Pharmacological evaluation of the semi-purified fractions from the soft coral Eunicella singularis and isolation of pure compounds

Abstract

BackgroundGorgonians of the genus Eunicella are known for possessing a wide range of pharmacological activities such as antiproliferative and antibacterial effect. The aim of this study was to evaluate the anti-inflammatory and gastroprotective effect of the organic extract and its semi-purified fractions from the white gorgonian Eunicella singularis and the isolation and identification of pure compound(s) from the more effective fraction.MethodsAnti-inflammatory activity was evaluated, using the carrageenan-induced rat paw edema test and in comparison to the reference drug Acetylsalicylate of Lysine. The gastroprotective activity was determined using HCl/EtOH induced gastric ulcers in rats. The purification of compound(s) from the more effective fraction was done by two chromatographic methods (HPLC and MPLC). The structure elucidation was determined by extensive spectroscopic analysis (1H and 13C NMR, COSY, HMBC, HMQC and NOESY) and by comparison with data reported in the literature.ResultsThe evaluation of the anti-inflammatory activity of different fractions from Eunicella singularis showed in a dependent dose manner an important anti-inflammatory activity of the ethanol fraction, the percentage of inhibition of edema, 3 h after carrageenan injection was 66.12%, more effective than the reference drug (56.32%). In addition, this ethanolic fraction showed an interesting gastroprotective effect compared to the reference drugs, ranitidine and omeprazol. The percentage of inhibition of gastric ulcer induced by HCl/ethanol in rats was 70.27%. The percentage of the reference drugs (ranitidine and omeprazol) were 65 and 87.53%, respectively. The purification and structure elucidation of compound(s) from this ethanolic fraction were leading to the isolation of five sterols: cholesterol (5α-cholest-5-en-3β-ol) (1); ergosterol (ergosta-5,22-dien-3β-ol) (2); stigmasterol (24-ethylcholesta-5,22-dien-3b-ol) (3); 5α,8α-epidioxyergosta 6,22-dien-3β-ol (4) and 3β-hydroxy-5α,8α-epidioxyergosta-6-ene (5); and one diterpenoid: palmonine D (6).ConclusionBased on data presented here, we concluded that diterpenoids and sterols detected in the ethanolic fraction can be responsible for its pharmacological activity.Electronic supplementary materialThe online version of this article (doi:10.1186/s40199-014-0064-7) contains supplementary material, which is available to authorized users.

Anticancer activity of diterpenes and steroids from Eunicella singularis against two- and threedimensional breast cancer cell models

“…Crude extract was fractionated into three semi-purified fractions were purified from F-EtOH fraction as described previously [22,23]. using InCyte ® software package.…”

Secondary Metabolites from Gorgonian Corals of the Genus Eunicella: Structural Characterizations, Biological Activities, and Synthetic Approaches

“…The organic extracts of the coral were prepared by maceration and were examined for the presence of several class of compounds, i.e., polyphenols, alkaloids, saponins, steroids, terpenoids, and glycosides by qualitative chemical From 2013 to 2017, Deghrigue's group and Ioannou's group conducted thorough studies on E. singularis and Eunicella cavolini comprising preliminary biological evaluation of the organic extracts and fractions. It was found that the polar fractions show anti-inflammatory and analgesic potentials, as well as anti-proliferative effects on breast cancer cells MCF-7 and prostate cancer cells LNCaP, indicating the presence of novel bioactive compounds [19,[29][30][31][32]. The organic extracts of the coral were prepared by maceration and were examined for the presence of several class of compounds, i.e., polyphenols, alkaloids, saponins, steroids, terpenoids, and glycosides by qualitative chemical screening tests based on visible chemical change [29,31].…”

“…The organic extracts of the coral were prepared by maceration and were examined for the presence of several class of compounds, i.e., polyphenols, alkaloids, saponins, steroids, terpenoids, and glycosides by qualitative chemical screening tests based on visible chemical change [29,31]. Final purification of fractions resulted in isolation of 2 terpenoids, palmonines D (5) and F (7), and nine steroids of various chemical structures (Section 2.3., vide infra) [30,32]. Moreover, Rosa et al first isolated diterpenoid 8 bearing two acetoxyl groups, from the E. cavolini acetone extract ( Figure 5) [21].…”

Synthesis and Biological Activities of Novel 1,7-dihydropyrazolo[3,4-d]imidazo[1,2-f]pyrimidines

“…Oral administration of the damaging agent to the control group clearly produced a mucosal damage characterized by multiple haemorrhage red bands of different sizes along the long axis of the glandular stomach [9].…”

“…After 30 min, gastric damage was induced in the experimental groups by 150 mM HCl/EtOH (40:60, v/v) orally administration (1 mL/100 g), while the control group received vehicle and the reference group received ranitidine (60 mg/ kg, i.p). One hour later, the animals were sacrificed and their stomachs rapidly removed and opened via an incision along the greater curvature [9]. Gastric damage was determined by measuring the extent of the ulcerative lesions.…”