Nour Eddine Es-Safi

• Professor
• Mohammed V University in Rabat. Ecole Normale Supérieure

Retama dasycarpa is an endemic shrubby leguminous plant of Morocco used in traditional folk medicine. The plant has never been studied for either its phytochemical or pharmacological properties. This study represents the first investigation of the phytochemical profile as well as the antioxidant, the antibacterial, the analgesic effects and the ora...

Environmentally-friendly extraction methods enables both efficient extraction of phenolic compounds from plant sources and safe use of the extracted substances. These characteristics render them as ideal choices for sustainable extraction processes. This study combines a green and sustainable extraction strategy with an intelligent statistical appr...

Cotula cinerea of the Asteraceae family is a traditional plant which grows in desert area. The plant is endowed with various biological activities due to the presence of several secondary metabolites. Owing to its use in traditional folk medicine and its interesting biological effects, the plant has been subjected to many scientific explorations re...

This study was designed to optimize the ultrasound-assisted extraction of phenolic compounds and the antioxidant activity of Moroccan Retama sphaerocarpa extracts using response surface methodology (RSM). A central composite design has been conducted to investigate the effects of three factors: extraction period (X1), solvent concentration (X2), an...

Broomrape (Orobanche crenata Forsk.) is a serious problem causing important losses to lentil (Lens culinaris Medik.) production and productivity in Mediterranean countries. Despite intensive breeding activities, no resistance sources against O. crenata have been identified so far. In this study, a Global Lentil Diversity Panel (GLDP) of 1315 genoty...

Background Salvia verbenaca of the Lamiaceae family is a Mediterranean plant widely used in the Moroccan traditional folk medicine. The aim of this work was to explore the phytochemical composition of Salvia verbenaca extracts and its antioxidant activity. Methods Separation and identification of the major phytochemicals present in the two hexane...

Introduction: Ethanolic fraction of Moroccan Cannabis sativa threshing residues (EFCS) was evaluated for its vasorelaxant activity. The current work aims to identify the active metabolites in the ethanolic fraction of the EFCS and illustrate their mechanism of action. Methods: Free radical scavenging capacity of EFCS was assessed using DPPH meth...

Parasitic weeds are troublesome plants that are completely dependent on their hosts for their water and nutrients’ requirement. They cause severe damages to many important and strategic staple food crops. The host-parasite interaction starts with early germination of the parasitic seeds in response to host-derived chemical signals, the germination...

This study was designed to predict the optimized solvent mixture for extracting phenolic compounds from Moroccan Retama raetam. A mixture design methodology (MDM) and artificial neural networks (ANNs) were employed in a solvent system containing water, ethanol, and methanol to optimize the three responses: extraction yield, total phenol content (TP...

Background The development of digital technologies and the evolution of open innovation approaches have enabled the creation of diverse virtual organizations and enterprises coordinating their activities primarily online. The open innovation platform titled “International Natural Product Sciences Taskforce” (INPST) was established in 2018, to bring...

Background: The development of digital technologies and the evolution of open innovation approaches have enabled the creation of diverse virtual organizations and enterprises coordinating their activities primarily online. The open innovation platform titled "International Natural Product Sciences Taskforce" (INPST) was established in 2018, to brin...

This study aimed to improve the extractive effect of four solvents and their combinations on phenolic compounds from Moroccan Lavandula stoechas leaves. A simplex-centroid design was used in a solvent system containing ethyl acetate, methanol, ethanol, acetone, and their mixtures to optimize the five responses: extraction yield, total phenol conten...

Molecules Special Issue - Invitation to contribute

The current study was performed in order to evaluate the effect of using argane by-products (oil cake and pulp) as fattening diet of lambs. This was achieved through an experimental lamb fattening investigation using argan by-product as feeding source and the exploration of the fattened lamb performance, carcass characteristics and the chemical fat...

Management of broomrape (Orobanche crenata Fosk.) that causes important damages on lentil production becomes a veritable concern in the Mediterranean region. Eighty lentil accessions were evaluated for resistance to O. crenata under field and controlled conditions. Both genotypes ILL6415 and ILL7723 expressed the highest resistance level under fiel...

Lentil (Lens culinaris Medikus) is one of the most important cool season food legume crops grown in many countries. Seeds are typically rich in protein, fiber, prebiotic carbohydrates and minerals, such as iron and zinc. With changing climate and variability, the lentil crop faces frequent droughts and heat stress of varying intensity in its major...

Rationale: Cotula cinerea of the Asteraceae family is a traditional Moroccan plant, with various biological activities such as analgesic, cytotoxic and antioxidant effects which are often related to the presence of secondary metabolites. The present work aims to screen and identify the main phytochemicals compounds of Cotula cinerea extracts. Met...

