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Molecules, Volume 12, Issue 4 (April 2007), Pages 703-931

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Research

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Open AccessArticle Investigation on the Binding of Polycyclic AromaticHydrocarbons with Soil Organic Matter: A Theoretical Approach
Molecules 2007, 12(4), 703-715; doi:10.3390/12040703
Received: 26 February 2007 / Revised: 22 March 2007 / Accepted: 23 March 2007 / Published: 5 April 2007
Cited by 7 | PDF Full-text (477 KB) | HTML Full-text | XML Full-text
Abstract
Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous contaminants of the terrestrial environment that have been designated as Environmental Protection Agency (EPA) Priority Pollutants. In this study, molecular modeling was used to examine the physical and chemical characteristics of soil organic matter (SOM), fulvic [...] Read more.
Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous contaminants of the terrestrial environment that have been designated as Environmental Protection Agency (EPA) Priority Pollutants. In this study, molecular modeling was used to examine the physical and chemical characteristics of soil organic matter (SOM), fulvic acid (FA) and humic acid (HA), as well as their binding interactions with PAHs. The molecular structures of 18 PAHs were built by using the SYBYL 7.0 program and then fully optimized by a semiempirical (AM1) method. A molecular docking program, AutoDock 3.05, was used to calculate the binding interactions between the PAHs, and three molecular structure models including FA (Buffle’s model), HA (Stevenson’s model) and SOM (Schulten and Schnitzer’s model). The π-π interactions and H-bonding interactions were found to play an important role in the intermolecular bonding of the SOM/PAHs complexes. In addition, significant correlations between two chemical properties, boiling point (bp) and octanol/water partition coefficient (Log Kow) and final docking energies were observed. The preliminary docking results provided knowledge of the important binding modes to FA, HA and SOM, and thereby to predict the sorption behavior of PAHs and other pollutants. Full article
(This article belongs to the Special Issue Heterocycles)
Open AccessArticle Synthesis and X-ray Structure of the Inclusion Complex of Dodecamethylcucurbit[6]uril with 1,4-Dihydroxybenzene
Molecules 2007, 12(4), 716-722; doi:10.3390/12040716
Received: 25 February 2007 / Revised: 19 March 2007 / Accepted: 19 March 2007 / Published: 5 April 2007
Cited by 15 | PDF Full-text (146 KB) | HTML Full-text | XML Full-text
Abstract
The synthesis, and X-ray crystal structure of the inclusion host-guest complex of dodecamethylcucurbit[6]uril (DDMeQ[6]) with 1,4-dihydroxybenzene (DHOBEN) are reported. The complex crystallizes in the space group P21/c (No.14) with a =12.2847(4), b = 12.6895(4), c = 15.1310(4) Å, α = 74.6960(10), β [...] Read more.
The synthesis, and X-ray crystal structure of the inclusion host-guest complex of dodecamethylcucurbit[6]uril (DDMeQ[6]) with 1,4-dihydroxybenzene (DHOBEN) are reported. The complex crystallizes in the space group P21/c (No.14) with a =12.2847(4), b = 12.6895(4), c = 15.1310(4) Å, α = 74.6960(10), β = 71.4090(10), γ = 86.5090(10)° and Z = 1. A novel approach to dodecamethylcucurbit[6]uril synthesis is also described. To separate dodecamethylcucurbit[6]uril, 1,4-dihydroxybenzene is used as a guest molecule for crystallization of the fully methyl-substituted cucurbituril. The driving force for the self-assembled inclusion host-guest complex can be attributed to not only the cavity interaction of dodecamethylcucurbit[6]uril (host), but also to the hydrogen bonding between the carbonyl oxygen at the portals of the host and the hydroxy groups of the guest. Full article
Open AccessArticle Multi-step Redox Systems with NIR-Fluorescence Based on 4H-Imidazoles
Molecules 2007, 12(4), 723-734; doi:10.3390/12040723
Received: 22 March 2007 / Revised: 29 March 2007 / Accepted: 29 March 2007 / Published: 5 April 2007
Cited by 9 | PDF Full-text (129 KB) | HTML Full-text | XML Full-text
Abstract
A new class of 4H-imidazoles was synthesized starting from fused-ring aromatic dinitriles. Strong bathochromic shifts of the longest wavelength absorptions were observed in the corresponding UV/vis spectra due to a conversion of the merocyanine chromophores into cyanines/(aza)oxonoles upon protonation/deprotonation of [...] Read more.
