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Molecules, Volume 19, Issue 5 (May 2014), Pages 5459-6910

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Open AccessReview Circulating miRNAs as Biomarkers for Neurodegenerative Disorders
Molecules 2014, 19(5), 6891-6910; https://doi.org/10.3390/molecules19056891
Received: 19 April 2014 / Revised: 19 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
Cited by 57 | PDF Full-text (281 KB) | HTML Full-text | XML Full-text
Abstract
Neurodegenerative disorders, such as Alzheimer’s disease (AD), Parkinson’s disease (PD) and frontotemporal dementias (FTD), are considered distinct entities, however, there is increasing evidence of an overlap from the clinical, pathological and genetic points of view. All neurodegenerative diseases are characterized by neuronal loss
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Neurodegenerative disorders, such as Alzheimer’s disease (AD), Parkinson’s disease (PD) and frontotemporal dementias (FTD), are considered distinct entities, however, there is increasing evidence of an overlap from the clinical, pathological and genetic points of view. All neurodegenerative diseases are characterized by neuronal loss and death in specific areas of the brain, for example, hippocampus and cortex for AD, midbrain for PD, frontal and temporal lobes for FTD. Loss of neurons is a relatively late event in the progression of neurodegenerative diseases that is typically preceded by other events such as metabolic changes, synaptic dysfunction and loss, neurite retraction, and the appearance of other abnormalities, such as axonal transport defects. The brain’s ability to compensate for these dysfunctions occurs over a long period of time and results in late clinical manifestation of symptoms, when successful pharmacological intervention is no longer feasible. Currently, diagnosis of AD, PD and different forms of dementia is based primarily on analysis of the patient’s cognitive function. It is therefore important to find non-invasive diagnostic methods useful to detect neurodegenerative diseases during early, preferably asymptomatic stages, when a pharmacological intervention is still possible. Altered expression of microRNAs (miRNAs) in many disease states, including neurodegeneration, and increasing relevance of miRNAs in biofluids in different pathologies has prompted the study of their possible application as neurodegenerative diseases biomarkers in order to identify new therapeutic targets. Here, we review what is known about the role of miRNAs in the pathogenesis of neurodegeneration and the possibilities and challenges of using these small RNA molecules as a signature for neurodegenerative conditions. Full article
(This article belongs to the Special Issue miRNAs as Probes to Monitor Cancer and Neurodegenerative Disorders)
Open AccessArticle Two-Stage Prediction of the Effects of Imidazolium and Pyridinium Ionic Liquid Mixtures on Luciferase
Molecules 2014, 19(5), 6877-6890; https://doi.org/10.3390/molecules19056877
Received: 20 March 2014 / Revised: 15 May 2014 / Accepted: 19 May 2014 / Published: 23 May 2014
Cited by 4 | PDF Full-text (418 KB) | HTML Full-text | XML Full-text
Abstract
The predicted toxicity of mixtures of imidazolium and pyridinium ionic liquids (ILs) in the ratios of their EC50, EC10, and NOEC (no observed effect concentration) were compared to the observed toxicity of these mixtures on luciferase. The toxicities of
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The predicted toxicity of mixtures of imidazolium and pyridinium ionic liquids (ILs) in the ratios of their EC50, EC10, and NOEC (no observed effect concentration) were compared to the observed toxicity of these mixtures on luciferase. The toxicities of EC50 ratio mixture can be effectively predicted by two-stage prediction (TSP) method, but were overestimated by the concentration addition (CA) model and underestimated by the independent action (IA) model. The toxicities of EC10 ratio mixtures can be basically predicted by TSP and CA, but were underestimated by IA. The toxicities of NOEC ratio mixtures can be predicted by TSP and CA in a certain concentration range, but were underestimated by IA. Our results support the use of TSP as a default approach for predicting the combined effect of different types of ILs at the molecular level. In addition, mixtures of ILs mixed at NOEC and EC10 could cause significant effects of 64.1% and 97.7%, respectively. Therefore, we should pay high attention to the combined effects in mixture risk assessment. Full article
