Publications by authors named "Salah Akkal"

23 Publications

  • Page 1 of 1

LC-ESI/MS-phytochemical profiling with antioxidant and antiacetylcholinesterase activities of Algerian L.f. extracts.

Nat Prod Res 2021 Jul 5:1-7. Epub 2021 Jul 5.

Valorization of Natural Resources, Bioactive Molecules and Biological Analysis Unit, Department of Chemistry, University of Mentouri Constantine1, Constantine, Algeria.

L.f. is a flowering plant from the Asteraceae family that is native to South Africa and which was observed recently in the north and the east of Algeria. This study was aimed for the first time, to evaluate concomitantly phytochemical profiles, using LC-ESI/MS analysis, following by testing and assessing antioxidant and antiacetylcholinesterase activities of these specific species. The results indicated that the hydromethanolic and the acetate extracts have shown remarkable potent inhibitory effects on AChE with IC of (6.04 ± 0.05; 6.72 ± 0.10 µg/mL) respectively along with antioxidant potential of acetate for FRAP and phenanthroline methods with A of (11.15 ± 0.72; 5.72 ± 0.13 µg/mL) successively. Moreover, a high amount of cynarin and -ferulic acid was found in this extract whilst butanolic extract has recorded the highest amount of chlorogenic acid. Indeed phenolic compounds usually have a hydroxyl in their structure which may contribute significantly to the antioxidant activity.
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http://dx.doi.org/10.1080/14786419.2021.1947274DOI Listing
July 2021

The cosmetic potential of the medicinal halophyte Tamarix gallica L. (Tamaricaceae) growing in the eastern of Algeria: photoprotective and antioxidant activities.

Comb Chem High Throughput Screen 2020 Dec 4. Epub 2020 Dec 4.

Valorization of Natural Resources, Bioactive Molecules and Biological Analysis Unit, Department of Chemistry, University of Mentouri Constantine1, Constantine. Algeria.

Aim And Objective: Currently, the use of ingredients from natural sources has gained great attention in cosmetic field especially for the development of new photoprotective formulations. Therefore, the present study aimed to evaluate the cosmetic potential of the methanolic crude extract and the ethyl acetate fraction of the medicinal halophyte Tamarix gallica (Tg) growing in the area of Tebessa in eastern of Algeria, by assessing their phenolic and flavonoid contents, photoprotective and antioxidant activities.

Methods: The research approach consisted of determination phenolic and flavonoid contents of aerial parts via FolinCiocalteu and aluminum chloride methods respectively. The antioxidant activity was measured through two in vitro methods DPPH radical scavenging activity and total antioxidant capacity test (TAC). The in vitro photoprotective effect was performed according to the parameter SPF (Sun Protection Factor) by using UV spectroscopic method in UV-B region (290-320 nm).

Results: The methanolic extract (Tg-MeOH) and ethyl acetate (Tg-EtOAc) fraction showed good antioxidant activity with IC50's 14,05±0,66, 27,58±1,98 µg/mL respectively in DPPH test. Furthermore, both extracts displayed strong total antioxidant capacity (287.01±7.85, 246.7±1.12 mg AAE/g, respectively) in TAC test. Both extracts exhibited high photoprotective activity, with sun protection factor (SPF) values 37.03±0.22 and 36.08±0.03. The antioxidant and photoprotective activities of these extracts is probably related to polyphenols content (190.27±0.74 mg AGE /g and 121.77±1.29 mg AGE /g, respectively) , and flavonoids (78.75±0.06 mg QE /g and 58.67±1.19mg/g).

Conclusion: Our finding show that extracts of Tamarix gallica L could be a promising source to be mixed as natural sunscreens and antioxidants agent into photoprotective cosmetic formulations.
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http://dx.doi.org/10.2174/1386207323666201204141541DOI Listing
December 2020

Comparison between Phenolic Content, Antioxidant and Antibacterial activity of Algerian and Turkish Propolis

Comb Chem High Throughput Screen 2020 11 11. Epub 2020 Nov 11.

Department of Chemistry, Faculty of Science, , University Mentouri-Constantine 1, Constantine,. Algeria.

Background: Propolis is a natural resinous material produced by honeybees. Propolis biological activity and its phenolic profile were largely studied all over the world. However, only few investigations have been carried out on Algerian and Turkish propolis. The aim of the present study is to compare the phenolic content, antioxidant and antibacterial activity of propolis samples collected from different localities of Algeria and Turkey.

Methods: Propolis extracts were performed using maceration in ethanol 80%. Total phenolic and flavonoid contents were determined. Antioxidant and antibacterial activities were evaluated using FRAP assay and the determination of MIC against four bacterial strains (S. aureus ATCC 25923, E. coli ATCC 25922, P. aeruginosa ATCC 27853 and K. pneumonia).

