Dihydrochalcones with radical scavenging properties from the leaves of Syzygium jambos

Chemical investigation of the dichloromethane extract of the leaves of Syzygium jambos furnished three dihydrochalcones, phloretin 4'-O-methyl ether (2',6'-dihydroxy-4'-methoxydihydrochalcone) (1), myrigalone G (2',6'-dihydroxy-4'-methoxy-3'-methyldihydrochalcone) (2), and myrigalone B (2',6'-dihydroxy-4'-methoxy-3,5'-dimethyldihydrochalcone) (3) with radical scavenging properties towards the DPPH radical by spectrophotometric method.     

Flavanol derivatives from Rhizophora stylosa and their DPPH radical scavenging activity

A new acetylated flavanol, 3,7-O-diacetyl (-)-epicatechin (3), and seven known flavanol derivatives, (-)-epicatechin (1), 3-O-acetyl (-)-epicatechin (2), 3,3',4',5,7-O-pentaacetyl (-)-epicatechin (4), (+)-afzelechin (5), (+)-catechin (6), cinchonain Ib (7), and proanthocyanidin B2 (8), were isolated from the stems and twigs of the mangrove plant Rhizophora stylosa and identified. The crude extract, the different fractions and all of the purified compounds were evaluated for DPPH radical scavenging activity.     

Stilbene derivatives from two species of Gnetaceae

Five new stilbene oligomers (gnemonols A, B and C, gnemonoside E and gnetal) were isolated together with 2b-hydroxyampelopsin F and gnetin E from Gnetum gnemon and G. gnemonoides. The structures of the compounds were elucidated on the basis of spectral evidence.     

Synthesis and DPPH radical scavenging activity of prenylated phenol derivatives

The synthesis of twenty six prenylated phenols derivatives is reported. These compounds were obtained under mild conditions via Electrophilic Aromatic Substitution (EAS) coupling reactions between phenol derivatives containing electron-donor subtituents and 3-methyl-2-buten-1-ol using BF(3)×OEt(2). Dialkylations were also produced with this method. The formation of a chroman ring by intramolecular cyclization between a sp2 carbon from the prenyl group with the hydroxyl substituent in the ortho position occurred with some phenols. All the synthesized compounds were evaluated as antioxidants according to a DPPH radical scavenging activity assay. IC(50) values of five synthesized compounds indicated they were as good antioxidants as Trolox?.     

Cameroonian medicinal plants belonging to Annonaceae family: radical scavenging and antifungal activities

The free-radical scavenging activity of ethanolic and methanolic extracts of leaves, stems and roots of Annona muricata, Monodora tenuifolia, Uvaria comperei, Uvaria muricata and Xylopia africana was evaluated using DPPH and ORAC assays. Further, phytochemical analysis, total phenolic and total flavonoid contents were also determined. Moreover, the antifungal activity of extracts was studied. The findings indicated that A. muricata and U. comperei extracts own antiradical activities and moderate antifungal properties.     

Cytotoxic arylbenzofuran and stilbene derivatives from the twigs of Artocarpus heterophyllus

Four new natural products, including three arylbenzofurans named heterophyllenes A-C (1–3), and one stilbene named heterophyllene D (4), together with twenty-one known compounds were isolated from the twigs of Artocarpus heterophyllus and their structures elucidated by spectroscopic methods, mainly 1D and 2D NMR spectroscopy. The cytotoxic activity of selected compounds against KB, MCF-7 and NCI-H187 cell lines was evaluated. Heterophyllene C (3) exhibited cytotoxicity against the MCF-7 cell line with an IC₅₀ value of 12.56 μM. Additionally, the known compounds norartocarpin and artocarpin showed cytotoxic activity against MCF-7 and KB cell lines with IC₅₀ values of 10.04 and 13.57 μM, respectively. Both compounds also displayed cytotoxicity against the NCI-H187 cell line with values of 14.78 and 14.21 μM, respectively.     

Stilbene derivatives from Pholidota chinensis and their anti-inflammatory activity

Ethyl acetate extract of Pholidota chinensis L. showed strong NO production inhibitory activity in murine macrophage-like cell line, RAW 264.7, which was activated by a lipopolysaccharide (LPS) and interferon-gamma (IFN-gamma). Fractionation of the active extract led to the isolation of two new stilbene derivatives, 2,3'-dihydroxy-5-methoxy-3,4-methylenedioxydihydrostilbene (Pholidotol A) and 2-hydroxy-5-methoxy-3,4,3',4'-dimethylenedioxydihydrostilbene (Pholidotol B) together with six known stilbene derivatives. Pholidotols A both B and inhibited Nitric oxide (NO) production with an IC(50) value at 24.3 and 17.1 microM, respectively.     

