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Molecules, Volume 16, Issue 8 (August 2011), Pages 6165-7182

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Open AccessArticle Optimized Enzymatic Synthesis of Hesperidin Fatty Acid Esters in a Two-Phase System Containing Ionic Liquid
Molecules 2011, 16(8), 7171-7182; https://doi.org/10.3390/molecules16087171
Received: 29 June 2011 / Revised: 16 August 2011 / Accepted: 17 August 2011 / Published: 23 August 2011
Cited by 11 | PDF Full-text (545 KB)
Abstract
Response surface methodology (RSM) based on a five-level, three-variable central composite design (CCD) was employed for modeling and optimizing the conversion yield of the enzymatic acylation of hesperidin with decanoic acid using immobilized Candida antarctica lipase B (CALB) in a two-phase system containing
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Response surface methodology (RSM) based on a five-level, three-variable central composite design (CCD) was employed for modeling and optimizing the conversion yield of the enzymatic acylation of hesperidin with decanoic acid using immobilized Candida antarctica lipase B (CALB) in a two-phase system containing [bmim]BF4. The three variables studied (molar ratio of hesperidin to decanoic acid, [bmim]BF4/acetone ratio and lipase concentration) significantly affected the conversion yield of acylated hesperidin derivative. Verification experiments confirmed the validity of the predicted model. The lipase showed higher conversion degree in a two-phase system using [bmim]BF4 and acetone compared to that in pure acetone. Under the optimal reaction conditions carried out in a single-step biocatalytic process when the water content was kept lower than 200 ppm, the maximum acylation yield was 53.6%. Full article
(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)
Open AccessArticle The Growth Suppressing Effects of Girinimbine on Hepg2 Involve Induction of Apoptosis and Cell Cycle Arrest
Molecules 2011, 16(8), 7155-7170; https://doi.org/10.3390/molecules16087155
Received: 18 May 2011 / Revised: 6 July 2011 / Accepted: 3 August 2011 / Published: 23 August 2011
Cited by 31 | PDF Full-text (2020 KB)
Abstract
Murraya koenigii is an edible herb widely used in folk medicine. Here we report that girinimbine, a carbazole alkaloid isolated from this plant, inhibited the growth and induced apoptosis in human hepatocellular carcinoma, HepG2 cells. The MTT and LDH assay results showed that
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Murraya koenigii is an edible herb widely used in folk medicine. Here we report that girinimbine, a carbazole alkaloid isolated from this plant, inhibited the growth and induced apoptosis in human hepatocellular carcinoma, HepG2 cells. The MTT and LDH assay results showed that girinimbine decreased cell viability and increased cytotoxicity in a dose-and time-dependent manner selectively. Girinimbine-treated HepG2 cells showed typical morphological features of apoptosis, as observed from normal inverted microscopy and Hoechst 33342 assay. Furthermore, girinimbine treatment resulted in DNA fragmentation and elevated levels of caspase-3 in HepG2 cells. Girinimbine treatment also displayed a time-dependent accumulation of the Sub-G0/G1 peak (hypodiploid) and caused G0/G1-phase arrest. Together, these results demonstrated for the first time that girinimbine could effectively induce programmed cell death in HepG2 cells and suggests the importance of conducting further investigations in preclinical human hepatocellular carcinoma models, especially on in vivo efficacy, to promote girinimbine for use as an anticancer agent against hepatocellular carcinoma. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessArticle Physico-Chemical Characteristics and Functional Properties of Chitin and Chitosan Produced by Mucor circinelloides Using Yam Bean as Substrate
Molecules 2011, 16(8), 7143-7154; https://doi.org/10.3390/molecules16087143
Received: 28 July 2011 / Accepted: 8 August 2011 / Published: 23 August 2011
Cited by 20 | PDF Full-text (426 KB)
Abstract
Microbiological processes were used for chitin and chitosan production by Mucor circinelloides (UCP 050) grown in yam bean (Pachyrhizus erosus L. Urban) medium. The polysaccharides were extracted by alkali–acid treatment and structural investigations by X-ray diffraction, Fourier transform IR analysis, viscosity and
