Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• , antioxidant, antiprotozoal, antiviral and immunobiological activities (reviewed in [1][2]). Two SLs remarkable for their immunobiological potential are archangelolide (1) and trilobolide (2), depicted in Figure 1. Compound 2 exhibits strong induction of nitric oxide (NO) in eukaryotic cells, which in turn

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• cerebral injection of lipopolysaccharide endotoxin, with some compounds showing antioxidant and antineuroinflammatory activities. The same group employed this 4CR with cholestan-3-one for the construction of 2-amino-3-cyanodihydropyridine scaffold fused to ring A of the cholestane system [45]. Also

Synthesis of polydicyclopentadiene using the Cp₂TiCl₂/Et₂AlCl catalytic system and thin-layer oxidation of the polymer in air

• Zhargolma B. Bazarova,
• Ludmila S. Soroka,
• Alex A. Lyapkov,
• Мekhman S. Yusubov and
• Francis Verpoort

Beilstein J. Org. Chem. 2019, 15, 733–745, doi:10.3762/bjoc.15.69

• through the layers. Consequently, this leads to the transition of the oxidation from a kinetic mode into a diffusive mode. Such structural changes do not occur in a polymer that was stabilized by adding an antioxidant. Keywords: bis(cyclopentadienyl)titanium dichloride; cationic polymerization; oxidation

• occur in the polymer which was stabilized by adding an antioxidant (Agidole-1 in the amount of 0.2% by mass). The infrared spectrum of the thin layer of the stabilized polymer (Figure 17a) does not change and no consumption of double bonds in the polymer can be detected (Figure 17b). Conclusion This

• mode into a diffusion one. These structural changes do not occur in a polymer stabilized by adding an antioxidant in the studied period of time. Experimental Dehydrated toluene, prepared according to a well-known procedure, was used as a solvent [30]. Polymerization of DCPD in toluene was carried out

Synthesis of the aglycon of scorzodihydrostilbenes B and D

• Katja Weimann and
• Manfred Braun

Beilstein J. Org. Chem. 2019, 15, 610–616, doi:10.3762/bjoc.15.56

• highly oxygenated aryl rings. Scorzodihydrostilbene E (5) features a dimeric skeleton that originates from an oxidative coupling of compound 1. The natural products exhibited antioxidative activity that was partly stronger than that of the well-known naturally occurring antioxidant resveratrol [5]. In

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

• Jacqueline Pollini,
• Valentina Bragoni and
• Lukas J. Gooßen

Beilstein J. Org. Chem. 2018, 14, 2737–2744, doi:10.3762/bjoc.14.252

• display a broad range of biological activities such as antimicrobial [23], antioxidant [24], molluscicidal [25] and antiplaque [26]. Ginkgolic acids, structurally closely related analogues of anacardic acid, have been reported to exhibit tyrosinase inhibitory activity [27]. We herein report a concise

Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

• Robby Vroemans,
• Yenthel Verhaegen,
• My Tran Thi Dieu and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2689–2697, doi:10.3762/bjoc.14.246

• equivalent nitroalkene, 1.2 equivalents of salicylaldehyde and 0.1 equivalents of DABCO as catalyst in the first step at 40 °C, and 2 equivalents of benzyl azide, 2 equivalents of acetic acid, 0.3 equivalents of BHT as antioxidant, 4 Å MS and DMF under argon atmosphere at 120 °C in the second step. Crude NMR

Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers

• Christian Schütz and
• Martin Empting

Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241

• effects are mediated either through direct PqsR-dependent action or by PqsR-independent mechanisms, which are most likely due to the iron-chelating as well as antioxidant properties of PQS [33]. Furthermore, it has been unravelled that the thioesterase PqsE, whose biosynthetic function is dispensable due

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

• ][36]. Purpurogallin (8), which is biogenetically produced by oxidation of pyrogallol, and its analogues (like 9) are natural pigments (Figure 1) [37][38][39][40][41][42][43][44]. Theaflavin (10) and its derivatives, named theaflavins, are antioxidant benzotropones that are formed by the enzymatic

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• , dihydrofuranocoumarins are another class of coumarins possessing anticancer activities. Recently, Ahmadi et al. identified several dihydrofuranocoumarins, especially grandivittin (GRA), from Ferulago macrocarpa (Fenzl) Boiss., and their mechanism of minor groove DNA binding and antibacterial, cytotoxic and antioxidant

Continuous-flow retro-Diels–Alder reaction: an efficient method for the preparation of pyrimidinone derivatives

• Imane Nekkaa,
• Márta Palkó,
• István M. Mándity and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2018, 14, 318–324, doi:10.3762/bjoc.14.20

• antibiotics [41]. Our aim in the present study was to synthesize functionalized pyrimidinone systems through rDA reactions. Many of these products are of high importance in drug design due to their diverse biological properties including antimicrobial, antiviral, antioxidant and antitumor activities. In

