Twig Extracts Research Articles

Allelopathic Potential of Three Oil Enriched Plants against Seedling Growth of Common Field Crops

Current study aims to investigate into the allelopathic potential of the different parts (leaf, bark, stem, twig and root) of three oil-enrich plant species of Bangladesh viz., Jatropha curcus, Ricinus communis and Aphanamixis polystachya. The aqueous extract of those plant parts were diluted into four different concentrations viz., 1:5, 1:10, 1:15, 1:20 (w/v) and tested against the seedling growth of jute, rice, wheat, radish, tomato, mungbean and mustard under control laboratory condition. A control (distilled water without extract) was also maintained in every cases and the bioassay experiment was replicated thrice. The results of this research showed that the shoot and root growth inhibition of rice, wheat, jute, tomato, radish, mungbean and mustard by leaf, bark, stem, twig and root extracts of J. curcus, R. communis and A. polystachya varied significantly. Compare to the shoot growth, the root growth of the test species inhibited more except J. curcus. The leaf and root have higher allelopathic potential than any other parts of the studied plants. Finally, it can be concluded here that J. curcus plant extracts has higher allelopathic potential than other two plants R. communis and A. polystachya. Therefore, J. curcus can be used as a candidate plant for isolation and identification of allelopathic substances for the development of new natural herbicides.

Antibacterial and Wound Healing Activity of Dipterocarpus alatus Crude Extract Against Methicillin-resistant Staphylococcus aureus-induced Superficial Skin Infection in Mice

Background: The bark oil of Dipterocarpus alatus Roxb. ex G. Don (resin tree) has been used for the treatment of ulcerated wounds in Ayurvedic medicine. However, information is still scarce about D. alatus extract and its constituents. Objectives: This study aimed to examine the antibacterial and wound healing effects of D. alatus crude extracts against methicillin-resistant Staphylococcus aureus (MRSA) in a superficial skin infection using a tape-stripping mouse model. Methods: Different parts (bark, leaves, twig, wood, and oleo-resin) of D. alatus were used for extraction. Crude extracts with two pure compounds (α,β-gurjunene and dipterocarpol) were examined for antibacterial activity against methicillin-susceptible S. aureus (MSSA) and MRSA in vitro. The in vivo antibacterial activity against MRSA was examined in a tape-stripping mouse model of superficial skin infection by evaluating transepidermal water loss (TEWL), colony counts from wound culture swabs, and H&E staining. Results: Dipterocarpus alatus twig extract showed the lowest MIC (250 µg/mL) and MBC (500 µg/mL) against MRSA among extracts from other D. alatus parts. In addition, α,β-gurjunene showed lower MIC (250 µg/mL) and MBC (250 µg/mL) against MRSA than dipterocarpol. In vivo, D. alatus twig extract significantly reduced the number of MRSA recovered from superficial wounds to levels comparable to the non-infected control group on the second day. Oleo-resin, D. alatus wood extract, α,β-gurjunene, and dipterocarpol also significantly reduced the number of MRSA. Moreover, D. alatus twig extract and dipterocarpol healed infected wounds at rates comparable to the non-infected control group. From H&E staining of wounds, fibrin accumulation and neutrophil infiltration were attenuated in mice treated with D. alatus twig extract and dipterocarpol. Conclusions: Dipterocarpus alatus twig extract and dipterocarpol possess antibacterial and wound healing properties against MRSA-induced superficial skin infection in mice.

Allelopathic potential and phenolic allelochemicals discrepancies in Ficus carica L. cultivars

The phytotoxic effect of some tree species could act as an ecological filter through chemical production that influences plant growth of other species. Despite this widespread interest, few studies have investigated the allelopathic effect of some Moraceae species, while this mechanism has not been studied in Ficus carica. To address this research, we attempted to identify the allelopathic mechanisms of thirteen local preserved fig cultivars on the germination and seedling growth of common weeds and standard target species. The results stated that all fig extracts displayed significant phytotoxic impact, and the degree of inhibition was appeared to be dependent on the cultivars and target species. In general, leaf extracts were more toxic and significantly influenced the seedling elongations, as compared to twig extracts. It was clearly marked that the germination and growth of weed species were totally affected by leaf aqueous and methanol extracts of cultivars Kahli and Bouhouli, respectively, at 40 g/L and 6 g/L. The phytochemical analysis through high performance liquid chromatography detected similar profile among cultivars but with a significant disparity in phenolic composition. Among the identified compounds, rutin is the major flavonoid compound recorded in cv. Zidi and was highly accumulated in leaf rather than in twig. It was obvious that the different fig cultivars or even their tissues can be characterized and clustered in three groups based on their allelopathic potential and phenolic compounds.