A new class of 4H-imidazoles was synthesized starting from fused-ring aromatic dinitriles. Strong bathochromic shifts of the longest wavelength absorptions were observed in the corresponding UV/vis spectra due to a conversion of the merocyanine chromophores into cyanines/(aza)oxonoles upon protonation/deprotonation of the 4H-imidazoles. Novel boratetraazapentalenes were synthesized via a cyclization reaction with boron trifluoride. These mesoionic species bearing a cyanine chromophore not only show NIR-fluorescence, they also participate as part of a quasi-reversible multi-step redox system. Large calculated semiquinone formation constants KSEM (3x1010 to 5x1011) indicate a high thermodynamic stability of the corresponding radical anions (SEM). Full article
Open AccessArticle Synthesis of (R)-Dihydropyridones as Key Intermediates for an Efficient Access to Piperidine Alkaloids
Molecules 2007, 12(4), 735-744; doi:10.3390/12040735
Received: 13 January 2007 / Revised: 25 January 2007 / Accepted: 27 January 2007 / Published: 10 April 2007
Cited by 14 | PDF Full-text (98 KB) | HTML Full-text | XML Full-text
Abstract
The efficient transformation of D-glucal to (2R)-hydroxymethyldihydro-pyridinone 5 in seven steps and 35 % overall yield is reported. Dihydropyridone 5 constitutes a versatile chiral building block for the synthesis of various piperidine alkaloids. In this regard, 5 was converted [...] Read more.
The efficient transformation of D-glucal to (2R)-hydroxymethyldihydro-pyridinone 5 in seven steps and 35 % overall yield is reported. Dihydropyridone 5 constitutes a versatile chiral building block for the synthesis of various piperidine alkaloids. In this regard, 5 was converted to piperidinol 13 and piperidinone 15, that may be further elaborated for the syntheses of (+)-desoxoprosophylline (1) and deoxymannojirimycin (3) or D-mannolactam (4), respectively. Full article
Open AccessArticle Evaluation of the Antioxidant Properties of Litchi Fruit Phenolics in Relation to Pericarp Browning Prevention
Molecules 2007, 12(4), 759-771; doi:10.3390/12040759
Received: 14 March 2007 / Revised: 25 March 2007 / Accepted: 30 March 2007 / Published: 11 April 2007
Cited by 92 | PDF Full-text (97 KB)
Abstract
Phenolics were extracted from litchi fruit pericarp (LFP) tissues, purified and their antioxidant properties analyzed. LFP phenolics strongly inhibited linoleic acid oxidation and exhibited a dose-dependent free-radical scavenging activity against α,α-diphenyl-β-picrylhydrazyl (DPPH·) and hydroxyl radicals and superoxide anions. The degradation of deoxyribose [...] Read more.
