<i>N</i>-Methylisosalsoline from <i>Hammada scoparia</i>

Jarraya, Raoudha; Bouaziz, Amira; Hamdi, Besma; Salah, Abdelhamid Ben; Damak, Mohamed

doi:10.1107/s160053680802477x

Cited by 15 publications

(9 citation statements)

References 11 publications

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“…Our results are in agreement with other works that indicated the richness of Haloxylon scoparium in alkaloids; Zerriouh and collaborators reported that the aerial part of Hammada scoparia collected in Algeria contains the alkaloids [39]. In addition, Jarraya and collaborators described the isolation and structural elucidation of N-methylisososaloline extracted from Haloxylon scoparium leaves collected in Tunisia [40].…”

Section: Phytochemical Screeningsupporting

confidence: 92%

Mineral Composition, Phenolic Content, and In Vitro Antidiabetic and Antioxidant Properties of Aqueous and Organic Extracts of Haloxylon scoparium Aerial Parts

Lachkar

Lamchouri

Bouabid

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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Haloxylon scoparium is a plant widely used in traditional medicine for the treatment of diabetes. Hence, this study focuses on the mineralogical and chemical composition and evaluation of the antidiabetic and antioxidant activities of the aerial part of this species. The mineralogical analysis was done by inductively coupled plasma atomic emission spectrometry (ICP-AES). The phytochemical study consisted in the preparation of different extracts from the aerial part by aqueous and organic extraction using Soxhlet and cold maceration. Then, phytochemical screening was performed on the plant powder and on the extracts, which is completed by spectrophotometric quantification of total polyphenols, flavonoids, and catechic tannins. The evaluation of antidiabetic activity was done by three enzymes: a-amylase, a-glucosidase, and ß-galactosidase, and that of antioxidant activity was done by five methods: H2O2, DPPH, ABTS, FRAP, and reducing power (RP). Mineralogical analysis revealed the presence of iron, potassium, magnesium, phosphorus, sodium, copper, calcium, strontium, selenium, and zinc. The studied part is rich in alkaloids, flavonoids, catechic tannins, and saponins. The methanolic extract is rich in total polyphenols (161.65 ± 1.52 Ug EAG/mg E), and the ethyl acetate extract has high levels of catechic tannins (23.69 ± 0.6 Ug EC/mg E). In addition, the decoctate expresses a high flavonoid content of 306.59 ± 4.35 Ug EQ/mg E. The in vitro evaluation of the antidiabetic activity showed that the decoctate has a higher inhibitory capacity on a-glucosidase (IC50 = 181.7 ± 21.15 ug/mL) than acarbose (IC50 = 195 ± 6.12 ug/mL). The results of the antioxidant activity showed that the methanolic extract and the decoctate present a percentage of hydrogen peroxide (H2O2) scavenging (20.91 ± 0.27 and 16.21 ± 0.39%) higher than that of ascorbic acid (14.35 ± 0.002%). Positive correlations obtained between the total polyphenol content and the antioxidant activity of the extracts were studied. A positive correlation of a-amylase inhibitory activity was also recorded with the antioxidant activity tests.

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Section: Phytochemical Screeningsupporting

confidence: 92%

Mineral Composition, Phenolic Content, and In Vitro Antidiabetic and Antioxidant Properties of Aqueous and Organic Extracts of Haloxylon scoparium Aerial Parts

Lachkar

Lamchouri

Bouabid

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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“…The residue (5 g) was separated, on column chromatography over silica gel using a gradient of dichloromethane-methanol to give N-methylisosalsoline (545 mg) as white rosette crystals. The data of the 1 H-NMR spectra matched those reported in the literature [40].…”