A new xanthone and a biphenyl from the flower and twig extracts of Garcinia mckeaniana

The phytochemical investigation of the flower and twig extracts of Garcinia mckeaniana yielded a new xanthone, mckeanianone F (1) and a new biphenyl, mckeaniabiphenyl (2) together with 15 known compounds. The isolated compounds were characterized using spectroscopic techniques and mass spectrometry. Some of the isolated compounds from the twigs exhibited antimalarial and cytotoxic activities.

Dasymaschalolactams A-E, Aristolactams from a Twig Extract of Dasymaschalon dasymaschalum.

Five new aristolactam alkaloids (1-5), dasymaschalolactams A-E, and the first isolation of dasymaschalolactone (17) as a natural product, together with 19 known compounds (6-16 and 18-25) were isolated from the twig extract of Dasymaschalon dasymaschalum. Their structures were elucidated by spectroscopic methods as well as comparisons made from the literature. Compounds 20 and 21 showed α-glucosidase inhibitory activities with IC50 values of 4.5 and 24.7 μM, respectively.

UHPLC-QTOF-MS phytochemical profiling and in vitro biological properties of Rhamnus petiolaris (Rhamnaceae)

The genus Rhamnus has a great attention as source of bioactive compounds. So, this work aimed to investigate phytochemical profile and biological activity of water and methanolic extracts of different parts of Rhamnus petiolaris Boiss. & Balansa, namely twigs, leaves, mature and unmature fruits. The in vitro antioxidant activity, enzyme inhibitory properties, along with their polyphenol and anthraquinone profiles were determined by untargeted metabolomics. Results showed that methanolic and aqueous unmature fruit extracts were the most effective 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) scavenger (470.96 mg trolox equivalent (TE)/g and 394.96 mg TE/g, respectively). The aqueous unmature fruit extract displayed the most potent cupric and ferric reducing power and showed the highest total phenolic contents (TPC) (137.17 mg gallic acid equivalent (GAE)/g). The methanolic twig extract showed the highest enzymatic inhibitory property against of α-glucosidase, tyrosinase, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE). On the basis of the correlation coefficients calculated separately for all experimental parameter pairs, flavonols and anthocyanins highly correlated with DPPH, whereas tyrosols correlated with BChE activity. Multivariate statistics following untargeted metabolomics allowed to describe the differences in polyphenols and anthraquinones, as affected by the extraction solvent used. Mature and unmature fruits were substantially comparable and were affected in a similar way by the extraction conditions, while different profiles were recorded for Rhamnus leaves and twigs. These findings indicate that the recovery efficiencies of specific subclasses of compounds (above all when considering flavonoids, phenolic acids and anthraquinones) as a function of the matrix and extraction chosen, significantly affect the phytochemical profile and biological activity of Rhamnus.

Untargeted Metabolomic Profiling, Multivariate Analysis and Biological Evaluation of the True Mangrove (Rhizophora mucronata Lam.).

