Determination of phenolic compounds in medicinal plants from the Lamiaceae family

A procedure for the determination of Phenolic compounds in extracts from the medicinal plants of the Lamiaceae family—garden sage (Salvia officinalis L.), creeping thyme (Thymus serpyllum L.), wild marjoram (Origanum vulgare L.), and common balm (Melissa officinalis L.)—obtained under different extraction conditions was developed. The identification of the extracted compounds was performed and their qualitative and quantitative composition was established by HPLC with diode array and mass-spectrometric detection with consideration for the obtained characteristics of the standard samples of individual components. The test samples of medicinal herbs contained caffeic acid (0.19–0.62 mg/g) and rosmaric acid (4–23 mg/g); the highest rosmaric acid content (23 mg/g) was found in wild marjoram, and the lowest content (4 mg/g), in creeping thyme. The extracts of wild marjoram contained the greatest amounts of Phenolic compounds; rosmaric acid and luteolin-7-O-β-D-glucuronide were major components, whereas protocatechuic, 3-O-caffeoylquinic, and caffeic acids were minor components.     

The composition of the plants’ extracts included in the herbal mixtures used to treat the parodontal disease

The methods of gas-liquid chromatography and mass-selective detection were used to determine the composition of the volatile fraction of plant extracts included in herb mixtures used for treating parodontal disease. The following marker substances were found: naphthalene derivatives for pot marigold, furan derivatives for trifid bur-marigold and burnet, and the specific terpenoids for licorice, milfoil, and wild marjoram. All the plants used in the herb mixture, except for pot marigold and cinquefoil, were analyzed (ion-exclusion chromatography) for the content of lower carboxylic acids. It was established that the specific acids for the wild marjoram and licorice are ascorbic and the succinic acids, respectively.     

Comparison of the oxidative stability of soybean and sunflower oils enriched with herbal plant extracts

The present study was conducted to determine and compare the oxidative stability of soybean and sunflower oils using differential scanning calorimetry (DSC). These edible oils were enriched with marjoram (Origanum majorana L.), thyme (Thymus vulgaris L.), and oregano (Origanum vulgare L.) extracts at three different concentrations and synthetic antioxidant (BHA). The fatty acid composition of studied oils was determined by gas chromatography mass spectrometry to evaluate the content of unsaturated fatty acids that are sensitive to oxidation process. Oil samples were heated in the DSC at different heating rates (4.0, 7.5, 10.0, 12.5, and 15.0 °C min^?1) and oxidation kinetic parameters (activation energy, pre-exponential factor, and oxidation rate constant) were calculated. The results showed that the oxidative stability of sunflower oil samples enriched with oregano extracts and soybean oil supplemented with thyme extracts was improved compared to samples without the addition of herbal plant extracts and the synthetic antioxidant.     

Constituents from the Fruiting Bodies of Trametes cubensis and Trametes suaveolens in Vietnam and Their Anti-Inflammatory Bioactivity

It is reported that various fungi have been used for medicine and edible foods. The tropical Trametes genus is popular and well-known in Vietnam for its health effects and bioactivities. In this study, the fruiting bodies of the edible fungi T. cubensis and T. suaveolens were collected in Vietnam. The preliminary bioactivity screening data indicated that the methanol extracts of the fruiting bodies of T. cubensis and T. suaveolens displayed significant inhibition of superoxide anion generation and elastase release in human neutrophils. Therefore, the isolation and characterization were performed on these two species by a combination of chromatographic methods and spectrometric analysis. In total, twenty-four compounds were identified, and among these (1–3) were characterized by 1D-, 2D-NMR, and HRMS analytical data. In addition, the anti-inflammatory potentials of some purified compounds were examined by the cellular model for the inhibition of superoxide anion generation and elastase release in human neutrophils. Among the isolated compounds, (5,14), and (19) displayed significant anti-inflammatory potential. As the results suggest, the extracts and isolated compounds from T. cubensis and T. suaveolens are potential candidates for the further development of new anti-inflammatory lead drugs or natural healthy foods.     

