Molecules

384 KiB

Open AccessArticle

Release of Terpenes from Fir Wood during Its Long-Term Use and in Thermal Treatment

by František Kačík, Veronika Veľková, Pavel Šmíra, Andrea Nasswettrová, Danica Kačíková and Ladislav Reinprecht

Molecules 2012, 17(8), 9990-9999; https://doi.org/10.3390/molecules17089990 - 21 Aug 2012

Cited by 35 | Viewed by 7234

Abstract

Building structures made from fir wood are often attacked by wood-destroying insects for which the terpenes it contains serve as attractants. One of the possibilities for extending the lifetime of structures is to use older wood with a lower content of terpenes and/or [...] Read more.

Building structures made from fir wood are often attacked by wood-destroying insects for which the terpenes it contains serve as attractants. One of the possibilities for extending the lifetime of structures is to use older wood with a lower content of terpenes and/or thermally modified wood. The study evaluated the levels of terpenes in naturally aged fir wood (108, 146, 279, 287 and 390 years) and their decrease by thermal treatment (the temperature of 60 °C and 120 °C, treatment duration of 10 h). Terpenes were extracted from wood samples by hexane and analyzed by gas-chromatography mass-spectrometry (GC-MS). The results indicate that recent fir wood contained approximately 60 times more terpenes than the oldest wood (186:3.1 mg/kg). The thermal wood treatment speeded up the release of terpenes. The temperature of 60 °C caused a loss in terpenes in the recent fir wood by 62%, the temperature of 120 °C even by >99%. After the treatment at the temperature of 60 °C the recent fir wood had approximately the same quantity of terpenes as non-thermally treated 108 year old wood, i.e., approximately 60–70 mg/kg. After the thermal treatment at the temperature of 120 °C the quantity of terpenes dropped in the recent as well as the old fir wood to minimum quantities (0.7–1.1 mg/kg). The thermal treatment can thus be used as a suitable method for the protection of fir wood from wood-destroying insects. Full article

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803 KiB

Open AccessArticle

BCL::EMAS — Enantioselective Molecular Asymmetry Descriptor for 3D-QSAR

by Gregory Sliwoski, Edward W. Lowe, Jr., Mariusz Butkiewicz and Jens Meiler

Molecules 2012, 17(8), 9971-9989; https://doi.org/10.3390/molecules17089971 - 20 Aug 2012

Cited by 7 | Viewed by 7185

Abstract

Stereochemistry is an important determinant of a molecule’s biological activity. Stereoisomers can have different degrees of efficacy or even opposing effects when interacting with a target protein. Stereochemistry is a molecular property difficult to represent in 2D-QSAR as it is an inherently three-dimensional [...] Read more.

Stereochemistry is an important determinant of a molecule’s biological activity. Stereoisomers can have different degrees of efficacy or even opposing effects when interacting with a target protein. Stereochemistry is a molecular property difficult to represent in 2D-QSAR as it is an inherently three-dimensional phenomenon. A major drawback of most proposed descriptors for 3D-QSAR that encode stereochemistry is that they require a heuristic for defining all stereocenters and rank-ordering its substituents. Here we propose a novel 3D-QSAR descriptor termed Enantioselective Molecular ASymmetry (EMAS) that is capable of distinguishing between enantiomers in the absence of such heuristics. The descriptor aims to measure the deviation from an overall symmetric shape of the molecule. A radial-distribution function (RDF) determines a signed volume of tetrahedrons of all triplets of atoms and the molecule center. The descriptor can be enriched with atom-centric properties such as partial charge. This descriptor showed good predictability when tested with a dataset of thirty-one steroids commonly used to benchmark stereochemistry descriptors (r² = 0.89, q² = 0.78). Additionally, EMAS improved enrichment of 4.38 versus 3.94 without EMAS in a simulated virtual high-throughput screening (vHTS) for inhibitors and substrates of cytochrome P450 (PUBCHEM AID891). Full article

(This article belongs to the Special Issue QSAR and Its Applications)

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216 KiB

Open AccessArticle

Design and Synthesis of a Series of Pyrido[2,3-d]pyrimidine Derivatives as CCR4 Antagonists

by Hongwei Gong, Hui Qi, Wei Sun, Yang Zhang, Dan Jiang, Junhai Xiao, Xiaohong Yang, Ying Wang and Song Li

Molecules 2012, 17(8), 9961-9970; https://doi.org/10.3390/molecules17089961 - 20 Aug 2012

Cited by 21 | Viewed by 7505

Abstract

A series of pyrido[2,3-d]pyrimidine derivatives were designed and synthesized based on known CC chemokine receptor 4 (CCR4) antagonists. The activities of all the newly synthesized compounds were evaluated using a chemotaxis inhibition assay. Compound 6b was proven to be a potent CCR4 antagonist [...] Read more.

A series of pyrido[2,3-d]pyrimidine derivatives were designed and synthesized based on known CC chemokine receptor 4 (CCR4) antagonists. The activities of all the newly synthesized compounds were evaluated using a chemotaxis inhibition assay. Compound 6b was proven to be a potent CCR4 antagonist that can block cell chemotaxis induced by macrophage-derived chemokine (MDC), thymus and activation regulated chemokine (TARC), and CKLF1, the natural ligands of CCR4. In addition, compound 6b is more effective than budesonide in the murine rhinitis model. The intravenous injection LD₅₀ of compound 6b is 175 mg/kg and the oral LD₅₀ is greater than 2,000 mg/kg. Full article

(This article belongs to the Section Medicinal Chemistry)

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497 KiB

Open AccessArticle

Laminarin Induces Apoptosis of Human Colon Cancer LOVO Cells through a Mitochondrial Pathway

by Yu Bin Ji, Chen Feng Ji and He Zhang

Molecules 2012, 17(8), 9947-9960; https://doi.org/10.3390/molecules17089947 - 20 Aug 2012

Cited by 49 | Viewed by 5994

Abstract

Many scientific studies have shown that laminarin has anti-tumor effects, but the anti-tumor mechanism was unclear. The purpose of this study was to investigate the effect of laminarin on the induction of apoptosis in human colon cancer LOVO cells and the molecular mechanism [...] Read more.