Currently, there is a renewed interest towards the development of plant-based pharmacophores. In this work, 16 extracts prepared from the leaves, twigs, roots and fruits of a hydro-halophyte, Rhizophora mucronata Lam. (Family: Rhizophoraceae), were studied for possible antioxidant activity and the phenolic profiles established. Thereafter, enzymatic inhibitory activities (α-amylase, α-glucosidase, tyrosinase, acetyl- (AChE), butyrylcholinesterase (BChE), lipase, and elastase) were assessed. The total phenolic, flavonoid, phenolic acid, tannin, flavanol and triterpenoid content were estimated using standard assays. An untargeted metabolomics-based approach, based on ultra-high-pressure liquid chromatography coupled to quadrupole-time-of-flight mass spectrometry (UHPLC-QTOF-MS) followed by multivariate statistics, was then used to comprehensively profile and describe the phenolics present. UHPLC-QTOF-MS allowed for putatively annotating 104 phenolic acids, 103 flavonols, 94 flavones, 71 anthocyanins, 66 tyrosols, 29 lignans, 15 alkylphenols and 10 stilbenes in the extracts. Nine strains (Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Methicillin-resistant Staphylococcus aureus (MRSA), Salmonella enteritidis, Sarcina lutea, Proteus mirabilis, Bacillus cereus and Candida albicans) were then used to investigate the antimicrobial properties. The methanolic twig extract exhibited significant reducing potential towards Cu (II)/Cu (I) and Fe (III)/Fe (II) (1336.88 ± 15.70 and 710.18 ± 21.04 mg TE/g, respectively) and was the most potent DPPH radical scavenger (807.07 ± 6.83 mg TE/g). Additionally, the methanolic twig extract showed significant inhibition against most targeted enzymes. Anti-microbial results showed that all extracts were active against MRSA. Multivariate analysis demonstrated that the phenolic profile of ethyl acetate extracts and leaves were the two most discriminative parameters in terms of solvents and organs, respectively. The present findings indicated that R. mucronata may be further explored for the management/prevention of oxidative stress, neurodegenerative complications and hyperpigmentation.

Anti-Platelet Properties of Phenolic Extracts from the Leaves and Twigs of Elaeagnus rhamnoides (L.) A. Nelson.

Sea buckthorn (Elaeagnus rhamnoides (L.) A. Nelson) is a small tree or bush. It belongs to the Elaeagnaceae family, and has been used for many years in traditional medicine in both Europe and Asia. However, there is no data on the effect of sea buckthorn leaves and twigs on the properties of blood platelets. The aim of the study was to analyze the biological activity of phenolic extracts from leaves and twigs of sea buckthorn in blood platelets in vitro. Two sets of extracts were used: (1) phenolic compounds from twigs and (2) phenolic compounds from leaves. Their biological effects on human blood platelets were studied by blood platelet adhesion, platelet aggregation, arachidonic acid metabolism and the generation of superoxide anion. Cytotoxicity was also evaluated against platelets. The action of extracts from sea buckthorn twigs and leaves was compared to activities of the phenolic extract (a commercial product from the berries of Aronia melanocarpa (Aronox®) with antioxidative and antiplatelet properties. This study is the first to demonstrate that extracts from sea buckthorn leaves and twigs are a source of bioactive compounds which may be used for the prophylaxis and treatment of cardiovascular pathologies associated with blood platelet hyperactivity. Both leaf and twig extracts were found to display anti-platelet activity in vitro. Moreover, the twig extract (rich in proanthocyanidins) displayed better anti-platelet potential than the leaf extract or aronia extract.

Uvarialuridols A-C, three new polyoxygenated cyclohexenes from the twig and leaf extracts of Uvaria lurida

The first phytochemical investigation of Uvaria lurida resulted in the isolation and identification of three new polyoxygenated cyclohexenes, (+)-(1R,2S,3R,6S)-uvarialuridols A-C (1–3), together with 10 known compounds (4–13). All new structures were elucidated by spectroscopic methods and HRESIMS. The absolute configurations of compounds 1 and 5 were confirmed by X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of compounds 2–4 were identified from comparisons of their specific rotations and ECD spectra with those of known compounds. Compound 11 showed α-glucosidase inhibitory activity with an IC50 value of 30 μM which was better than the standard control, acarbose (74 μM) whereas, compound 10 exhibited nitric oxide (NO) production inhibitory activity with an IC50 value of 37 μM.

Chemical Composition, Antioxidant and Cytotoxicity Activities of Leaves, Bark, Twigs and Oleo-Resin of Dipterocarpus alatus.

