9-Anthraldehyde oxime: a synthetic tool for variable applications

Abstract Oximes are one of the most important and prolific functional groups in organic chemistry; among them, 9-anthraldehyde oxime represents a valuable example both from the preparative side and the synthetic applications. There are many strategies to prepare 9-anthraldehyde oxime from different functional groups that were summarized in the present review, focusing on the most recent and innovative. The main synthetic applications of 9-anthraldehyde oxime are presented and thoroughly discussed, focusing on the most recent and innovative synthetic strategies. Graphic abstrac

Bioactive Constituents from the Traditional Kurdish plant Iris persica

In the first phytochemical investigation of non-volatile secondary metabolites from the Kurdish traditional plant Iris persica L, (-)-embinin was isolated from flowers and leaves, isovitexin from flowers, trans-resveratrol-3- O-β-D-glucopyranoside from rhizomes and tectorigenin from bulbs. The complete NMR spectra of embinin are reported for the first time. In an MTT assay, embinin showed an inhibition activity higher than the well-known antitumor drug cisplatin against five of the six tested human tumor cells. Moreover, embinin showed a significant DPPH radical scavenging activity (IC50 value of 112.16) comparable to the reference antioxidant ascorbic acid. The remarkable biological activities exhibited by the extracts of Iris persica and isolated compounds have validated the uses of I. persica in the traditional medicine of Kurdistan

Fatty Acid Characterization from Flowers of Tulipa Systola Stapf. Using Gas Chromatography-Mass Spectrometry (GC-MS)

The structural analysis of fatty acid mixtures by gas chromatography-mass spectrometry (GC-MS) has been characterized from Tulipa systola Stapf. Flowers, wild plant growing in Kurdistan region-Iraq. The fatty acids of the lipid fraction were mainly saturated fatty acids, the highest value recorded for isopropyl palmitic acid methyl ester (47.02%), glycerol α-palmitic acid methyl ester (19.66%) and stearic acid methyl ester (8.64%). In addition, two unsaturated fatty acids that characterized were oleic acid methyl ester (6.95%) and undecylenic acid methyl ester (2.22%)

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

Iridoids Isolation from a Phytochemical Study of the Medicinal Plant Teucrium parviflorum Collected in Iraqi Kurdistan

Herbal medicines are still widely practiced in Kurdistan Region-Iraq, especially by people living in villages on mountainous regions. Among plants belonging to the genus Teucrium (family Lamiaceae), which are commonly employed in the Kurdish traditional medicine, we have analyzed, for the first time, the methanol and aqueous methanol extracts of T. parviflorum aerial parts. The plant is mainly used by Kurds to treat jaundice, liver disorders and stomachache. We aimed to determine the phytochemical profile of the extracts and the structures of the main components, so to provide a scientific rationale for the ancient use of the plant in the ethno-pharmacological field. TLC analysis of the two extracts on silica gel and reversed phase TLC plates, using different visualization systems, indicated similar contents and the presence of phenolics, flavonoids, terpenoids and sugars. The chlorophyll-free extracts exhibited weak/no antimicrobial activities against a panel of bacteria (MICs = 800–1600 µg/mL) and fungal strains (MICs ≥ 5 mg/mL). At the concentration of 600 µg/mL, the methanol extract showed moderate antiproliferative effects against A549 and MCF-7 cancer cell lines in the MTS assay. Moreover, both extracts exhibited a significant dose-dependent free radical scavenging action against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical (EC50 = 62.11 and 44.25 μg/mL, respectively). In a phytochemical study, a high phenolic content (77.08 and 81.47 mg GAE/g dry extract, respectively) was found in both extracts by the Folin–Ciocalteu assay. Medium pressure liquid chromatographic (MPLC) separation of the methanol extract on a reversed phase cartridge eluted with a gradient of MeOH in H2O, afforded two bioactive iridoid glucosides, harpagide (1) and 8-O-acetylharpagide (2). The structures of 1 and 2 were established by spectral data, chemical reactions, and comparison with the literature. Interestingly, significant amounts of hepatotoxic furano neo-clerodane diterpenoids, commonly occurring in Teucrium species, were not detected in the extract. The wide range of biological activities reported in the literature for compounds 1 and 2 and the significant antiradical effects of the extracts give scientific support to the traditional use in Iraqi Kurdistan of T. parviflorum aerial parts for the preparation of herbal remedies