Phenolics were extracted from litchi fruit pericarp (LFP) tissues, purified and their antioxidant properties analyzed. LFP phenolics strongly inhibited linoleic acid oxidation and exhibited a dose-dependent free-radical scavenging activity against α,α-diphenyl-β-picrylhydrazyl (DPPH·) and hydroxyl radicals and superoxide anions. The degradation of deoxyribose by hydroxyl radicals was inhibited by phenolics acting mainly as iron ion chelators, rather than by directly scavenging the radicals. Phenolics from litchi fruit pericarp were found to display similar reducing power activity as ascorbic acid. The effect of phenolic compound treatment on pericarp browning and electrolyte leakage of litchi fruit was also evaluated and it was observed that application of exogenous litchi phenolics to harvested litchi fruit significantly prevented pericarp browning and delayed increases in electrolyte leakage. These results suggest that litchi pericarp tissue phenolics could be beneficial in scavenging free radicals, maintaining membrane integrity and, thereby inhibiting pericarp browning of litchi fruit. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Chemical Composition and Antimicrobial Activity of the Essential Oil of Algerian Phlomis bovei De Noé subsp. bovei
Molecules 2007, 12(4), 772-781; doi:10.3390/12040772
Received: 27 February 2007 / Revised: 27 March 2007 / Accepted: 3 April 2007 / Published: 12 April 2007
Cited by 14 | PDF Full-text (106 KB) | HTML Full-text | XML Full-text
Abstract
The chemical composition of essential oil obtained by steam distillation of dried aerial parts of Phlomis bovei De Noé subsp. bovei collected from Algeria, was analyzed by GC and GC/MS. Seventy five constituents (corresponding to 86.37% of the total weight) were identified. [...] Read more.
The chemical composition of essential oil obtained by steam distillation of dried aerial parts of Phlomis bovei De Noé subsp. bovei collected from Algeria, was analyzed by GC and GC/MS. Seventy five constituents (corresponding to 86.37% of the total weight) were identified. The main components were: germacrene D, β-caryophyllene, β-bournonene, thymol and hexahydrofarnesyl acetone. Furthermore, the antimicrobial activity of the oil was evaluated against six Gram (+/-) bacteria and three pathogenic fungi, using the agar dilution technique. It was found that the oil exhibited strong antimicrobial activity against most of the tested microorganisms. Full article
Open AccessArticle Complexes of 3dn Metal Ions with Thiosemicarbazones: Synthesis and Antimicrobial Activity
Molecules 2007, 12(4), 782-796; doi:10.3390/12040782
Received: 27 February 2007 / Revised: 5 April 2007 / Accepted: 12 April 2007 / Published: 17 April 2007
Cited by 34 | PDF Full-text (204 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The chelating behavior of the thiosemicarbazone derivatives of 2-hydroxy-8-R-tricyclo[7.3.1.0.2,7]tridecane-13-one (where R = H, CH3, C6H5) towards Co(II), Ni(II) and Cu(II) has been investigated by elemental analysis, molar conductivity measurements, UV-VIS, IR, ESR spectroscopy and [...] Read more.
The chelating behavior of the thiosemicarbazone derivatives of 2-hydroxy-8-R-tricyclo[7.3.1.0.2,7]tridecane-13-one (where R = H, CH3, C6H5) towards Co(II), Ni(II) and Cu(II) has been investigated by elemental analysis, molar conductivity measurements, UV-VIS, IR, ESR spectroscopy and thermal studies. It was deduced from the experiments performed that the ligands coordinate to metal ions in different ways – neutral bidentate or mononegative bidentate – depending on the nature of R. Also, if metal acetates are used instead of metal chlorides, the ligands coordinate in a mononegative bidentate fashion, regardless of the nature of R or the thiosemicarbazone type ligand. The antimicrobial activity of the ligands and of the complexes towards samples of Acinetobacter boumanii, Klebsiella pneumoniae, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa was determined. Full article
Open AccessArticle Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism
Molecules 2007, 12(4), 797-804; doi:10.3390/12040797
Received: 13 February 2007 / Revised: 14 April 2007 / Accepted: 16 April 2007 / Published: 18 April 2007
Cited by 2 | PDF Full-text (66 KB) | HTML Full-text | XML Full-text
Abstract
An electron-transfer chain reaction between 2-nitropropane anion and α-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-yl)ethanone or 2-bromo-1-(4-nitrophenyl)ethanone were reacted with several cyclic nitronate anions to form α,β-unsaturated ketones via a [...] Read more.