Results: TP varied from 19.51 ± 0.86 to 219.66 ± 1.23 mg GAE/g. Whereas, TF varied from 5.27± 0.07 to 74.57 ± 1.03 QE/g. All samples showed good ferric reducing antioxidant power ranging from 267.30 ± 4.77 to 2387.30 ± 44.15 μmol Trolox eq./g. All Algerian propolis samples displayed a more pronounced activity against S. aureus ATCC 25923 with MIC values ranging from 0,04 ± 0.00 mg/mL to 0.30±0.06 mg/mL with an activity 30 times more powerful than Anatolian propo-lis. While, Anatolian propolis samples were most active against P. aeruginosa ATCC 27853 with MIC values ranging from 0.20±0.00 mg/mL to 0.60±0.00 mg/mL with an activity 5 to 10 times more powerful than Algerian propolis.

Conclusion: Algerian and Anatolian propolis possessed considerable phenolic and flavonoids contents. In addition, they ex-hibited an interesting antioxidant and antibacterial activities. Our finding suggest that both propolis could be useful in food and pharmaceutical industries.
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http://dx.doi.org/10.2174/1386207323999201111193040DOI Listing
November 2020

Chemical Composition, Antioxidant, Genotoxique and Antigenotoxic Potentials of De Noé Aerial Parts.

Iran J Pharm Res 2020 ;19(1):282-291

Département de Chimie, Laboratoire de Recherche en Phytochimie et Analyse Physicochimique, Université Mentouri, Constantine, Algeria.

In the present work, chemical investigation of the aerial parts of de Noé an endemic species from Algeria, led to the isolation and identification of seven known compounds including five flavones glycosides: Chrysoeriol 7--(3''-( et )--coumaroyl)-β-glucoside , terniflorin (apigenin-7--(6''--coumaroyl)glucoside) , apigenin-7--(6''-(5'''-methoxy-coumaryl) glucoside , apigenin 7--(3″--coumaryl) , hispidulin-7--glucuronide and two cinnamic acid derivatives: -coumaric acid methyl ester ( et ) , chlorogenic acid . Compound is described for the first time in the species de Noé, the genus and the family. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. Some pure compounds and extracts have been evaluated for their antioxidant activities through different methods: DPPH and ABTS assays as well as CUPRAC assay. Genotoxic and antigenotoxic activities of pure compounds were also evaluated on PQ37 cells by the SOS Chromotest.
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http://dx.doi.org/10.22037/ijpr.2019.15197.12938DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7462515PMC
January 2020

Phenolic Compounds from An Algerian Endemic Species of var. and Investigation of Antioxidant Activities.

Plants (Basel) 2020 Apr 16;9(4). Epub 2020 Apr 16.

Laboratory of Valorization of Natural Resources, Bioactive Molecules and Physicochemical and Biological Analyzes Department of Chemistry, Faculty of Exact Sciences, University of Constantine 1, Constantine, Algeria.

var. (Asteraceae) is an endemic plant from Algeria. In the current study, we analyzed for the first time its chemical composition, especially phenolic constituents of dichloromethane (DCM), ethyl acetate (EA), and n-butanol (BuOH) fractionsof the aerial parts of var. by liquid chromatography-mass spectrometry (LC-MS/MS). The number of phenolic compounds detected in DCM, EA, and BuOH fractions were found to be 9, 20, and 15, respectively. More specifically, 12 phenolic acids were detected. Among them, quinic acid, chlorogenic acid, and caffeic acid were the most abundant ones. Meanwhile, only seven flavonoids were detected. Among them, rutin, apigetrin, and isoquercitrin were the major ones. We also determined the total phenolic and flavonoid contents, and fraction EA showed the highest values, followed by BuOH, and DCM fractions. Furthermore, the antioxidant action was dictated by five methods and the tested plant fractions demonstrated a noteworthy antioxidant action.
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http://dx.doi.org/10.3390/plants9040514DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7238426PMC
April 2020

Coss and Durieu: Phytochemical Composition and Biological Activities.

Molecules 2020 Apr 3;25(7). Epub 2020 Apr 3.