Highly regioselective and diastereoselective synthesis of novel pyrazinoindolones via a base-mediated Ugi-N-alkylation sequence

An efficient base-mediated/metal-free approach has been developed for the synthesis of 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-3-carboxamide derivatives via intramolecular indole N–H alkylation of novel bis-amide Ugi-adducts. In this protocol the Ugi reaction of (E)-cinnamaldehyde derivatives, 2-chloroaniline, indole-2-carboxylic acid and different isocyanides was designed for the preparation of bis-amides. The main highlight of this study is the practical and highly regioselective preparation of new polycyclic functionalized pyrazino derivatives. This system is facilitated by Na2CO3 mediation in DMSO and 100 °C conditions

Diethylaminoethyl Cellulose (DEAE-C) between Chromatography and Synthetic Applications

The aim of this review is to point out the attention of the reader to the use of DEAE-C in organic reactions, possibly not only devoted to the preparation of heterocycles but potentially extending to other classes of organic compounds. Being DEAE-C an ammonium salt commonly used in chromatographic applications, it can be considered as a potential mild acid catalyst or a proton donor and these features can in theory catalyze standard acid-catalyzed organic reactions. In addition, the resin nature of DEAE-C could suggest the way to perform organic reactions in the solid state

DEAE-cellulose-catalyzed synthesis of 5-hydroxy-isoxazolidines and their synthetic uses towards nucleoside analogues

5-Hydroxy-isoxazolidinic heterocycles can be easily prepared from hydroxamic acids and suitable ,- unsaturated aldehydes or ketones in good yields from solid state synthesis, selectively promoted by DEAE-C. The synthesized products were efficiently derivatized with representative heterobases for the preparation of nucleoside analogues suitable for biological evaluation and SAR analysis

New Tricholidic Acid Triterpenoids from the Mushroom <i>Tricholoma ustaloides</i> Collected in an Italian Beech Wood

The secondary metabolites produced by Tricholoma ustaloides Romagn., a mushroom species belonging to the large Tricholoma genus (Basidiomycota, Tricholomataceae), are unknown. Therefore, encouraged by the interesting results obtained in our previous chemical analyses of a few Tricholoma species collected in Italian woods, we aimed to investigate the secondary metabolites of Tricholoma ustaloides. The chemical analysis involved the isolation and characterization of secondary metabolites through an extensive chromatographic study. The structures of isolated metabolites, including the absolute configuration, were established based on a detailed analysis of MS, NMR spectroscopic, optical rotation, and circular dicroism data, and on comparison with those of related compounds reported in the literature. Two novel lanostane triterpenoids, named tricholidic acids B and C, together with triglycerides, a mixture of free fatty acids, five unidentified metabolites, and the known rare saponaceolides F and J, tricholidic acid, and tricholomenyn C, were isolated from an EtOAc extract of fruiting bodies of Tricholoma ustaloides that were collected in an Italian beech wood. This is the second example of isolation of tricholidic acid derivatives from a natural source. Saponaceolides F and J exhibited high cytotoxicity (IC50 values ≤ 10 μM) against a panel of five human cancer cell lines. The toxicity against myeloid leukemia (HL-60), lung cancer (A-549), hepatocellular cancer (HepG2), renal cancer (Caki-1), and breast cancer (MCF-7) cells was higher than that shown by the very well-known cytotoxic drug cisplatin

Phytochemistry and Ethnopharmacology of Medicinal Plants Used on Safeen Mountain in the Kurdistan Region of Iraq.

In remote villages of Kurdistan-Iraq, such as in those on Safeen Mountain, decoctions, potions, and oils from the local herbal tradition have provided the only medicinal remedies for centuries, up to today. A variety of diseases are treated with different plant preparations, ranging from simple rheumatism to diarrhea, skin diseases, and highly complicated kidney and heart problems. This survey describes, for the first time, the mostly used medicinal plants, resulting from several interviews with local herbal healers. The bioactivity of some isolated compounds is, indeed, strictly related to traditional uses of plants in Safeen Mountain Province. We also report the preliminary results of our ongoing research project on the constituents of the still uninvestigated plant Pterocephalus nestorianus Nab., which is traditionally used against inflammation and oral diseases. Luteolin-7- O-glucoside, 3,5-di- O-caffeoylquinic acid and loganic acid were isolated