High Throughput Screening of the NatureBank ‘Marine Collection’ in a Haemonchus Bioassay Identifies Anthelmintic Activity in Extracts from a Range of Sponges from Australian Waters

Widespread resistance in parasitic nematodes to most classes of anthelmintic drugs demands the discovery and development of novel compounds with distinct mechanisms of action to complement strategic or integrated parasite control programs. Products from nature—which assume a diverse ‘chemical space’—have significant potential as a source of anthelmintic compounds. In the present study, we screened a collection of extracts (n = 7616) derived from marine invertebrates sampled from Australian waters in a high throughput bioassay for in vitro anti-parasitic activity against the barber’s pole worm (Haemonchus contortus)—an economically important parasitic nematode of livestock animals. In this high throughput screen (HTS), we identified 58 active extracts that reduced larval motility by ≥70% (at 90 h), equating to an overall ‘hit rate’ of ~0.8%. Of these 58 extracts, 16 also inhibited larval development by ≥80% (at 168 h) and/or induced ‘non-wild-type’ (abnormal) larval phenotypes with reference to ‘wild-type’ (normal) larvae not exposed to extract (negative controls). Most active extracts (54 of 58) originated from sponges, three from chordates (tunicates) and one from a coral; these extracts represented 37 distinct species/taxa of 23 families. An analysis of samples by ¹H NMR fingerprinting was utilised to dereplicate hits and to prioritise a set of 29 sponge samples for future chemical investigation. Overall, these results indicate that a range of sponge species from Australian waters represents a rich source of natural compounds with nematocidal or nematostatic properties. Our plan now is to focus on in-depth chemical investigations of the sample set prioritised herein.     

Evaluation of the antioxidant and antibacterial properties of various solvents extracts of Annona squamosa L. leaves

The present work was conducted aiming to evaluate the effect of different solvent extracts on the antioxidant and antibacterial activities of Annona squamosa L. leaves. Four solvents were chosen for the study namely; methanol 80%, acetone 50%, ethanol 50% and boiling water. Acetone and boiling water gave the highest extraction yields as compared to methanol and ethanol. Total phenolic contents of the four extracts were significantly different with acetone being the most efficient solvent and water being the least efficient one. Correlation coefficient between the total antioxidant and total phenolic content was found to be R² = 0.89 suggesting the contribution of phenolic compounds of the extract by 89% to its total antioxidant activity. The extracts were capable of scavenging H₂O₂ in a range of 43–54%. Reducing power of the extracts increased by increasing their concentration. The extracts were found to exert low to moderate antibacterial activity compared to a standard antibacterial agent. The bacterial inhibition of the extracts was found to positively correlate with their phenolic contents.     

Phytochemical and Biological Activity Studies on Nasturtium officinale (Watercress) Microshoot Cultures Grown in RITA® Temporary Immersion Systems

The main compounds in both extracts were gluconasturtiin, 4-methoxyglucobrassicin and rutoside, the amounts of which were, respectively, determined as 182.93, 58.86 and 23.24 mg/100 g dry weight (DW) in biomass extracts and 640.94, 23.47 and 7.20 mg/100 g DW in plant herb extracts. The antioxidant potential of all the studied extracts evaluated using CUPRAC (CUPric Reducing Antioxidant Activity), FRAP (Ferric Reducing Ability of Plasma), and DPPH (1,1-diphenyl-2-picrylhydrazyl) assays was comparable. The anti-inflammatory activity of the extracts was tested based on the inhibition of 15-lipoxygenase, cyclooxygenase-1, cyclooxygenase-2 (COX-2), and phospholipase A₂. The results demonstrate significantly higher inhibition of COX-2 for in vitro cultured biomass compared with the herb extracts (75.4 and 41.1%, respectively). Moreover, all the studied extracts showed almost similar antibacterial and antifungal potential. Based on these findings, and due to the fact that the growth of in vitro microshoots is independent of environmental conditions and unaffected by environmental pollution, we propose that biomass that can be rapidly grown in RITA^® bioreactors can serve as an alternative source of bioactive compounds with valuable biological properties.     

