Publication Internationale/BioTech

2016
Bensouici C, Kabouche A, Karioti A, Öztürk M, Duru ME, Bilia AR, Kabouche Z. Compounds from Sedum caeruleum with antioxidant, anticholinesterase, and antibacterial activities. Pharm. Biol. 2016;54 (1) :174–179.Abstract

Context: This is the first study on the phytochemistry, antioxidant, anticholinesterase, and antibacterial activities of Sedum caeruleum L. (Crassulaceae).

Objective: The objective of this study is to isolate the secondary metabolites and determine the antioxidant, anticholinesterase, and antibacterial activities of S. caeruleum.

Materials and methods: Six compounds (16) were isolated from the extracts of S. caeruleum and elucidated using UV, 1D-, 2D-NMR, and MS techniques. Antioxidant activity was investigated using DPPH, CUPRAC, and ferrous-ions chelating assays. Anticholinesterase activity was determined against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes using the Ellman method. Antibacterial activity was performed according to disc diffusion and minimum inhibitory concentration (MIC) methods.

Results: Isolated compounds were elucidated as ursolic acid (1), daucosterol (2), β-sitosterol-3-O-β-d-galactopyranoside (3), apigenin (4), apigetrin (5), and apiin (6). The butanol extract exhibited highest antioxidant activity in all tests (IC50 value: 28.35 ± 1.22 µg/mL in DPPH assay, IC50 value: 40.83 ± 2.24 µg/L in metal chelating activity, and IC50value: 23.52 ± 0.44 µg/L in CUPRAC), and the highest BChE inhibitory activity (IC50 value: 36.89 ± 0.15 µg/L). Moreover, the chloroform extract mildly inhibited (MIC value: 80 µg/mL) the growth of all the tested bacterial strains.

Discussion and conclusion: Ursolic acid (1), daucosterol (2), β-sitosterol-3-O-β-d-galactopyranoside (3), apigenin (4), apigetrin (5), and apiin (6) were isolated from Sedum caeruleum for the first time. In addition, a correlation was observed between antioxidant and anticholinesterase activities of bioactive ingredients of this plant.

Rezgui A, Mitaine-Offer A-C, Miyamoto T, Tanaka C, Delemasure S, Dutartre P, Lacaille-Dubois M-A. Oleanolic acid and hederagenin glycosides from Weigela stelzneri. Phytochemistry. 2016;123 :40-47.Abstract

Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin 28-O-β-D-xylopyranosyl-(1 → 6)-[α-L-rhamnopyranosyl-(1 → 2)]-β-D-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyloleanolic acid and 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 4)]-β-D-xylopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.

2015
Rezgui A, Mitaine-Offer A-C, Miyamoto T, Tanaka C, Delemasure S, Dutartre P, Lacaille-Dubois M-A. New triterpenoid saponins with cytotoxic and anti-inflammatory properties from Weigela stelzneri. Planta Medica 81(16) DOI: 10.1055/s-0035-1565571. 2015;81.Abstract

Saponins are bioactive compounds occurring in many plant species having a wide range of biological activities such as immunoadjuvant, cytotoxic, analgesic, antimicrobial and anti-inflammatory activities, just to mention a few. The aim of our researches concerns the isolation, structural elucidation and biological investigation of saponins from various plant species [1]. In this context, the study of the roots and leaves of Weigela stelzneri(Caprifoliaceae) led to isolation of four new and two known oleanane-type saponins mainly by medium pressure- and vacuum-liquid chromatography on silica gel (normal and reversed-phase RP-18) [1]. The new compounds were elucidated by a combination of spectroscopic techniques including 1D-, 2D-NMR, and mass spectrometry as glycosides of oleanolic acid, three of them being monodesmosides at C-3 with a branched oligosaccharidic chain made of six sugar units, whereas the known ones were hederagenin derivatives. The six compounds were evaluated for their cytotoxicity against a human cancer cell line (colorectal SW480) and a mouse cancer cell line (mammary EMT6), and for their anti-inflammatory activity. The results show that two new compounds differing only by the first sugar unit of the hexasaccharidic chain at C-3 (arabinopyranosyl instead of xylopyranosyl) exhibited the strongest cytotoxicity on both cell lines (IC50 5.41 µM and 1.54 µM, respectively), which was better than those of the positive controls etoposide and methotrexate. Furthermore, they revealed a significant modulatory effect of the IL-1β production on human lymphocytes stimulated with endotoxins, showing therefore a strong anti-inflammatory potential.