An electron-transfer chain reaction between 2-nitropropane anion and α-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-yl)ethanone or 2-bromo-1-(4-nitrophenyl)ethanone were reacted with several cyclic nitronate anions to form α,β-unsaturated ketones via a SRN1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues. Full article
Open AccessArticle Molecularly Imprinted Polymers for 5-Fluorouracil Release in Biological Fluids
Molecules 2007, 12(4), 805-814; doi:10.3390/12040805
Received: 21 March 2007 / Revised: 13 March 2007 / Accepted: 16 April 2007 / Published: 18 April 2007
Cited by 41 | PDF Full-text (69 KB) | HTML Full-text | XML Full-text
Abstract
The aim of this work was to investigate the possibility of employing Molecularly Imprinted Polymers (MIPs) as a controlled release device for 5-fluorouracil (5-FU) in biological fluids, especially gastrointestinal ones, compared to Non Imprinted Polymers (NIPs). MIPs were synthesized using methacrylic acid [...] Read more.
The aim of this work was to investigate the possibility of employing Molecularly Imprinted Polymers (MIPs) as a controlled release device for 5-fluorouracil (5-FU) in biological fluids, especially gastrointestinal ones, compared to Non Imprinted Polymers (NIPs). MIPs were synthesized using methacrylic acid (MAA) as functional monomer and ethylene glycol dimethacrylate (EGDMA) as crosslinking agent. The capacity of the polymer to recognize and to bind the template selectively in both organic and aqueous media was evaluated. An in vitro release study was performed both in gastrointestinal and in plasma simulating fluids. The imprinted polymers bound much more 5-Fu than the corresponding non-imprinted ones and showed a controlled/sustained drug release, with MIPs release rate being indeed much more sustained than that obtained from NIPs. These polymers represent a potential valid system for drug delivery and this study indicates that the selective binding characteristic of molecularly imprinted polymers is promising for the preparation of novel controlled release drug dosage form. Full article
Open AccessCommunication Bis(4-hydroxybenzyl)sulfide: a Sulfur Compound Inhibitor of Histone Deacetylase Isolated from Root Extract of Pleuropterus ciliinervis
Molecules 2007, 12(4), 815-820; doi:10.3390/12040815
Received: 5 April 2007 / Revised: 16 April 2007 / Accepted: 16 April 2007 / Published: 20 April 2007
Cited by 8 | PDF Full-text (44 KB) | HTML Full-text | XML Full-text
Abstract
A sulfur compound, bis(4-hydroxybenzyl)sulfide (1) was isolated from the root extract of Pleuropterus ciliinervis. Its structure was elucidated using NMR spectroscopic techniques and mass spectrometric analysis. Compound 1 showed potent inhibitory activity in a histone deacetylase (HDAC) enzyme assay. It also [...] Read more.
A sulfur compound, bis(4-hydroxybenzyl)sulfide (1) was isolated from the root extract of Pleuropterus ciliinervis. Its structure was elucidated using NMR spectroscopic techniques and mass spectrometric analysis. Compound 1 showed potent inhibitory activity in a histone deacetylase (HDAC) enzyme assay. It also exhibited growth inhibitory activity on five human tumor cell lines and more sensitive inhibitory activity on the MDA-MB-231 breast tumor cell line. Full article
Open AccessArticle Different Supramolecular Coordination Polymers of [N,N'-di(pyrazin-2-yl)-pyridine-2,6-diamine]Ni(II) with Anions and Solvent Molecules as a Result of Hydrogen Bonding
Molecules 2007, 12(4), 821-831; doi:10.3390/12040821
Received: 15 March 2007 / Revised: 18 April 2007 / Accepted: 19 April 2007 / Published: 23 April 2007
Cited by 3 | PDF Full-text (382 KB)
Abstract
Ni(II) complexes of N,N'–di(pyrazin–2–yl)pyridine–2,6–diamine (H2dpzpda) with different anions were synthesized and their structures were determined by X-ray diffraction. Hydrogen bonds between the amino groups and anions assembled the mononuclear molecules into different architectures. The perchlorate complex had a 1-D [...] Read more.
