Phytochemical screening and evaluation of antioxidant and anti-inflammatory potential of secondary metabolites of Plantago L. species

Karakterizacija metanolnih ekstrakata jedanaest vrsta samoniklih bokvica (rod Plantago L.) obuhvatala je fitohemijski skrining i ispitivanje antioksidantne i antiinflamatorne aktivnosti. Primenom LC-MS/MS tehnike odreĊen je sadržaj odabranih sekundarnih biomolekula. Antioksidantna aktivnosti ekstrakata (sposobnost neutralizacije slobodnih radikala, redukcioni potencijal i inhibicija lipidne peroksidacije) ispitana je primenom spektrofotometrijskih metoda. U cilju odreĊivanja antiinflamatornog potencijala, razvijena je in vitro metoda za praćenje aktivnosti trombocitne ciklooksigenaze-1 i 12-lipoksigenaze. Svi ispitani ekstrakti pokazali su znaĉajnu biološku aktivnost.Characterization of methanol extracts of eleven Plantago L. species included phytochemical screening and evaluation of antioxidant and anti-inflammatory activity. The content of several secondary metabolites was determined by LC-MS/MS technique. Antioxidant activity of extracts (radical scavenger capacity, reduction potential and inhibition of lipid peroxidation) was examined by spectrophotometric methods. With the intention to evaluate anti-inflammatory activity, an in vitro method was developed to measure activity of platelet cyclooxygenase-1 and 12-lipoxygenase. All examined extracts showed noticeable biological activity

Evaluation of sambucus Nigra L. Biopotential as an unused natural resource

An unbreakable relationship between plants, nutrition, and health has directed researchers to deeply investigate and characterize the biopotential and medicinal properties of traditional foods. The aim of this study is to analyze and compare the phytochemical composition and biological potential of plant extracts with the idea of defining the most potent extracts as a natural source of bioactive molecules and their application in different industries. We evaluated unused plant species Sambucus nigra L. for investigation of bioactivities as potential natural products. Extracts of fresh elderberry fruits were obtained by modern (microwave‐assisted extraction (MAE), ultrasound‐assisted extraction (UAE)) and traditional (maceration (MAC)) extraction techniques, using 50% ethanol (50% EtOH) and water (H2O) of different polarities. In analyzed extracts, rutin and chlorogenic acid were dominant compounds in both 50% EtOH and H2O extracts, while ursolic acid was identified in 50% EtOH extracts as a terpenic compound with notable concentration. Elderberry extracts were evaluated regarding antioxidant, neuroprotective, antityrosinase, and antidiabetic abilities: MAE extracts had the best overall activity, and in general, 50% EtOH extracts were more potent than water extracts. The correlation of the dominant compound—rutin with all biological activities, indicates the importance of its presence in elderberries. S. nigra fruits showed excellent biopotential and opened possibilities of creating new food products or remedies, which are not present on the market because elderberry extracts are an exceptional source of rutin, chlorogenic acid, and ursolic aci

Hemijski sastav, antiinflamatorni efekat i antitumorska aktivnost ploda štavelja (Rumex crispus L., Polygonaceae)

Curly dock (Rumex crispus L.) is a perennial herbaceous plant that is traditionally used in the treatment of gastrointestinal ailments, infections and skin diseases. The aim of this study was to examine the chemical composition, ex vivo anti-inflammatory effect and in vivo antiproliferative activity of water extract of curly dock fruit. The polyphenolic profile was analyzed by LC-DAD-ESI-MS technique. The effect on the production of arachidonic acid metabolites was examined in human platelets. Antitumor activity of orally administered extract (concentration: 5% w/v; doses: 1, 2 and 5 mL/kg of body weight/day; treatment length: 7 days) to Ehrlich ascites tumor and hepatocellular carcinoma was assessed in an animal experiment. Ascites volume, viable cell percentage and antioxidant enzyme levels were determined. The presence of phenolic acids (gallic and protocatechuic acids), proanthocyanidins (monomers, dimers and trimers), flavonoid glycosides and anthraquinone emodin was revealed in the water extract of R. crispus fruit. The content of the quantitatively dominant compound miquelianin was 2.4%. The investigated preparation concentration-dependently inhibited the synthesis of 12(S)-hydroxy-(5Z,8E,10E)- heptadecatrienoic acid (IC50 = 4.96 mg/mL) and 12(S)-hydroxy-(5Z,8Z,10E,14Z)- eicosatetraenoic acid (IC 50 = 2.06 mg/mL). The antitumor effect in animals was dose- dependent and manifested as suppression of tumor growth and induction of cell death of malignantly transformed cells. Values of biochemical parameters suggested that oxidative stress was induced in cancer cells, and it can be assumed that this mechanism was at least partly responsible for the activity. Water extract of R. crispus fruit has significant pharmacological potential that justifies further research.Štavelj (Rumex crispus L.) je višegodišnja zeljasta biljka koja se tradicionalno koristi u tretmanu gastrointestinalnih tegoba, infekcija i kožnih oboljenja. Cilj ove studije je bio da se ispita hemijski sastav, ex vivo antiinflamatorni efekat i in vivo antiproliferativna aktivnost vodenog ekstrakta ploda štavelja. Polifenolni profil je analiziran LC‐DAD‐ESI‐MS tehnikom. Uticaj na produkciju metabolita arahidonske kiseline je ispitan u humanim trombocitima. Antitumorska aktivnost oralno primenjenog ekstrakta (koncentracija: 5% m/V; doze: 1, 2 i 5 mL/kg telesne težine/dan; dužina tretmana: 7 dana) prema Ehrlich-ovom ascitnom tumoru i hepatocelularnom karcinomu procenjena je u eksperimentu na životinjama. Određeni su zapremina ascitesa, procenat vijabilnih ćelija i nivoi antioksidantnih enzima. U vodenom ekstraktu ploda R. crispus je utvrđeno prisustvo fenolnih kiselina (galna i protokatehinska kiselina), proantocijanidina (monomeri, dimeri i trimeri), flavonoidnih heterozida i antrahinona emodina. Sadržaj kvantitativno dominantnog jedinjenja mikvelijanina je iznosio 2,4%. Ispitivani preparat je koncentraciono-zavisno inhibirao sintezu 12(S)-hidroksi- (5Z,8E,10E)-heptadekatrienske kiseline (IC 50 = 4,96 mg/mL) i 12(S)-hidroksi- (5Z,8Z,10E,14Z)-eikozatetraenske kiseline (IC50 = 2,06 mg/mL). Antitumorski efekat u životinja je bio dozno-zavisan i ispoljio se kao suprimiranje rasta tumora i indukcija ćelijske smrti maligno transformisanih ćelija. Vrednosti biohemijskih parametara su sugerisale da je u ćelijama karcinoma došlo do indukovanja oksidativnog stresa, te se može pretpostaviti da je ovaj mehanizam bio barem delom zaslužan za aktivnost. Vodeni ekstrakt ploda R. crispus poseduje značajan farmakološki potencijal koji opravdava dalje istraživanje.VIII Kongres farmaceuta Srbije sa međunarodnim učešćem, 12-15.10.2022. Beogra