Rezgui A, Mitaine-Offer A-C, Pertuit D, Miyamoto T, Tanaka C, Lacaille-Dubois M-A. Spirostane-type saponins from Dracaena fragrans "Yellow Coast". Natural Product Communications (10th Anniversary issue). 2015;10 (1) :37-39.Abstract

Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. "Yellow Coast", and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.

2014
Rezgui A, Mitaine-Offer A-C, Miyamoto T, Tanaka C, Paululat T, Lacaille-Dubois M-A. New steroidal glycosides from Dracaena marginata, Dracaena fragrans and Allium flavum. Planta Medica . 2014;80 (16).Abstract

Steroidal saponins are a class of glycosides occurring in many plant species. The aglycon part of these glycosides is constituted by a furostane or spirostane-type skeleton, rarely cholestane. These saponins are known for their interesting pharmacological activities such as antifungal, anti-ischemia, antispasmodic, cytotoxic, haemolytic [1 – 3], and anti-inflammatory properties [4]. The aim of our researches was the isolation and structural elucidation of the steroidal saponins from the biodiversity. In this context, the study of three plants species, Dracaena marginataD. fragrans (Asparagaceae) and Allium flavum (Amaryllidaceae) led to isolation of twenty-one natural glycosides by column chromatography on Sephadex LH-20, medium pressure liquid chromatography and vacuum liquid chromatography on silica gel and reversed-phase RP-18 silica gel. The structures were elucidated by a detailed spectral analysis by 600 MHz 2D-NMR (COSY, TOCSY, ROESY/NOESY, HSQC, HMBC/HMQC), and mass spectrometry. Six new compounds were characterized as spirostane and furostane- type glycosides from D. marginata (1 – 3) and from A. flavum (4 – 6). The presence of a 4-O-sulfated arabinopyranosyl moiety in the oligosaccharide chain at C-1 of the steroid skeleton underlined the originality of the compounds of the two Dracaena species, and might represent a chemotaxonomic marker of the genus Dracena. The isolation and structure elucidation of the six new compounds will be presented.

Rezgui A, Mitaine-Offer A-C, Paululat T, Delemasure S, Dutartre P, Lacaille-Dubois M-A. Cytotoxic steroidal glycosides from Allium flavum. Fitoterapia. 2014;93 :121-125.Abstract

Three new spirostane-type glycosides (1-3) were isolated from the whole plant of Allium flavum. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-2α-hydroxyspirost-5-en-3β-yl O-β-D-xylopyranosyl-(1→3)-[β-D-galactopyranosyl-(1→2)]-β-D-galactopyranosyl-(1→4)-β-D-galactopyranoside (1), (20S,25R)-2α-hydroxyspirost-5-en-3β-yl O-β-D-xylopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)]-β-D-galactopyranosyl-(1→4)-β-D-galactopyranoside (2), and (20S,25R)-spirost-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-β-D-glucopyranoside (3). The three saponins were evaluated for cytotoxicity against a human cancer cell line (colorectal SW480).

2013
Bensouici C, Benmerache A, Chibani S, Kabouche A, Abuhamdah S, Z S, Kabouche Z. Antibacterial activity and chemical composition of the essential oil of Satureja calamintha ssp. sylvatica from Jijel, Algeria. Der Pharmacia Lettre. 2013;5 (2) :224-227.Abstract

The chemical composition of the hydrodistilled essential oil of Satureja calamintha ssp. sylvatica, collected from Jijel (Eastern Algerian), was analyzed by GC and GC/MS. 23 components representing 94.45% of the essential oil were detected with isopulegone (66.5%) and pulegone (11.6%) as the major components. The antibacterial activity of the essential oil was tested against 10 gram-positive and gram-negative bacteria by the use of the disc diffusion method.