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Open AccessArticle Calcium Influx Inhibition is Involved in the Hypotensive and Vasorelaxant Effects Induced by Yangambin
Molecules 2014, 19(5), 6863-6876; https://doi.org/10.3390/molecules19056863
Received: 27 February 2014 / Revised: 13 May 2014 / Accepted: 15 May 2014 / Published: 23 May 2014
Cited by 2 | PDF Full-text (475 KB) | HTML Full-text | XML Full-text
Abstract
The pharmacological effects on the cardiovascular system of yangambin, a lignan isolated from Ocotea duckei Vattimo (Lauraceae), were studied in rats using combined functional and biochemical approaches. In non-anaesthetized rats, yangambin (1, 5, 10, 20, 30 mg/kg, i.v.) induced hypotension (−3.5 ± 0.2;
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The pharmacological effects on the cardiovascular system of yangambin, a lignan isolated from Ocotea duckei Vattimo (Lauraceae), were studied in rats using combined functional and biochemical approaches. In non-anaesthetized rats, yangambin (1, 5, 10, 20, 30 mg/kg, i.v.) induced hypotension (−3.5 ± 0.2; −7.1 ± 0.8; −8.9 ± 1.3; −14 ± 2.3, −25.5% ± 2.6%, respectively) accompanied by tachycardia (5.9 ± 0.5; 5.9 ± 1.6; 8.8 ± 1.4; 11.6, 18.8% ± 3.4%, respectively). In isolated rat atria, yangambin (0.1 µM–1 mM) had very slight negative inotropic (Emax = 35.6% ± 6.4%) and chronotropic effects (Emax = 10.2% ± 2.9%). In endothelium-intact rat mesenteric artery, yangambin (0.1 µM–1 mM) induced concentration-dependent relaxation (pD2 = 4.5 ± 0.06) of contractions induced by phenylephrine and this effect was not affected by removal of the endothelium. Interestingly, like nifedipine, the relaxant effect induced by yangambin was more potent on the contractile response induced by KCl 80 mM (pD2 = 4.8 ± 0.05) when compared to that induced by phenylephrine. Furthermore, yangambin inhibited CaCl2-induced contractions in a concentration-dependent manner. This lignan also induced relaxation (pD2 = 4.0 ± 0.04) of isolated arteries pre-contracted with S(−)-Bay K 8644. In fura-2/AM-loaded myocytes of rat mesenteric arteries, yangambin inhibited the Ca2+ signal evoked by KCl 60 mM. In conclusion, these results suggest that the hypotensive effect of yangambin is probably due to a peripheral vasodilatation that involves, at least, the inhibition the Ca2+ influx through voltage-gated Ca2+ channels. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Associations of nm23H1, VEGF-C, and VEGF-3 Receptor in Human Prostate Cancer
Molecules 2014, 19(5), 6851-6862; https://doi.org/10.3390/molecules19056851
Received: 6 May 2014 / Revised: 13 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
Cited by 8 | PDF Full-text (1722 KB) | HTML Full-text | XML Full-text
Abstract
We studied the expression of the non-metastatic clone 23 type 1 (nm23H1) gene, vascular endothelial growth factor (VEGF)-C, and its receptor VEGFR-3 using an in situ hybridization technique and immunohistochemical analyses with prostate cancer tissues and adjacent benign tissues of 52 human archival
