A New Glucosyl Flavone with Inhibitory Activity of Cancer Cell Viability and Other Bioactive Constituents from the Traditional Kurdish Plant Plantago loeflingii L.

A new glucosyl flavone, 5,7,2',5'-tetrahydroxyflavone 7-O-ß-d-glucopyranoside, named loeflingiin, together with apigenin 6-C-glucoside (isovitexin), coumarins citropten and isompinellin, triterpenoids betulin and betulinic acid, and a mixture of phytosterols ß-sitosterol, stigmasterol and campesterol were isolated for the first time from the leaves of wild Plantago loeflingii L. (Plantaginaceae) collected in the Iraqi Kurdistan region. The plant is used by local people to treat wounds and as a vulnerary remedy. The structures of isolated compounds were determined by spectroscopic analysis. The activities of isovitexin and loeflingiinon the viability of breast (MCF7), ovarian (BG-1), endometrial (Ishikawa), and mesothelioma (IST-MES1) human cancer cells and two normal cell lines were determined with an MTT assay. Notably, the new 7-O-glucosyl flavone showed effects higher than cisplatin against the Ishikawa and IST-MESI cell lines. The significant biological activities exhibited by all the compounds isolated from P. loeflingii provided scientific evidence to support the use of the plant in the Kurdish traditional medicine.

Novel Skeletal Rearrangements of the Tigliane Diterpenoid Core.

To investigate the role of the secondary 5-hydroxy group in the activity of the anticancer drug tigilanol tiglate (2b) (Stelfonta), oxidation of this epoxytigliane diterpenoid from the Australian rainforest plant Fontainea picrosperma was attempted. Eventually, 5-dehydrotigilanol tiglate (3a) proved too unstable to be characterized in terms of biological activity and, therefore, was not a suitable tool compound for bioactivity studies. On the other hand, a series of remarkable skeletal rearrangements associated with the presence of a 5-keto group were discovered during its synthesis, including a dismutative ring expansion of ring A and a mechanistically unprecedented dyotropic substituent swap around the C-4/C-10 bond. Taken together, these observations highlight the propensity of the α-hydroxy-ß-diketone system to trigger complex skeletal rearrangements and pave the way to new areas of the natural products chemical space.

Chemical Composition and In Vitro Evaluation of Antioxidant and Antiproliferative Effects of Volatile Oils Hydrodistilled from Onobrychis carduchorum C.C. Towns., a Kurdish Traditional Plant.

The volatile oils hydrodistilled from the aerial parts and roots of O. carduchorum C.C Towns. (Fabaceae) have been chemically characterized for the first time. A total of 43 constituents with an abundance >0.03% were identified and quantified in the two oils by GC/MS and GC/FID analyses. They comprise 38 components (98.58%) of the oil isolated from the aerial parts (OCA) and 34 components (93.33%) of the oil from the roots (OCR). Six constituents, α-pinene (23.11 ± 0.1%), ß-elemene (17.33 ± 0.1%), 1,8-cineole (12.15 ± 0.2%), furfural (7.91 ± 0.1%), terpineol-4-ol (6.32 ± 0.2%), and limonene (4.13 ± 0.1%), accounted for about 75% of the total OCA oil. On the other hand, 1,8-cineole (15.79 ± 0.1%), furfural (10.44 ± 0.1%), ß-elemene (10.14 ± 0.2%), α-terpineol (7.74 ± 0.1%), linalool (7.45 ± 0.1%), and α-pinene (4.76 ± 0.1%) made up about 60% of the OCR oil. The IC50 values of the scavenging activities of the OCA and OCR oils towards the DPPH radical and H2O2 were 79.8 ± 0.5 and 153.3 ± 0.6 µg/mL and 394.09 ± 0.2 and 311.67 ± 0.4 µg/mL, respectively. In addition, in the MTS assay, the OCA and OCR oils showed significant antiproliferative effects against T47D, MDA-MB-453, BG-1, and A549 human cancer cells that were more powerful than those against two normal human cell lines, HEK-293 and HFF-1. The abundant presence of ß-elemene as an antiproliferative component of the two oils suggested the existence of a new chemotype of O. carduchorum.

Food Security beyond Cereals: A Cross-Geographical Comparative Study on Acorn Bread Heritage in the Mediterranean and the Middle East.