LAQV-REQUIMTE Department of Chemistry & Organic Chemistry, Natural Products and Food Stuffs Research Unit, University of Aveiro, 3810-193 Aveiro, Portugal.

is an Algerian-Tunisian endemic species, which has not been studied yet. Ethyl acetate (EA) and -butanol (Bu) fractions obtained from were investigated for their health benefit properties, in particular with respect to in vivo/in vitro anti-inflammatory and antioxidant activities, as well as their potential to inhibit key enzymes with impact in diabetes (α-glucosidase and α-amylase). The fractions had a distinct phytochemical composition, of which EA was richer in total phenolic compounds (225 mg GAE/g) and mostly composed of the phenylethanoid acetyl martynoside. Compared to EA, Bu had higher amounts of total flavonoids, and according to the result obtained from UHPLC-DAD-ESI-MS analysis, harpagoside (iridoid) was its major phytochemical. EA fraction was quite promising with regard to the in vivo (at 200 mg/kg, po) anti-inflammatory effect (62% and 52% for carrageenan-induced rat paw edema and xylene-induced ear edema tests, respectively), while Bu fraction exhibited a stronger antioxidant capacity in all tests (IC = 68 µg/mL, IC = 18 µg/mL, IC = 18 µg/mL and A = 43 µg/mL for DPPH, ABTS, O scavenging assays and cupric-reducing antioxidant capacity method, respectively). Both fractions also showed a strong effect against α-amylase enzyme (IC = 8 µg/mL and 10 µg/mL for EA and Bu fraction, respectively).
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http://dx.doi.org/10.3390/molecules25071647DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7181002PMC
April 2020

New approach in the characterization of bioactive compounds isolated from Calycotome spinosa (L.) Link leaves by the use of negative electrospray ionization LITMS, LC-ESI-MS/MS, as well as NMR analysis.

Bioorg Chem 2020 03 23;96:103535. Epub 2019 Dec 23.

Laboratoire de Mycologie, de Biotechnologie et de l'Activité Microbienne (LaMyBAM), Département de Biologie Appliquée, Université des Frères Mentouri, Constantine1, BP, 325 Route de Aïn El Bey, Constantine 25017, Algeria.

Two novel compounds were isolated for the first time from Calycotome spinosa (L.) Link, an alkaloid 5-Hydroxy-1H-indole (4) and a cyclitol D-pinitol (5), together with the three well-known flavonoids; Chrysin-7-O-(β-D-glucopyranoside) (1), Chrysin-7-O-β-D-(6″-acetyl)glycopyranoside (2) and Apigenin-7-O-β-D-glycopyranoside (3). The chemical structures of the isolated compounds were elucidated by spectroscopic data and mass spectrometric analyses; including a fresh approach 1D-NMR, 2D-NMR with LC-ESI-MS/MS. In this study, the new compound (4) that has been obtained from the leaves MeOH extract presented the best radical scavenging activity (DPPH) (IC < 10 µg/mL) compared to the standard butylated hydroxytoluene (BHT, IC = 34.73 ± 0.23 μg/mL) and showed the highest total antioxidant capacity (TAC = 985.54 ± 0.13 mg AAE/g extract) in contrast to ascorbic acid (TAC = 905.95 ± 0.07 mg AAE/g extract). Furthermore, the strongest reducing power (EC = 344.82 ± 0.02 µg/mL), as well as the remarkable scavenging potential by ABTS assay (IC = 7.8 ± 0.43 µg/mL), were exhibited by the same composite (4). Followed by the methanol crude extract and the compound (3) that also showed a potent antioxidant (DPPH; IC = 41.04 ± 0.15 and 47.36 ± 0.21 µg/mL, TAC; 671.02 ± 0.21 and 608.67 ± 0.34 mg AAE/g extract, FRAP; EC = 763.73 ± 0.32 and 814.61 ± 0.31 µg/mL, ABTS; IC = 19.18 ± 0.06 and 63.72 ± 0.64 µg/mL, respectively), but less than the previous samples. On the opposite side, compound (5) had the lowest activity, in which its values were less interesting to determine. Moreover, compound (4) has equally exerted an attractive antibacterial activity against Staphylococcus aureus (ATTC-25923), Pseudomonas aeruginosa (ATTC- 27853) and Salmonella abony (NCTC 6017), as measured by the disc diffusion assay, with inhibition zones of 16 ± 0.5, 9.83 ± 0.29 and 8 ± 0.28 mm, in that order. To the best of our knowledge, 5-Hydroxy-1H-indole was isolated from plants for the second time in our current work. Thus, the obtained results from this investigation propose that the leaves of C. spinosa are a rich natural source for value molecules as potential antioxidants and antimicrobial agents for best human health.
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http://dx.doi.org/10.1016/j.bioorg.2019.103535DOI Listing
March 2020

A nutraceutical extract from Inula viscosa leaves: UHPLC-HR-MS/MS based polyphenol profile, and antioxidant and cytotoxic activities.

J Food Drug Anal 2019 07 14;27(3):692-702. Epub 2019 Jan 14.

