Determination of the Total Phenolics Content and Antioxidant Activity of Extracts from Parts of Plants from the Greek Island of Crete.

Oxidative damages are responsible for many adverse health effects and food deterioration. The use of antioxidant substances is well renowned, and as such, much emphasis is placed on their use. Since synthetic antioxidants exhibit potential adverse effects, plant-derived antioxidants are a preferable solution. Despite the myriads of plants that exist and the fact that numerous studies have been carried out so far, there are many species that have not been examined so far. Many plants under research exist in Greece. Trying to fill this research gap, the total phenolics content and antioxidant activity of seventy methanolic extracts from parts of Greek plants were evaluated. The total phenolics content was measured by the Folin-Ciocalteau assay. Their antioxidant capacity was calculated by the 2,2-Diphenyl-1-picrylhydrazyl (DPPH) scavenging test, the Rancimat method based on conductometric measurements, and the thermoanalytical method DSC (Differential Scanning Calorimetry). The tested samples were obtained from several parts of fifty-seven Greek plant species belonging to twenty-three different families. Both a remarkably high phenolic content (with gallic acid equivalents varying between 311.6 and 735.5 mg/g of extract) and radical scavenging activity (IC50 values ranged from 7.2 to 39.0 µg/mL) were found in the extract of the aerial parts of Cistus species (C. creticus subsp. creticus, C. creticus subsp. eriocephalus, C. monspeliensis, C. parviflorus and C. salviifolius), Cytinus taxa (C. hypocistis subsp. hypocistis, C. hypocistis subsp. orientalis and C. ruber), and Sarcopoterium spinosum. Furthermore, the sample of Cytinus ruber showed the highest protection factor (PF = 1.276) regarding the Rancimat method, which was similar to that of butylated hydroxytoluene (BHT) (PF = 1.320). The results indicated that these plants are rich in antioxidant compounds, potentiating their use either as food additives to enhance the antioxidant properties of food products, or protect them from oxidation, or as sources for the preparation of food supplements with antioxidant properties.

The Effect of Ceratonia siliqua Supplement on Bone Mineral Density in Ovariectomy-induced Osteoporosis in Rats.

AIM: This study aimed to investigate the effect of Ceratonia siliqua on bone mineral density (BMD) as a non-pharmaceutical alternative treatment for postmenopausal osteoporosis. MATERIALS AND METHODS: Thirty mature female Wistar rats were randomly separated into three groups of 10: Control, ovariectomized (OVX), and ovariectomized-plus-C. siliqua (OVX+CS). Total and proximal BMD were measured by dual-energy X-ray absorptiometry (DEXA) in all groups before ovariectomy, and at 3 and 6 months postoperatively. At the end of the study, the femurs were subjected to a three-point bending test. RESULTS: DEXA revealed no statistically significant difference in absolute values or percentage changes for total tibial BMD between OVX+CS and OVX groups throughout the study. In the proximal tibia, both absolute values and BMD percentage changes from baseline were higher in the OVX+CS group compared to the OVX group after 3 and 6 months of C. siliqua administration. Three-point bending test revealed a significantly higher thickness index in the OVX+CS group compared to the OVX group and a higher cross-sectional area index compared to the control group. CONCLUSION: Long-term administration of C. siliqua may be considered a non-pharmaceutical alternative treatment for postmenopausal osteoporosis. Further research is required to properly investigate the effects, and suitable treatment dose and schedule.

A GC-MS and LC-HRMS perspective on the chemotaxonomic investigation of the natural hybrid Origanum × lirium and its parents, O. vulgare subsp. hirtum and O. scabrum.

INTRODUCTION: The genus Origanum L. (Lamiaceae) is widespread in the Mediterranean region. However, approximately 75% of the species are only encountered in the eastern part. Out of these, a total of nine species (11 taxa) and three natural hybrids occur in Greece. Nevertheless, so far, there is no consensus regarding their precise botanical classification in the literature. In fact, the taxon Origanum × lirium has been proposed both as a separate species as well as natural hybrid between Origanum vulgare subsp. hirtum and Origanum scabrum. OBJECTIVES: In this scope, the aim of the current study is to shed light on the matter through the investigation of the chemical composition of both the essential oils and the polar extracts of the mentioned taxa, collected from different geographical regions of Greece. RESULTS: As it was demonstrated by both gas chromatography-mass spectrometry (GC-MS) and liquid chromatography-high-resolution mass spectrometry (LC-HRMS) data, and highlighted by our comparative analysis, it can be stipulated that Origanum × lirium shares its chemotype to a large extent with its parent species concerning both volatile and polar constituents. Additionally, geographical origin conditions stood out as a key factor influencing their chemical composition. CONCLUSION: Altogether, the present work provides useful information on the chemical composition of the taxa under investigation, while our findings support the opinion that Origanum × lirium should be considered not as a separate species, but rather as a hybrid on the way to becoming a species.

