Search

Tecoma stans (L.) Kunth (Bignoniaceae), is popularly known as ipe-mirim, and used in traditional medicine for the treatment of diabetes and digestive problems. The aim of this work was to evaluate the antibacterial, antioxidant and synergistic potential of the ethanol extract and fractions from the T. stans flowers, and to determine their chemical composition. The hexane fraction (HEX) was analyzed by Gas Chromatography-Mass Spectrometry (GC-MS), and fatty acid esters and the phytosterols could be identified. The ethanol extract (EE), and dichloromethane (DCM), ethyl acetate (EA) and hydroethanol (HE) fractions were analyzed by liquid chromatography coupled to a diode array detector and mass spectrometer (LC-DAD-MS). Alkaloids (tecomine, tecostamine, and coumaroyl-spermidine analogs), O-glycosylated flavones and flavonols (O-glucuronyl O-methyl quercetin, O-hexosyl luteolin, and others), and phenylethanoid glycosides (dihydroxyphenyl ethyl O-caffeoyl O-deoxyhexosyl hexoside, hydroxyphenyl ethyl O-coumaroyl O-deoxyhexosyl hexoside, and others) were identified. The EE with DCM and EA fractions exhibited antioxidant effects, and had the highest levels of phenolic compounds. Regarding Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) tests, the EE, DCM and EA fractions showed potential results against Escherichia coli, E. coli EHEC and Enterococcus faecalis. The EE and DCM and EA fractions interacted synergistically with amoxicillin and tetracycline decreasing the MIC of antibiotics 2–5 fold when compared with the MIC of antibiotics used alone. These results provide a basis for additional studies aimed to evaluate the possibility of using extract or fractions from T. stans as natural sources of antioxidants and antibacterial agents of plant origin.

Background: The plants of high phenolic contents are perfect antioxidant and anti-inflammatory agents and participate in biological studies as effective agents towards different cancer cell lines. Objective: To investigate the antioxidant, anti-inflammatory, and cytotoxic activities of the hydromethanolic leaf extract of Jasminum multiflorum (Burm. f.) Andrews. (J. multiflorum), and phenolic profiling of the extract. Methods: The antioxidant activity for the extract was estimated using β-Carotene-linoleic and Ferric Reducing Antioxidant Power (FRAP) assays. The anti-inflammatory activity was evaluated by histamine release assay. Cytotoxicity of J. multiflorum was performed using a neutral red uptake assay towards breast cancer (MCF-7) and colorectal cancer (HCT 116) cell lines. Phenolic profiling of the leaves was characterized using high performance liquid chromatography coupled to photodiode array detector-mass spectroscopy-mass spectroscopy (HPLC-PDA-MS/MS), and chromatographic isolation and identification of the isolated compounds were performed using spectroscopic and NMR data, and virtual docking was performed to the isolated compounds against HSP90 (HEAT SHOCK PROTEIN 90). Results : At a concentration of 75 μg mL-1, J. multiflorum extract showed high antioxidant power; 68.23±0.35 % inhibition and 60.30±0.60 a TEAC (μmol Trolox g-1) for β-Carotene-linoleic assay and FRAP assay; respectively, and possessed anti-inflammatory activity with IC50 67.2 μg/ml. J. multiflorum showed high cytotoxic activity with IC50 of 24.81 μg/ml and 11.38 μg/ml for MCF-7 and HCT 116 cell lines, respectively. HPLC-PDA-MS/MS analysis tentatively identified 39 compounds; major compounds are secoiridoid glycosides, kaempferol, and quercetin glycosides, in addition to simple phenylethanoid compounds. Isolation of active metabolites was performed and led to the isolation and identification of four compounds. On the basis of docking study using HSP90 legend, kaempferol neohesperidoside showed a high cytotoxic potential supported by a high affinity score towards HSP90 legend protein. Conclusion: Jasminum multiflorum is a good candidate to isolate cytotoxic agents.