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Microbiological processes were used for chitin and chitosan production by Mucor circinelloides (UCP 050) grown in yam bean (Pachyrhizus erosus L. Urban) medium. The polysaccharides were extracted by alkali–acid treatment and structural investigations by X-ray diffraction, Fourier transform IR analysis, viscosity and thermal analysis by TG, DTG, and DTA were done. The highest biomass yield (20.7 g/L) was obtained at 96 hours. The highest levels of chitosan (64 mg/g) and chitin (500 mg/g) were produced at 48 and 72 hours, respectively. It was demonstrated that yam bean shows great potential as an economic medium and it is possible to achieve a good yield of chitosan with chemical properties that enable its use in biotechnological applications. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Anti-Inflammatory Effect of Myristicin on RAW 264.7 Macrophages Stimulated with Polyinosinic-Polycytidylic Acid
Molecules 2011, 16(8), 7132-7142; https://doi.org/10.3390/molecules16087132
Received: 15 July 2011 / Revised: 8 August 2011 / Accepted: 18 August 2011 / Published: 22 August 2011
Cited by 36 | PDF Full-text (1056 KB)
Abstract
Myristicin (1-allyl-5-methoxy-3,4-methylenedioxybenzene) is an active aromatic compound found in nutmeg (the seed of Myristica fragrans), carrot, basil, cinnamon, and parsley. Myristicin has been known to have anti-cholinergic, antibacterial, and hepatoprotective effects, however, the effects of myristicin on virus-stimulated macrophages are not fully
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Myristicin (1-allyl-5-methoxy-3,4-methylenedioxybenzene) is an active aromatic compound found in nutmeg (the seed of Myristica fragrans), carrot, basil, cinnamon, and parsley. Myristicin has been known to have anti-cholinergic, antibacterial, and hepatoprotective effects, however, the effects of myristicin on virus-stimulated macrophages are not fully reported. In this study, the anti-inflammatory effect of myristicin on double-stranded RNA (dsRNA)-stimulated macrophages was examined. Myristicin did not reduce the cell viability of RAW 264.7 mouse macrophages at concentrations of up to 50 µM. Myristicin significantly inhibited the production of calcium, nitric oxide (NO), interleukin (IL)-6, IL-10, interferon inducible protein-10, monocyte chemotactic protein (MCP)-1, MCP-3, granulocyte-macrophage colony-stimulating factor, macrophage inflammatory protein (MIP)-1α, MIP-1β, and leukemia inhibitory factor in dsRNA [polyinosinic-polycytidylic acid]-induced RAW 264.7 cells (P < 0.05). In conclusion, myristicin has anti-inflammatory properties related with its inhibition of NO, cytokines, chemokines, and growth factors in dsRNA-stimulated macrophages via the calcium pathway. Full article
(This article belongs to the Special Issue Antivirals)
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Open AccessCommunication Azaphenanthrene Alkaloids with Antitumoral Activity from Anaxagorea dolichocarpa Sprague & Sandwith (Annonaceae)
Molecules 2011, 16(8), 7125-7131; https://doi.org/10.3390/molecules16087125
Received: 27 June 2011 / Revised: 26 July 2011 / Accepted: 4 August 2011 / Published: 22 August 2011
Cited by 9 | PDF Full-text (432 KB)
Abstract
Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments) and comparison with the literature.
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Phytochemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith led to isolation of three azaphenanthrene alkaloids: eupolauramine, sampangine and imbiline 1. Their chemical structures were established on the basis of spectroscopic data from IR, HR-ESI-MS, NMR (including 2D experiments) and comparison with the literature. Sampangine and imbiline 1 are being described in the Anaxagorea genus for the first time. Eupolauramine and sampangine show concentration-dependent antitumoral activity in leukemic cells K562 with IC50 of 18.97 and 10.95 µg/mL, respectively. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessArticle Essential Oil Composition of the Different Parts and In Vitro Shoot Culture of Eryngium planum L.