Novel Evidence-Based Combination of Plant Extracts with Multitarget Mechanisms of Action for the Elimination of Hot Flashes during Menopause.

Hot flashes are considered the most bothersome complaint during menopause. Although hormone therapy is an effective option to relieve hot flashes, it has been associated with significant side effects. The aim of our study is to suggest a novel combination of different plant extracts with distinct mechanisms of action against hot flashes. We selected the rhizome of Glycyrrhiza glabra L. (Fabaceae), the rhizome of Actaea racemosa L. (Ranunculaceae), the aerial parts of Hypericum perforatum L. (Hypericaceae) to produce extracts rich in bioactive phytochemicals and the seed oil of Oenothera biennis L. (Onagraceae). We investigated their estrogenic and antioxidant potential and their inhibitory effect against prostaglandin D2 receptor 1 (DP1) as a novel mechanistic pathway for vasodilation in hot flashes, alone or in combination. The phytochemical footprint of the extracts was analyzed using HPLC-PDA and UPLC-HRMS. We observed that the tested extracts possess different mechanisms of action. A. racemosa exerts a beneficial activation of the estrogen receptor, H. perforatum possesses the highest antioxidant capacity and the seed oil of O. biennis inhibits the DP1 receptor. The triple combination in the optimal doses pertains to efficacy against all three mechanisms of action, serves as a multitarget plant-based therapy and could serve as a novel strategy for the alleviation of hot flashes in postmenopausal women.

Development and physicochemical characterization of nanoliposomes with incorporated oleocanthal, oleacein, oleuropein and hydroxytyrosol.

Oleocanthal, oleacein, oleuropein and hydroxytyrosol comprise characteristic polyphenols of olive with high biological value. However, stability problems hinder their further investigation. Thus, in the present study they were incorporated in nanoliposomes by thin film hydration method. The particles sizes, PDI, zeta-potential and physicochemical stabilities of nanoliposomes were evaluated by light scattering methods while FTIR, XRD, TGA and DSC methods were carried out for further physicochemical characterization. Their micromorphology was illustrated by negative-staining TEM and Cryo-TEM, revealing well-dispersed round-shaped vesicles. According to in vitro release studies, oleocanthal and oleacein were rapidly released in a higher percentage than oleuropein and hydroxytyrosol and compatible with the Ritger-Peppas model release mechanism while only oleuropein liposomes were governed by anomalous diffusion of non-Fickian diffusion. Antioxidant assays showed that nanoliposomes presented comparable activity with pure compounds enabling them as suitable carriers for the delivery of olive active biophenols in the human organism.

Retrieval of High Added Value Natural Bioactive Coumarins from Mandarin Juice-Making Industrial Byproduct.

Cold pressed essential oil (CPEO) of mandarin (Citrus reticulata Blanco), a by-product of the juice-making industrial process known to contain large amounts of polymethoxyflavones, was exploited for its content in high added value natural coumarins. The study herein afforded a method referring to the evaporation of CPEO volatile fraction under mild conditions (reduced pressure and temperature below 35 °C) as azeotrope with isopropanol. This allowed the isolation of high added value coumarins from the non-volatile fragment using preparative High Performance Liquid Chromatography (HPLC). Pilot-scale application of this procedure afforded for each kg of CPEO processed the following natural bioactive coumarins in chemically pure forms: heraclenol (38-55 mg), 8-gerayloxypsoralen (35-51 mg), auraptene (22-33 mg), and bergamottin (14-19 mg). The structures of coumarins were verified by Nuclear Magnetic Resonance (NMR) spectroscopy and HPLC co-injection with authentic standards. Thus, the low market value mandarin CPEO with current value of 17 to 22 EUR/kg can be valorized through the production of four highly bioactive natural compounds worth 3479 to 5057 EUR/kg, indicating the great potentials of this methodology in the terms of the circular economy.