Dipterocarpus alatus (Dipterocarpaceae) is a medicinal plant whose use is well known for the treatment of genito-urinary diseases. However, there is no report of its cytotoxic potential. In this study, the chemical composition, antioxidant and cytotoxic activities of extracts of the leaves, bark, twigs and oleo-resin from D. alatus are investigated. Cytotoxicity was measured by the neutral red (NR) assay against HCT116, SKLU1, SK-MEL2, SiHa and U937 cancer cell lines and antioxidant capacity was evaluated by DPPH, ABTS radical scavenging, and ferric reducing antioxidant power (FRAP) assays. The chemical composition was analyzed by gas chromatography–mass spectrometry (GC-MS). Leaf, bark and twig extracts exhibited stronger antioxidant activity than oleo-resin, with bark extract showing the highest antioxidant activity and the highest total phenolic content. All samples showed more cytotoxic activity against the U937 cell line than HCT116, SKLU1, SK-MEL2 and SiHa cells with oleo-resin being more cytotoxic than melphalan against U937 cells. Chemical composition analysis of oleo-resin by GC-MS showed that the major components were sesquiterpenes, namely α-gurjunene (30.31%), (-)-isoledene (13.69%), alloaromadendrene (3.28%), β-caryophyllene (3.14%), γ-gurjunene (3.14%) and spathulenol (1.11%). The cytotoxic activity of oleo-resin can be attributed to the sesquiterpene content, whereas the cytotoxic and antioxidant activities of leaf, bark and twig extracts correlated to total phenolic content.

Biological properties of Elaeagnus rhamnoides (L.) A. Nelson twig and leaf extracts

BackgroundSea buckthorn (Elaeagnus rhamnoides (L.) A. Nelson, SBT) is a valuable plant because of its medical and therapeutic potential. Different bioactive compounds in SBT berries are of special interest to various researchers. However, not only sea buckthorn berries, but also leaves of this plant (both fresh and dried) contain a lot of nutrients and bioactive compounds, including phenolic compounds. The present study was carried out in order to investigate antioxidant and anticoagulant properties of sea buckthorn twig and leaf extracts (0.5–50 μg/mL) by using various in vitro models. Moreover, the aim of present experiments was to compare the biological activity of SBT leaf extract and SBT twig extract with selected berry extracts (a rich source of phenolic compounds): SBT berry extract (flavonoids being the dominant components), a commercial extract from the berries of Aronia melanocarpa (Aronox®), and a grape seed extract.MethodsWe determined the effect of plant extracts on the oxidative stress using selected markers of this process, i.e. the level of carbonyl groups in proteins. Additionally, we analysed the potential mechanism of modulation of hemostatic properties of human plasma (using selected coagulation times).ResultsSBT twig and leaf extracts were observed to exhibit an antioxidant activity against two strong biological oxidants: hydrogen peroxide (H2O2) and H2O2/Fe (the donor of hydroxyl radicals), which induced human plasma lipid peroxidation and protein carbonylation. Both extracts also showed anticoagulant properties.ConclusionsOur present results have demonstrated that extracts from different parts of SBT, especially berries and twigs, in comparison to well-known berries (aronia and grape), may also be viewed as a good source of active substances – antioxidants for pharmacological or cosmetic applications. Moreover, it is very important from an economic point of view to know that there is a possibility of obtaining phenolic compounds not only from the berries or leaves, but also from twigs, which constitute a production waste.

Identification of Antidiabetic Metabolites from Paederia foetida L. Twigs by Gas Chromatography-Mass Spectrometry-Based Metabolomics and Molecular Docking Study.

Paederia foetida L. (Rubiaceae) is a climber which is widely distributed in Asian countries including Malaysia. The plant is traditionally used to treat various diseases including diabetes. This study is to evaluate the enzymatic inhibition activity of Paederia foetida twigs extracts and to identify the metabolites responsible for the bioactivity by gas chromatography-mass spectrometry (GC-MS) metabolomics profiling. Three different twig extracts, namely, hexane (PFH), chloroform (PFC), and methanol (PFM), were submerged for their α-amylase and α-glucosidase inhibition potential in 5 replicates for each. Results obtained from the loading column scatter plot of orthogonal partial least square (OPLS) model revealed the presence of 12 bioactive compounds, namely, dl-α-tocopherol, n-hexadecanoic acid, 2-hexyl-1-decanol, stigmastanol, 2-nonadecanone, cholest-8(14)-en-3-ol, 4,4-dimethyl-, (3β,5α)-, stigmast-4-en-3-one, stigmasterol, 1-ethyl-1-tetradecyloxy-1-silacyclohexane, ɣ-sitosterol, stigmast-7-en-3-ol, (3β,5α,24S)-, and α-monostearin. In silico molecular docking was carried out using the crystal structure α-amylase (PDB ID: 4W93) and α-glucosidase (PDB ID: 3WY1). α-Amylase-n-hexadecanoic acid exhibited the lowest binding energy of -2.28 kcal/mol with two hydrogen bonds residue, namely, LYS178 and TYR174, along with hydrophobic interactions involving PRO140, TRP134, SER132, ASP135, and LYS172. The binding interactions of α-glucosidase-n-hexadecanoic acid complex ligand also showed the lowest binding energy among 5 major compounds with the energy value of -4.04 kcal/mol. The complex consists of one hydrogen bond interacting residue, ARG437, and hydrophobic interactions with ALA444, ASP141, GLN438, GLU432, GLY374, LEU373, LEU433, LYS352, PRO347, THR445, HIS348, and PRO351. The study provides informative data on the potential antidiabetic inhibitors identified in Paederia foetida twigs, indicating the plant has the therapeutic effect properties to manage diabetes.

