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Molecules, Volume 15, Issue 9 (September 2010) – 56 articles , Pages 5840-6677

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892 KiB  
Review
Structural and Pharmacological Effects of Ring-Closing Metathesis in Peptides
by Øyvind Jacobsen, Jo Klaveness and Pål Rongved
Molecules 2010, 15(9), 6638-6677; https://doi.org/10.3390/molecules15096638 - 21 Sep 2010
Cited by 36 | Viewed by 9431
Abstract
Applications of ring-closing alkene metathesis (RCM) in acyclic α- and β-peptides and closely related systems are reviewed, with a special emphasis on the structural and pharmacological effects of cyclization by RCM. Full article
(This article belongs to the Special Issue Ring-Closing Metathesis)
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179 KiB  
Article
The Antigerminative Activity of Twenty-Seven Monoterpenes
by Laura De Martino, Emilia Mancini, Luiz Fernando Rolim de Almeida and Vincenzo De Feo
Molecules 2010, 15(9), 6630-6637; https://doi.org/10.3390/molecules15096630 - 21 Sep 2010
Cited by 169 | Viewed by 13794
Abstract
Monoterpenes, the main constituents of essential oils, are known for their many biological activities. The present work studied the potential biological activity of twenty-seven monoterpenes, including monoterpene hydrocarbons and oxygenated ones, against seed germination and subsequent primary radicle growth of Raphanus sativus L. [...] Read more.
Monoterpenes, the main constituents of essential oils, are known for their many biological activities. The present work studied the potential biological activity of twenty-seven monoterpenes, including monoterpene hydrocarbons and oxygenated ones, against seed germination and subsequent primary radicle growth of Raphanus sativus L. (radish) and Lepidium sativum L. (garden cress), under laboratory conditions. The compounds, belonging to different chemical classes, showed different potency in affecting both parameters evaluated. The assayed compounds demonstrated a good inhibitory activity in a dose-dependent way. In general, radish seed is more sensitive than garden cress and its germination appeares more inhibited by alcohols; at the highest concentration tested, the more active substances were geraniol, borneol, (±)-β-citronellol and α-terpineol. Geraniol and carvone inhibited, in a significant way, the germination of garden cress, at the highest concentration tested. Radicle elongation of two test species was inhibited mainly by alcohols and ketones. Carvone inhibited the radicle elongation of both seeds, at almost all concentrations assayed, while 1,8-cineole inhibited their radicle elongation at the lowest concentrations (10−5 M, 10−6 M). Full article
(This article belongs to the Section Natural Products Chemistry)
151 KiB  
Article
Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]-Pyrazoles and Pyrazolo[1,5-a]Pyrimidines
by Hamad M. Al-Matar, Khaled D. Khalil, Aisha Y. Adam and Mohamed H. Elnagdi
Molecules 2010, 15(9), 6619-6629; https://doi.org/10.3390/molecules15096619 - 20 Sep 2010
Cited by 90 | Viewed by 13678
Abstract
Pyrano[2,3-c]pyrazoles are obtained via mixing ethyl acetoacetate, hydrazine hydrate, aldehydes or ketones and malononitrile in the absence of solvent. These same products were also obtained by reacting arylidenemalononitriles 3 with 3-methyl-2-pyrazolin-5-ones. NOE difference experiments confirmed that these products exist solely in [...] Read more.
Pyrano[2,3-c]pyrazoles are obtained via mixing ethyl acetoacetate, hydrazine hydrate, aldehydes or ketones and malononitrile in the absence of solvent. These same products were also obtained by reacting arylidenemalononitriles 3 with 3-methyl-2-pyrazolin-5-ones. NOE difference experiments confirmed that these products exist solely in the 2H form. Similar treatments of 3-amino-2-pyrazolin-5-one with arylidene-malononitrile afforded adduct 6. Similarly mixing ethyl cyanoacetate, hydrazine hydrate, aldehydes, with malononitrile gave the same product 6. A novel synthesis of 4-oxo-4H-pyrano[2,3-c]pyrazole (8) could be achieved via reacting 3-methyl-2-pyrazolin-5-one with a mixture of cyanoacetic acid and acetic anhydride. Similar treatment of 3-aminopyrazole 11 with the benzylidene-malononitrile produced the pyrazolo[2,3-a]pyrimidines 12a,b. Full article
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198 KiB  
Review
Kinin Receptor Antagonists as Potential Neuroprotective Agents in Central Nervous System Injury
by Emma Thornton, Jenna M Ziebell, Anna V Leonard and Robert Vink
Molecules 2010, 15(9), 6598-6618; https://doi.org/10.3390/molecules15096598 - 20 Sep 2010
Cited by 36 | Viewed by 10680
Abstract
Injury to the central nervous system initiates complex physiological, cellular and molecular processes that can result in neuronal cell death. Of interest to this review is the activation of the kinin family of neuropeptides, in particular bradykinin and substance P. These neuropeptides are [...] Read more.
Injury to the central nervous system initiates complex physiological, cellular and molecular processes that can result in neuronal cell death. Of interest to this review is the activation of the kinin family of neuropeptides, in particular bradykinin and substance P. These neuropeptides are known to have a potent pro-inflammatory role and can initiate neurogenic inflammation resulting in vasodilation, plasma extravasation and the subsequent development of edema. As inflammation and edema play an integral role in the progressive secondary injury that causes neurological deficits, this review critically examines kinin receptor antagonists as a potential neuroprotective intervention for acute brain injury, and more specifically, traumatic brain and spinal cord injury and stroke. Full article
(This article belongs to the Special Issue Neuroprotective Strategies)
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188 KiB  
Article
Synthesis of Chiral Macrocyclic or Linear Pyridine Carboxamides from Pyridine-2,6-dicarbonyl Dichloride as Antimicrobial Agents
by Rashad A. Al-Salahi, Mohamed A Al-Omar and Abd El-Galil E Amr
Molecules 2010, 15(9), 6588-6597; https://doi.org/10.3390/molecules15096588 - 20 Sep 2010
Cited by 55 | Viewed by 10306
Abstract
A series of chiral linear and macrocyclic bridged pyridines has been prepared starting from pyridine-2,6-dicarbonyl dichloride (2). The coupling of 1 with D-alanyl methyl ester gave 2,6-bis-D-alanyl pyridine methyl ester (3). Hydrazinolysis of 3 with hydrazine hydrate afforded bis-hydrazide 4. The latter was [...] Read more.
