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Molecules, Volume 18, Issue 1 (January 2013), Pages 1-1336

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Open AccessArticle Chemical Constituents of Caesalpinia decapetala (Roth) Alston
Molecules 2013, 18(1), 1325-1336; https://doi.org/10.3390/molecules18011325
Received: 19 December 2012 / Revised: 19 December 2012 / Accepted: 20 December 2012 / Published: 22 January 2013
Cited by 36 | PDF Full-text (276 KB)
Abstract
The current study targets the chemical constituents of Caesalpinia decapetala (Roth) Alston and investigates the bioactivities of the isolated compounds. Fourteen known compounds were isolated using column chromatography, and structural identification was performed by physical and spectral analyses. The biological activities of the
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The current study targets the chemical constituents of Caesalpinia decapetala (Roth) Alston and investigates the bioactivities of the isolated compounds. Fourteen known compounds were isolated using column chromatography, and structural identification was performed by physical and spectral analyses. The biological activities of the compounds were also evaluated by 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) and 2,2-diphenlyl-1-picrylhydrazyl (DPPH) assays. Emodin (6), baicalein (9), and apigenin (12) displayed antitumor activities against the MGC-803 cell line, while quercetin (2), rutin (5), baicalein (9), and epicatechin (13) showed stronger DPPH scavenging activities compared with ascorbic acid. Andrographolide (1), quercetin (2), bergenin (4), rutin (5), emodin (6), betulin (7), baicalein (9), polydatin (10), salicin (11), and apigenin (12), were obtained from C. decapetala (Roth) Alston for the first time. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Photochemical Synthesis and Properties of 1,6- and 1,8-Naphthalenophanes
Molecules 2013, 18(1), 1314-1324; https://doi.org/10.3390/molecules18011314
Received: 20 December 2012 / Revised: 9 January 2013 / Accepted: 15 January 2013 / Published: 21 January 2013
Cited by 5 | PDF Full-text (302 KB)
Abstract
Various 1,6- and 1,8-naphthalenophanes were synthesized by using the Photo-Dehydro-Diels-Alder (PDDA) reaction of bis-ynones. These compounds are easily accessible from w-(3-iodophenyl)carboxylic acids in three steps. The obtained naphthalenophanes are axially chiral and the activation barrier for the atropisomerization could be determined in some
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Various 1,6- and 1,8-naphthalenophanes were synthesized by using the Photo-Dehydro-Diels-Alder (PDDA) reaction of bis-ynones. These compounds are easily accessible from w-(3-iodophenyl)carboxylic acids in three steps. The obtained naphthalenophanes are axially chiral and the activation barrier for the atropisomerization could be determined in some cases by means of dynamic NMR (DNMR) and/or dynamic HPLC (DHPLC) experiments. Full article
(This article belongs to the Special Issue New Trends in Photochemistry)
Open AccessReview Chemistry and Applications of Polysaccharide Solutions in Strong Electrolytes/Dipolar Aprotic Solvents: An Overview
Molecules 2013, 18(1), 1270-1313; https://doi.org/10.3390/molecules18011270
Received: 26 October 2012 / Revised: 2 January 2013 / Accepted: 9 January 2013 / Published: 21 January 2013
Cited by 21 | PDF Full-text (989 KB)
Abstract
Biopolymers and their derivatives are being actively investigated as substitutes for petroleum-based polymers. This has generated an intense interest in investigating new solvents, in particular for cellulose, chitin/chitosan, and starch. This overview focuses on recent advances in the dissolution and derivatization of these
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Biopolymers and their derivatives are being actively investigated as substitutes for petroleum-based polymers. This has generated an intense interest in investigating new solvents, in particular for cellulose, chitin/chitosan, and starch. This overview focuses on recent advances in the dissolution and derivatization of these polysaccharides in solutions of strong electrolytes in dipolar aprotic solvents. A brief description of the molecular structures of these biopolymers is given, with emphases on the properties that are relevant to derivatization, namely crystallinity and accessibility. The mechanism of cellulose dissolution is then discussed, followed by a description of the strategies employed for the synthesis of cellulose derivatives (carboxylic acid esters, and ethers) under homogeneous reaction conditions. The same sequence of presentation has been followed for chitin/chitosan and starch. Future perspectives for this subject are summarized, in particular with regard to compliance with the principles of green chemistry. Full article
