Publications de la Division Santé : ABSTRACT DES ARTICLES SCIENTIFIQUES

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ABSTRACT DES ARTICLES SCIENTIFIQUES

Division Santé

 

EXPRESSION OF ADENOSINE 5-MONOPHOSPHATE—ACTIVATED PROTEIN KINASE IN OVINE TESTIS (OVIS ARIES): IN VIVO REGULATION BY NUTRITIONAL STATE

  1. Taïbi, J. Dupont, Z. Bouguermouh, P. Froment, C. Ramé, A. Anane,
    Z. Amirat, F. Khammar

Animal Reproduction Science, 178 (2017) 9-22.

Keywords: Domestic ruminant, Die, Steroidogenesis, AMPK, Signal transduction


 

CATALYST-FREE ONE-POT SYNTHESIS OF CHROMENO IMIDAZOPYRIDINONES BY AN AZA-MICHAEL ADDITION/REARRANGEMENT/ HETEROCYCLIZATION TANDEM REACTION

  1. Lakhdari, O. Talhi, R. Hassaine, N. Taibi, R. F. Mendese, F. A. A. Paze, N. Bennamane, B. Nedjar-Kolli,  K. Bachari, A. M. S. Silva

Synlett, 29 (2018) 1437–1440.

Key words chromones, ethanediamine, chromeno-imidazo-pyridinones, one-pot synthesis, tandem reaction, aza-Michael addition


 

SYNTHESIS AND RING TRANSFORMATION OF OXYGEN AND NITROGEN SPIRO BISHETEROCYCLES

  1. Talhi, D. C. G. A. Pinto, F. A. A Paz, M. Hamdi, A. M. S. Silva

 

Synlett, 26 (2015) 167–172.

 

Abstract: A facile and rapid access to bridgehead oxygen- and nitrogen-containing spiro bisheterocycles is reported. It involves a one-pot spiro-to-spiro ring transformation of the key spiro[chromanone-hydantoin] compounds into new substituted spiro [hydantoin-diazole], spiro [hydantoin-isoxazole], spiro [hydantoin-diazepine], spiro [hydantoinoxazepine], and spiro [hydantoin-benzodiazepine] upon reaction with appropriate bisnucleophilic agents. The hydantoin cycle is preserved during these chemical reactions affording the spiro bisheterocycles in
optimal yields (42–71%). This relevant spiro-to-spiro ring transformation was confirmed by NMR and single-crystal X-ray diffraction studies.

Key words spiro bisheterocycles, oxygen and nitrogen heterocycles, bisnucleophiles, NMR, X-ray diffraction

 

 

 

ORGANOBASE CATALYZED 1,4-CONJUGATE ADDITION OF 4-HYDROXYCOUMARINON CHALCONES: SYNTHESIS, NMR AND SINGLE-CRYSTAL X-RAY DIFFRACTIONSTUDIES OF NOVEL WARFARIN ANALOGUES

 

  1. Talhi, J. A. Fernandes, D. C.G.A. Pinto, F. A. A Paz, A. M.S. Silva

 

Journal of Molecular Structure 1094 (2015) 13-21.

 

Abstract: The synthesis of a new series of warfarin analogues by convenient organobase catalyzed 1,4-conjugate addition of 4-hydroxycoumarin to chalcone derivatives is described. 1H NMR spectroscopy evidenced
the presence of a predominant acyclic open-form together with the cyclic hemiketal tautomers of the
resulting Michael adducts. The acyclic open-form has been unequivocally proved by single-crystal
X-ray diffraction analysis. The use of the B ring ortho-hydroxychalcone synthons in this reaction has
led to a diastereoselective synthesis of warfarin bicyclo[3.3.1]nonane ketal derivatives

 

 

Keywords: Warfarin analogues,  Bicyclo[3.3.1]nonanes, 1,4-Conjugate addition,  Organobase catalysis, NMR, X-ray diffraction

 

A ONE-POT DIASTEREOSELECTIVE SYNTHESIS OF 2-[ARYL(HYDROXY)-METHYL]-6-METHYL2H-FURO[3,2-C]PYRAN-3,4-DIONES: CRYSTALLOGRAPHIC EVIDENCE FOR THE FURANONE RING CLOSURE

 

  1. Abdi, B. Boutemeur-Kheddis, M. Hamdi, O. Talhi, F.A. A Paz, G. Kirsch, A. M. S. Silva

 

Synlett, 26 (2015)  1749–1754.

 

Abstract: Novel furopyran-3,4-dione-fused heterocycles have been obtained by a one-pot reaction of α-brominated dehydroacetic acid and benzaldehydes under organobase conditions. The prepared 2-
[aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones were fully characterized by 2D NMR spectroscopy and supported by singlecrystal X-ray analysis to unequivocally prove the furan-3-one five-membered ring-closure mechanism instead of the dihydroflavanon-3-ol sixmembered cyclization which has recently been proposed in the literature.

 

Keywords furan-3-ones, pyran-2-ones, dehydroacetic acid, synthesis, organobase, 2NMRspectroscopy, single-crystal X-ray diffraction

 

 

ONE-POT SYNTHESIS OF NOVEL HIGHLY FUNCTIONALIZED FURAN-BASED POLYPHENOLICS

  1. L. C. Sousa, O. Talhi, D. H. A. Rocha, D. C. G. A. Pinto, F. A. A Paz, K. Bachari, G. Kirsch, A. M. S. Silva

 

Synlett,  26 (2015) 2724–2729.

 

Abstract: Novel, highly functionalized furan-based polyphenolics were prepared. The employed methodology involves a one-pot 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) catalyzed 1,4-conjugate addition of 1,3-dicarbonyl compounds on 3-bromochromones, furan heterocyclization, and chromanone ring opening.

 

Key words furan, polyphenols, 1,3-dicarbonyl compounds, 1,4-conjugate addition, ring transformation

 

 

MULTICOMPONENT SYNTHESIS OF 2[ARYL(ARYLAMINO)METHYL]FURO[3,2- C]PYRAN-3,4-DIONES AND DIASTEREOSELECTIVE FURAN RING OPENING TO (Z)-3-[3-ARYL-3-(ARYLAMINO)ACRYLOYL]-4-HYDROXYPYRAN-2-ONES

 

  1. Abdi, B. Boutemeur-Kheddis, M. Hamdi, O. Talhi,  K. Bachari,  G. Kirsch,  A. M. S. Silva

 

Synlett, 27 (2016)

 

Abstract: An efficient synthesis of novel 2-[aryl(arylamino)methyl]-6- methyl-4H-furo[3,2-c]pyran-3,4(2H)-diones is described by using a three-component reaction of α-bromodehydroaceticacid (α-Br-DHA) with anilines and benzaldehydes. Ammonium acetate is a suitable base to catalyse the diastereoselective tautomerism of the furo[3,2-c]pyran- 3,4-diones into (Z)-3-[3-aryl-3-(arylamino)acryloyl]-4-hydroxy-6-methyl-2H-pyran-2-ones by opening the furan ring. These latter compounds were also obtained by a three-component reaction (α-Br-DHA, anilines, benzaldehydes) catalysed by ammonium acetate.

Key words multicomponent reactions, furan-3-ones, pyran-2-ones, dehydroacetic acid, tautomerism

 

 

BIOLOGICAL ACTIVITIES AND PHENOLIC CONTENTS OF ARGANIA
SPINOSA L (SAPOTACEAE) LEAF EXTRACT

 

  1. Dakiche, M. Khali, A. K Abu-el-Haija, A. AlMaaytah and Q. A Al-Balas

 

Tropical Journal of Pharmaceutical Research, 15 (2016) 2563-2570.

 

Abstract: Purpose: To investigate the phenolic profile and biological activities of Argania spinosa L. leaves.
Methods: The crude methanol extract of leaves of A. spinosa L. Skeels was obtained by ultrasonic
extraction, and the total polyphenolic and flavonoid contents were determined by ultra-high performance
liquid chromatography-electrospray ionization-quadrupole time-of-flight-mass spectrometry (UPLC-ESIQTOF-MS). In vitro antioxidant activity was determined by 2,2-di-phenyl-1-picryl-hydrazil (DPPH) radical
assay and antimicrobial activity evaluated using agar disk diffusion method against reference
pathogenic strains (Bacillus subtilis ATCC 6633, Bacillus cereus ATCC 14579, Yersinia enterocolitica
ATCC 23715, Staphylococcus aureus ATCC 25923, Pseudomonas aeruginosa ATCC 27853,
Escherichia coli ATCC 25922). Cytotoxic activity was evaluated by methyl-thiazolyldiphenyl-tetrazolium
bromide (MTT) assay.

