N. Z. Mamadalieva

Flavonoids in Scutellaria immaculata and S. ramosissima (Lamiaceae) and their biological activity

Objectivesu2002 The aim of this study was to investigate the flavonoid composition of Scutellaria immaculata and S.u2003ramosissima (Lamiaceae) and the in‐vitro biological activity of their extracts and flavonoids.

Chemical profiling of Phlomis thapsoides (Lamiaceae) and in vitro testing of its biological activities

A phytochemical study of Phlomis thapsoides (Lamiaceae) resulted in the isolation of one new compound, 6,10,17-trimethyl-2-octadecanone, and three known compounds (sitosterol-3-O-β-glucoside, and the iridoid glucosides ipolamiide and lamiide). The structures of the isolated compounds were elucidated using mass spectrometry, 1D/2D NMR spectroscopy experiments in comparison with published data. The chemical composition of the essential oil obtained from aerial parts of P. thapsoides was determined by gas liquid chromatography and gas liquid chromatography-mass spectroscopy. The main volatile constituents were phenylethyl alcohol (6.81u2009%), trans-3-hexenol (5.55u2009%), 1-octen-3-ol (5.10u2009%), α-cadinol (4.92u2009%), and α-muurolol (4.67u2009%). The antioxidant activity of the extracts was evaluated by three methods: 1,1-diphenyl-2-picrylhydrazyl free radical scavenging activity, 2,2′-azinobis-[3-ethylbenzthiazoline-6-sulfonic acid] and ferric reducing antioxidant power assay along with the determination of total phenolic content. Although the ethyl acetate extract contained 362.06u2009mg of gallic acid equivalents, the antioxidant activities, as revealed by 1,1-diphenyl-2-picrylhydrazyl, 2,2′-azinobis-[3-ethylbenzthiazoline-6-sulfonic acid] and ferric reducing antioxidant power assays, were of medium strength (IC50 of 73.08u2009±u20093.18, 9.48u2009±u20090.71u2009µg/mL and 9.33u2009±u20090.17u2009mM of FeSO4 equivalents, respectively). Only lamiide inhibited soybean 5-lipoxygenase with an IC50 value of 72.92u2009µg/mL in vitro. In-silico molecular modeling studies on 5-lipoxygenase and human 5-lipoxygenase-activating protein were used to evaluate the potential anti-inflammatory activity. Sitosterol-3-O-β-glucoside followed by the iridoid glucoside lamiide exhibited the highest inhibition of 5-lipoxygenase whereas the new compound 6,10,17-trimethyl-2-octadecanone and sitosterol-3-O-β-glucoside exhibited the highest inhibition of 5-lipoxygenase-activating protein as evidenced from their higher fitting scores. The cytotoxicity of the plant extracts and lamiide against Caco2 and HepG-2 cancer cells resulted in IC50 values of >100u2009µg/mL indicating a low cytotoxicity.

Phytochemical analysis and bioactivity of the aerial parts of Abutilon theophrasti (Malvaceae), a medicinal weed

Phytochemical investigations of aerial parts of Abutilon theophrasti yielded (6S,9R)-roseoside (1) and (6S,9S)-roseoside (2) which are new for the genus. The elucidation of the chemical structures was established by mass spectrometry, 1D and 2D NMR experiments. Although methanol extracts contained 48.5 ± 7.2 mg of caffeic acid equivalents and 15.87 ± 4.6 mg of quercetin equivalents, the antioxidant activity, as revealed by DPPH and ABTS assays, was of medium strength (EC50 of 306.2 ± 16.3 and 394.3 ± 14.8 μg/mL, respectively). A. theophrasti extract inhibits soybean 5-LOX with IC50 value 2.89 ± 0.2 mg/mL. The cytotoxicity of the methanol extract against MCF-7, CCRF-CEM and CEM/ADR5000 cancer cells resulted in IC50 values of 505.8 ± 34.7 μg/mL for MCF-7, 75.6 ± 7.1 μg/mL for CCRF-CEM, and 89.5 ± 13.4 μg/mL for CEM/ADR 5000 cells.