The objective of this work was to study the effect of the incorporation of argane by-products (meal and pulp) in ewe’s diet on the production and quality of milk and the performance of lambs in the lactation phase. Twenty ewes were divided into two equal groups. The first one has been fed with argane by-product diet (AD), and the second with a cont...

The acute and subchronic toxicological effects of Salvia verbenaca extracts in hexane, ethyl acetate, n-butanol, were investigated. The extracts were not toxic at 2000 mg Kg⁻¹. A normal body weight evolution was observed during the 14 treatment days where there was no difference between the control and the treated groups. No abnormalities were seen...

The objective of this work was to investigate the cytotoxicological effect of the extracts (hexane, ethyl acetate, and n-butanol) of Cotula cinerea and Salvia verbenaca in addition to the essential oil of Cotula cinerea. These plants are widely used in the Moroccan traditional folk medicine. The cytotoxic effect was explored against two cancer cell...

Background: Salvia verbenaca is a Mediterranean plant currently belonging to the Lamiaceae family. The plant is widely distributed in Morocco and is widely used in Moroccan traditional folk medicine as a cholagogue, antiseptic, diuretic and astringent. The crushed or chopped fresh leaves are also applied in poultices on wounds and emptied abscesses...

Background: Cotula cinerea belongs to the Asteraceae family and grows in desert areas such as Moroccan Sahara. The use of this plant in Moroccan traditional medicine prompted us to investigate its chemical composition, its acute oral toxicity, its analgesic and antioxidative activities. Methods: Extraction was conducted by steam distillation for es...

Two new isomeric oxazolidin-2-one derivatives have been synthesized through reaction of (E)-3-styrylquinoxalin-2-one with bis-dichloroethylamine hydrochloride in presence of potassium carbonate. The structures of the formed products were established by NMR and mass spectroscopy. The fragmentation patterns of the two novel synthesized oxazolidin-2-o...

Two new isomeric heterocyclic systems containing oxazolidin-2-one and quinoxaline moieties have been synthesized through reaction of (E)-3-styrylquinoxalin- 2-one with bis-dichloroethylamine hydrochloride in presence of potassium carbonate. The structures of the formed products were established by NMR and mass spectroscopy. The fragmentation patter...

Punica granatum L. is widely recognized for its potency against a broad spectrum of bacterial pathogens. The purpose of this study was to explore the inhibitory and the bactericidal activities of Punica granatum against Salmonella strains. The effect of extracts obtained from different parts (peels, seeds, juice and flowers) of pomegranate and usin...

Lentil (Lens culinaris subsp. culinaris Medikus) is an important cool-season food legume crop commonly grown under rainfed conditions in South Asia, North America, West Asia and North Africa (WANA). Occurrence of drought and heat stress during the reproductive stage in most of these environments, causing substantial reduction in crop yield. Lentil...

Lentil (Lens culinaris Medikus) is one of the most important cool season food legume crops. It constitutes good source of seed protein, carbohydrates and minerals particularly to the people living in the developing countries. Terminal drought and heat stress are important factors affecting lentil production especially in the dry and semi-arid regio...

The root parasite, broomrape (Orobanche crenata) poses a serious threat to lentil production in Mediterranean and West Asian countries. Identification of resistant sources in the germplasm collections and the development of new tolerant varieties could be helpful to address the issue. However, resistance breeding is hampered by the scarcity of gene...

Fenugreek (Trigonella foenum-graecum) is a medicinal plant which is widely used for its pharmacological properties. In this study the phenolic composition of fenugreek crude seeds originating from Morocco has been investigated. Extraction was performed from defatted seeds by a hydromethanolic solution using an Accelerated Solvent Extractor. HPLC te...

Phenolic compounds have a fundamental importance in the nutritional and sensorial characteristics of olive. In this study phenolic compounds extracted from olive fruit stones of three Moroccan registered cultivars were analyzed. The obtained results showed that the total amount of phenolic compounds varied according to the olive variety. The stones...

The phenolic composition of fenugreek (Trigonella foenum-graecum) germinated seeds originating from Morocco has been investigated. After germination, extraction was performed from defatted germinated seeds by a hydromethanolic solution using an Accelerated Solvent Extractor. HPLC coupled to negative ion electrospray ionisation mass spectrometry and...

Flavonoids are a broad class of polyphenolic secondary metabolites widely dispersed throughout the plant kingdom and found in substantial levels in commonly consumed fruits, vegetables and beverages. These compounds have aroused considerable interest because of their potential beneficial biochemical and antioxidant effects on human health. The stru...