Results: The results revealed abundant polyphenols and flavonoids (221.39 ± 5.70 µg GAEq/1 g and
66.86 ± 3.36 µg CAEq/1 g, respectively) in the leaf extract. UPLC-DAD-ESI-QTOF-MS profiling showed
the presence of myrecitin-3-galactoside, myrecitin-3-gluctoside, myrecitin-3-xyloside, quercetin-3-
galactoside, quercetin-3-glucoside, quercetin-3-arabinofuranoside, and quercetin-3-rhamnoside. DPPH
assay of the leaf extract yielded a half-maximal effective concentration (EC50) value of 125.60 ± 1.87 µg.
A. spinosa L. leaves exhibited antibacterial activity against Gram (+) and Gram (-) bacteria, with
particularly marked activity against B. subtilis (inhibition zone, 16 mm). Cytotoxicity data showed that the
extract inhibited the proliferation of PC3 cells (IC50 ~ 600 µg).

Conclusion: A. spinosa L. leaf extract is rich in valuable biologically active compounds and could
represent a new resource for natural and preventive therapies.

 

Keywords: Argania spinosa, Polyphenols, Flavonoids, Antioxidant, Antibacterial, Cytotoxic

 

CATALYTIC ONE-POT DIASTEREOSELECTIVE MICHAEL-INITIATED RINGCLOSURE OF METHYL KETONES WITH 3-BROMOCHROMONES: SYNTHESIS OF CYCLOPROPA [B] CHROMANONES

 

  1. L. C. Sousa, O. Talhi, R. F. Mendes, F. A. A. Paz,
    K. Bachari, and A. M. S. Silva

 

Eur. J. Org. Chem, (2016) 3949–3958.

 

Abstract: A one-pot diastereoselective base-catalyzed Michaelinitiated ring-closure (MIRC) of activated methyl ketones with 3-bromochromones to give cyclopropa[b]chromanones is described. Three asymmetric centres are generated in the new cyclopropa[b]chromanone skeleton. Stereochemistry studies based on NMR spectroscopy and single-crystal X-ray diffraction analysis revealed the trans configuration of the cyclopropane ring, with the (1R,1aS,7aR)/(1S,1aR,7aS) pair of enantiomers, as was further confirmed by chiral HPLC. The use of acetone in our reaction produced a 1-acetyl-substituted cyclopropa[b]- chromanone that can undergo a subsequent MIRC reaction with a second molecule of 3-bromochromone to give the first described 1,1′-carbonylbis(cyclopropa[b]chromanone) dimmers as a meso form.

 

Keywords: Oxygen heterocycles · Cyclopropanes · Small ring systems · Fused-ring systems · Michael addition
Cyclization

 

 

ONE-POT SYNTHESIS OF BENZOPYRAN-4-ONES WITH CANCER
PREVENTIVE AND THERAPEUTIC POTENTIAL

 

  1. Talhi, L. Brodziak-Jarosz, J. Panning, B. Orlikova, C. Zwergel, T. Tzanova, S. Philippot, D. C. G. A. Pinto, F. A. A. Paz,  C. Gerhäuser, T. P. Dick, C. Jacob,  M. Diederich,  D. Bagrel,  G. Kirsch,  and A. M. S. Silva

 

Eur. J. Org. Chem, (2016)  965–975.

 

Abstract: A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of R1COCH2COR2 on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromone- and/or chromanone ring closure of the resulting Michael adducts when R1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones 3or (2.1– 3.1 μmol Trolox equiv./μmol compound in the DPPH assay). Chromanones 3p and 3r and 2-styrylchromone 3k were also most potent in inducing the cytoprotective Keap1-Nrf2 signalling pathway in a reporter gene assay (fivefold induction at concentrations <3 μM). Of the seven compounds evaluated for antiproliferative activities, 3k and 3r were the most active, inhibiting leukaemia K562 cell proliferation by 50 % after 72 h at concentrations of 4.5 and 7.9 μM, whereas normal peripheral blood mononuclear cells were not affected.

 

Keywords: Medicinal chemistry · Drug discovery · Anticancer agents · Oxygen heterocycles · Domino reactions · Michael addition · Antioxidants

 

 

DIBENZO [B, E][1,4]DIAZEPIN-1-ONES AND THEIR RING-OPENED DERIVATIVES: REVISITED SYNTHESIS, 2D NMR AND CRYSTAL STRUCTURE

 

  1. Cherfaoui, H. Lakhdari, N. Bennamane, R. Ameraoui, O. Talhi,  F. A. A. Paz,  K. Bachari,  G. Kirsch,  K. Nejar-Bellara,  A. M. S. Silva

 

Synlett, 28 (2017) 2247–2252.

 

Abstract : The synthesis of 2,3,4,5,10,11-hexahydro-1H-dibenzo[b,e][1,4]diazepin-1-ones was revisited and a catalyst-free method was established, by exploring the reactivity of 3-[(2-aminoaryl)amino]dimedones towards carbonylated electrophiles. 2D NMR and singlecrystal X-ray diffraction studies were used to characterize the structures unequivocally and to review the mechanism leading to the formation of supposed positional isomers. The action of 3-[(2-aminoaryl)amino]dimedones on chromene-3-carboxylic acid, fumaryl, and oxalyl chloride has led to dibenzo[b,e][1,4]diazepin-1-one ring opening to produce novel Z-configured enaminone and linear.  diamides.

Key words 3-[(2-aminoaryl) amino]dimedones, carbonylated electrophiles, dibenzo[b,e][1,4]diazepin-1-ones, reaction mechanism, 2D NMR, single-crystal X-ray diffraction

 

 

SYNTHETIC APPROACH TOWARD HETEROCYCLIC HYBRIDS OF                            [1, 2, 4] TRIAZOLO [3, 4-B][1,3,4]THIADIAZINES

 

  1. Lechani, M. Hamdi, B. Kheddis-Boutemeur,  O. Talhi,  Y. Laichi,  K. Bachari,  A. M. S. Silva

 

Synlett, 29 (2018) 1502–1504.

 

Abstract : The synthesis of novel heterocyclic [1,2,4]triazolo[3,4- b][1,3,4]thiadiazine hybrids by a bimolecular reaction of 2-(4-amino-5- mercapto-4H-[1,2,4]triazol-3-yl)phenol with an aromatic or heterocyclic α-bromoacetyl derivatives is described. This synthetic procedure starts from an unprotected phenol.

Key words triazolothiadiazines, triazolylphenol, bromomethyl ketones, polycycles, heterocycles, cyclization

 

 

CYTOSTATIC HYDROXYCOUMARIN OT52 INDUCES ER/GOLGI STRESS AND STAT3 INHIBITION TRIGGERING NON-CANONICAL CELL DEATH AND SYNERGY WITH BH3 MIMETICS IN LUNG CANCER

 

  1. Y. Lee, O. Talhi , D. Jang, C. Cerella, A. Gaigneaux, K.W Kim, J. W. Lee, M. Dicato, K. Bachari, B. Woo Han, A. M.S. Silva, B. Orlikova, M. Diederich

 

Cancer Letters, 416 (2018) 94-108.

 

Abstract: Coumarins are natural compounds with antioxidant, anti-inflammatory and anti-cancer potential known to modulate inflammatory pathways. Here, non-toxic biscoumarin OT52 strongly inhibited proliferation of non-small cell lung cancer cells with KRAS mutations, inhibited stem-like characteristics by reducing aldehyde dehydrogenase expression and abrogated spheroid formation capacity. This cytostatic effect was characterized by cell cycle arrest and onset of senescence concomitant with endoplasmic reticulum and Golgi stress, leading to metabolic alterations. Mechanistically, this cellular response was associated with the novel capacity of biscoumarin OT52 to inhibit STAT3 transactivation and expression of its target genes linked to proliferation. These results were validated by computational docking of OT52 to the STAT3 DNA-binding domain. Combination treatments of OT52 with subtoxic concentrations of Bcl-xL and Mcl-1-targeting BH3 protein inhibitors triggered synergistic immunogenic cell death validated in colony formation assays as well as in vivo by zebrafish xenografts.

