery. Herein, the methanol extract of Matricaria recutita L. (German chamomile) and its decoction and infusion (the most consumed preparations of this herb) were submitted to an analysis of phytochemicals and bioactivity evaluation. The antioxidant activity was determined by free radicals scavenging activity, reducing power and inhibition of lipid peroxidation; the antitumour potential was tested in human tumour cell lines (breast, lung, colon, cervical and hepatocellular carcinomas), and the hepatotoxicity was evaluated using a porcine liver primary cell culture (non-tumour cells). All the samples revealed antioxidant properties. The decoction exhibited no antitumour activity (GI₅₀ > 400 μg/mL) which could indicate that this bioactivity might be related to compounds (including phenolic compounds) that were not extracted or that were affected by the decoction procedure. Both plant methanol extract and infusion showed inhibitory activity to the growth of HCT-15 (GI₅₀ 250.24 and 298.23 μg/mL, respectively) and HeLa (GI₅₀ 259.36 and 277.67 μg/mL, respectively) cell lines, without hepatotoxicity (GI₅₀ > 400 μg/mL). Infusion and decoction gave higher contents of organic acids (24.42 and 23.35 g/100 g dw). Otherwise, the plant methanol extract contained the highest amounts of both phenolic acids (3.99 g/100 g dw) and flavonoids (2.59 g/100 g dw). The major compound found in all the preparations was luteolin O-acylhexoside. Overall, German chamomile contains important phytochemicals with bioactive properties (mainly antitumour potential selective to colon and cervical carcinoma cell lines) to be explored in the pharmaceutical, food and cosmetics industries.     

Analytical Methods Applied to the Chemical Characterization and Antioxidant Properties of Three Wild Edible Mushroom Species from Northeastern Portugal

The chemical composition and the antioxidant potential of three species of wild mushrooms from Northeastern Portugal, namely Agaricus albertii, Agaricus urinascens var. excellens, and Pleurotus eryngii, were compared. Standard procedures were followed in the nutritional value evaluation, while chromatographic procedures were used to analyze free sugars, fatty acids, tocopherols, phenolic compounds, and organic acids. To assess the antioxidant potential, reducing power, radical-scavenging activity, and lipid peroxidation inhibition were evaluated. P. eryngii revealed the highest levels of macronutrients, except proteins, as also the highest sugars, tocopherols, and monounsaturated fatty acids contents. A. albertii and A. urinascens var. excellens showed similar macronutrients composition. However, A. albertii revealed the highest content in PUFA and phenolic compounds. P. eryngii revealed the highest reducing power and radical-scavenging activity and A. albertii the highest lipid peroxidation inhibition. This study provides a detailed chemical characterization and antioxidant potential evaluation of three species of wild mushrooms from Portugal not yet previously reported. Thus, this work intended to contribute to the increase of information concerning species of edible mushrooms (directed to the scientific community and general population) as well as contribute to the conservation of these resources as sources of compounds of interest.     

Targeted metabolites analysis in wild Boletus species

In European countries, the edible mushrooms from the Boletus genus are the most frequently harvested of all the forest species gathered in the wild. Their popularity is mainly due to their sensory qualities, in particular aroma, taste and texture. In the present work, a targeted metabolites analysis was performed in six wild Boletus species. The analysis of primary metabolites revealed proteins, carbohydrates, fatty acids, mainly linoleic acid, sugars, mainly mannitol and trehalose, and vitamins (tocopherols and ascorbic acid). Secondary metabolites, such as phenolic acids, were also identified and quantified, and correlated to Boletus antioxidant properties including free radical scavenging activity, reducing power and lipid peroxidation inhibition. As a source of these important metabolites, the edible Boletus spp. could be directly used in the human diet as health foods, taking advantage on the synergistic and/or additive effects of all the antioxidants present, while inedible species could represent a source of extractable phenolic compounds to be used as additives in the food industry or as components in pharmaceutical and cosmetic formulations.     