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

• pharmacological activities such as: anticancer [1][2], anti-inflammatory [3][4], antioxidant [5], antibacterial [6][7][8], analgesic [9], antiviral [10][11], antimicrobial [12][13], antifungal [6], antiglycemic [14], antiamoebic [15] and antidepressive [16][17]. Considering the immense biological properties

• ], protein kinase inhibitors [32], antiallergic [33], antioxidant [34] and as fungicide [35]. Also, the pyrazolo[3,4-b]pyridine ring system is a key structure in drug discovery and has become the main component in many medicinally important compounds. The large number of synthetic routes to pyrazolo[3,4-b

Synthesis of naturally-derived macromolecules through simplified electrochemically mediated ATRP

• Paweł Chmielarz,
• Tomasz Pacześniak,
• Katarzyna Rydel-Ciszek,
• Izabela Zaborniak,
• Paulina Biedka and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2017, 13, 2466–2472, doi:10.3762/bjoc.13.243

• solution to receive functionalised polymers. It is a naturally occurring flavonoid, which is abundantly found in citrus fruits, herbs, vegetables, seeds, tea, nuts, and red wine [24][25][26]. It is considered to be a strong antioxidant due to its ability to scavenge free radicals and bind transition metal

• ions [27]. Quercetin inhibits xanthine oxidase [27][28][29], inhibits lipid peroxidation in vitro [27][28][30], and scavenges oxygen radicals [27][28][31][32][33]. There is a tremendous importance of this antioxidant in the prevention of a range of cardiovascular diseases [27][34][35], cancer [26][27

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

• Elisandra Scapin,
• Paulo R. S. Salbego,
• Caroline R. Bender,
• Alexandre R. Meyer,
• Anderson B. Pagliari,
• Tainára Orlando,
• Geórgia C. Zimmer,
• Clarissa P. Frizzo,
• Helio G. Bonacorso,
• Nilo Zanatta and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 2396–2407, doi:10.3762/bjoc.13.237

• the pharmaceutical field due to their significant potential to exhibit antitumor, antimicrobial, and antioxidant activities [1][2]. In addition to acting as a stimulant of the central nervous system [3], this class of substances plays an important role in drugs that are used to treat obesity, diabetes

Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage

• Henning Weiss,
• Jeannine Reichel,
• Helmar Görls,
• Kilian Rolf Anton Schneider,
• Mathias Micheel,
• Michael Pröhl,
• Michael Gottschaldt,
• Benjamin Dietzek and
• Wolfgang Weigand

Beilstein J. Org. Chem. 2017, 13, 2264–2272, doi:10.3762/bjoc.13.223

• curcuma longa, and its analogues, the curcuminoids, have attracted much attention regarding their biological activities [1]. These include antioxidant [2] and radical scavenging [3], antitumor [4] and anti-inflammatory [5] activities, as well as HIV inhibition [6]. Despite showing activity against several

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• ‘‘Molecular Physical-Chemistry – QFM-UC”, University of Coimbra, 3004-535 Coimbra, Portugal Department of Life Sciences, University of Coimbra, 3000-456 Coimbra, Portugal 10.3762/bjoc.13.212 Abstract Fisetin is a natural antioxidant with a wide range of nutraceutical properties, including antidiabetic

• using elemental analysis, powder X-ray diffraction (PXRD), Raman, infrared and 13C{1H} CP-MAS NMR spectroscopies, and thermal analysis (TGA) to verify fisetin inclusion and to present a hypothetical structural arrangement for the host–guest units. The antioxidant activity of the γ-CD·fisetin inclusion

• compound is evaluated by the DPPH assay. Keywords: antioxidant activity; co-lyophilization; fisetin; gamma-cyclodextrin; molecular encapsulation; solid-state analysis; Introduction Flavonoids, natural compounds with numerous beneficial actions on human health, including antioxidant [1], anti-inflammatory

Selective enzymatic esterification of lignin model compounds in the ball mill

• Ulla Weißbach,
• Saumya Dabral,
• Laure Konnert,
• Carsten Bolm and
• José G. Hernández

Beilstein J. Org. Chem. 2017, 13, 1788–1795, doi:10.3762/bjoc.13.173

• antioxidant, antibacterial and sun protection properties [17][23][24]. Motivated by the aforementioned scenario and in line with our research interest on studying the compatibility of biocatalysts and mechanochemical milling, we decided to investigate the enzymatic esterification of lignin model compounds in

• addressing the centrally-located primary aliphatic hydroxyl content of lignins is still highly possible. This strategy is expected to allow the preservation of the phenolic and benzylic alcohol contents in modified lignins, in order to keep the antibacterial and antioxidant activities of this biopolymer

Use of costic acid, a natural extract from Dittrichia viscosa, for the control of Varroa destructor, a parasite of the European honey bee

• Kalliopi Sofou,
• Demosthenis Isaakidis,
• Apostolos Spyros,
• Anita Büttner,
• Athanassios Giannis and
• Haralambos E. Katerinopoulos