Ni(II) complexes of N,N'–di(pyrazin–2–yl)pyridine–2,6–diamine (H2dpzpda) with different anions were synthesized and their structures were determined by X-ray diffraction. Hydrogen bonds between the amino groups and anions assembled the mononuclear molecules into different architectures. The perchlorate complex had a 1-D chain structure, whereas switching the anion from perchlorate to nitrate resulted in a corresponding change of the supramolecular structure from 1-D to 3-D. When the nitrate complex packed with the co-crystallized water, a double chain structure was formed through hydrogen bonding. The magnetic studies revealed values of g = 2.14 and D = 3.11 cm-1 for [Ni(H2dpzpda)2](ClO4)2 (1) and g = 2.18 and D = 2.19 cm-1 for [Ni(H2dpzpda)2](NO3)2 (2), respectively. Full article
Open AccessArticle Cytotoxic Triterpenoid Saponins from the Roots of Platycodon grandiflorum
Molecules 2007, 12(4), 832-841; doi:10.3390/12040832
Received: 30 January 2007 / Revised: 2 April 2007 / Accepted: 3 April 2007 / Published: 23 April 2007
Cited by 13 | PDF Full-text (103 KB) | HTML Full-text | XML Full-text
Abstract
Bioguided fractionation of the ethanol extracts obtained from Platycodon grandiflorum roots led to isolation of two new triterpenoid saponins, characterized as 3-O-β-D-glucopyranosyl-2β,12α,16α,23,24-pentahydroxyoleanane-28(13)-lactone (1) and 3-O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-2β,12α,16α,23α-tetrahydroxyoleanane-28(13)- lactone (2) by 1D- and 2D-NMR and MS techniques, as well as chemical means. Both compounds showed [...] Read more.
Bioguided fractionation of the ethanol extracts obtained from Platycodon grandiflorum roots led to isolation of two new triterpenoid saponins, characterized as 3-O-β-D-glucopyranosyl-2β,12α,16α,23,24-pentahydroxyoleanane-28(13)-lactone (1) and 3-O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-2β,12α,16α,23α-tetrahydroxyoleanane-28(13)- lactone (2) by 1D- and 2D-NMR and MS techniques, as well as chemical means. Both compounds showed cytotoxic activity against human ECA-109 cells. Full article
Open AccessArticle Identificationof Major Phenolic Compounds of Chinese Water Chestnut and their Antioxidant Activity
Molecules 2007, 12(4), 842-852; doi:10.3390/12040842
Received: 7 April 2007 / Revised: 20 April 2007 / Accepted: 23 April 2007 / Published: 25 April 2007
Cited by 20 | PDF Full-text (137 KB) | HTML Full-text | XML Full-text
Abstract
Chinese water chestnut (CWC) is one of the most popular foods among Asian people due to its special taste and medical function. Experiments were conducted to test the antioxidant activity and then determine the major phenolic compound components present in CWC. CWC [...] Read more.
Chinese water chestnut (CWC) is one of the most popular foods among Asian people due to its special taste and medical function. Experiments were conducted to test the antioxidant activity and then determine the major phenolic compound components present in CWC. CWC phenolic extract strongly inhibited linoleic acid oxidation and exhibited a dose-dependent free-radical scavenging activity against α,α-diphenyl-β-picrylhydrazyl (DPPH) radicals, superoxide anions and hydroxyl radicals, which was superior to ascorbic acid and butylated hydroxytoluene (BHT), two commercial used antioxidants. Furthermore, the CWC extract was found to have a relatively higher reducing power, compared with BHT. The major phenolic compounds present in CWC tissues were extracted, purified and identified by high-performance liquid chromatograph (HPLC) as (–)-gallocatechin gallate, (–)-epicatechin gallate and (+)-catechin gallate. This study suggests that CWC tissues exhibit great potential for antioxidant activity and may be useful for their nutritional and medicinal functions. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Molecular Complexes Based on Tetrathiafulvalene and Dialkylviologens
Molecules 2007, 12(4), 853-860; doi:10.3390/12040853
Received: 7 April 2007 / Revised: 17 April 2007 / Accepted: 18 April 2007 / Published: 27 April 2007
Cited by 5 | PDF Full-text (232 KB) | HTML Full-text | XML Full-text
Abstract
Three kinds of molecular complexes based on tetrathiafulvalene (TTF) and dialkylviologens were prepared and their crystal structures elucidated. While TTF-dimethylviologen complex forms a mixed stack arrangement of donors and acceptors in its crystal structure, TTF donors aggregate with long alkyl groups by [...] Read more.
