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Molecules, Volume 14, Issue 1 (January 2009) – 47 articles , Pages 1-585

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128 KiB  
Editorial
Molecules’ Highlights in 2008 and a Look Forward to 2009
by Shu-Kun Lin and Derek McPhee
Molecules 2009, 14(1), 584-585; https://doi.org/10.3390/molecules14010584 - 23 Jan 2009
Cited by 1 | Viewed by 10224
Abstract
As has now become a custom for Molecules, as one year ends and another starts its Publisher and Editor-in-Chief would like to take stock of our progress in 2008 and offer our readership a preview of things to come in 2009. Just as [...] Read more.
As has now become a custom for Molecules, as one year ends and another starts its Publisher and Editor-in-Chief would like to take stock of our progress in 2008 and offer our readership a preview of things to come in 2009. Just as we had hoped in last year’s editorial [1], the year that just concluded proved to be another outstanding one for MDPI's flagship journal Molecules. By year’s end we had published 239 papers and three Editorials or Editor's Notes for a total of 3,252 pages. While the 8% growth in the number of papers published compared to 2007 may appear modest, the number of pages published represented a 22% increase over the prior year, and was largely attributable to the increase in the number of reviews published. [...] Full article
215 KiB  
Article
Antiosteoporotic Activity of Anthraquinones from Morinda officinalis on Osteoblasts and Osteoclasts
by Yan-Bin Wu, Cheng-Jian Zheng, Lu-Ping Qin, Lian-Na Sun, Ting Han, Lei Jiao, Qiao-Yan Zhang and Jin-Zhong Wu
Molecules 2009, 14(1), 573-583; https://doi.org/10.3390/molecules14010573 - 23 Jan 2009
Cited by 119 | Viewed by 17776
Abstract
Bioactivity-guided fractionation led to the successful isolation of antiosteoporotic components, i.e. physicion (1), rubiadin-1-methyl ether (2), 2-hydroxy-1-methoxy- anthraquinone (3), 1,2-dihydroxy-3-methylanthraquinone (4), 1,3,8-trihydroxy-2-methoxy- anthraquinone (5), 2-hydroxymethyl-3-hydroxyanthraquinone (6), 2-methoxyanthraquinone (7) and scopoletin (8) from an ethanolic extract of the roots of Morinda officinalis. Compounds [...] Read more.
Bioactivity-guided fractionation led to the successful isolation of antiosteoporotic components, i.e. physicion (1), rubiadin-1-methyl ether (2), 2-hydroxy-1-methoxy- anthraquinone (3), 1,2-dihydroxy-3-methylanthraquinone (4), 1,3,8-trihydroxy-2-methoxy- anthraquinone (5), 2-hydroxymethyl-3-hydroxyanthraquinone (6), 2-methoxyanthraquinone (7) and scopoletin (8) from an ethanolic extract of the roots of Morinda officinalis. Compounds 4-8 are isolated for the first time from M. officinalis. Among them, compounds 2 and 3 promoted osteoblast proliferation, while compounds 4, 5 increased osteoblast ALP activity. All of the isolated compounds inhibited osteoclast TRAP activity and bone resorption, and the inhibitory effects on osteoclastic bone resorption of compounds 1 and 5 were stronger than that of other compounds. Taken together, antiosteoporotic activity of M. officinalis and its anthraquinones suggest therapeutic potential against osteoporosis. Full article
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196 KiB  
Communication
Rubiacordone A: A New Anthraquinone Glycoside from the Roots of Rubia cordifolia
by Xiang Li, Zhi Liu, Yun Chen, Li-Juan Wang, Yi-Nan Zheng, Guang-Zhi Sun and Chang-Chun Ruan
Molecules 2009, 14(1), 566-572; https://doi.org/10.3390/molecules14010566 - 23 Jan 2009
Cited by 30 | Viewed by 17374
Abstract
A new anthraquinone, Rubiacordone A (1) (6-acetoxy-1-hydroxy-2-methylanthraquinone-3-O-α-L-rhamnopyranoside), was isolated together with the known anthraquinone, 1-acetoxy-6-hydroxy-2-methylanthraquinone-3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside] (2), from the dried roots of Rubia cordifolia. Their structures were [...] Read more.
A new anthraquinone, Rubiacordone A (1) (6-acetoxy-1-hydroxy-2-methylanthraquinone-3-O-α-L-rhamnopyranoside), was isolated together with the known anthraquinone, 1-acetoxy-6-hydroxy-2-methylanthraquinone-3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside] (2), from the dried roots of Rubia cordifolia. Their structures were elucidated on the basis of extensive 1D and 2D-NMR, as well as HRESI-MS spectroscopic analysis. Metabolites 1 and 2 showed considerable antimicrobial activity against Gram-positive bacteria. Full article
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555 KiB  
Article
Optimization and Comparison of Five Methods for Extraction of Coniferyl Ferulate from Angelica sinensis
by Jing-Jing Xie, Jia Lu, Zheng-Ming Qian, Yue Yu, Jin-Ao Duan and Shao-Ping Li
Molecules 2009, 14(1), 555-565; https://doi.org/10.3390/molecules14010555 - 23 Jan 2009
Cited by 27 | Viewed by 19480
Abstract
Coniferyl ferulate, which is noted for its multiple pharmacological activities and chemical instability, is abundant in Angelica sinensis. In this paper, five methods, namely sonication extraction (SE), pressurized liquid extraction (PLE), supercritical fluid extraction (SFE), hydrodistillation (HD) and decoction (DC) for extraction [...] Read more.