We herein report on the first chemical assessment of Erythrococca anomala (Juss. ex Poir.) Prain (Euphorbiaceae), a genus that was – to the best of our knowledge – not studied yet from a phytochemical perspective. A molecular networking strategy was implemented to rapidly identify the known specialized metabolites from untargeted MS/MS analyses of E. anomala leaves ethanolic extract. This strategy allowed for the identification of diverse C-glycosyl flavones and a cursory examination of MS/MS spectra could extend the GNPS-provided annotation to pinpoint the structural novelty of further derivatives. The isolation of the sought-after structures could be streamlined based on MS-guidance and their structures, determined through extensive NMR analyses, displayed structural features in line with MS²-based predictions. Anticipating sharp structural features at an early stage of the dereplication process through a critical assessment of the tandem mass spectrometric landmarks was essential to embark on the isolation of the newly reported structures owing to the elevated number of flavonoid glycosides isomers thereof formerly known, which would have deterred us from isolating them without the support of additional tandem mass spectrometric information. The isolation of the main components of the ethanolic extract completed the currently provided chemical report on E. anomala, also resulting in the description of a new phenylethanoid derivative (3) and of a new orcinol-based dimer (4). Anomaloflavone (1) exhibit significant activities with minimal inhibitory concentration values of 25 µg/mL against Staphylococcus aureus and Mycobacterium smegmatis while failing to exert an antibacterial activity against Pseudomonas aeruginosa, while being devoid of cytotoxicity against SiHa cells.

Salvia viridis is a rich source of pharmacologically-important polyphenolic compounds with anti-inflammatory, antioxidant and anticancer activities. The aim of the present study was to optimise the large-scale cultivation of sage shoots in the Plantform bioreactor. It evaluated the effect of culture duration (two or three weeks), the use of a semi-continuous system and the immersion frequency in a liquid medium (every 80 or 170 min) on the growth and accumulation of secondary metabolites. The content of bioactive phenolic acids and phenylethanoids in the obtained material was determined using HPLC. The most efficient growth parameters, expressed as fresh (26.99 g) and dry weight (3.51 g) as well as proliferation ratio (18.6), were observed for shoots grown in a fed-batch system, immersed every 80 min; this approach yielded a 33-fold biomass increase within four weeks. However, the most efficient production of bioactive compounds was achieved for shoots grown for three weeks in a batch system, immersed every 80 min: total phenolic acid, total phenylethanoid and total phenol contents of 18.3, 11.4 and 29.7 mg/g DW. In these conditions, within three weeks, total phenolic acid level was almost 10 times higher than that found in the aerial parts of four-month-old soil-grown plants with a similar phenylethanoid level. Hence, the described S. viridis shoot culture cultivated in the Plantform bioreactor may be an alternative efficient source of plant material rich in valuable compounds. Optimization of culture conditions (culture duration, the use of fed-batch mode, frequency of the medium application) for growth and productivity of bioactive compounds in Salvia viridis shoots cultivated in the Plantform bioreactor.

Echinacoside (ECH), acteoside (ACT), and isoacteoside (ISAT), the typical phenylethanoid glycosides (PhGs) in cistanches herba, have various pharmacological activities. However, the ECH, ACT and ISAT have extremely low oral bioavailability, which is related to their metabolism under the intestinal flora. Previous studies showed that intestinal metabolites were the hepatoprotective substances in vivo, but the research on whether PhGs has effects without intestinal bacteria has not been studied. In this paper, ECH, ACT and ISAT were incubated with human or rat intestinal bacteria for 36 h. After incubating with human bacteria for 36 h, three prototype compounds were not detected and were mainly biotransformed to 3-HPP and HT. In the network pharmacology, a total of 6 common targets were obtained by analysing the prototypes, the metabolites and the liver injury. It was found that the combinations of three metabolites and common targets were more stable than those of the prototypes and common targets by molecular docking. Meanwhile, hepatocellular apoptosis, proliferation, inflammation and oxidative responses might play important roles in the mechanisms of the metabolites exerting hepatoprotective activities. Then normal and pseudo-sterile mice experiments were adopted to further compare the hepatoprotective activities of prototypes and metabolites. Animal experiment results showed that the prototypes and the metabolites in the normal mice had significantly hepatoprotective activity. Interestingly, in the pseudo-germfree mice, the metabolites showed significant hepatoprotective effect, but the prototypes had not effect. It indicated that the prototype cannot exert liver protective activity without the effect of intestinal bacteria.

The wound healing properties of Teucrium polium L., a plant used in the Algerian traditional medicine for the treatment of wounds, have been investigated using an excision wound model in rabbits. An ointment was prepared with two concentrations (5 and 10%) of a methanolic extract of the aerial parts. Both preparations showed significant effect on the wound contraction when compared to the control and the group treated with petroleum jelly. In addition, acute dermal and oral toxicity was assessed in animal models. The absence of signs of toxicity on the skin of rabbits indicated the safety of the ointment. After oral administration in mice at doses of 1000 and 2000 mg/kg b.wt, no signs of liver and kidney toxicity were detected by analysis of biochemical parameters and by histological examination. The composition of the methanolic extract was investigated by HPLC-PDA-MS analysis, and a comprehensive profile of phenolic compounds was established, with 14 flavonoids and phenylethanoid glycosides identified as the main polyphenolic constituents. Overall, the data support the use of T. polium as a wound healing agent in the Algerian traditional medicine.