Various new heterocyclic compounds were synthesized starting from 4-phenyl-1,5-benzodiazepin-2-one. Catalytic hydrogenation was first explored leading to the formation of compounds where the diazepinic seven bond ring was or was not opened. Further alkylation reactions of the new formed derivatives were achieved in order to prepare new dipolarophil...

The initiatory heterocyclization yields regioselectively the novel pyrazolo[1,5,4-de]quinoxaline (III) whose bromination followed by nucleophilic substitution gives the new tetracyclic system (VII).

Mass spectrometry is an important tool for the identification and structural elucidation of natural and synthesized compounds. Its high sensitivity and the possibility of coupling liquid chromatography with mass spectrometry detection make it a technique of choice for the investigation of complex mixtures like raw natural extracts. The mass spectro...

New pyrazolo[1.5.4-de]quinoxaline derivatives were prepared by the action of 7-aminoindazole 1 on diethyl and dimethyl acetylene dicarboxylates. The structures of the obtained compounds and the direction of cyclization were investigated through a crystallographic study of compound 2. Further alkylation, hydrogenation, and bromination were also expl...

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New 3-hydroxy-1,5-benzodiazepin-2-ones were synthesized through condensation between o-phenylenediamines with glycidic ester. Alkylation and oxidation of some of the obtained compounds were also explored in different conditions yielding various oxidized and alkylated benzodiazepines. The structural elucidation of the synthesized compounds was achie...

The fragmentation patterns of a series of three novel synthesized 3-hydroxy-4-phenyl-tetrahydro-1,5-benzodiazepin-2-ones (1-3), possessing the same backbone structure, were investigated using electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS) techniques. A simple methodology, based on the use of ESI (positive io...

Two new colorless phenolic compounds were formed from malvidin 3- O-glucoside incubated in an ethanolic solution. Their structures were characterized by means of one- and two-dimensional NMR analysis and through electrospray ionization-mass spectrometry. As compared to the structure of the initial anthocyanin skeleton, the first new compound showed...

NMR and MS techniques were used for the unambiguous structural elucidation of synthesized modified monomeric and dimeric flavan-3-ols presenting different substituents on the A-ring C8 position. The full characterization of the synthesized compounds was achieved by concerted use of NMR and ESI-MS techniques. Assignments of proton and carbon atoms w...

Several flavonols have been transformed upon treatment by Trametes versicolor laccase. Most of the major oxidation products have been isolated by HPLC as pure compounds and their structures have been, when possible, investigated through spectral methods (HPLC–MS and NMR). The results are coherent with the predominance of a dismutation process, lead...

The antioxidant activity of the Globularia alypum phytochemicals were evaluated for their capacity to scavenge the 1,1-diphenyl-2-dipicrylhydrazyl (DPPH°) free radical and some structure–activity relationships were obtained. Assay guided fractionation led to the isolation of syringin, four phenylethanoids, four flavonoids and six iridoids as the ma...

The structure of globularin was studied by a mass spectrometric methodology based on the combined use of positive and negative electrospray ionization, collision‐induced dissociation (CID), and tandem mass spectrometry. The mass spectrometry investigation was achieved through in‐source fragmentation of the deprotonated [M−H], protonated [M+H], lith...

A quinoxaline‐2,3‐dione derivative was synthesized, and its chemical structure was determined through spectral analysis. Alkylation of this compound under phase transfer catalysis (PTC) conditions yielded monoalkylated and diakylated adducts. The monolalkylation process was shown to be regioselective occurring on the quinoxalic nitrogen atom rather...

In a screening program for free radical scavengers, new antioxidant compounds have been obtained by C-8 substitution of various groups on (+)-catechin A ring. Their preparation, purification, identification by MS, 1H and 13C NMR analysis as well as their antiradical/antioxidant properties are reported. In order to explore the substituent effect on...

Several flavonols were chemically transformed upon treatment by Trametes versicolor laccase; the majority of the major oxidation products were isolated (HPLC) as pure compounds and their structures unambiguously established through spectroscopic methods (HPLC-MS), when possible. In some cases, compounds were difficult to obtain either completely pu...

Mass spectrometric methodology based on the combined use of positive and negative electrospray ionization, collision-induced dissociation (CID) and tandem mass spectrometry (MS/MS) has been applied to the mass spectral study of a series of six naturally occurring iridoids through in-source fragmentation of the protonated [M+H]+, deprotonated [M--H]...

Phenolic compounds form one of the main classes of secondary metabolites. They display a large range of structures and they are responsible for the major organoleptic characteristics of plant-derived-foods and beverages, particularly color and taste properties and they also contribute to the nutritional qualities of fruits and vegetables. Phenolic...

