ABSTRACT
Phytochemical investigation of the methanol extract from the fruits of Macaranga monandra (Euphorbiaceae Muell. et Arg.) afforded one new geranylated 1',2'-dihydrophenanthrene and two new flavonoid derivatives, named macamondrin (1), macamondrione A (2) and B (3) respectively. The structures of these compounds were elucidated mainly by NMR, mass spectral data and in comparison with data from the literature. Along with compounds 1-3, nine known compounds among which oleanolic acid (4); daucosterol (5); 3ß-acetoxy-11α,12α-epoxytaraxerol (6); 3,3',4-tri-O-methylellagic acid (7); 3,3',4,4'-tetra-O-methylellagic acid (8); 4'-O-methyl-6-isoprenylapigenin (9); 4'-O-methyl-8 isoprenylkaempférol (10); 4'-O-methyl-6-isoprénylkaempférol (11); 6-isoprénylkaempférol (12), were also isolated. Crude extracts as well as isolated compounds were evaluated for their antioxidant activity using the ABTS, DPPH and FRAP methods. It appears that the 50 % radical scavenging concentrations ranging from 6.26 to 11.7â µg/ml on the ABTS radical, from 1.77 to 48.22â µg/ml on the DPPH radical, and from 1.54 to 67.97â µg/ml with the FRAP method. For the compounds tested, very good antioxidant activities were observed, which clearly shows that these molecules can have an anti oxidative stress potentiel.
Subject(s)
Antioxidants , Euphorbiaceae , Fruit , Polyphenols , Antioxidants/pharmacology , Antioxidants/chemistry , Antioxidants/isolation & purification , Fruit/chemistry , Polyphenols/chemistry , Polyphenols/isolation & purification , Polyphenols/pharmacology , Euphorbiaceae/chemistry , Biphenyl Compounds/antagonists & inhibitors , Picrates/antagonists & inhibitors , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Extracts/isolation & purificationABSTRACT
The coupling reaction of diazonium ion of 2-amino-6-nitrobenzothiazole at 0-5 °C with distinctly substituted 2-aminobenzothiazole derivatives produced new 1,2,3,5-tetrazine derivatives. It was found that diazotized 2-amino-6-nitrobenzo[d]thiazol reacts with the ring nitrogen atom of varyingly substituted 2-aminobenzothiazole derivatives to yield tetrazine nucleus. The benzene ring of benzothiazole bearing electron donor group and annelated to the tetrazine was further substituted in situ by other 6-nitrobenzo[d]thiazol-2-yl) diazinyl to yield the final product. The structure of the prepared compounds was elucidated using their physical, elemental, and spectroscopic data. The synthesized compounds were tested for their antimicrobial and antibiofilm activities against Staphylococcus aureus and Escherichia coli bacteria. Two of the synthesis tetrazine derivatives exhibited interesting antibiofilm potential.
Subject(s)
Anti-Bacterial Agents , Benzothiazoles , Biofilms , Escherichia coli , Microbial Sensitivity Tests , Staphylococcus aureus , Biofilms/drug effects , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemical synthesis , Staphylococcus aureus/drug effects , Escherichia coli/drug effects , Benzothiazoles/pharmacology , Benzothiazoles/chemistry , Benzothiazoles/chemical synthesis , Diazonium Compounds/chemistry , Diazonium Compounds/pharmacologyABSTRACT
Background Alcoholic liver disease (ALD) is regarded as a global health problem with limited therapeutic options. Previous studies highlighted some anticancer, antiviral, and hepatoprotective activities of limonoids, but the effects of these compounds on ALD remain unknown. The present study aimed to evaluate the effect of some natural limonoids on ethanol-induced liver injury. Methods Thirty-five albino mice (Mus musculus) were administered with 40% ethanol in the presence or absence of the different limonoids [including three havanensin-type limonoids, TS1, TS3, Rubescin D isolated from an African medicinal plant, Trichilia rubescens Oliv. (Meliaceae), and one limonin], or silymarin at 50 mg/kg for 3 days. Thereafter, the effect of the most active compound was evaluated in a chronic model of ALD. For this purpose, 24 mice with each group consisting of six mice were administered orally with 40% ethanol and limonoid at different doses (50, 75, and 100 mg/kg) for 28 days. Finally, biochemical parameters such as alanine aminotransferase (ALT), superoxide dismutase (SOD), catalase (CAT), malondialdehyde (MDA), triglyceride (TG), and tumor necrosis factor α (TNF-α) levels were quantified in liver homogenates. Results All tested limonoids significantly (p < 0.01) reduced ALT levels relative to the negative control in the acute model. However, in comparison to other limonoids, limonin at 50 and 75 mg/kg significantly reduced TG, MDA, and TNF-α levels (1.8-fold); alleviated leukocyte infiltration in liver tissue; significantly increased the activity of SOD; and decreased those of CAT better than silymarin used as a positive control at 50 mg/kg. Conclusions These data suggest that limonin possesses protective effects on long-term alcohol poisoning partially due to antioxidant and anti-inflammatory mechanisms.
