Anti-Inflammatory and Analgesic Effect of Arachic Acid Ethyl Ester Isolated from Propolis.

Inflammatory diseases are a real public health problem worldwide. Many synthetic drugs used in the treatment of inflammatory diseases such as steroidal anti-inflammatory drugs, nonsteroidal anti-inflammatory drugs (NSAIDs) and immunosuppressive drugs have harmful side effects. However, there are natural products like propolis, which is traditionally used in the treatment of pain. The objective of this work was to evaluate the anti-inflammatory and analgesic activities of the ethyl ester of arachic acid, a compound isolated from Cameroonian propolis. The ethyl ester of arachic acid was isolated by chromatography of the ethanolic extract of propolis harvested at Tala-Mokolo (Far North Region of Cameroon) and identified by nuclear magnetic resonance (NMR) spectra and the 1H-1H correlated spectroscopy. The anti-inflammatory and analgesic properties of oral administration of arachic acid ethyl ester (12.5, 25.0, and 50.0 mg/kg bw) were evaluated using carrageenan-induced paw edema, xylene-induced ear edema, cotton pellets-induced granuloma formation, and hot plate test in rat. Arachic acid ethyl ester produced maximum inhibition at 50.0 mg/kg for carrageenan-induced paw edema (62.5%), xylene-induced ear edema (54.5%), cotton pellet-induced granuloma (47.4%), and increased mean latency for hot plate test in rats. These results show clearly that the arachic acid ethyl ester has acute and chronic anti-inflammatory properties as well as central analgesic properties. This justifies the use of propolis in the treatment of pain in traditional medicine.

Excelsanone, a new isoflavonoid from Erythrina excelsa (Fabaceae), with in vitro antioxidant and in vitro cytotoxic effects on prostate cancer cells lines.

A new isoflavonoid, excelsanone (2), was isolated from the ethyl acetate extract of Erythrina excelsa stem bark, together with three known compounds namely 6,8-diprenylgenistein (3), ß-sitosterol (1) and sitosteryl-ß-D-glucopyranoside (4). Their structures were elucidated using spectroscopic methods (HR-ESI-MS, NMR and IR) and by comparison with some literature data. The antioxidant activity of crude extracts and two isolated compounds was evaluated using free radical scavenging (DPPH) and Ferric Reducing Ability Power (FRAP) methods with catechin as standard. The results of the radical scavenging activity showed that excelsanone (2) has a moderate potential with an IC50 of 1.31 mg/ml. The cytotoxicity of compounds 2 and 3 as well as the ethyl acetate extract was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in two prostate cancer cell lines (DU145 and PC3). Excelsanone (2) induced a greater cytotoxicity in all tested cell lines, with a significant inhibition of DU145 cells growth in a concentration-dependent manner.

New mono-ether of glycerol and triterpenes with DPPH radical scavenging activity from Cameroonian propolis.

The extracts of some propolis samples were analysed by GC-MS and then purified by column chromatography. The latter led to the isolation of a new mono-ether of glycerol, 1'-O-eicosanyl glycerol and a new triterpene, methyl-3ß,27-dihydroxycycloart-24-en-26-oate together with known triterpenoids namely betulin, 3ß-hydroxylanostan-9,24-dien-21-oic acid, mangiferonic acid, a mixture of ambolic acid and ß-sitosterol, 3ß-hydroxycycloartan-12,24(25)-diene and 27-hydroxymangiferonic acid. The DPPH radical scavenging potential of some extracts and compounds were measured. The radical scavenging activity varied from Hexane extract of Foumban propolis (IC50 = 5.6 mg/mL) to Methanol extract of Foumban propolis (IC50 = 1.07 mg/mL) for the extracts and from 3ß-hydroxylanostan-9,24-dien-21-oic acid (IC50 = 1.22 mg/mL) to 1'-O-eicosanyl glycerol (IC50 = 0.93 mg/mL) for the compounds. Activities of samples were moderate as they remained closer to those of the standard antioxidants Gallic acid (IC50 = 0.30 mg/mL) and vitamin C (IC50 = 0.80 mg/mL), especially 1'-O-eicosanyl glycerol, the most active compound.