Beilstein J. Org. Chem. 2017, 13, 952–959, doi:10.3762/bjoc.13.96

• essential oil were found active against Staphylococcus epidermidis, Streptococcus foecalis and Proteus vulgaris [36]. The methanol extract of the aerial parts of the plant showed antioxidant activity in a study on lipid peroxidation of rat liver microsomes [30]. n-Hexane extracts from air dried D. viscosa

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

• Gabriel P. Costa,
• Natália Seus,
• Juliano A. Roehrs,
• Raquel G. Jacob,
• Ricardo F. Schumacher,
• Thiago Barcellos,
• Rafael Luque and
• Diego Alves

Beilstein J. Org. Chem. 2017, 13, 694–702, doi:10.3762/bjoc.13.68

• -(phenylselanylmethyl)-1,2,3-triazole A (Se-TZ) demonstrated an antidepressant-like effect (Figure 1) [60]. In another example, 5-phenyl-1-(2-(phenylselanyl)phenyl)-1H-1,2,3-triazole-4-carbonitrile B (Se-TZCN) was reported to exhibit antioxidant activities in different in vitro assays (Figure 1) [36]. Selenanyl-quinone

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

• Viktor Ilkei,
• András Spaits,
• Anita Prechl,
• Áron Szigetvári,
• Zoltán Béni,
• Miklós Dékány,
• Csaba Szántay Jr,
• Judit Müller,
• Árpád Könczöl,
• Ádám Szappanos,
• Attila Mándi,
• Sándor Antus,
• Ana Martins,
• Attila Hunyadi,
• György Tibor Balogh,
• György Kalaus (†),
• Hedvig Bölcskei,
• László Hazai and
• Tibor Kurtán

Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247

• increase P-gp inhibitory activity [18]. Based on the unaltered accumulation of rhodamine 123, a P-gp substrate fluorescent dye, in the P-gp transfected L5178MDR cells, we observed that none of the synthesized compounds inhibits this transporter. The antioxidant activity of dracocephins A and B was also

Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products

• Manuela Oliverio,
• Paola Costanzo,
• Monica Nardi,
• Carla Calandruccio,
• Raffaele Salerno and
• Antonio Procopio

Beilstein J. Org. Chem. 2016, 12, 2222–2233, doi:10.3762/bjoc.12.214

• ester (8), uridine (12) and methyl-α-D-glucopyranoside (11)) and natural antioxidant compounds in their simple (hydroxytyrosol (4), homovanillic alcohol (5), quercetin (13)) or glycosylated forms (oleuropein (14), rutin (17), alpha-hederin (16)). Because of their heterogeneity in terms of

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• 180 μL of DPPH· was recorded as ADPPH·, and the absorbance of the 200 μL of MeOH was measured as Ablank. The natural antioxidant vitamin C was used as a positive control. Calculations of the DPPH· scavenging activity was performed according to the following equation: scavenging activity (%) = [1

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• -inflammatory and antioxidant effects of J. paniculata were associated to the presence of flavonoids and other polyphenols [4]. Recently, we reported the in vivo anti-inflammatory properties of an aqueous fraction of the leaves of J. sellowii, that is in agreement with its popular use in Brazil [5]. Apart from

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• chestnut) showed antioxidant activity [28]. Testing urolithins A, B, C, D (23–26) in an assay using myelomonocytic HL-60 cells showed antioxidant activities for 23, 25 and 26. These three derivatives inhibited the reactive oxygen species (ROS)-dependent oxygenation of the non-fluorescent 2’,7

• ’-dichlorodihydrofluorescein (DCFH) to the fluorescent 2’,7’-dichlorofluorescein (DCF) [29]. This antioxidant activity was also linked to anti-inflammatory effects by testing the in vivo effects of 23 in a carrageenan-induced paw edema assay. Oral administration of 23 to mice prior to carrageenan injection resulted in a

A selective and mild glycosylation method of natural phenolic alcohols

• Mária Mastihubová and
• Monika Poláková

Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51

• phenylpropenyl) glycosides having a free phenolic function at the para-position of the aglycone are substances widely occurring in plants. They exhibit numerous biological activities which are in many cases related to their structure–antioxidant activity relationship. 4-Hydroxy-3-methoxybenzyl β-D

Thermal and oxidative stability of Atlantic salmon oil (Salmo salar L.) and complexation with β-cyclodextrin

• Daniel I. Hădărugă,
• Mustafa Ünlüsayin,
• Alexandra T. Gruia,
• Cristina Birău (Mitroi),
• Gerlinde Rusu and
• Nicoleta G. Hădărugă

Beilstein J. Org. Chem. 2016, 12, 179–191, doi:10.3762/bjoc.12.20

• natural antioxidants are flavonoids, anthocyanins and their glycosides. Huber and collaborators [18] revealed the inhibition of PUFA oxidation by quercetin and its 3-O-glucoside. They were as effective as butylated hydroxytoluene (BHT, a synthetic antioxidant) against the oxidation of DHA and methylated

• during the process of fish oil production leads to improved stability up to 400% [22]. Smoking the pink salmon before the oil extraction process was another method for reducing the oxidation by forming phenolic antioxidant compounds [23][24]. Another way to stabilize fish oil is microencapsulation using