For the first time inflorescences of a plant species from the genus Plantago (Pantaginaceae)—Plantago lanceolata L. (Ribwort Plantain), a known medicinal plant, were subjected to studies of phenolic compounds, which resulted in an isolation of two new compounds: a flavonoid—isorhamnetin 3-O-α-L-4C1-arabinopyranosyl-(1→2)-β-D-4C1-glucopyranoside) (1) and a phenylethanoid glycoside—2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinofuranosyl-(1→2)-[α-L-1C4-rhamnopyranosyl-(1→3)][E-caffeoyl-1→4]-β-D-4C1-glucopyranoside (14), along with fourteen known compounds—eight flavonoids (2–9) and six phenylethanoid glycosides (10–13, 15–16). The chemical structures were established by 1 D and 2 D NMR and HRESIMS spectral methods. The known phenylethanoids were the same as reported for leaves or aerial parts of P. lanceolata or other Plantago species. The flavonoids appeared to be only flavonols, mainly isorhamnetin 3-O- and 3,4’-O- glycosides, and thus completely different from flavones, mainly luteolin and apigenin glucuronides, previously reported in the leaves. The possible medicinal and chemotaxonomic relevance of the phenolics found in P. lanceolata inflorescences were taken into consideration.

Phlomis brevidentata H.W.Li Radix (PbR) is a rare traditional Tibetan medicine, and it is widely used in the Chinese Tibetan region for the treatment of pharyngitis, pneumonia, and so forth. Nevertheless, there is very little research on its modern pharmacy, and the active ingredients and mechanisms against these diseases remain unknown. In this study, we employed the qualitative analysis and pharmacokinetic based on LC–MS technology and network pharmacology to explore the active ingredients and mechanisms of PbR for treatment of pneumonia. Ultraperformance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC-Q-TOF/MS) methodology was applied to identify the chemical composition of PbR. Meanwhile, a UPLC-MS/MS method was developed to quantify three active constituents (sesamoside, shanzhiside methyl ester, and barlerin) in rat plasma for the pharmacokinetic analysis after oral administration of PbR. Finally, in order to clarify the anti-pneumonia mechanism of this rare Tibetan medicine, a comprehensive network pharmacology strategy was applied. As a result, a total of 23 compounds were identified in PbR, including 14 iridoid glycosides, 7 phenylethanoid glycosides, and 2 other kinds of compounds. Pharmacokinetic studies have shown that the three compounds exhibit extremely similar pharmacokinetic characteristics, possibly due to their highly analogous chemical structure. We speculate that the iridoid glycosides may be the main active component in PbR. Then, the three iridoid glycoside constituents absorbed into blood were subjected to network pharmacology analysis for treatment of pneumonia. Compound-target-disease, gene ontology bioanalysis, KEGG pathway, and other network pharmacology analysis methods were applied to reveal that five main targets of the three iridoid glycosides, namely, GAPDH, ALB, MAPK1, AKT1, and EGFR, were significant in the regulation of the above bioprocesses and pathways. These results provide a basis for elucidating the bioactive compounds and the pharmacological mechanisms of P. brevidentata H.W.Li radix under clinical applications.

Species of Betonica L. genus are widespread in Ukraine and contain different groups of biologically active substances: hydroxycinnamic acids, flavonoids, tannins, iridoids, terpenoids, steroids, essential oil, organic acids, vitamin K, nitrogen-containing compounds, phenylethanoid glycosides. Species of Betonica L. genus show a wide range of pharmacological activity (anti-inflammatory, antioxidant, choleretic, diuretic, sedative, antitumor, antihypertensive, etc.) and phenolic compounds are one of the most important and promising groups of biologically active substances of these plants. The aim.The aim of the work was to conduct a comparative study of the phenolic compounds of the herb of Betonica L. genus species of flora of Ukraine. Materials and methods.The object of the study was the herb of Betonica peraucta and Betonica brachydonta harvested in the phase of mass flowering of the plant in Ivano-Frankivsk region. The study of phenolic compounds was carried out by paper chromatography, HPLC and spectrophotometry. Results.7 components of tannins, 4 flavonoids, 5 hydroxycinnamic acids, 2 coumarins were identified and quantified by HPLC in the studied raw material. The quantitative content of the main groups of phenolic compounds in the herb of Betonica peraucta and Betonica brachydonta was determined by the method of absorption spectrophotometry: polyphenols – 5.96 % and 4.82 %, tannins – 1.62 % and 0.68 %, flavonoids – 2.07 % and 1.13 %, hydroxycinnamic acids – 7.01 % and 3.58 %, respectively. Conclusions.As a result of the conducted studies it was found that the content of phenolic compounds in the herb of Betonica peraucta is significantly higher than in the herb of Betonica brachydonta. Therefore, this species is promising for further research and creation of new drugs