A series of chiral linear and macrocyclic bridged pyridines has been prepared starting from pyridine-2,6-dicarbonyl dichloride (2). The coupling of 1 with D-alanyl methyl ester gave 2,6-bis-D-alanyl pyridine methyl ester (3). Hydrazinolysis of 3 with hydrazine hydrate afforded bis-hydrazide 4. The latter was reacted with thiophene-2-carbaldehyde, phthalic anhydride or cyclohexanone to afford bis-carboxamide pyridine derivatives 5-7, respectively. Compound 4 was coupled with p-methoxy- or p-nitroaceto-phenone to yield compounds 8 and 9. In addition, 4 was reacted with 1,2,4,5-benzenetetra-carboxylic acid dianhydride or 1,4,5,8-naphthalenetetracarboxylic acid dianhydride to afford the macrocyclic octacarboxaamide pyridines 10 and 11. The detailed synthesis, spectroscopic data and antimicrobial screening for the synthesized compounds are reported. Full article
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223 KiB  
Communication
Variation of Oleanolic and Ursolic Acid in the Flesh of Persimmon Fruit among Different Cultivars
by Chunhua Zhou, Yanle Sheng, Daqiu Zhao, Zhiqin Wang and Jun Tao
Molecules 2010, 15(9), 6580-6587; https://doi.org/10.3390/molecules15096580 - 20 Sep 2010
Cited by 35 | Viewed by 8821
Abstract
Oleanolic acid (OA) and ursolic acid (UA) are important bioactive components in many plants, including persimmon (Diospyros kaki L.). The present work was carried out to determine OA and UA contents in the flesh of persimmon fruit from 32 cultivars, including 23 astringent [...] Read more.
Oleanolic acid (OA) and ursolic acid (UA) are important bioactive components in many plants, including persimmon (Diospyros kaki L.). The present work was carried out to determine OA and UA contents in the flesh of persimmon fruit from 32 cultivars, including 23 astringent and 9 non-astringent ones, by applying high performance liquid chromatography (HPLC) with UV detection. Both OA and UA were present in all of the investigated cultivars, except for three, ‘Hiratanenashi’, ‘Ribenhongshi’ and ‘Matsumotowase’. The OA content ranged from traces to 88.57 μg/g FW, and that of UA were between traces and 27.64 μg/g FW. Full article
(This article belongs to the Section Natural Products Chemistry)
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228 KiB  
Article
Determination of Quercetin and Resveratrol in Whole Blood—Implications for Bioavailability Studies
by Lucia Biasutto, Ester Marotta, Spiridione Garbisa, Mario Zoratti and Cristina Paradisi
Molecules 2010, 15(9), 6570-6579; https://doi.org/10.3390/molecules15096570 - 20 Sep 2010
Cited by 65 | Viewed by 12702
Abstract
Resveratrol (trans-3,4',5-trihydroxystilbene) and quercetin (3,3’,4’,5,7-pentahydroxyflavone) are two naturally occurring polyphenols with the potential to exert beneficial health effects. Since their low bioavailability is a major obstacle to biomedical applications, efforts are being made to improve their absorption and slow down phase [...] Read more.
Resveratrol (trans-3,4',5-trihydroxystilbene) and quercetin (3,3’,4’,5,7-pentahydroxyflavone) are two naturally occurring polyphenols with the potential to exert beneficial health effects. Since their low bioavailability is a major obstacle to biomedical applications, efforts are being made to improve their absorption and slow down phase II metabolism. An accurate evaluation of the corresponding levels in the bloodstream is important to assess delivery strategies, as well as to verify claims of efficacy based on in vitro results. In the present work we have optimized a simple method ensuring complete stabilization and extraction of resveratrol and quercetin from whole blood. The suitability of different protocols was evaluated by measuring the recovery of polyphenol and internal standard from spiked blood samples via HPLC/UV analysis. The optimized procedure ensured a satisfactory recovery of both internal standards and compounds. Comparing plasma and whole blood, up to 76% of the analyte, being associated with the cellular fraction, was unaccounted for when examining only plasma. This indicates the importance of analysing whole blood rather than plasma to avoid underestimating polyphenol absorption in bioavailability studies. Full article
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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2862 KiB  
Article
Correlation between Cytotoxic Activities and Reduction Potentials of Heterocyclic Quinones
by Junko Koyama, Izumi Morita and Takao Yamori
Molecules 2010, 15(9), 6559-6569; https://doi.org/10.3390/molecules15096559 - 20 Sep 2010
Cited by 18 | Viewed by 7672
Abstract
To search for possible anti-tumor agents or anti-tumor promoters among natural or synthetic products, we used cyclic voltammetry to determine the reduction-oxidation potentials of heterocyclic quinones in phosphate buffer at pH 7.2. We determined the growth inhibitory- and cytotoxic activities of 12 heterocyclic [...] Read more.