Chios Mastic Gum Consumption Has a Protective Effect on Ovariectomy-Induced Bone Loss in Rats.

The purpose of this study was to examine the potential effect of Chios Mastic Gum (CMG) consumption on bone mineral density (BMD) and strength of ovariectomized rats. CMG is a known resin used from ancient times for its beneficial biological properties. Thirty mature female Wistar rats were randomized into three equal groups: sham-operated (control), ovariectomized (OVX), and ovariectomized and administered CMG per os (OVX+CMG). BMD of the total tibia, proximal tibia, and the 6th lumbar vertebra were measured at baseline and at 3 and 6 months post ovariectomy. Bone strength was assessed with three-point-bending (3pb) of the right femur. At 3 and 6 months, BMD values of the OVX+CMG group were significantly higher for the anatomical cites evaluated than those of the OVX group. Femoral thickness assessed via 3pb had intermediate values in the treated group compared to the other groups. Cytology of vaginal smears and uterine weight of the OVX+CMG group were consistent with estrogen depletion. Gastrocnemius muscle and intraperitoneal fat ratios to body weight (BW) of the OVX+CMG group did not significantly differ from the control group. Daily consumption CMG had a protective effect on BMD of the total and proximal tibia and the 6th lumbar vertebra of the rats, without causing undesirable effects on the vaginal epithelium and uterus. The 3pb results also demonstrated a favorable effect on the thickness of rat femurs. In addition, CMG was beneficial for both the muscular system and the intraperitoneal fat/BW ratio of the rats.

Exploitation of Vitis vinifera, Foeniculum vulgare, Cannabis sativa and Punica granatum By-Product Seeds as Dermo-Cosmetic Agents.

In the current study, by-product seed pastes (VSPs) from Vitis vinifera, Foeniculum vulgare, Cannabis sativa and Punica granatum, generated during the oil production process, were investigated for their potential exploitation as dermo-cosmetic agent. The extraction pipeline of all the raw materials was developed with emphasis on green methodologies and employed on laboratory scale based on industry-adopted techniques. Two different protocols were applied, Supercritical Fluid Extraction (SFE) and Ultrasound Assisted Extraction (UAE); the by-product pastes were defatted with supercritical CO2 and n-Hexane, respectively. Then, two SFE extracts (CO2 with 10% and 20% of ethanol as co-solvent) and two UAE extracts (with ethanol and ethanol/water 1:1 v/v) were obtained from each raw material. The providing yield range was between 2.6 to 76.3 mg/g raw material. The extracts were analyzed with High-Performance Liquid Chromatography coupled with Diode Array Detector (HPLC-DAD) and Liquid Chromatography coupled with High-Resolution Mass Spectrometer (LC-HRMS), and the major compounds, were identified. All the extracts were evaluated for their antioxidant and inhibition activity against collagenase, elastase and tyrosinase enzymes. Grapevine by-product extracts found rich in proanthocyanidins and presented the higher inhibition activity. A holistic green experimental methodology is proposed for the obtainment of extracts from significant medicinal plants by-products that provides us with promising results concerning dermo-cosmetic properties, especially for grape seeds extracts.

Isoflavonoid Profiling and Estrogen-Like Activity of Four Genista Species from the Greek Flora.

As part of our ongoing research on phytoestrogens, we investigated the phytochemical profile and estrogen-like activities of eight extracts from the aerial parts of four Genista species of Greek flora using estrogen-responsive cell lines. Ethyl acetate and methanolic extracts of G. acanthoclada, G. depressa,G. hassertiana, and G. millii were obtained with accelerated solvent extraction and their phytochemical profiles were compared using ultra-high-performance liquid chromatography-high-resolution mass spectrometry (uHPLC-HRMS). Fourteen isoflavonoids, previously isolated from G. halacsyi, were used as reference standards for their identification in the extracts. Thirteen isoflavonoids were detected in both extracts of G. acanthoclada and G. hassertiana, while fewer and far fewer were detected in G. millii and G. depressa, respectively. The ethyl acetate extracts of G. hassertiana and G. acanthoclada displayed 2.45- and 1.79-fold higher, respectively, estrogen-like agonist activity in Ishikawa cells compared to MCF-7 cells at pharmacologically relevant concentrations. Both these extracts, but not that of G. depressa, contained mono- and di-O-ß-d-glucosides of genistein as well as the aglycone, all three of which are known to display full estrogen-like activity at lower-than-micromolar concentrations. The possibility of using preparations rich in G. hassertiana and/or G. acanthoclada extracts as a potentially safer substitute for low-dose vaginal estrogen for menopausal symptoms is discussed.