PHYTOECDYSTEROIDS OF Silene viridiflora

The known ecdysteroids polipodin B, 2-deoxyecdysterone, ecdysterone, 26-hydroxypolipodin B, integristerone A, and sileneosides A and D were observed in the aerial part of Silene viridiflora L. (Caryophyllaceae). 26-Hydroxypolipodin B was observed in this species for the first time.

Fatty-acid composition and antibacterial activity of CHCl3 extracts of three plants of the genus Silene

A total of 84 species of the plant genus Silene (Caryophyllaceae) are indigenous to Central Asia [1]. We studied previously ecdysteroids from the aerial part of three species of Silene [2–4]. Lipids extracted by CHCl3 during isolation of the ecdysteroids were studied in order to utilize more of the raw material. Ecdysteroids were isolated by soaking the ground air-dried aerial part of the plants in MeOH at room temperature for 1 d. Then, the extract was filtered. The MeOH was distilled in a rotary evaporator. The solid was dissolved in water and treated with CHCl3. The ecdysteroids remained in the aqueous layer. The CHCl3 part of the extract was not used. We isolated the lipids from it using column chromatography over silica gel and solvent system hexane:Et2O (1:1). This isolated neutral lipids (NL). Their composition was determined using TLC and hexane:Et2O (4:1 and 1:1). The principal components of the NL were triglycerides, free fatty acids, and free sterols. Fatty acids were isolated from NL after their alkaline hydrolysis and were analyzed by GC as the methyl esters on a Chrom 5 instrument with a flame-ionization detector using a metallic column (2.5 m) packed with Chromaton N-AW with Reoplex-400 (15%). Table 1 presents the fatty-acid composition. It can be seen that the qualitative fatty-acid compositions of NL from the aerial parts of the aforementioned species of Silene were identical and consisted of 15 acids. Their quantitative compositions differed. This was evident in the content of the principal acids, the saturated one of which was palmitic acid (16:0); the unsaturated ones, two essential fatty acids -6 (18:2) and -3 (18:3). Palmitic acid dominated the NL in plants 2 and 3; the sum of linoleic and linolenic acids, in S. viridiflora. Next the antibacterial activity of these CHCl3 extracts was determined by the disk diffusion test [5]. For this, they were dissolved in DMSO. Microorganisms were grown in agar dishes at 30°C overnight in Mueller–Hinton medium (Oxoid). The suspension (100 L) contained 108 CFU/mL. Sterile filter disks (5-mm diameter) were soaked with extract solution (20 L, 5 mg/mL) and placed on the surface of the innoculated Petri dishes. The dishes were incubated at 37°C for 24 h. The antibacterial activity was estimated by measuring the inhibition zone formed around the disks. We used five disks in each Petri dish. Each test was performed in triplicate. The test cultures of microorganisms were the following: Klebsiella pneumoniae 40602; Micrococcus luteus obtained from the Microbiology Faculty, Manchester University, GB; Pseudomonas aeruginosa NCTC6749; Enterococcus faecalis NCTC775; Proteus rettgeri NCIMB9570 obtained from the National Collection of Great Britain (NCTC); bacterial strains P. agglomerans T26, B. cereus T80, and Staphylococcus saprophyticus T415 obtained from the Biology Faculty, National University of Uzbekistan. Antimicrobial activity was found by testing against several bacterial cultures. The CHCl3 extract of S. brachuica inhibited growth of three Gram-negative (E. faecalis, P. rettgeri, and P. aeruginosa) and one Gram-positive (M. luteus) bacterial strain. The CHCl3 extract of S. viridiflora was active against M. luteus, P. rettgeri, K. pneumoniae, and P. aeruginosa. The extract of S. wallichiana exhibited activity against pathogenic bacteria M. luteus and P. aeruginosa but was weaker than extracts from the other species of Silene. Thus, the microbiological studies indicated that extracts of these species of Silene exhibited antimicrobial activity against various species of bacteria.

Phytoecdysteroids from the Silene genus

Research results on the isolation and identification of ecdysteroids from plants of the Silene L. genus were presented.

Composition of the essential oils of three Uzbek Scutellaria species (Lamiaceae) and their antioxidant activities.