Coniferyl ferulate, which is noted for its multiple pharmacological activities and chemical instability, is abundant in Angelica sinensis. In this paper, five methods, namely sonication extraction (SE), pressurized liquid extraction (PLE), supercritical fluid extraction (SFE), hydrodistillation (HD) and decoction (DC) for extraction of coniferyl ferulate, as well as ferulic acid, Z/E-ligustilide and Z/E-butylidenephthalide, from A. sinensis were optimized and compared. The results showed that the order of extraction efficiency was: PLE»SE>SFE>>HD, DC. The compositions of the SE, PLE and SFE extracts, which had a high ratio of coniferyl ferulate, were very similar, while no coniferyl ferulate was obtained by HD and DC, though they had high selectivity for the extraction of ligustilide and ferulic acid, respectively. It was noteworthy that the content of ligustilide and coniferyl ferulate was not detectable in the decoction, the commonly used oral administration form of Traditional Chinese Medicines in clinical practice. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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466 KiB  
Review
Biological and Pharmacological Activities of Squalene and Related Compounds: Potential Uses in Cosmetic Dermatology
by Zih-Rou Huang, Yin-Ku Lin and Jia-You Fang
Molecules 2009, 14(1), 540-554; https://doi.org/10.3390/molecules14010540 - 23 Jan 2009
Cited by 358 | Viewed by 53943
Abstract
Squalene is a triterpene that is an intermediate in the cholesterol biosynthesis pathway. It was so named because of its occurrence in shark liver oil, which contains large quantities and is considered its richest source. However, it is widely distributed in nature, with [...] Read more.
Squalene is a triterpene that is an intermediate in the cholesterol biosynthesis pathway. It was so named because of its occurrence in shark liver oil, which contains large quantities and is considered its richest source. However, it is widely distributed in nature, with reasonable amounts found in olive oil, palm oil, wheat-germ oil, amaranth oil, and rice bran oil. Squalene, the main component of skin surface polyunsaturated lipids, shows some advantages for the skin as an emollient and antioxidant, and for hydration and its antitumor activities. It is also used as a material in topically applied vehicles such as lipid emulsions and nanostructured lipid carriers (NLCs). Substances related to squalene, including β-carotene, coenzyme Q10 (ubiquinone) and vitamins A, E, and K, are also included in this review article to introduce their benefits to skin physiology. We summarize investigations performed in previous reports from both in vitro and in vivo models. Full article
(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)
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231 KiB  
Communication
“Flash” Solvent-free Synthesis of Triazoles Using a Supported Catalyst
by Ibtissem Jlalia, Faouzi Meganem, Jean Herscovici and Christian Girard
Molecules 2009, 14(1), 528-539; https://doi.org/10.3390/molecules14010528 - 22 Jan 2009
Cited by 30 | Viewed by 16400
Abstract
A solvent-free synthesis of 1,4-disubstituted-1,2,3-triazoles using neat azides and alkynes and a copper(I) polymer supported catalyst (Amberlyst® A21•CuI) is presented herein. As it provides the products in high yields and purities within minutes, this method thus being characterized as a "flash" synthesis, [...] Read more.
A solvent-free synthesis of 1,4-disubstituted-1,2,3-triazoles using neat azides and alkynes and a copper(I) polymer supported catalyst (Amberlyst® A21•CuI) is presented herein. As it provides the products in high yields and purities within minutes, this method thus being characterized as a "flash" synthesis, and was exemplified through the synthesis of a 24-compound library on a small scale. Full article
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151 KiB  
Article
Antimicrobial Activity of Some Thiourea Derivatives and Their Nickel and Copper Complexes
by Hakan Arslan, Nizami Duran, Gulay Borekci, Cemal Koray Ozer and Cevdet Akbay
Molecules 2009, 14(1), 519-527; https://doi.org/10.3390/molecules14010519 - 22 Jan 2009
Cited by 150 | Viewed by 18142
Abstract
Five thiourea derivative ligands and their Ni2+ and Cu2+ complexes have been synthesized. The compounds were screened for their in vitro anti-bacterial activity using Gram-positive bacteria (two different standard strains of Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Streptococcus [...] Read more.
Five thiourea derivative ligands and their Ni2+ and Cu2+ complexes have been synthesized. The compounds were screened for their in vitro anti-bacterial activity using Gram-positive bacteria (two different standard strains of Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Streptococcus pyogenes, Bacillus cereus) and Gram-negative bacteria (Esherichia coli, Pseudomonas aeruginosa, Enterobacter cloacae, Proteus vulgaris, Enterobacter aerogenes) and in vitro anti-yeast activity (Candida albicans, Candida krusei, Candida glabrata, Candida tropicalis, Candida parapsilosis). The minimum inhibitory concentration was determined for all ligands and their complexes. In vitro anti-yeast activity of both ligands and their metal complexes is greater than their in vitro anti-bacterial activity. The effect of the structure of the investigated compounds on the antimicrobial activity is discussed. Full article
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230 KiB  
Article
Antimutagenic Activity and Radical Scavenging Activity of Water Infusions and Phenolics from Ligustrum Plants Leaves
by Milan Nagy, Lívia Križková, Pavel Mučaji, Zuzana Kontšeková, František Šeršeň and Juraj Krajčovič
Molecules 2009, 14(1), 509-518; https://doi.org/10.3390/molecules14010509 - 22 Jan 2009
Cited by 41 | Viewed by 14958
Abstract
Water infusions of Ligustrum delavayanum and Ligustrum vulgare leaves and eight phenolics isolated therefrom have been assayed in vitro on ofloxacin-induced genotoxicity in the unicellular flagellate Euglena gracilis. The tested compounds luteolin, quercetin, luteolin-7-glucoside, luteolin-7-rutinoside, quercetin-3-rutinoside, apigenin-7-rutinoside, tyrosol and esculetin inhibited the [...] Read more.