Many scientific studies have shown that laminarin has anti-tumor effects, but the anti-tumor mechanism was unclear. The purpose of this study was to investigate the effect of laminarin on the induction of apoptosis in human colon cancer LOVO cells and the molecular mechanism involved. LOVO cells were treated with different concentrations of laminarin at different times. Morphology observations were performed to determine the effects of laminarin on apoptosis of LOVO cells. Flow cytometry (FCM) was used to detect the level of intracellular reactive oxygen species (ROS) and pH. Laser scanning confocal microscope (LSCM) was used to analyze intracellular calcium ion concentration, mitochondrion permeability transition pore (MPTP) and mitochondrial membrane potential (MMP). Western blotd were performed to analyze the expressions of Cyt-C, Caspase-9 and -3. The results showed the apoptosis morphology, which showed cell protuberance, concentrated cytoplasm and apoptotic bodies, was obvious after 72 h treatment. Laminarin treatment for 24 h increased the intracellular level of ROS and Ca²⁺; decreased pH value; activated intracellular MPTP and decreased MMP in dose-dependent manners. It also induced the release of Cyt-C and the activation of Caspase-9 and -3. In conclusion, laminarin induces LOVO cell apoptosis through a mitochondrial pathway, suggesting that it could be a potent agent for cancer prevention and treatment. Full article

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220 KiB

Open AccessArticle

Alkaloids Isolated from the Lateral Root of Aconitum carmichaelii

by Liang Xiong, Cheng Peng, Xiao-Fang Xie, Li Guo, Cheng-Jun He, Zhao Geng, Feng Wan, Ou Dai and Qin-Mei Zhou

Molecules 2012, 17(8), 9939-9946; https://doi.org/10.3390/molecules17089939 - 20 Aug 2012

Cited by 64 | Viewed by 9267

Abstract

Two new alkaloids, aconicarmine (1) and aconicaramide (5), were isolated from the EtOH extract of the lateral roots of Aconitum carmichaelii, together with five known compounds: fuziline (2), neoline (3), N-ethylhokbusine B ( [...] Read more.

Two new alkaloids, aconicarmine (1) and aconicaramide (5), were isolated from the EtOH extract of the lateral roots of Aconitum carmichaelii, together with five known compounds: fuziline (2), neoline (3), N-ethylhokbusine B (4), 5-hydroxymethylpyrrole-2-carbaldehyde (6), and oleracein E (7). Their structures were elucidated by physical and NMR analysis. Pyrrole alkaloids were isolated from A. carmichaelii for the first time. In the in vitro assays, compounds 2 and 3 showed activity against pentobarbital sodium-induced cardiomyocytes damage by obviously recovering beating rhythm and increasing the cell viability, while compounds 5 and 7 showed moderate antibacterial activity. Full article

(This article belongs to the Section Natural Products Chemistry)

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693 KiB

Open AccessArticle

The Bioassay-Guided Isolation of Growth Inhibitors of Adult T-Cell Leukemia (ATL), from the Jamaican Plant Hyptis verticillata, and NMR Characterization of Hyptoside

by Toshiyuki Hamada, Yohann White, Mitsuyoshi Nakashima, Yusuke Oiso, Masaki J. Fujita, Hiroaki Okamura, Tetsuo Iwagawa and Naomichi Arima

Molecules 2012, 17(8), 9931-9938; https://doi.org/10.3390/molecules17089931 - 17 Aug 2012

Cited by 16 | Viewed by 6747

Abstract

Through bioassay-guided isolation, five compounds with growth inhibitory activity on S1T, an adult T-cell leukemia (ATL) cell line, were isolated from the crude methanol extract of the aerial parts of Hyptis verticillata. Full article

(This article belongs to the Section Natural Products Chemistry)

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416 KiB

Open AccessArticle

Anti-metastatic Semi-synthetic Sulfated Maltotriose C-C Linked Dimers. Synthesis and Characterisation

by Elena Vismara, Alessia Coletti, Antonio Valerio, Annamaria Naggi, Elena Urso and Giangiacomo Torri

Molecules 2012, 17(8), 9912-9930; https://doi.org/10.3390/molecules17089912 - 17 Aug 2012

Cited by 8 | Viewed by 6514

Abstract

This manuscript describes the preparation and the spectroscopic characterisation of semi-synthetic sulfated maltotriose C-C linked dimers (SMTCs) where the natural C-O-C anomeric bond was substituted by one direct central C-C bond. This C-C bond induces conformation and flexibility changes with respect to the [...] Read more.

This manuscript describes the preparation and the spectroscopic characterisation of semi-synthetic sulfated maltotriose C-C linked dimers (SMTCs) where the natural C-O-C anomeric bond was substituted by one direct central C-C bond. This C-C bond induces conformation and flexibility changes with respect to the usual anomeric bond. SMTCs neutral precursors came from maltotriosyl bromide electroreduction through maltotriosyl radical intermediate dimerisation. The new C-C bond configuration, named for convenience a,a, a,b and b,b as the natural anomeric bond, dictated the statistic ratio formation of three diastereoisomers. They were separated by silica gel flash chromatography followed by semi preparative HPLC chromatography. Each diastereoisomer was exhaustively sulfated to afford the corresponding SMTCs. SMTCs were huge characterised by NMR spectroscopy which provided the sulfation degree, too. a,a and a,b were found quite homogeneous samples with a high degree of sulfation (85–95%). b,b appeared a non-homogeneous sample whose average sulfation degree was evaluated at around 78%. Mass spectroscopy experiments confirmed the sulfation degree range. Some considerations were proposed about SMTCs structure-biological properties. Full article

(This article belongs to the Special Issue Advances in Carbohydrate Chemistry 2012)

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474 KiB

Open AccessArticle

Formation of Aldehyde and Ketone Compounds during Production and Storage of Milk Powder

by Yanhua Li, Lanwei Zhang and Weijun Wang

Molecules 2012, 17(8), 9900-9911; https://doi.org/10.3390/molecules17089900 - 17 Aug 2012

Cited by 51 | Viewed by 7909

Abstract

Certain aldehyde and ketone compounds can be used as indicators, at a molecular level, of the oxidized flavor of milk powder instead of sensory evaluation. This study investigated the formation of aldehyde and ketone compounds as affected by the heat-related processing and storage [...] Read more.