To search for possible anti-tumor agents or anti-tumor promoters among natural or synthetic products, we used cyclic voltammetry to determine the reduction-oxidation potentials of heterocyclic quinones in phosphate buffer at pH 7.2. We determined the growth inhibitory- and cytotoxic activities of 12 heterocyclic quinone anti-tumor agent candidates against a panel of 39 human cancer cell lines (JFCR39). The average concentrations of the heterocyclic quinones required for 50% growth inhibition (GI50) against JFCR39 ranged from 0.045 to 13.2 µM, and the 50% lethal concentration (LC50) against JFCR39 ranged from 0.398 to 77.7 µM. The average values of GI50 or LC50 of the heterocyclic quinones correlated significantly with their reduction potentials. These results suggested that reduction-oxidation potentials could be a useful method for the discovery of novel antitumor agents. Full article
(This article belongs to the Collection Bioactive Compounds)
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276 KiB  
Article
New 2-Arylbenzofurans from the Root Bark of Artocarpus lakoocha
by Boonchoo Sritularak, Kullasap Tantrakarnsakul, Kittisak Likhitwitayawuid and Vimolmas Lipipun
Molecules 2010, 15(9), 6548-6558; https://doi.org/10.3390/molecules15096548 - 17 Sep 2010
Cited by 15 | Viewed by 5736
Abstract
Three new prenylated 2-arylbenzofurans – artolakoochol, 4-hydroxy-artolakoochol and cycloartolakoochol – have been isolated from the root bark of Artocarpus lakoocha Roxb., Their structures were elucidated through analysis of their spectroscopic data, and their antiherpetic potential was evaluated by the plaque reduction assay. Full article
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1102 KiB  
Review
The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis
by Essi J. Karppanen and Ari M. P. Koskinen
Molecules 2010, 15(9), 6512-6547; https://doi.org/10.3390/molecules15096512 - 17 Sep 2010
Cited by 13 | Viewed by 10764
Abstract
One of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally [...] Read more.
One of the biggest challenges in asymmetric synthesis is to prevent racemization of enantiopure starting materials. However, at least some of the enantiopurity is lost in most of the existing reactions used in synthetic organic chemistry. This translates into unnecessary material losses. Naturally enantiopure proteinogenic amino acids that can be transformed into many useful intermediates in drug syntheses, for example, are especially vulnerable to this. The phenylfluoren-9-yl (Pf) group, a relatively rarely used protecting group, has proven to be able to prevent racemization in α-amino compounds. This review article showcases the use of Pf-protected amino acid derivatives in enantiospecific synthesis. Full article
(This article belongs to the Special Issue Protecting Group in Organic Synthesis)
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197 KiB  
Article
Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
by Luis Espinoza Catalán, Evelyn Baeza Maturana, Karen Catalán Marín, Mauricio Osorio Olivares, Héctor Carrasco Altamirano, Mauricio Cuellar Fritis and Joan Villena García
Molecules 2010, 15(9), 6502-6511; https://doi.org/10.3390/molecules15096502 - 17 Sep 2010
Cited by 12 | Viewed by 8789
Abstract
Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF [...] Read more.
Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF3.Et2O as a catalyst. These compounds, along with a series of natural ent-labdanes 3-8, have been evaluated for their in vitro cytotoxic activities against cultured human cancer cells of PC-3 and DU-145 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma and dermal human fibroblasts (DHF). Some compounds displayed inhibition at µM IC50 values. Full article
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184 KiB  
Article
An Efficient and Chemoselective Procedure for Acylal Synthesis
by Da-He Fan, Hui Wang, Xing-Xing Mao and Yong-Miao Shen
Molecules 2010, 15(9), 6493-6501; https://doi.org/10.3390/molecules15096493 - 16 Sep 2010
Cited by 8 | Viewed by 10355
Abstract
A novel heterogeneous efficient procedure has been developed for the chemoselective synthesis of acylals (1,1-diacetates) under solvent-free conditions. A novel catalyst prepared by the sulfuric acid catalyzed copolymerization of p-toluenesulfonic acid and paraformaldehyde displays extremely high activities for the title reactions, affording [...] Read more.
A novel heterogeneous efficient procedure has been developed for the chemoselective synthesis of acylals (1,1-diacetates) under solvent-free conditions. A novel catalyst prepared by the sulfuric acid catalyzed copolymerization of p-toluenesulfonic acid and paraformaldehyde displays extremely high activities for the title reactions, affording average yields over 90% within several minutes. A comparative study showed that the novel catalyst has much higher activity than other catalysts used for this purpose. Besides, the novel catalyst displays chemoselectivity for the protection of aldehydes in the presence of ketones. In addition the high acidity (4.0 mmol/g), thermal stability (200 ºC) and easy reusability make the novel catalyst one of the best choices for the process. Full article
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269 KiB  
Communication
Synthesis and Antifungal Activity of Carabrone Derivatives
by Jun-Tao Feng, Zhi-Qing Ma, Jiang-Hua Li, Jun He, Hui Xu and Xing Zhang
Molecules 2010, 15(9), 6485-6492; https://doi.org/10.3390/molecules15096485 - 16 Sep 2010
Cited by 20 | Viewed by 6662
Abstract
Nine derivatives 6-14 of carabrone (1) were synthesized and tested in vitro against Colletotrichum lagenarium Ell et Halst using the spore germination method. Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal activity than [...] Read more.
Nine derivatives 6-14 of carabrone (1) were synthesized and tested in vitro against Colletotrichum lagenarium Ell et Halst using the spore germination method. Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal activity than 1. Structure-activity relationships (SAR) demonstrated that the γ-lactone was necessary for the antifungal activity of 1, and the substituents on the C-4 position of 1 could significantly affect the antifungal activity. Full article
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125 KiB  
Communication
Isoquinolines from the Roots of Thalictrum flavum L. and Their Evaluation as Antiparasitic Compounds
by Jacqueline Ropivia, Séverine Derbré, Caroline Rouger, Fabrice Pagniez, Patrice Le Pape and Pascal Richomme
Molecules 2010, 15(9), 6476-6484; https://doi.org/10.3390/molecules15096476 - 16 Sep 2010
Cited by 22 | Viewed by 15972
Abstract
Alkaloids from Thalictrum flavum L. (Ranuculaceae) growing in the Loire valley (France) were isolated and evaluated for their antiplasmodial and leishmanicidal activities. Berberine was identified as a major component but its analogue, pseudoberberine, was isolated for the first time from this plant. As [...] Read more.