Objective: To investigate the in vitro antioxidant activity of the hydromethanolic extract of the aerial parts (leaves and stems) of Salvia verbenaca L. towards fatty acids (linoleic and linolenic acids) and human, low density lipoproteins (LDL) peroxidation. Materials and Methods: Lipid peroxidation was carried out in the presence of the S. verben...

The structure of a polymeric proanthocyanidin fraction isolated from pear juice was characterized by NMR, ESI/MS, and MALDI-TOF/MS analyses, and its antioxidant activity was investigated using the DPPH free radical scavenging method. The results obtained from 13C NMR analysis showed the predominance of signals representative of procyanidins. Typica...

The effect of an electron attracting substituent in the Lewis acid catalyzed oligomerization of flavanols was investigated. The results showed that the presence of a COCF3, at the 8 position of a (+)-catechin unit strongly influenced the attack of the 6 free nucleophile flavanol position by the electrophile generated from a 4-O-alkyloxy protected c...

Benzylic oxidation of catechine has been performed using either DDQ or Ce(IV) trifluoromethanesulfonate as oxidizing agent. These procedures allowed the efficient synthesis of taxifolin 3 in a high overall yield.

From the hydromethanolic extract of the aerial parts of Globularia alypum grown in Morocco, a new chlorinated iridoid glucoside, globularioside has been isolated beside 5 known iridoid glycosides, globularin, globularicisin, globularidin, globularinin and globularimin. This is the first report of a chlorinated iridoid in G. alypum and in the Globul...

A mass spectrometric method based on the combined use of positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry has been applied to the structural characterization of the eriodictyol 7-O-glucosyl-(1→2)-glucoside and luteolin 7-O-glucosyl-(1→2)-glucoside. The low-energy product ion mass spectrum of...

Mass spectrometric methodology based on the combined use of positive and negative electrospray ionization, collision-induced dissociation (CID) and tandem mass spectrometry (MS/MS) has been applied to the structural characterization of 6-hydroxyluteolin 7-O-glucoside and 7-O-glucosyl-(1 --> 3)-glucoside. In-source fragmentation of both glycosides a...

Objective : To investigate the in vitro antioxidant activity of the hydromethanolic extract of aerial parts (leaves and stems) of Globularia alypum L. toward linoleic acid emulsion and human low-density lipoproteins (LDL) peroxidation. Materials and Methods : Lipid peroxidation was carried out in the presence of G. alypum hydromethanolic extract (1...

Three new phenolic compounds were isolated from the aerial parts of Globularia alypum. Their structures were determined as 6-hydroxyluteolin 7-O-laminaribioside (1), eriodictyol 7-O-sophoroside (2), and 6'-O-coumaroyl-1'-O-[2-(3,4-dihydroxyphenyl)ethyl]-beta-D-glucopyranoside (3). In addition, three phenylethanoid glycosides (acteoside, isoacteosid...

The regioselective introduction of substituents at C-8 of (+)-catechin is described, leading to the synthesis of several catechin derivatives with various substitution patterns to be used for the further synthesis of modified proanthocyanidins. Thereafter, a new 3-O-4 ether-linked procyanidin-like derivative was synthesized. Its formation was selec...

A general procedure for the oxidation of catechin derivatives is described, leading to the introduction of a new hydroxy group at C-6. This procedure has been applied for the synthesis of elephantorrhizol, a natural flavan-3-ol exhibiting a fully substituted cycle A.

A xanthylium salt pigment was synthesized from the reaction involving glyoxylic acid and (+)-catechin. After isolation, its spectral characteristics and colour intensity, influenced by pH, were studied. When varying pH from acidic to alkaline values, a steady bathochromic displacement of the visible wavelength was observed while no noticeable chang...

During storage and ageing of red wine, the pigment composition becomes progressively more complex. There is a steady shift from the original red color due to the anthocyanins extracted from grapes to a more yellow tint. This is explained by the progressive and irreversible conversion of anthocyanins and of flavanols to more stable pigments, includi...

During storage and ageing of red wine, the pigment composition becomes progressively more complex. There is a steady shift from the original red color due to the anthocyanins extracted from grapes to a more yellow tint. This is explained by the progressive and irreversible conversion of anthocyanins and of flavanols to more stable pigments, includi...

The reaction between (+)-catechin and glyoxylic acid was investigated as a model system of color changes usually observed during conservation and ageing of fruit-derived foods. The reaction was monitored by LC/DAD and LC/ESI-MS analysis and the formation of various phenolic compounds initially absent in the mixture was observed.Among the detected c...