Background. To investigate the effects of phenylethanoid glycosides (PhGs) extracted from Herba Cistanches on the behavioral and cognition capacity of the APP/PSI transgenic mice with Alzheimer’s disease (AD). Methods. AD mice were randomly divided into the control group, model group, donepezil group, PhG groups, and verbascose group, respectively. Three weeks later, the animals were subject to behavioral and cognition evaluation by the nesting test, Morris water maze test, and step-down test. Results. The cognition capacity in these groups showed a significant increase compared with that in the model group. The step-down test indicated that the errors induced by the memory decrease in the PhG groups and verbascose group showed a significant decrease compared with those in the model group ( P < 0.05 ). Conclusions. PhGs attenuated the cognitive dysfunction features of the APP/PSI transgenic gene. Besides, PhGs were the active components for the anti-AD activity of H. Cistanches.

Elucidating the therapeutical basis and functional mechanism of traditional Chinese medicine (TCM) is still a challenge faced by researchers since the effects of TCM are always achieved by the interactions of multiple components and multiple targets. In this study, an integrated strategy using a combination of chemical profiling, network pharmacology and in vitro experimental validation was applied to profile the trace constituents of TCM and characterize their functional mechanism, and Rhizoma coptidis (RC) was used as an example. As a result, a total of 55 compounds were identified or tentatively characterized in the water extract of RC, including 22 organic acids, 17 alkaloids, 8 lignans, 2 flavonoids, 4 phenylethanoid glycosides, and 2 other types of compounds. Meanwhile, a potential novel compound (compound 41) – one of the alkaloids – was found and characterized. Notably, organic acids in RC were systematically characterized for the first time. Moreover, the pharmacological targets of the 46 main constituents of RC were predicted using the network pharmacological method, and 234 of them were involved in diabetes mellitus (DM). KEGG analysis indicated that the Rap1 signaling pathway, the cAMP signaling pathway, the PI3K–Akt signaling pathway, and inflammatory mediator regulation of TRP channels were the core signaling pathways for RC in the treatment of DM. Further, the anti-inflammatory effects of RC, correlated with inflammatory mediator regulation of TRP channels, were confirmed by using the LPS-induced RAW 264.7 cell model. Meanwhile, the downstream pathway (NF-kB) of TRP channels was validated by western blot. Our work comprehensively provided the material basis and potential pharmacological mechanism of RC against inflammation in DM; in the meantime, a new insight for elucidating the functional mechanism of TCM was also supplied.

Buddleja cordata Kunth (Scrophulariaceae) is an important medicinal herb widespread in Mexico that produces diverse phenolic compounds; among others, the pharmacologically important phenylethanoid glycoside (PeG) verbascoside (VB, also named acteoside). This work describes the effects of the metabolic precursor, L-phenylalanine (L-Phe), and the elicitor, methyl jasmonate (MeJa), on biomass accumulation and VB production in a B. cordata cell-line under suspension culture conditions. Cultures were exogenously fed with different concentrations of the precursor and elicitor at the early and late stages of the exponential growth phase. Precursor or elicitor addition was most effective when added in the late-exponential phase. Cultures fed with 600 µM L-Phe reached the highest production of VB after a 10-day exposure time (1.96 g L−1, which was 130% higher than in control cultures). Maximum VB production after elicitation (4.8 g L−1, with an overall increase of 213% above control level) occurred with 50 µM MeJa after an exposure time of 48 h. VB production yields reported in this work exceed those of previously reported biotechnological efforts using cell suspension cultures and other in vitro systems to increase phenylethanoid glycosides production, especially, VB.