Phytochemical Profile and Biological Activity of Endemic Sideritis sipylea Boiss. in North Aegean Greek Islands.

Sideritis sipylea Boiss. is an endemic plant of the Mediterranean basin that is distributed in the Greek islands of the North Aegean Sea, i.e., Lesvos, Chios, Samos, and Ikaria, and in the West and Middle peninsula of Turkey. It is considered an endangered species because of its uncontrolled collection from its original habitat. Although the antioxidant, anti-inflammatory and antimicrobial properties have been previously reported, the total chemical profile has not yet been explored. In this context, the chemical profiles of the water/methanol (HA), methanol (ME), and ethyl acetate (EtOAc) extracts were analyzed using ultra-performance liquid chromatography coupled with high-resolution mass spectrometry (UPLC-HRMS). In parallel, analysis by gas chromatography-mass spectrometry (GC-MS) was employed for the dichloromethane extract (DCM) as well as for the essential oil (EO) and the extract obtained by supercritical fluid extraction (SFE). Furthermore, the total phenolic content (TPC) along with the in vitro tyrosinase and elastase enzyme inhibitory activity of different extracts was evaluated, towards the discovery of new active agents for cosmetic formulations. These activities are in accordance with its well-known antioxidant and anti-inflammatory properties, confirming the importance of ethnopharmacological references for S. sipylea in Greece and Turkey.

Phytochemical analysis of olive flowers' hydroalcoholic extract and in vitro evaluation of tyrosinase, elastase and collagenase inhibition activity.

Olea europaea L. is historically one of the most important trees of the Mediterranean countries. Increasing scientific interest regarding its fruits, leaves and olive oil has led to the elucidation of several phytochemical and biological characteristics. However, the phytochemical and biological studies regarding olive flowers remain limited. The aim of the present study was the phytochemical characterization of olive flowers' hydroalcoholic extract from Greek variety Lianolia, the effective isolation of the major secondary metabolites and evaluation of their inhibition activity against tyrosinase, elastase and collagenase. UPLC-HRMS/MS analysis was used to investigate the chemical composition of hydroalcoholic extract resulting in the identification of sixty-three secondary metabolites witch mainly belong to phenilethanoids, triterpenoids, flavonoids and secoiridoids. The orthogonial combination of Centrifugal Partition Chromatography and preparative HPLC in the same purification process led to the isolation of nine major compounds of the extract including two triterpenic acids, two flavonoid glycosides and five secoiridoid derivatives. From them, oleofloside A and oleofloside B are new natural products. Although, the hydroalcoholic extract and isolated secoiridoids exhibited weak or no inhibition activity towards tyrosinase and elastase, they exhibit remarkable anti-collagenase activity with 2΄-ethoxyoleuropein being the most active compound.

Traditional uses, phytochemistry and pharmacology of Chios mastic gum (Pistacia lentiscus var. Chia, Anacardiaceae): A review.

ETHNOPHARMACOLOGICAL RELEVANCE: Chios mastic gum constitutes a unique Greek product, produced exclusively in the southern part of the island of Chios. References about its use from local populations for the treatment of gastrointestinal disorders or as a cosmetic agent can even be encountered in ancient texts of Galen, Theophrastus and Dioscorides. Nowadays, this versatile resin has been rediscovered, not only as a traditional remedy and aromatic agent, but as a potent phytotherapeutic product with various biological properties. AIM OF THE STUDY: The aim of this study is to quote the summation of the ethnopharmacology, phytochemical profile and pharmacological properties of the resin of Pistacia lentiscus var. Chia and thus provide the scientific community with a summary of the research conducted so far. Furthermore, perspectives and uses are being discussed and studied so as to broaden the field of its applications. MATERIALS AND METHODS: A comprehensive review of the literature on Pistacia lentiscus var. Chia was performed using as resources scientific databases such as Scopus, Sciencedirect, Pubmed and Web of science, studies and traditional books provided by the Chios Mastiha Growers Association as well as PhD and Master' s theses. RESULTS: Chios mastic gum has been used as a traditional medicine over the last 2500 years. More than 120 chemical compounds have been identified in the resin and the major components are a natural polymer, acidic and neutral triterpenes and volatile secondary metabolites. Several plant extracts and compounds have been studied for their antibacterial, anti-inflammatory, antioxidant, anti-ulcer, anti-diabetic, cardioprotective and anti-cancer properties in vitro and in vivo. Clinical interventions and trials have also showed the therapeutic potential of Chios mastic gum. In 2015 Pistacia lentiscus L., resin (mastic) was recognized as a herbal medicinal product with traditional use by the European Medicines Agency (EMA) with two therapeutic indications (mild dyspeptic disorders & skin inflammation/healing of minor wounds). Over the last years, Chios mastic gum is widely involved in medicinal products, food supplements and cosmetics and has become object of study, also in the field of Pharmacotechnology. CONCLUSIONS: Chios mastic's beneficial properties have been demonstrated in the treatment of gastrointestinal disorders, wound healing, skin inflammations, plasma lipid and blood sugar reduction and oral care. These properties are attributed to triterpenes and volatile compounds. However, because of the resin's chemical complexity and the lack of commercial standards for its main compounds, there is a notable gap in literature concerning the biological evaluation of CMG's isolated components. Therefore, future research should focus on the development of efficient extraction, isolation and analysis techniques in order to unravel CMG's full pharmacological potential.

