Cathodic reductive coupling of methyl cinnamate on boron-doped diamond electrodes and synthesis of new neolignan-type products

• Taiki Kojima,
• Rika Obata,
• Tsuyoshi Saito,
• Yasuaki Einaga and
• Shigeru Nishiyama

Beilstein J. Org. Chem. 2015, 11, 200–203, doi:10.3762/bjoc.11.21

• interesting biological activities [1]. Due to their plausible roles as defense substances of plants, lignans, neolignans, and their congeners are promising candidates for agricultural chemicals, and some of their antioxidant and/or anti-inflammatory properties may be utilized for biological research and as

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• Taramelli 12, 27100 Pavia, Italy 10.3762/bjoc.10.331 Abstract The phytoalexin trans-resveratrol, 5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol, is a well-known, potent antioxidant having a variety of possible biomedical applications. However, its adverse physicochemical properties (low stability

• -resveratrol (5-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol; trans-3,5,4′-trihydroxystilbene, RSV) (1, Figure 1), is a triphenolic species which is known to have potent antioxidant activity and consequently a wide range of pharmacological activities [1][2]. In recent years the list of potential medicinal

• inclusion compounds as single crystals enabled their complete structural elucidation, revealing several novel supramolecular features which are relevant for future studies of the antioxidant RSV. Availability of well-defined, crystalline inclusion complexes also ensured that their characterization using

Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes

• Bodee Nutho,
• Wasinee Khuntawee,
• Chompoonut Rungnim,
• Piamsook Pongsawasdi,
• Peter Wolschann,
• Alfred Karpfen,
• Nawee Kungwan and
• Thanyada Rungrotmongkol

Beilstein J. Org. Chem. 2014, 10, 2789–2799, doi:10.3762/bjoc.10.296

• strawberries, grapes, apples, lotus roots, cucumbers and onions [6]. Fisetin has many interesting biological activities and particularly pharmacological properties, including antioxidant, anti-inflammatory, anticarcinogenic and antiviral activities [7]. It was found that fisetin can prevent oxidation which may

• understand the two flavonoids/β-CD complexes, hesperetin and naringenin complexes, in aqueous solution. The PM3 method was applied to calculate the energy regarding the antioxidant property of the flavonoid chysin in the complex with β-CD [32]. Interestingly, the molecular docking study on the fisetin/β-CD

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• graminearum Schw., Fusarium coeruleum Sacc., Botrytis cinerea Pers., and Fusarium oxysporum f. sp. cubense race 4), and Candida albicans (ATCC 10231), and the antioxidant, acetylcholinesterase (AChE) , α-glucosidase, and topoisomerase IIα inhibitory activities were performed in accordance with the primary

Superoxide chemistry revisited: synthesis of tetrachloro-substituted methylenenortricyclenes

• Basavaraj M. Budanur and
• Faiz Ahmed Khan

Beilstein J. Org. Chem. 2014, 10, 2531–2538, doi:10.3762/bjoc.10.264

• of the superoxide ion leading to the synthesis of tetrachloroaryl/vinyl-substituted nortricyclenes through its dual mode of action has been reported. KO2 was found to be superior and the only reagent to perform this kind of reaction over other conventional bases. Addition of the antioxidant BHT (2,6

• the mechanistic aspects of the reaction we have treated 3f/4f under standard conditions by using the additive radical quencher and antioxidant BHT (5 mol %) afforded the product 5f in improved yield of 94% (Scheme 3). Similarly, substrates 3c/4c and 3i/4i afforded 5c and 5i in 91% and 89% yield

Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

• Miriana Kfoury,
• David Landy,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

• ) and the solubilizing potential of CD was proposed. Molecular modeling was used to investigate the complementarities between host and guest. Finally, the antioxidant activity of encapsulated PPs was evaluated by scavenging of the stable DPPH radical. Keywords: antioxidant activity; complexation

• antioxidant activity and therefore are considered to have beneficial effects on human health [3][4]. PPs are also known to have antibacterial, antifungal and anti-inflammatory properties [5][6][7]. However, they have restricted applications as pharmaceutical products and food preservatives because they have

