Manuela Oliverio

Manuela Oliverio
Universita' degli Studi "Magna Græcia" di Catanzaro | Università Magna Græcia di Catanzaro · Department of Health Sciences

Ph.D

About

88
Publications
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Introduction
My research activity has been mainly focused on green manipulation of biologically active molecules and on exploiting chemical and agricultural waste as platform for fine chemicals, playing attention to the use of reusable-non toxic catalysts, solvent free conditions, US and MW energy, Q-tube reactors to improve the processes environmental compatibility. About catalysis my reserch interest is to exploit salts of Er(III) as Lewis acids in homogeneous and heterogeneous phase, in bach and in flow.

Publications

Publications (88)
Article
In this work we investigate the synthesis of alanine from lactic acid, a biobased platform chemical, using ammonia as a nitrogen source and Ru/zeolite catalysts. We report a high alanine selectivity when using Ru/BEA of 80-93%. Reaction side products were identified as ethanol, propionic acid or propanamide and the reaction mechanism was investigat...
Article
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The benzimidazole ring of the heterocyclic pharmacophores is one of the most widespread and studied systems in nature. The benzimidazole derivative synthesis study is a crucial point for the development of a clinically available benzimidazole-based drug. Here, we report a simple microwave assisted method for the synthesis of 1,2-disubstituted benzi...
Preprint
A microwave assisted method for synthesis of 2-substituted benzimidazoles has been developed. The combination of molar ratio N-phenyl-o-phenylenediamine:benzaldehyde (1:1) using microwave irradiation and only 1% mol of Er(OTf)3 provide an efficient, environmental and mild access to a diversity of benzimidazoles under solvent-free conditions.
Article
Polyphenols from olive oil are endowed with several biological activities. Chemical modifications have been recently applied to these compounds to improve their therapeutic activity in different pathological settings, including cancer. Herein, we describe the in vitro effects on multiple myeloma (MM) cells of oleil hydroxytyrosol (HTOL), a syntheti...
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It is well-accepted that the endogenous antioxidant protection system progressively decays in elderly people, and that the oxidative stress contributes to different neurodegenerative disorders such as Alzheimer’s Diseases (AD). The lower incidence of AD in countries which feature the Mediterranean Diet was associated to the high consumption of extr...
Article
Chemocatalytic conversion of cellulose into lactic acid is a valuable alternative to simple sugar fermentation. Nevertheless, the procedures still need optimization to be translated to the industrial scale. Such translation would benefit by on-line monitoring of reaction parameters by fast, inexpensive, direct spectroscopic techniques. In this work...
Article
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Covering: 2005 up to 2020 Olive bioactive secoiridoids are recognized as natural antioxidants with multiple beneficial effects on human health. Nevertheless, the study of their biological activity has also disclosed some critical aspects associated with their application. Firstly, only a few of them can be extracted in large amounts from their natu...
Article
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The worldwide increased difficulty to counteract gastrointestinal nematode (GIN) infection in sheep, due to progressing anthelmintic resistance, has led to the evaluation of other alternative helminth control options, mainly from plants. The anthelmintic efficacy of an aqueous Punica granatum macerate was evaluated in sheep naturally infected by GI...
Article
Similarity and competition between multicomponent reactions with similar mechanisms and leading to similar scaffolds can be a useful tool for medicinal chemistry. In this review, we have summarized the studies disclosing the mechanism of such competition between the Biginelli and Hantzsch reactions. We focused our attention in particular on those s...
Article
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Cellulose is the main component of lignocellulosic biomass. Its direct chemocatalytic conversion into lactic acid (LA), a powerful biobased chemical platform, represents an important, and more easily scalable alternative to the fermentative way. In this paper, we present the selective hydrothermal conversion of cellulose and simple sugars into LA,...
Article
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The exploitation and use of alternative synthetic methods, in the face of classical procedures that do not conform to the ethics of green chemistry, represent an ever-present problem in the pharmaceutical industry. The procedures for the synthesis of benzimidazoles have become a focus in synthetic organic chemistry, as they are building blocks of s...
Preprint
Full-text available
The exploitation and use of alternative synthetic methods, in the face of classical procedures that do not conform to the ethics of Green Chemistry, represent an ever present problem in pharmaceutical industry. The procedures for the synthesis of benzimidazoles have become a focus in synthetic organic chemistry, as they are building blocks of stron...