Glyphaea brevis – In vitro antioxidant and in silico biological activity of major constituents and molecular docking analyses

Previous studies have revealed that leaf extracts of Glyphaea brevis possess antioxidant activity but the bioactivity and mechanisms of action of its major constituents remain unknown. This study evaluated in vitro antioxidant and free radical scavenging activities of Glyphaea brevis twigs and leaves, and probable toxicity profile, pharmacological activities and mechanisms of action of major phytoconstituents in silico. Phytochemical screening detected saponins, tannins, steroids, anthraquinones, flavonoids, terpenoids and phenolics in the extracts. HPLC fingerprinting revealed major compounds as ferulic, catechuic and coumaric acids. Twig extract contained more flavanols compared to the leaf extract while the leaf extract had more flavonol content. Extract of the twigs demonstrated higher ORAC, TEAC and FRAP compared to the leaf extract. In silico analyses predicted low acute toxicity risk and pharmacological activities which are in agreement with traditional use of the plant in the management of diseases such as dyspepsia, ulcers, chest pains, diarrhea, dysentery and sleeping sickness. The molecular docking studies revealed that coumaric acid and ferulic acid have the best binding for all proteins tested. In summary, Glyphaea brevis twigs possess higher antioxidant activity than the leaves and major constituents showed low toxicological potential and promising biological activities which support its ethnomedical use.

Purification of Cinnamic Acid and Aporphine Alkaloids from Enicosanthellum pulchrum Twig Extract and their Biological Activities

Background: Various methods of isolating compounds from plants have been described previously, which include conventional or modern techniques. A preparative-HPLC (prep-HPLC) system has become one of the most convenient methods, with high purity compound as well as consumes less purification time. Objective: This study is intended to purify compounds from E. pulchrum twig extract using prep- HPLC technique and to test all compounds in several biological activities. Methods: Prior to purification using prep-HPLC, the twig extract was injected onto HPLC to develop the method through its chromatograms. The established method from HPLC was used to separate the constituents using prep-HPLC. Purified compounds were elucidated through NMR and MS methods as well as through comparison with previously reported data. Three different biological activities were then conducted on the compounds, including cytotoxicity, DPPH, FRAP, and disc diffusion assays. Results: Cinnamic acid (1) and two aporphine alkaloids (liridine (2) and lysicamine (3)) have been successfully purified and identified. These compounds were first isolated from Enicosanthellum pulchrum using prep-HPLC. Cytotoxic activity revealed that liridine (2) showed strong inhibition against WEHI-3B leukaemic cells of 8.7 µM after 24 h of treatment. In contrast, cinnamic acid (1) and lysicamine (3) exhibited strong inhibitions in antibacterial activity against Staphylococcus aureus, S. epidermidis, Bacillus cereus, Pasteurella multocida and B. subtilis with more than 15 mm of inhibition zone. Conclusion: These phytochemical findings exhibit three isolated compounds from twig extract of E. pulchrum with diverse biological potential to be developed as new agents.