This article aims to contribute to the limited literature on traditional gastronomic knowledge concerning acorn-based bread by ethnographically documenting the ingredients, preparation techniques and consumption practices of baked goods made from acorn seeds and flour that are still used today or at least still present in living memory. A qualitative comparative case method was adopted, and ethnographic data were gathered from 67 people in six selected Mediterranean, Central Asian and Middle Eastern countries. The analysis highlighted distinct trajectories in the development of acorn-based bread, showing some differences in terms of ingredients, preparation techniques and baking methods in the two cultural and geographical macro-regions. By exploring the evolution of the alimentary role of acorn bread in the past century, our findings also support the hypothesis that the product, at least during the last two centuries, has mostly been used as a famine food. By acknowledging the cultural importance of acorn fruits and acorn-based products, this study suggests that the rediscovery of acorn-based products and associated traditional knowledge may foster the sustainable development of rural and marginal regions in the Mediterranean, Middle East and Central Asia. This could help to reinforce the resilience of local communities and thus increase food security. Furthermore, reassessing acorns as a foodstuff may aid in developing innovative products in line with emerging trends in the food sector, which is looking for new non-cereal-based bakery products and other novel culinary applications.

Cannabinol: History, Syntheses, and Biological Profile of the Greatest "Minor" Cannabinoid.

Cannabis (Cannabis sativa L.) is an outstanding source of bioactive natural products, with more than 150 different phytocannabinoids isolated throughout the decades; however, studies of their bioactivity have historically concentrated on the so-called "big four" [∆9-THC (1a), CBD (2a), CBG (3a) and CBC (4a)]. Among the remaining products, which have traditionally been referred to as "minor cannabinoids", cannabinol (CBN, 5a) stands out for its important repercussions and implications on the global scientific landscape. Throughout this review, we will describe why CBN (5a) deserves a prominent place within the so-called "cannabinome", providing an overview on its history, the syntheses developed, and its bioactivity, highlighting its promising pharmacological potential and the significant impact that the study of its chemistry had on the development of new synthetic methodologies.

Synthesis characterization of Zn-based MOF and their application in degradation of water contaminants.

Metal-organic frameworks (MOFs) are currently popular porous materials with research and application value in various fields such as medicine and engineering. Aiming at the application of MOFs in photocatalysis, this paper mainly reviews the main synthesis methods of ZnMOFs and the latest research progress of Zn MOF-based photocatalysts to degrade organic pollutants in water, such as organic dyes. This nanomaterial is being used to treat wastewater and has proven to be very efficient because of its exceptionally large surface area and porous nature. The results show that Zn-MOFs are capable of high degradation of the above pollutants and over 90% of degradation was observed in publications. In addition, the reusability percentage was examined and studies showed that the Zn-MOF nanostructure has very good stability and can continue to degrade a high percentage of pollutants after several cycles. This review focuses on Zn-MOFs and their composites. First, the methods of synthesis and characterization of these compounds are given. Finally, the application of these composites in the process of photocatalytic degradation of dye pollutants such as methylene blue, methyl orange, crystal violet, rhodamine B, etc. is explained.

Application of nanotechnology to herbal antioxidants as improved phytomedicine: An expanding horizon.

Phytotherapy, based on medicinal plants, have excellent potential in managing several diseases. A vital part of the healthcare system is herbal medicines, consisting of therapeutic agents with high safety profile and no or least adverse effects. Herbs or medicinal plants show anticancer, antioxidant, and gene-protective activity, which is useful for pharmaceutical industries. In vitro, the extract of antioxidant compounds prevents the growth of colon and liver cancer cells, followed by a dose-dependent method. The screening of extracts is done by using in vitro models. Reactive oxygen species (ROS) and free radicals lead to diseases based on age which promotes oxidative stress. Different types of ROSs available have central roles in the normal physiology and functioning of processes. Herbal or traditional plant medicines have rich antioxidant activity. Despite the limited literature on the health effect of herbal extract or spices. There are many studies examining the encouraging health effects of single phytochemicals instigating from the medicinal plant. This review provides a detailed overview on herbal antioxidants and how application of nanotechnology can improve its biological activity in managing several major diseases, and having no reported side effects.

Design, Formulation, and Evaluation of Aloe vera Gel-Based Capsaicin Transemulgel for Osteoarthritis.

Topical treatments are a potential therapeutic option for the therapy of osteoarthritis, with significant data supporting the effectiveness and safety of topical formulation. Topical gel formulations may offer an alternative to oral formulations to relieve osteoarthritis (OA) pain while decreasing systemic exposure. Topical capsaicin transemulgel may represent an effective and safe alternative. The transemulgel was prepared from aqueous Aloe vera gel and Carbopol 934 with capsaicin in clove oil emulsion. The optimized transemulgel of capsaicin showed a pH of 6.1 ± 0.1 and viscosity of 15263-998 cps. Data from in vitro diffusion demonstrated improved permeability properties. The formulation caused no skin irritation when applied topically. The optimal transemulgel spreadability was found to be 20.23 g·cm/s. In vitro and ex vivo studies of the optimized formulation were performed. The skin irritant test was performed on rat skin with an optimized and marketed formulation. Both showed no irritation on the skin. The transemulgel of the capsaicin with Aloe vera gel was proven to be effective for osteoarthritis therapy.