Article
Full-text available
Olive oil contains different biologically active polyphenols, among which oleacein, the most abundant secoiridoid, has recently emerged for its beneficial properties in various disease contexts. By using in vitro models of human multiple myeloma (MM), we here investigated the anti-tumor potential of oleacein and the underlying bio-molecular sequela...
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A simple and eco-friendly montmorillonite K10 (MK10)-catalyzed method for the synthesis of cyclopentenone derivatives from biomass-produced furfural has been developed. The versatility of this protocol is that the reactions were performed under solvent-free conditions and in a short reaction time under heterogeneous catalysis. Montmorillonite K10 i...
Preprint
A simple and eco-friendly Montmorillonite K10 (MK10) catalyzed method for the synthesis of cyclopentenone derivatives from biomass-produced furfural has been developed. The versatility of this protocol is that the reactions were carried out in solvent free condition and in short reaction time under heterogeneous catalysis. Montmorillonite K10 is a...
Article
We synthesized a series of small symmetrical unsaturated disulfides by a multi-step reaction starting from organic alcohols, and we performed a preliminary test to evaluate the effect of these compounds on the viability of A549 lung cancer cells. The garlic-derived natural compound diallyl disulfide, known for its anticancer activity, was used as t...
Article
Phenolic compounds present in extra virgin olive oil have recently attracted considerable attention due to their pharmacological activities. Among them oleacein (3,4-DHPEA-EDA), structurally related to oleochantal (4-HPEA-EDA), is one of the most studied. 3,4-DHPEA-EDA has been synthesized through decarboxylation of demethyloleuropein catalyzed by...
Article
The biological activities of oleuropein (Ole) and its metabolites have extensively been documented and shown a spectrum of highly interesting bioactivities which prove the potential of oleuropein for inclusion into food and beverages. In the present work, acetylated oleuropein (OleAc), a safe, biologically active semi-synthetic stable derivative of...
Article
Thioacetates as precursors of thiols, are interesting starting point to synthesize other organosulfur compounds. Herein, we propose a simple, efficient and fast method to obtain organic thioacetates using water as a solvent. Taking into account the great attention which has been put on environmentally friendly synthetic procedures in the last decad...
Article
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Epigallocatechin gallate (EGCG) was structurally modified to obtain EGCG fatty acid esters using an eco-friendly method employing Er(OTf)3 in 2-MeTHF as the catalyst. The products were purified in short times on a large scale using VERSAFLASH HTFP station on octadecyl-functionalized silica gel. The same Lewis acid showed to be a good catalyst for t...
Article
The first example of the use of ammonia, the waste material of the bulk glycerol carbonate (GC) production, for the formation of another valuable organic molecule, a 1,4-dihydropyridine (1,4-DHP), by an in line two reactor system was presented. Two Q-tube reactors, one for the urea glycerolysis and the other for the Hantzsch reaction, were used, co...
Article
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The development of novel synthetic routes to produce bioactive compounds starting from renewable sources has become an important research area in organic and medicinal chemistry. Here, we present a low-cost procedure for the tunable and selective conversion of biomass-produced furfuraltocyclopentenonederivativesusingamixtureofcholinechlorideandurea...
Article
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Bergamot Polyphenol Fraction (BPF®) is a natural mixture of Citrus flavonoids extracted from processed bergamot fruits. It has been shown to counteract cardiovascular risk factors and to prevent liver steatosis in rats and patients. Hepatic effects of BPF correlate with its ability to stimulate liver autophagy. Six aglyconic flavonoids have been id...
Article
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Acetylcholinesterase inhibitors were introduced for the symptomatic treatment of Alzheimer’s disease (AD). Among the currently approved inhibitors, donepezil (DNP) is one of the most preferred choices in AD therapy. The X-ray crystal structures of Torpedo californica AChE in complex with two novel rigid DNP-like analogs, compounds 1 and 2, have bee...
Article
Autophagy dysfunction has been implicated in the pathogenesis of non-alcoholic fatty liver disease (NAFLD). Natural compounds present in Bergamot Polyphenol Fraction (BPF) prevent NAFLD and induce autophagy in rat livers. Here, we employed HepG2 cells expressing DsRed-LC3-GFP, a highly sensitive model system to screen for proautophagic compounds pr...