Alkaloids from Thalictrum flavum L. (Ranuculaceae) growing in the Loire valley (France) were isolated and evaluated for their antiplasmodial and leishmanicidal activities. Berberine was identified as a major component but its analogue, pseudoberberine, was isolated for the first time from this plant. As far as bisbenzylisoquinolines are concerned, thalfoetidine was also isolated and, besides, its nor- derivative, northalfoetidine, was identified as a new compound. Previously isolated alkaloids from Thalictrum species such as northalidasine, northalrugosidine, thaligosidine, thalicberine, thaliglucinone, preocoteine, O-methylcassythine and armepavine were newly described in the roots of T. flavum. Tertiary isoquinolines, and particularly bisbenzylisoquinolines, were found to be leishmanicidal against L. major. Thalfoetidine appeared as the most potent but its new nor- derivative northalfoetidine, as well as northalidasine, were of particular interest due to the fact that their potential leishmanicidal activity was not associated to a strong cytotoxicity. Full article
(This article belongs to the Section Natural Products Chemistry)
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357 KiB  
Article
Effects of Eupatilin and Jaceosidin on Cytochrome P450 Enzyme Activities in Human Liver Microsomes
by Hye Young Ji, Sung Yeon Kim, Dong Kyun Kim, Ji Hyun Jeong and Hye Suk Lee
Molecules 2010, 15(9), 6466-6475; https://doi.org/10.3390/molecules15096466 - 16 Sep 2010
Cited by 32 | Viewed by 11246
Abstract
Eupatilin and jaceosidin are bioactive flavones found in the medicinal herbs of the genus Artemisia. These bioactive flavones exhibit various antioxidant, antiinflammatory, antiallergic, and antitumor activities. The inhibitory potentials of eupatilin and jaceosidin on the activities of seven major human cytochrome P450 [...] Read more.
Eupatilin and jaceosidin are bioactive flavones found in the medicinal herbs of the genus Artemisia. These bioactive flavones exhibit various antioxidant, antiinflammatory, antiallergic, and antitumor activities. The inhibitory potentials of eupatilin and jaceosidin on the activities of seven major human cytochrome P450 enzymes in human liver microsomes were investigated using a cocktail probe assay. Eupatilin and jaceosidin potently inhibited CYP1A2-catalyzed phenacetin O-deethylation with 50% inhibitory concentration (IC50) values of 9.4 mM and 5.3 mM, respectively, and CYP2C9-catalyzed diclofenac 4-hydroxylation with IC50 values of 4.1 mM and 10.2 mM, respectively. Eupatilin and jaceosidin were also found to moderately inhibit CYP2C19-catalyzed [S]-mephenytoin 4¢-hydroxylation, CYP2D6-catalyzed bufuralol 1¢-hydroxylation, and CYP2C8-catalyzed amodiaquine N-deethylation. Kinetic analysis of human liver microsomes showed that eupatilin is a competitive inhibitor of CYP1A2 with a Ki value of 2.3 mM and a mixed-type inhibitor of CYP2C9 with a Ki value of 1.6 mM. Jaceosidin was shown to be a competitive inhibitor of CYP1A2 with a Ki value of 3.8 mM and a mixed-type inhibitor of CYP2C9 with Ki value of 6.4 mM in human liver microsomes. These in vitro results suggest that eupatilin and jaceosidin should be further examined for potential pharmacokinetic drug interactions in vivo due to inhibition of CYP1A2 and CYP2C9. Full article
(This article belongs to the Collection Bioactive Compounds)
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301 KiB  
Review
Honokiol and Magnolol as Multifunctional Antioxidative Molecules for Dermatologic Disorders
by Jui-Lung Shen, Kee-Ming Man, Po-Hsun Huang, Wen-Chi Chen, Der-Cherng Chen, Ya-Wen Cheng, Po-Len Liu, Ming-Chih Chou and Yung-Hsiang Chen
Molecules 2010, 15(9), 6452-6465; https://doi.org/10.3390/molecules15096452 - 16 Sep 2010
Cited by 135 | Viewed by 20742
Abstract
Chinese herbs have been and still are widely used as important remedies in Oriental medicine. Over the recent years, a variety of biologically active constituents have been isolated from these sources and confirmed to have multifunctional activity in experimental studies. Honokiol is a [...] Read more.
Chinese herbs have been and still are widely used as important remedies in Oriental medicine. Over the recent years, a variety of biologically active constituents have been isolated from these sources and confirmed to have multifunctional activity in experimental studies. Honokiol is a small-molecule polyphenol isolated from the genus Magnolia. It is accompanied by other related polyphenols, including magnolol, with which it shares certain biological properties. Recently, honokiol and magnolol have been found to have anti-oxidative, anti-inflammatory, anti-tumor, and anti-microbial properties in preclinical models, without appreciable toxicity. These findings have increased interest in bringing honokiol and magnolol to the clinic as novel therapeutic agents in dermatology. In this review, the findings concerning the major mechanisms of action of honokiol and magnolol are described. Knowledge of the multiple activities of honokiol and magnolol can assist with the development of honokiol and magnolol derivatives and the design of clinical trials that will maximize the potential benefit of honokiol and magnolol in the patient setting for dermatologic disorders. Full article
(This article belongs to the Special Issue Antioxidants)
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733 KiB  
Article
Anti-Inflammatory Activity of Chrysophanol through the Suppression of NF-kB/Caspase-1 Activation in Vitro and in Vivo
by Su-Jin Kim, Min-Cheol Kim, Byong-Joo Lee, Dae-Hee Park, Seung-Heon Hong and Jae-Young Um
Molecules 2010, 15(9), 6436-6451; https://doi.org/10.3390/molecules15096436 - 16 Sep 2010
Cited by 113 | Viewed by 13503
Abstract
Chrysophanol is a member of the anthraquinone family and has multiple pharmacological effects, but the exact mechanism of the anti-inflammatory effects of chrysophanol has yet to be thoroughly elucidated. In this study, we attempted to determine the effects of chrysophanol on dextran sulfate [...] Read more.