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We studied the expression of the non-metastatic clone 23 type 1 (nm23H1) gene, vascular endothelial growth factor (VEGF)-C, and its receptor VEGFR-3 using an in situ hybridization technique and immunohistochemical analyses with prostate cancer tissues and adjacent benign tissues of 52 human archival cases. The association between VEGF-C expression, microlymphatic count (MLC), and staining intensity for nm23H1 and VEGFR-3 was used to evaluate tumor metastasis and survival rate. MLC values were significantly higher in tumorous tissue than in non-cancerous tissue. VEGF-C mRNA, VEGFR-3, and nm23H1 were highly expressed in tumorous tissue. VEGFR-3 expression was greater in VEGF-C mRNA-positive tumors than in VEGF-C mRNA-negative tumors. The association of VEGFR-3 expression with VEGF-C mRNA and MLC suggested that the poor prognosis and tumor metastasis associated with VEGFR-3 expression may be due, in part, to its role in promoting angiogenesis. VEGF-C expression was significantly associated with tumor lymphangiogenesis, angiogenesis, and immune response as a potent multifunctional stimulating factor in prostate cancer. Expression of nm23H1 was significantly inversely correlated with lymph node metastasis. Furthermore, there was a strong negative correlation between the expression of nm23H1, VEGF-C mRNA, and MLC. These findings provide important information for prophylactic, diagnostic, and therapeutic strategies for prostate cancer. Full article
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Open AccessCommunication A New Diterpene from Litsea cubeba Fruits: Structure Elucidation and Capability to Induce Apoptosis in HeLa Cells
Molecules 2014, 19(5), 6838-6850; https://doi.org/10.3390/molecules19056838
Received: 14 April 2014 / Revised: 16 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
Cited by 4 | PDF Full-text (1196 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A new diterpene, identified as (+)-6-(4-hydroxy-4-methyl-2-pentenoyl)-4,6-dimethyl-5-(3-methyl-2-butenyl)-1,3-cyclohexadienecarbaldehyde (1, cubelin), was isolated from a methanol extract of Litsea cubeba fruits by normal phase column chromatography and purified by preparative HPLC. The structure elucidation was conducted by spectroscopic methods (UV, IR, ESI-TOF-MS, 1-D and
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A new diterpene, identified as (+)-6-(4-hydroxy-4-methyl-2-pentenoyl)-4,6-dimethyl-5-(3-methyl-2-butenyl)-1,3-cyclohexadienecarbaldehyde (1, cubelin), was isolated from a methanol extract of Litsea cubeba fruits by normal phase column chromatography and purified by preparative HPLC. The structure elucidation was conducted by spectroscopic methods (UV, IR, ESI-TOF-MS, 1-D and 2-D NMR). Cubelin exhibited activity against HeLa cell viability and proliferation. The cells also exhibited changes in nuclear morphology which are hallmarks of apoptotic cell death. The presence of cleaved caspase-3/-7, caspase-8 and caspase-9 in the cubelin treated population indicated the potential of the compound to induce apoptosis in HeLa cells via both intrinsic and extrinsic pathways. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Synthesis and Antibacterial Activity of Amino Acid and Dipeptide Prodrugs of IMB-070593, a Fluoroquinolone Candidate
Molecules 2014, 19(5), 6822-6837; https://doi.org/10.3390/molecules19056822
Received: 14 April 2014 / Revised: 20 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
Cited by 4 | PDF Full-text (286 KB) | HTML Full-text | XML Full-text
Abstract
A series of amino acid and dipeptide prodrugs of IMB-070593, a fluoroquinolone candidate discovered in our lab, were synthesized and evaluated for their water solubility and then antibacterial activity. Our results reveal that four amino acid prodrugs 4a,b,e,
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A series of amino acid and dipeptide prodrugs of IMB-070593, a fluoroquinolone candidate discovered in our lab, were synthesized and evaluated for their water solubility and then antibacterial activity. Our results reveal that four amino acid prodrugs 4a,b,e,f and two dipeptide prodrugs 4k,l have much greater solubility (>85 mg/mL) than IMB-070593 mesylate (22.5 mg/mL). Compounds 4a and 4k show good in vivo efficacy against MSSA 12-1 (p.o./i.v., 5.32–7.68 mg/kg) and S. pneumoniae12-10 (p.o., 18.39–23.13 mg/kg) which is 1.19–1.50 fold more active than the parent drug. Full article
(This article belongs to the Section Medicinal Chemistry)