Department of Environmental, Biological and Pharmaceutical Sciences and Technologies, University of Campania "Luigi Vanvitelli", Via Vivaldi 43, I-81100, Caserta, Italy. Electronic address:

Nowadays, advanced extraction techniques and highly sensitive metabolic profiling methods are effectively employed to get new information on plant chemical constituents. Among them wild medicinal plants or their parts, with large and ancient use in folk medicine, are investigated for their potential functional use and cultivation. In this context, Inula viscosa leaves engaged our attention. A simple experimental design, based on Soxhlet extraction and chromatographic fractionation, allowed us to obtain the investigated polyphenol fraction (IvE). UHPLC-HRMS analyses revealed shikimoyl depsides of caffeic acid and unusual dihydrobenzofuran lignans as main secondary metabolites. These compounds, together with cinchonain-type phenols, and hydroxycinnamoyl flavonol glycosides, are reported for the first time in inula. Overall, forty-three secondary metabolites were identified. The extract exerted a remarkable antiradical activity towards DPPH and ABTS. Furthermore, it was able to inhibit cell viability and mitochondrial redox activity of neuroblastoma, hepatoblastoma and colon carcinoma cells, whereas it did not affect cell density of HaCaT cells immortalized human keratinocytes. As detected by the oxidant-sensing probe 2',7'-dichlorodihydrofluorescein diacetate, the inhibitory responses seemed to be related to IvE-induced increase of intracellular reactive oxygen species (ROS). The obtained results highlighted that inula leaves, nowadays even undervalued and unexplored, could be considered a renewable source of nutraceutical compounds.
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http://dx.doi.org/10.1016/j.jfda.2018.11.006DOI Listing
July 2019

Preliminary analysis of the chemical composition, antioxidant and anticholinesterase activities of Algerian propolis.

Nat Prod Res 2020 Nov 13;34(22):3257-3261. Epub 2019 Feb 13.

Laboratory of Natural Product and Organic Synthesis, Department of Chemistry, Univesity Constantine 1, Constantine, Algeria.

Many studies demonstrated that Algerian propolis possess a large spectrum of biological activity. However, few studies regarding its chemical composition are available on literature. We aimed in the present study to investigate the chemical composition of Algerian propolis. In addition, the antioxidants and anticholinesterase activities of propolis extracts are also reported. Chemical investigation of Algerian propolis allowed the isolation of 8 compounds. Their structures were identified on the basis of spectral data and comparison with literature. The isolated compounds are considered as markers of poplar and suggesting the use of both species as plant source of the tested propolis. The ethyl acetate extract of the tested propolis demonstrated the highest antioxidant activity. Among the tested extracts, only the petroleum ether and chloroform extracts exhibited an AChE inhibitory activity.
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http://dx.doi.org/10.1080/14786419.2018.1556658DOI Listing
November 2020

Senecipyrrolidine, an unusual pyrrolidine alkaloid isolated from (Desf.) Pelser (Asteraceae).

Nat Prod Res 2019 Aug 30;33(15):2182-2191. Epub 2018 Oct 30.

d Département de Chimie, VARENBIOMOL, Faculté des Sciences Exactes , Université de Constantine 1 , Constantine , Algérie.

Alkaloids and phenolic compounds are among the most biologically active natural products from the / genera (Asteraceae). To isolate original natural products directly from crude polar extracts, centrifugal partition chromatography (CPC) was used. Previously, we reported the phytochemical study of (syn. ) -butanol extract using various classical chromatographical techniques combined with CPC. Herein major constituents from the crude ethyl acetate extract and further compounds from the -butanol extract were purified in only one step using this technique. A new pyrrolidine alkaloid, named senecipyrrolidine was isolated along with thirteen known compounds - -inositol, three phenolic acids, six flavonoids, two quinones and emiline, another pyrrolidine alkaloid - from crude -butanol or ethyl acetate extracts. Pyrrolidine alkaloids were isolated for the first time in the genera and were probably biogenetically related to the two isolated quinones derivatives jacaranone and 3a-hydroxy-3,3a,7,7a-tetrahydrobenzofuran-2,6-dione, isolated in this species.
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http://dx.doi.org/10.1080/14786419.2018.1493584DOI Listing
August 2019

Antiproliferative and Antioxidant Activities of Two Extracts of the Plant Species L.

Medicines (Basel) 2018 Apr 20;5(2). Epub 2018 Apr 20.

Laboratoire de Phytochimie et Analyses Physico-Chimiques et Biologiques, Université Mentouri de Constantine, Route de Aïn El Bey, Constantine 25000, Algeria.