Chemical composition of Origanum dictamnus and Origanum vulgare ssp. hirtum from Greece

Most of the Origanum species are locally distributed within the Mediterranean region where they grow in the mountainous areas on the islands. Due to this, the rate of endemism is high, as in case of dittany of Crete (O. dictamnus). O. vulgare possesses the largest distribution area and can be found throughout the Mediterranean region, however, the yield and quality of the essential oil is controlled genetically and strongly affected by the environmental influences. Origanum essential oils predominantly containing carvacrol, are generally of superior quality and highly valuable raw material for food as well as in pharmaceutical industry. Essential oil of O. dictimus contains 70.8% of carvacrol, while O. vulgare ssp. hirtum essential oil contains 78.5%. This study indicates the high quality of investigated Origanum species from Greece, and indicates it to be highly valuable raw material for food and in pharmaceutical industry

Phenolic profile and anti-inflammatory activity of three Veronica species

Aerial parts of some Veronica species are used as traditional medicine for treatment of various inflammatory conditions, including rheumatism. In the present study, phenolic content and anti-inflammatory activity of three Veronica species (Plantaginaceae), Veronica jacquinii Baumg., Veronica teucrium L. and Veronica urticifolia Jacq was studied. The identification and quantification of 30 phenolic compounds in aqueous-acetone extracts were performed using LC-MS/MS technique, and the main components were baicalin, hyperoside, isoquercetine, chlorogenic acid and quinic acid. Genistein and baicalein were detected for the first time in Plantaginaceae family and Veronica genus, respectively. The anti-inflammatory potential of tested extracts was determined using calcium ionophore-stimulated human platelets as a source of cyclooxygenase-1 (COX-1) and 12-lipoxygenase (12-LOX) enzymes, and highly sensitive and specific LC-MS/MS technique was performed for detection of the main arachidonic acid metabolites formed by them. V. urticifolia extract exerted the strongest COX-1 inhibition (IC50 lt 0.4 mg/mL), while V. jacquinii extract exhibited the highest ability to inhibit 12-LOX activity (IC50 = 1.072 mg/mL). The results obtained in this study may be used to promote better use of the genus Veronica as anti-inflammatory agents

The effects of trifluoromethylated derivatives on prostaglandin E2 and thromboxane A2 production in human leukemic U937 macrophages

Background: A convenient approach to modulation of the inflammation has an influence on the production of inflammatory mediators – icosanoids, generated in arachidonic acid (AA) metabolism. The common therapeutic activity of non-steroidal anti-inflammatory drugs (NSAID), such as aspirin, includes inhibition of two crucial enzymes of AA metabolism-cyclooxygenase-1 and-2 (COX-1/2), with certain risk for gastrointestinal and renal intolerance. Ever since the enrolment of COX-2, particularly overabundance of its main products prostaglandin E2 (PGE2 ) and thromboxane A2 (TXA2 ) in numerous pathological processes was recognized, it became a significant therapeutic target. Objective: The aim of this study was to examine the effects of synthesized organo-fluorine compounds on PGE2 and TXA2 production in the inflammation process. Methods: Trifluoromethyl compounds were synthesized from N-benzyl trifluoromethyl aldimine, commercially available 2-methyl or 2-phenyl α-bromo esters (β-lactams trans-1 and trans-2 and trifluoromethyl β-amino ester, respectively) and methyl 2-isocyanoacetate (2-imidazoline trans-4). The reactions proceeded with high geometric selectivity, furnishing the desired products in good yields. The influence of newly synthesized compounds on PGE2 and TXA2 production in human leukemic U937 macrophages on both enzyme activity and gene expression levels was observed. Results: Among the tested trifluoromethyl compounds, methyl trans-1-benzyl-5-(trifluoromethyl)-4,5-dihydro-1H-imidazole-4-carboxylate (trans-4) can be distinguished as the most powerful anti-inflammatory agent, probably due to its trifluoromethyl-imidazoline moiety. Conclusion: Some further structural modifications in tested compounds and particularly in the synthesis of different trifluoromethyl imidazolines could contribute to the development of new COX-2 inhibitors and potent anti-inflammatory agents. © 2020 Bentham Science Publishers