Certain aldehyde and ketone compounds can be used as indicators, at a molecular level, of the oxidized flavor of milk powder instead of sensory evaluation. This study investigated the formation of aldehyde and ketone compounds as affected by the heat-related processing and storage of milk powder. The compounds were extracted by solid phase microextraction fiber and determined using gas chromatography-mass spectrometry. In the results, higher contents of hexanal, 2-heptanone, octanal and 3-octen-2-one were detected in concentrated milk and fresh milk powders than in raw milk and heated milk. The levels of these compounds increased with increasing time of storage of milk powder. Meanwhile, the DPPH radical scavenging activity decreased and peroxide value increased during the production and storage of milk powder. In addition, the pore volume distribution of milk powder particle was determined by nitrogen isotherm adsorption. The porosity of milk powder was significantly correlated to the changes of aldehyde and ketone compounds during storages periods of 3 months (r > 0.689, p < 0.05) and 6 months (r > 0.806, p < 0.01). Therefore attention should be paid to the detectable aldehyde and ketone molecules to control the oxidized flavor, which was influenced by pre-heating as well as concentration and drying during milk powder production. Full article

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324 KiB

Open AccessArticle

Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles

by Natarajan Arumugam, Aisyah Saad Abdul Rahim, Shafida Abd Hamid and Hasnah Osman

Molecules 2012, 17(8), 9887-9899; https://doi.org/10.3390/molecules17089887 - 17 Aug 2012

Cited by 8 | Viewed by 7264

Abstract

A series of novel 1-(2′-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles has been prepared via one-pot glycosylation of ethyl-1-(2'-hydroxyethyl)-2-arylbenzimidazole-5-carboxylate derivatives. Synthesis of the 2-arylbenzimidazole aglycones from 4-fluoro-3-nitrobenzoic acid was accomplished in four high-yielding steps. The reduction and cyclocondensation steps for the aglycone synthesis proceeded efficiently [...] Read more.

A series of novel 1-(2′-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles has been prepared via one-pot glycosylation of ethyl-1-(2'-hydroxyethyl)-2-arylbenzimidazole-5-carboxylate derivatives. Synthesis of the 2-arylbenzimidazole aglycones from 4-fluoro-3-nitrobenzoic acid was accomplished in four high-yielding steps. The reduction and cyclocondensation steps for the aglycone synthesis proceeded efficiently under microwave irradiation to afford the appropriate benzimidazoles in excellent yields within 2–3 min. Glycosylation of the hydroxyethyl aglycones with the perbenzylated 1-hydroxy- glucopyranose, pretreated with the Appel-Lee reagent, followed by catalytic hydrogenolysis delivered the desired 1-(2′-α-O-D-glucopyranosyl ethyl) 2-aryl-benzimidazoles in a simple and straightforward manner. Full article

(This article belongs to the Section Organic Chemistry)

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431 KiB

Open AccessArticle

Synthesis and Bioactivity Evaluation of New 6-Aryl-5-cyano Thiouracils as Potential Antimicrobial and Anticancer Agents

by Azza Taher Taher and Sahar Mahmoud Abou-Seri

Molecules 2012, 17(8), 9868-9886; https://doi.org/10.3390/molecules17089868 - 17 Aug 2012

Cited by 38 | Viewed by 10148

Abstract

Several novel 6-aryl-5-cyano thiouracil derivatives were synthesized and explored for their activities as antibacterial, antifungal and anticancer agents. The antimicrobial evaluation revealed that compounds 7b and 7c possessed superior antibacterial activity against the Gram positive bacteria S. aureus and B. subtilis compared to [...] Read more.

Several novel 6-aryl-5-cyano thiouracil derivatives were synthesized and explored for their activities as antibacterial, antifungal and anticancer agents. The antimicrobial evaluation revealed that compounds 7b and 7c possessed superior antibacterial activity against the Gram positive bacteria S. aureus and B. subtilis compared to the reference drug amoxicillin. Moreover, compound 4i was found to be a broad spectrum antimicrobial agent and it also exhibited the highest antifungal activity against C. albicans, even higher than the reference drug amphotericin B (MIC = 2.34, 3.00 μg/mL respectively). Selected compounds were tested for in vitro cytotoxicity at a single 10⁻⁵ M concentration in accordance to the NCI (USA) protocol. The preliminary screening results showed that most of the compounds had limited cytotoxic activity against renal cancer UO-31 and/or A498 cell lines. Nevertheless, compounds 6d and 6i displayed potent growth inhibitory effect toward non-small cell lung cancer HOP-92 and leukemia MOLT-4 cell lines, respectively. Full article

(This article belongs to the Section Medicinal Chemistry)

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385 KiB

Open AccessArticle

The Active Ingredients of Jiang-Zhi-Ning: Study of the Nelumbo nucifera Alkaloids and Their Main Bioactive Metabolites

by Jianxin Chen, Xueling Ma, Kuo Gao, Yong Wang, Huihui Zhao, Hao Wu, Juan Wang, Hua Xie, Yulin OuYang, Liangtao Luo, Shuzhen Guo, Jing Han, Bing Liu and Wei Wang

Molecules 2012, 17(8), 9855-9867; https://doi.org/10.3390/molecules17089855 - 16 Aug 2012

Cited by 15 | Viewed by 8501

Abstract

The object of this study was to identify the major active ingredients of the Chinese Traditional Medicine Jiang-Zhi-Ning (JZN) based on the high performance liquid chromatography (HPLC) profiles of plasma samples obtained from beagle dogs at different times after intragastric administration of JZN, [...] Read more.

The object of this study was to identify the major active ingredients of the Chinese Traditional Medicine Jiang-Zhi-Ning (JZN) based on the high performance liquid chromatography (HPLC) profiles of plasma samples obtained from beagle dogs at different times after intragastric administration of JZN, crude JZN extracts, different extracted fractions, different subfractions of the active fraction and different isolated ingredients. 2-Hydroxy-1-methoxyaporphin (2H1M), an alkaloid from Nelumbo nucifera, one of the herbs that make up JZN, was identified as the constituent showing the major pharmacodynamic effect. The major metabolites of 2H1M were analyzed and identified as N-demethyl-2-hydroxy-1-methoxyaporphine-2-O-glycuronic acid, 2-hydroxy-1-methoxy-aporphine-2-O-glycuronic acid and 2-hydroxy-1-methoxy-aporphine-2-O-sulphate. This study provided a comprehensive insight into the active components of JZN. Full article

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350 KiB

Open AccessReview

Bioprospecting of Marine Invertebrates for New Natural Products — A Chemical and Zoogeographical Perspective

by Miguel Costa Leal, Carolina Madeira, Cláudio Alexandre Brandão, João Puga and Ricardo Calado

Molecules 2012, 17(8), 9842-9854; https://doi.org/10.3390/molecules17089842 - 16 Aug 2012

Cited by 59 | Viewed by 11014

Abstract

Bioprospecting for new marine natural products (NPs) has increased significantly over the last decades, leading to an unprecedented discovery of new molecules. Marine invertebrates have been the most important source of these NPs, with researchers commonly targeting particular taxonomic groups, marine regions and/or [...] Read more.