Phytochemical profiles and antioxidant capacity of the crude extracts,aqueous- and saponin-enriched butanol fractions of <Emphasis Type="Italic">Helicteres hirsuta</Emphasis> Lour. leaves and stems

This study aimed to compare phytochemical profiles and antioxidant capacity of various extracts including crude extracts, aqueous- and saponin-enriched butanol fractions prepared from the stems and leaves of Helicteres hirsuta Lour. The results revealed that all the three powdered extracts from the leaves and the stems possessed high levels of phenolics (177.07–241.03 mg GAE g^?1), flavonoids (158.03–280.06 mg CE g^?1) and saponins (165.77–1035.33 mg ESE g^?1) and exhibited strong antioxidant capacity. HPLC analysis identified nine major compounds in the leaf powder crude extract; however, the leaf aqueous fraction had three extra compounds; whereas, the saponin-enriched butanol leaf fraction had seven extra compounds. For the stems, twelve main compounds were evident in either the powdered crude extract or the aqueous fraction, and five new compounds were revealed in the saponin-enriched butanol fraction. The findings revealed that the powdered aqueous fractions and saponin-enriched butanol fractions are potential sources of biologically active compounds for further investigation and industrial utilisation.     

Chemical profile and biological activities of Peltigera horizontalis (Hudson) Baumg. thallus and apothecia extracts

Abstract

The aim of this study was to determine, for the first time, the chemical composition of Peltigera horizontalis thallus and apothecia extracts (ether, ethyl acetate, dichloromethane and acetone) by HPLC-UV and GC-MS, and evaluate activity of genotoxic, anticholinesterase, antioxidant and antibacterial potential of acetone extracts. Major constituents of thallus extracts were gyrophoric acid, and methyl gyrophorate while dominant component of apothecia extracts was tenuiorin. The predominant volatile compounds in extracts were methyl orsellinate, dodecyl acrylate, orcinol and orcinol monomethyl ether. The thallus acetone extract at concentration of 2.0 µg mL^?1 gave the greatest decrease in the micronuclei frequency (22.4%) of all tested extracts. Apothecia extract showed stronger antioxidant activity as compared to thallus extract. Tested extracts at concentration of 10?mg mL^?1 exhibited inhibitory effect (16.5% for thallus and 12.8% for apothecia) on pooled human serum cholinesterase. P. horizontalis acetone extracts had no activity against the tested five bacteria strains.     

Essential Oils of Seven Lamiaceae Plants and Their Antioxidant Capacity

Oxidative stress has been reported as a cause of many diseases like Parkinson′s, Alzheimer′s, cardiovascular disease, and diabetes. Oxidative stress can also lead to cancer formation by promoting tumor development and progression. Antioxidants derived from Lamiaceae plants play an important role in natural medicine, pharmacology, cosmetology, and aromatherapy. Herein, we examine the antioxidative capacity of essential oils from seven aromatic Lamiaceae plants against the synthetic radicals DPPH and ABTS. Among the essential oils analyzed, the most robust scavenging capacities were found in mixtures of volatile compounds from thyme and savory. The scavenging activity of tested EOs against the ABTS radical was clearly higher than activity towards DPPH. Analysis of essential oils with weaker antioxidant activity has shown that volatile compounds from marjoram, sage, and hyssop were more active than EOs from lavender and mint. It can be suggested that the potent antioxidant capacity of thyme (Thymus vulgaris) and savory (Satyreja hortensis) are related to a high level of phenolic constituents, such as thymol and carvacrol. On the other hand, the elevated antioxidative power of marjoram, sage, and hyssop essential oils may also be due to their terpinene, o-cymene, terpinolene, and terpinen-4-ol constituents. Although non-phenolic components are less active than thymol or carvacrol, they may affect antioxidant capacity synergistically.     

Effect of ionizing energy on extracts of Quillaja saponaria to be used as an antimicrobial agent on irradiated edible coating for fresh strawberries

Incorporating antimicrobial compounds into edible films or coatings provides a novel way to improve the safety and shelf life of ready-to-eat foods. Diverse studies with Quillaja saponaria Mol. (popularly named quillay) extracts have demonstrated their potential as antifungal agents against phytopathogenic fungi. Crosslinking induced by ionizing radiation is an effective method for the improvement of both barrier and mechanical properties of the edible films and coatings based on milk proteins. However there are few reports about the effects of γ-radiation on plant extracts. The aim of this work was to evaluate the effect of ionizing radiation (0, 5, 10, 15, 20, 25 and 35 kGy) on extracts prepared from in vitro plants of Q. saponaria to be used as antimicrobial agent in irradiated edible coating based on calcium caseinate and whey protein isolated, and also to establish the concentration of Q. saponaria extract to be added as an antifungal agent in the coating. Gamma irradiation since 15 kGy affects negatively the antimicrobial activity and metabolites composition of extract of Q. saponaria by reducing compounds of phenolic nature. Otherwise no effect on saponins profile was observed even at higher doses. It was possible to conclude that the antifungal activity of Q. saponaria extract is mainly related to phenolic compounds content. In addition, our work also shows that to obtain an efficient antifungal protection is necessary to add a minimum concentration of 6% of the extract after the coating irradiation.     