Cryptic Epoxytiglianes from the Kernels of the Blushwood Tree (Fontainea picrosperma).

The kernels of the Australian blushwood tree (Fontainea picrosperma) are the source of the veterinary anticancer drug tigilanol tiglate (2a, Stelfonta) and contain a concentration of phorboids significantly higher than croton oil, the only abundant source of these compounds previously known. The oily matrix of the blushwood kernels is composed of free fatty acids and not by glycerides as found in croton oil. By active partitioning, it was therefore possible to recover and characterize for the first time a cryptic tigliane fraction, that is, the diterpenoid fraction that, because of its lipophilicity, could not be obtained by solvent partition of crude extracts. The cryptic tigliane fraction accounted for ca. 30% of the tigliane kernel titer and was quantified by 1H NMR spectroscopy and profiled by HPLC-MS. Long-chain (linoleates and/or oleates) 20-acyl derivatives of the epoxytigliane diesters tigilanol tiglate (EBC-46, 2a), EBC-47 (4a), EBC-59 (5a), EBC-83 (6a), and EBC-177 (7a) were identified. By chemoselective acylation of EBC-46 (2a) and EBC-177 (7a) the natural triesters 2b and 7b and a selection of analogues were prepared to assist identification of the natural compounds. The presence of a free C-20 hydroxy group is a critical requirement for PKC activation by phorbol esters. The unexpected activity of 20-linoleoyl triester 2b in a cytotoxicity assay based on PKC activation was found to be related mainly to its hydrolysis to tigilanol tiglate (2a) under the prolonged conditions of the assay, while other esters were inactive. Significant differences between the esterification profile of the epoxytigliane di- and triesters exist in F. picrosperma, suggesting a precise, yet elusive, blueprint of acyl decoration for the tigliane polyol 5-hydroxyepoxyphorbol.

Minor Phytocannabinoids: A Misleading Name but a Promising Opportunity for Biomedical Research.

Despite the very large number of phytocannabinoids isolated from Cannabis (Cannabis sativa L.), bioactivity studies have long remained focused on the so called "Big Four" [Δ9-THC (1), CBD (2), CBG (3) and CBC (4)] because of their earlier characterization and relatively easy availability via isolation and/or synthesis. Bioactivity information on the chemical space associated with the remaining part of the cannabinome, a set of ca 150 compounds traditionally referred to as "minor phytocannabinoids", is scarce and patchy, yet promising in terms of pharmacological potential. According to their advancement stage, we sorted the bioactivity data available on these compounds, better referred to as the "dark cannabinome", into categories: discovery (in vitro phenotypical and biochemical assays), preclinical (animal models), and clinical. Strategies to overcome the availability issues associated with minor phytocannabinoids are discussed, as well as the still unmet challenges facing their development as mainstream drugs.

Biosynthesis of silver nanoparticles using Lawsonia inermis and their biomedical application.

Developing biosynthesis of silver nanoparticles (Ag-NPs) using plant extract is an environmentally friendly method to reduce the use of harmful chemical substances. The green synthesis of Ag-NPs by Lawsonia inermis extract and its cellular toxicity and the antimicrobial effect was studied. The physical and chemical properties of synthesised Ag-NPs were investigated using UV-visible spectroscopy, infrared spectroscopy, X-ray diffraction (XRD), scanning, and transmission electron microscopy. The average size of Ag-NPs was 40 nm. The XRD result shows peaks at 2θ = 38.07°, 44.26°, 64.43°, and 77.35° are related to the FCC structure of Ag-NPs. Cytotoxicity of synthesised nanoparticles was evaluated by MTT toxicity test on breast cancer MCF7 cell line. Observations showed that the effect of cytotoxicity of nanoparticles on the studied cell line depended on concentration and time. The obtained IC50 was considered for cells at a dose of 250 µg/ml. Growth and survival rates decreased exponentially with the dose. Antimicrobial properties of Ag-NPs synthesised with extract were investigated against Escherichia coli, Salmonella typhimurium, Bacillus cereus, and Staphylococcus aureus to calculate the minimum inhibitory concentration and the minimum bactericidal concentration of (MBC). The results showed that the synthesised Ag-NPs and the plant extract have antimicrobial properties. The lowest concentration of Ag-NPs that can inhibit the growth of bacterial strains was 25 µg/ml.