Recovery of Sesamin, Sesamolin, and Minor Lignans From Sesame Oil Using Solid Support-Free Liquid-Liquid Extraction and Chromatography Techniques and Evaluation of Their Enzymatic Inhibition Properties.

In this study, an integrated process for the recovery of sesamin and sesamolin, two high added-value lignans of sesame oil (SO) was developed, using synchronous extraction and chromatography techniques. The extraction of SO phenolic content was studied using two different extraction techniques: Annular centrifugal extraction (ACE) and centrifugal partition extraction (CPE). The derived data of each experiment were compared in terms of revealing the yields, time, and solvents consumption showing that CPE is the most effective technique, concerning the solvent consumption. The isolation of lignans was achieved using centrifugal partition chromatography (CPC) both on semi-preparative and preparative scale. The biphasic system used for this purpose consisted of the following solvents: n-Hex/EtOAc/EtOH/H2O in proportion 2:3:3:2 (v/v/v/v) and direct recovery of the two major lignans sesamin and sesamolin was achieved. In parallel the CPC analysis resulted in the isolation of four minor lignans of sesame oil, i.e., samin, sesamol, sesaminol, and episesaminol. Structure elucidation of isolated lignans was based on HRMS/MS and NMR experiments. High-performance liquid chromatography (HPLC) was employed for quantitative analysis of the obtained extracts to determine the purity of the isolated compounds as well. The results of this study demonstrated that sesamin and sesamolin were recovered in purity higher than 95%, verifying the effectiveness of the purposed separation methodology. Finally, due to the general application of sesame oil in cosmetic industry, all the pure compounds were evaluated for their tyrosinase, elastase, collagenase, and hyaluronidase inhibition activity.

Protective effect of Glycyrrhiza glabra roots extract on bone mineral density of ovariectomized rats.

OBJECTIVE: The aim of this study was to evaluate the potential effect of the methanolic extract of plant Glycyrrhiza glabra roots on bone mineral density and femoral bone strength of ovariectomized rats. METHODS: Thirty 10-month-old Wistar rats were randomly separated into three groups of ten, Control, Ovariectomy and Ovariectomy-plus-Glycyrrhiza in their drinking water. Total and proximal tibial bone mineral density was measured in all groups before ovariectomy (baseline) and after 3 and 6 months post ovariectomy. Three-point-bending of the femurs and uterine weight and histology were examined at the end of the study. RESULTS: No significant difference was noted in bone density percentage change of total tibia from baseline to 3 months between Control and Ovariectomy-plus-Glycyrrhiza groups (+5.31% ± 4.75 and +3.30% ± 6.31 respectively, P = non significant), and of proximal tibia accordingly (+5.58% ± 6.92 and +2.61% ± 13.62, P = non significant) demonstrating a strong osteoprotective effect. There was notable difference in percentage change of total tibia from baseline to 6 months between groups Ovariectomy and Ovariectomy-plus-Glycyrrhiza (-13.03% ± 5.11 and -0.84% ± 7.63 respectively, P < 0.005), and of proximal tibia accordingly (-27.9% ± 3.69 and -0.81% ± 14.85 respectively, P < 0.001), confirming the protective effect of Glycyrrhiza glabra extract in preserving bone density of the Ovariectomy-plus-Glycyrrhiza group. Three-point-bending did not reveal any statistically significant difference between Ovariectomy and Ovariectomy-plus-Glycyrrhiza groups. Uterine weights of the Ovariectomy-plus-Glycyrrhiza group ranged between the other two groups with no statistically significant difference to each. CONCLUSIONS: Glycyrrhiza glabra root extract notably protected tibial bone mineral density loss in Ovariectomy-plus-Glycyrrhiza rats in comparison with ovariectomized rats, but did not improve biomechanical strength.