Section: Extraction Of N-methylisosalsolinesupporting

confidence: 76%

Synthesis of C3/C1-Substituted Tetrahydroisoquinolines

et al. 2015

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Abstract:A broad biological screening of the natural alkaloid N-methylisosalsoline (2) extracted from Hammada scoparia leaves against a panel of human and parasitic proteases revealed an interesting activity profile of 2 towards human 20S proteasome. This outcome suggests that the 1,2,3,4-tetrahydroisoquinoline skeleton may be exploited as a template for the development of novel anticancer agents. In this article, we report the synthesis and chemical characterization of a new series of isosalsoline-type alkaloids (10-11) with variations at N2 and C3 positions with respect to the natural Compound 2, obtained by a synthetic strategy that involves the Bischler-Napieralski cyclization. The substrate for the condensation to the tetrahydroisoquinoline system, i.e., a functionalized β-arylethyl amine, was obtained through an OPEN ACCESSMolecules 2015, 20 14903 original double reduction of nitroalkene. The synthetic strategy can be directed to the construction of highly substituted and functionalized 1,2,3,4-tetrahydroisoquinolines.

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“…In fact, the AE significantly boosted the antioxidant enzyme activities, which could be explained by the presence of many phenolic compounds having a potent antiradical activity in comparison with ascorbic acid and BHT. In fact, we previously isolated some phenolic alkaloids (N-methylisosalsoline, 1-methylisosalsolinol and dopamine) and flavonoids (quercetin, isorhamnetin and quercetin 3-O-robinobioside) from the AE of H. scoparia (Jarraya et al, 2005(Jarraya et al, , 2008. A new flavonol triglycoside, isorhamnetin 3-O-b-D-xylopyranosyl-(1 00 !3)-a-L-rhamnopyranosyl-(1!6 00 )-b-D-galactopyr anoside, has been isolated from the leaves of H. scoparia together with two known compounds, iso-rhamnetin3-O-b-D-apiofuranosyl-(1!2 00 )[a-L-rhamno pyranosyl-(1 00 !6 00 )]-b-D-galacto pyranoside and isorhamnetin 3-O-a-L-rhamnopyranosyl-(1!2 00 )[a-L-rha mnopyranosyl-(1 00 !6 00 )]-b-D-galactopyranoside (Ben Salah et al, 2002).…”

Section: Discussionmentioning

confidence: 99%

Protective effects of aqueous extract ofHammada scopariaagainst hepatotoxicity induced by ethanol in the rat

et al. 2012

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Aqueous extract (AE) of Hammada scoparia leaves was chemically characterized and its hepatoprotective activities were investigated in vivo in rat model. Wistar rats were treated daily with 35% ethanol solution (3 g/kg/day) during 4 weeks and fed with basal diet or basal diet containing AE (200 mg/kg/day). Control rats were treated with saline solution and fed with basal diet. The bioactivity of AE against ethanol-induced oxidative stress in rat liver was studied in order to explore its hepatoprotective effects. H. scoparia extract used at 200 mg/kg body weight significantly prevented the effects of ethanol, which induced a hepatic pathological damage and increased the levels of the serum markers of the enzymes such as alanine aminotransferase (ALT), aspartate aminotransferase (AST) and alkaline phosphatase (ALP). Concomitantly, with these changes, this extract also prevented ethanol-induced oxidative stress in the rat liver as evidenced by the decreased lipid peroxidation level, a considerable decrease in the activities of AST, ALT and ALP and restoring the activities of antioxidant enzymes: superoxide dismutase, catalase and glutathione peroxidase. These biochemical changes were consistent with histopathological observations suggesting marked hepatoprotective effect of the AE of H. scoparia.

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N-Methylisosalsoline from Hammada scoparia

Cited by 15 publications

References 11 publications

Mineral Composition, Phenolic Content, and In Vitro Antidiabetic and Antioxidant Properties of Aqueous and Organic Extracts of Haloxylon scoparium Aerial Parts

Mineral Composition, Phenolic Content, and In Vitro Antidiabetic and Antioxidant Properties of Aqueous and Organic Extracts of Haloxylon scoparium Aerial Parts

Synthesis of C3/C1-Substituted Tetrahydroisoquinolines

Protective effects of aqueous extract ofHammada scopariaagainst hepatotoxicity induced by ethanol in the rat

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