Organic acids,antioxidant capacity,phenolic content and lipid characterisation of Georgia-grown underutilized fruit crops

Four underutilized Georgia-grown fruit crops, namely loquat (Eriobotrya japonica), mayhaw (Crataegus sp.), fig (Ficus carica), and pawpaw (Asimina triloba), and their leaves were analysed for total polyphenols by Folin–Ciocalteau method, and antioxidant capacity by ferric-reducing antioxidant power (FRAP) and Trolox-equivalent antioxidant capacity (TEAC) assays. Organic acids and phenolic compounds were identified by RP-HPLC. For lipid profile, fruits were separated into two fractions – seed and fruit (i.e., without seed); lipid was extracted using the Folch method and analysed for fatty acids, phytosterols, tocopherols, and phospholipids. The major organic acid identified in all samples was malic acid (177–1918 mg/100 g FW). The predominant phenolic acids in all the fruits were gallic (1.5–6.4 mg/100 g FW) and ellagic (0.2–33.8 mg/100 g FW), and the most abundant flavonoid was catechin (12.2–37.8 mg/100 g FW). Total lipid content varied from 0.1% in mayhaw fruit to 21.5% in pawpaw seed. Linoleic acid was the predominant fatty acid in all of the samples (28.2–55.7%).     

Effects induced by the nodulation with Bradyrhizobium japonicum on Glycine max (soybean) metabolism and antioxidant potential

This study was conducted in order to assess the effect of the inoculation of Glycine max (soybean) with Bradyrhizobium japonicum on the metabolite profile and antioxidant potential of its aerial parts. Extracts containing phenolic compounds and organic acids were analysed by HPLC–DAD and HPLC–UV, respectively. Volatiles profile was determined by HS-SPME/GC–IT-MS. The antioxidant activity of acidic and methanolic extracts was assessed against DPPH. Nodulation caused by B. japonicum led to an increase in the contents of phenolic compounds and organic acids. The same was observed for volatile compounds, with compounds like linalyl acetate, menthyl acetate and α-farnesene being detected only in inoculated plants. The phenolic extracts showed stronger antioxidant capacity than the organic acid extracts. In addition, extracts from plants nodulated with B. japonicum exhibited significantly higher antioxidant activity than control samples. These findings suggest that the inoculation with nodulating B. japonicum strains may be employed to manipulate the content of interesting metabolites in G. max aerial parts.     

Wild Prunus Fruit Species as a Rich Source of Bioactive Compounds

Sugars, organic acids, carotenoids, tocopherols, chlorophylls, and phenolic compounds were quantified in fruit of 4 wild growing Prunus species (wild cherry, bird cherry, blackthorn, and mahaleb cherry) using HPLC‐DAD‐MSn. In wild Prunus, the major sugars were glucose and fructose, whereas malic and citric acids dominated among organic acids. The most abundant classes of phenolic compounds in the analyzed fruit species were anthocyanins, flavonols, derivatives of cinnamic acids, and flavanols. Two major groups of anthocyanins measured in Prunus fruits were cyanidin‐3‐rutinoside and cyanidin‐3‐glucoside. Flavonols were represented by 19 derivatives of quercetin, 10 derivatives of kaempferol, and 2 derivatives of isorhamnetin. The highest total flavonol content was measured in mahaleb cherry and bird cherry, followed by blackthorn and wild cherry fruit. Total phenolic content varied from 2373 (wild cherry) to 11053 mg GAE per kg (bird cherry) and ferric reducing antioxidant power antioxidant activity from 7.26 to 31.54 mM trolox equivalents per kg fruits.     

Methylxanthines,phenolic composition,and antioxidant activity of bark from residues from mate tree harvesting (Ilex paraguariensis A. St. Hil.)

Leaves and products made from them are the major focus of research on bioactive compounds of mate (Ilex paraguariensis). However, studies on other parts of the plant, are scarce. The aim of this study was to determine the methylxanthines, phenolic compounds, and antioxidant activity of mate bark (residual biomass) and compare with those of mate leaves. The high antioxidant activity of mate bark and its high concentration of total polyphenols were apparent in both the aqueous and the methanolic extracts, the values of which were greater than those detected in the leaves. Of the phenolic acids identified, the levels of chlorogenic acid and 4,5-dicaffeoylquinic acid in the samples were significantly higher in the methanolic bark extract. With regard to methylxanthines, considerable concentrations were detected in the samples. The results obtained contribute to the viability of exploiting this residue, broadening the use of the mate plant.     