(This article belongs to the Special Issue Advances in Carbohydrate Chemistry 2012)
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Open AccessArticle A New Triterpenoid from Teucrium viscidum
Molecules 2013, 18(1), 1262-1269; https://doi.org/10.3390/molecules18011262
Received: 3 December 2012 / Revised: 1 January 2013 / Accepted: 7 January 2013 / Published: 21 January 2013
Cited by 10 | PDF Full-text (280 KB) | Supplementary Files
Abstract
A new ursane-type triterpenoid, 3β-hydroxy-urs-30-p-Z-hydroxycinnamoyloxy-12-en-28-oic-acid (1), together with three known triterpenoids, 3β-hydroxy-urs-30-p-E-hydroxycinnamoyloxy-12-en-28-oic-acid (2), 2α,3β,19α-trihydroxy-urs-12-en-28-oic-acid (3), and ursolic acid (
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A new ursane-type triterpenoid, 3β-hydroxy-urs-30-p-Z-hydroxycinnamoyloxy-12-en-28-oic-acid (1), together with three known triterpenoids, 3β-hydroxy-urs-30-p-E-hydroxycinnamoyloxy-12-en-28-oic-acid (2), 2α,3β,19α-trihydroxy-urs-12-en-28-oic-acid (3), and ursolic acid (4), four known lignans, pinoresinol (5), 9α-hydroxypinoresinol (6), (+)-medioresinol (7), and (+)-kobusin (8), and two steroids, β-sitosterol (9), and daucosterol (10), were isolated from the whole parts of Teucrium viscidum. Their structures were established by a combination of spectroscopic data analysis, besides comparison with literature data. Compounds 14 were evaluated for their inhibitory activities against 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1). Full article
(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)
Open AccessArticle A New Phenolic Glycoside from Chamaecyparis obtusa var. breviramea f. crippsii
Molecules 2013, 18(1), 1255-1261; https://doi.org/10.3390/molecules18011255
Received: 19 November 2012 / Revised: 7 December 2012 / Accepted: 26 December 2012 / Published: 18 January 2013
Cited by 8 | PDF Full-text (235 KB)
Abstract
A new phenolic glycoside, 3-methoxyphenol 1-O-α-L-rhamnopyranosyl-(1→6)- O-β-D-glucopyranoside (1), was isolated from the 90% acetone extract of the branches and leaves of Chamaecyparis obtusa var. breviramea f. crippsii along with another 10 known phenolics 2
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A new phenolic glycoside, 3-methoxyphenol 1-O-α-L-rhamnopyranosyl-(1→6)- O-β-D-glucopyranoside (1), was isolated from the 90% acetone extract of the branches and leaves of Chamaecyparis obtusa var. breviramea f. crippsii along with another 10 known phenolics 211. Their structures were determined mainly by means of MS, 1D- and 2D-NMR data. Cytotoxicities of compounds 3 and 511 were tested on BGC-823, Hela and A549 cancer cell lines, the results showed that compound 8 was bioactive and its IC50 values were 6.9, 29.7 and 52.9 μM, respectively. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessReview A Review on Anti-Inflammatory Activity of Monoterpenes
Molecules 2013, 18(1), 1227-1254; https://doi.org/10.3390/molecules18011227
Received: 22 December 2012 / Revised: 4 January 2013 / Accepted: 5 January 2013 / Published: 18 January 2013
Cited by 103 | PDF Full-text (266 KB) | Supplementary Files
Abstract
Faced with the need to find new anti-inflammatory agents, great effort has been expended on the development of drugs for the treatment of inflammation. This disorder reduces the quality of life and overall average productivity, causing huge financial losses. In this review the
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Faced with the need to find new anti-inflammatory agents, great effort has been expended on the development of drugs for the treatment of inflammation. This disorder reduces the quality of life and overall average productivity, causing huge financial losses. In this review the anti-inflammatory activity of 32 bioactive monoterpenes found in essential oils is discussed. The data demonstrate the pharmacological potential of this group of natural chemicals to act as anti-inflammatory drugs. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Protective Effect of Ginsenoside Rb1 Against Lung Injury Induced by Intestinal Ischemia-Reperfusion in Rats
Molecules 2013, 18(1), 1214-1226; https://doi.org/10.3390/molecules18011214
Received: 13 December 2012 / Revised: 5 January 2013 / Accepted: 11 January 2013 / Published: 17 January 2013
Cited by 20 | PDF Full-text (988 KB)
Abstract
Intestinal ischemia-reperfusion (I/R) is a critical event in the pathogenesis of multiple organ dysfunction syndromes (MODS). The lungs are some of the most vulnerable organs that are impacted by intestinal I/R. The aim of this study is to investigate whether ginsenoside Rb1 can