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Open AccessArticle Avicequinone C Isolated from Avicennia marina Exhibits 5α-Reductase-Type 1 Inhibitory Activity Using an Androgenic Alopecia Relevant Cell-Based Assay System
Molecules 2014, 19(5), 6809-6821; https://doi.org/10.3390/molecules19056809
Received: 8 April 2014 / Revised: 18 May 2014 / Accepted: 19 May 2014 / Published: 23 May 2014
Cited by 6 | PDF Full-text (697 KB) | HTML Full-text | XML Full-text
Abstract
Avicennia marina (AM) exhibits various biological activities and has been traditionally used in Egypt to cure skin diseases. In this study, the methanolic heartwood extract of AM was evaluated for inhibitory activity against 5α-reductase (5α-R) [E.C.1.3.99.5], the enzyme responsible for the over-production of
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Avicennia marina (AM) exhibits various biological activities and has been traditionally used in Egypt to cure skin diseases. In this study, the methanolic heartwood extract of AM was evaluated for inhibitory activity against 5α-reductase (5α-R) [E.C.1.3.99.5], the enzyme responsible for the over-production of 5α-dihydrotestosterone (5α-DHT) causing androgenic alopecia (AGA). An AGA-relevant cell-based assay was developed using human hair dermal papilla cells (HHDPCs), the main regulator of hair growth and the only cells within the hair follicle that are the direct site of 5α-DHT action, combined with a non-radioactive thin layer chromatography (TLC) detection technique. The results revealed that AM is a potent 5α-R type 1 (5α-R1) inhibitor, reducing the 5α-DHT production by 52% at the final concentration of 10 µg/mL. Activity-guided fractionation has led to the identification of avicequinone C, a furanonaphthaquinone, as a 5α-R1 inhibitor with an IC50 of 9.94 ± 0.33 µg/mL or 38.8 ± 1.29 µM. This paper is the first to report anti-androgenic activity through 5α-R1 inhibition of AM and avicequinone C. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessReview Applications of Liquid-Phase Microextraction in the Sample Preparation of Environmental Solid Samples
Molecules 2014, 19(5), 6776-6808; https://doi.org/10.3390/molecules19056776
Received: 21 April 2014 / Revised: 19 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
Cited by 7 | PDF Full-text (315 KB) | HTML Full-text | XML Full-text
Abstract
Solvent extraction remains one of the fundamental sample preparation techniques in the analysis of environmental solid samples, but organic solvents are toxic and environmentally harmful, therefore one of the possible greening directions is its miniaturization. The present review covers the relevant research from
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Solvent extraction remains one of the fundamental sample preparation techniques in the analysis of environmental solid samples, but organic solvents are toxic and environmentally harmful, therefore one of the possible greening directions is its miniaturization. The present review covers the relevant research from the field of application of microextraction to the sample preparation of environmental solid samples (soil, sediments, sewage sludge, dust etc.) published in the last decade. Several innovative liquid-phase microextraction (LPME) techniques that have emerged recently have also been applied as an aid in sample preparation of these samples: single-drop microextraction (SDME), hollow fiber-liquid phase microextraction (HF-LPME), dispersive liquid-liquid microextraction (DLLME). Besides the common organic solvents, surfactants and ionic liquids are also used. However, these techniques have to be combined with another technique to release the analytes from the solid sample into an aqueous solution. In the present review, the published methods were categorized into three groups: LPME in combination with a conventional solvent extraction; LPME in combination with an environmentally friendly extraction; LPME without previous extraction. The applicability of these approaches to the sample preparation for the determination of pollutants in solid environmental samples is discussed, with emphasis on their strengths, weak points and environmental impact. Full article