A chemometric assessment and profiling of the essential oils from Hibiscus sabdariffa L. from Kurdistan, Iraq.

Hibiscus sabdariffa L. is a tropical plant belonging to the Malvaceae family. In Kurdistan, the Autonomous Region of Iraq, water infusion of H. sabdariffa calyces is recommended for the treatment of hypotension and the common cold. Three distillation techniques: hydrodistillation (HD), steam distillation (SD), and solvent-free microwave-assisted extraction (SFME) have been compared to obtain the essential oils from calyces. The composition of the extracts was investigated by GC-FID and GC-MS. A total of 62 compounds have been identified, from which 55 components were found in HD distillates (95.75%), 37 components in SFME (96.06%), and 29 in SD (99.63%). Chemometric tools were applied to optimise and evidence the relation between distillation techniques and composition of the obtained essential oils as an investigation for the essential oils commercialisation approach of Hibiscus sabdariffa L. that have been done from a long time using conventional hydrodistillation in the local Herbal and Tea markets in Kurdistan.

Phytochemistry and Biological Activities of Iris Species Growing in Iraqi Kurdistan and Phenolic Constituents of the Traditional Plant Iris postii.

A dozen Iris species (Iridaceae) are considered traditional remedies in Kurdistan, especially for treating inflammations. Phytochemical studies are still scarce. The information reported in the literature about Iris species growing in Kurdistan has been summarized in the first part of this paper, although, except for Iris persica, investigations have been performed on vegetal samples collected in countries different from Kurdistan. In the second part of the work, we have investigated, for the first time, the contents of the methanolic extracts of Iris postii aerial parts and rhizomes that were collected in Kurdistan. Both extracts exhibited a significant dose-dependent free radical scavenging and total antioxidant activities, comparable to those of ascorbic acid. Medium-pressure liquid chromatographic separations of the two extracts afforded l-tryptophan, androsin, isovitexin, swertisin, and 2″-O-α-l-rhamnopyranosyl swertisin from the aerial parts, whereas ε-viniferin, trans-resveratrol 3,4'-O-di-ß-d-glucopyranoside, and isotectorigenin were isolated from the rhizomes. This is the first finding of the last three metabolites from an Iris species. The various remarkable biological activities of isolated compounds scientifically sustain the traditional use of I. postii as a medicinal plant.

New acetylenic metabolites from the toxic mushroom Tricholoma pardinum.

Four unprecedented acetylenic alcohols, (Z)-non-7-en-5-yn-1,2,4-triol (1), (Z)-non-7-en-5-yn-1,4-diol (2), (Z)-1,2-dihydroxynon-7-en-5-yn-4-one (3), and (Z)-1-hydroxynon-7-en-5-yn-4-one (4) were isolated from the poisonous mushroom Tricholoma pardinum (Agaricales, Basidiomycota), together with the known compounds 1H-indole-3-carbaldehyde (5) and 6-hydroxy-1H-indole-3-carbaldehyde (6). Their structures were determined by NMR and IR spectroscopy, and mass spectrometry. The crude acetone extract of the mushroom showed potent anti-arthropod activity against Tetranychus urticae (Acarinae), a dangerous crop pest.[Figure: see text].

The allylic oxidation of tigliane esters.

As part of a study on the structure-activity relationships of the anticancer agent tigilanol tiglate (EBC-46, 2), the allylic oxidation of phorbol triacetate (1c) and of the acetonide of its 3αH-dihydroderivative (5) was investigated. The aim was to introduce an oxygen function at C-5 en route to point-like analogues of 2, but functionalization of C-10 was instead observed. This was followed by oxidative fragmentation of ring B to the 9,10-secotigliane derivative 6 and oxidation of the endocyclic Δ6 double bond to the C-6/C-10 oxygen bridged 7-oxotigliane 7. Despite the over-functionalization of ring B, these observations suggest the possibility to modify positions overlooked in the oxidase phase of tigliane biosynthesis and explore novel areas of the phorbol chemical space.

Where tulips and crocuses are popular food snacks: Kurdish traditional foraging reveals traces of mobile pastoralism in Southern Iraqi Kurdistan.