 

Keywords: KRAS mutation, Non-small cell lung cancer, Coumarin, STAT3, BH3 mimetics, Immunogenic cell death

 

 

HYDROXYCOUMARIN OT-55 KILLS CML CELLS ALONE OR IN SYNERGY WITH IMATINIB OR SYNRIBO: INVOLVEMENT OF ER STRESS AND DAMP RELEASE

 

  1. Mazumder, J. Y. Lee, O. Talhi, C. Cerella, S. Chateauvieux, A. Gaigneaux, C. R. Hong, H. J. Kang, Y. Lee, K. W. Kim, D. W. Kim, H. Y. Shin, M. Dicato, K. Bachari, A.M.S. Silva, B. Orlikova-Boyer, M. Diederich

 

Cancer Letters, 438 (2018) 197–218.

 

Abstract: We synthetized and investigated the anti-leukemic potential of the novel cytostatic bis(4-hydroxycoumarin) derivative OT-55 which complied with the Lipinski’s rule of 5 and induced differential toxicity in various chronic myeloid leukemia (CML) cell models. OT-55 triggered ER stress leading to canonical, caspase-dependent apoptosis and release of danger associated molecular patterns. Consequently, OT-55 promoted phagocytosis of OT-55-treated CML cells by both murine and human monocyte-derived macrophages. Moreover, OT-55 inhibited tumor necrosis factor α-induced activation of nuclear factor-кB and produced synergistic effects when used in combination with imatinib to inhibit colony formation in vitro and Bcr-Abl+ patient blast xenograft growth in zebrafish. Furthermore, OT-55 synergized with omacetaxine in imatinib-resistant KBM-5 R cells to inhibit the expression of Mcl-1, triggering apoptosis. In imatinib-resistant K562 R cells, OT-55 triggered necrosis and blocked tumor formation in zebrafish in combination with omacetaxine.

 

Keywords: Eukaryotic initiation factor 2α, Calreticulin, High mobility group box 1, Phagocytosis

 

 

ONE-POT THREE-COMPONENT SYNTHESIS OF BISPYRAZOLE THIAZOLEPYRAN-2-ONE HETEROCYCLIC HYBRIDS

 

  1. Saidoun, L. Boukenna, Rachedi,  O. Talhi,  Y. Laichi,  N. Lemouari,  M. Trari,  K.  Bachari,  A. M. S. Silva

 

Synlett, 29 (2018)  1776–1780.

 

Abstract : A new series of some interesting bispyrazole-thiazole-pyran- 2-one heterocyclic hybrids has been efficiently synthesized via a onepot catalyst-free three-component reaction of α-bromoacetylated pyran-2-one derivatives, thiosemicarbazide, and polysubstituted-1-(1Hpyrazol-4-yl)butane-1,3-diones. This multicomponent procedure has been advantageously applied to prepare a structural diversity of heterocyclic hybrids characterized by extensive 1D and 2D NMR spectroscopic studies.

Key words pyrazoles, thiazoles, pyran-2-ones, chromen-2-ones, three-component synthesis, 1D an

 

SYNTHESIS, CHARACTERIZATION AND MOLECULAR MODELING OF BINUCLEAR PD (II) AND IR (IV) COMPLEXES WITH BIS [4-HYDROXY-6-METHYL-3-{(1E)-N-[2- (ETHYLAMINO) ETHYL]ETHANIMIDOYL}-2H-PYRAN-2-ONE]: APPLICATION TO DETECTION OF GLUCOSE

 

  1. Ait-Ramdane-Terbouche, A. Terbouche, M. Khalfaoui, C. L Douib, H. Lakhdari, D. Lerari, K. Bachari, D. Mezaoui, J. P Guegan, D. Hauchard

 

 

Journal of Molecular Structure 1170 (2018) 119-130.

 

Abstract: Two binuclear Pd (II) and Ir(IV) complexes with new bis [4-hydroxy-6-methyl-3-{(1E)-N-[2-(ethylamino) ethyl] ethanimidoyl}-2H-pyran-2-one] ligand (Schiff base: L) have been prepared and characterized by elemental analysis, ESI-MS, conductivity, NMR (1H NMR, 13C NMR, COSY-NMR, HMBC-NMR and HSQCNMR), EPR, FT-IR, ATR, UVeVisible spectra and cyclic voltammetry. Both antioxidant and antimicrobial activities were studied; the stability constants of the metal complexes and their interactions with glucose were estimated using spectrophotometric method. In addition, the detection of glucose using Pd(II) and Ir(IV) complexes was investigated using cavity microelectrode (CME) by chronoamperometric method. The characterization results and the molecular parameters were determined using DFT technique; a square planar geometry around Pd (II) and an octahedral geometry around Ir(IV) was found.
The antioxidant measurements showed that the ligand and its complexes exhibited remarkable activity, and the antimicrobial studies revealed that all compounds are biologically active for some bacteria and fungi. Electrochemical measurements showed the presence of sensitive responses towards glucose using
both Pd(II) and Ir(IV) complexes; these results were found to be higher than other materials around glucose concentration range of 0e4 mM.

 

Keywords: Schiff base, Pd (II) and Ir(IV) complexes, DFT, Stability constants, Biological activities, Chronoamperometric glucose detection

 

 

MICROWAVE – ULTRASOUND COMBINED REACTOR SUITABLE FOR ATMOSPHERIC SAMPLE PREPARATION PROCEDURE OF BIOLOGICAL AND CHEMICAL PRODUCTS

 

  1. Lagha, S. Chemat, P.V. Bartels and F. Chemat

 

Analysis, 27 (1999) 452-457.

 

Abstract: A compact apparatus in which a specific position can be irradiated by microwaves (MW) and ultrasound (US) simultaneously has been developed. The MW-US reactor has been designed for atmospheric pressure digestion and dissolution of biological and chemical products. The reactor can treat a range of throughputs of 0.1 to 10 grams of a liquid or solid sample. Its application in analytical chemistry has been shown by two examples where decreases in digestion and dissolution time were demonstrated: determination of copper in olive oil and dissolution of refractory mineral material Co3O4. Simultaneous microwave and ultrasound irradiation is shown as a new technique for atmospheric pressure digestion and dissolution of solid and liquid samples suitable for chemical and biological analysis.

 

Key words: Microwave, ultrasound, olive oil, mineral, digestion, dissolution.

 

ANTI-PROLIFERATIVE, CYTOTOXIC AND NF-ĸB INHIBITORY PROPERTIES OF SPIRO (LACTONE-CYCLOHEXANONE) COMPOUNDS IN HUMAN LEUKEMIA.

 

Mustapha M. Bouhenna, Barbora Orlikova, Oualid Talhi, Ben Schram, Diana c.g.a. Pinto, Nadia Taibi, Khaldoun Bachari, Marc Diederich, Artur M.S. Silva and Nabil Mameri

 

Anticancer Research, 37 (2017) 5225-5233

 

 Abstract: Background/Aim: NF-ĸB affects most aspects of cellular physiology. Deregulation of NF-ĸB signaling is associated with inflammatory diseases and cancer. In this study, we evaluated the cytotoxic and NF-ĸB inhibition potential of new spiro(lactone-cyclohexanone) compounds in two different human leukemia cell lines (U937 and K562). Materials and Methods: The anti-proliferative effects of the spiro(lactone cyclohexanone) compounds on human K562 and U937 cell lines was evaluated by trypan blue staining, as well as their involvement in NF-kB regulation were analyzed by luciferase reporter gene assay, Caspase-3/7 activities were evaluated to analyze apoptosis induction. Results: Both spiro(coumarin-cyclohexanone) 4 and spiro(6- methyllactonecyclohexanone) 9 down-regulated cancer cell viability and proliferation. Compound 4 inhibited TNF-α-induced NF-ĸB activation in a dose-dependent manner and induced caspasedependent apoptosis in both leukemia cell lines. Conclusion: Results show that compound 4 and compound 9 have potential
as anti-cancer agents. In addition, compound 4 exerted NFkB inhibition activity in leukemia cancer cells.

 

Key Words: Spiro (lactone-cyclohexanones), anti-cancer, cytotoxicity, anti-proliferation, nuclear factor-ĸB, apoptosis.