• presented in Figure 5. Isoeugenol (3), eugenol (4), p-coumaric acid (5), caffeic acid (6) and ferulic acid (7) presented higher antioxidant activity than trans-anethole (1) and estragole (2). It is well known that the antioxidant activity of phenolic compounds such as PPs depends mainly on the degree of

Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration

• Michele Mari,
• Simone Lucarini,
• Francesca Bartoccini,
• Giovanni Piersanti and
• Gilberto Spadoni

Beilstein J. Org. Chem. 2014, 10, 1991–1998, doi:10.3762/bjoc.10.207

• these compounds is of particular interest as 2-prenyltryptophan derivatives have been obtained or isolated from a diverse array of natural sources [66][67] and, in general, prenylation at the indole ring leads to a significant increase in the antioxidant and/or cytotoxic activity of tryptophan

Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues

• Nadezhda V. Sokolova,
• Valentine G. Nenajdenko,
• Vladimir B. Sokolov,
• Daria V. Vinogradova,
• Elena F. Shevtsova,
• Ludmila G. Dubova and
• Sergey O. Bachurin

Beilstein J. Org. Chem. 2014, 10, 155–162, doi:10.3762/bjoc.10.13

• revealed an antioxidant and mitoprotective potential of the new synthesized peptide-modified N-substituted tetrahydro-γ-carbolines. Further investigations of this class of compounds may allow finding a promising approach to cytoprotection, in particularly, neuroprotection. Conclusion In summary, we

3-Pyridinols and 5-pyrimidinols: Tailor-made for use in synergistic radical-trapping co-antioxidant systems

• Luca Valgimigli,
• Daniele Bartolomei,
• Riccardo Amorati,
• Evan Haidasz,
• Jason J. Hanthorn,
• Susheel J. Nara,
• Johan Brinkhorst and
• Derek A. Pratt

Beilstein J. Org. Chem. 2013, 9, 2781–2792, doi:10.3762/bjoc.9.313

• revision of the H-bonding basicity value of acetonitrile to β2H of 0.39. Overall, the thermodynamic and kinetic data presented here enable the design of co-antioxidant systems comprising lower loadings of the more expensive 3-pyridinol/5-pyrimidinol antioxidants and higher loadings of the less expensive

• resultant phenoxyl radical (ArO•) is sufficiently unreactive toward the substrate (RH) that it reacts with a second peroxyl radical (reaction 2 in Scheme 2), thereby breaking two oxidative chains per molecule of antioxidant – a ratio commonly referred to as the stoichiometric factor (n). However, under some

• circumstances (e.g. when diffusion of the antioxidant is impeded and it has limited opportunity to encounter other radical species), it is possible for the antioxidant-derived phenoxyl radical to propagate the chain reaction (reaction 3 in Scheme 2). The most relevant example of this is so-called ‘tocopherol

Biosynthesis of rare hexoses using microorganisms and related enzymes

• Zijie Li,
• Yahui Gao,
• Hideki Nakanishi,
• Xiaodong Gao and
• Li Cai

Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281

• -Psicose is a C-3 epimer of D-fructose and a potential sucrose substitute sweetening agent. The suppression of hepatic lipogenic enzymes activity of D-psicose has been noticed for its use as a non-caloric sweetener [25][26]. In addition, antioxidant properties have been observed for foods containing this

Raman spectroscopy as a tool for monitoring mesoscale continuous-flow organic synthesis: Equipment interface and assessment in four medicinally-relevant reactions

• Trevor A. Hamlin and
• Nicholas E. Leadbeater

Beilstein J. Org. Chem. 2013, 9, 1843–1852, doi:10.3762/bjoc.9.215

• effect on the outcome of the reaction (Table 2, entries 3 and 4). The Claisen–Schmidt condensation We moved next to study the Claisen–Schmidt condensation of benzaldehyde with acetophenone to yield chalcone (Scheme 3). Chalcones display interesting biological properties such as antioxidant, cytotoxic

Methylidynetrisphosphonates: Promising C₁ building block for the design of phosphate mimetics