Effect of nitrogen starvation on the phenolic metabolism and antioxidant properties of yarrow (Achillea collina Becker ex Rchb.)

In this study, the effects of long-term nitrogen deficiency (N 0.1 mM for 4 months) on growth, phenolic content and activity of phenylalanine ammonia lyase (PAL; EC 4.3.1.5) were investigated in the leaves, inflorescences and roots of yarrow (Achillea collina Becker ex Rchb.) grown in hydroponics. The antioxidant capacity of methanol extracts was also evaluated. Nitrogen starvation decreased plant growth and the leaves’ total nitrogen, amino acids, proteins, chlorophylls and carotenoids contents indicating that the primary metabolism was severely limited by low nitrogen availability. The amount of total phenolics and the antioxidant capacity were higher in leaves and roots of nitrogen-starved compared to control plants. The most abundant phenolic acids identified in yarrow were 5-O-caffeoylquinic acid (chlorogenic acid), and 3,5 and 4,5-di-O-caffeoylquinic acids. Nitrogen starvation significantly increased the contents of all these compounds and the PAL activity in leaf and root tissues. Results suggest that hydroponics, with proper manipulation of nutritional factors, might be a suitable system for the production of compounds with health benefits, such as caffeic acid derivatives, in yarrow.     

Toward the antioxidant and chemical characterization of mycorrhizal mushrooms from northeast Portugal

Abstract: Mushrooms are widely appreciated all over the world for their nutritional properties and pharmacological value as sources of important bioactive compounds. Mycorrhizal macrofungi associate with plant roots constituting a symbiotic relationship. This symbiosis could influence the production of secondary metabolites, including bioactive compounds. We focused on the evaluation of antioxidant potential and chemical composition of mycorrhizal mushrooms species from Northeast Portugal: Amanita caesarea, Amanita muscaria, Amanita pantherina, Chroogomphus fulmineus, Cortinarius anomalus, Cortinarius collinitus, Cortinarius violaceus, Lactarius quietus, Lactarius volemus, Russula sardonia, Suillus luteus, and Tricholoma ustale. A similar profile of metabolites was observed in the studied species with the order sugars > fat > ascorbic acid > phenolic compounds > tocopherols. Nevertheless, the samples revealed different compositions: prevalence of sugars in L. volemus, fat and ascorbic acid in A. muscaria, phenolic compounds in C. anomalus and tocopherols, and antioxidant activity in S. luteus. Practical Application: Chemical characterization of 12 mycorrhizal mushrooms was achieved. They are sources of nutraceuticals, such as sugars and fatty acids, and contain bioactive compounds, such as vitamins and phenolic acids. Edible species can be incorporated in diets as sources of antioxidants, while nonedible species can be explored as sources of bioactive metabolites.     

Determination of free phenolic acids and antioxidant activity of methanolic extracts obtained from fruits and leaves of Chenopodium album

In this study, determination of phenolic acids as well as investigation of antioxidant activity of methanolic extracts from the fruits and leaves of Chenopodium album is described. Extracts were subjected to acidic hydrolysis in order to obtain total free phenolic acids. However, some of phenolic acids were identified and quantified by HPLC-DAD. The results were confirmed by LC-MS equipped with MS-ESI. In addition, Folin–Ciocalteu method was applied to determine the total phenolic contents. The antioxidant activity of C. album extracts was examined by using DPPH and hydroxyl radical-scavenging activity assays. Results revealed that the leaves extract exhibits better performance in antioxidant assays and in the higher total phenolic contents (3066 mg of GAE/100 g) when compared to fruits extract (1385 mg of GAE/100 g). From these results it has been revealed that the methanolic extracts of C. album from fruits and leaves have great potential as a source for natural health products.     