 

 

EFFECTS OF SPIRO-BISHETEROCYCLES ON PROLIFERATION AND APOPTOSIS IN HUMAN BREAST CANCER CELL LINES

 

  1. Hamdan Ramdani, O .Talhi, N. Taibi, L. Delort, C. Decombat, A. Silva, K. Bachari, M. P. Vasson and Florence Caldefie-Chezet

 

Anticancer Research, 36 (2016)  6399-6408

 

Abstract: Breast cancer is the leading cause of cancerrelated death in women worldwide and a critical public health concern. Here we investigated the anticancer potential and effects of low-molecular-weight bridgehead oxygen and nitrogen-containing spiro-bisheterocycles on proliferation and apoptosis of the human breast cancer cell lines MCF-7 and MDA-MB-231. The compounds feature a hydantoin moiety attached to either diazole, isoxazole, diazepine, oxazepine or benzodiazepine via the privileged tetrahedral spiro-linkage. Treatment with compounds spiro [hydantoin-isoxazole] and spiro [hydantoin-oxazepine] resulted in a dose-dependent decrease of cell proliferation and induction of apoptosis in both breast cancer cell lines, whereas spiro [hydantoin-diazepine] was only active against MDA-MB 231. Quantitative reverse transcription polymerase chain reaction analysis showed up-regulation of murine double minute 2 (MDM2), strictly p53-dependent, and detected an increase in expression of pro-apoptotic caspase 3 and BCL2-associated X (BAX) genes in both breast cancer cell lines expressing wild-type and mutant p53. In summary, the results suggest that our compounds promote apoptosis of breast cancer cell lines via p53-dependent and –independent pathways.

 

Key Words: Spiro-bisheterocycles, oxygen and nitrogen heterocycles, breast cancer, cell proliferation, apoptosis, p53, MDM2.

 

SYNTHESIS, MOLECULAR AND SOLID STATE STRUCTURE OF 5-(5-NITRO FURAN-2-YLMETHYLEN), 3-N– (2-METHOXY PHENYL),2-N’-(2-METHOXYPHENYL) IMINO THIAZOLIDIN-4-ONE: X-RAY POWDER DIFFRACTION AND DFT STUDIES

 

  1. Rahmani, A. Djafri, A. Chouaih, A. Djafri, F. Hamzaoui,
    R. Rizzi, A. Altomare

 

Journal of Molecular Structure/ Accepted

 

Abstract: The 5-(5-nitro furan-2-ylmethylen), 3-N-(2-methoxy phenyl), 2-N’-(2-methoxyphenyl) imino
thiazolidin-4-one compound has been synthesized and fully characterized by FT-IR, 1H and
13C NMR spectroscopy. The crystal structure of the title compound was investigated by X-ray
powder diffraction (XRPD). The obtained structure is triclinic, space group P-1, with a =
11.4746(3), b = 10.9106(2),c = 8.8083(2) Å, α = 103.6665(9)°β = 91.4910(13)° γ =
84.1433(12)°, V =1065.93(4)Å3 and Z = 2. The XRPD structural investigation has been
completed by a theoretical analysis performed using the density functional theory (DFT) via a
B3LYP functional at 6-311G(d,p) basis set. To highlight and establish the contribution of the
different intermolecular interactions, Hirshfeld surface analysis and fingerprint plots were
performed. The solid state molecular structure and packing are discussed.

 

Keywords: Molecular structure, Expo, thiazole, heterocycles, organic compounds

 

 

INVOLVEMENT OF NEUROLEPTIC DRUGS IN SELENIUM DEFICIENCY AND SUDDEN DEATH OF CARDIAC ORIGIN: STUDY AND HUMAN POST-MORTEM EXAMINATION

  1. Hamdan, M. Bost, G. Chazot, B. Bui-Xuan, F. Vaillant, L. Dehina , J. Descotes, A. Tabib, Z. Mamou, Q. Timour

 

Journal of Trace Elements in Medicine and Biology 26 (2012) 170–173.

 

Abstract: The involvement of psychotropic drugs in sudden deaths has been highlighted. The objective of this work was to establish a link between selenium levels in heart tissue, psychotropic treatment and sudden death. Selenium levels were measured by electrothermal atomic absorption spectroscopy post-mortem in heart, brain and liver. Histological examination evidenced dilated cardiomyopathy in 45% of cases, left ventricular hypertrophy in 36%, and ischemic coronaropathy in 18%. A significant reduction of myocardial selenium levels compared to controls was seen in patients treated with neuroleptic drugs or meprobamate. No changes in brain or liver selenium levels were seen. These results suggest that selenium deficiency can facilitate sudden death in patients on psychotropic drugs. The reduced activity of glutathione peroxidase due to selenium deficiency can result in augmented oxidative stress in myocardial cells and myocardiopathy leading to sudden death.

 

Keywords: Selenium Sudden death Psychotropic drugs Heart

 

 

PHYSICOCHEMICAL CHARACTERIZATION AND DETERMINATION OF CHLORAMPHENICOL RESIDUES AND HEAVY METALS IN ALGERIAN HONEYS

 

  1. Mehdi, A. Mutlaq & Q. Al-Balas & E. Azzi & L. Bouadjela & N. Taïbi & H. Dakiche & L. Touati & L. Boudriche & K. Bachari

 

Environmental Science and Pollution Research

 

Abstract: The concentration of certain heavy metals in various foods (fruits, cereals, legumes, and bee products) produced in industrial and urban cities is increasing each year following industrial development. Quality of honey and its contamination by different polluting agents are related essentially to its production environment, or it can arise from beekeeping practices. In the present study, the determination of physicochemical properties: moisture, pH, total acidity, electric conductivity, hydroxymethylfurfural (HMF), sugars, and chloramphenicol (CAP) residues; the metal content by determination of two toxic metals levels: lead (Pb) and cadmium
(Cd); and other trace elements: magnesium (Mg), iron (Fe), zinc (Zn), copper (Cu), and nickel (Ni) in 23 different honey samples collected from North regions of Algeria were investigated. The physicochemical properties and the metal contents were found within the ranges established by the international standards. For the antibiotic residues, only four honey samples are contaminated by CAP. Metals were found in non-significant values and are in safety baseline levels for human consumption except Mg which exceed the limits. These results suggested that honey could be used as an indicator to detect contaminating agents from the environment since
bees are excellent sentinels for assessing environmental contamination because of their physiological and biological characteristics.

 

Keywords: Honey. Contamination. Physicochemical properties . Heavy metals . Chloramphenicol residues . North Algeria

 

 

ALPHA CYANO-4-HYDROXY-3-METHOXYCINNAMIC ACID INHIBITS PROLIFERATION AND INDUCES APOPTOSIS IN HUMAN BREAST CANCER CELLS

 

  1. Hamdan, Z. Arrar, Y. Al Muataz, L. Suleiman, C. Ne´grier, J. K. Mulengi, H. Boukerche

 

PLOS ONE, 9 (2013) e72953

 

Abstract: This study investigated the underlying mechanism of 4-hydroxy-3-methoxycinnamic acid (ACCA), on the growth of breast cancer cells and normal immortal epithelial cells, and compared their cytotoxic effects responses. Treatment of breast cancer cells (MCF-7, T47D, and MDA-231) with ACCA resulted in dose- and time-dependent decrease of cell proliferation, viability in colony formation assay, and programmed cell death (apoptosis) with minimal effects on non-tumoral cells. The ability of ACCA to suppress growth in cancer cells not expressing or containing defects in p53 gene indicates a lack of involvement of this critical tumor suppressor element in mediating ACCA-induced growth inhibition. Induction of apoptosis correlated with an increase in Bax protein, an established inducer of programmed cell death, and the ratio of Bax to Bcl-2, an established inhibitor of apoptosis. We also documented the ability of ACCA to inhibit the migration and invasion of MDA- 231 cells with ACCA in vitro. Additionally, tumor growth of MDA-231 breast cancer cells in vivo was dramatically affected with ACCA. On the basis of its selective anticancer inhibitory activity on tumor cells, ACCA may represent a promising therapeutic drug that should be further evaluated as a chemotherapeutic agent for human breast cancer.