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Intestinal ischemia-reperfusion (I/R) is a critical event in the pathogenesis of multiple organ dysfunction syndromes (MODS). The lungs are some of the most vulnerable organs that are impacted by intestinal I/R. The aim of this study is to investigate whether ginsenoside Rb1 can ameliorate remote lung injury induced by intestinal I/R. Adult male Wistar rats were randomly divided into four groups: (1) a control, sham-operated group (sham group); (2) an intestinal I/R group subjected to 1 h intestinal ischemia and 2 h reperfusion (I/R group); (3) a group treated with 20 mg/kg ginsenoside Rb1 before reperfusion (Rb1-20 group); and (4) a group treated with 40 mg/kg ginsenoside Rb1 before reperfusion (Rb1-40 group). Intestinal and lung histology was observed. The malondialdehyde (MDA) levels in intestinal tissues were measured. Myeloperoxidase (MPO), TNF-α, MDA levels, wet/dry weight ratio and immunohistochemical expression of intracellular adhesion molecule-1 (ICAM-1) in lung tissues were assayed. In addition, a western blot of lung NF-kB was performed. Results indicated that intestinal I/R induced intestinal and lung injury, which was characterized by increase of MDA levels and pathological scores in intestinal tissues and MPO, TNF-α , MDA levels, wet/dry weight ratio and ICAM-1, NF-kB expression in the lung tissues. Ginsenoside Rb1 (20, 40 mg/kg) ameliorated intestinal and lung injury, decreased MPO, TNF-α, MDA levels, wet/dry weight ratio, ICAM-1 and NF-kB expression in lung tissues. In conclusion, ginsenoside Rb1 ameliorated the lung injuries by decreasing the NF-kB activation-induced inflammatory response. Full article
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Open AccessReview Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments
Molecules 2013, 18(1), 1188-1213; https://doi.org/10.3390/molecules18011188
Received: 19 December 2012 / Revised: 8 January 2013 / Accepted: 9 January 2013 / Published: 17 January 2013
Cited by 68 | PDF Full-text (472 KB)
Abstract
Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM) cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so
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Since the first report and due to its handiness and wide scope, the Suzuki-Miyaura (SM) cross coupling reaction has become a routine methodology in many laboratories worldwide. With respect to other common transition metal catalyzed cross couplings, the SM reaction has been so far less exploited as a tool to introduce an acyl function into a specific substrate. In this review, the various approaches found in the literature will be considered, starting from the direct SM acylative coupling to the recent developments of cross coupling between boronates and acyl chlorides or anhydrides. Special attention will be dedicated to the use of masked acyl boronates, alkoxy styryl and alkoxy dienyl boronates as coupling partners. A final section will be then focused on the acyl SM reaction as key synthetic step in the framework of natural products synthesis. Full article
(This article belongs to the Special Issue Suzuki Reaction)
Open AccessArticle Two Cerebrosides Isolated from the Seeds of Sterculia lychnophora and Their Neuroprotective Effect
Molecules 2013, 18(1), 1181-1187; https://doi.org/10.3390/molecules18011181
Received: 22 November 2012 / Revised: 25 December 2012 / Accepted: 8 January 2013 / Published: 17 January 2013
Cited by 8 | PDF Full-text (220 KB)
Abstract
Two cerebrosides named 1-O-b-D-glucopyranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyoctadecanoyl)amido]-4,8-octadecadiene-1,3-diol (1) and soya-cerebroside I (2) were isolated from the seeds of Sterculia lychnophora for the first time. Their structures were completely characterized by
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Two cerebrosides named 1-O-b-D-glucopyranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxyoctadecanoyl)amido]-4,8-octadecadiene-1,3-diol (1) and soya-cerebroside I (2) were isolated from the seeds of Sterculia lychnophora for the first time. Their structures were completely characterized by spectroscopic methods including IR, MS and NMR. Compound 1 exhibited moderate neuroprotective effect against SH-SY5Y cell damage induced by hydrogen peroxide. Full article
(This article belongs to the Section Natural Products Chemistry)
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Open AccessArticle Diastereoselective Synthesis of 5-Hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one
Molecules 2013, 18(1), 1174-1180; https://doi.org/10.3390/molecules18011174
Received: 13 December 2012 / Revised: 10 January 2013 / Accepted: 14 January 2013 / Published: 17 January 2013
PDF Full-text (262 KB)