Phytochemicals and bioactive properties of Ilex paraguariensis: An in-vitro comparative study between the whole plant,leaves and stems

The leaves, stems and whole plant of Ilex paraguariensis (yerba mate) were characterized in terms of their chemical composition and biological activities in order to determine which part of the plant is more interesting to develop bioactive formulations. The yerba mate samples contain at least five free sugars, five organic acids, eighteen fatty acids, one tocopherol, nine hydroxycinnamoyl derivatives and two flavonols. The leaf extract revealed the highest antioxidant activity, correlating with its highest levels of phenolic compounds. By contrast, the stem extract showed the highest anti-inflammatory potential and was also the most potent against MCF-7 and HepG2 cell lines, probably due to the presence of other phytochemicals. The absence of hepatotoxicity in the extracts was confirmed in porcine liver primary cells. Although the yerba mate extracts have been widely studied, this report shows for the first time the distinct potentialities of each individual part of the plant.     

Determination of antioxidant compounds and antioxidant activity in commercial oilseeds for food use

Different commercial edible oilseed samples were analyzed in order to evaluate the compounds involved in antioxidant activity. Fatty acids, triacylglycerols, tocopherols, chlorophylls, β-carotene, squalene, phenolic compounds and CIE L^∗a^∗b^∗ coordinates were assayed. Strong chemical variability depending on the oilseed variety was observed. Antioxidant activity was evaluated for the oils, both for their methanol-soluble phase and the fraction insoluble in methanol. DPPH radical scavenging activity expressed in TEAC ranged between 0.45 and 2.30 mmol/l in peanut and maize oils, respectively. Free radical scavenging activity was mainly influenced by tocopherols content (r = +0.70) in oils and polyunsaturated fatty acids (r = +0.61) in the fraction nonsoluble in methanol. Variability of the correlation between the antioxidant activity and the composition of the oilseeds could be attributed to the differences in the squalene, chlorophylls, carotenoids, and phenols contents of the oils and their mutual interactions.     

Exotic fruits as a source of important phytochemicals: Improving the traditional use of Rosa canina fruits in Portugal

Several exotic fruits are used in folk medicine as potential sources of healthy compounds. Rosa canina L. (dog rose) fruits and other parts used to be widely consumed in rural areas from Portugal. The present work intends to highlight the presence of bioactive compounds in those different parts, in order to improve their use based on scientific studies. The antioxidant activity was screened through: radical scavenging effects, reducing power, and inhibition of lipid peroxidation in brain homogenates. Phytochemical characterization included determination of sugars by HPLC-RI, fatty acids by GC-FID, tocopherols by HPLC-fluorescence, phenolics, flavonoids, carotenoids, chlorophylls and ascorbic acid, by spectrophotometric techniques. Galls revealed the highest antioxidant potential, ripen hips showed the highest tocopherols and ??-carotene contents, as also the most adequate n-6/n-3 fatty acids ratios. Unripe hips gave the highest levels of ascorbic acid and petals revealed the highest concentration of sugars. Ethnobotanical studies conducted have mentioned different use-reports for seeds, petals, flowers and galls, as well as for fruits in different stages of maturity and, therefore, the comparison between chemical compounds and antioxidant properties of those different parts is a key-point of the present study. Furthermore, the levels of antioxidants found would make them suitable sources of compounds to be used commercially to retard rancidity in fatty materials in food manufacturing, to reduce the effects of ageing and to help to prevent oxidative-stress related diseases such as cancer and heart disease.     

Cytotoxicity of Coprinopsis atramentaria extract,organic acids and their synthesized methylated and glucuronate derivatives

Coprinopsis atramentaria is a wild edible mushroom whose methanolic extract revealed a marked antioxidant activity; p-hydroxybenzoic (HA), p-coumaric (CoA) and cinnamic (CA) acids were identified in the extract. In the present work, the cytotoxicity of C. atramentaria extract, previously identified organic acids and their synthesized derivatives (methylated compounds and protected glucuronides) was evaluated. Among all the tested cell lines (MCF-7—breast adenocarcinoma, NCI-H460—non-small cell lung carcinoma, HCT15—colon carcinoma, HeLa—cervical carcinoma and HepG2—hepatocellular carcinoma), the extract presented good activity for the first three cell lines mentioned; in most of the cases methylated and glucuronide derivatives showed a higher activity than the corresponding parental compounds. The substitution of the carboxylic group (in parental organic acids) for an ester (in methylated derivatives) increased the cytotoxicity for tumor cell lines. Acetylated glucuronide derivatives showed higher cytotoxicity when compared with the corresponding parental acids.     