• Vadim D. Romanenko and
• Valery P. Kukhar

Beilstein J. Org. Chem. 2013, 9, 991–1001, doi:10.3762/bjoc.9.114

• μM) [46]. The antioxidant activity of the compound ArC(PO3Et2)3 (Ar = 2,6-t-Bu2-4-MeC6H2) was studied in a model oxidation of oleic acid and with biological objects (liver homogenates of Wistar rats) [36]. Among polyphosphonic acids with a geminal arrangement of phosphonic groups efficient

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• focused on the reduction of these cellular pathologies. One mechanism to reduce oxidative stress in neurons is to upregulate signaling through the NF-E2-related factor 2/antioxidant response element (Nrf2/ARE) pathway, which is responsible for the upregulation of antioxidant and prosurvival genes

• significantly increased. Furthermore, primary rat neurons treated with 29 displayed an increased nuclear translocation of Nrf2 [64]. Oral treatment of transgenic SOD1 G93A mice with either 28 or 29 resulted in an increase in Nrf2 expression and nuclear localization. The levels of Nrf2-regulated antioxidant

• animals [66]. Additional work from this group identified the dopamine D2 receptor agonist, bromocriptine (32), as an NAIP upregulating compound that reduced oxidative stress through the upregulation of antioxidant proteins, such as activating transcription factor 3 (ATF3) and HO-1 [68]. In vivo studies

Zanthoxoaporphines A–C: Three new larvicidal dibenzo[de,g]quinolin-7-one alkaloids from Zanthoxylum paracanthum (Rutaceae)

• Fidelis N. Samita,
• Louis P. Sandjo,
• Isaiah O. Ndiege,
• Ahmed Hassanali and
• Wilber Lwande

Beilstein J. Org. Chem. 2013, 9, 447–452, doi:10.3762/bjoc.9.47

• , oxoaporphine and aporphine analogues have shown antimalarial, antitrypanosomal [24], cytotoxic [25], antioxidant [26] and larvicidal activities [20][21]. Despite the reported bioactivities, some of the oxoaporphines and aporphines have undesirable effects, for instance liriodenine is mutagenic [27] and induces

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• recent work, resveratrol, a polyphenolic phytoalexin present in different plant sources and which plays an important role in the prevention of many human diseases, particularly due to its antioxidant properties, was encapsulated in nanosponges. Incorporation markedly increased the solubility and

Bioactive selaginellins from Selaginella tamariscina (Beauv.) Spring

• Chao Yang,
• Yutian Shao,
• Kang Li and
• Wujiong Xia

Beilstein J. Org. Chem. 2012, 8, 1884–1889, doi:10.3762/bjoc.8.217

• -formyl-3-((4-hydroxyphenyl)ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene]cyclohexa-2,5-dien-1-one. Compound 1, 2 and 3 exhibited appreciable cytotoxic activity against cultured HeLa cells (human cervical carcinoma cells), as well as significant antioxidant activity. Keywords: antioxidant

• , tocopherols, polyphenols and tannins) are the main class of antioxidants and are known to reduce the rate of oxidation by H-transfer (from their phenol groups) to the radicals [23]. There are multiple phenol groups on the large conjugated aromatic skeleton of selaginallins, and this potential antioxidant

• structural feature motivated the study on their antioxidant activity. Accordingly, the antioxidant capacity of selaginellin O (1), selaginellin M (2) and selaginellin (3) were estimated with the widely used ABTS radical-scavenging assay and FRAP assay. In both assays, all the selaginellins tested displayed

Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin

• Christian Stanetty,
• Andrea Wolkerstorfer,
• Hassan Amer,
• Andreas Hofinger,
• Ulrich Jordis,
• Dirk Claßen-Houben and
• Paul Kosma

Beilstein J. Org. Chem. 2012, 8, 705–711, doi:10.3762/bjoc.8.79

• saponin glycyrrhizin (GL) and its aglycon glycyrrhetinic acid (GA) are the main triterpene components of licorice roots and harbor various pharmacological activities, including antitumor, anti-inflammatory, antioxidant and antiviral properties [1][2]. The antiviral activities have been reported to be

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

• Orwah Saleh,
• Katrin Flinspach,
• Lucia Westrich,
• Andreas Kulik,
• Bertolt Gust,
• Hans-Peter Fiedler and
• Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