Quantification of bioactive lignans in sesame seeds using HPTLC densitometry: Comparative evaluation by HPLC-PDA.

Sesamin and sesamolin constitute the main bioactive secondary metabolites of sesame seeds (Sesamum indicum L., Pedaliaceae). In the present work, a rapid HPTLC-based methodology was developed in compliance with the requirements of the European Pharmacopoeia for the quantification of these two lignans in sesame seeds. A comparative study was simultaneously performed with HPLC-PDA for assessing the sesamin and sesamolin content of diverse samples. Both methods were validated and the results were subsequently subjected to statistical analysis in order to compare their performance as well as to investigate possible correlations. The methods were shown to be adequately correlated in terms of performance, as revealed by Pearson's rank correlation coefficients (>0.99 for sesamin and >0.98 for sesamolin) and Bland-Altman analysis (relative method bias 0.06-0.21, SD of bias 0.05-0.07). HPTLC densitometry could thereby serve as a valid and reliable tool for the rapid determination of the major lignans in sesame seed samples.

Biological evaluation of isoflavonoids from Genista halacsyi using estrogen-target cells: Activities of glucosides compared to aglycones.

The purpose of this study was to evaluate the response of estrogen target cells to a series of isoflavone glucosides and aglycones from Genista halacsyi Heldr. The methanolic extract of aerial parts of this plant was processed using fast centrifugal partition chromatography, resulting in isolation of four archetypal isoflavones (genistein, daidzein, isoprunetin, 8-C-ß-D-glucopyranosyl-genistein) and ten derivatives thereof. 7-O-ß-D-glucopyranosyl-genistein and 7,4΄-di-O-ß-D-glucopyranosyl-genistein were among the most abundant constituents of the isolate. All fourteen, except genistein, displayed low binding affinity for estrogen receptors (ER). Models of binding to ERα could account for the low binding affinity of monoglucosides. Genistein and its glucosides displayed full efficacy in inducing alkaline phosphatase (AlkP) in Ishikawa cells, proliferation of MCF-7 cells and ER-dependent gene expression in reporter cells at low concentrations (around 0.3 µM). ICI182,780 fully antagonized these effects. The AlkP-inducing efficacy of the fourteen isoflavonoids was more strongly correlated with their transcriptional efficacy through ERα. O-monoglucosides displayed higher area under the dose-response curve (AUC) of AlkP response relative to the AUC of ERα-transcriptional response compared to the respective aglycones. In addition, 7-O-ß-D-glucopyranosyl-genistein and 7,4΄-di-O-ß-D-glucopyranosyl-genistein displayed estradiol-like efficacy in promoting differentiation of MC3T3-E1 cells to osteoblasts, while genistein was not convincingly effective in this respect. Moreover, 7,4΄-di-O-ß-D-glucopyranosyl-genistein suppressed lipopolysaccharide-induced tumor necrosis factor mRNA expression in RAW 264.7 cells, while 7-O-ß-D-glucopyranosyl-genistein was not convincingly effective and genistein was ineffective. However, genistein and its O-glucosides were ineffective in inhibiting differentiation of RAW 264.7 cells to osteoclasts and in protecting glutamate-challenged HT22 hippocampal neurons from oxidative stress-induced cell death. These findings suggest that 7-O-ß-D-glucopyranosyl-genistein and 7,4΄-di-O-ß-D-glucopyranosyl-genistein display higher estrogen-like and/or anti-inflammatory activity compared to the aglycone. The possibility of using preparations rich in O-ß-D-glucopyranosides of genistein to substitute for low-dose estrogen in formulations for menopausal symptoms is discussed.

Extracts from the Mediterranean Food Plants Carthamus lanatus, Cichorium intybus, and Cichorium spinosum Enhanced GSH Levels and Increased Nrf2 Expression in Human Endothelial Cells.