Abstract
A short five steps synthesis of the title compound from vanillin is described. The racemic spiroether 7 was obtained in 61% yield and in >99% diastereomeric excess (by 1H-NMR) from the corresponding phenolic derivative 3 by oxidation with lead (IV) acetate. Full article
Open AccessArticle A Facile Synthesis of Fully Protected meso-Diaminopimelic Acid (DAP) and Its Application to the Preparation of Lipophilic N-Acyl iE-DAP
Molecules 2013, 18(1), 1162-1173; https://doi.org/10.3390/molecules18011162
Received: 5 December 2012 / Revised: 8 January 2013 / Accepted: 9 January 2013 / Published: 16 January 2013
Cited by 7 | PDF Full-text (269 KB)
Abstract
Synthesis of beneficial protected meso-DAP 9 by cross metathesis of the Garner aldehyde-derived vinyl glycine 1b with protected allyl glycine 2 in the presence of Grubbs second-generation catalyst was performed. Preparation of lipophilic N-acyl iE-DAP as potent agonists of NOD 1-mediated
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Synthesis of beneficial protected meso-DAP 9 by cross metathesis of the Garner aldehyde-derived vinyl glycine 1b with protected allyl glycine 2 in the presence of Grubbs second-generation catalyst was performed. Preparation of lipophilic N-acyl iE-DAP as potent agonists of NOD 1-mediated immune response from 9 is described. Full article
(This article belongs to the Special Issue Chemical Protein and Peptide Synthesis)
Open AccessArticle Bioassay-Guided Isolation of DPP-4 Inhibitory Fractions from Extracts of Submerged Cultured of Inonotus obliquus
Molecules 2013, 18(1), 1150-1161; https://doi.org/10.3390/molecules18011150
Received: 21 November 2012 / Revised: 7 December 2012 / Accepted: 14 January 2013 / Published: 16 January 2013
Cited by 14 | PDF Full-text (280 KB)
Abstract
Inonotus obliquus is a medicinal mushroom used in Russian and Eastern European folk medicine for the treatment of gastrointestinal cancer, cardiovascular disease and diabetes. Previous studies in our laboratory have demonstrated that the mycelium powders of I. obliquus possess significant antihyperglycemic effects in
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Inonotus obliquus is a medicinal mushroom used in Russian and Eastern European folk medicine for the treatment of gastrointestinal cancer, cardiovascular disease and diabetes. Previous studies in our laboratory have demonstrated that the mycelium powders of I. obliquus possess significant antihyperglycemic effects in a mouse model of diabetic disease induced by alloxan. However, the active ingredients of mycelium powders responsible for the diabetes activity have not been identified. This study aims to identify the active ingredients of I. obliquus mycelium powders by a bioassay-guided fractionation approach and explore the mechanism of action of these active ingredients by using a well-established DPP-4 (an important enzyme as a new therapeutic target for diabetes) inhibitory assay model. The results showed the chloroform extract of mycelium was potential inhibitory against DPP-4. Bioactivity guided fractionation led to the identification of 19 compounds using UPLC-Q-TOF-MS. Molecular docking between the compounds and DPP-4 revealed that compounds 5, 8, 9, 14, 15 may be the active components responsible for the DPP-4 inhibitory activity. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Improvement of the Enzyme Performance of Trypsin via Adsorption in Mesoporous Silica SBA-15: Hydrolysis of BAPNA
Molecules 2013, 18(1), 1138-1149; https://doi.org/10.3390/molecules18011138
Received: 3 December 2012 / Revised: 9 January 2013 / Accepted: 10 January 2013 / Published: 16 January 2013
Cited by 9 | PDF Full-text (470 KB)
Abstract
The enzymatic performance of trypsin in hydrolysis of N-α-benzoyl-DL-arginine-4-nitroanilide (BAPNA) was improved by adsorption on Santa Barbara Amorphous (SBA)-15 mesoporous silica. The optimal immobilization conditions were screened and the properties of immobilized enzyme have also been studied. Under the optimal conditions, the
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The enzymatic performance of trypsin in hydrolysis of N-α-benzoyl-DL-arginine-4-nitroanilide (BAPNA) was improved by adsorption on Santa Barbara Amorphous (SBA)-15 mesoporous silica. The optimal immobilization conditions were screened and the properties of immobilized enzyme have also been studied. Under the optimal conditions, the immobilized trypsin displays maximum specific activity (49.8 μmol/min/g). The results also indicate that the immobilized trypsin exhibits better storage stability. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Antioxidant and Antimicrobial Activities of 7-Hydroxy-calamenene-Rich Essential Oils from Croton cajucara Benth.