Free radical scavenging ability of some 5-aminosalicylic acid derivatives

Theories explaining the clinically proven efficacies of 5-aminosalicylic acid and its derivatives sulfasalazine and olsalazine in the treatment of inflammatory bowel disease have invoked the neutralization or scavenging of reactive free radicals. This is a preliminary study comparing the relative scavenging abilities of these 5-ASA derivatives towards the stable free radicals 2,2-diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl with several compounds including phenols, acetaminophen and vitamins C, K and E which have well documented antioxidant and radical scavenging capabilities both in solution and in biological systems.     

Prenylated xanthones from the bark of Garcinia xanthochymus and their 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities

Garcinia xanthochymus has been widely used in traditional Chinese medicine for expelling worms and removing food toxins. Bioassay-guided fractionation of an EtOAc-soluble extract of G. xanthochymus stem bark led to the isolation of six new xanthones. Their structures were elucidated by spectroscopic methods, especially 2D-NMR techniques. Free-radical-scavenging activities of the isolated compounds were elucidated through DPPH method. Most of the isolated compounds showed considerable free radical scavenging activity on DPPH assay. Compound 1 exhibited effective antioxidant scavenging activity against DPPH radical with an IC?? value of 19.64 μM, and compound 6 showed the lowest activity among all the tested molecules, with an IC?? value of 66.88 μM. These findings support the notion that the plant genus Garcinia is a good source of bioactive compounds.     

A DFT study on the radical scavenging activity of juglone and its derivatives

The structural and electronic properties of juglone and its derivatives and their radicals were investigated at density functional level. The topology of electron density and the hydrogen bond properties of the studied structures were investigated using the Atoms in Molecules (AIM) theory. It turned out that the presence of the dihydroxy functionality increases the radical stability through hydrogen bond formation and favors hydrogen atom abstraction. The introduction of electron-donating groups for the molecules increases the activities of antioxidants. Moreover, juglone and its derivatives appear to be good candidates for the one-electron-transfer mechanism. Their planar conformation and the extended electronic delocalization between adjacent rings determine low ionization potential (IP) values, and it can be further improved by the introduction of the electron-donating groups for the molecules.     

Synthesis of water-soluble C_(60) derivatives and their scavenging free radical activity

Four piperazine-appended [60] fuilerenes (1a-1d) were synthesized and characterized. Their activities of scavenging radical were studied via UV-Vis and EPR. The results indicate that light irradiation is of advantage to increase the activity of scavenging radical.     

Swarnalin and cis-swarnalin, two new tetrahydrofuran derivatives with free radical scavenging activity, from the aerial parts of Cuscuta reflexa

The reversed-phase HPLC analysis of a methanol extract of the aerial parts of Cuscuta reflexa afforded a non-separable mixture (55 : 45) of two novel tetrahydrofuran derivatives, named swarnalin (1) and cis-swarnalin (2), and a known coumarin, 5,6,7-trimethoxycoumarin (3). The structures of the compounds were elucidated unequivocally by UV, HRFABMS and a series of 1D and 2D NMR analyses. The mixture of 1 and 2 showed significant free radical scavenging activity in the DPPH assay and the RC50 value was found to be 3.80 x 10(-4) mg mL(-1) for the mixture, compared to 2.88 x 10(-5) mg mL(-1) for the positive control, quercetin.     

Ruthenium complexes with lumazine derivatives: structural,electrochemical, computational and radical scavenging studies

In this research study, the formation and characterization of new ruthenium(II) and (III) complexes encompassing multidentate ligands derived from 6-acetyl-1,3,7-trimethyllumazine (almz) are reported. The 1:1 molar coordination reactions of trans-[RuCl₂(PPh₃)₃] with N-1-[1,3,7-trimethyllumazine]benzohydride (bzlmz) and 6-(N-methyloxime)-1,3,7-trimethyllumazine (ohlmz) formed a diamagnetic ruthenium(II) complex, cis-[RuCl₂(bzlmz)(PPh₃)] (1), and paramagnetic complex, cis-[Ru^IIICl₂(olmz)(PPh₃)] (2) [Holmz = 6-(N-hydroxy-N′-methylamino)-1,3,7-trimethyllumazine], respectively. These ruthenium complexes were characterized via physico-chemical and spectroscopic methods. Structural elucidations of the metal complexes were confirmed using single crystal X-ray analysis. The redox properties of the metal complexes were investigated via cyclic voltammetry. Electron spin resonance spectroscopy confirmed the presence of a paramagnetic metal centre in 2. The radical scavenging activities of the metal complexes were explored towards the DPPH and NO radicals. Quantum calculations at the density functional theory level provided insight into the interpretation of the IR and UV–Vis experimental spectra of 1.     