 

 

STUDY OF THE DEGRADATION IN AQUEOUS SOLUTION OF A REFRACTORY ORGANIC COMPOUND: AVERMECTIN TYPE USED AS PESTICIDE IN AGRICULTURE

 

  1. Boukhrissa, F. Ferrag-Siagh, L. M. Rouidi, S. Chemat and H. Aït-Amar

 

Water Science & Technology, (2017)   76-78

 

Abstract: We examined the removal of abamectin by the electro-Fenton (EF) process and the feasibility of
biological treatment after degradation. The effect of the operating parameters showed that
abamectin (Aba) degradation was enhanced with increasing temperature. Response surface analysis
of the central composite design led to the following optimal conditions for the abatement of
chemical oxygen demand: 45.5 WC, 5 mg L1, 150 mA, and 0.15 mmol L1 for the temperature, initial
Aba concentration, current intensity, and catalyst concentration, respectively. Under these
conditions, 68.01% of the organic matter was removed and 94% of Aba was degraded after 5 h and
20 min of electrolysis, respectively. A biodegradability test, which was performed on a solution
electrolyzed at 47 WC, 9 mg L1, 150 mA, and 0.15 mmol L1, confirms that the ratio of biological
oxygen demand/chemical oxygen demand increased appreciably from 0.0584 to 0.64 after 5 h of
electrolysis. This increased ratio is slightly above the limit of biodegradability (0.4). These results
show the relevance of the EF process and its effectiveness for abamectin degradation. We conclude
that biological treatment can be combined with the EF process for total mineralization.

 

Key words | abamectin, advanced oxidation process, central composite design, electrochemical degradation, electro-Fenton process, optimization

 

ISOLATION OF BERBERINE TANNATE USING A CHROMATOGRAPHY ACTIVITY-GUIDED FRACTIONATION FROM ROOT BARK OF BERBERIS HISPANICA BOISS. & REUT.

 

 

  1. Aribi,   Chemat, Y. Hamdi-Pacha & W. Luyten

 

Journal of Liquid Chromatography & Related Technologies, 17 (2017) 894–899.

 

Abstract: Root bark of Berberis hispanica Boiss. & Reut. constitutes an important source of alkaloids and is traditionally used in Algeria and Morocco in many herbal formulations particularly for the treatment of stomach infections and colon cancer. Activity-guided fractionation of Berberis extract is developed by step-gradient elution on column chromatography followed by preparative HPLC to isolate the most antistaphylococcal compound. Solvent extraction-activity screening indicates that ethanol should be used as the extracting solvent as it has exhibited the highest activity against Staphylococcus aureus(Rosenbach ATCC6538) followed by water extract, whereas no activity is recorded for acetone and hexane extracts. Screening of collected fractions from chromatographic separations indicates that the fraction presenting the highest antistaphylococcal activity is identified as berberine tannate by UV spectrum, melting point measurement and confirmed by liquid chromatography coupled to mass spectrometry (LC/MS). The minimal inhibition concentration value of berberine tannate against S. aureus is evaluated at 5 µg mL 1.

 

Keywords: Berberine; Berberis hispanica Boiss. & Reut.; bioassayguided fractionation; chromatography; Staphylococcus aureus

 

DIASTEREOSELECTIVE ONE-POT TANDEM SYNTHESIS OF CHROMENOPYRIDODIAZEPINONES THROUGH 1, 4- AND 1,6-AZA-CONJUGATE ADDITIONS/HETEROCYCLIZATIONS

 

  1. Bouchama, R. Hassaine, O. Talhi, N. Taibi, R. F. Mendes,  F. A. A. Paz,  K. Bachari,  A. M. S. Silva

 

 Synlett, 29 (2018) 885-889.

 

Abstract : We report an efficient one-pot synthesis of a novel series of chromenopyridodiazepinone polyheterocycles by a catalyst-free nucleophilic addition of ethane-1,2-diamine to (E,E)-3-[3-(2-hydroxyphenyl)- 3-oxoprop-1-en-1-yl]-2-styrylchromones at room temperature under mild conditions. The reaction proceeds by a tandem process involving 1,4- and 1,6-aza-conjugate additions of one amino group of ethane- 1,2-diamine to the α,β-unsaturated (3-oxoprop-1-en-1-yl) and the α,β,γ,δ-diunsaturated (2-styrylchromone) carbonyl system of the precursor, followed by imine condensation of the remaining amino group to generate the chromenopyridodiazepinone polyheterocycle. All compounds were characterized by means of one- and two-dimensional NMR spectroscopy and single-crystal X-ray crystallography.

Key words styrylchromones, ethanediamine, chromenopyridodiazepinones, one-pot synthesis, tandem reaction, aza-conjugated addition

 

 

ORGANOBASE CATALYSED ONE-POT EXO-SELECTIVE SYNTHESIS OF MESO-SPIRO [CYCLOHEXANONE-PYRANDIONE] DERIVATIVES

 

 

  1. Talhi, H. Abdeldjebar,Y. Belmiloud, R. Hassaine, N. Taibi, M. Va´lega, F. A. A. Paz, M. Brahimi, K. Bachari and A. M. S. Silva

 

  1. Chem DOI: 10.1039/c7nj02168b

 

Abstract: An exo-selective one-pot synthesis of novel spiro[cyclohexanone-pyrandione] derivatives through two sequential organobase-catalysed 1,4-conjugate additions of pyran-2,4-dione precursors on diarylideneacetone derivatives is described. The resulting 7,11-diaryl-2-oxaspiro[5.5]undec-3-ene-1,5,9- triones were obtained as a 2 : 1 mixture of exo- and endo-diastereomers and adopt a meso-form due to the bilateral symmetry existing in the scaffold. Chiral-HPLC, NMR and single-crystal X-ray diffraction (including synchrotron data) have been used to elucidate the spiro[cyclohexanone-pyrandione] structure, showing therefore the exo/endo-diastereomers obtained in a meso-form, the cis-7,11-diaryl configuration (equatorial position) and different conformational changes in the cyclohexanone skeleton both in liquid and solid states. DFT studies proved the exo-stereoselectivity of the reaction by determining the exo/cis equatorial–equatorial configuration as the most thermodynamically stable form of our spiro[cyclohexanone-pyrandione] skeleton, while the structural substitution has no effect.

 

 

 

 

COBALT CONTAINING MICROPOROUS ALUMINOHOSPHATES AS NEW PHOTOCATALYST FOR HYDROGEN GENERATION UNDER VISIBLE IRRADIATION

 

H Hentit, A. Boudjemaa, A. Bouchama, J.C. Jumas, K. Bachari, M.S Ouali

 

Materials Research Bulletin 10063

 

Abstract :

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

CONTRIBUTION OF MICROWAVES OR ULTRASONICS ON CARVONE AND LIMONENE RECOVERY FROM DILL FRUITS (ANETHUM GRAVEOLENS L.)

 

  1. Chemat, E. D.C. Esveld

 

Innovative Food Science and Emerging Technologies, 17 (2013) 114–119.

 

Abstract: The objective of this study is to investigate alternative preparation techniques such as microwave and ultrasound for the recovery and evaluation of carvone and limonene from flaked dill fruits (Anethum graveolens L.). The study indicates that microwave-assisted extraction using hexane is highly recommended to reveal the correct amount of carvone and limonene in dill fruits. In this respect, when hexane is used, microwave-assisted system gives a better carvone yield of 29.96 mg/g compared to 24.54 and 23.49 mg/g for ultrasound and maceration (control) methods respectively. Furthermore, systems using hexane are able to recover high amount of limonene as opposite to systems using water where extracts are characterised by an absence of
free fatty acids and a high abundance of carvone translated by high carvone/limonene ratio especially in microwaves (22.88) and ultrasound (6.55). These findings suggest that the intervention of microwaves or ultrasonics enhances extraction selectivity for carvone but have no great effect on limonene recovery.
Although the recovered quantity of carvone in water extracts is much lower than the system using hexane due to low solubility of carvone in water, the advantages of using a GRAS solvent such as water are evident. It allows extracts to be readily available for spray application on potatoes’ storage. In addition, the proposed enhancement involving ultrasound pre-treatment has helped in increasing carvone yield and has the advantage to be easily implemented on existing extraction processes. Industrial relevance: Our study shows that new technologies such as ultrasound and microwaves offer important advantages over conventional methods, such as shorter extraction time, energy saving and selectivity. Furthermore, the pretreatment of samples with ultrasound stands an intelligent tool to enhance extraction yields without jeopardising selectivity. Those aspects are of primary importance for industry to reduce cost and bring greener routes to their established processes. In another aspect, the application of the proposed tandem method involving ultrasonics and water as a solvent would contribute to the creation of a niche market for hydrocarbon-free products, which are very sought after from exigent clients. In addition, the results indicate also that water gives valuable advantages in terms of safety, cleanliness and adoption if we decide to generalise its use at an industry scale for carvone recovery. On top of that, using water as solvent in microwaves or ultrasound systems produces extracts rich in carvone, offering a product that may be used on potato storage on products for example having Bio or Organic labels without hindering their stringent regulations. Furthermore, the use of the produced carvone directly as a spray would not influence the perception of people as carvone represents also the major compound on the widely used condiment Carum carvi L.