(This article belongs to the Special Issue Microextraction)
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Open AccessArticle A Facile Route to Tailoring Peptide-Stabilized Gold Nanoparticles Using Glutathione as a Synthon
Molecules 2014, 19(5), 6754-6775; https://doi.org/10.3390/molecules19056754
Received: 3 March 2014 / Revised: 20 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
Cited by 12 | PDF Full-text (1095 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The preparation of gold nanoparticles (AuNPs) of high purity and stability remains a major challenge for biological applications. This paper reports a simple synthetic strategy to prepare water-soluble peptide-stabilized AuNPs. Reduced glutathione, a natural tripeptide, was used as a synthon for the growth
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The preparation of gold nanoparticles (AuNPs) of high purity and stability remains a major challenge for biological applications. This paper reports a simple synthetic strategy to prepare water-soluble peptide-stabilized AuNPs. Reduced glutathione, a natural tripeptide, was used as a synthon for the growth of two peptide chains directly on the AuNP surface. Both nonpolar (tryptophan and methionine) and polar basic (histidine and dansylated arginine) amino acids were conjugated to the GSH-capped AuNPs. Ultracentrifugation concentrators with polyethersulfone (PES) membranes were used to purify precursor materials in each stage of the multi-step synthesis to minimize side reactions. Thin layer chromatography, transmission electron microscopy, UV-Visible, 1H-NMR, and fluorescence spectroscopies demonstrated that ultracentrifugation produces high purity AuNPs, with narrow polydispersity, and minimal aggregation. More importantly, it allows for more control over the composition of the final ligand structure. Studies under conditions of varying pH and ionic strength revealed that peptide length, charge, and hydrophobicity influence the stability as well as solubility of the peptide-capped AuNPs. The synthetic and purification strategies used provide a facile route for developing a library of tailored biocompatible peptide-stabilized AuNPs for biomedical applications. Full article
(This article belongs to the Special Issue Bioconjugations)
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Open AccessArticle Synthesis of Silver Nanoparticles by Green Method Stabilized to Synthetic Human Stomach Fluid
Molecules 2014, 19(5), 6737-6753; https://doi.org/10.3390/molecules19056737
Received: 22 April 2014 / Revised: 20 May 2014 / Accepted: 21 May 2014 / Published: 23 May 2014
Cited by 14 | PDF Full-text (1259 KB) | HTML Full-text | XML Full-text
Abstract
Silver nanoparticles (Ag NP) have been attracted much attention in recent years in biomedical applications due to their antimicrobial activity, but their drawbacks include toxicity and instability to aqueous hydrochloric acid solutions. Ag NPs have now been successfully prepared by a simple and
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Silver nanoparticles (Ag NP) have been attracted much attention in recent years in biomedical applications due to their antimicrobial activity, but their drawbacks include toxicity and instability to aqueous hydrochloric acid solutions. Ag NPs have now been successfully prepared by a simple and “green” synthesis method by reducing Ag+ ions in the presence of modified poly(vinyl alcohol) thiol (PVA-SH) in aqueous acidic solution. In this respect, Ag NPs were stabilized by coating different types of citrate-reduced Ag NPs with different weight ratios (1–3 Wt. %) of PVSH derivatives. The as-prepared Ag NPs were characterized using UV-Visible, high resolution transmission electron microscopy/ energy dispersive X-ray spectroscopy (TEM/EDS), dynamic light scattering (DLS) and X-ray powder diffraction (XRD) combined with Rietveld analysis. The changes in size, shape, and hydrodynamic diameter of Ag NPs after different duration exposure to synthetic stomach fluid (SSF) and1 M HCl were determined using TEM, XRD and UV-Visible analyses. The data indicated that these Ag NPs possessed high stability to SSF for more than 90 days, which was not previously reported in the literature. Full article