These days, the desire for naturally occurring antioxidants has significantly increased, especially for use in foodstuffs, cosmetics, and pharmaceutical products, to replace synthetic antioxidants that are regularly constrained due to their carcinogenicity. : The study in hand aimed to appraise the antioxidant effect of two extracts using reducing power, anti-peroxidation, and DPPH (1,1 Diphenyl 2 Pycril Hydrazil) scavenging essays, in addition to the anticancer activity against two tumor cell lines, namely C6 (rat brain tumor)cells, and Hela (human uterus carcinoma)cell lines. : The results indicated that the ethyl acetate extract exhibited antiradical activity of 29.49%, higher than that of -butanol extract (18.06%) at 100 µg/mL but much lower than that of gallic acid (78.21%).The ethyl acetate extract exhibits better reducing capacity and lipid peroxidation inhibitory activity compared to -butanol extract but less than all tested standards. Moreover, the ethyl acetate extract was found to have an antiproliferative activity of more than 5-FU (5-fluoro-Uracil) against C6 cells at 250 µg/mL with and of 113.97, 119.49 µg/mL, respectively, and good cytotoxic activity against the Hela cell lines at the same concentration. The HPLC-TOF-MS (high performance liquid chromatography-Time-of-flight-Mass Spectrometry) analyses exposed the presence of various compounds, among which Gallic and Chlorogenic acids functioned as major compounds. : The two extracts exhibited moderate anticancer abilities and behaved somewhat as average antioxidant agents. Based on the total phenolics and flavonoids contents, as well as HPLC results, it could be concluded that antiproliferative and antioxidant activities depend upon the content of different phenolics and flavonoids.
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http://dx.doi.org/10.3390/medicines5020036DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6023373PMC
April 2018

In Vitro Assessment of Total Phenolic and Flavonoid Contents, Antioxidant and Photoprotective Activities of Crude Methanolic Extract of Aerial Parts of Capnophyllum peregrinum (L.) Lange (Apiaceae) Growing in Algeria.

Medicines (Basel) 2018 Mar 22;5(2). Epub 2018 Mar 22.

Valorization of Natural Resources, Bioactive Molecules and Biological Analysis Unit, Department of Chemistry, University of Mentouri Constantine, Constantine 25000, Algeria.

(L.) Lange (Apiaceae) is the unique taxon of genus in Algerian flora. It has never been investigated in regards to its total phenolic and flavonoid contents and antioxidant and photoprotective activities. aerial parts extracted with absolute methanol. The total flavonoid and phenolic contents of the extract were evaluated to determine their correlation with the antioxidant and photoprotective activities of the extract. The methanolic extract demonstrated a significant amount of phenolics and flavonoids (74.06 ± 1.23 mg GAE/g, 44.09 ± 2.13 mg QE/g, respectively) and exhibited good antioxidant activity in different systems, especially in 1,1-Diphenyl-2-picrylhydrazyl (DPPH), reducing power and total antioxidant capacity assays. Furthermore the extract showed high photoprotective activity with the sun protection factor (SPF) value = 35.21 ± 0.18. The results of the present study show, that the methanolic extract could be used as a natural sunscreen in pharmaceutics or cosmetic formulations and as a valuable source of natural antioxidants.
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http://dx.doi.org/10.3390/medicines5020026DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6023362PMC
March 2018

GREEN TEA BEVERAGE AND EPIGALLOCATECIHIN GALLATE ATTENUATE NICOTINE CARDIOCYTOTOXICITY IN RAT.

Acta Pol Pharm 2017 Jan;74(1):277-287

Nicotine, the principal alkaloid in tobacco, induces a cellular damage on heart and cardiomyocyte culture. We investigate the protective role of green tea extract (GTE) against nicotine. Male albino rats were treated by injecting nicotine (1 mg/kg b.w. for 2 months) subcutaneously and thereby supplementing GTE 2% orally to them. The levels of plasma lipids, cardiac MDA (malondialdehyde) and catalase activity Mitogen-activated proteins kinases MAPKs were measured. The expression levels of (ERK 1/2, extracellular signal - regulated kinase 1/2 and P38 MAP kinase), endoplasmic reticulum stress (ERS)-related protein (GRP78 glucose regulated protein-78, HSP70 heat shock protein-70, CHOP C/EBP homologous protein), AIF (apoptosis-inducing factor) and VDAC (voltage-dependant anion channel) were evaluated by Western blot. In the in vitro study, the cardiomyocytes were exposed to nicotine (10 μM) and major GTE polyphenol epigallocatechin gallate EGCG (50 μM). Data showed that nicotine induced a significant increase on MDA levels, LDH (lactate dehy- drogenase) and aminotransferase activity compared with control. The heart sections of nicotine exposed-rats showed severe degenerative changes. Nicotine increased the expression of P38, but not ERK 1/2, ER stress-related proteins and AIF with no changes of VDAC. Concomitant GTE treatment significantly normalized and/or improved,the levels of MDA, enzymatic activity and histological injuries. The proteins expression was attenuated by GTE co-administration without any changes for VDAC. ERK 1/2 expression enhanced in GTE- treated groups. Exposure of cardiac cells to nicotine induced the expression of ERS markers and p38; the ERK 1/2 was highly expressed only in the presence of EGCG. It was suggested that green tea beverage can protect against nicotine toxicity by attenuating oxidative stress, endoplasmic reticulum stress and apoptosis. Otherwise, our results have showed that ERK1/2 and p38 are survival signaling pathways activated by GTE and EGCG.
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January 2017

Correlation between antioxidant activity and phenolic acids profile and content of Algerian propolis: Influence of solvent.