Bioprospecting for new marine natural products (NPs) has increased significantly over the last decades, leading to an unprecedented discovery of new molecules. Marine invertebrates have been the most important source of these NPs, with researchers commonly targeting particular taxonomic groups, marine regions and/or molecules from specific chemical groups. The present review focuses on new NPs identified from marine invertebrates between 2000 and 2009, and performs a detailed analysis on: (1) the chemical groups of these NPs; (2) the association of particular chemical groups to specific marine invertebrate taxa; and (3) the yielding of molecules from the same chemical group from organisms occurring in a particular geographic region. Our survey revealed an increasing number of new terpenoids being discovered between 2000 and 2009, contrasting with the decreasing trend in the discovery of new alkaloids and aliphatic molecules. Overall, no particular association was identified between marine invertebrate taxa and chemical groups of new NPs. Nonetheless, it is worth noting that most NPs recorded from cnidarians and mollusks were terpenoids, while most NPs identified in echinoderms were aliphatic compounds or carbohydrates. The geographical trends observed in our study do not support the idea of particular chemical groups of new NPs being associated with marine invertebrates from any specific geographical region, as NPs from different chemical groups were commonly distributed worldwide. Full article

(This article belongs to the Collection Bioactive Compounds)

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213 KiB

Open AccessCommunication

Towards Recyclable NAD(P)H Regeneration Catalysts

by Miriam De Torres, Jonas Dimroth, Isabel W. C. E. Arends, Juliane Keilitz and Frank Hollmann

Molecules 2012, 17(8), 9835-9841; https://doi.org/10.3390/molecules17089835 - 15 Aug 2012

Cited by 28 | Viewed by 7429

Abstract

Rh(III)-TsDPEN, an immobilized analog of the well-known [Cp*Rh(bpy)(H₂O)]²⁺ was evaluated as a heterogeneous, recyclable regeneration catalyst for reduced oxidoreductase cofactors [NAD(P)H]. Repeated use of this catalyst was established and the catalytic properties were initially investigated. Apparently, Rh(III)-TsDPEN is [...] Read more.

Rh(III)-TsDPEN, an immobilized analog of the well-known [Cp*Rh(bpy)(H₂O)]²⁺ was evaluated as a heterogeneous, recyclable regeneration catalyst for reduced oxidoreductase cofactors [NAD(P)H]. Repeated use of this catalyst was established and the catalytic properties were initially investigated. Apparently, Rh(III)-TsDPEN is prone to severe diffusion limitations, necessitating further developments. Overall, a promising concept for chemoenzymatic redox catalysis is proposed, which may overcome some of the current limitations such as catalyst cost and incompatibility of Rh with some biocatalysts. Full article

(This article belongs to the Special Issue Enzyme-Catalyzed Reactions)

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1823 KiB

Open AccessReview

Microfluidic Approaches to Bacterial Biofilm Formation

by Junghyun Kim, Hee-Deung Park and Seok Chung

Molecules 2012, 17(8), 9818-9834; https://doi.org/10.3390/molecules17089818 - 15 Aug 2012

Cited by 131 | Viewed by 19001

Abstract

Bacterial biofilms—aggregations of bacterial cells and extracellular polymeric substrates (EPS)—are an important subject of research in the fields of biology and medical science. Under aquatic conditions, bacterial cells form biofilms as a mechanism for improving survival and dispersion. In this review, we discuss [...] Read more.

Bacterial biofilms—aggregations of bacterial cells and extracellular polymeric substrates (EPS)—are an important subject of research in the fields of biology and medical science. Under aquatic conditions, bacterial cells form biofilms as a mechanism for improving survival and dispersion. In this review, we discuss bacterial biofilm development as a structurally and dynamically complex biological system and propose microfluidic approaches for the study of bacterial biofilms. Biofilms develop through a series of steps as bacteria interact with their environment. Gene expression and environmental conditions, including surface properties, hydrodynamic conditions, quorum sensing signals, and the characteristics of the medium, can have positive or negative influences on bacterial biofilm formation. The influences of each factor and the combined effects of multiple factors may be addressed using microfluidic approaches, which provide a promising means for controlling the hydrodynamic conditions, establishing stable chemical gradients, performing measurement in a high-throughput manner, providing real-time monitoring, and providing in vivo-like in vitro culture devices. An increased understanding of biofilms derived from microfluidic approaches may be relevant to improving our understanding of the contributions of determinants to bacterial biofilm development. Full article

(This article belongs to the Special Issue Flow Chemistry)

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350 KiB

Open AccessArticle

Neuroprotective Activity of Lavender Oil on Transient Focal Cerebral Ischemia in Mice

by Dong Wang, Xuan Yuan, Ting Liu, Liangliang Liu, Yanli Hu, Zhenhua Wang and Qiusheng Zheng

Molecules 2012, 17(8), 9803-9817; https://doi.org/10.3390/molecules17089803 - 15 Aug 2012

Cited by 76 | Viewed by 11257

Abstract

The air-dried aerial parts of Lavandula angustifolia Mill, a traditional Uygur herbal drug, is used as resuscitation-inducing therapy to treat neurodisfunctions, such as stroke. This study was designed to assess the neuroprotective effects of lavender oil against ischemia/reperfusion (IR) injury in mice. [...] Read more.

The air-dried aerial parts of Lavandula angustifolia Mill, a traditional Uygur herbal drug, is used as resuscitation-inducing therapy to treat neurodisfunctions, such as stroke. This study was designed to assess the neuroprotective effects of lavender oil against ischemia/reperfusion (IR) injury in mice. Focal cerebral ischemia was induced by the intraluminal occlusion method with a nylon string. The neurodysfuntion was evaluated by neurological deficit and the infarct area was showed by 2,3,5-triphenyltetrazolium chloride (TTC) staining. The histopathological changes were observed by hematoxylin and eosin staining. The levels of mitochondria-generated reactive oxygen species (ROS), malondialdehyde (MDA) and carbonyl, the ratio of reduced glutathione (GSH)/glutathione disulfide (GSSG), the activities of superoxide dismutase (SOD), catalase (CAT) and glutathion peroxidase (GSH-Px) in brain tissue were measured to estimate the oxidative stress state. Neurological deficit, infarct size, histopathology changes and oxidative stress markers were evaluated after 22 h of reperfusion. In comparison with the model group, treatment with lavender oil significantly decreased neurological deficit scores, infarct size, the levels of MDA, carbonyl and ROS, and attenuated neuronal damage, upregulated SOD, CAT, GSH-Px activities and GSH/GSSG ratio. These results suggested that the neuroprotective effects of lavender oil against cerebral ischemia/reperfusion injury may be attributed to its antioxidant effects. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics

by Jon K. Fairweather, Ligong Liu, Tomislav Karoli and Vito Ferro

Molecules 2012, 17(8), 9790-9802; https://doi.org/10.3390/molecules17089790 - 15 Aug 2012

Cited by 10 | Viewed by 8565

Abstract

A 6-deoxy-a-L-talopyranoside acceptor was readily prepared from methyl a-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired a-linked disaccharide (69–90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (a:b = 6:1), but [...] Read more.