Duzhong Jiangya tablet is a hypotensive drug. In this study, high-performance liquid chromatography-Fourier transform-ion cyclotron resonance-mass spectrometry technology was used to quickly identify its chemical composition. SinoChrom ODS-BP column (250 mm × 4.6 mm, 5 μm) was used. The mobile phase was acetonitrile(A)-0.1% formic acid solution(B). The flow rate was 1 mL/min. Extracted ion chromatogram was used to analyze the samples in positive and negative ion modes. Based on the accurate mass spectrometry information (such as quasi-molecular ions and fragment ions) obtained from the instrument, combined with reference compounds and literature, the chemical composition of Duzhong Jiangya Tablets was identified. A total of 131 compounds were identified, including four types of penylpropanoids, six types of phenylethanoid glycosides, 10 types of organic acids, 14 types of iridoids, 12 types of lignans, 18 types of alkaloids, seven types of coumarins, and 60 kinds of flavonoids. This established method can quickly and efficiently identify chemical constituents in Duzhong Jiangya tablet, lay a foundation for the research on the efficacy and quality of this traditional Chinese medicine, and provide a reference for the characterization of the chemical constituents of other traditional Chinese medicine preparations.

Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D – F. Their structures were elucidated by spectroscopic methods as β-(3,4-dihydroxyphenyl)ethyl 5-O-syringoyl-β-D-apiofuranosyloxy-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, and β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 2)-6-O-E-sinapoyl-β-D-glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5-O-α-L-rhamnopyranosyl-7-O-β-D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7-O-(2″-O-formyl)-β-D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety.

Introduction Craterostigma plantagineum and Lindernia brevidens are resurrection plants, so these plants can tolerate desiccation of their vegetative tissues. Different components and mechanisms contribute to desiccation tolerance and secondary plant metabolites, like phenolic compounds, may play a role during these processes. Objectives Secondary plant metabolites of the two resurrection plants, C. plantagineum and L. brevidens as well as the closely related desiccation sensitive species, L. subracemosa, were investigated regarding the polyphenol profile. Material and methods Secondary plant compounds were extracted with acidified methanol and analysed with ultra-high-performance liquid chromatography electrospray ionisation mass spectrometry (UHPLC-ESI-MS). Phenolic compounds were identified by comparing of ultraviolet (UV) and MSn -spectra with published data. All compounds were quantified as verbascoside equivalents by external calibration at the compound specific wavelength. Results In total, eight compounds that belong to the subclass of phenylethanoid glycosides and one flavone, luteolin hexoside pentoside, were identified. Two of these compounds exhibited a fragmentation pattern, which is closely related to phenylethanoid glycosides. The predominantly synthesised phenylethanoid in all of the three plant species and in every stage of hydration was verbascoside. The total content of phenolic compounds during the three stages of hydration, untreated, desiccated, and rehydrated revealed differences especially between C. plantagineum and L. brevidens as the latter one lost almost all phenolic compounds during rehydration. Conclusion The amount of verbascoside correlates with the degree of desiccation tolerance and verbascoside might play a role in the protective system in acting as an antioxidant.

Using various chromatographic separations, five iridoid glucosides (1―5) and five phenylethanoid glycosides (6―10) were isolated from the Plantago major whole plants and included two new compounds: 10-acetylarborescoside (1) and plantainoside G (6). Their structures were elucidated by detailed analysis of 1D and 2D NMR data, HR QTOF MS data, and experimental and calculated ECD data. The isolated compounds exhibited moderate inhibitory effects on NO overproduction in LPS-stimulated BV2 microglial cells, with IC50 values ranging from 44.2–62.3 μM.

Objective The objective of this study was to verify the lipid-lowering effect of Juhe Fang extract (JHFE) and to determine its characteristic chemical profile in vitro and in vivo. Methods A hyperlipidemia model was established by feeding mice a high-fat diet (HFD). After treatment for 30 days, serum total cholesterol (TC), triglyceride (TG), high-density lipoprotein cholesterol (HDL-C) and low-density lipoprotein cholesterol (LDL-C) levels were measured with an automatic biochemistry analyzer. The components from JHFE obtained from in vivo and in vitro experiments were investigated using an UPLC-Q Exactive-Orbitrap MS/MS. Results The TC, TG, and LDL-C in the serum significantly decreased and the HDL-C significantly increased after JHFE treatment. A total of 95 compounds from JHEF including 15 phenolic acids (PA), 4 phenylethanoid glycosides (PG), 24 flavonoids (F), 14 triterpenoids (T), 10 diterpenoid glycosides (D), 18 alkaloids (A) and 10 others (O) were identified. Trigonelline was discovered for the first time in a herbal medicine of Juhe Fang. Furthermore, 68 compounds were identified in vivo including 28 prototype compounds and 40 metabolites. The metabolic characteristics of these components were revealed including identification of new metabolites of 4-hydroxyphenyl ethyl-8-O-[α-L- arabinopyranosyl-(1 → 6)]-β-D-glucopyranoside (PEG) and lirinidine. A total of 43 components from JHFE were absorbed and/or metabolized. The contribution rate of each type of chemical component from JHFE to its lipid-lowering effect from high to low were A, F, PG, PA, D and T. Conclusion The results of this study showed that JHFE demonstrated a significant lipid-lowering effect in a high-fat diet (HFD)-induced hyperlipidemia mouse model. Specific types of PA, PG, F, D, T and A formed the pharmaceutical architecture of the lipid-lowering effect of JHFE. This study should prove useful for clarifying the components responsible for the lipid-lowering effect of JHFE and provide a basis for precision quality control research.