Chrysophanol is a member of the anthraquinone family and has multiple pharmacological effects, but the exact mechanism of the anti-inflammatory effects of chrysophanol has yet to be thoroughly elucidated. In this study, we attempted to determine the effects of chrysophanol on dextran sulfate sodium (DSS)-induced colitis and lipopolysaccharide (LPS)-induced inflammatory responses in mouse peritoneal macrophages. The findings of this study demonstrated that chrysophanol effectively attenuated overall clinical scores as well as various pathological markers of colitis. Additionally, chrysophanol inhibited the production of tumor necrosis factor (TNF)-a, interleukin (IL)-6 and the expression of cyclooxygenase (COX)-2 levels induced by LPS. We showed that this anti-inflammatory effect of chrysophanol is through suppression of the activation of NF-kB and caspase-1 in LPS-stimulated macrophages. These results provide novel insights into the pharmacological actions of chrysophanol as a potential molecule for use in the treatment of inflammatory diseases. Full article
(This article belongs to the Section Natural Products Chemistry)
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1157 KiB  
Article
Inhibitory Effect of Indigo Naturalis on Tumor Necrosis Factor-α-Induced Vascular Cell Adhesion Molecule-1 Expression in Human Umbilical Vein Endothelial Cells
by Hsin-Ning Chang, Jong-Hwei Su Pang, Sien-Hung Yang, Chi-Feng Hung, Chi-Hsin Chiang, Tung-Yi Lin and Yin-Ku Lin
Molecules 2010, 15(9), 6423-6435; https://doi.org/10.3390/molecules15096423 - 14 Sep 2010
Cited by 25 | Viewed by 9956
Abstract
The use of indigo naturalis to treat psoriasis has proved effective in our previous clinical studies. The present study was designed to examine the anti-inflammatory effect of indigo naturalis in primary cultured human umbilical vein endothelial cells (HUVECs). Pretreatment of cells with indigo [...] Read more.
The use of indigo naturalis to treat psoriasis has proved effective in our previous clinical studies. The present study was designed to examine the anti-inflammatory effect of indigo naturalis in primary cultured human umbilical vein endothelial cells (HUVECs). Pretreatment of cells with indigo naturalis extract attenuated TNF-α-induced increase in Jurkat T cell adhesion to HUVECs as well as decreased the protein and messenger (m)RNA expression levels of vascular cell adhesion molecule-1 (VCAM-1) on HUVECs. Indigo naturalis extract also inhibited the protein expression of activator protein-1 (AP-1)/c-Jun, a critical transcription factor for the activation of VCAM-1 gene expression. Since the reduction of lymphocyte adhesion to vascular cells by indigo naturalis extract could subsequently reduce the inflammatory reactions caused by lymphocyte infiltration in the epidermal layer and help to improve psoriasis, this study provides a potential mechanism for the anti-inflammatory therapeutic effect of indigo naturalis extract in psoriasis. Full article
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180 KiB  
Article
Chemical Analysis and Biological Activity of the Essential Oils of Two Valerianaceous Species from China: Nardostachys chinensis and Valeriana officinalis
by Jihua Wang, Jianglin Zhao, Hao Liu, Ligang Zhou, Zhilong Liu, Jingguo Wang, Jianguo Han, Zhu Yu and Fuyu Yang
Molecules 2010, 15(9), 6411-6422; https://doi.org/10.3390/molecules15096411 - 14 Sep 2010
Cited by 91 | Viewed by 11824
Abstract
In order to investigate essential oils with biological activity from local wild plants, two valerianaceous species, Nardostachys chinensis and Valeriana officinalis, were screened for their antimicrobial and antioxidant activity. The essential oils were obtained from the roots and rhizomes of the two [...] Read more.
In order to investigate essential oils with biological activity from local wild plants, two valerianaceous species, Nardostachys chinensis and Valeriana officinalis, were screened for their antimicrobial and antioxidant activity. The essential oils were obtained from the roots and rhizomes of the two plants by hydro-distillation, and were analyzed for their chemical composition by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Calarene (25.31%), aristolone (13.35%), α-selinene (7.32%) and β-maaliene (6.70%) were the major compounds of the 23 identified components which accounted for 92.76% of the total oil of N. chinensis. Patchoulol (16.75%), α-pinene (14.81%), and β-humulene (8.19%) were the major compounds among the 20 identified components, which accounted for 88.11% of the total oil of V. officinalis. Both oils were rich in sesquiterpene hydrocarbons as well as their oxygenated derivatives. Essential oils were shown to have broad spectrum antibacterial activity with MIC values that ranged from 62.5 μg/mL to 400 μg/mL, and IC50 values from 36.93 μg/mL to 374.72 μg/mL. The oils were also shown to have moderate antifungal activity to Candida albicans growth as well as inhibition of spore germination of Magnaporthe oryzae. Two essential oils were assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging, β-carotene bleaching and ferrozine-ferrous ions assays, respectively, to show moderate antioxidant activity. Results suggest that the isolated essential oils could be used for future development of antimicrobial and antioxidant agents. Full article
282 KiB  
Article
Solid-Phase Synthesis and Evaluation of Glycopeptide Fragments from Rat Epididymal Cysteine-Rich Secretory Protein-1 (Crisp-1)
by Mian Liu, David W. Hamilton and George Barany
Molecules 2010, 15(9), 6399-6410; https://doi.org/10.3390/molecules15096399 - 14 Sep 2010
Cited by 2 | Viewed by 10140
Abstract
Three 18-residue peptides with the sequence Glp-Asp-Thr-Thr-Asp-Glu-Trp-Asp-Arg-Asp-Leu-Glu-Asn-Leu-Ser-Thr-Thr-Lys, taken from the N-terminus of the rat epididymal cysteine-rich secretory protein (Crisp-1) that is important in the fertilization process, were prepared by Fmoc solid-phase synthesis using a convergent strategy. These [...] Read more.