A DFT study on the radical scavenging activity of hydroxyanthraquinone derivatives in rhubarb

The structural and electronic properties of hydroxyanthraquinone derivatives in rhubarb, namely, chrysophanol, emodin, physcion, aloe‐emodin, rhein, and their radicals were investigated at density functional level. The bifurcated hydrogen bond property of the studied structures was investigated using the atoms in molecules theory. It turned out that the presence of the dihydroxy functionality increases the radical stability through hydrogen bonds formation and favors hydrogen atom abstraction. Bond dissociation energy and ionization potential were also determined to know if the radical scavenging activity of these compounds proceeds via an H‐atom or an electron‐transfer mechanism. © 2010 Wiley Periodicals, Inc. Int J Quantum Chem, 2011     

Phenylpropanoids from the stem bark of Jacaranda mimosaefolia

Two new compounds: 2-(3',4'-dihydroxyphenyl) ethyl-3-O-α-L-rhamnopyranosyl-4-O-p-hydroxyphenylacetyl-6-O-caffeoyl-β-D-glucopyranoside and 2-(3',4'-dihydroxyphenyl) ethyl-3-O-α-L-rhamnopyranosyl-4-O-piperidine-3-carboxylic acid-6-O-caffeoyl-β-D-glucopyranoside were isolated from the stem bark of Jacaranda mimosaefolia. In addition, the known compounds lupeol, betulinaldehyde, terminic acid, betulinic acid, maslinic acid, β-sitosterol glucoside and isoacteoside were isolated and identified.     

Rubescins I and J,further limonoid derivatives from the stem bark of Trichilia rubescens (Meliaceae)

Two new tetranorterpenoid derivatives named rubescins I (1) and J (2), were isolated along with six known compounds including rubescin D (3), lichexanthone (4), scopoletin (5), scopoletin O-glycoside (6), β-sitosterol (7) and stigmasterol (8) from the stem bark of Trichilia rubescens (Meliaceae). The structures of the compounds were determined by means of MS, different NMR and by comparison with related data reported in the literature.     

Bioactive constituents of the root bark of Artocarpus rigidus subsp. rigidus

Investigation of the chemical constituents of the root bark of Artocarpus rigidus BLUME subsp. rigidus has led to the isolation of six, structurally diverse phenolic compounds. These included two new compounds with modified skeletons, the flavonoid 7-demethylartonol E (1) and the chromone artorigidusin (2), together with four known phenolic compounds, the xanthone artonol B (3), the flavonoid artonin F (4), the flavonoid cycloartobiloxanthone (5), and the xanthone artoindonesianin C (6). Compounds 1, 4, and 5 exhibited antiplasmodial activity against Plasmodium falciparum. All compounds showed antimycobacterial activity against Mycobacterium tuberculosis, with 4 being the most active compound (MIC 6.25 microg/ml). Compounds 5 and 6 were active against KB cells, whereas 2, 5, and 6 showed varying toxicity to BC cells. Compounds 1-3, 5, and 6 were active in the NCI-H187 cytotoxicity assay, with 3 being the most active compound (IC(50) 1.26 microg/ml).     

In vitro anti-acne activity of phytoactives from the stem bark of Artocarpus hirsutus Lam. and characterisation of pyranocycloartobiloxanthone A as a mixture of two anomers

This study is aimed to isolate the phytoactives from the stem bark of Artocarpus hirsutus and evaluate their in vitro anti-acne activity. The ethanolic stem bark extract of A. hirsutus provided two major phytoactive constituents: (i) pyranocycloartobiloxanthone A, (1) and (ii) Artonine E, (2) whose structures were determined by NMR and MS spectroscopic analysis. The present study is the first to report compound 1 as a mixture of two anomers (α and β), approximately 70:30 ratio. Both compounds 1 and 2 were isolated for the first time from this plant. In vitro anti-acne activity of compounds 1 and 2 were evaluated by agar well diffusion method and the minimum inhibition was determined by broth micro dilution method. The result of anti-microbial activity (MIC = 2.0 μg/mL each) is comparable to antibiotic, Clindamycin (MIC = 0.03 μg/mL) and clearly demonstrate their potential as anti-acne agents.