 

Keywords: Dill Carvone Limonene Extraction composition SDE Microwaves Ultrasound

 

 

 

 

 

 

 

 

 

 

 

 

 

 

COPOLYMERIZATION OF Ε-CAPROLACTONE WITHTETRAHYDROFURAN BY A SOLID ACID, IN PRESENCE OF ACETIC ANHYDRIDE

 

  1. Bouchama, M .I. Ferrahi, M. Belbachir

 

  1. Mater. Environ. Sci, 6 (2015) 977-982.

 

Abstract: Maghnite is a montmorillonite sheet silicate clay that is exchanged with protons to produce Maghnite-H+ (MagH+). This non-toxic and cheaper cationic catalyst was used for the copolymerization of ε-caprolactone (CL) with tetrahydrofuran (THF), in presence of acetic anhydride (AA). The effects of the amounts of Mag-H+, acetic anhydride and the temperature on the synthesis of poly (ε-caprolactone-co-tetrahydrofuran) were studied. The copolymer obtained was characterized by 1H-NMR and IR spectroscopy.

 

Keywords: Maghnite; Montmorillonite; Tetrahydrofuran; epsilon-caprolacton; Ring opening polymerization

 

 

SCREENING OF NEW SOLVENTS FOR ARTEMISININ EXTRACTION PROCESS USING AB INITIO METHODOLOGY

 

  1. Lapkin, M. Peters, L. Greiner, S. Chemat, K. Leonhard, M. A. Liauw and W. Leitner

 

Green Chem, 12 (2010) 241–251.

 

Abstract : The solubility of artemisinin in a range of conventional and novel solvents was evaluated using the COSMO-RS approach, and verified experimentally as well as against literature data. The computational method was improved by calibrating against a limited set of experimental data, enhancing the accuracy of the calculations. The optimised method was shown to be in reasonable agreement with experimental data; however, lack of reliable experimental data is identified as an issue. Several novel solvents perceived as green alternatives to conventional solvents were targeted and shown to offer good solubility of artemisinin. Extraction from Artemisia annua by carbonate solvents was experimentally verified

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

INTEGRATING MEDICINAL PLANTS EXTRACTION INTO A HIGH-VALUE BIOREFINERY: AN EXAMPLE OF ARTEMISIA ANNUA L.

 

  1. Lapkin, E. Adou , B. N. Mlambo, Chemat , J. Suberu , A. E.C. Collis, A. Clark, G. Barker

 

  1. R. Chimie, 17 (2014) 232–241.

 

Abstract: A principle of biorefining is extended to medicinal plants with the view of developing a more sustainable business model for biomass producers and extractors. This is demonstrated for Artemisia annua L. currently cultivated or harvested in the wild for extraction of a single compound, artemisinin, comprising on average 1 wt% dry weight of the plant biomass. We scaled extraction of artemisinin by a non-toxic to bacterial fermentation solvent tetrafluoroethane to a 5 L pilot scale. We identified a number of cometabolites that could be extracted from the plant along with artemisinin and describe the multi-step extraction-fractionation sequence that potentially could be transferred to a large-scale multi-step extraction process. We also show possible routes to higher-value compounds on the basis of A. annua secondary metabolites, exemplified by the conversion of flavonoids to monomers.

 

Keywords: Biorefinery High-value biorefinery Artemisia annua Artemisinin Hydrofluorocarbons Extraction Bio-pharmaceuticals

 

 

COMPOSITION AND MICROBIAL ACTIVITY OF THYME (THYMUS
ALGERIENSIS GENUINUS) ESSENTIAL OIL

 

 

  1. Chemat, R. Cherfouh, B. Y. Meklati & K. Belanteur

 

The Journal of Essential Oil Research, 24 (2012), 5–11

 

 

Abstract: In this study, the essential oil composition of Thymus algeriensis genuinus from Algeria was characterised by gas chromatography with flame ionization detector (GC/FID) and confirmed by gas chromatography coupled to mass spectrometry (GC/MS). The combination of GC/FID and GC/MS has resulted in the identification of 48 compounds then classified into four classes: monoterpene hydrocarbons, oxygenated monoterpenes, sesquiterpene hydrocarbons and oxygenated sesquiterpenes. The essential oil obtained by hydrodistillation is characterized by a rich content of phenolic compounds such as thymol (71%) and carvacrol (4%) versus a minor presence of monoterperne hydrocarbons like p-cymene (3%) and c-terpinene (0.5%). Furthermore, extraction kinetic study has revealed the effect of conservation period on oil yield and extraction rate especially during the first thirty minutes. As a consequence, we would argue that high moisture content in fresh plant material would produce a high oil yield in a reduced processing time and that reduced conservation period would prevent loss of volatiles before processing. Finally, the antimicrobial and antifungal activities were evaluated using the disc diffusion method. The extracted essential oil has presented a high inhibiting activity against eight bacterial strains up to 75 mm and two species of fungus up to 45 mm.

Keywords: Thymus algeriensis genuinus; essential oil; thymol; conservation

 

RAPID EXTRACTION OF VOLATILE COMPOUNDS USING A NEW SIMULTANEOUS MICROWAVE DISTILLATION: SOLVENT EXTRACTION DEVICE

 

  1. A. Ferhat, N. Tigrine-Kordjani, S. Chemat1, B. Y. Meklati, F. Chemat

 

Chromatographia, 65 (2007).

 

Abstract: Simultaneous distillation–extraction (SDE) is routinely used by analysts for sample preparation prior to gas chromatography analysis. In this work, a new process design and operation for microwave assisted simultaneous distillation–solvent extraction (MW-SDE) of volatile compounds was developed. Using the proposed method, isolation, extraction and concentration of volatile compounds can be carried out in a single step. To demonstrate its feasibility, MW-SDE was compared with the conventional technique, SDE, for gas chromatography-mass spectrometry (GC-MS) analysis of volatile compounds in a fresh aromatic herb, Zygophyllum album L., a wild salty desert herb belonging to the family Zygophyllaceae. SDE method required a long time (3 h) to isolate the volatile compounds, and large amounts of organic solvent (200 mL of hexane) for further extraction, while MW-SDE needed shorter time (only 30 min) to prepare the sample, and less amount of organic solvent (10 mL of hexane). These results show that MW-SDE–GC-MS is a simple, rapid and solvent-less method for the determination of volatile compounds from aromatic plants.

 

Keywords : Gas chromatography-mass spectrometry Microwave extraction Simultaneous distillation extraction Volatile compounds Zygophyllum album L.

 

 

MICROWAVE-ASSISTED EXTRACTION KINETICS OF TERPENES FROM CARAWAY SEEDS

 

  1. Chemat, H. A¨ıt-Amar, A. Lagha, D.C. Esveld

 

Chemical Engineering and Processing, 44 (2005) 1320–1326.

 

Abstract: The process conditions during the extraction of carvone and limonene from caraway seed (Carum carvi L.) with microwave-assisted extraction have been studied with respect to microwave power, radiation dose and extraction time in order to obtain the secondary metabolites selectively. Using classical solid–liquid extraction, limonene, carvone and fatty oils in both the raw material and the residual matrix material were extracted. Yields of limonene, carvone and total oil (C16, C18) were determined by GC and GC/MS analysis for both extracts. The effects of microwaves on cell walls and cells destruction could be seen on SEM micrographs.

 

Keywords: Extraction; Caraway seed; Carum carvi L.; Carvone; Limonene; Microwave; Soxhlet

 

 

 

 

 

 

 

 

THE EFFECT OF O-METHYLATED FLAVONOIDS AND OTHER CO-METABOLITES ON THE CRYSTALLIZATION AND PURIFICATION OF ARTEMISININ

 

  1. O. Suberu, P. Yamin, K. Leonhard, L. Song, S. Chemat, N. Sullivan, G. Barker, A. A. Lapkin

 

Journal of Biotechnology, 171 (2014) 25–33.