Three 18-residue peptides with the sequence Glp-Asp-Thr-Thr-Asp-Glu-Trp-Asp-Arg-Asp-Leu-Glu-Asn-Leu-Ser-Thr-Thr-Lys, taken from the N-terminus of the rat epididymal cysteine-rich secretory protein (Crisp-1) that is important in the fertilization process, were prepared by Fmoc solid-phase synthesis using a convergent strategy. These peptides were the parent sequence, plus two possible α-O-linked TN antigen-containing glycopeptides with a Thr(α-D-GalNAc) residue in place of either Thr3 or Thr4. During chain assembly, two deletion peptides [des-Asp2 and des-Thr(Ac3-α-D-GalNAc)] and one terminated peptide [N-acetylated 14-mer] arose, as did several peptides in which aspartimide formation had occurred at each of the four possible positions in the sequence. These by-products totaled ~20% of the desired product; they were recognized by HPLC and ESI-MS and removed during the intermediate purifications. Final products, obtained in 15-21% overall yields, were characterized by HPLC purities and ESI-MS. Circular dichroism (CD) spectra for all three purified peptides, recorded in pure water and in trifluoroethanol-H2O (1:1), revealed that the presence of a sugar moiety does not significantly impact the sampled conformations. Future biological evaluation could elucidate the nature and locus of sugar modification of Crisp-1, and provide insight as to why Crisp-1 protein E binds sperm irreversibly, in contrast to protein D that lacks a sugar near the N-terminus and only binds sperm loosely. Full article
(This article belongs to the Special Issue Solid Phase Synthesis)
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196 KiB  
Article
Bio-guided Isolation of Antioxidant Compounds from Chrysophyllum perpulchrum, a Plant Used in the Ivory Coast Pharmacopeia
by Bidie Alain Philippe, Ndjoko Karine, Attioua Koffi Barthélemy, Zirihi Guédé Noél, N’guessan Jean David, Djaman Allico Joseph and Kurt Hosttetmann
Molecules 2010, 15(9), 6386-6398; https://doi.org/10.3390/molecules15096386 - 13 Sep 2010
Cited by 15 | Viewed by 9019
Abstract
Chrysophyllum perpulchrum (Sapotaceae) is used in the traditional Ivory Coast pharmacopeia to cure fevers. The extract of C. perpulchrum used for this study was the powdered form obtained from the maceration of the dried plant bark in 96% methanol, followed by evaporation to [...] Read more.
Chrysophyllum perpulchrum (Sapotaceae) is used in the traditional Ivory Coast pharmacopeia to cure fevers. The extract of C. perpulchrum used for this study was the powdered form obtained from the maceration of the dried plant bark in 96% methanol, followed by evaporation to dryness. In the present study, the antioxidative and radical-scavenging activities of the methanolic extract were studied with three standard biological tests: DPPH reduction, ferric thiocyanate (FTC) lipidic peroxidation inhibition and thiobarbituric acid reacting substances (TBARS). Gallic acid and quercetin were used as references. The total amount of phenolic compounds in the extract was determined by ultraviolet (UV) spectrometry and calculated as gallic acid equivalents. Catechin and two dimeric procyanidins were found to be the compounds responsible for the activities. They were chemically dereplicated in the extract by LC-MS. For quantitation purposes, they were isolated by successive chromatographic methods and characterized by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectrometry. The quantities of these compounds in C. perpulchrum were 5.4% for catechin (P1), and 5.6 and 9.2% for dimers (compounds 2 (P2) and 3 (P3)), respectively. They displayed antioxidant activity with IC50 values of 2.50 ± 0.15 µg/mL (P1), 2.10 ± 0.2 µg/mL (P2) and 2.10 ± 0.1 µg/mL (P3). The total extract, the active fractions and the pure compounds inhibited the lipid peroxidation by the FTC method and the TBARS method in the range of 60%. These values were comparable to those seen for quercetin. Full article
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253 KiB  
Article
Composition of Sulla (Hedysarum coronarium L.) Honey Solvent Extractives Determined by GC/MS: Norisoprenoids and Other Volatile Organic Compounds
by Igor Jerković, Carlo I.G. Tuberso, Mirko Gugić and Dragan Bubalo
Molecules 2010, 15(9), 6375-6385; https://doi.org/10.3390/molecules15096375 - 09 Sep 2010
Cited by 31 | Viewed by 11648 | Correction
Abstract
Samples of unifloral sulla (Hedysarum coronarum L.) honey from Sardinia (Italy) were analysed. To investigate the chemical composition of the honey volatiles two solvent systems were used for ultrasonic solvent extraction (USE): 1) a 1:2 (v/v) pentane and diethyl ether mixture and [...] Read more.
Samples of unifloral sulla (Hedysarum coronarum L.) honey from Sardinia (Italy) were analysed. To investigate the chemical composition of the honey volatiles two solvent systems were used for ultrasonic solvent extraction (USE): 1) a 1:2 (v/v) pentane and diethyl ether mixture and 2) dichloromethane. All the extracts were analysed by GC and GC/MS. These procedures have permitted the identification of 56 compounds that include norisoprenoids, benzene derivatives, aliphatic compounds and Maillard reaction products. Norisoprenoids were the major compounds in both extracts, dominated by vomifoliol (5.3-11.2%; 9.6-14.0%) followed by minor percentages of other norisoprenoids such as α-isophorone, 4-ketoisophorone, 3-oxo-α-ionol or 3-oxo-α-ionone. Other abundant single compounds in the extracts were 3-hydroxy-4-phenylbutan-2-one (0.8-5.4%; 0.6-5.7%) and methyl syringate (3.0-5.7%; 2.2-4.1%). The composition of the volatiles and semi-volatiles in the obtained extracts suggests that sulla honey is quite distinctive relative to the other honeys that have been chemically studied by GC/MS, but no specific markers of the honey botanical origin were found. Full article
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125 KiB  
Article
Microwave Assisted Extraction of Phenolic Compounds from Four Different Spices
by Monica Gallo, Rosalia Ferracane, Giulia Graziani, Alberto Ritieni and Vincenzo Fogliano
Molecules 2010, 15(9), 6365-6374; https://doi.org/10.3390/molecules15096365 - 09 Sep 2010
Cited by 123 | Viewed by 14017
Abstract
Spices and herbs are known not only for their taste, aroma and flavour, but also for their medical properties and value. Both spices and herbs have been used for centuries in traditional medical systems to cure various kinds of illnesses such as common [...] Read more.