Water infusions of Ligustrum delavayanum and Ligustrum vulgare leaves and eight phenolics isolated therefrom have been assayed in vitro on ofloxacin-induced genotoxicity in the unicellular flagellate Euglena gracilis. The tested compounds luteolin, quercetin, luteolin-7-glucoside, luteolin-7-rutinoside, quercetin-3-rutinoside, apigenin-7-rutinoside, tyrosol and esculetin inhibited the mutagenic activity of ofloxacin (43 µM) in E. gracilis. Water infusions from leaves of L. delavayanum and L. vulgare showed higher antimutagenic effect (pt < 0.001). The activity of these samples against ofloxacin (86 µM)-induced genotoxicity was lower, but statistically significant (pt < 0.05), excluding the water infusion of L. delavayanum leaves (pt < 0.01). Efficacy of quercetin, luteolin-7-rutinoside, apigenin-7-rutinoside was insignificant. The antimutagenic effect of most phenolics we studied could be clearly ascribed to their DPPH scavenging activity, substitution patterns and lipophilicity. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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420 KiB  
Article
2-Amido-3-(1H-Indol-3-yl)-N-Substitued-Propanamides as a New Class of Falcipain-2 Inhibitors. 1. Design, Synthesis, Biological Evaluation and Binding Model Studies
by Jin Zhu, Tong Chen, Lili Chen, Weiqiang Lu, Peng Che, Jin Huang, Honglin Li, Jian Li and Hualiang Jiang
Molecules 2009, 14(1), 494-508; https://doi.org/10.3390/molecules14010494 - 21 Jan 2009
Cited by 13 | Viewed by 17918
Abstract
The Plasmodium falciparum cysteine protease falcipain-2 (FP-2) is an important cysteine protease and an essential hemoglobinase of erythrocytic P. falciparum trophozoites. The discovery of new FP-2 inhibitors is now a hot topic in the search for potential malaria treatments. In this study, a [...] Read more.
The Plasmodium falciparum cysteine protease falcipain-2 (FP-2) is an important cysteine protease and an essential hemoglobinase of erythrocytic P. falciparum trophozoites. The discovery of new FP-2 inhibitors is now a hot topic in the search for potential malaria treatments. In this study, a series of novel small molecule FP-2 inhibitors have been designed and synthesized based on three regional optimizations of the lead (R)-2-phenoxycarboxamido-3-(1H-indol-3-yl)-N-benzylpropanamide(1), which was identified using structure-based virtual screening in conjunction with surface plasmon resonance (SPR)-based binding assays. Four compounds – 1, 2b, 2k and 2l –showed moderate FP-2 inhibition activity, with IC50 values of 10.0-39.4 μM, and the inhibitory activityof compound 2k was ~3-fold better than that of the prototype compound 1 and may prove useful for the development of micromolar level FP-2 inhibitors. Preliminary SAR data was obtained, while molecular modeling revealed that introduction of H-bond donor or/and acceptor atoms to the phenyl ring moiety in the C region would be likely to produce some additional H-bond interactions, which should consequently enhance molecular bioactivity. Full article
(This article belongs to the Special Issue Neglected Diseases: Medicinal Chemistry and Natural Product Chemistry)
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324 KiB  
Article
Total Antioxidant Capacity of Some Commercial Fruit Juices: Electrochemical and Spectrophotometrical Approaches
by Aurelia Magdalena Pisoschi, Mihaela Carmen Cheregi and Andrei Florin Danet
Molecules 2009, 14(1), 480-493; https://doi.org/10.3390/molecules14010480 - 20 Jan 2009
Cited by 122 | Viewed by 18076
Abstract
The aim of this paper was to assess the total antioxidant capacity of some commercial fruit juices (namely citrus), spectrophotometrically and by the biamperometric method, using the redox couple DPPH· (2,2-diphenyl-1-picrylhydrazyl)/DPPH (2,2-diphenyl-1-picrylhydrazine). Trolox® was chosen as a standard antioxidant. In the case [...] Read more.
The aim of this paper was to assess the total antioxidant capacity of some commercial fruit juices (namely citrus), spectrophotometrically and by the biamperometric method, using the redox couple DPPH· (2,2-diphenyl-1-picrylhydrazyl)/DPPH (2,2-diphenyl-1-picrylhydrazine). Trolox® was chosen as a standard antioxidant. In the case of the spectrophometric method, the absorbance decrease of the DPPH· solution was followed. For the biamperometric method, the influence of some parameters like the potential diference, ΔE, DPPH· concentration, and Trolox® concentration was investigated. The calibration graph obtained for Trolox® presents linearity between 5 and 30 µM, (y = 0.059 x + 0.0564, where y represents the value of current intensity, expressed as μA and x the value of Trolox® concentration, expressed as μM; r2 = 0.9944). The R.S.D. value for the biamperometric method was 1.29% (n = 10, c = 15 μM Trolox®). In the case of the spectrophotometric method, the calibration graph obtained for Trolox® presents linearity between 0.01 and 0.125 mM (y = -9.5789 x+1.4533, where y represents the value of absorbance and x, the value of Trolox® concentration, expressed as mM; r2 = 0.9963). The R.S.D. value for the spectrophotometric method was 2.05%. Both methods were applied to total antioxidant activity determination in real samples (natural juices and soft drinks) and the results were in good agreement. Full article
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50 KiB  
Article
Mechanochemical Solvent-Free and Catalyst-Free One-Pot Synthesis of Pyrano[2,3-d]Pyrimidine-2,4(1H,3H)-Diones with Quantitative Yields
by Sara Mashkouri and M. Reza Naimi-Jamal
Molecules 2009, 14(1), 474-479; https://doi.org/10.3390/molecules14010474 - 19 Jan 2009
Cited by 113 | Viewed by 14589
Abstract
Solvent-free synthesis of pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones by ball-milling and without any catalyst is described. This method provides several advantages such as being environmentally friendly, using a simple workup procedure, and affording high yields. Full article
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311 KiB  
Review
Phenolics: Occurrence and Immunochemical Detection in Environment and Food
by Eline P. Meulenberg
Molecules 2009, 14(1), 439-473; https://doi.org/10.3390/molecules14010439 - 19 Jan 2009
Cited by 29 | Viewed by 16488 | Correction
Abstract
Phenolic compounds may be of natural or anthropogenic origin and be present in the environment as well as in food. They comprise a large and diverse group of compounds that may be either beneficial or harmful for consumers. In this review first a [...] Read more.