• the first investigation of the regulatory genes of phenazine biosynthesis in Streptomyces. Keywords: phenazine; gene cluster; gene inactivation; Introduction Phenazine natural products have important biological activities comprising antibacterial, antifungal, antitumor, antimalarial, antioxidant and

Computational evidence for intramolecular hydrogen bonding and nonbonding X···O interactions in 2'-haloflavonols

• Tânia A. O. Fonseca,
• Matheus P. Freitas,
• Rodrigo A. Cormanich,
• Teodorico C. Ramalho,
• Cláudio F. Tormena and
• Roberto Rittner

Beilstein J. Org. Chem. 2012, 8, 112–117, doi:10.3762/bjoc.8.12

• (antioxidant, anti-inflammatory, antiviral, etc.) [12]. The goal of this work is to understand the intramolecular forces determining the preferred conformations of these molecules through the use of DFT theoretical calculations, quantum theory of atoms in molecules (QTAIM) [13][14][15][16][17] and natural bond

Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

• Hany M. Mohamed,
• Ashraf H. F. Abd EL-Wahab,
• Ahmed M. EL-Agrody,
• Ahmed H. Bedair,
• Fathy A. Eid,
• Mostafa M. Khafagy and
• Kamal A. Abd-EL-Rehem

Beilstein J. Org. Chem. 2011, 7, 1688–1696, doi:10.3762/bjoc.7.199

• ]. Coumarins have also been reported to exhibit several biological activities, such as antimicrobial, anticancer, antifungal, anti-HIV and antioxidant properties [3][4][5][6], and they also served as versatile precursors for many organic transformations in the synthesis of a number of drug-like molecules [7][8

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

• carvedilol has an additional antioxidant mode of action. It has been proposed that the carbazole ring may be involved in scavenging oxygen radicals thereby accounting for reduced myocardial damage [41]. Since carbazoles are similar to indoles, analogous methods can be used for their synthesis. The key

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

• Wentao Gao,
• Jia Liu,
• Yun Jiang and
• Yang Li

Beilstein J. Org. Chem. 2011, 7, 210–217, doi:10.3762/bjoc.7.28

• heterocycles, 2-heteroarylbenzofuran ring systems are widely distributed in nature and have been reported to have antiviral, antioxidant and antifungal activities [9][10][11][12][13]. For example, cicerfuran (2, Figure 1), obtained from the roots of a wild species of chickpea, Cier bijugum, was reported to be

Hoveyda–Grubbs type metathesis catalyst immobilized on mesoporous molecular sieves MCM-41 and SBA-15

• Hynek Balcar,
• Tushar Shinde,
• Naděžda Žilková and
• Zdeněk Bastl

Beilstein J. Org. Chem. 2011, 7, 22–28, doi:10.3762/bjoc.7.4

• vinyl ether, the solid catalyst was separated by centrifugation and the polymer isolated by precipitation in methanol (containing 2,6-di-tert-butyl-p-cresol as an antioxidant). The polymer yield was determined gravimetrically. The molecular weight was determined by SEC and the values related to the

Differences between β-Ala and Gly-Gly in the design of amino acids-based hydrogels

• Andreea Pasc,
• Firmin Obounou Akong,
• Sedat Cosgun and
• Christine Gérardin

Beilstein J. Org. Chem. 2010, 6, 973–977, doi:10.3762/bjoc.6.109

• acid-based amphiphiles have been received much attention in the recent past on account of their biocompatibility and eco-friendly nature. Biologically inspired His-based surfactants are of particular interest not only for their antioxidant properties and their potential therapeutic effects, but also as

An efficient partial synthesis of 4′-O-methylquercetin via regioselective protection and alkylation of quercetin

• Nian-Guang Li,
• Zhi-Hao Shi,
• Yu-Ping Tang,
• Jian-Ping Yang and
• Jin-Ao Duan

Beilstein J. Org. Chem. 2009, 5, No. 60, doi:10.3762/bjoc.5.60

• very efficient antioxidant [4] and appears to be active against many diseases related to ageing such as cancer [5], cardiovascular [6] and neurodegenerative [7] diseases. In blood, quercetin is found mainly in metabolized forms. The non-degradative metabolism of quercetin involves three main