Three kinds of molecular complexes based on tetrathiafulvalene (TTF) and dialkylviologens were prepared and their crystal structures elucidated. While TTF-dimethylviologen complex forms a mixed stack arrangement of donors and acceptors in its crystal structure, TTF donors aggregate with long alkyl groups by CH/p and/or van der Waals interactions in a couple of TTF-heptylviologen complexes. Full article
Open AccessCommunication C(aryl)-O Bond Formation from Aryl Methanesulfonates via Consecutive Deprotection and SNAr Reactions with Aryl Halides in an Ionic Liquid
Molecules 2007, 12(4), 861-867; doi:10.3390/12040861
Received: 28 March 2007 / Revised: 19 April 2007 / Accepted: 20 April 2007 / Published: 30 April 2007
Cited by 4 | PDF Full-text (70 KB) | HTML Full-text | XML Full-text
Abstract An efficient K3PO4-mediated synthesis of unsymmetrical diaryl ethers using the ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) as solvent has been developed. The procedure involves consecutive deprotection of aryl methane-sulfonates and a nucleophilic aromatic substitution (SNAr) with activated aryl halides. Full article
Open AccessArticle Microwave-Assisted Isolation of Essential oil of Cinnamomum iners Reinw. ex Bl.: Comparison with Conventional Hydrodistillation
Molecules 2007, 12(4), 868-877; doi:10.3390/12040868
Received: 22 February 2007 / Revised: 27 April 2007 / Accepted: 27 April 2007 / Published: 30 April 2007
Cited by 30 | PDF Full-text (94 KB) | HTML Full-text | XML Full-text
Abstract
Microwave-assistedhydrodistillation was used to isolate an essential oil from the leaves of Cinnamomuminers Reinw. ex Bl., and the results compared with those obtained by conventional hydrodistillation. The composition of the oil from both methods was found to be similar, and (-)-linalool was [...] Read more.
Microwave-assistedhydrodistillation was used to isolate an essential oil from the leaves of Cinnamomuminers Reinw. ex Bl., and the results compared with those obtained by conventional hydrodistillation. The composition of the oil from both methods was found to be similar, and (-)-linalool was found as the main component (30-50 %). The antioxidant activity of the essential oil obtained by both methods was evaluated using DPPH, ABTS, FRAP and lipid peroxidation methods, all of which indicated the same but insignificant activity. Full article
Open AccessCommunication How Many Drugs Are Catecholics
Molecules 2007, 12(4), 878-884; doi:10.3390/12040878
Received: 27 March 2007 / Revised: 23 April 2007 / Accepted: 25 April 2007 / Published: 30 April 2007
Cited by 24 | PDF Full-text (58 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
By examination of the 8659 drugs recorded in the Comprehensive Medicinal Chemistry (CMC) database, 78 catecholics (including five pyrogallolics) were identified, of which 17 are currently prescribed by FDA. Through analyzing the substitutent patterns, ClogPs and O-H bond dissociation enthalpies(BDEs) [...] Read more.