Phenolic compounds may be of natural or anthropogenic origin and be present in the environment as well as in food. They comprise a large and diverse group of compounds that may be either beneficial or harmful for consumers. In this review first a non-exhausting overview of interesting phenolics is given, in particular with regards to their presence in environment and food. For some of these compounds, beneficial, toxicological and/or optionally endocrine disrupting activities will be presented. Further, immunochemical detection and/or isolation methods developed will be discussed, including advantages and disadvantages thereof in comparison with conventional analytical methods such as HPLC, GC, MS. A short overview of new sensor-like methods will also be included for present and future application. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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765 KiB  
Review
Multiscale Modeling of Dendrimers and Their Interactions with Bilayers and Polyelectrolytes
by Hwankyu Lee and Ronald G. Larson
Molecules 2009, 14(1), 423-438; https://doi.org/10.3390/molecules14010423 - 19 Jan 2009
Cited by 86 | Viewed by 17608
Abstract
Recent advances in molecular dynamics simulation methodologies and computational power have allowed accurate predictions of dendrimer size, shape, and interactions with bilayers and polyelectrolytes with modest computational effort. Atomistic and coarse-grained (CG) models show strong interactions of cationic dendrimers with lipid bilayers. The [...] Read more.
Recent advances in molecular dynamics simulation methodologies and computational power have allowed accurate predictions of dendrimer size, shape, and interactions with bilayers and polyelectrolytes with modest computational effort. Atomistic and coarse-grained (CG) models show strong interactions of cationic dendrimers with lipid bilayers. The CG simulations with explicit lipid and water capture bilayer penetration and pore formation, showing that pore formation is enhanced at high dendrimer concentration, but suppressed at low temperature and high salt concentration, in agreement with experiments. Cationic linear polymers have also been simulated, but do not perforate membranes, evidently because by deforming into a pancake, the charges on a linear polymer achieve intimate contact with a single bilayer leaflet. The relatively rigid dendrimers, on the other hand, penetrate the bilayer, because only by interacting with both leaflets can they achieve a similar degree of contact between charged groups. Also, a “dendrimer-filled vesicle” structure for the dendrimer-membrane interaction is predicted by mesoscale thermodynamic simulations, in agreement with a picture derived from experimental observations. In simulations of complexes of dendrimer and polyelectrolyte, anionic linear chains wrap around the cationic dendrimer and penetrate inside it. Overall, these new results indicate that simulations can now provide predictions in excellent agreement with experimental observations, and provide atomic-scale insights into dendrimer structure and dynamics. Full article
(This article belongs to the Special Issue Dendrimers - from Synthesis to Applications)
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188 KiB  
Communication
A New Atisane-Type Diterpene from the Bark of the Mangrove Plant Excoecaria Agallocha
by Zhan Chang Wang, Yi Ming Lin, Dan Qin Feng, Cai Huan Ke, Peng Lin, Chong Ling Yan and Jun De Chen
Molecules 2009, 14(1), 414-422; https://doi.org/10.3390/molecules14010414 - 16 Jan 2009
Cited by 24 | Viewed by 15750
Abstract
A new atisane-type diterpene, ent-16α-hydroxy-atisane-3,4-lactone (4) and three known diterpenes, ent-16α-hydroxy-atisane-3-one (1), ent-atisane-3β,16α-diol (2), ent-3,4-seco-16α-hydroxyatis- 4(19)-en -3-oic acid (3) were isolated from the bark of the mangrove plant Excoecaria agallocha. Their structures and relative stereochemistry were elucidated by [...] Read more.
A new atisane-type diterpene, ent-16α-hydroxy-atisane-3,4-lactone (4) and three known diterpenes, ent-16α-hydroxy-atisane-3-one (1), ent-atisane-3β,16α-diol (2), ent-3,4-seco-16α-hydroxyatis- 4(19)-en -3-oic acid (3) were isolated from the bark of the mangrove plant Excoecaria agallocha. Their structures and relative stereochemistry were elucidated by means of extensive NMR and MS analysis. Compound 3 exhibited significant anti-microfouling activity against the adherence of Pseudomonas pseudoalcaligenes, with an EC50 value of 0.54 ± 0.01 ppm. Full article
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145 KiB  
Correction
Correction: Wang, Z.-N., et al. A New Cytotoxic Pregnanone from Calotropis gigantean. Molecules 2008, 13, 3033-3039.
by Zhu-Nian Wang, Mao-Yuan Wang, Wen-Li Mei, Zhuang Han and Hao-Fu Dai
Molecules 2009, 14(1), 412-413; https://doi.org/10.3390/molecules14010412 - 15 Jan 2009
Viewed by 10312
Abstract
n/a Full article
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72 KiB  
Article
Microwave Assisted Reactions of Some Azaheterocylic Compounds
by Gheorghita Zbancioc, Vasilichia Bejan, Marian Risca, Costel Moldoveanu and Ionel I. Mangalagiu
Molecules 2009, 14(1), 403-411; https://doi.org/10.3390/molecules14010403 - 15 Jan 2009
Cited by 31 | Viewed by 15120
Abstract
A fast, general, environmentally friendly and facile method for preparation of five- and six-membered ring diazaheterocylic salts under microwave irradiation is presented. The N-alkylation reactions of imidazole, pyrimidine, pyridazine and phthalazine have been studied. The microwaves remarkably accelerated these N-alkylations, the [...] Read more.