Pak J Pharm Sci 2017 Jul;30(4(Suppl.)):1417-1423

Laboratory of natural product and organic synthesis. Department of Chemistry. University Constantine 1. Algeria.

We aimed in the reported study to investigate the impact of using various solvents in the extraction of potentially active compounds from Algerian propolis. Phenolic and flavonoids contents in association with antioxidant activity of the tested extracts were evaluated. Moreover phenolic composition was determined using UFLC-MS/MS. The tested parameters varied according to the used solvent. Total phenolic and flavononid contents ranged from 0.81±0.16 to 8.97±0.25 EGA mg/g and from 0.57±0.01 to 3.53±0.84 EQ mg/g respectively. All the investigated extracts demonstrated notable antiradical and reducing activities. Ethyl acetate and n-butanol were found to contain the highest amounts of phenolic and flavonoid compounds and the strongest antioxidant properties. The antioxidant activity of propolis extracts appears to be largely influenced by total phenolic and flavonoid contents. Rutin, chlorogenic, ferulic, caffeic and gallic acids were found to be the main phenolic compounds in Algerian propolis. Our results suggest that Algerian propolis may be a poplar-type propolis.
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July 2017

Chemical characterization of polyphenols from Daucus muricatus growing in Algeria by RP-UHPLC-ESI-QTOF-MS/MS.

Nat Prod Res 2018 Apr 6;32(8):982-986. Epub 2017 Sep 6.

b Department of Chemistry, Bioactive Molecules and Biological Analysis Unit, Valorization of Natural Resources , University of Mentouri Constantine1 , Constantine , Algeria.

In the present work, reversed phase (RP) ultra-high-performance liquid chromatography (UHPLC) coupled to quadrupole-time-of-flight (QTOF) mass spectrometry in tandem has been used for the identification of the main phenolic compounds in the aerial parts of Daucus muricatus. The characterisation of the compounds was carried out taking into account retention time, mass accurate measurements, the generated molecular formulae and fragmentation pattern. These data were contrasted with literature and databases, as well as with those of authentic standards when possible. The proposed method provided tentative identification of 30 phenolic and other polar compounds, including hydroxycinnamic acid derivatives, flavonoids and hydroxybenzoic acid derivatives. As a note, hydroxycinnamic acid derivatives were found to be the most diverse phenolic class of Daucus muricatus.
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http://dx.doi.org/10.1080/14786419.2017.1371162DOI Listing
April 2018

Two new triterpenoid saponins from the leaves of Bupleurum lancifolium (Apiaceae).

Nat Prod Res 2017 Oct 5;31(19):2286-2293. Epub 2017 May 5.

a Faculté des Sciences exactes, Département de Chimie, Unité de Valorisation des ressources naturelles, Molécules Bioactives et Analyses Physiquo-Chimiques et biologiques , Université des frères Mentouri Constantine1 , Constantine , Algérie.

Chemical investigation of the leaves of Bupleurum lancifolium led to the isolation and identification of two triterpenoid saponins previously undescribed named 3-O-[α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl] echinocystic acid 28-O-β-D-glucopyranosyl ester (1) and 3-O-[α-L-rhamnopyranosyl (1 → 4)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (2) along with the two known compounds isorhamnetin 3-rutinoside (3) and rutin (4). Their structures were elucidated by different spectroscopic methods, including HRESIMS analysis as well as 1D and 2D NMR experiments.
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http://dx.doi.org/10.1080/14786419.2017.1324960DOI Listing
October 2017

A novel benzimidazole and other constituents with antiproliferative and antioxidant properties from Thymelaea microphylla Coss. et Dur.

Nat Prod Res 2017 Sep 20;31(17):2032-2041. Epub 2017 Jan 20.

a Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Faculty of Science , University of Mentouri-Constantine , Constantine , Algeria.