Spices and herbs are known not only for their taste, aroma and flavour, but also for their medical properties and value. Both spices and herbs have been used for centuries in traditional medical systems to cure various kinds of illnesses such as common cold, diabetes, cough and cancers. The aim of this work was the comparison between two different extractive techniques in order to get qualitative and quantitative data regarding bioactive compounds of four different spices (Cinnamomum zeylanicum, Coriandrum sativum, Cuminum cyminum, Crocus sativus). The plants were extracted employing ultrasonication and microwave-assisted extractions. The efficiency of extraction of bioactive compounds obtained with the microwave extraction process was in general about four times higher than that resulting from sonication extraction. The various extracts obtained were analyzed for their antioxidant activity using ABTS, DPPH and FRAP assays and for their total polyphenolic content. It can be concluded that microwave-assisted extractions provide significant advantages in terms of extraction efficiency and time savings. Full article
(This article belongs to the Special Issue Phytochemicals with Signaling, Medicinal and Therapeutic Properties)
188 KiB  
Article
Two New Flavones from Tridax procumbens Linn
by Runsheng Xu, Jing Zhang and Ke Yuan
Molecules 2010, 15(9), 6357-6364; https://doi.org/10.3390/molecules15096357 - 09 Sep 2010
Cited by 20 | Viewed by 9583
Abstract
Two new flavones, 8,3′-dihydroxy-3,7,4′-trimethoxy-6-O-β-D-glucopyranosyl flavone (1) and 6,8,3′-trihydroxy-3,7,4′-trimethoxyflavone (2) were isolated from Tridax procumbens Linn., together with the four known compounds puerarin (3), esculetin (4), oleanolic acid (5 [...] Read more.
Two new flavones, 8,3′-dihydroxy-3,7,4′-trimethoxy-6-O-β-D-glucopyranosyl flavone (1) and 6,8,3′-trihydroxy-3,7,4′-trimethoxyflavone (2) were isolated from Tridax procumbens Linn., together with the four known compounds puerarin (3), esculetin (4), oleanolic acid (5) and betulinic acid (6). The structures of the two new flavones were elucidated based on chemical analysis and spectral methods (IR, 1D and 2D NMR, ESI-MS, HR-ESI-MS). The antioxidant activity of the two new flavones were evaluated by two methods, the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and ferric reducing antioxidant power (FRAP) assays, and the data showed that compounds 1 and 2 have certain antioxidant activity, with the antioxidant activity of compound 2 being stronger than that of compound 1. Full article
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323 KiB  
Article
Isolation and Crystal Structure of Marcanine A from Polyalthia plagioneura
by Bingjing Liu, Lin Wang, Guangying Chen, Changri Han and Jing Wang
Molecules 2010, 15(9), 6349-6356; https://doi.org/10.3390/molecules15096349 - 09 Sep 2010
Cited by 10 | Viewed by 8139
Abstract
Marcanine A was isolated from the stems of Polyalthia plagioneura as light yellow crystals. The molecular and crystal structures have been determined by 1D,2D-NMR and X-ray diffraction analysis. It crystallizes in the triclinic system, space group P-1 with a = 5.2140(5)Å, b = [...] Read more.
Marcanine A was isolated from the stems of Polyalthia plagioneura as light yellow crystals. The molecular and crystal structures have been determined by 1D,2D-NMR and X-ray diffraction analysis. It crystallizes in the triclinic system, space group P-1 with a = 5.2140(5)Å, b = 10.1871(11)Å, c = 11.0709(13)Å, α = 110.452(2)º, β = 103.376(2)°, γ = 90.1870(10)°, V = 533.74(10)Å3, Z = 2. There are three intermolecular hydrogen bonds in a unit cell. It displays some inhibitory activities towards four kinds of human tumor cells, including BEL-7402, K562, SPCA-1and SGC-7409. Full article
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392 KiB  
Review
Transactivation of Genes Encoding for Phase II Enzymes and Phase III Transporters by Phytochemical Antioxidants
by Yoon Mee Yang, Kyoung Noh, Chang Yeob Han and Sang Geon Kim
Molecules 2010, 15(9), 6332-6348; https://doi.org/10.3390/molecules15096332 - 07 Sep 2010
Cited by 23 | Viewed by 10167
Abstract
The induction of phase II enzymes and phase III transporters contributes to the metabolism, detoxification of xenobiotics, antioxidant capacity, redox homeostasis and cell viability. Transactivation of the genes that encode for phase II enzymes and phase III transporters is coordinatively regulated by activating [...] Read more.
The induction of phase II enzymes and phase III transporters contributes to the metabolism, detoxification of xenobiotics, antioxidant capacity, redox homeostasis and cell viability. Transactivation of the genes that encode for phase II enzymes and phase III transporters is coordinatively regulated by activating transcription factors in response to external stimuli. Comprehensive studies indicate that antioxidant phytochemicals promote the induction of phase II enzymes and/or phase III transporters through various signaling pathways, including phosphoinositide 3-kinase, protein kinase C, and mitogen-activated protein kinases. This paper focuses on the molecular mechanisms and signaling pathways responsible for the transactivation of genes encoding for these proteins, as orchestrated by a series of transcription factors and related signaling components. Full article
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227 KiB  
Review
Recent Applications of Polymer Supported Organometallic Catalysts in Organic Synthesis
by Nina Kann
Molecules 2010, 15(9), 6306-6331; https://doi.org/10.3390/molecules15096306 - 07 Sep 2010
Cited by 75 | Viewed by 11274
Abstract
Recent developments concerning the application of polymer supported organometallic reagents in solid phase synthesis are reviewed, with a special focus on methodology for carbon-carbon formation. Examples of reactions that are covered include the classical Suzuki, Sonogashira and Heck coupings, but also aryl amination, [...] Read more.
Recent developments concerning the application of polymer supported organometallic reagents in solid phase synthesis are reviewed, with a special focus on methodology for carbon-carbon formation. Examples of reactions that are covered include the classical Suzuki, Sonogashira and Heck coupings, but also aryl amination, epoxide opening, rearrangements, metathesis and cyclopropanation. Applications in the field of asymmetric synthesis are also discussed. Full article
(This article belongs to the Special Issue Solid Phase Synthesis)
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1594 KiB  
Article
Content of Phenolic Compounds and Antioxidant Capacity in Fruits of Apricot Genotypes
by Jiri Sochor, Ondrej Zitka, Helena Skutkova, Dusan Pavlik, Petr Babula, Boris Krska, Ales Horna, Vojtech Adam, Ivo Provaznik and Rene Kizek
Molecules 2010, 15(9), 6285-6305; https://doi.org/10.3390/molecules15096285 - 07 Sep 2010
Cited by 100 | Viewed by 14614
Abstract
Research on natural compounds is increasingly focused on their effects on human health. In this study, we were interested in the evaluation of nutritional value expressed as content of total phenolic compounds and antioxidant capacity of new apricot (Prunus armeniaca L.) genotypes [...] Read more.