Abstract The chemical composition of the essential oils obtained from aerial parts of Scutellaria immaculata Nevski ex Juz., Scutellaria ramosissima M. Pop. and Scutellaria schachristanica Juz. (Lamiaceae) growing wild in Uzbekistan was analysed by GC and GC–MS. The main constituents of the essential oils from S. immaculata were acetophenone (30.39%), eugenol (20.61%), thymol (10.04%) and linalool (6.92%), whereas constituents of the essential oils fromS. schachristanica were acetophenone (34.74%), linalool (26.98%) and eugenol (20.67%). The S. ramosissima oil is dominated by germacrene D (23.96%), β-caryophyllene (11.09%), linalool (9.63%) and hexadecanoic acid (8.34%). The essential oils of Scutellaria species exhibited weaker antioxidant effects in DPPH, ABTS and FRAP assays. In FRAP assay, only eugenol exhibited a substantial reducing power IC50 = 2476.92 ± 15.8 (mM Fe(II)/g). Graphical Abstract

Synthesis of Substituted Thieno[2,3-d]pyrimidin-4-ones and Their Testing for Evaluation of Cytotoxic Activity on Mammalian Cell Models

From 2-amino-3-ethoxycarbonyl-4,5-dimethyl-, -polymethylenethiophenes (1-4) were synthesized 2,3-disubstituted thieno[2,3-d]dihydropyrrolo-, tetrahydropyrido-, and tetrahydroazepino[1,2-a]pyrimidin-4-ones (5-16) for pharmacological investigations. The 12 compounds (5-16) were individually evaluated for their antiproliferative activities on mammalian cancer cell models. All tested compounds showed weak affection on human cervix adenocarcinoma cells (HeLa) whereas some of the tested compounds exhibited more consistent inhibition of cell growth on murine myeloma cells (P3X). In both cases some compounds enhanced cell proliferation.

Phytoecdysteroids of Silene guntensis and their in vitro Cytotoxic and Antioxidant Activity

Phytoecdysteroids from aerial parts of Silene guntensis B. Fedtsch were investigated and three phytoecdysteroids were isolated: 2,3-diacetate-22-benzoate-20-hydroxyecdysone (1), 2-deoxy-20-hydroxyecdysone (2), and 20-hydroxyecdysone (3). Their chemical structures were elucidated by DEPT, COSY, 1H and 13C NMR spectroscopy. The isolated compounds 1 - 3 and crude extracts were evaluated for their antiproliferative and antioxidant activities. They exhibited substantial inhibition of cell growth against human cervix adenocarcinoma (HeLa), hepatocellular carcinoma (HepG-2), and breast adenocarcinoma (MCF-7) cells. The chloroform extract showed potent cytotoxic effects [IC50 values (26.58 ± 1.88) μg/mL, (20.99 ± 1.64) μg/mL, and (18.89 ± 2.36) μg/mL, respectively]. The new compound 1 was mildly cytotoxic compared to extracts [(127.97 ± 11.34), (106.76 ± 7.81), and (203.10 ± 19.56) μg/mL, respectively]. Water and n-butanol extracts exhibited good antioxidant activities [IC50 values of (68.90 ± 6.45) μg/mL and (69.12 ± 5.85) μg/mL, respectively].

Aromatic Medicinal Plants of the Lamiaceae Family from Uzbekistan: Ethnopharmacology, Essential Oils Composition, and Biological Activities

Plants of the Lamiaceae family are important ornamental, medicinal, and aromatic plants, many of which produce essential oils that are used in traditional and modern medicine, and in the food, cosmetics, and pharmaceutical industry. Various species of the genera Hyssopus, Leonurus, Mentha, Nepeta, Origanum, Perovskia, Phlomis, Salvia, Scutellaria, and Ziziphora are widespread throughout the world, are the most popular plants in Uzbek traditional remedies, and are often used for the treatment of wounds, gastritis, infections, dermatitis, bronchitis, and inflammation. Extensive studies of the chemical components of these plants have led to the identification of many compounds, as well as essentials oils, with medicinal and other commercial values. The purpose of this review is to provide a critical overview of the literature surrounding the traditional uses, ethnopharmacology, biological activities, and essential oils composition of aromatic plants of the family Lamiaceae, from the Uzbek flora.