A 6-deoxy-a-L-talopyranoside acceptor was readily prepared from methyl a-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired a-linked disaccharide (69–90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (a:b = 6:1), but the desired a-linked disaccharide could be isolated in good overall yield (60%) following conversion into its corresponding tribenzoate derivative. The disaccharides were designed to mimic the heparan sulfate (HS) disaccharide GlcN(2S,6S)-IdoA(2S). However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics. Full article

(This article belongs to the Special Issue Advances in Carbohydrate Chemistry 2012)

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Open AccessArticle

Cloning, Purification, and Characterization of a Heat- and Alkaline-Stable Endoglucanase B from Aspergillus niger BCRC31494

by Chien-Huang Li, Hsing-Ren Wang and Tsong-Rong Yan

Molecules 2012, 17(8), 9774-9789; https://doi.org/10.3390/molecules17089774 - 14 Aug 2012

Cited by 26 | Viewed by 7230

Abstract

Endoglucanase B (EGLB) derived from Aspergillus niger BCRC31494 has been used in the food fermentation industry because of its thermal and alkaline tolerance. It was cloned and expressed in Pichia pastoris. According to sequence analysis, the gene open reading frame comprises 1,217 [...] Read more.

Endoglucanase B (EGLB) derived from Aspergillus niger BCRC31494 has been used in the food fermentation industry because of its thermal and alkaline tolerance. It was cloned and expressed in Pichia pastoris. According to sequence analysis, the gene open reading frame comprises 1,217 bp with five introns (GenBank GQ292753). According to sequence and protein domain analyses, EGLB was assigned to glycosyl hydrolase family 5 of the cellulase superfamily. Several binding sites were found in the promoter region. The purified recombinant enzyme was induced by 0.5% methanol, and it exhibited optimal activity at 70 °C and pH 4. EGLB was stable for 3 h at temperatures below 60 °C, with more than 90% of its activity remaining. The enzyme was specific for substrates with β-1,3 and β-1,4 linkages. In Lineweaver-Burk plot analysis, the K_m and V_max values of EGLB for β-D-glucan were 134 mg/mL and 4.68 U/min/mg, respectively. The enzyme activity was increased by 1.86-fold by Co²⁺ and by 2-fold by Triton X-100 and Tween 80. These favorable properties make EGLB a potential candidate for use in laundry and textile industrial applications. Full article

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Open AccessArticle

Antioxidative Properties of Defatted Dabai Pulp and Peel Prepared by Solid Phase Extraction

by Hock Eng Khoo, Azrina Azlan, Amin Ismail and Faridah Abas

Molecules 2012, 17(8), 9754-9773; https://doi.org/10.3390/molecules17089754 - 14 Aug 2012

Cited by 25 | Viewed by 8521

Abstract

Solid phase extraction (SPE) using Sep-Pak^® cartridges is one of the techniques used for fractionation of antioxidant compounds in waste of dabai oil extraction (defatted dabai parts). The aim of this study was to determine the phenolic compounds and antioxidant capacity in [...] Read more.

Solid phase extraction (SPE) using Sep-Pak^® cartridges is one of the techniques used for fractionation of antioxidant compounds in waste of dabai oil extraction (defatted dabai parts). The aim of this study was to determine the phenolic compounds and antioxidant capacity in crude extracts and several SPE fractions from methanolic extract of defatted dabai pulp and peel. Based on SPE, Sep-Pak^® cyanopropyl and C₁₈ cartridges were used to fractionate the antioxidant-rich crude extracts into water and methanolic fractions. Analyzed using LC-MS, flavonoids, anthocyanins, saponin derivatives and other unknown antioxidative compounds were detected in the defatted dabai crude extracts and their SPE fractions. Anthocyanins were the major phenolic compounds identified in the defatted dabai peel and detected in most of the SPE fractions. Methanolic fractions of defatted dabai parts embraced higher total phenolics and antioxidant capacity than water fractions. This finding also revealed the crude extracts of defatted dabai peel have the most significant antioxidant properties compared to the methanolic and water fractions studied. The crude extract of defatted dabai parts remain as the most potent antioxidant as it contains mixture of flavonoids, anthocyanins and other potential antioxidants. Full article

(This article belongs to the Section Natural Products Chemistry)

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207 KiB

Open AccessArticle

Fungal Strains as Catalysts for the Biotransformation of Halolactones by Hydrolytic Dehalogenation with the Dimethylcyclohexane System

by Małgorzata Grabarczyk

Molecules 2012, 17(8), 9741-9753; https://doi.org/10.3390/molecules17089741 - 14 Aug 2012

Cited by 18 | Viewed by 5996

Abstract

Bicyclic chloro-, bromo- and iodo-γ-lactones with dimethylcyclohexane rings were used as substrates for bioconversion by several fungal strains (Fusarium, Botrytis and Beauveria). Most of the selected microorganisms transformed these lactones by hydrolytic dehalogenation into the new compound cis-2-hydroxy-4,6-dimethyl-9-oxabicyclo[4.3.0]- nonan-8-one, [...] Read more.

Bicyclic chloro-, bromo- and iodo-γ-lactones with dimethylcyclohexane rings were used as substrates for bioconversion by several fungal strains (Fusarium, Botrytis and Beauveria). Most of the selected microorganisms transformed these lactones by hydrolytic dehalogenation into the new compound cis-2-hydroxy-4,6-dimethyl-9-oxabicyclo[4.3.0]- nonan-8-one, mainly the (−)-isomer. When iodo-γ-lactone was used as the substrate, two products were observed: a hydroxy-γ-lactone and an unsaturated lactone. The structures of all substrates and products were established on the basis of their spectral data. The mechanism of dehalogenation of three halolactones was also studied. Full article

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Open AccessArticle

Exposure to Anacardiaceae Volatile Oils and Their Constituents Induces Lipid Peroxidation within Food-Borne Bacteria Cells

by Ricardo M. Montanari, Luiz C. A. Barbosa, Antonio J. Demuner, Cleber J. Silva, Nelio J. Andrade, Fyaz M. D. Ismail and Maria C. A. Barbosa

Molecules 2012, 17(8), 9728-9740; https://doi.org/10.3390/molecules17089728 - 14 Aug 2012

Cited by 57 | Viewed by 7687

Abstract

The chemical composition of the volatile oils from five Anacardiaceae species and their activities against Gram positive and negative bacteria were assessed. The peroxidative damage within bacterial cell membranes was determined through the breakdown product malondialdehyde (MDA). The major constituents in Anacardium humile [...] Read more.