A new compound (microphybenzimidazole, 7) along with the six known compounds matairesinol (1), prestegane B (2), umbelliferone (3), daphnoretin (4), microphynolide A (5) and microphynolide B (6) were isolated from Thymelaea microphylla. The structures of the pure compounds were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR, and HPLC-TOF/MS. Compounds 2 and 4, as well as three fractions (F6, F6-C5, and F6-W42) obtained from a 50% (v:v) CHCl:MeOH extract exhibited a selective activity against rat brain glioma cells (C6). Moreover, compound 1 and other fractions obtained from 50% (v:v) CHCl:MeOH and 70% (v:v) MeOH:HO extracts exhibited dose- and time-dependent effects on human cervical cancer cell (HeLa), as measured by xCELLigence assay. Compound 2 (IC = 14.0 ± 0.2 μg/mL) and fraction F5 (IC = 12.4 ± 0.1 μg/mL) showed higher radical scavenging ability than the synthetic agent butylated hydroxytoluene (BHT, IC = 22.7 ± 0.6 μg/mL).
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http://dx.doi.org/10.1080/14786419.2016.1274888DOI Listing
September 2017

Phytochemical and biological activities of Bituminaria bituminosa L. (Fabaceae).

Asian Pac J Trop Med 2014 Sep;7S1:S481-4

UMR 5557, Ecologie Microbienne, ISPB, 69373 Lyon, France.

Objective: To investigate the phytochemical composition, the antioxidant and antibacterial activities of Bituminaria bituminosa L. (Fabaceae) (B. bituminosa).

Methods: The aerial parts of B. bituminosa yielded two compounds. The structures of these compounds were determinated using UV, (1)H-NMR and (13)C-NMR experiments and comparison of their spectroscopic properties with literature data. The antibacterial activity of the extracts (CH2Cl2, ethyl acetate and n-BuOH) was determinated using disk diffusion method against standard and clinical strains. Antioxidant potential of n-BuOH extract was evaluated through two methods: DPPH and cupric ion reducing antioxidant capacity assay.

Results: The n-BuOH extract from B. bituminosa yielded the isolation of isoflavone and flavone. The extracts CH2Cl2, ethyl acetate and n-BuOH demonstrated significant antibacterial activities. CH2Cl2 extract showed the maximum antibacterial activity with high concentration of 2 mg/mL against Staphylococcus aureus ATCC 29213, Klebsiella pneumonia and Escherichia coli ATCC 25922 (20.45 mm, 16.41 mm and 15.74 mm inhibition zone, respectively). The value IC50 was 0.26 μg/mL for n-BuOH extract using DPPH method. Whereas the E% value was 0.10 L/mg every centimeter for cupric ion reducing antioxidant capacity assay.

Conclusions: The phytochemical study of B. bituminosa revealed the presence of isoflavone (daidzin) and flavone (isoorientin) and identified for the first time in this specie. The antibacterial activity of the plant B. bituminosa is certainly related to its chemical content. The n-BuOH extract showed a significant antioxidant activity.
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http://dx.doi.org/10.1016/S1995-7645(14)60278-9DOI Listing
September 2014

Flavonoids from Algerian endemic Centaurea microcarpa and their chemotaxonomical significance.

Nat Prod Commun 2011 Nov;6(11):1603-4

Université Mentouri, Constantine, Laboratoire de Phytochimie et d'Analyses Physico-chimiques et Biologiques, Département de Chimie, Faculté des Sciences exactes, Algeria.

Six flavonoids, namely 6-methoxykaempferol (1), 6-methoxykaempferol 7-O-glucoside (2), kaempferol 7-O-glucoside (3), 6-methoxyluteolin (4), patuletin 7-O-glucoside (5), and hispidulin 7-O-glucoside (6), were isolated from a n-butanolic fraction of Centaurea microcarpa Coss et Dur. flowers. This work describes for the first time the phytochemical composition of this endemic Algerian plant.
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November 2011

Antioxidant and antigenotoxic properties of compounds isolated from Marrubium deserti de Noé.

Food Chem Toxicol 2011 Dec 6;49(12):3328-35. Epub 2011 Sep 6.

UMR 5557 CNRS-UCBL - Ecologie Microbienne, Equipes 6/1/5, CESN, ISPB, 8 Avenue Rockefeller, F69373 Lyon cedex, France.

In our continual course toward the valorization of traditionally used endemic flora through the analysis of its chemobiodiversity, the phytochemical analysis of aerial parts of Marrubium deserti de Noé was undertaken. Dichloromethane and methanol extracts led to the isolation of terpenoid derivatives among which two were new labdane diterpenes named marrulibacetal A and desertine, respectively. Six of them were known compounds (a mixture of the isomers cyllenin A and 15-epi-cyllenin A, marrubiin, marrulactone, marrulibacetal and β-stigmasterol) and seven known phenolic compounds were also isolated: apigenin and several 7-O-substituted derivatives (apigenin-7-O-β-neohesperidoside, apigenin-7-O-glucoside, terniflorin and apigenin-7-O-glucuronide) together with two phenylethanoid glucosides (acteoside and forsythoside B). The structures and relative configurations of the new compounds were elucidated by MS and a series of 1D and 2D NMR analyses. Some pure compounds have been evaluated for their antioxidant activities through different methods: DPPH and ABTS assays as well as CUPRAC assay. Genotoxic and antigenotoxic activities of extracts and pure compounds were also evaluated in vitro on Escherichia coli PQ37 cells by the SOS Chromotest. Some of the isolated compounds like phenylethanoid derivatives showed stronger antioxidant capacity than trolox and were also able to significantly inhibit β-galactosidase induction caused by the mutagen agent nitrofurantoin.
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http://dx.doi.org/10.1016/j.fct.2011.08.026DOI Listing
December 2011