BACKGROUND: Iraqi Kurdistan is a special hotspot for bio-cultural diversity and for investigating patterns of traditional wild food plant foraging, considering that this area was the home of the first Neolithic communities and has been, over millennia, a crossroad of different civilizations and cultures. The aim of this ethnobotanical field study was to cross-culturally compare the wild food plants traditionally gathered by Kurdish Muslims and those gathered by the ancient Kurdish Kakai (Yarsan) religious group and to possibly better understand the human ecology behind these practices. METHODS: Twelve villages were visited and 123 study participants (55 Kakai and 68 Muslim Kurds) were interviewed on the specific topic of the wild food plants they currently gather and consume. RESULTS: The culinary use of 54 folk wild plant taxa (corresponding to 65 botanical taxa) and two folk wild mushroom taxa were documented. While Kakais and Muslims do share a majority of the quoted food plants and also their uses, among the plant ingredients exclusively and commonly quoted by Muslims non-weedy plants are slightly preponderant. Moreover, more than half of the overall recorded wild food plants are used raw as snacks, i.e. plant parts are consumed on the spot after their gathering and only sometimes do they enter into the domestic arena. Among them, it is worth mentioning the consumption of raw wild crocus corms, also still common in Turkish Kurdistan and that of wild tulip bulbs, which was documented to be popular until the beginning of the twentieth century in the Middle East. Comparison with other ethnobotanical field studies recently conducted among surrounding populations has shown that Kurds tend to gather and consume the largest number of non-weedy wild vegetables. CONCLUSION: The collected data indicate robust traces of nomadic pastoralism in Kurdish traditional foraging. This finding confirms that studies on wild food plant gathering in the Fertile Crescent and Turco-Arabic-Iranic regions of the Middle East are crucial for understanding the possible evolution of wild food plant gathering through history within the post-Neolithic continuum between pastoralism and horticulturalism.

Stereoselective preparation of key intermediates for the synthesis of iso-, neuro- and phyto-prostane family members: inaugural asymmetric synthesis of 17-E2c-dihomo- and 17-F2c-dihomo-isoprostanes.

A practical methodology for the synthesis of key intermediates for isoprostane, neuroprostane and dihomo-isoprostane preparation has been described. The key strategy involved a three stage C-12 stereocenter inversion of the configuration of a Corey lactone, commercially available in an enantiopure form. The key intermediate was then used to prepare 17-E2c-dihomo-isoprostane and 17-F2c-dihomo-isoprostane.

Chemical Composition and Antifungal Activity of Essential Oils from Flowers, Leaves, Rhizomes, and Bulbs of the Wild Iraqi Kurdish Plant Iris persica.

Essential oils-obtained by hydrodistillation of different parts of Iris persica L. were investigated for the first time by GC-FID and GC-MS; moreover, their antifungal activities were determined: 34,. 32, 27, and 17 compounds were identified in the oils from air-dried flowers, leaves, rhizomes and fresh. bulbs, respectively, representing ≥ 98% each oil. The major constituents of the flower essential oil were phenylethanol (24.8%) and furfural (13.8%), which, as the main component, constituted also 39.0% and 22.2% of the leaf and rhizome volatile fractions, respectively. Phenylacetaldehyde (37.1%) was the main constituent of the bulb volatile fraction. In in vitro tests, moderate antifungal activity was detected for the oils against strains of the human pathogenic fungal species Gandida albicans, Microsporum canis, and Trichophyton mentagrophytes, the plant-fungal pathogen Pyricularia oryzae, and the fungal food contaminant Aspergillus carbonarius,. The highest activity was exhibited by the essential oils from leaves and flowers, suggesting that they could be considered natural antimicrobial agents.

Phytochemistry and Ethnopharmacology of Some Medicinal Plants Used in the Kurdistan Region of Iraq.

The majority of Kurds inhabit a region that includes adjacent parts of Iran, Iraq, Syria and Turkey. This review shows that the traditional medicine is still used by Kurdish peoples and underlines the medicinal value of a great number of plants used locally. The medicinal uses include the treatment of a variety of diseases, ranging from simple stomach-ache to highly complicate male and female disorders; even sexual weakness and kidney stones are treated by plants. The majority of the plants that are used are for curing gastro-intestinal disorders and inflammation, followed by urinary tract disorders, skin burns, irritations and liver problems. In the last part of this paper, we also report the first results of our ongoing research project on the constituents of some uninvestigated Kurdish medicinal plants. The C-glycosylflavone embinin, the α-methylene acyl derivative 6-tuliposide A, and the iridoids aucubin and ajugol were isolated for the first time from Iris persica, Tulipa systole and Verbascum calvum, respectively. These plants are traditionally used against inflammation, pain, and skin burns.