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

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Open AccessReview Structural and Pharmacological Effects of Ring-Closing Metathesis in Peptides
Molecules 2010, 15(9), 6638-6677; https://doi.org/10.3390/molecules15096638
Received: 2 June 2010 / Revised: 13 September 2010 / Accepted: 15 September 2010 / Published: 21 September 2010
Cited by 27 | PDF Full-text (892 KB)
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)
Open AccessArticle The Antigerminative Activity of Twenty-Seven Monoterpenes
Molecules 2010, 15(9), 6630-6637; https://doi.org/10.3390/molecules15096630
Received: 10 August 2010 / Revised: 17 September 2010 / Accepted: 19 September 2010 / Published: 21 September 2010
Cited by 60 | PDF Full-text (179 KB)
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.
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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)
Open AccessArticle Green One Pot Solvent-Free Synthesis of Pyrano[2,3-c]-Pyrazoles and Pyrazolo[1,5-a]Pyrimidines
Molecules 2010, 15(9), 6619-6629; https://doi.org/10.3390/molecules15096619
Received: 26 July 2010 / Revised: 13 August 2010 / Accepted: 26 August 2010 / Published: 20 September 2010
Cited by 44 | PDF Full-text (151 KB) | Supplementary Files
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
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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
Open AccessReview Kinin Receptor Antagonists as Potential Neuroprotective Agents in Central Nervous System Injury
Molecules 2010, 15(9), 6598-6618; https://doi.org/10.3390/molecules15096598
Received: 16 August 2010 / Revised: 10 September 2010 / Accepted: 14 September 2010 / Published: 20 September 2010
Cited by 25 | PDF Full-text (198 KB)
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
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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)
Open AccessArticle Synthesis of Chiral Macrocyclic or Linear Pyridine Carboxamides from Pyridine-2,6-dicarbonyl Dichloride as Antimicrobial Agents
Molecules 2010, 15(9), 6588-6597; https://doi.org/10.3390/molecules15096588
Received: 26 August 2010 / Revised: 6 September 2010 / Accepted: 7 September 2010 / Published: 20 September 2010
Cited by 36 | PDF Full-text (188 KB)
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
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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
Open AccessCommunication Variation of Oleanolic and Ursolic Acid in the Flesh of Persimmon Fruit among Different Cultivars
Molecules 2010, 15(9), 6580-6587; https://doi.org/10.3390/molecules15096580
Received: 5 August 2010 / Revised: 25 August 2010 / Accepted: 1 September 2010 / Published: 20 September 2010
Cited by 26 | PDF Full-text (223 KB)
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
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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)
Open AccessArticle Determination of Quercetin and Resveratrol in Whole Blood—Implications for Bioavailability Studies
Molecules 2010, 15(9), 6570-6579; https://doi.org/10.3390/molecules15096570
Received: 19 July 2010 / Revised: 27 August 2010 / Accepted: 14 September 2010 / Published: 20 September 2010
Cited by 42 | PDF Full-text (228 KB)
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
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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)
Open AccessArticle Correlation between Cytotoxic Activities and Reduction Potentials of Heterocyclic Quinones
Molecules 2010, 15(9), 6559-6569; https://doi.org/10.3390/molecules15096559
Received: 23 August 2010 / Revised: 7 September 2010 / Accepted: 16 September 2010 / Published: 20 September 2010
Cited by 11 | PDF Full-text (2862 KB)
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
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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)
Open AccessArticle New 2-Arylbenzofurans from the Root Bark of Artocarpus lakoocha
Molecules 2010, 15(9), 6548-6558; https://doi.org/10.3390/molecules15096548
Received: 29 June 2010 / Revised: 15 September 2010 / Accepted: 17 September 2010 / Published: 17 September 2010
Cited by 8 | PDF Full-text (276 KB)
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
Open AccessReview The 9-Phenyl-9-fluorenyl Group for Nitrogen Protection in Enantiospecific Synthesis
Molecules 2010, 15(9), 6512-6547; https://doi.org/10.3390/molecules15096512
Received: 12 August 2010 / Revised: 13 September 2010 / Accepted: 14 September 2010 / Published: 17 September 2010
Cited by 10 | PDF Full-text (1102 KB)
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
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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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Open AccessArticle Synthesis and Antitumor Activity of Diterpenylhydroquinone Derivatives of Natural Ent-Labdanes
Molecules 2010, 15(9), 6502-6511; https://doi.org/10.3390/molecules15096502
Received: 28 August 2010 / Revised: 8 September 2010 / Accepted: 15 September 2010 / Published: 17 September 2010
Cited by 5 | PDF Full-text (197 KB)
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
Open AccessArticle An Efficient and Chemoselective Procedure for Acylal Synthesis
Molecules 2010, 15(9), 6493-6501; https://doi.org/10.3390/molecules15096493
Received: 23 June 2010 / Revised: 6 September 2010 / Accepted: 15 September 2010 / Published: 16 September 2010
Cited by 5 | PDF Full-text (184 KB)
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
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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
Open AccessCommunication Synthesis and Antifungal Activity of Carabrone Derivatives
Molecules 2010, 15(9), 6485-6492; https://doi.org/10.3390/molecules15096485
Received: 6 July 2010 / Revised: 11 August 2010 / Accepted: 23 August 2010 / Published: 16 September 2010
Cited by 12 | PDF Full-text (269 KB)
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
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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
Open AccessCommunication Isoquinolines from the Roots of Thalictrum flavum L. and Their Evaluation as Antiparasitic Compounds
Molecules 2010, 15(9), 6476-6484; https://doi.org/10.3390/molecules15096476
Received: 15 July 2010 / Revised: 24 August 2010 / Accepted: 13 September 2010 / Published: 16 September 2010
Cited by 12 | PDF Full-text (125 KB)
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
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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)
Open AccessArticle Effects of Eupatilin and Jaceosidin on Cytochrome P450 Enzyme Activities in Human Liver Microsomes
Molecules 2010, 15(9), 6466-6475; https://doi.org/10.3390/molecules15096466
Received: 7 September 2010 / Revised: 10 September 2010 / Accepted: 14 September 2010 / Published: 16 September 2010
Cited by 20 | PDF Full-text (357 KB)
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
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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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