The chemical composition of the volatile oils from five Anacardiaceae species and their activities against Gram positive and negative bacteria were assessed. The peroxidative damage within bacterial cell membranes was determined through the breakdown product malondialdehyde (MDA). The major constituents in Anacardium humile leaves oil were (E)-caryophyllene (31.0%) and α-pinene (22.0%), and in Anacardium occidentale oil they were (E)-caryophyllene (15.4%) and germacrene-D (11.5%). Volatile oil from Astronium fraxinifolium leaves were dominated by (E)-β-ocimene (44.1%) and α-terpinolene (15.2%), whilst the oil from Myracrodruon urundeuva contained an abundance of δ-3-carene (78.8%). However, Schinus terebinthifolius leaves oil collected in March and July presented different chemical compositions. The oils from all species, except the one from A. occidentale, exhibited varying levels of antibacterial activity against Staphylococcus aureus, Bacillus cereus and Escherichia coli. Oil extracted in July from S. terebinthifolius was more active against all bacterial strains than the corresponding oil extracted in March. The high antibacterial activity of the M. urundeuva oil could be ascribed to its high δ-3-carene content. The amounts of MDA generated within bacterial cells indicate that the volatile oils induce lipid peroxidation. The results suggest that one putative mechanism of antibacterial action of these volatile oils is pro-oxidant damage within bacterial cell membrane explaining in part their preservative properties. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessCommunication

Diterpenoids from the Buds of Pinus banksiana Lamb.

by Patricia Georges, Jean Legault, Serge Lavoie, Carole Grenon and André Pichette

Molecules 2012, 17(8), 9716-9727; https://doi.org/10.3390/molecules17089716 - 13 Aug 2012

Cited by 14 | Viewed by 6224

Abstract

Three new diterpenoids, namely 7α-hydroxyabieta-8,11,13,15-tetraen-18-oic acid, 7β,15,18-trihydroxyabieta-8,11,13-triene, 13,15-dihydroxypodocarpa-8,11,13-triene, and 12 other known compounds were isolated from buds of Pinus banksiana Lamb. All these compounds, except for 7-oxodehydroabietinol, were isolated for the first time from this plant. Their structures were elucidated by detailed spectroscopic [...] Read more.

Three new diterpenoids, namely 7α-hydroxyabieta-8,11,13,15-tetraen-18-oic acid, 7β,15,18-trihydroxyabieta-8,11,13-triene, 13,15-dihydroxypodocarpa-8,11,13-triene, and 12 other known compounds were isolated from buds of Pinus banksiana Lamb. All these compounds, except for 7-oxodehydroabietinol, were isolated for the first time from this plant. Their structures were elucidated by detailed spectroscopic studies and comparison with published data. All isolated compounds were tested for cytotoxic and antibacterial activities. Overall, two compounds, 7-oxodehydroabietinol and 18-nor-4,15-dihydroxyabieta-8,11,13-trien-7-one, showed moderate cytotoxicity against a human lung carcinoma cell line. Full article

(This article belongs to the Section Natural Products Chemistry)

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269 KiB

Open AccessReview

Corn Silk (Stigma Maydis) in Healthcare: A Phytochemical and Pharmacological Review

by Khairunnisa Hasanudin, Puziah Hashim and Shuhaimi Mustafa

Molecules 2012, 17(8), 9697-9715; https://doi.org/10.3390/molecules17089697 - 13 Aug 2012

Cited by 205 | Viewed by 38255

Abstract

Corn silk (Stigma maydis) is an important herb used traditionally by the Chinese, and Native Americans to treat many diseases. It is also used as traditional medicine in many parts of the world such as Turkey, United States and France. Its [...] Read more.

Corn silk (Stigma maydis) is an important herb used traditionally by the Chinese, and Native Americans to treat many diseases. It is also used as traditional medicine in many parts of the world such as Turkey, United States and France. Its potential antioxidant and healthcare applications as diuretic agent, in hyperglycemia reduction, as anti-depressant and anti-fatigue use have been claimed in several reports. Other uses of corn silk include teas and supplements to treat urinary related problems. The potential use is very much related to its properties and mechanism of action of its plant’s bioactive constituents such as flavonoids and terpenoids. As such, this review will cover the research findings on the potential applications of corn silk in healthcare which include its phytochemical and pharmacological activities. In addition, the botanical description and its toxicological studies are also included. Full article

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Open AccessArticle

Synthesis and Biological Evaluation of 3-Aryl-quinoxaline-2-carbonitrile 1,4-Di-N-oxide Derivatives as Hypoxic Selective Anti-tumor Agents

by Yunzhen Hu, Qing Xia, Shihao Shangguan, Xiaowen Liu, Yongzhou Hu and Rong Sheng

Molecules 2012, 17(8), 9683-9696; https://doi.org/10.3390/molecules17089683 - 13 Aug 2012

Cited by 31 | Viewed by 7831

Abstract

A series of 3-aryl-2-quinoxaline-carbonitrile 1,4-di-N-oxide derivatives were designed, synthesized and evaluated for hypoxic and normoxic cytotoxic activity against human SMMC-7721, K562, KB, A549 and PC-3 cell lines. Many of these new compounds displayed more potent hypoxic cytotoxic activity compared with TX-402 [...] Read more.

A series of 3-aryl-2-quinoxaline-carbonitrile 1,4-di-N-oxide derivatives were designed, synthesized and evaluated for hypoxic and normoxic cytotoxic activity against human SMMC-7721, K562, KB, A549 and PC-3 cell lines. Many of these new compounds displayed more potent hypoxic cytotoxic activity compared with TX-402 and TPZ in the tumor cells based evaluation, which confirmed our hypothesis that the replacement of the 3-amine with the substituted aryl ring of TX-402 increases the hypoxic anti-tumor activity. The preliminary SAR revealed that 3-chloro was a favorable substituent in the phenyl ring for hypoxic cytotoxicity and 7-methyl or 7-methoxy substituted derivatives exhibited better hypoxic selectivity against most of the tested cell lines. The most potent compound, 7-methyl-3-(3-chlorophenyl)-quinoxaline-2-carbonitrile 1,4-dioxide (9h) was selected for further anti-tumor evaluation and mechanistic study. It also exhibited significant cytotoxic activity against BEL-7402, HepG2, HL-60, NCI-H460, HCT-116 and CHP126 cell lines in hypoxia with IC₅₀ values ranging from 0.31 to 3.16 μM, and preliminary mechanism study revealed that 9h induced apoptosis in a caspase-dependent pathway. Full article