Rezgui A, Mitaine-Offer A-C, Pertuit D, Miyamoto T, Tanaka C, Delemasure S, Dutartre P, Lacaille-Dubois M-A. Steroidal saponins from Dracaena marginata. Natural Product Communications. 2013;8 :157-160.Abstract

Three new steroidal saponins and ten known ones were isolated from the bark of Dracaena marginata, along with two known steroidal saponins from the roots. Their structures were elucidated on the basis of extensive 1D and 2D NMR experiments and mass spectrometry as (25R)-26-(beta-D-glucopyranosyloxy)3beta,22alpha-dihydroxyfurost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-[alpha-L-rhamnopyranosyl-(1 --> 4)]-beta-D-glucopyranoside (1), (25R)-26-(beta-D-glucopyranosyloxy)-3beta,22alpha-dihydroxyfurost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-4-O-sulfo-alpha-L-arabinopyranoside (2), and (25S)-3beta-hydroxyspirost-5-en-1beta-yl O-alpha-L-rhamnopyranosyl-(1 --> 2)-4-O-sulfo-alpha-L-arabinopyranoside (3).

2012
Chibani S, Bensouici C, Kabouche A, Aburjai T, Touzani R, Kabouche Z. Analysis of the Essential Oil of Aerial Parts of Ferula luteaPoiret from Algeria. Journal of Essential Oil Bearing Plants. 2012;15 (4) :682-685.Abstract

The essential oil obtained by hydrodistillation of fresh aerial parts of Ferula lutea Poiret (Apiaceae) was analyzed by GC and GC-MS. Twenty one compounds were characterized representing 84.9 % of the essential oil with the prevalence of 2,3,6-trimethylbenzene (25.0 %), cis-chrysanthenol (20.8 %), α-pinene (10.9 %) and thymol (10.2 %).

Chibani S, Bensouici C, Kabouche Z, Kabouche A, Al-Dabbas M-M, Aburjai T. Flavonoids and antioxidant activity of Santolina rosmarinifolia from Algeria. Chemistry of Natural Compounds. 2012;48 (5) :779–780.Abstract

Santolina is a small genus of the large subfamily Asteraceae of the family Compositae. Species of this genus are used in folk medicine as anthelmintic, antispasmodic, and antifectious agent [1]. Sesquiterpene lactones and volatile terpenes have been isolated from the Spanish subspecies S. rosmarinifolia subsp. canescens, S. rosmarinifolia subsp. rosmarinifolia, and S. chamaecyparissus [2345]. Terpenes and acetylene derivatives were reported from the roots of S. corsica [6], but no flavonoids have been reported from these two subspecies. The Algerian species S. rosmarinifolia L. [7] has not been the subject of any phytochemical study. It will be interesting to investigate the presence of 6-methoxyflavones previously reported from S. chamaecyparissus [89].

The aerial parts of S. rosmarinifolia were collected on may 2008 in the region of Batna (North Eastern Algerian) [7]. The voucher specimen was identified by Prof. Gerard De Belair (University Badji-Mokhtar, Annaba) and was...

Bensouici C, Kabouche A, Kabouche Z, Touzani R, Bruneau C. Sesquiterpene lactones and flavonoids from Centaurea foucauldiana. Chemistry of Natural Compounds, Vol. 48, No. 3, July, 2012. 2012;48 (3) :510–511.
2011
Boudiar T, Bensouici C, Safaei-Ghomi J, Kabouche A, Kabouche Z. GC- MS Analysis of Ammoides atlantica (Coss. et Dur.) Wolf. from Algeria. Journal of essential oil - bearing plants. 2011;14 (4) :481-483.Abstract

The essential oil of fresh aerial part of Ammoides atlantica Coss. et Dur. (Apiaceae), obtained by hydrodistillation in a Clevenger-type apparatus, was analyzed by GC-MS. Twenty compounds were characterized representing 97.9 % of the essential oil with safranal (17.9 %), endo-borneol (17.6 %), chrysanthenone (15.5 %), filifolone (12.1 %) and camphor (11.8 %) as main components.