(This article belongs to the collection Bioactive Compounds)
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Open AccessArticle Four New Flavonol Glycosides from the Leaves of Brugmansia suaveolens
Molecules 2014, 19(5), 6727-6736; https://doi.org/10.3390/molecules19056727
Received: 31 March 2014 / Revised: 16 May 2014 / Accepted: 19 May 2014 / Published: 22 May 2014
PDF Full-text (242 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Four new flavonol glycosides were isolated from the leaves of Brugmansia suaveolens: kaempferol 3-O-β-D-glucopyranosyl-(1'''→2'')-O-α-L-arabinopyranoside (1), kaempferol 3-O-β-D-glucopyranosyl-(1'''→2'')-O-α-L-arabinopyranoside-7-O-į-D-gluco-pyranoside (2), kaempferol 3-O-β-D-[6'''-O-(E-caffeoyl)]-glucopyranosyl-(1'''→2'')-O-α-l-arabinopyranoside-7-O-β-D-glucopyranoside (3), and kaempferol 3-O-β-D-[2'''-O-(E-caffeoyl)]-glucopyranosyl-(1'''→2'')-O-α-l-arabinopyranoside-7-O-β-D-glucopyranoside (4). The structure elucidation was performed by MS, 1D and 2D NMR analyses. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessReview Role of Oligomeric Proanthocyanidins Derived from an Extract of Persimmon Fruits in the Oxidative Stress-Related Aging Process
Molecules 2014, 19(5), 6707-6726; https://doi.org/10.3390/molecules19056707
Received: 5 April 2014 / Revised: 19 May 2014 / Accepted: 19 May 2014 / Published: 22 May 2014
Cited by 3 | PDF Full-text (1513 KB) | HTML Full-text | XML Full-text
Abstract
Many researchers have focused on the oligomeric form of proanthocyanidins with a lower level of polymerization found in foodstuffs such as grape seeds and blackberries. The present study indicated that the oral administration of oligomers isolated from persimmon fruits extended the lifespan of
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Many researchers have focused on the oligomeric form of proanthocyanidins with a lower level of polymerization found in foodstuffs such as grape seeds and blackberries. The present study indicated that the oral administration of oligomers isolated from persimmon fruits extended the lifespan of senescence-accelerated mouse prone/8 (SAMP8), a murine model of accelerated senescence. On the other hand, oligomer-treated SAMP8 did not show stereotypical behavior. We also revealed that the oral administration of oligomers improved spatial and object recognition memory in SAMP8. The density of axons in the hippocampal CA1 was significantly increased by oligomer administration. Moreover, the administration of oligomers increased the phosphorylation of vascular endothelial growth factor receptor (VEGFR)-2 in the hippocampal CA3, hypothalamus, and choroid plexus. We speculate that memory improvement accompanied by histological changes may be induced directly in the hippocampus and indirectly in the hypothalamus and choroid plexus through VEGFR-2 signaling. In the present study, we elucidated the protective effect of oligomers against memory impairment with aging. VEGFR-2 signaling may provide a new insight into ways to protect against memory deficit in the aging brain. Full article
(This article belongs to the Special Issue Natural Antioxidants and Ageing)
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Open AccessArticle Linalool Exhibits Cytotoxic Effects by Activating Antitumor Immunity
Molecules 2014, 19(5), 6694-6706; https://doi.org/10.3390/molecules19056694
Received: 18 February 2014 / Revised: 5 May 2014 / Accepted: 19 May 2014 / Published: 22 May 2014
Cited by 27 | PDF Full-text (664 KB) | HTML Full-text | XML Full-text
Abstract
According to recent studies, the Plantaginaceae, which are traditional Chinese herbal remedies, have potential for use in viral infection treatment and cancer therapy. Linalool and p-coumaric acid are two of the biologically active compounds that can be isolated from the Plantaginaceae.