The Mediterranean diet is considered to prevent several diseases. In the present study, the antioxidant properties of six extracts from Mediterranean plant foods were assessed. The extracts' chemical composition analysis showed that the total polyphenolic content ranged from 56 to 408 GAE mg/g dw of extract. The major polyphenols identified in the extracts were quercetin, luteolin, caftaric acid, caffeoylquinic acid isomers, and cichoric acid. The extracts showed in vitro high scavenging potency against ABTS•+ and O2 •- radicals and reducing power activity. Also, the extracts inhibited peroxyl radical-induced cleavage of DNA plasmids. The three most potent extracts, Cichorium intybus, Carthamus lanatus, and Cichorium spinosum, inhibited OH•-induced mutations in Salmonella typhimurium TA102 cells. Moreover, C. intybus, C. lanatus, and C. spinosum extracts increased the antioxidant molecule glutathione (GSH) by 33.4, 21.5, and 10.5% at 50 µg/ml, respectively, in human endothelial EA.hy926 cells. C. intybus extract was also shown to induce in endothelial cells the transcriptional expression of Nrf2 (the major transcription factor of antioxidant genes), as well as of antioxidant genes GCLC, GSR, NQO1, and HMOX1. In conclusion, the results suggested that extracts from edible plants may prevent diseases associated especially with endothelium damage.

Phytochemical Composition of the Decoctions of Greek Edible Greens (Chórta) and Evaluation of Antioxidant and Cytotoxic Properties.

Wild or semi-wild edible greens (chórta) are an integral part of the traditional Greek Mediterranean diet due to their nutritional value, containing various phytonutrients beneficial to human health. Water-based decoctions of chórta are widely consumed in Greek alternative medicine as health promoting agents. This study examined the chemical profile of the decoctions of eight edible plants, Cichorium intybus, C. endivia, C. spinosum, Crepis sancta, Sonchus asper, Carthamus lanatus, Centaurea raphanina, and Amaranthus blitum, by UPLC-ESI-HRMS and HRMS/MS analysis, to determine possibly bioactive constituents. The profiles of the plants from the Asteraceae family are dominated by the presence of phenolic acids and flavonoid derivatives, whereas the A. blitum decoction is rich in triterpene saponins. Interestingly, the Centaurea raphanina decoction was found to be extremely rich in flavanones, particularly in the aglycone pinocembrin. Further phytochemical investigation and fractionation of this extract resulted in the isolation and identification of five compounds: phlorin (1), syringin (2), pinocembrin (3), pinocembroside (4), and pinocembrin-7-O-neohesperidoside (5). The extracts were also tested for their antioxidant and differential cytotoxic activity against tumor cells. C. raphanina was found to be differentially toxic against metastatic tumor cells. In conclusion, we found that Greek edible greens are a rich source of bioactive secondary metabolites and their consumption could contribute to the maintenance of overall health.

Phytotoxic triterpene saponins from Bellis longifolia, an endemic plant of Crete.

In a study of 62 plant species of the Cretan flora for their phytotoxic activity, plants were extracted successively with CH2Cl2, MeOH and H2O. Phytotoxicity evaluation of the 240 extracts was performed against Lactuca sativa L. and Agrostis stolonifera L.. The MeOH extract of Bellis longifolia was the most phytotoxic. Bioassay-guided fractionation revealed that a fraction consisting mainly of saponins was the most effective. Separation of the saponins was performed using initially a step-gradient Centrifugal Partition Chromatography (CPC). Investigation of the active fraction led to the isolation and structure elucidation of three previously undescribed triterpene saponins, 3-O-ß-D-fucopyranosyl polygalacic acid, 28-O-α-L-rhamnopyranosyl-(1 â†’ 2)-ß-D-fucopyranosyl polygalacic acid and 3-O-ß-D-fucopyranosyl-2α,3ß,23-trihydroxyolean-12-en-28-oic acid, which were present as the main phytotoxic compounds of the methanol extract. Two triterpenes, polygalacic acid and bellisonic acid and four kaempferol glucosides, as well as chlorogenic acid were also isolated. 3-O-ß-D-fucopyranosyl polygalacic acid and 3-O-ß-D-fucopyranosyl-2α,3ß,23-trihydroxyolean-12-en-28-oic acid had phytotoxic activity similar to some commercial herbicides (IC50 values of ca. 25 µM) against duckweed (Lemna paucicostata).