RRLC-DAD-ESI-MS based and bioactivity guided phytochemical analysis and separation of coumarins from raw extracts of Trigonostemon lutescens

As extensively active compounds, coumarins are rarely reported on the phytochemistry of the genus Trigonostemon. We herein proposed a fast strategy for analysis and separation of antitumoral active coumarins from the twigs of T. lutescens. Rapid Resolution liquid chromatography coupled with diode array detection and electrospray ionization mass spectrometry (RRLC-DAD-ESI-MS) analysis indicated the existence of coumarins in the twig extracts. Bioactivity guided phytochemical analysis assays revealed that the twig extract contained some active components that significantly inhibited cancer cell viability. Accordingly, a series of coumarins including a new furanocoumarin have been isolated from the twigs of T. lutescens by semi-preparative chromatographic separation. All compounds, especially furan-type coumarins, were reported for the first time from the genus Trigonostemon. The proposed strategy, by combining RRLC-DAD-ESI-MS based and bioactivity guided phytochemical analysis, exemplify a fast method for screening and identifying active components from raw extracts of herbs.

α-Glucosidase Inhibitory Flavonoids and Oxepinones from the Leaf and Twig Extracts of Desmos cochinchinensis.

Four new flavonoids (1-4), a new benzyl benzoate derivative (5), five new oxepinones (6-10), and 14 known compounds (11-24) were isolated from the leaf and twig extracts of Desmos cochinchinensis. Their structures were established by spectroscopic methods. The structure of 1 was also confirmed by X-ray diffraction data. The absolute configurations of 3, 4, and 6-10 were determined from comparisons of their ECD spectra with those of relevant reported compounds. Compounds 1, 2, 6, 8, 10, 12-15, and 17 showed α-glucosidase inhibitory activities with IC50 values ranging from 0.2 to 4.9 μM.

Detection of volatile pheromone candidates from the white-spotted longicorn beetle, Anoplophora malasiaca (Coleoptera: Cerambycidae)

Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae) is a serious pest that affects various crop trees and landscapes in Japan. We collected and analyzed volatiles from male and female A. malasiaca. 4-(n-Heptyloxy)butan-1-ol and its aldehyde, pheromone components in A. glabripennis and A. chinensis, were detected in the male volatile extracts and nonanal both in the male and female volatile extracts. Nonanal was absent from the extracts of twigs of the willow host plant. Gas chromatograph-electroantennographic responses showed that nonanal and 4-(n-heptyloxy)butan-1-ol elicited responses from both male and female antennae, but 4-(n-heptyloxy)butanal did not. Volatiles of eight artificially reared males, analyzed every 3 or 4 days for 60 days from adult emergence showed that they all produced nonanal and 4-(n-heptyloxy)butan-1-ol. The two compounds produced no short-range female attraction but in males, the short-range attraction to nonanal was dose dependent and significant in a higher dose, but did not depend on 4-(n-heptyloxy)butan-1-ol. When wounded willow twigs were added to nonanal and 4-(n-heptyloxy)butan-1-ol, the frequency of male responses was higher than in all other treatments, but the same as wounded willow twigs alone. The wounded host plant willow twigs might thus be enough for male attraction. The identified volatiles from the beetles in the present study might have a weaker function for attraction from the distance compared to their host plant volatiles.

Bioassay-Guided Isolation and Structure Elucidation of Fungicidal and Herbicidal Compounds from Ambrosia salsola (Asteraceae).

The discovery of potent natural and ecofriendly pesticides is one of the focuses of the agrochemical industry, and plant species are a source of many potentially active compounds. We describe the bioassay-guided isolation of antifungal and phytotoxic compounds from the ethyl acetate extract of Ambrosia salsola twigs and leaves. With this methodology, we isolated and identified twelve compounds (four chalcones, six flavonols and two pseudoguaianolide sesquiterpene lactones). Three new chalcones were elucidated as (S)-β-Hydroxy-2′,3,4,6′-tetrahydroxy-5-methoxydihydrochalcone (salsolol A), (S)-β-Hydroxy-2′,4,4′,6′-tetrahydroxy-3-methoxydihydrochalcone (salsolol B), and (R)-α, (R)-β-Dihydroxy-2′,3,4,4′,6′-pentahydroxydihydrochalcone (salsolol C) together with nine known compounds: balanochalcone, six quercetin derivatives, confertin, and neoambrosin. Chemical structures were determined based on comprehensive direct analysis in real time-high resolution mass spectrometry (HR-DART-MS), as well as 1D and 2D NMR experiments: Cosy Double Quantum Filter (DQFCOSY), Heteronuclear Multiple Quantum Coherence (HMQC) and Heteronuclear Multiple Bond Coherence (HMBC), and the absolute configurations of the chalcones were confirmed by CD spectra analysis. Crystal structure of confertin was determined by X-ray diffraction. The phytotoxicity of purified compounds was evaluated, and neoambrosim was active against Agrostis stolonifera at 1 mM, while confertin was active against both, Lactuca sativa and A. stolonifera at 1 mM and 100 µM, respectively. Confertin and salsolol A and B had IC50 values of 261, 275, and 251 µM, respectively, against Lemna pausicotata (duckweed). The antifungal activity was also tested against Colletotrichum fragariae Brooks using a thin layer chromatography bioautography assay. Both confertin and neoambrosin were antifungal at 100 µM, with a higher confertin activity than that of neoambrosin at this concentration.