LC-ESI-MS/MS Polyphenolic Profile and In Vitro Study of Cosmetic Potential of Aerva lanata (L.) Juss. Herb Extracts

The aim of the present study was to investigate the phenolic composition and the biological properties of different Aerva lanata (L). Juss. herb extracts obtained with the use of accelerated solvent extraction (ASE), i.e., a green, ecological method, for cosmetic purposes. All samples exhibited high DPPH^• (9.17–119.85 mg TE/g) and ABTS^•+ (9.90–107.58 mg TE/g) scavenging activity. The extracts exhibited considerable anti-lipoxygenase (EC₅₀ between 1.14 mg/mL and 3.73 mg/mL) and anti-xanthine oxidase (EC₅₀ between 1.28 mg/mL and 3.72 mg/mL) activities, moderate chelating activity (EC₅₀ between 1.58 mg/mL and 5.30 mg/mL), and high antioxidant potential in the ORAC assay (0.36–3.84 mM TE/g). Changes in the polyphenol profile of the analysed samples depending on the solvent and temperature used for the extraction were determined with the liquid chromatography/electrospray mass spectrometry (LC-ESI-MS/MS) method. Twenty-one phenolic compounds, including flavonoids and phenolic acids, were detected and quantified. It was shown that tiliroside was one of the main phenolic metabolites in the A. lanata (L.) Juss. herb., which may suggest that this compound may be largely responsible for the observed anti-inflammatory activity of the extracts. In addition, the studied extracts exhibited promising skin-related (anti-tyrosinase, anti-elastase, anti-collagenase, and anti-hyaluronidase) activity. This study showed that Aerva lanata (L.) Juss. contains high amounts of phenolic compounds, including tiliroside, and has good skin-related activities. Therefore, the plant may be interesting as a novel source of bioactive agents for cosmetic industries.     

Ultrasound-Assisted Extraction of Anthocyanins Using Natural Deep Eutectic Solvents and Their Incorporation in Edible Films

Extracts rich in bioactive compounds added to edible films have allowed the development of active packaging that increases the shelf life of food. However, it is necessary to search for solvents that are nontoxic and not harmful to the environment, with natural deep eutectic solvents (NADES) being an attractive and easily synthesized alternative. This research aimed to design NADES by lyophilization to be used in the extraction of anthocyanins from the Chilean Luma chequen (Molina) A. Gray berry, and subsequently adding them to the matrix of edible ƙ-carrageenan films. For this purpose, ultrasound-assisted extraction (UAE) was used and the anthocyanin content was evaluated with the pH differential method. The antioxidant capacity of extracts was determined by DPPH assay and the antibacterial capacity by diffusion agar tests. The results obtained indicate that the designed NADES are efficient at extracting anthocyanins, reaching concentrations between 81.1 and 327.6 mg eq cyanidin 3-glucoside/100 g dw of L. chequen (Molina) A. Gray. The extracts reached inhibition diameters between 5 and 34 mm against Escherichia coli, Staphylococcus aureus, and Salmonella typhi strains. Once the extracts were incorporated into ƙ-carrageenan films, active edible films with antioxidant and antibacterial capacities were obtained.     