(This article belongs to the Section Medicinal Chemistry)

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367 KiB

Open AccessArticle

Evaluation of Flavonoid Contents and Antioxidant Capacity of the Aerial Parts of Common and Tartary Buckwheat Plants

by Danuta Zielińska, Marcin Turemko, Jacek Kwiatkowski and Henryk Zieliński

Molecules 2012, 17(8), 9668-9682; https://doi.org/10.3390/molecules17089668 - 13 Aug 2012

Cited by 100 | Viewed by 7329

Abstract

The analysis of major and minor flavonoids, and antioxidant capacity of stems, leaves, flowers, unripe seeds and ripe seeds of common and tartary buckwheat plants collected during different growth periods was addressed in this study. The highest rutin contents were observed in flowers [...] Read more.

The analysis of major and minor flavonoids, and antioxidant capacity of stems, leaves, flowers, unripe seeds and ripe seeds of common and tartary buckwheat plants collected during different growth periods was addressed in this study. The highest rutin contents were observed in flowers and leaves collected from common and tartary buckwheat at early flowering as well as flowering and seed formation states. A low quercetin contents were found in all studied aerial part of buckwheat plants. Quercitrin (quercetin-3-rhamnoside) was only found in flowers collected at different growth periods while flavone C-glucosides were accumulated preferentially only in unripe seeds collected from common buckwheat at an early flowering state. The rank of antioxidant capacity provided for aerial parts of common and tartary buckwheat at early flowering state was as follows: flowers > leaves > stems. The highest contribution of rutin to the antioxidant capacity of the aerial parts of common and tartary buckwheat was found for stems followed by leaves, flowers and unripe seeds. The results demonstrate that flowers from common and tartary buckwheat collected at early flowering as well as flowering and seed formation states have the future potential to be a useful food ingredient. Full article

(This article belongs to the Special Issue Methods in Polyphenol Analysis)

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275 KiB

Open AccessArticle

Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity

by Mohamed M. Youssef and Mahmoud A. Amin

Molecules 2012, 17(8), 9652-9667; https://doi.org/10.3390/molecules17089652 - 13 Aug 2012

Cited by 61 | Viewed by 7733

Abstract

Biginelli reaction of ethyl acetoacetate, thiourea and the appropriate aromatic aldehyde was used to produce ethyl 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylates, that reacted with bromomalononitrile to give ethyl 3-amino-5-aryl-2-cyano-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates rather than the isomeric 7H-thiazolo[3,2-a]pyrimidines. Thiazolopyrimidine derivatives reacted with carbon [...] Read more.

Biginelli reaction of ethyl acetoacetate, thiourea and the appropriate aromatic aldehyde was used to produce ethyl 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylates, that reacted with bromomalononitrile to give ethyl 3-amino-5-aryl-2-cyano-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates rather than the isomeric 7H-thiazolo[3,2-a]pyrimidines. Thiazolopyrimidine derivatives reacted with carbon disulphide to yield ethyl 9-aryl-7-methyl-2,4-dithioxo-2,3,4,9-tetrahydro-1H-thiazolo[3,2-a:4,5-d']dipyrimidine-8-carboxylates, that reacted with phenacyl bromide to produce ethyl 8-methyl-10-(4-methoxyphenyl)-3-substituted-5-thioxo-2(un)subatituted-10H-thiazolo[3'',2'':1',2']pyrimido[4',5':4,5]thiazolo[3,2-a]pyrimidine-9-carboxylates. The aforementioned reactions were carried out using both conventional chemical methods and with the assistance of microwave irradaition. Comparison between both methods showed that the microwave assisted method is preferable because of the time reduction and yield improvements achieved. The new compounds were tested for their biological activity as antioxidants, antibacterial or antifungal agents. Some of the new compounds were found to have moderate to good antioxidant and antimicrobial activities. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

Deoxycalyciphylline B, a Hepatotoxic Alkaloid from Daphniphyllum calycinum

by Xiaopo Zhang, Junqing Zhang, Yinfeng Tan, Qibing Liu and Mingsheng Liu

Molecules 2012, 17(8), 9641-9651; https://doi.org/10.3390/molecules17089641 - 13 Aug 2012

Cited by 10 | Viewed by 8185

Abstract

Daphniphyllum calycinum (DC), a main component of Chinese patent drug Fengliao-Changweikang, is effectively used to cure bowel disease in the clinic. It was recorded that DC possessed slight toxicity, which was caused by the alkaloids existing in its extract. Unfortunately, to date the [...] Read more.

Daphniphyllum calycinum (DC), a main component of Chinese patent drug Fengliao-Changweikang, is effectively used to cure bowel disease in the clinic. It was recorded that DC possessed slight toxicity, which was caused by the alkaloids existing in its extract. Unfortunately, to date the toxicity level and toxic constituents are still unclear. The present study is designed to illustrate the acute toxicity and induced organ damages of the total alkaloids as well as to determine the toxic constituents. Based on the above studies, not only was the acute toxicity determined but also hepatic toxicity was characterized by increased plasma biomarkers of ALT and AST and liver cell inflammatory infiltrate as well necrosis that was firstly observed. Significantly, deoxycalyciphylline B exhibited exactly the same hepatic toxicity so it was identified as the main toxic constituent in DC. An obvious dose-effect relationship between the toxic compound and induced hepatic injuries was also observed. Moreover, the Chinese patent drug Fengliao-Changweikang contained low levels of the toxic compound, compared with the total alkaloids. Therefore, this Chinese patent drug could be regarded to be safe in this point of view. Full article

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245 KiB

Open AccessArticle

In Vitro Anti-diabetic Activities and Chemical Analysis of Polypeptide-k and Oil Isolated from Seeds of Momordica charantia (Bitter Gourd)

by Zuraini Ahmad, Khairul Faizi Zamhuri, Azhar Yaacob, Chiong Hoe Siong, Malarvili Selvarajah, Amin Ismail and Muhammad Nazrul Hakim

Molecules 2012, 17(8), 9631-9640; https://doi.org/10.3390/molecules17089631 - 10 Aug 2012

Cited by 85 | Viewed by 12233

Abstract

The amino acid and fatty acid composition of polypeptide k and oil isolated from the seeds of Momordica charantia was analysed. The analysis revealed polypeptide k contained 9 out of 11 essential amino acids, among a total of 18 types of amino acids. [...] Read more.