Article
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Green catalysts must be non-toxic, easy to manage, able to be recovered and reused, active under alternative reaction conditions and cheap. Erbium salts meet all the previously listed characteristics and today they are emerging as a valuable catalytic solution to a number of organic transformations needing a Lewis acid catalyst in wet conditions or...
Article
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Oleuropein is the most important phenolic compound present in olive cultivars, but it is scarcely present in extra virgin olive oil (EVOO) due to its high hydrophilicity and degradability. Thus, a set of oleuropein aglycone derivatives were synthesized by transacetylation under mild conditions with the aim of circumventing these drawbacks and makin...
Article
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It is of great significance to develop sustainable processes of catalytic reaction. We report a selective procedure for the synthesis of acetylated bioactive compounds in water. The use of 1-acetylimidazole combined with Er(OTf)3 as a Lewis acid catalyst gives high regioselectivity and good yields for the acetylation of primary hydroxyl groups, as...
Article
In an ideal plasmonic surface sensor, the bioactive area, where analytes are recognized by specific biomolecules, is surrounded by an area that is generally composed of a different material. The latter, often the surface of the supporting chip, is generally hard to be selectively functionalized with respect to the active area. As results, cross tal...
Preprint
It is of great significance to develop sustainable processes of catalytic reaction. We report an efficient and selective procedure for the synthesis of acetylated bioactive compounds in water. The use of 1-acetylimidazole combined with Er(OTf)3 as Lewis acid catalyst gives high regioselectivity and good to excellent yields for the acetylation of pr...
Article
Full-text available
Oleuropein (OLE) is the major phenolic secoiridoid of olive tree leaves, and its antioxidant and anti-inflammatory activities have been demonstrated in in vitro and in vivo animal models. The aim of this study was to investigate the activity of OLE in the colonic mucosa from patients with ulcerative colitis (UC). Biopsies obtained during colonoscop...
Article
Er(OTf)3 in 2-MeTHF provides a new and eco-friendly process for Ferrier glycosylation of sulfonamides and amino acids with various N-nucleophiles. The stereoselective synthesis of 2,3-unsaturated-N-pseudoglycals was carried out with 3,4,6-tri-O-acetyl-d-glucal and different nucleophiles affording good results in a short time.
Conference Paper
Full-text available
Background: Interleukin (IL)-17 is a pleiotropic cytokine which acts on both immune and non-immune cells and is over-expressed in a number of inflammatory disorders, including ulcerative colitis (UC). Treatment with Oleuropein (OLE), the major phenolic secoiridoid of olive tree leaves, has been found to inhibit Th17 response in a DSS-induced mouse...
Article
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Background: The peracetylation is a simple chemical modification that can be used to enhance the bioavailability of hydrophilic products and to obtain safe and stable pro-drugs. Results: A totally green, solvent-free and catalyst-free microwave (MW)-assisted method for peracetylation of natural products such as oleuropein, alpha-hederin, quercetin...
Data
Scaled oleuropein peracetylation procedure, GC?MS, LC?HRMS, 1H and 13C NMR spectra of new compounds, as well as calculation for green chemistry metrics.
Article
Full-text available
An ecofriendly synthetic pathway for the synthesis of donepezil precursors is described. Alternative energy sources were used for the total synthesis in order to improve yields, regioselectively, and rate of each synthetic step and to reduce the coproduction of waste at the same time. For all products, characterized by an improved structural rigidi...
Article
Titanium dioxide (TiO2) is a well-known biocompatible material with important applications in many fields of biomedicine. Here we show our results on the development of a new TiO2 based sol-gel system that can act as negative tone resist for both ultraviolet (UV) and electron beam (EB) lithographies. The system allows the direct patterning of high...
Article
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The potential of Fourier transform near-infrared reflectance spectroscopy (FT-NIRS) to predict the organic loading on hybrid organic-inorganic mesoporous silica was studied. Fourty nine samples of MCM-41 functionalized silica were used to built and cross-calibrate a partial least squared (PLS) model, based on the comparison between NIR spectra and...
Article
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A new “on water” MW-assisted esterification protocol using fatty chlorides and acetonidehydroxytyrosol as starting materials, giving rise to a one-pot multistep reaction, without any added catalyst is described. The reaction took place at the interface oil/water thus being strictly dependent on the lipophilicity of the fatty acid acyl chloride. The...