Phenylethanoid glycosides (PhGs) are generally water‐soluble phenolic compounds that occur in many medicinal plants. Until June 2020, more than 572 PhGs have been isolated and identified. PhGs possess antibacterial, anticancer, antidiabetic, anti‐inflammatory, antiobesity, antioxidant, antiviral, and neuroprotective properties. Despite these promising benefits, PhGs have failed to fulfill their therapeutic applications due to their poor bioavailability. The attempts to understand their metabolic pathways to improve their bioavailability are investigated. In this review article, we will first summarize the number of PhGs compounds which is not accurate in the literature. The latest information on the biological activities, structure–activity relationships, mechanisms, and especially the clinical applications of PhGs will be reviewed. The bioavailability of PhGs will be summarized and factors leading to the low bioavailability will be analyzed. Recent advances in methods such as bioenhancers and nanotechnology to improve the bioavailability of PhGs are also summarized. The existing scientific gaps of PhGs in knowledge are also discussed, highlighting research directions in the future.

Background Plant species from the genus Tecoma are found in tropical and subtropical regions around the world. Some of them are grown as ornamental plants and others can be used as medicinal plants. In the present study, ethanolic extracts from trunks and leaves of Tecoma species were tested in vitro using assays against the Zika virus. Methods There was a total of 8 extracts obtained from different anatomical parts of three Tecoma species. The Tecoma castaneifolia, T. garrocha, T. stans var. angustata and T. stans var. stans were prepared by percolation with ethanol. The antiviral activity was assayed in vitro against the Zika virus by the MTT colorimetric method (n = 3). The UPLC-DAD-MS analysis of ethanolic extracts was performed from all the studied species. The biofractionation of T. stans var. stans trunk extract using different separation techniques led to the isolation of crenatoside compound. Results Ethanolic extract from Tecoma species leaves were more active against the Zika virus (EC50 149.90 to 61.25 μg/mL) when compared to the trunk extracts tested (EC50 131.0 to 66.79 μg/mL and two were not active). The ethyl acetate and aqueous fractions obtained from T. stans var. stans trunk were active against the Zika virus with EC50 values of 149.90 and 78.98 μg/mL, respectively. Crenatoside is a phenylethanoid glycoside isolated from the ethyl acetate of T. stans var. stans trunk extract. This compound was tested and exhibited EC50 34.78 μM (21.64 μg/mL), thus demonstrating a better result than the original ethanolic extracts as well as others extracts of Tecoma species, and it was more active than the positive control, ribavirin (386.84 μM). Furthermore, its selectivity index was at least 2.5 times higher than the tested ethanolic extracts and 11.1 times more potent than ribavirin. Conclusion The Tecoma species demonstrated interesting in vitro activity against the Zika virus. The crenatoside, phenylethanoid glycoside that was for the first time isolated from Tecoma stans var. stans, exhibited a potent and relevant anti-Zika virus activity, being more active than ribavirin (positive control). The data show that crenatoside, was a promising compound with in vitro antiviral activity against the Zika virus.

Investigation of dried whole herb of Callicarpa macrophylla Vahl. resulted in the isolation of two new phenylethanoid glycosides, macrophylloside E (1), macrophylloside F (2), together with eight known phenylethanoid glycosides (3-10). Their structures were established by extensive spectroscopic methods. In addition, all phenylethanoid glycosides (1–10) were evaluated for their antioxidant activity by DPPH assay and showed high to moderate effect (IC50 from 2.72 to 38.65 μM).