By examination of the 8659 drugs recorded in the Comprehensive Medicinal Chemistry (CMC) database, 78 catecholics (including five pyrogallolics) were identified, of which 17 are currently prescribed by FDA. Through analyzing the substitutent patterns, ClogPs and O-H bond dissociation enthalpies(BDEs) of the catecholic drugs, some molecular features that may benefit circumventing the toxicity of catecholics were revealed: i) strong electron-donating substituents are excluded; ii) ClogP 3; iii) an energy penalty exists for quinone formation. Besides, the present analyses also suggest that the clinical usage and dosage of currently prescribed catecholic drugs are of importance in designing or screening catecholic antioxidants. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
Open AccessArticle Synthesis and Activity of a New Series of(Z)-3-Phenyl-2-benzoylpropenoic Acid Derivatives as Aldose Reductase Inhibitors
Molecules 2007, 12(4), 885-895; doi:10.3390/12040885
Received: 21 March 2007 / Revised: 23 April 2007 / Accepted: 23 April 2007 / Published: 30 April 2007
Cited by 8 | PDF Full-text (143 KB) | HTML Full-text | XML Full-text
Abstract
During the course of studies directed towards the discovery of novel aldose reductase inhibitors for the treatment of diabetic complications, we synthesized a series of new (Z)-3-phenyl-2-benzoylpropenoic acid derivatives and tested their in vitro inhibitory activities on rat lens aldose [...] Read more.
During the course of studies directed towards the discovery of novel aldose reductase inhibitors for the treatment of diabetic complications, we synthesized a series of new (Z)-3-phenyl-2-benzoylpropenoic acid derivatives and tested their in vitro inhibitory activities on rat lens aldose reductase. Of these compounds, (Z)-3-(3,4-dihydroxyphenyl)-2-(4-methylbenzoyl)propenoicacid(3k) was identified as the most potent inhibitor, with an IC50 of 0.49μM. The theoretical binding mode of 3k was obtained by simulation of its docking into the active site of the human aldose reductase crystal structure. Full article
Open AccessArticle 4'-Acetamidochalcone Derivatives as Potential Antinociceptive Agents
Molecules 2007, 12(4), 896-906; doi:10.3390/12040896
Received: 22 March 2007 / Revised: 22 April 2007 / Accepted: 24 April 2007 / Published: 30 April 2007
Cited by 13 | PDF Full-text (59 KB) | HTML Full-text | XML Full-text
Abstract
Nine acetamidochalcones were synthesized and evaluated as antinociceptive agents using the mice writhing test. Given intraperitoneally all the compounds were more effective than the two reference analgesic drugs (acetylsalicylic acid and acetaminophen) used for comparison. N-{4-[(2E)-3-(4-nitrophenyl)prop-2-enoyl]phenyl}acetamide (6) was the [...] Read more.
Nine acetamidochalcones were synthesized and evaluated as antinociceptive agents using the mice writhing test. Given intraperitoneally all the compounds were more effective than the two reference analgesic drugs (acetylsalicylic acid and acetaminophen) used for comparison. N-{4-[(2E)-3-(4-nitrophenyl)prop-2-enoyl]phenyl}acetamide (6) was the most effective compound and was therefore selected for more detailed studies. It caused dose-related inhibition in the writhing test, being about 32 to 34-fold more potent than the standard drugs. It was also effective in the second phase of the formalin test and the capsaicin test. These acetamidochalcones, especially compound 6, might be further used as models to obtain new and more potent analgesic drugs. Full article
Open AccessArticle Determination of the Three-dimensional Structure of Gynoside A in Solution using NMR and Molecular Modeling
Molecules 2007, 12(4), 907-916; doi:10.3390/12040907
Received: 23 March 2007 / Revised: 5 April 2007 / Accepted: 18 April 2007 / Published: 30 April 2007
Cited by 3 | PDF Full-text (254 KB) | HTML Full-text | XML Full-text
Abstract
The three-dimensional structure of Gynoside A, an ocotillone-type triterpenoid glycoside isolated from Gynostemma pentaphyllum, was determined in pyridine-d5 and DMSO-d6 solution through constrained molecular modeling using constraints derived from proton NMR spectra. The calculation yielded well-defined global [...] Read more.