Article
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Heterogeneous bifuctional catalysts are multifunctional synthetic catalysts enabling efficient organic transformations by exploiting two opposite functionalities without mutual destruction. In this paper we report the first Er(III)-based metallorganic heterogeneous catalyst, synthesized by post-calcination MW-assisted grafting and modification of t...
Article
Catalysis in aqueous systems under sonochemical conditions has become an irreplaceable method in green synthetic chemistry after more than two decades of studies in this domain. The present review has the aim of describing the state-of-the-art with a comprehensive view of advantages and limitations as well as new potential applications. Catalytic p...
Article
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In this paper is presented a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambid...
Article
Full-text available
The high consumption of olive tree products in the Mediterranean diet has been associated with a lower incidence of metabolic disorders and cardiovascular diseases. In particular, the protective effects of olive oil have been attributed to the presence of polyphenols such as oleuropein (Ole) and its derivatives. We have synthesized a peracetylated...
Article
Phenolic compounds present in extra virgin olive oil have attracted considerable recent attention. Many of them, show specific anti-inflammatory and anti-tumor activities. In this work we describe the biomimetic synthesis of 3,4-DHPEA-EDA [2-(3,4-hydroxyphenyl) ethyl (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate], starting from natural demethyloleuro...
Article
Full-text available
1-Indanones have been successfully prepared by means of three different non-conventional techniques, namely microwaves, high-intensity ultrasound and a Q-tube™ reactor. A library of differently substituted 1-indanones has been prepared via one-pot intramolecular Friedel-Crafts acylation and their efficiency and "greenness" have been compared.
Article
In this paper, a Q-tube equipment is proposed as a valid alternative to monomode MW technology to synthesize in a simple and economic way a library of dihydropyrimidine derivatives performing the Biginelli reaction in solvent-free conditions under pressure and with the catalysis of a very mild and environmentally benign Lewis acid consisting of erb...
Article
Full-text available
Hybrid materials obtained through a Microwave-assisted grafting of organic functional groups on mesoporous silica (MCM-41 type) have been characterized by X-ray powder diffraction, TG-DSC, N2 adsorption, solid state 13C- and 29Si-NMR, TEM and SEM. The studied grafting procedure is effective in the preparation of hybrid organosilicas under solvent-f...
Chapter
Full-text available
Investigation of the biological effects of olive oil/leaf/fruit phenolic extracts and, more recently, of the isolated compounds oleuropein and hydroxytyrosol has revealed their health beneficial action opening the way for a potential pharmacological utilization as single drug or after enrichment of olive oil or other food component. After a brief d...
Article
Full-text available
The olive tree phenolic components oleuropein and its derivatives have shown many biological properties, so representing promising novel therapeutics for the treatment of several diseases, including neoplasia. In this study we evaluated the activities of oleuropein (OLE) and its peracetylated derivative (peracetylated oleuropein, Ac-OLE), against t...
Article
Full-text available
Erbium(III) chloride in ethyl lactate is used as an environmentally very friendly system for the reaction of furfural and amines to yield diastereoselectively differently N,N-substituted trans-4,5-diaminocyclopent-2-enones as versatile synthetic intermediates to the formation of densely functionalized derivatives.
Article
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The first catalyst-free and on-water method for tosylation of alcohols is presented. Tosylation can be realized in a few minutes under microwave-assistance, exploiting the water insolubility of reagents and products as the driving force of the reaction. A biodegradable water solution of p-toluenesulfonic acid is the only waste produced.
Article
A simple one-pot two-step synthesis affords the target compounds as inhibitors of hepatitis C virus NS5B polymerase.
Article
A simple and efficient method for the synthesis of wide range of 3,3-dimethyl-11-alkyl or aryl 2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepin-1- ones, recently reported as hepatitis C virus (HCV) NS5B polymerase inhibitors, is presented. The proposed method consists of one-pot condensation between 1,2-phenylenediamine and 5,5-dimethylcyclohexane-1...
Article
Hydroxytyrosol is a potent antioxidant natural molecule isolated from olive leaves and fruits. The presence of three hydroxy groups in its structure poses a limit for the topical application of this lead compound. A set of hydroxytyrosol conjugates with fatty acids at different molecular weights were synthesized under mild conditions. The topical d...