 

Abstract: Methoxylated flavonoids casticin, artemetin and retusin were identified as putative causative factors for low crystallization yields of artemisinin from extracts. Comparative profiling of biomass grown in different countries found elevated levels (∼60% higher) of artemetin in the East African biomass, which also demonstrates poor crystallization yields. The single compound and the combined doping experiments at 0, 25 and 50 g mL-1 doping levels showed that artemetin (at 50 g mL-1) caused a reduction in the amount of artemisinin crystallized by ca. 60%. A combination of the three flavonoids at 50 g mL-1 almost completely inhibited crystallization, reducing the yield by 98%. Treatment of extracts by adsorbents efficiently resolves the problem of low crystallization yield.

 

Keywords: Artemisinin Crystallization Bioseparations Biopharmaceuticals

 

 

EFFECT OF BARLEY SUPPLEMENTATION ON BOTH PUBERTAL AGE AND METABOLIC PROFILE OF D’MAN LAMBS LIVING IN A HOSTILE ENVIRONMENT

  1. Taïbi, N. Boukenaoui, A. Kahal, Z. Amirat & F. Khammar

Journal of Agriculture and Environmental Sciences, 4 (2015) 60-69.

Keywords: arid area, sheep, supplementation, metabolism, puberty


 

ACTIONS OF BISNUCLEOPHILES ON (E)-3-[3-(2-HYDROXYARYL)-3-OXOPROP- 1-EN-1-YL] CHROMONES: VERSATILE TRANSFORMATIONS INTO OXYGEN- AND NITROGEN-CONTAINING HETEROCYCLES

  1. Hassaine, O. Talhi, N. Taibi, F. A A. Paz, Okkacha Bensaid, K. Bachari,  A. M. S. Silva

Synlett, 27 (2016) 465–470.

Key words chromones, α,β-unsaturated carbonyl systems, Michael additions, bisnucleophiles, X-ray diffraction, heterocycles, 2D NMR

DEVELOPMENT OF HPLC ANALYTICAL PROTOCOLS FOR QUANTIFICATION
OF ARTEMISININ IN BIOMASS AND EXTRACTS

  1. A. Lapkin, A. Walker, N. Sullivan, B. Khambay, B. Mlambo, S. Chemat

Journal of Pharmaceutical and Biomedical Analysis, 49 (2009) 908–915.

Keywords: Artemisinin Artemisia annua HPLC-ELSD Refractive index (RI) Natural products Extraction Malaria


 

EFFICIENT SOLVENT SELECTION APPROACH FOR HIGH SOLUBILITY OF ACTIVE PHYTOCHEMICALS: APPLICATION FOR THE EXTRACTION OF AN ANTIMALARIAL COMPOUND FROM MEDICINAL PLANTS

  1. Laboukhi-Khorsi, K. Daoud, and S. Chemat

ACS Sustainable Chem. Eng, 5 (2017) 4332-4339.

Keywords: Solubility, Artemisinin, Extraction, Green solvent, Process development, Active compound


 

SONO-OXYDATION TREATMENT OF HUMIC SUBSTANCES IN DRINKING WATER

  1. Chemat, P.G.M Teunissen, S. Chemat, P.V Bartels

Ultrasonic Sonochemistry, 8 (2001) 247-250.  


 

SYNTHESIS, SPECTRAL CHARACTERIZATION, MOLECULAR MODELING, ANTIBACTERIAL AND ANTIOXIDANT ACTIVITIES AND STABILITY STUDY OF BINUCLEAR PD (II) AND RU(III) COMPLEXES WITH NOVEL BIS- [1-(2-[(2-HYDROXYNAPHTHALEN-1-YL)METHYLIDENE]AMINO}ETHYL)-1-ETHYL-3-PHENYLTHIOUREA] LIGAND: APPLICATION TO DETECTION OF CHOLESTEROL

Achour Terbouche, Chafia Ait-Ramdane-Terbouche, Zineb Bendjilali, Hafida Berriah,
Houria Lakhdari, Djahida Lerari, Khaldoun Bachari, Djillali Mezaoui, Nour El Houda
Bensiradj, Jean-Paul Guegan, Didier Hauchard

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 205 (2018) 146-159.

Keywords: Schiff base, complexes of platinum group metals, stability constants, biological
activities, fluorometric cholesterol sensor


ULTRASOUND-ASSISTED AROMATISATION WITH CONDIMENTS
AS AN ENABLING TECHNIQUE FOR OLIVE OIL FLAVOURING
AND SHELF LIFE ENHANCEMENT

 

  1. Assami & S. Chemat & B. Y. Meklati & F. Chemat

Food Anal. Methods, 9 (2016) 982–990.

Keywords Ultrasound .Flavouring .Oliveoil .CarumcarviL. Oxidative stability . Shelf life


 

EXTRACTION MECHANISM OF ULTRASOUND ASSISTED EXTRACTION AND ITS EFFECT ON HIGHER YIELDING AND PURITY OF ARTEMISININ CRYSTALS FROM ARTEMISIA ANNUA L. LEAVES

  1. Chemat, A. Aissa, A. Boumechhour, O. Arous, H. Ait-Amar

Ultrasonics Sonochemistry, 34 (2017) 310–316.

Keywords: Ultrasound Artemisinin Extraction Diffusion coefficient Purification Crystallisation


 

COMPARISON OF CONVENTIONAL AND ULTRASOUND-ASSISTED EXTRACTION OF CARVONE AND LIMONENE FROM CARAWAY SEEDS

  1. Chemat, A. Lagha, H. AitAmar, P. V. Bartels and F. Chemat

Flavour Fragr. J, 19 (2004) 188–195.

Key words: extraction; caraway seed; Carum carvi L.; carvone; limonene; ultrasound; Soxhlet


 

ULTRASOUND ASSISTED MICROWAVE DIGESTION

  1. Chemat, A. Lagha, H. Ait Amar, F. Chemat

Ultrasonics Sonochemistry, 11 (2004) 5–8.

Keywords: Microwave; Ultrasound; Digestion; Food; Analytical chemistry


 

ULTRASOUND INDUCED INTENSIFICATION AND SELECTIVE EXTRACTION OF ESSENTIAL OIL FROM CARUM CARVI L. SEEDS

  1. Assami, D. Pingret, S. Chemat, B. Y. Meklati, F. Chemat

Chemical Engineering and Processing, 62 (2012) 99–105.

Keywords: Carum carvi L. Carvone Essential oil Hydrodistillation Limonene Ultrasound


 

PROFILING POLYPHENOL COMPOSITION BY HPLC-DAD-ESI/MS AND THE ANTIBACTERIAL ACTIVITY OF INFUSION PREPARATIONS OBTAINED FROM FOUR MEDICINAL PLANTS

  1. E.C. Ziani, Lillian Barros, A. Z. Boumehira, K. Bachari, S. A. Helena, M. Jose Alves and I.C.F.R. Ferreira

Food Funct, 9 (2018) 149-159.


 

PROTECTIVE POTENTIAL OF OPUNTIA MICRODAYS FLOWER DECOCTION ON FRUCTOSE-ALLOXAN-INDUCED DIABETIC RATS ON KIDNEY AND PANCRES: CHEMICAL AND IMMUNOHISTOCHEMICAL ANALYSES

 

  1. Chahdoura, A. Khlifi, J. Ben Lamine, B.E.C. Ziani, K. Adouni, S. El Bok, Z. Haouas, F. Neffati, A. Zakhama, G. Flamini, L. Achour

Environemental Sience and Pollution Research, https://doi.org/10.1007/s11356-018-3290-6

Keywords:  Opuntia microdasys Lehm . Diabetes. Renal and pancreatic markers . Antioxidant system . Histopathology . Immunohistology


 

PHENOLIC COMPOUNDS CHARACTERISATION BY LC-DAD-ESI/MS AND BIOACTIVE PROPERTIES OF THYMUS ALGERIENSIS BOISS & Reut. AND EPHEDRA ALATA DECNE

 

 

B.E.C.Ziani, S. A. Heleno, K. Bachari, M. I. Dias, M. J. Alves, L. Barros, I.F.R Ferreira

 

 

Food Research International, DOI: 10.1016/j.foodres.2018.08.041

Keywords: Phenolic profile/bioactivities; Thymus algeriensis; Ephedra alata; Infusion/decoction/hydroethanolic extract


 

ECO-FRIENDLY ACCESS TO Β-KETOAMIDES: ONE-STEP CATALYST-AND SOLVENT-FREE AMIDATION OF Β-KETOESTERS UNDER MICROWAVE IRRADIATION

  1. Dechira, A. Taleb, A. Benmaati, S. Hacini and H. H. Zahmani

Oriental Journal Of Chemistry, 34 (2018) 152-160.