Molecules 2013, 18(1), 1128-1137; https://doi.org/10.3390/molecules18011128
Received: 29 November 2012 / Revised: 4 January 2013 / Accepted: 11 January 2013 / Published: 16 January 2013
Cited by 11 | PDF Full-text (199 KB)
Abstract
Croton cajucara is a shrub native to the Amazon region locally known as “sacaca”. Two morphotypes are known: white and red “sacaca”. The essential oils (EO) obtained by hydrodistillation from leaves of the red morphotype were, in general, rich in 7-hydroxycalamenene (28.4%–37.5%). The
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Croton cajucara is a shrub native to the Amazon region locally known as “sacaca”. Two morphotypes are known: white and red “sacaca”. The essential oils (EO) obtained by hydrodistillation from leaves of the red morphotype were, in general, rich in 7-hydroxycalamenene (28.4%–37.5%). The effectiveness of these EO regarding the antimicrobial activity against pathogenic microorganisms was initially investigated by the drop test method, showing significant inhibition zones. Among the microorganisms tested, the essential oils rich in 7-hydroxycalamenene were more effective against methicillin resistant Staphylococcus aureus (MRSA), Enterococcus faecalis, Mycobacterium tuberculosis, M. smegmatis, Mucor circinelloides and Rhizopus oryzae. The minimum inhibitory concentrations (MIC) of the oils were determined using the broth dilution assay. It was possible to observe that 7-hydroxycalamenene-rich oils presented high antimicrobial activity, with MIC of 4.76 × 10−3 μg/mL for MRSA, 4.88 μg/mL for M. tuberculosis, 39.06 μg/mL for M. smegmatis, and 0.152 μg/mL for R. oryzae and 3.63 × 10−8 μg/mL for M. circinelloides. The antioxidant activity of this EO suggests that 7-hydroxycalamenene provides more antioxidant activity according with EC50 less than 63.59 μg/mL. Considering the bioactive potential of EOs and 7-hydroxycalamenene could be of great interest for development of antimicrobials for therapeutic use in treatment of bacterial and fungal infections in humans and/or veterinary practice. Full article
(This article belongs to the Special Issue Antioxidants 2012)
Open AccessCommunication Ligand Binding Affinities of Arctigenin and Its Demethylated Metabolites to Estrogen Receptor Alpha
Molecules 2013, 18(1), 1122-1127; https://doi.org/10.3390/molecules18011122
Received: 8 October 2012 / Revised: 10 January 2013 / Accepted: 14 January 2013 / Published: 16 January 2013
Cited by 9 | PDF Full-text (165 KB)
Abstract
Phytoestrogens are defined as plant-derived compounds with estrogen-like activities according to their chemical structures and activities. Plant lignans are generally categorized as phytoestrogens. It was reported that (−)-arctigenin, the aglycone of arctiin, was demethylated to (−)-dihydroxyenterolactone (DHENL) by Eubacterium (E.) sp. ARC-2. Through
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Phytoestrogens are defined as plant-derived compounds with estrogen-like activities according to their chemical structures and activities. Plant lignans are generally categorized as phytoestrogens. It was reported that (−)-arctigenin, the aglycone of arctiin, was demethylated to (−)-dihydroxyenterolactone (DHENL) by Eubacterium (E.) sp. ARC-2. Through stepwise demethylation, E. sp. ARC-2 produced six intermediates, three mono-desmethylarctigenins and three di-desmethylarctigenins. In the present study, ligand binding affinities of (−)-arctigenin and its seven metabolites, including DHENL, were investigated for an estrogen receptor alpha, and found that demethylated metabolites had stronger binding affinities than (−)-arctigenin using a ligand binding screen assay method. The IC50 value of (2R,3R)-2-(4-hydroxy-3-methoxybenzyl)-3-(3,4-dihydroxybenzyl)-butyrolactone was 7.9 × 10−4 M. Full article
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