Herbicidal activity and bioactive components of Brucea javanica (L.) Merr. residue

There are many nutrients and active substances in the residue of traditional Chinese medicine, which can be processed into organic fertilizer and returned to the field to improve the soil fertility. In this study, we found that Brucea javanica (L.) Merr. residue has herbicidal activity and can be used for weed control in the field, this prompted us to investigate the active constituents in it. The herbicidal activities of extracts of B. javanica residue were evaluated by conducting bioassays against gramineous weed, Eleusine indica (L.) Gaertn. and broad-leaved weed, Bidens pilosa L., respectively. It confirmed that ethyl acetate and n-butanol extracts possessed potent biological activities on seed germination and seedling growth of E. indica at 5 mg/mL. This prompted us to investigate the active constituents in the seeds residue. By the activity-guided fractionation, eight known compounds were isolated, which were bruceines D?F (1–3), pityriacitrin (4), 4-(9H-β-carbolin-1-yl)-4-oxobut-2-enoic acid methyl ester (5), protocatechuic acid (6), vanillic acid (7) and carisphthalate (8). Then, three quassinoids (1–3) were evaluated for their potential herbicidal effects in bioassay. Results showed that bruceines D?F have potential herbicidal activity against the test weeds. In the range of experimental concentration, bruceine D had obvious herbicidal effect on the two tested weeds. At the concentration of 31.25 μg/mL, bruceine D could completely inhibit the root growth of E. indica; at the concentration of 125 μg/mL, bruceine D can inhibit the seed germination and shoot elongation of E. indica and the shoot growth of B. pilosa, with the inhibition reached 100%. In addition, at the same concentration (250 μg/mL), bruceines D?F could completely affected shoot elongation of B. pilosa. These results showed that B. javanica residue is a potential source of botanical herbicide development, which has great agricultural economic value, at the same time, the reuse of B. javanica residue realizes the transformation of waste into treasure, rational utilization of resources and sustainable development.     

Effect of seasonal variation on the chemical composition and antioxidant and antifungal activities of Convolvulus althaeoides L. leaf extracts

The composition of polyphenols, chlorophylls and carotenoids of eight extracts of Convolvulus althaeoides L. leaves, harvested in two different seasons, winter and spring, and extracted by hot extraction method using four solvents (dichloromethane, chloroform, ethyl acetate and ethanol) with increasing polarity, were evaluated along with their antioxidant and antifungal activities. Qualitative and quantitative variations were observed in the composition based on two different high performance liquid chromatography systems, liquid chromatography-photodiode array detection coupled to either atmospheric pressure chemical ionization mass spectrometry or to electrospray ionization mass spectrometry, permitting the identification of 22 polyphenols, 11 chlorophyll derivatives and 10 carotenoid compounds. Polyphenolic compounds were predominant in extracts from leaves collected in winter, whereas pigments were predominant in the spring collections. Antioxidant activities of the extracts were determined by DPPH radical scavenging method, revealing a half inhibition concentration (IC₅₀) ranging from 0.1369 ± 0.0272 mg g⁻¹ to 0.432 ± 0.0018 mg g⁻¹, with no correlation to seasonal fluctuation. Concerning antifungal assays, ethyl acetate and ethanol extracts have been shown to be the most active against dermatophytes (T. rubrum, T. menthagrophytes, M. canis), with inhibiting percentages reaching 100% with 50 mg mL⁻¹. Moreover, ethyl acetate and ethanol extracts showed a maximum inhibition potential with minimum inhibitory/fungicidal concentrations ranging from 0.78 to 6.25 mg mL⁻¹ on Candida spp. cultures. The winter collect of these extracts showed an inhibitory effect of 90% on Candida albicans germ tubes formation, at a concentration of 3.1 mg mL⁻¹. In conclusion, seasonality seems to influence the quality and the quantity of natural substances from leaves of C. althaeoides L., which have major importance on the antioxidant and the antifungal effectiveness.     

Bioassay‐guided Isolation and Antioxidant Activity of Sulfur‐containing Compounds from Clinacanthus nutans

Clinacanthus nutans has been used in traditional herbal medicine for cancer prevention, but the specific bioactive compounds responsible for the observed activities have not been explored. Different polar solvents such as methanol, chloroform, ethyl acetate, and hexane were used for the extraction. The extracts, fractions, and isolated compounds were subjected to DPPH and ferric reducing antioxidant potential (FRAP) assays. Methanol extracts show significant free‐radical scavenging activity of 69.09% in DPPH and 56.49% FRAP. Purification of MeOH extracts afforded the fraction FB28 and two new sulfur‐containing compounds, named clinamide D and E ( 1 , 2 ). Compound ( 1 ) proved to be more active with an IC₅₀ value for DPPH radical scavenging of 118.27 ± 0.01 µg/mL and reduction of Fe³⁺–TPTZ complex of 386.24 ± 0.02, higher than that of the standard ascorbic acid. Sulfur‐containing compounds isolated from C. nutans is a potential natural antioxidant.     