Background: Eremostachys macrophylla Montbr. & Auch. is one of the wild growing species of herbs found in East Azerbaijan province of Iran. These species are used in folk medicine for the healing of wound, treatment of snake bites, rheumatism and joint pains. The primary aim of this study was to obtain natural pure compounds and this was done by subjecting the aerial parts of Eremostachys macrophylla Montbr. & Auch. to phytochemical analysis. Methods: The air-dried and crushed aerial parts were respectively extracted with n-hexane, dichloromethane (DCM) and methanol (MeOH) solvents using a soxhlet apparatus. The 10%, 20% and 40% of MeOH in water Sep-Pak fractions of the MeOH extract were subjected to a preparative reversed- phase high performance liquid chromatography (RP-HPLC). Also, the isolated pure compounds were identified by one-dimensional nuclear magnetic resonance (1D-NMR) spectroscopic technique. Results: The results obtained in this study showed the presence of seven pure components; (1) Lamalbide, (2) Sesamoside, (3) Phlomiol, (4) Verbascoside, (5) Luteolin-7-O- glucoside, (6) Apigenin-7-O- rutinoside and (7) Kaempferol-3-O- glucoside with iridoid, phenylethanoid and flavonoid structures. Conclusion: The results from the study demonstrated that the aerial parts of E. macrophylla could be a good source of iridoids, phenylethanoids and flavonoids.

Callicarpa kwangtungensis Chun is a traditional Chinese medicine that has various therapeutic effects. Despite its wide use in Chinese medicine, the study is still quite limited, especially its chemical compositions. In this research, an ultra-high-pressure liquid chromatography coupled with Q Exactive hybrid quadrupole-orbitrap high-resolution accurate mass spectrometry tandem mass spectrometry method was utilized to analyze its chemical compositions for the first time. As a result, a total of 124 compounds, including 20 phenylethanoid glycosides, 31 flavonoids, 36 organic acids, 26 terpenoids and 11 phenols, were identified or tentatively characterized in 30 min. Among them, 49 compounds, including 5 phenylethanoid glycosides, 12 flavonoids, 16 organic acids, 12 terpenoids, and 4 phenols, were identified in Callicarpa kwangtungensis Chun for the first time. Besides, the fragmentation pathways were also discussed. This research established a rapid and reliable method to analyze the chemical compositions of complicated herb without the process of isolation, and provide abundant information on the chemical material basis for further bioactivity and quality control studies.

New phenylethanoid, glucooleoacteoside (2), along with 18 known compounds were isolated from the aqueous extract of Osmanthus fragrans. The structure of new compound was elucidated on the base of IR, HR-ESI-MS, 1D NMR, 2D NMR and DEPT analysis. Bioactivity investigation into human dermal fibroblasts (HDF) proliferation, type I collagen expression, and MMP-1 expression were examined with six phenylethanoids. We found that compounds 1, 3, 4, 7, and 9 showed moderate bioactivities. In conclusion, we demonstrated that the aqueous extract of flower of O. fragrans contained phenylethanoid-rich constituents which revealed bioactivities at the cellular level of HDFs.

Background: The genus Verbascum is well documented for its antioxidant potential but Verbascum sinaiticum is comparatively less studied plant. The current study was carried out to search for antioxidant nutraceuticals from this species. Objective: To explore the antioxidant potential of Verbascum sinaiticum and to identify its active constituents. Methods: The methanolic extract of air-dried aerial part of the Verbascum sinaiticum was partitioned with hexane, chloroform and ethyl acetate. The water-soluble part of ethyl acetate afforded six phenylethanoid glycosides by repeated chromatography over Sephadex LH-20, silica gel and ODS columns. Antioxidant activity of solvent extracts and isolated constituents were evaluated by DPPH, ABTS and FRAP assays. Results: Six phenylethanoid glycosides was isolated and characterized as Verbascoside, Eukovoside, Martynoside, Jionoside D, Campneoside I and Campneoside II, from the most active fraction. Conclusion: Verbascum sinaiticum demonstrated prospective antioxidant activity. The watersoluble part of EtOAc (WSEAE) was found the most active extract whereas Verbascoside was identified as the most potent constituent. All isolated compounds exhibited significant antioxidant activity whereas their synergistic effect was found prominent in the parent fraction.