A fast, general, environmentally friendly and facile method for preparation of five- and six-membered ring diazaheterocylic salts under microwave irradiation is presented. The N-alkylation reactions of imidazole, pyrimidine, pyridazine and phthalazine have been studied. The microwaves remarkably accelerated these N-alkylations, the reaction times decreased dramatically, the reaction conditions were milder, the consumed energy decreased considerably and the amount of solvents used was reduced substantially. Consequently, the microwave assisted alkylation of N-containing heterocycles could be considered eco-friendly. In some cases, under MW irradiation the yields are also higher. A comparative study of microwave vs. classical conditions (liquid solvents) has been done. Twelve new diazaheterocylic salts of potential practical interest were obtained. Full article
(This article belongs to the Special Issue Microwave Assisted Synthesis)
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214 KiB  
Article
2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities
by Hans-Georg Häcker, Florian Grundmann, Friederike Lohr, Philipp A. Ottersbach, Jing Zhou, Gregor Schnakenburg and Michael Gütschow
Molecules 2009, 14(1), 378-402; https://doi.org/10.3390/molecules14010378 - 14 Jan 2009
Cited by 20 | Viewed by 48500
Abstract
The synthetic access to 2-sec-amino-4H-3,1-benzothiazin-4-ones 2 was explored. Compounds 2 were available from methyl 2-thioureidobenzoates 1, 2-thioureidobenzoic acids 3, and novel 2-thioureidobenzamides 6, respectively, under different conditions. 2-Alkylthio-4H-3,1-benzothiazin-4-ones 5 have been prepared from anthranilic acid following a [...] Read more.
The synthetic access to 2-sec-amino-4H-3,1-benzothiazin-4-ones 2 was explored. Compounds 2 were available from methyl 2-thioureidobenzoates 1, 2-thioureidobenzoic acids 3, and novel 2-thioureidobenzamides 6, respectively, under different conditions. 2-Alkylthio-4H-3,1-benzothiazin-4-ones 5 have been prepared from anthranilic acid following a two step route. Both, benzothiazinones 2 and 5 underwent ring cleavage reactions to produce thioureas 1 and 6, respectively. Twelve benzothiazinones were evaluated as inhibitors against a panel of eight proteases and esterases to identify one selective inhibitor of human cathepsin L, 2b, and one selective inhibitor of human leukocyte elastase, 5i. Full article
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327 KiB  
Article
Synthesis and Analysis of Resorcinol-Acetone Copolymer
by Ataru Kobayashi and Gen-ichi Konishi
Molecules 2009, 14(1), 364-377; https://doi.org/10.3390/molecules14010364 - 13 Jan 2009
Cited by 13 | Viewed by 16739
Abstract
Synthesis and characterization of resorcinol-acetone copolymer is described. The polymer was prepared by trifluoroacetic acid-catalyzed polymerization of resorcinol with acetone. According to the 1H-NMR, 13C-NMR, and MALDI-TOF Mass spectra data, the obtained polymer had three types of repeating units: isopropylidene bridged-resorcinol, [...] Read more.
Synthesis and characterization of resorcinol-acetone copolymer is described. The polymer was prepared by trifluoroacetic acid-catalyzed polymerization of resorcinol with acetone. According to the 1H-NMR, 13C-NMR, and MALDI-TOF Mass spectra data, the obtained polymer had three types of repeating units: isopropylidene bridged-resorcinol, chromane ring, and spiro-shaped double chromane ring, indicating that polymerization proceeded via simultaneous addition-condensation and cyclization of resorcinol with acetone. The obtained polymer can be useful not only for the development of plastic materials such as thermosets, adhesives, and coatings but also for the synthesis of biomaterials such as antimicrobial agents, pesticides, and medicines. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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73 KiB  
Article
Parallel Synthesis of a Library of Symmetrically- and Dissymmetrically-disubstituted Imidazole-4,5-dicarboxamides Bearing Amino Acid Esters
by Rosanna Solinas, John C. DiCesare and Paul W. Baures
Molecules 2009, 14(1), 352-363; https://doi.org/10.3390/molecules14010352 - 13 Jan 2009
Cited by 7 | Viewed by 12141
Abstract
The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters to afford symmetrically- and dissymmetrically-disubstituted imidazole-4,5-dicarboxamides with intramolecularly hydrogen bonded conformations that predispose the presentation of amino acid pharmacophores. In this work, a total of 45 imidazole-4,5-dicarboxamides bearing amino acid esters were [...] Read more.
The imidazole-4,5-dicarboxylic acid scaffold is readily derivatized with amino acid esters to afford symmetrically- and dissymmetrically-disubstituted imidazole-4,5-dicarboxamides with intramolecularly hydrogen bonded conformations that predispose the presentation of amino acid pharmacophores. In this work, a total of 45 imidazole-4,5-dicarboxamides bearing amino acid esters were prepared by parallel synthesis. The library members were purified by column chromatography on silica gel and the purified compounds characterized by LC-MS with LC detection at 214 nm. A selection of the final compounds was also analyzed by 1H-NMR spectroscopy. The analytically pure final products have been submitted to the Molecular Library Small Molecule Repository (MLSMR) for screening in the Molecular Library Screening Center Network (MLSCN) as part of the NIH Roadmap. Full article
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277 KiB  
Review
Vitamin B6: A Long Known Compound of Surprising Complexity
by Sutton Mooney, Jan-Erik Leuendorf, Christopher Hendrickson and Hanjo Hellmann
Molecules 2009, 14(1), 329-351; https://doi.org/10.3390/molecules14010329 - 12 Jan 2009
Cited by 209 | Viewed by 32594
Abstract
In recent years vitamin B6 has become a focus of research describing the compound’s critical function in cellular metabolism and stress response. For many years the sole function of vitamin B6 was considered to be that of an enzymatic cofactor. However, recently it [...] Read more.