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According to recent studies, the Plantaginaceae, which are traditional Chinese herbal remedies, have potential for use in viral infection treatment and cancer therapy. Linalool and p-coumaric acid are two of the biologically active compounds that can be isolated from the Plantaginaceae. This study mainly focused on investigating the bioactivity of linalool as well as the bioactivity of p-coumaric acid in terms of their cytotoxic effects on cancer cells. Whether the mechanisms of such effects are generated through apoptosis and immunoregulatory activity were also investigated. By using WST-1 analysis, it was shown that linalool and p-coumaric acid have good inhibitory effects against breast, colorectal and liver cancer cells. The IC50 values of linalool for those cancer cell types were 224 μM, 222 μM, and 290 μM, respectively, and the IC50 values of p-coumaric acid were 693 μM, 215 μM and 87 μM, respectively. Cell cycle analysis also confirmed that linalool and p-coumaric acid can lead to apoptosis. By using flow cytometry, it was determined that treatment with linalool rather than p-coumaric acid significantly increased the sub-G1 phase and that there were more cells concentrated in the G1 phase. Furthermore, by using cytokine array analysis, we found that linalool can stimulate IFN-γ, IL-13, IL-2, IL-21, IL-21R, IL-4, IL-6sR and TNF-α secretion. This demonstrated that in addition to the bidirectional regulation capabilities found in linalool, it also induces Th1 cellular immune response in T-47D cells. These results showed that linalool holds great potential for use in cancer therapy, and we believe that it could provide an alternative way to take action against tumors. Full article
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Open AccessArticle Direct 2,3-O-Isopropylidenation of α-D-Mannopyranosides and the Preparation of 3,6-Branched Mannose Trisaccharides
Molecules 2014, 19(5), 6683-6693; https://doi.org/10.3390/molecules19056683
Received: 31 March 2014 / Revised: 9 May 2014 / Accepted: 19 May 2014 / Published: 22 May 2014
Cited by 5 | PDF Full-text (279 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A highly efficient, regioselective method for the direct 2,3-O-isopropylidenation of α-D-mannopyranosides is reported. Treatment of various α-D-mannopyranosides with 0.12 equiv of the TsOH·H2O and 2-methoxypropene at 70 °C gave 2,3-O-isopropylidene-α-D-mannopyranosides directly in 80%~90% yields. Based on this
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A highly efficient, regioselective method for the direct 2,3-O-isopropylidenation of α-D-mannopyranosides is reported. Treatment of various α-D-mannopyranosides with 0.12 equiv of the TsOH·H2O and 2-methoxypropene at 70 °C gave 2,3-O-isopropylidene-α-D-mannopyranosides directly in 80%~90% yields. Based on this method, a 3,6-branched α-D-mannosyl trisaccharide was prepared in 50.4% total yield using p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside as the starting material. Full article
(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)
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Open AccessArticle Synthesis and Antiproliferative Effects of Amino-Modified Perillyl Alcohol Derivatives
Molecules 2014, 19(5), 6671-6682; https://doi.org/10.3390/molecules19056671
Received: 18 April 2014 / Revised: 6 May 2014 / Accepted: 16 May 2014 / Published: 22 May 2014
Cited by 2 | PDF Full-text (2178 KB) | HTML Full-text | XML Full-text
Abstract
Two series of amino-modified derivatives of (S)-perillyl alcohol were designed and synthesized using (S)-perillaldehyde as the starting material. These derivatives showed increased antiproliferative activity in human lung cancer A549 cells, human melanoma A375-S2 cells and human fibrosarcoma HT-1080 cells
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Two series of amino-modified derivatives of (S)-perillyl alcohol were designed and synthesized using (S)-perillaldehyde as the starting material. These derivatives showed increased antiproliferative activity in human lung cancer A549 cells, human melanoma A375-S2 cells and human fibrosarcoma HT-1080 cells comparing with that of (S)-perillyl alcohol. Among these derivatives, compounds VI5 and VI7 were the most potent agents, with the IC50s below 100 μM. It was demonstrated that the antiproliferative effect of VI5 was mediated through the induction of apoptosis in A549 cells. Full article
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