Analytical Tools Used to Distinguish Chemical Profiles of Plants Widely Consumed as Infusions and Dietary Supplements: Artichoke,Milk Thistle,and Borututu

Artichoke, borututu, and milk thistle are three medicinal plants widely consumed as infusions or included in dietary supplements (e.g., pills and syrups). Despite the high consumption of these plants, studies on their nutritional value and primary metabolites are scarce, with their composition in secondary metabolites such as phenolic compounds being only reported. Therefore, their nutritional value was assessed, and analytical tools (liquid and gas chromatography coupled to different detectors) were used to distinguish their chemical profiles according to their hydrophilic (sugars and organic acids) and lipophilic (fatty acids and tocopherols) components. Chromatographic techniques are important analytical tools used in the identification and quantification of several molecules, also being a standard requirement to distinguish different profiles. Borututu gave the highest energetic value with the highest content of carbohydrates and fat, sucrose and total sugars, shikimic and citric acids, and α-, β-, δ-, and total tocopherols. Artichoke had the highest ash and protein contents, oxalic acid, SFA (mainly palmitic acid), and γ-tocopherol, and also the best n-6/n-3 ratio. Milk thistle showed the highest levels of fructose and glucose, quinic acid and total organic acids, and PUFA, mainly linoleic acid, and the best PUFA/SFA ratio. The hydrophilic compounds identified in the studied plants, mostly sugars, are responsible for the energy contribution of their widely consumed infusions. Otherwise, the bioactivity of lipophilic compounds, namely, unsaturated fatty acids and tocopherols, is lost in those preparations but can be recovered in dietary supplements based on the plants. As far as we know, this is the first report on the detailed composition of the three plants regarding their nutritional features.     

Phenolic acids and flavonoids in leaf and floral stem of cultivated and wild Cynara cardunculus L. genotypes

Ten genotypes, cultivated and wild of Cynara cardunculus L. were evaluated for their content of phenolic acids, flavonoids and their antioxidant activity. The major compounds present in the leaf were luteolin derivatives in globe artichoke and apigenin derivatives in wild and cultivated cardoon. Apart from ‘Cimiciusa di Mazzarino’ (var. scolymus), caffeoylquinic acids represent the main phenolic compounds in the floral stem. In particular, ‘Sylvestris Creta’ (var. sylvestris) and ‘Violetto di Sicilia’ (var. scolymus) show the highest content of caffeoylquinic acid ∼95% of the total measured polyphenols. The antioxidant capacity, in both leaf and floral stem, was qualitatively and quantitatively dependent on the phenolic acid and flavonoid profile. The phenolic acids and flavonoids in normally uneaten parts of wild and cultivated artichoke could be exploited as sources of natural antioxidants.     

Investigations of anti-inflammatory,antinociceptive, antioxidant and aldose reductase inhibitory activities of phenolic compounds from Sideritis brevibracteata

The Sideritis species are widely used in the treatment of gastrointestinal disorders, rheumatism, cough, the common cold and as a diuretic, and they are commonly used as an herbal tea in folk medicine in Turkey. The teas of Sideritis have unique tastes, pleasant aromas and a transparent yellow colour, and are preferred as a hot beverage. In order to evaluate this information, the crude methanolic extract and the water soluble part of the methanolic extract after partition with chloroform and n-butanol were investigated for their anti-inflammatory and antinociceptive activities. Phytochemical studies performed on the n-butanol extract of the overground parts of Sideritis brevibracteata, which is rich in phenolic compounds with promising activities, resulted in the isolation of six acetylated allose containing 8-hydroxyflavone glycosides and a phenylethanoid glycoside. The structures of the compounds were established by spectroscopic evidence (UV, IR, NMR, MS). Furthermore, these phenolic compounds of S. brevibracteata were studied for anti-inflammatory, antinociceptive, antioxidant and aldose reductase inhibitory activities. The experimental data demonstrated that S. brevibracteata displayed remarkable anti-inflammatory, antinociceptive and antioxidant activities.