In recent years vitamin B6 has become a focus of research describing the compound’s critical function in cellular metabolism and stress response. For many years the sole function of vitamin B6 was considered to be that of an enzymatic cofactor. However, recently it became clear that it is also a potent antioxidant that effectively quenches reactive oxygen species and is thus of high importance for cellular well-being. In view of the recent findings, the current review takes a look back and summarizes the discovery of vitamin B6 and the elucidation of its structure and biosynthetic pathways. It provides a detailed overview on vitamin B6 both as a cofactor and a protective compound. Besides these general characteristics of the vitamin, the review also outlines the current literature on vitamin B6 derivatives and elaborates on recent findings that provide new insights into transport and catabolism of the compound and on its impact on human health. Full article
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113 KiB  
Communication
Antimicrobial Activity of Some Water Plants from the Northeastern Anatolian Region of Turkey
by Hanife Özbay and Ahmet Alim
Molecules 2009, 14(1), 321-328; https://doi.org/10.3390/molecules14010321 - 12 Jan 2009
Cited by 18 | Viewed by 13390
Abstract
The antimicrobial activity of methanol and acetone extracts of Butomus umbellatus, Polygonum amphibium, and two species of the genus Sparganium (S. erectum and S. emersum)against three Gram-positive, five Gram-negative bacteria and one fungus was assessed by the disk diffusion method. The [...] Read more.
The antimicrobial activity of methanol and acetone extracts of Butomus umbellatus, Polygonum amphibium, and two species of the genus Sparganium (S. erectum and S. emersum)against three Gram-positive, five Gram-negative bacteria and one fungus was assessed by the disk diffusion method. The microorganisms used were Staphylococcus aureusATCC-29740, Escherichia coli ATCC-25922, Pseudomonas aeruginosa ATCC-15442, Salmonella typhi NCTC-9394, Klebsiella pneumoniae NCTC-5046, Proteus vulgaris ATCC-7829, Bacillus subtilis ATCC-6633, Corynebacterium diphteriae RSHM-633 and Candida albicans ATCC-10231. Methanol extracts of the plants did not exhibit any inhibitory activity against any of the microorganisms, while the acetone extracts of the all tested plants only showed significant activity against Bacillus subtilis, with inhibition zones and minimal inhibitory concentration values in the 7-16 mm and 0.49-12.50 mg/mL ranges, respectively. Full article
195 KiB  
Review
Methodologies for the Extraction of Phenolic Compounds from Environmental Samples: New Approaches
by Cristina Mahugo Santana, Zoraida Sosa Ferrera, M. Esther Torres Padrón and José Juan Santana Rodríguez
Molecules 2009, 14(1), 298-320; https://doi.org/10.3390/molecules14010298 - 9 Jan 2009
Cited by 238 | Viewed by 37288
Abstract
Phenolic derivatives are among the most important contaminants present in the environment. These compounds are used in several industrial processes to manufacture chemicals such as pesticides, explosives, drugs and dyes. They also are used in the bleaching process of paper manufacturing. Apart from [...] Read more.
Phenolic derivatives are among the most important contaminants present in the environment. These compounds are used in several industrial processes to manufacture chemicals such as pesticides, explosives, drugs and dyes. They also are used in the bleaching process of paper manufacturing. Apart from these sources, phenolic compounds have substantial applications in agriculture as herbicides, insecticides and fungicides. However, phenolic compounds are not only generated by human activity, but they are also formed naturally, e.g., during the decomposition of leaves or wood. As a result of these applications, they are found in soils and sediments and this often leads to wastewater and ground water contamination. Owing to their high toxicity and persistence in the environment, both, the US Environmental Protection Agency (EPA) and the European Union have included some of them in their lists of priority pollutants. Current standard methods of phenolic compounds analysis in water samples are based on liquid–liquid extraction (LLE) while Soxhlet extraction is the most used technique for isolating phenols from solid matrices. However, these techniques require extensive cleanup procedures that are time-intensive and involve expensive and hazardous organic solvents, which are undesirable for health and disposal reasons. In the last years, the use of news methodologies such as solid-phase extraction (SPE) and solid-phase microextraction (SPME) have increased for the extraction of phenolic compounds from liquid samples. In the case of solid samples, microwave assisted extraction (MAE) is demonstrated to be an efficient technique for the extraction of these compounds. In this work we review the developed methods in the extraction and determination of phenolic derivatives in different types of environmental matrices such as water, sediments and soils. Moreover, we present the new approach in the use of micellar media coupled with SPME process for the extraction of phenolic compounds. The advantages of micellar media over conventional extractants are reduction of organic solvent, low cost, easy handling and shorter time procedures. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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178 KiB  
Article
Antioxidant Phenolic Substances of Turkish Red Wines from Different Wine Regions
by R. Ertan Anli and Nilüfer Vural
Molecules 2009, 14(1), 289-297; https://doi.org/10.3390/molecules14010289 - 9 Jan 2009
Cited by 35 | Viewed by 16339
Abstract
In this study, five biologically phenolic antioxidant Turkish red wines from different regions of Turkey were determined using HPLC with PDA detection. The antioxidant capacities (AC) of the investigated wines are also determined and the relationship between the phenol content and antioxidant capacity [...] Read more.