The three-dimensional structure of Gynoside A, an ocotillone-type triterpenoid glycoside isolated from Gynostemma pentaphyllum, was determined in pyridine-d5 and DMSO-d6 solution through constrained molecular modeling using constraints derived from proton NMR spectra. The calculation yielded well-defined global minima. Except for some quantitative details the overall structure of Gynoside A in pyridine-d5 shared many common features with that in DMSO-d6. The structure in pyridine-d5 had lower energies than that in DMSO-d6 solution. Full article
Open AccessArticle Effects of Different Carriers on the Production of Isoflavone Powder from Soybean Cake
Molecules 2007, 12(4), 917-931; doi:10.3390/12040917
Received: 2 April 2007 / Revised: 24 April 2007 / Accepted: 25 April 2007 / Published: 30 April 2007
Cited by 7 | PDF Full-text (134 KB) | HTML Full-text | XML Full-text
Abstract
The objectives of this study were to use soybean cake as the raw material for the production of isoflavone powder and compare the effects of different carriers as well as drying methods on the powder quality. Results showed that with spray drying, [...] Read more.
The objectives of this study were to use soybean cake as the raw material for the production of isoflavone powder and compare the effects of different carriers as well as drying methods on the powder quality. Results showed that with spray drying, a level of 40 % maltodextrin as carrier produced the highest yield (mass) of isoflavone powder, followed by 10 % gelatin and 1 % sodium alginate. However, a reversed trend was observed for the isoflavone content. With 1 % sodium alginate, freeze drying generated the greatest yield of isoflavone powder, followed by vacuum drying and spray drying. The isoflavone content also exhibited the same tendency. With poly-g-glutamicacid (g-PGA) as carrier, all six levels studied (0.57, 0.28, 0.14, 0.028, 0.014 and 0.003 %) were capable of forming powder containing high amounts of total isoflavone, which was comparable to that using 1% sodiumalginate by freeze drying. Both high- and low-molecular-weight g-PGA showed similar effects in terms of powder yield and isoflavone content. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)

Review

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Open AccessReview Litchi Flavonoids: Isolation, Identification and Biological Activity
Molecules 2007, 12(4), 745-758; doi:10.3390/12040745
Received: 14 March 2007 / Revised: 26 March 2007 / Accepted: 28 March 2007 / Published: 11 April 2007
Cited by 36 | PDF Full-text (106 KB) | HTML Full-text | XML Full-text
Abstract
The current status of the isolation, identification, biological activity, utilization and development prospects of flavonoids found in litchi fruit pericarp (LFP) tissues is reviewed. LFP tissues account for approximately 15% by weight of the whole fresh fruit and are comprised of significant [...] Read more.
The current status of the isolation, identification, biological activity, utilization and development prospects of flavonoids found in litchi fruit pericarp (LFP) tissues is reviewed. LFP tissues account for approximately 15% by weight of the whole fresh fruit and are comprised of significant amount of flavonoids. The major flavonoids in ripe LFP include flavonols and anthocyanins. The major flavanols in the LFP are reported to be procyanidin B4, procyanidin B2 and epicatechin, while cyanindin-3-rutinside, cyanidin-3-glucoside, quercetin-3-rutinosde and quercetin-3-glucoside are identified as the important anthocyanins. Litchi flavanols and anthocyanins exhibit good potential antioxidant activity. The hydroxyl radical and superoxide anion scavenging activities of procyanidin B2 are greater than those of procyanidin B4 and epicatechin, while epicatechin has the highest α,α-diphenyl-β-picrylhydrazyl radical (DPPH·) scavenging activity. In addition to the antioxidant activity, LFP extract displays a dose- and time-dependent inhibitory effect on human breast cancer, which could be attributed, in part, to its inhibition of proliferation and induction of apoptosis in cancer cells through upregulation and down-regulation of multiple genes. Furthermore, various anticancer activities are observed for epicatechin, procyanidin B2, procyanidin B4 and the ethyl acetate fraction of LFP tissue extracts. Procyanidin B4 and the ethyl acetate fraction show a stronger inhibitory effect on HELF than MCF-7 proliferation, while epicatechin and procyanidin B2 have lower cytotoxicities towards MCF-7 and HELF than paclitaxel. It is therefore suggested that flavonoids from LFP might be potentially useful components for functional foods and/or anti-breast cancer drugs. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)

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