Context Fruit of Avicennia marina (Forsk.) Vierh. (Acanthaceae) is used as a Chinese herb. Studies have found that it contains marinoid J, a novel phenylethanoid glycoside (PG) compound, but its neuroprotective functions are largely unknown. Objective This study evaluated the effects of marinoid J on vascular dementia (VD) and determined its potential mechanisms of action. Materials and methods The VD model was established by the ligation of the bilateral common carotid artery in Sprague–Dawley rats, who received daily intragastrically administration of saline, marinoid J (125 or 500 mg/kg body weight/d), or oxiracetam (250 mg/kg body weight/d) for 14 days (20 rats in each group). The Morris water maze (MWM) was used to evaluate cognitive performance. The hippocampus was subjected to histological and proteomic analyses. Results Marinoid J shortened the escape latency of VD rats (31.07 ± 3.74 s, p

The growing popularity of integration of functional compounds into food and pharmaceutical products has greatly influenced the intense investigation of aromatic plants as its notable sources. One of the insufficiently explored plant species-Mountain Germander (Teucrium montanum)-may represent a prominent source of biologically active components-polyphenols. Hence, to maximally enhance their recovery, conventional (HAE) and non-thermal extraction methods-microwave-assisted extraction (MAE) and subcritical water extraction (SWE) were employed by using multiple response surface methodology (RSM). Optimization of temperature, solid-to-solvent ratio, and extraction time was evaluated by measuring total phenolic content (TPC) and antioxidant capacity (DPPH and ABTS assays), with the further estimation of the extraction efficiency of two selected phenylethanoid glycosides present in final extracts-verbascoside and echinacoside determined by HPLC analysis. The optimum HAE, MAE, and SWE extraction conditions with the highest measured dependent variables were, as follows: 100 °C, 0.5 g/50 mL and 30 min, 90 °C, 0.5 g/50 mL and 9 min, 200 °C, 0.5 g/50 mL and 15 min, respectively. Regarding examined phenylethanoid glycosides, HAE extract showed to be its richest source (16.64 mg/g dw) while SWE was estimated as at least suitable extraction technique (5.42 mg/g dw). In conclusion, this study outlined the most appropriate extraction technique and conditions for the recovery of selected phenolic compounds using RSM and gave closely insight into the antioxidative potential of valuable ethnomedicinal plant from the Balkan peninsula-Teucrium montanum.

Electron-rich esters are ubiquitously distributed in natural products and play a central role in bioactivities. Herein, we disclose an efficient, mild, and general esterification approach to the synthesis of these esters by employing gold(I)-catalyzed acylation reaction with alkyne-tethered mixed anhydrides and alcohols. This method can be applied to ester-bond formation in complex substrates and facilitates efficient synthesis of acteoside, which belongs to the family of phenylethanoid glycosides and possesses a broad range of bioactivities.

Osteoarthritis (OA) is a complex disease, source of pain and disability that affects millions of people worldwide. OA etiology is complex, multifactorial and joint-specific, with genetic, biological and biomechanical components. Recently, several studies have suggested a potential adjuvant role for natural extracts on OA progression, in terms of moderating chondrocyte inflammation and following cartilage injury, thus resulting in an overall improvement of joint pain. In this study, we first analyzed the phenylethanoid glycosides profile and the total amount of polyphenols present in a leaf aqueous extract of Verbascum thapsus L. We then investigated the anti-inflammatory and anti-osteoarthritic bioactive potential of the extract in murine monocyte/macrophage-like cells (RAW 264.7) and in human chondrocyte cells (HC), by gene expression analysis of specifics inflammatory cytokines, pro-inflammatory enzymes and metalloproteases. Six phenylethanoid glycosides were identified and the total phenolic content was 124.0 ± 0.7 mg gallic acid equivalent (GAE)/g of extract. The biological investigation showed that the extract is able to significantly decrease most of the cellular inflammatory markers, compared to both control cells and cells treated with Harpagophytum procumbens (Burch.) DC. ex Meisn, used as a positive control. Verbascum thapsus leaf aqueous extract has the potential to moderate the inflammatory response, representing an innovative possible approach for the inflammatory joint disease treatment.

As the sixth-largest Angiosperm family, Lamiaceae contains more than 245 genera and 7886 species that are distributed worldwide. It is also the third-largest family based on the number of taxa in Turkey where it is represented by 46 genera and 782 taxa with a high endemism ratio (44%). Besides, Lamiaceae are rich in plants with economic and medicinal value containing volatile and nonvolatile compounds. Many aromatic plants of Lamiaceae such as Salvia, Sideritis, Stachys, Phlomis, and Teucrium species are used in traditional herbal medicine throughout Turkey as well as in other Mediterranean countries. Salvia (Sage tea “Adaçayı”), Sideritis (Mountain tea “Dağçayı”), Stachys (Hairy Tea “Tüylü Çay”), and Phlomis (Turkish sage “Çalba or Şalba”) are the largest genera that are used as herbal teas. This review focuses on the volatile and nonvolatile compounds of Lamiaceae from the genera Phlomis and Eremostachys of the subfamily Lamioideae with emphasis on iridoids, phenylethanoid glycosides, and essential oils.