In this study, five biologically phenolic antioxidant Turkish red wines from different regions of Turkey were determined using HPLC with PDA detection. The antioxidant capacities (AC) of the investigated wines are also determined and the relationship between the phenol content and antioxidant capacity is discussed. The results show that Kalecik Karası, Merlot and Cabernet Sauvignon AC values ranged between 15.8-18.7 mmol/L, 15.8-17.6 mmol/L and 18.1-22.6 mmol/L, respectively. Generally, Cabernet Sauvignon wines not only had higher levels of phenolic antioxidants, such as catechin, epicatechin and gallic acid, but also higher antioxidant capacities compared to Kalecik Karası and Merlot wines. When the results were compared on the basis of geographical area, Aegean red wines were found to contain generally higher levels of biologically important phenolics and thus to have more antioxidant capacity compared to the wines of the other regions studied. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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126 KiB  
Article
Screening of Agelasine D and Analogs for Inhibitory Activity against Pathogenic Protozoa; Identification of Hits for Visceral Leishmaniasis and Chagas Disease
by Anders Vik, Ágnes Proszenyák, Marieke Vermeersch, Paul Cos, Louis Maes and Lise-Lotte Gundersen
Molecules 2009, 14(1), 279-288; https://doi.org/10.3390/molecules14010279 - 8 Jan 2009
Cited by 46 | Viewed by 16725
Abstract
There is an urgent need for novel and improved drugs against several tropical diseases caused by protozoa. The marine sponge (Agelas sp.) metabolite agelasine D, as well as other agelasine analogs and related structures were screened for inhibitory activity against Plasmodium falciparum, [...] Read more.
There is an urgent need for novel and improved drugs against several tropical diseases caused by protozoa. The marine sponge (Agelas sp.) metabolite agelasine D, as well as other agelasine analogs and related structures were screened for inhibitory activity against Plasmodium falciparum, Leishmania infantum, Trypanosoma brucei and T. cruzi, as well as for toxicity against MRC-5 fibroblast cells. Many compounds displayed high general toxicity towards both the protozoa and MRC-5 cells. However, two compounds exhibited more selective inhibitory activity against L. infantum (IC50 <0.5 mg/mL) while two others displayed IC50 <1 mg/mL against T. cruzi in combination with relatively low toxicity against MRC-5 cells. According to criteria set up by the WHO Special Programme for Research & Training in Tropical Diseases (TDR), these compounds could be classified as hits for leishmaniasisand for Chagas disease, respectively. Identification of the hits as well as other SAR data from this initial screening will be valuable for design of more potent and selective potential drugs against these neglected tropical diseases. Full article
(This article belongs to the Special Issue Neglected Diseases: Medicinal Chemistry and Natural Product Chemistry)
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142 KiB  
Article
The Main Chemical Composition and in vitro Antifungal Activity of the Essential Oils of Ocimum basilicum Linn. var. pilosum (Willd.) Benth
by Ji-Wen Zhang, Sheng-Kun Li and Wen-Jun Wu
Molecules 2009, 14(1), 273-278; https://doi.org/10.3390/molecules14010273 - 8 Jan 2009
Cited by 73 | Viewed by 16027
Abstract
The essential oils of the aerial parts of Ocimum basilicum Linn.var. pilosum (Willd.) Benth., an endemic medicinal plant growing in China, was obtained by hydrodistillation and analysed by GC-MS. Fifteen compounds, representing 74.19% of the total oil were identified. The main [...] Read more.
The essential oils of the aerial parts of Ocimum basilicum Linn.var. pilosum (Willd.) Benth., an endemic medicinal plant growing in China, was obtained by hydrodistillation and analysed by GC-MS. Fifteen compounds, representing 74.19% of the total oil were identified. The main components were as follows: linalool (29.68%), (Z)-cinnamic acid methyl ester (21.49%), cyclohexene (4.41%), α- cadinol (3.99%), 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane (2.27%), 3,5-pyridine-dicarboxylic acid, 2,6-dimethyl-diethyl ester (2.01%), β-cubebene (1.97%), guaia-1(10),11-diene (1.58%), cadinene (1.41%) (E)-cinnamic acid methyl ester (1.36%) and β-guaiene (1.30%). The essential oils showed significant antifungal activity against some plant pathogenic fungi. Full article
184 KiB  
Article
Isolation of Betulinic Acid, its Methyl Ester and Guaiane Sesquiterpenoids with Protein Tyrosine Phosphatase 1B Inhibitory Activity from the Roots of Saussurea lappa C.B.Clarke
by Ji Young Choi, MinKyun Na, In Hyun Hwang, Seung Ho Lee, Eun Young Bae, Bo Yeon Kim and Jong Seog Ahn
Molecules 2009, 14(1), 266-272; https://doi.org/10.3390/molecules14010266 - 8 Jan 2009
Cited by 77 | Viewed by 16706
Abstract
Activity-guided fractionation of a MeOH extract of the roots of Saussurea lappa C.B.Clarke (Compositae), using an in vitro protein tyrosine phosphatase 1B (PTP1B) inhibition assay, led to the isolation of four active constituents: betulinic acid (1), betulinic acid methyl ester (2), mokko lactone [...] Read more.