Molecules 2011, 16(8), 7115-7124; https://doi.org/10.3390/molecules16087115
Received: 22 June 2011 / Revised: 8 August 2011 / Accepted: 8 August 2011 / Published: 19 August 2011
Cited by 19 | PDF Full-text (436 KB)
Abstract
The essential oils obtained by hydrodistillation from the different parts (inflorescence, stalk leaves, rosette leaves and root) as well as from in vitro shoot culture of Eryngium planum L. were analyzed by GC-FID-MS in respect to their chemical composition. The different parts of
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The essential oils obtained by hydrodistillation from the different parts (inflorescence, stalk leaves, rosette leaves and root) as well as from in vitro shoot culture of Eryngium planum L. were analyzed by GC-FID-MS in respect to their chemical composition. The different parts of E. planum and in vitro shoots showed different yields. The part with higher amount was the inflorescences, followed by the stalk leaves and in vitro shoots, rosette leaves and finally roots. The essential oils obtained from rosette leaves and in vitro-derived rosettes had totally different composition. Quantitative differences were also found between compounds of intact plant organs. The main components of stalk leaf oil and rosette leaf oil were monoterpene (limonene, α- and β-pinene) and sesquiterpene hydrocarbons. In inflorescence oil cis-chrysanthenyl acetate (43.2%) was accompanied by other esters (propionate, butanoate, hexanoate and octanoate) and numerous oxygenated sesquiterpenes. Root oil and in vitro shoot oil contained mainly (Z)-falcarinol and 2,3,4-trimethylbenzaldehyde. This is the first report on the chemical composition of this species. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Chemical Profile and Biological Potential of Non-Polar Fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta)
Molecules 2011, 16(8), 7105-7114; https://doi.org/10.3390/molecules16087105
Received: 18 June 2011 / Revised: 3 August 2011 / Accepted: 8 August 2011 / Published: 19 August 2011
Cited by 8 | PDF Full-text (369 KB)
Abstract
The present study reports the Gas Chromatography-Mass Spectrometry (GC-MS) evaluation of the hexanes and dichloromethane fractions from extracts of the red alga Centroceras clavulatum (C. Agardh) Montagne. Twenty three compounds were identified, totaling ca. 42% of both fractions (0.18 g mass extract). The
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The present study reports the Gas Chromatography-Mass Spectrometry (GC-MS) evaluation of the hexanes and dichloromethane fractions from extracts of the red alga Centroceras clavulatum (C. Agardh) Montagne. Twenty three compounds were identified, totaling ca. 42% of both fractions (0.18 g mass extract). The main constituents of the fractions were hexadecanoic acid (17.6%) and pentadecanoic acid (15.9%). Several secondary metabolites with interesting biological activity, such as (-)-loliolide, neophytadiene, phytol were identified. In addition, several classes of secondary metabolites, including phenolic compounds (e.g., phenylacetic acid), terpene derivatives, fatty acids, halogenated compound (e.g., 2-chlorocyclohexenol), lignoids, steroids, esters, amides (e.g., hexadecanamide), ketones, carboxylic acids, aldehydes and alcohols were observed. The occurrence of several of these structural classes is described for the first time in this species. The same fractions analyzed by GC-MS, and a separate set of polar fractions, were evaluated against two life cycle stages (epimastigote and trypomastigote forms) of the protozoan Trypanosoma cruzi and against phytopatogenic fungi Cladosporium cladosporiodes and C. sphaerospermum. The dichloromethane fraction was active against both T. cruzi forms (epimastigote IC50 = 19.1 μg.mL−1 and trypomastigote IC50 = 76.2 μg.mL−1). The hexanes and ethyl acetate fractions also displayed activity against both fungi species (200 μg) by TLC-bioautography. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Alkaloids from Hippeastrum papilio
Molecules 2011, 16(8), 7097-7104; https://doi.org/10.3390/molecules16087097
Received: 9 June 2011 / Revised: 20 July 2011 / Accepted: 26 July 2011 / Published: 18 August 2011
Cited by 23 | PDF Full-text (438 KB)
Abstract