Chemical composition and antimicrobial activity of essential oil of Bupleurum montanum and B. plantagineum.

Nat Prod Commun 2009 Nov;4(11):1605-10

Laboratory of Natural Resources Valorization, Department of Biology, Ferhat Abbas University, Setif, Algeria.

The hydrodistilled oils from the aerial parts of Bupleurum montanum and B. plantagineum, which are endemic to North Africa, including Algeria, were analyzed by gas chromatography-mass spectrometry (GC-MS). Ninety-eight compounds were detected in the oil of B. montanum, representing 98.6% of the total oil, and 68 in the oil of B. plantagineum, representing 99.8% of the total. Megastigma-4,6-(E),8(2)-triene was the major constituent of B. montana oil (25.3%). Other important compounds were myrcene, alpha-pinene and benzyl tiglate. Conversely, the major constituents of the oil of B. plantagineum were alpha-pinene (31.9%), cis-chrysanthenyl acetate (28.2%), and myrcene (24.8%), followed by the monoterpene hydrocarbon limonene (5.1%). The mutagenic, antiplasmodial and antimicrobial activities of the essential oils were individually evaluated against eleven microorganisms, using the agar diffusion method, by determination of MIC values. The investigated oils exhibited moderate antimicrobial activity. Maximum activity of the oils was observed against Nocardia asteroides, Staphylococcus aureus and Enterococcus faecalis. Fungicidal activity against Candida albicans was also found for both oils.
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November 2009

Fast counter current chromatography of n-butanolic fraction from Senecio giganteus (Asteraceae).

Nat Prod Commun 2009 Oct;4(10):1357-62

Université Mentouri, Constantine, laboratoire de Phytochimie et d'Analyses Physico-chimiques et Biologiques, département de Chimie, Faculté des Sciences exactes, Algérie.

Phenolic derivatives such as quinones, acid-phenols and flavonoids were successfully isolated from a n-butanolic fraction of Senecio giganteus Desf. (Asteraceae) flowers, namely jacaranone (1), 3a-hydroxy-3,3a,7,7a-tetrahydrobenzofuran-2,6-dione (2), chlorogenic acid (3), hyperoside (4), quercetin 3-O-beta-D-robinobioside (5), isorhamnetin-3-O-beta-D-glucuronide (6), quercetin-3-O-beta-D-glucuronide (7), and isorhamnetin-3-O-beta-D-glucuronide-6"-methyl ester (8). These compounds were purified through either classical polyamide filtration followed by fractionation on Si gel, or through fast centrifugal partition chromatography (FCPC). Using FCPC, the major compounds could be readily isolated from the crude n-butanolic fraction. Compounds 1-8 were identified by means of spectroscopic and spectrometric analysis (UV, 1H, 13C and 2D NMR, and MS). This work described for the first time the phytochemical composition of this endemic Algerian plant.
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October 2009

Variability of two essential oils of Kundmannia sicula (L.) DC., a traditional Algerian medicinal plant.

Molecules 2008 Apr 8;13(4):812-7. Epub 2008 Apr 8.

Laboratoire Phytochimie et Analyses Physico-chimiques et Biologiques, Université Mentouri Constantine, Route de Aïn El Bey, 25000 Constantine, Algeria.

The essential oils of the aerial parts of Kundmannia sicula (L.) DC collected from two Algerian localities, El Kala (near the coast) and Béjaia (from a meadow about 10 km from the coast), were analysed by GC and GC-MS. Although both samples showed similar overall chemical compositions, the major components of the Béjaia sample were identified as being spathulenol (14.8%), caryophyllene oxide (12.2%), salvial-4(14)en-1-one (10.1%), 1,5-epoxysalvial-4(14)ene (5.2%) and germacrene D (3.2%), while in the ElKala sample the main compounds were found to be salvial-4(14)en-1-one (16.4%), 1,5-epoxysalvial-4(14)ene (6.5%), chrysanthenyl acetate (5.2%) and alpha-amorphene (2.9%).
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6245461PMC
http://dx.doi.org/10.3390/molecules13040812DOI Listing
April 2008