Activity-guided fractionation of a MeOH extract of the roots of Saussurea lappa C.B.Clarke (Compositae), using an in vitro protein tyrosine phosphatase 1B (PTP1B) inhibition assay, led to the isolation of four active constituents: betulinic acid (1), betulinic acid methyl ester (2), mokko lactone (3) and dehydrocostuslactone (4), along with nine inactive compounds. Our findings indicate that betulinic acid (1) and its methyl ester 2, as well as the two guaiane sesquiterpenoids 3 and 4 are potential lead moieties for the development of new PTP1B inhibitors. Full article
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595 KiB  
Article
Molecular Docking Studies and Anti-Tyrosinase Activity of Thai Mango Seed Kernel Extract
by Saruth Nithitanakool, Pimolpan Pithayanukul, Rapepol Bavovada and Patchreenart Saparpakorn
Molecules 2009, 14(1), 257-265; https://doi.org/10.3390/molecules14010257 - 7 Jan 2009
Cited by 58 | Viewed by 22259
Abstract
The alcoholic extract from seed kernels of Thai mango (Mangifera indica L. cv. ‘Fahlun’) (Anacardiaceae) and its major phenolic principle (pentagalloylglucopyranose) exhibited potent, dose-dependent inhibitory effects on tyrosinase with respect to L-DOPA. Molecular docking studies revealed that the binding orientations of the [...] Read more.
The alcoholic extract from seed kernels of Thai mango (Mangifera indica L. cv. ‘Fahlun’) (Anacardiaceae) and its major phenolic principle (pentagalloylglucopyranose) exhibited potent, dose-dependent inhibitory effects on tyrosinase with respect to L-DOPA. Molecular docking studies revealed that the binding orientations of the phenolic principles were in the tyrosinase binding pocket and their orientations were located in the hydrophobic binding pocket surrounding the binuclear copper active site. The results indicated a possible mechanism for their anti-tyrosinase activity which may involve an ability to chelate the copper atoms which are required for the catalytic activity of tyrosinase. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Article
Synthesis of 2,3-Dioxo-5-(substituted)arylpyrroles and Their 2-Oxo-5-aryl-3-hydrazone Pyrrolidine Derivatives
by M. F. Mohammat, Z. Shaameri and A. S. Hamzah
Molecules 2009, 14(1), 250-256; https://doi.org/10.3390/molecules14010250 - 7 Jan 2009
Cited by 27 | Viewed by 13006
Abstract
Some novel2,3-dioxo-5-(substituted)arylpyrroles have been synthesized. Among these, pyrrolidine compound 1b was converted to 2,3-dioxo-5-aryl pyrrolidine 2b. Finally a set of hydrazone derivatives was obtained from the reaction of 2b with various hydrazine salts. The structures of all the new synthesized compounds were confirmed [...] Read more.
Some novel2,3-dioxo-5-(substituted)arylpyrroles have been synthesized. Among these, pyrrolidine compound 1b was converted to 2,3-dioxo-5-aryl pyrrolidine 2b. Finally a set of hydrazone derivatives was obtained from the reaction of 2b with various hydrazine salts. The structures of all the new synthesized compounds were confirmed by elemental analyses, IR and 1H-NMR spectra. Full article
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269 KiB  
Article
Chemical Composition of Essential Oilsof Thymus and Mentha Speciesand Their Antifungal Activities
by Marina D. Soković, Jelena Vukojević, Petar D. Marin, Dejan D. Brkić, Vlatka Vajs and Leo J. L. D. Van Griensven
Molecules 2009, 14(1), 238-249; https://doi.org/10.3390/molecules14010238 - 7 Jan 2009
Cited by 355 | Viewed by 28091
Abstract
The potential antifungal effects of Thymus vulgaris L., Thymus tosevii L., Mentha spicata L., and Mentha piperita L. (Labiatae) essential oils and their components against 17 micromycetal food poisoning, plant, animal and human pathogens are presented. The essential oils were obtained by hydrodestillation [...] Read more.
The potential antifungal effects of Thymus vulgaris L., Thymus tosevii L., Mentha spicata L., and Mentha piperita L. (Labiatae) essential oils and their components against 17 micromycetal food poisoning, plant, animal and human pathogens are presented. The essential oils were obtained by hydrodestillation of dried plant material. Their composition was determined by GC-MS. Identification of individual constituents was made by comparison with analytical standards, and by computer matching mass spectral data with those of the Wiley/NBS Library of Mass Spectra. MIC’s and MFC’s of the oils and their components were determined by dilution assays. Thymol (48.9%) and p-cymene (19.0%) were the main components of T. vulgaris, while carvacrol (12.8%), a-terpinyl acetate (12.3%), cis-myrtanol (11.2%) and thymol (10.4%) were dominant in T. tosevii. Both Thymus species showed very strong antifungal activities. In M. piperita oil menthol (37.4%), menthyl acetate (17.4%) and menthone (12.7%) were the main components, whereas those of M. spicata oil were carvone (69.5%) and menthone (21.9%). Mentha sp. showed strong antifungal activities, however lower than Thymus sp. The commercial fungicide, bifonazole, used as a control, had much lower antifungal activity than the oils and components investigated. It is concluded that essential oils of Thymus and Mentha species possess great antifungal potential and could be used as natural preservatives and fungicides. Full article
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224 KiB  
Review
The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems
by Brian D. Wagner
Molecules 2009, 14(1), 210-237; https://doi.org/10.3390/molecules14010210 - 6 Jan 2009
Cited by 355 | Viewed by 27448
Abstract
Coumarins, as a family of molecules, exhibit a wide range of fluorescence emission properties. In many cases, this fluorescence is extremely sensitive to the local environment of the molecule, especially the local polarity and microviscosity. In addition, coumarins show a wide range of [...] Read more.
Coumarins, as a family of molecules, exhibit a wide range of fluorescence emission properties. In many cases, this fluorescence is extremely sensitive to the local environment of the molecule, especially the local polarity and microviscosity. In addition, coumarins show a wide range of size, shape, and hydrophobicity. These properties make them especially useful as fluorescent probes of heterogeneous environments, such as supramolecular host cavities, micelles, polymers and solids. This article will review the use of coumarins to probe such heterogeneous systems using fluorescence spectroscopy. Full article
(This article belongs to the Special Issue Coumarins and Xanthones)
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