Identification of antiplasmodial triterpenes from Keetia species using NMR-based metabolic profiling

IntroductionThe increase in multidrug resistance and lack of efficacy in malaria therapy has propelled the urgent discovery of new antiplasmodial drugs, reviving the screening of secondary metabolites from traditional medicine. In plant metabolomics, NMR-based strategies are considered a golden method providing both a holistic view of the chemical profiles and a correlation between the metabolome and bioactivity, becoming a corner stone of drug development from natural products.ObjectiveCreate a multivariate model to identify antiplasmodial metabolites from 1H NMR data of two African medicinal plants, Keetia leucantha and K. venosa.MethodsThe extracts of twigs and leaves of Keetia species were measured by 1H NMR and the spectra were submitted to orthogonal partial least squares (OPLS) for antiplasmodial correlation.ResultsUnsupervised 1H NMR analysis showed that the effect of tissues was higher than species and that triterpenoids signals were more associated to Keetia twigs than leaves. OPLS–DA based on Keetia species correlated triterpene signals to K. leucantha, exhibiting a higher concentration of triterpenoids and phenylpropanoid-conjugated triterpenes than K. venosa. In vitro antiplasmodial correlation by OPLS, validated for all Keetia samples, revealed that phenylpropanoid-conjugated triterpenes were highly correlated to the bioactivity, while the acyclic squalene was found as the major metabolite in low bioactivity samples.ConclusionNMR-based metabolomics combined with supervised multivariate data analysis is a powerful strategy for the identification of bioactive metabolites in plant extracts. Moreover, combination of statistical total correlation spectroscopy with 2D NMR allowed a detailed analysis of different triterpenes, overcoming the challenge posed by their structure similarity and coalescence in the aliphatic region.

Protective effects of Cotoneaster integerrimus on in vitro and ex-vivo models of H2 O2 -induced lactate dehydrogenase activity in HCT116 cell and on lipopolysaccharide-induced inflammation in rat colon.

The present study evaluated the biological potential of methanol and aqueous extracts of the twigs and fruits of Cotoneaster integerrimus Medik. Lethality bioassays performed on Artemia salina showed that aqueous and methanol C. integerrimus extracts were non-toxic in the concentration range (0.1-20mg/ml), with a LC50≥2.5mg/ml, for each single extract. The protective effect of the extracts was assessed in vitro against hydrogen peroxide-induced lactate dehydrogenase (LDH) activity and tumor necrosis factor (TNF)α gene expression in colon cancer HCT116 cell line. All the extracts downregulated (H2 O2 )-induced TNFα gene expression, in HCT116. By contrast, it was observed that the lipopolysaccharide (LPS)-induced increase in colon nitrite, prostaglandin E2 , and 8-iso-PGF2α levels were counteracted mostly by the methanol twig extract. The present study showed protective effects induced by C. integerrimus in vitro and ex vivo, thus supporting potential application in the management of chronic inflammatory diseases. PRACTICAL APPLICATIONS: In the present study, protective effects of C. integerrimus are highlighted using in vitro and ex-vivo models of hydrogen peroxide-induced LDH activity in HCT116 cell and on LPS-induced inflammation in rat colon. Based on our results, this edible and traditionally used species could be considered as a valuable source of natural agents to combat inflammatory diseases, particularly ulcerative colitis. Results amassed herein advocates for further bioprospection of this species that could open new avenues for the development of nutraceuticals and functional foods geared toward the management of chronic inflammatory diseases.