Keywords: Amidation, β-ketoesters, β-ketoamides, Catalyst-free, Solvent-free, Microwave irradiation.

 


 

GREEN AND HIGHLY EFFICIENT ONE-POT SYNTHESIS OF 1, 8-DIOXOOCTAHYDROXANTHENE DERIVATIVES USING TRIETHYLAMINE AS AN EFFICIENT CATALYST

  1. Naouri; A. Djemoui; M. B. Lahrech; S. Rahmani and M. R. Ouahrani

Heterocyclic Letter, 7 (2017) 589-597.

Keywords : One-pot synthesis; 1, 8-Dioxo-octahydroxanthene; Triethylamine (TEA); 1,3-
Cyclo- hexanedione; Knoevenagel condensation; Michael addition.


 

ONE-POT THREE-COMPONENT SYNTHESIS OF CHROMENO[4,3-D]PYRIMIDINONE DERIVATIVES

  1. Djemoui, M. Leguil, L. Souli, A. Naouri and M. B. Lahrech

Der Pharma Chemica, 7 (2015) 340-345.

Keywords: Chromeno [4,3-d]pyrimidine-6-one, Multi component reactions, 2-Aminobenzimidazole, 1,3-
Dicarbonyl compounds.


 

CUCO3–CUO NANOCOMPOSITE AS A NOVEL AND ENVIRONMENTALLY FRIENDLY CATALYST FOR TRIAZOLE SYNTHESIS

  1. Hadj Mokhtar, B. Boukoussa, R. Hamacha, A. Bengueddachc and D. El Abeda

RSC Adv, 5 (2015) 93438. 


 

EFFECT OF THE NI/AL RATIO OF HYDROTALCITE-TYPE CATALYSTS ON THEIR PERFORMANCE IN THE METHANE DRY REFORMING PROCESS 

  1. Touahra, M. Sehailia, W. Ketir, K. Bachari. Chebout, M. Trari, O . Cherifi, D. Halliche

Appl Petrochem Res, 6  (2016) 1–13.

Keywords: Dry reforming of methane Hydrotalcite-like compound Nickel Hydrogen


 

ENHANCED CATALYTIC BEHAVIOUR OF SURFACE DISPERSED NICKEL ON LACUO3 PEROVSKITE IN THE PRODUCTION OF SYNGAS: AN EXPEDIENT APPROACH TO CARBON RESISTANCE DURING CO2 REFORMING OF METHANE

  1. Touahra, A. Rabahi, R. Chebout, A. Boudjemaa, D. Lerari, M. Sehailia, D. Halliche, K. Bachari

International Journal of Hydrogen Energy, 41 (2016) 2477-2486.

Keywords: Syngas Perovskite Solegel method Impregnation Methane dry reforming

 


 

(MNO/MN3O4)-NIAL NANOPARTICLES AS SMART CARBON RESISTANT CATALYSTS FOR THE PRODUCTION OF SYNGAS BY MEANS OF CO2 REFORMING OF METHANE: ADVOCATING THE ROLE OF CONCURRENT CARBOTHERMIC REDOX LOOPING IN THE ELIMINATION OF COKE

  1. Touahra, M. Sehailia, D. Halliche, K. Bachari, A. Saadi, O. Cherifi

International Journal of Hydrogen Energy, 41 (2016) 21140-21156.

Keywords: CO2 reforming of methane Carbothermic reduction Redox looping Mn oxides


 

THIEME CHEMISTRY JOURNAL AWARDEES – WHERE ARE THEY NOW?
APPROACHES TO TAGETITOXIN AND ITS DECARBOXY ANALOGUE FROM D-GLUCOSE

  1. R. H. Plet, A.K. Sandhu, M. Sehailia, M. J. Porter

Synlett, 20 (2009) 3258-3262.

Key words: carbohydrates, natural products, stereoselective synthesis, alkynes, organometallic reagents 


 

EFFECT OF DIET ON MILK PRODUCTION AND FATTY ACIDS COMPOSITION OF COW MILK IN ALGERIA

  1. Meribai, A. Nouani, F. Boumediene, A. Kouidri, Sehailia,S. Chemat, M.M. Bellal

WULFENIA Journal, 22 (2015) 293-304.

Keywords: Dairy cows, feed, milk, fatty acids.


 

CHROMIUM (VI) PHOTO-REDUCTION UNDER VISIBLE AND SUNLIGHT IRRADIATION OVER BISMUTH-FERRITES BI2FE4O9 PHOTO-CATALYST

  1. Kebir, A. Boudjemaa, Y. Azoudj, M. Sehailia and K. Bachari

 

The Canadian Journal of Chemical Engineering, 96 (2018) 2292-2298.

Keywords: photo-reduction, Cr(VI), solar irradiation, visible light, Bi2Fe4O9


 

EFFICIENT BIOSORPTION OF METHYLENE BLUE, MALACHITE GREEN AND METHYL VIOLET ORGANIC POLLUTANTS ON BIOMASS DERIVED FROM ANETHUM GRAVEOLENS: AN ECOBENIGN APPROACH FOR WASTEWATER TREATMENT

  1. Hamitouche, M. Haffas, A. Boudjemaa, S. Benammar, Sehailia, K. Bachari

Desalin. Water Treat,  5 (2017) 225-236.

Keywords: Anethum graveolens; Biosorption; Cationic dyes; Isotherm models; Kinetic models


 

REMOVAL OF METHYL VIOLET DYE BY A LOW-COST WASTE (AJUGA PSEUDO-IVA): KINETIC AND EQUILIBRIUM ISOTHERM STUDY

  1. Behloul, A. Hamitouche, M. Haffas1, A. Boudjemaa, S. Benammar, M. Sehailia, T.
    Meziane, K. Bachari

 

The Canadian Journal of Chemical Engineering, 96 (2018) 2282-2291

Keywords: biosorption, dye removal, isotherm, kinetic, Ajuga pseudo-Iva waste


 

IN-SITU HYDROGASIFICATION/REGENERATION OF NIAL-HYDROTALCITE DERIVED CATALYST IN THE REACTION OF CO2 REFORMING OF METHANE: A VERSATILE APPROACH TO CATALYST RECYCLING 

  1. Abdelsadek, M. Sehailia, D. Halliche, V.M. Gonzalez-Delacruz, J.P. Holgado,
    K. Bachari, A. Caballero, O. Cherifi

Journal of CO2 Utilization, 14 (2016) 98-105.

Keywords: hydrotalcite, dry reforming of methane, hydrogasification, catalyst regeneration


 

PREDICTION OF EQUILIBRIUM SWELLING RATIO ON SYNTHESIZED
POLYACRYLAMIDE HYDROGEL USING CENTRAL COMPOSITE DESIGN
MODELING

  1. Hamri, D. Lerari, M. Sehailia, B. Dali‑Youcef, T. Bouchaour, K. Bachari

International Journal of Plastics Technology, (2018) 1-15.

Keywords Central composite design (CCD) · Swelling ratio · temperature · crosslinking · Eosin Y · Polyacrylamide


 

SPECTROSCOPIC AND MOLECULAR MODELLING INVESTIGATIONS OF SUPRAMOLECULAR COMPLEX OF B-CYCLODEXTRIN WITH N-[(4-SULFONAMIDOPHENYL) ETHYL]-5-(1,2-DITHIOLAN-3-YL)PENTANAMIDE

  1. Bouzit, M. Stiti, M. Abdaoui

J Incl Phenom Macrocycl Chem, 86 (2016) 121–134.

Keywords: N-(4-sulfonamidophenyl)ethyl]-5-(1,2- dithiolan-3-yl)pentanamide Lipoic acid hCA IX inhibitors b-Cyclodextrin Inclusion complex Molecular modeling

 

 

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