Summary Autoxidation of (+)-catechin in a model solution system, containing cupric ions, was monitored by high-performance liquid chromatography with diode array detection. The rate of (+)-catechin oxidation and the extent of browning increased with the copper concentration, showing an effect of copper on browning of flavanols. The progression of t...

The reactions between (epi)catechin, mavidin 3-O-glucoside, and some aldehydes were investigated by LC/DAD and LC/ESI-MS analysis. The obtained results showed that the acetaldehyde-mediated condensation occurred more generally and glyoxylic acid, furfural, and 5-(hydroxymethyl)furfural (HMF) react in the same way in the first stages of the reaction...

The reaction between (+)-catechin and cyanidin 3-O-glucoside was investigated in the presence of furfural and 5-(hydroxymethyl)furfural using LC/DAD and LC/MS analysis, and the obtained results were compared with those recorded with malvidin 3-O-glucoside. The appearance of colorless and red and yellow compounds was observed showing that the two po...

Various phenolic compounds were synthesized in an aqueous–alcoholic solution containing (+)-catechin and glyoxylic acid which was used as a model of fruit-derived food browning that usually occurs during aging. After purification by semi-preparative HPLC, the isolated compounds were subjected to homo- and heteronuclear proton and carbon NMR analysi...

Summary The reaction of (+)-catechin in wine-like model solution was investigated. First appearance of colourless dimeric compounds consisting of two flavanol units linked by carboxy-methine bridge was observed. Their isolation and further incubation was found to yield two types of yellowish pigments showing visible absorption maxima at 440 and 460...

(+)-catechin was separately incubated with furfural or with 5-(hydroxymethyl)furfural, and the formation of new oligomeric bridged compounds having flavanol units linked by furfuryl or 5-hydroxymethylfurfuryl groups was observed. LC/ESI-MS analyses detected four dimeric adducts along with intermediate adducts in each solution, and reaction was fast...

The reaction between (+)-catechin and glyoxylic acid in model solution system was investigated by LC/DAD and LC/ESI-MS analyses. The formation of phenolic compounds exhibiting absorption maxima near 300 nm and presenting a shoulder around 350 nm was observed. Their structures consisted of a (+)-catechin unit with one or two aldehyde groups linked a...

The reaction between (+)-catechin 1 and glyoxylic acid in model solution system was investigated by LC/DAD and LC/ESI-MS analysis and the formation of new phenolic compounds 2, 3, 4 exhibiting absorption maxima near 300 nm were observed. The structures of these compounds were elucidated by ESI-MS and 1D and 2D NMR spectroscopy.

The reaction between (+)-catechin and glyoxylic acid was studied in a model solution system. The major (+)-catechin carboxymethine-linked dimer was isolated and shown to proceed to new polyphenolic compounds exhibiting absorption maxima around 440 and 460 nm. Three yellow pigments were obtained by incubation of the 8-8 colorless isomer. One was the...

A new polyphenolic compound with a xanthylium skeleton has been synthesised from (+)-catechin and glyoxylic acid. Its structural elucidation was achieved by UV, MS and NMR spectroscopies. Its formation involved glyoxylic acid-mediated dimerisation of (+)-catechin1 giving thus compound2, followed by cyclisation to a xanthene derivative3 which by oxi...

The reactions of (+)-catechin and (-)-epicatechin in the presence of acetaldehyde were studied in model solution systems. When incubated separately with acetaldehyde and at pH values varying from 2.2 to 4. 0, reactions were faster with (-)-epicatechin than with (+)-catechin. In mixtures containing both (+)-catechin and (-)-epicatechin with acetalde...

The reaction between (-)-epicatechin, malvidin 3-O-glucoside, and acetaldehyde was studied in a model solution system. Ethyl-linked flavanol oligomers and anthocyanin-flavanol derivatives were observed, showing that the two polyphenols competed in the condensation process. Among the anthocyanin-ethyl-flavanol adducts, dimeric compounds in which the...

The reaction between (-)-epicatechin, malvidin 3-O-glucoside, and acetaldehyde was studied in a model solution system. Ethyl-linked flavanol oligomers and anthocyanin-flavanol derivatives were observed, showing that the two polyphenols competed in the condensation process. Among the anthocyanin-ethyl-flavanol adducts, dimeric compounds in which the...

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In some fruits, the loss of astringency has been attributed to the insolubilization of recombinated tannins, formed by reaction with acetaldehyde. This route has been investigated by on-line coupling of liquid chromatography with ion spray mass spectrometry (LC-ISP-MS). The results reported herein indicate that LC-ISP-MS can be successfully applied...