The amino acid and fatty acid composition of polypeptide k and oil isolated from the seeds of Momordica charantia was analysed. The analysis revealed polypeptide k contained 9 out of 11 essential amino acids, among a total of 18 types of amino acids. Glutamic acid, aspartic acid, arginine and glycine were the most abundant (17.08%, 9.71%, 9.50% and 8.90% of total amino acids, respectively). Fatty acid analysis showed unusually high amounts of C18-0 (stearic acid, 62.31% of total fatty acid). C18-1 (oleic acid) and C18-2 (linoleic acid) were the other major fatty acid detected (12.53% and 10.40%, respectively). The oil was devoid of the short fatty acids (C4-0 to C8-0). Polypeptide k and oil were also subjected to in vitro α-glucosidase and α-amylase inhibition assays. Both polypeptide k and seed oil showed potent inhibition of α-glucosidase enzyme (79.18% and 53.55% inhibition, respectively). α-Amylase was inhibited by 35.58% and 38.02%, respectively. Collectively, the in vitro assay strongly suggests that both polypeptide k and seed oil from Momordica charantia are potent potential hypoglycemic agents. Full article

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191 KiB

Open AccessArticle

Populene D Analogues: Design, Concise Synthesis and Antiproliferative Activity

by Kachi R. Kishore Kumar Reddy, Giovanna B. Longato, João E. de Carvalho, Ana L. T. G. Ruiz and Luiz F. Silva, Jr.

Molecules 2012, 17(8), 9621-9630; https://doi.org/10.3390/molecules17089621 - 10 Aug 2012

Cited by 9 | Viewed by 5408

Abstract

An efficient and concise synthesis of nine populene D analogues was performed using an iodine-catalyzed Prins cyclization as the key transformation. The antiproliferative activity of these new pyrans against several cancer cell lines was then investigated. Among them, an isochromene with moderate activity [...] Read more.

An efficient and concise synthesis of nine populene D analogues was performed using an iodine-catalyzed Prins cyclization as the key transformation. The antiproliferative activity of these new pyrans against several cancer cell lines was then investigated. Among them, an isochromene with moderate activity (mean logGI₅₀ = 0.91) was found. Additionally, compounds with selectivity toward the tumor cell lines NCI-ADR/RES, OVCAR-3, and HT29 were discovered. Full article

(This article belongs to the Section Organic Chemistry)

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444 KiB

Open AccessArticle

Design and Synthesis of a Novel Ganglioside Ligand for Influenza A Viruses ^†

by Tomohiro Nohara, Akihiro Imamura, Maho Yamaguchi, Kazuya I. P. J. Hidari, Takashi Suzuki, Tatsuya Komori, Hiromune Ando, Hideharu Ishida and Makoto Kiso

Molecules 2012, 17(8), 9590-9620; https://doi.org/10.3390/molecules17089590 - 10 Aug 2012

Cited by 10 | Viewed by 7625

Abstract

A novel ganglioside bearing Neua2-3Gal and Neua2-6Gal structures as distal sequences was designed as a ligand for influenza A viruses. The efficient synthesis of the designed ganglioside was accomplished by employing the cassette coupling approach as a key reaction, which was executed between [...] Read more.

A novel ganglioside bearing Neua2-3Gal and Neua2-6Gal structures as distal sequences was designed as a ligand for influenza A viruses. The efficient synthesis of the designed ganglioside was accomplished by employing the cassette coupling approach as a key reaction, which was executed between the non-reducing end of the oligosaccharide and the cyclic glucosylceramide moiety. Examination of its binding activity to influenza A viruses revealed that the new ligand is recognized by Neua2-3 and 2-6 type viruses. Full article

(This article belongs to the Special Issue Advances in Carbohydrate Chemistry 2012)

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1735 KiB

Open AccessArticle

In Vitro and in Vivo Antitumor Effect of Trachylobane-360, a Diterpene from Xylopia langsdorffiana

by João Carlos Lima Rodrigues Pita, Aline Lira Xavier, Tatyanna Kelvia Gomes de Sousa, Vivianne Mendes Mangueira, Josean Fechine Tavares, Robson José de Oliveira Júnior, Robson Cavalcante Veras, Hilzeth de Luna Freire Pessoa, Marcelo Sobral da Silva, Sandra Morelli, Veridiana de Melo Rodrigues Ávila, Teresinha Gonçalves da Silva, Margareth de Fátima Formiga Melo Diniz and Marianna Vieira Sobral Castello-Branco

Molecules 2012, 17(8), 9573-9589; https://doi.org/10.3390/molecules17089573 - 10 Aug 2012

Cited by 30 | Viewed by 8317

Abstract

Trachylobane-360 (ent-7α-acetoxytrachyloban-18-oic acid) was isolated from Xylopia langsdorffiana. Studies have shown that it has weak cytotoxic activity against tumor and non-tumor cells. This study investigated the in vitro and in vivo antitumor effects of trachylobane-360, as well as its cytotoxicity [...] Read more.

Trachylobane-360 (ent-7α-acetoxytrachyloban-18-oic acid) was isolated from Xylopia langsdorffiana. Studies have shown that it has weak cytotoxic activity against tumor and non-tumor cells. This study investigated the in vitro and in vivo antitumor effects of trachylobane-360, as well as its cytotoxicity in mouse erythrocytes. In order to evaluate the in vivo toxicological aspects related to trachylobane-360 administration, hematological, biochemical and histopathological analyses of the treated animals were performed. The compound exhibited a concentration-dependent effect in inducing hemolysis with HC₅₀ of 273.6 µM, and a moderate in vitro concentration-dependent inhibitory effect on the proliferation of sarcoma 180 cells with IC₅₀ values of 150.8 µM and 150.4 µM, evaluated by the trypan blue exclusion test and MTT reduction assay, respectively. The in vivo inhibition rates of sarcoma 180 tumor development were 45.60, 71.99 and 80.06% at doses of 12.5 and 25 mg/kg of trachylobane-360 and 25 mg/kg of 5-FU, respectively. Biochemical parameters were not altered. Leukopenia was observed after 5-FU treatment, but this effect was not seen with trachylobane-360 treatment. The histopathological analysis of liver and kidney showed that both organs were mildly affected by trachylobane-360 treatment. Trachylobane-360 showed no immunosuppressive effect. In conclusion, these data reinforce the anticancer potential of this natural diterpene. Full article

(This article belongs to the Section Natural Products Chemistry)

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Molecules, Volume 17, Issue 8 (August 2012) – 94 articles , Pages 8735-9999

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