Galanthamine, an acetylcholinesterase inhibitor marketed as a hydrobromide salt (Razadyne®, Reminyl®) for the treatment of Alzheimer’s disease (AD), is obtained from Amaryllidaceae plants, especially those belonging to the genera Leucojum, Narcissus, Lycoris and Ungernia. The growing demand for galanthamine has
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Galanthamine, an acetylcholinesterase inhibitor marketed as a hydrobromide salt (Razadyne®, Reminyl®) for the treatment of Alzheimer’s disease (AD), is obtained from Amaryllidaceae plants, especially those belonging to the genera Leucojum, Narcissus, Lycoris and Ungernia. The growing demand for galanthamine has prompted searches for new sources of this compound, as well as other bioactive alkaloids for the treatment of AD. In this paper we report the isolation of the new alkaloid 11β-hydroxygalanthamine, an epimer of the previously isolated alkaloid habranthine, which was identified using NMR techniques. It has been shown that 11β-hydroxygalanthamine has an important in vitro acetylcholinesterase inhibitory activity. Additionally, Hippeastrum papilio yielded substantial quantities of galanthamine. Full article
(This article belongs to the Special Issue Alkaloids: Novel Therapeutic Perspectives)
Open AccessArticle Synthesis and Electrophilic Substitutions of Novel Pyrazolo[1,5-c]-1,2,4-triazolo[4,3-a]pyrimidines
Molecules 2011, 16(8), 7081-7096; https://doi.org/10.3390/molecules16087081
Received: 30 June 2011 / Revised: 1 August 2011 / Accepted: 4 August 2011 / Published: 18 August 2011
Cited by 4 | PDF Full-text (454 KB)
Abstract
5-Aryl-7-hydrazino-2-phenylpyrazolo[1,5-c]pyrimidines 1 were used as precursors for the preparation of a new series of 5-aryl-8-phenylpyrazolo[1,5-c]-1,2,4- triazolo[4,3-a]pyrimidines 2. The reactions of 2 with certain electrophilic reagents gave the respective 6-substituted derivatives 3-5 rather than the
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5-Aryl-7-hydrazino-2-phenylpyrazolo[1,5-c]pyrimidines 1 were used as precursors for the preparation of a new series of 5-aryl-8-phenylpyrazolo[1,5-c]-1,2,4- triazolo[4,3-a]pyrimidines 2. The reactions of 2 with certain electrophilic reagents gave the respective 6-substituted derivatives 3-5 rather than the 7-isomeric products. Formylation of the key compounds 1 with ethyl formate yielded the formyl derivatives 6. Furthermore, boiling of compounds 1 with acetic acid afforded 7-acetylhydrazino-5-aryl-2-phenylpyrazolo[1,5-c]pyrimidines 7. Bromination of 7 yielded the dibromo- derivatives 8, while their iodination and nitration gave the monosubstituted derivatives 9 and 10, respectively. Also, treatment of 1 with boiling acetic anhydride yielded the triacetyl derivatives 11. The structure of synthesized products was confirmed by elemental analyses, IR, 1H NMR and MS spectra. Full article
(This article belongs to the Special Issue Heterocycles)
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Open AccessArticle Activity and Stability Studies of Verbascoside, a Novel Antioxidant, in Dermo-Cosmetic and Pharmaceutical Topical Formulations
Molecules 2011, 16(8), 7068-7080; https://doi.org/10.3390/molecules16087068
Received: 27 June 2011 / Revised: 10 August 2011 / Accepted: 11 August 2011 / Published: 18 August 2011
Cited by 45 | PDF Full-text (451 KB)
Abstract
We here report the results of our investigations carried out on verbascoside, a phenylpropanoid glycoside known for its antioxidant, anti-inflammatory and photoprotective actions. Verbascoside was obtained from Buddleia davidii meristematic cells, obtained in turn using a sustainable biotechnology platform which employs an in
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We here report the results of our investigations carried out on verbascoside, a phenylpropanoid glycoside known for its antioxidant, anti-inflammatory and photoprotective actions. Verbascoside was obtained from Buddleia davidii meristematic cells, obtained in turn using a sustainable biotechnology platform which employs an in vitro plant cell culture technology. Verbascoside was first investigated to assess the behaviour of the active ingredient in solution or in finished preparations, in view of its potential topical use, especially in skin protection. Stability studies were performed by HPLC, and a PCL assay was adopted to determine the radical scavenging activity toward superoxide anion. The high hydrophilic character of verbascoside, suggested in a somewhat limited range of possible applications, leading us to explore its derivatization to obtain the semi-synthetic derivative VPP, an acyl derivative of verbascoside, with an improved range of applications due to its lower hydrophilic profile. Alone, VPP revealed increased antioxidant activity, both as an active ingredient and in dermocosmetic preparations. Stability studies showed a greater stability of VPP in lipophilic vehicles, whereas the parent verbascoside proved more stable in an O/W emulsions. Verbascoside was also stable in suppositories, an interesting pharmaceutical form for possible applications in treatment of inflammation of the intestinal mucosa. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessCommunication Simple and Rapid Method for the Determination of Uric Acid-Independent Antioxidant Capacity
Molecules 2011, 16(8), 7058-7067; https://doi.org/10.3390/molecules16087058
Received: 22 July 2011 / Revised: 11 August 2011 / Accepted: 15 August 2011 / Published: 17 August 2011
Cited by 28 | PDF Full-text (460 KB)
Abstract
Determination of the relative contribution of uric acid level increases to the total measured antioxidative activity could be very useful for testing antioxidative products and their effect on human health. The aim of this report is to present a simple spectrophotometric method that
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Determination of the relative contribution of uric acid level increases to the total measured antioxidative activity could be very useful for testing antioxidative products and their effect on human health. The aim of this report is to present a simple spectrophotometric method that combines the measurement of total antioxidative capacity of a sample by ferric reducing/antioxidative power (FRAP) assay, with the uricase-reaction (specific elimination of uric acid), in order to establish and correct for the contribution of uric acid in FRAP values. We measured FRAP values, with (uric acid-independent antioxidant capacity, TAC-UA) and without (total antioxidant capacity, TAC) uricase treatment, and expressed it as μmol/L of uric acid equivalents. In such way, it was possible to determine both total and uric acid-independent antioxidant capacity, plasma uric acid (UA, as the difference between TAC and TAC-UA), and the ratio of the uric acid in total antioxidant capacity (UA/TAC). Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Development of a Highly Sensitive and Specific Immunoassay for Determining Chrysoidine, A Banned Dye, in Soybean Milk Film
Molecules 2011, 16(8), 7043-7057; https://doi.org/10.3390/molecules16087043
Received: 18 July 2011 / Revised: 7 August 2011 / Accepted: 11 August 2011 / Published: 17 August 2011
Cited by 12 | PDF Full-text (765 KB)
Abstract
A highly specific and sensitive indirect competitive enzyme-linked immunosorbent assay (icELISA)was developed for the first time for the detection of chrysoidine, a dye banned in soybean milk film. Two haptens with different spacer arms were synthesized to produce antibodies. Both homologous and heterologous
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A highly specific and sensitive indirect competitive enzyme-linked immunosorbent assay (icELISA)was developed for the first time for the detection of chrysoidine, a dye banned in soybean milk film. Two haptens with different spacer arms were synthesized to produce antibodies. Both homologous and heterologous immunoassay formats were compared to enhance the icELISA sensitivity. The heterologous icELISA exhibited better performance, with an IC50 (50% inhibitory concentration) of 0.33 ng/mL, a limit of detection (LOD, 10% inhibitory concentration) of 0.04 ng/mL, and a limit of quantitation (LOQ, 20%–80% inhibitory concentration) from 0.09 to 4.9 ng/mL. The developed icELISA was high sensitive and specific, and was applied to determine chrysoidine in fortified soybean milk film samples. The results were in good agreement with that obtained by high-performance liquid chromatography (HPLC) analyses. Full article
(This article belongs to the Section Organic Chemistry)
Open AccessArticle Synthesis and Contractile Activity of Substituted 1,2,3,4-Tetrahydroisoquinolines
Molecules 2011, 16(8), 7019-7042; https://doi.org/10.3390/molecules16087019
Received: 22 July 2011 / Revised: 10 August 2011 / Accepted: 11 August 2011 / Published: 16 August 2011
Cited by 13 | PDF Full-text (510 KB)