Research on natural compounds is increasingly focused on their effects on human health. In this study, we were interested in the evaluation of nutritional value expressed as content of total phenolic compounds and antioxidant capacity of new apricot (Prunus armeniaca L.) genotypes resistant against Plum pox virus (PPV) cultivated on Department of Fruit Growing of Mendel University in Brno. Fruits of twenty one apricot genotypes were collected at the onset of consumption ripeness. Antioxidant capacities of the genotypes were determined spectrometrically using DPPH• (1,1-diphenyl-2-picryl-hydrazyl free radicals) scavenging test, TEAC (Trolox Equivalent Antioxidant Capacity), and FRAP (Ferric Reducing Antioxidant Power)methods. The highest antioxidant capacities were determined in the genotypes LE-3228 and LE-2527, the lowest ones in the LE-985 and LE-994 genotypes. Moreover, close correlation (r = 0.964) was determined between the TEAC and DPPH assays. Based on the antioxidant capacity and total polyphenols content, a clump analysis dendrogram of the monitored apricot genotypes was constructed. In addition, we optimized high performance liquid chromatography coupled with tandem electrochemical and spectrometric detection and determined phenolic profile consisting of the following fifteen phenolic compounds: gallic acid, 4-aminobenzoic acid, chlorogenic acid, ferulic acid, caffeic acid, procatechin, salicylic acid, p-coumaric acid, the flavonols quercetin and quercitrin, the flavonol glycoside rutin, resveratrol, vanillin, and the isomers epicatechin, (–)- and (+)- catechin. Full article
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1373 KiB  
Review
The Structural Diversity of Deoxyribozymes
by Simon A. McManus and Yingfu Li
Molecules 2010, 15(9), 6269-6284; https://doi.org/10.3390/molecules15096269 - 06 Sep 2010
Cited by 18 | Viewed by 10691
Abstract
When not constrained to long double-helical arrangements, DNA is capable of forming structural arrangements that enable specific sequences to perform functions such as binding and catalysis under defined conditions. Through a process called in vitro selection, numerous catalytic DNAs, known as deoxyribozymes or [...] Read more.
When not constrained to long double-helical arrangements, DNA is capable of forming structural arrangements that enable specific sequences to perform functions such as binding and catalysis under defined conditions. Through a process called in vitro selection, numerous catalytic DNAs, known as deoxyribozymes or DNAzymes, have been isolated. Many of these molecules have the potential to act as therapeutic agents and diagnostic tools. As such, a better understanding of the structural arrangements present in these functional DNAs will aid further efforts in the development and optimization of these useful molecules. Structural characterization of several deoxyribozymes through mutagenesis, in vitro re-selection, chemical probing and circular dichroism has revealed many distinct and elaborate structural classes. Deoxyribozymes have been found to contain diverse structural elements including helical junctions, pseudoknots, triplexes, and guanine quadruplexes. Some of these studies have further shown the repeated isolation of similar structural motifs in independent selection experiments for the same type of chemical reaction, suggesting that some structural motifs are well suited for catalyzing a specific chemical reaction. To investigate the extent of structural diversity possible in deoxyribozymes, a group of kinase deoxyribozymes have been extensively characterized. Such studies have discovered some interesting structural features of these DNAzymes while revealing some novel DNA structures. Full article
(This article belongs to the Special Issue Catalytic Nucleic Acids)
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976 KiB  
Article
Microwave Irradiation-Assisted Synthesis of a Novel Crown Ether Crosslinked Chitosan as a Chelating Agent for Heavy Metal Ions (M+n)
by Awwad A. Radwan, Fars K. Alanazi and Ibrahim A. Alsarra
Molecules 2010, 15(9), 6257-6268; https://doi.org/10.3390/molecules15096257 - 06 Sep 2010
Cited by 33 | Viewed by 9866
Abstract
Microwave irradiation was used to obtain a di-Schiff base type crosslinked chitosan dibenzocrown ether (CCdBE) via the reaction between the –NH2 and –CHO groups in chitosan and 4,4′-diformyldibenzo-18-c-6, respectively. The structure of the synthesized compound was characterized by elemental analysis, solid state [...] Read more.
Microwave irradiation was used to obtain a di-Schiff base type crosslinked chitosan dibenzocrown ether (CCdBE) via the reaction between the –NH2 and –CHO groups in chitosan and 4,4′-diformyldibenzo-18-c-6, respectively. The structure of the synthesized compound was characterized by elemental analysis, solid state 13C-NMR and FT-IR spectra analysis. The results showed that the mass fraction of nitrogen in the CCdBE derivative was much lower than those of chitosan. The FT-IR spectra of CCdBE revealed the expected chitosan-crown ether structure, as evidenced by the presence of the characteristic C=N and Ar peaks. The adsorption properties of CCdBE for Pd2+ and Hg2+ were investigated and the results demonstrated that the adsorbent has both desirable adsorption properties with a high particular adsorption selectivity for Hg2+ when in the presence of Pb2+ as well as selectivity coefficients for metal ions of KHg2+ /Pb2+ = 8.00 and KHg 2+/Pb2+ = 10.62 at pH values of 4 and 6, respectively. The reusability tests for CCdBE for Pb2+ adsorption showed that complete recovery of the ion was possible with CCdBE after 10-multiple reuses while CTS had no reusability at acidic solution because of its higher dissolution. The studied features of CCdBE suggested that the material could be considered as a new adsorbent. It is envisaged that the crosslinking of CTS into CCdBE would enhance practicality and effectiveness of adsorption in ion separation and removal procedures. Full article
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