New prenylated isoflavonoids as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Erythrina addisoniae.

Bioassay-guided fractionation of the EtOAc extract of the root of Erythrina addisoniae (Leguminosae) resulted in the isolation of four new (1-4), along with 2 known prenylated isoflavonoids (5-6). The structures of the isolates were assigned on the basis of spectroscopic data analysis, focusing on interpretation of 1D and 2D NMR, and MS data. All the isolates were evaluated for their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B), as well as their growth inhibition on MCF7, adriamycin-resistant MCF7 (MCF7/ADR), and MDA-MB-231 breast cancer cell lines. Compounds which exhibited PTP1B inhibitory activity (IC(50) values ranging from 4.6 ± 0.3 to 24.2 ± 2.1 µM) showed potential cytotoxic activity (IC(50) values ranging from 3.97 ± 0.17 to 11.4 ± 1.9 µM). Taken together, our data suggest that prenylated isoflavonoids, especially the isoflavone-type skeleton could be considered as new lead compounds against breast cancer via PTP1B inhibition.

Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica.

Bioassay-guided fractionation of the EtOAc extract of the stem bark of Erythrina abyssinica (Leguminosae) resulted in the isolation of three new (1-3), along with 12 known (4-15) pterocarpan derivatives. Their chemical structures were determined by physicochemical and spectroscopic data analysis (IR, UV, [alpha](D), CD, 1D and 2D NMR, and MS data). All the isolates were evaluated for their inhibitory effects on protein tyrosine phosphatase-1B (PTP1B), as well as their growth inhibition on MCF7, tamoxifen-resistant MCF7 (MCF7/TAMR), adriamycin-resistant MCF7 (MCF7/ADR) and MDA-MB-231 breast cancer cell lines. Compounds which exhibited PTP1B inhibitory activity (IC(50) values ranging from 4.2+/-0.2 to 19.3+/-0.3 microM) showed strong cytotoxic activity (IC(50) values from 5.6+/-0.7 to 28.0+/-0.2 microM). Our data suggested that pterocarpans could be considered as new anticancer materials by PTP1B inhibition.

Four new chalcones from Erythrina abyssinica.

Four new chalcones 1 - 4, named abyssinones A - D, were isolated from the stem bark of the plant Erythrina abyssinica and their structures were elucidated on the basis of spectroscopic analyses. The compounds 1, 3, and 4 were found to exhibit moderate cytotoxic activity against the human colorectal cancer cell line (Caco2) with IC (50) values of 13.3, 15.1, and 11.1 microM, respectively.

Inhibitory effect of 2-arylbenzofurans from Erythrina addisoniae on protein tyrosine phosphatase-1B.

Bioassay-guided fractionation of an EtOAc-soluble extract of the stem bark of Erythrina addisoniae (Leguminosae), using an in vitro PTP1B inhibitory assay, resulted in the isolation of three new (1-3) and three known (4-6) 2-arylbenzofuran derivatives. The new compounds were identified as 2-[2',4'-dihydroxy-3'-(3-methylbut-2-enyl)phenyl]-6-hydroxybenzofuran (1), 2-[2'-methoxy-4'-hydroxy-5'-(3-methylbut-2-enyl)phenyl]-6-hydroxybenzofuran (2), and 2-(2'-methoxy-4'-hydroxyphenyl)-5-(3-methylbut-2-enyl)-6-hydroxybenzofuran (3). The new 2-arylbenzofurans 1-3 inhibited PTP1B activity with IC(50) values ranging from 13.6+/-1.1 to 17.5+/-1.2 microM in vitro assay. On the basis of the data obtained, 2-arylbenzofurans with prenyl group may be considered as a new class of PTP1B inhibitors.

Warangalone, the isoflavonoid anti-inflammatory principle of Erythrina addisoniae stem bark.

The prenylisoflavone warangalone has been isolated from the bark of Erythrina addisoniae. This compound, previously recognized as a powerful inhibitor of protein kinase A, showed marked effectiveness as an anti-inflammatory on the phospholipase A(2)-induced paw edema and on the 12-O-tetradecanoylphorbol 13-acetate-induced ear edema in mice, after systemic and local administration, respectively.