Abstract
A series of different 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydro-isoquinolines was synthesized in high yields from different ketoamides. We have developed a convenient method for the synthesis of disubstituted derivatives by interaction of ketoamides with organomagnesium compounds, followed by cyclization in the presence of catalytic
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A series of different 1-monosubstituted and 1,1-disubstituted 1,2,3,4-tetrahydro-isoquinolines was synthesized in high yields from different ketoamides. We have developed a convenient method for the synthesis of disubstituted derivatives by interaction of ketoamides with organomagnesium compounds, followed by cyclization in the presence of catalytic amounts of p-toluenesulfonic acid (PTSA). A number of substituents at the C-1 in the isoquinoline skeleton were introduced varying either carboxylic acid or organomagnesium compound. Some of the obtained 1,1-dialkyl-1,2,3,4-tetrahydro-isoquinolines possess contractile activity against guinea pig’s gastric smooth muscle preparations. Full article
(This article belongs to the Special Issue Heterocycles)
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Open AccessArticle Antiviral Properties of Lactoferrin—A Natural Immunity Molecule
Molecules 2011, 16(8), 6992-7018; https://doi.org/10.3390/molecules16086992
Received: 23 July 2011 / Revised: 5 August 2011 / Accepted: 10 August 2011 / Published: 16 August 2011
Cited by 67 | PDF Full-text (453 KB)
Abstract
Lactoferrin, a multifunctional iron binding glycoprotein, plays an important role in immune regulation and defence mechanisms against bacteria, fungi and viruses. Lactoferrin’s iron withholding ability is related to inhibition of microbial growth as well as to modulation of motility, aggregation and biofilm formation
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Lactoferrin, a multifunctional iron binding glycoprotein, plays an important role in immune regulation and defence mechanisms against bacteria, fungi and viruses. Lactoferrin’s iron withholding ability is related to inhibition of microbial growth as well as to modulation of motility, aggregation and biofilm formation of pathogenic bacteria. Independently of iron binding capability, lactoferrin interacts with microbial, viral and cell surfaces thus inhibiting microbial and viral adhesion and entry into host cells. Lactoferrin can be considered not only a primary defense factor against mucosal infections, but also a polyvalent regulator which interacts in viral infectious processes. Its antiviral activity, demonstrated against both enveloped and naked viruses, lies in the early phase of infection, thus preventing entry of virus in the host cell. This activity is exerted by binding to heparan sulphate glycosaminoglycan cell receptors, or viral particles or both. Despite the antiviral effect of lactoferrin, widely demonstrated in vitro studies, few clinical trials have been carried out and the related mechanism of action is still under debate. The nuclear localization of lactoferrin in different epithelial human cells suggests that lactoferrin exerts its antiviral effect not only in the early phase of surface interaction virus-cell, but also intracellularly. The capability of lactoferrin to exert a potent antiviral activity, through its binding to host cells and/or viral particles, and its nuclear localization strengthens the idea that lactoferrin is an important brick in the mucosal wall, effective against viral attacks and it could be usefully applied as novel strategy for treatment of viral infections. Full article
(This article belongs to the Special Issue Antivirals)
Open AccessArticle Synthesis of New Riminophenazines with Pyrimidine and Pyrazine Substitution at the 2-N Position
Molecules 2011, 16(8), 6985-6991; https://doi.org/10.3390/molecules16086985
Received: 11 July 2011 / Revised: 6 August 2011 / Accepted: 9 August 2011 / Published: 16 August 2011
Cited by 4 | PDF Full-text (477 KB)
Abstract
New riminophenazines with pyrimidine and pyrazine substituents at the 2-position were successfully synthesized. The key step is the 2-N-arylation of riminophenazines with pyrimidine and pyrazine. The optimized reaction conditions involve the use of a Pd2(dba)3/DPPF/Cs2CO3/toluene combination. Full article
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