Chemical Profile,Cytotoxic Activity and Oxidative Stress Reduction of Different Syringa vulgaris L. Extracts

Syringa vulgaris L. (common lilac) is one of the most popular ornamental species, but also a promising not comprehensively studied source of bioactive compounds with important therapeutic potential. Our study was designed to characterize the chemical composition and to assess the antioxidant and cytotoxic properties of ethanolic extracts obtained from S. vulgaris L. flowers, leaves, bark, and fruit. The chemical profile of the ethanolic extracts was investigated using chromatographic (HPLC-DAD-ESI⁺, GC-MS) and spectral (UV-Vis, FT-IR) methods, while the protective effect against free radicals was evaluated in vitro by different chemical assays (DPPH, FRAP, CUPRAC). The cytotoxic activity was tested on two tumoral cell lines, HeLa, B16F10, using the MTT assay. Significant amounts of free or glycosylated chemical components belonging to various therapeutically important structural classes, such as phenyl-propanoids (syringin, acteoside, echinacoside), flavonoids (quercetin, kaempferol derivatives) and secoiridoids (secologanoside, oleuropein, 10-hydroxy oleuropein, demethyloleuropein, syringalactone A, nuzhenide, lingstroside) were obtained for the flowers, leaves and bark extracts, respectively. Furthermore, MTT tests pointed out a significant cytotoxic potential expressed in a non-dose-dependent manner toward the tumoral lines. The performed methods underlined that S. vulgaris extracts, in particular belonging to flowers and leaves, represent valuable sources of compounds with antioxidant and antitumoral potential.     

Using the UPLC–ESI–Q‐TOF–MSE method and intestinal bacteria for metabolite identification in the nonpolysaccharide fraction from Bletilla striata

Bletilla striata (Thunb.) Reichb. f. (Orchidaceae), also known as Bai‐ji, is a traditional Chinese herb that is widely used in Asia to treat hematemesis, hemoptysis, traumatic bleeding and other similar disorders. Most studies have focused on the pharmacological activities of polysaccharide extracts from B. striata. Our previous studies found that the nonpolysaccharide fraction from B. striata extract also has a hemostatic effect; however, the active constituents responsible for this pharmacological action are unclear. Thus, the metabolic profiles of the nonpolysaccharide fraction were investigated in Sprague–Dawley rats and intestinal bacteria models using ultra‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry. Mass data were acquired by the MS^E method. Eight components including five prototypes and three metabolites were identified in rat biofluids after oral administration of the nonpolysaccharide fraction. The parent compounds underwent various metabolic processes, including hydrolysis, deglucosylation, glycosylation and sulfate conjugation. The results not only reveal the possible metabolic pathway, but also indicate the potential pharmacological components. Further mechanistic studies using nonpolysaccharide compounds of the B. striata extract are required to obtain potential candidate compounds.     

Simultaneous characterization and quantification of flavonoids in Euonymus alatus (Thunb.) Siebold from different origins by HPLC-PAD–MS

A high-performance liquid chromatography coupled with photodiode array detection and electrospray ionization tandem mass spectrometry (HPLC-PAD–ESI-MS) method has been developed for the simultaneous identification and quantification of active compounds (rutin and quercetin) contained in Traditional Chinese Medicine (TCM) Euonymus alatus (Thunb.) Siebold (EAS). The herb samples from ten main origins and five medicinal portions (leaf, fruit, stem, pterygium and root) were investigated. The separation was performed on a Shim C₁₈ column at 30 °C with an isocratic elution. Methanol (A) and water (0.5% methanoic acid, v/v) (B) were used as mobile phases. The recoveries of the two compounds were 100.184% and 100.417%, respectively, and all of them showed good linearity (r² ? 0.9993) in relatively wide concentration ranges. The developed method was applied to identify and quantify the two major active compounds in the collected herb samples, and the results indicated that contents of the two compounds in EAS varied significantly from habitat to habitat. It was demonstrated that the proposed method was helpful for the quality evaluation of EAS.