Molecules

697 KiB

Open AccessArticle

Fatty Acid Profile of Milk and Cheese from Dairy Cows Supplemented a Diet with Palm Kernel Cake

by Ronaldo Oliveira, Mario Faria, Raimundo Silva, Leilson Bezerra, Gleidson Carvalho, Alyson Pinheiro, Juliana Simionato and André Leão

Molecules 2015, 20(8), 15434-15448; https://doi.org/10.3390/molecules200815434 - 24 Aug 2015

Cited by 50 | Viewed by 7229

Abstract

Lipid supplements (oilseeds vegetables) are included in ruminant diet to increase its energy density and improve fatty acid composition of milk and consequently of fresh cheese. Milk and cheeses were evaluated from crossbred Holstein × Zebu, fed diets enriched with 0%, 25%, 50%, [...] Read more.

Lipid supplements (oilseeds vegetables) are included in ruminant diet to increase its energy density and improve fatty acid composition of milk and consequently of fresh cheese. Milk and cheeses were evaluated from crossbred Holstein × Zebu, fed diets enriched with 0%, 25%, 50%, and 75% inclusion levels of palm kernel cake in concentrated supplement, which were supplied daily (3.0 kg). Milk and fresh cheese (p = 0.001) fatty acids C12:0 exhibited quadratic negative values. Milk fatty acids C13:0, C20:0, C18:2t10c12, and C20:2n-6 presented positive quadratic values. The milk C18:2n-6 decreased linearly and in fresh cheese exhibited an increasing linear effect (p = 0.016). However, the fatty acids grouped in milk fat were not affected. The medium-chain fatty acids varied negatively and quadratically (p = 0.045). There was no effect on milk and fresh cheese chemical composition (p > 0.05). The milk fat was increased (p = 0.0065) quadratically (minimum point of 24.7%). Thus, the addition of palm kernel cake to cow diets negatively altered the fatty acid profile, it raises the percentage of lauric (C12) and tridecanoic (C13) acids fat which is not beneficial to human health from a nutraceutical perspective, although it did not influence the atherogenicity index. Full article

(This article belongs to the Section Metabolites)

1661 KiB

Open AccessReview

The Potential Use of Natural and Structural Analogues of Antimicrobial Peptides in the Fight against Neglected Tropical Diseases

by Angélique Lewies, Johannes Frederik Wentzel, Garmi Jacobs and Lissinda Hester Du Plessis

Molecules 2015, 20(8), 15392-15433; https://doi.org/10.3390/molecules200815392 - 24 Aug 2015

Cited by 49 | Viewed by 10623 | Correction

Abstract

Recently, research into the development of new antimicrobial agents has been driven by the increase in resistance to traditional antibiotics and Emerging Infectious Diseases. Antimicrobial peptides (AMPs) are promising candidates as alternatives to current antibiotics in the treatment and prevention of microbial infections. [...] Read more.

Recently, research into the development of new antimicrobial agents has been driven by the increase in resistance to traditional antibiotics and Emerging Infectious Diseases. Antimicrobial peptides (AMPs) are promising candidates as alternatives to current antibiotics in the treatment and prevention of microbial infections. AMPs are produced by all known living species, displaying direct antimicrobial killing activity and playing an important role in innate immunity. To date, more than 2000 AMPs have been discovered and many of these exhibit broad-spectrum antibacterial, antiviral and anti-parasitic activity. Neglected tropical diseases (NTDs) are caused by a variety of pathogens and are particularly wide-spread in low-income and developing regions of the world. Alternative, cost effective treatments are desperately needed to effectively battle these medically diverse diseases. AMPs have been shown to be effective against a variety of NTDs, including African trypanosomes, leishmaniosis and Chagas disease, trachoma and leprosy. In this review, the potential of selected AMPs to successfully treat a variety of NTD infections will be critically evaluated. Full article

(This article belongs to the Collection Natural Products as Leads or Drugs against Neglected Tropical Diseases)

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936 KiB

Open AccessArticle

Structure-Activity Relationships of the Antitumor C5-Curcuminoid GO-Y030

by Aki Kohyama, Hiroyuki Yamakoshi, Shoko Hongo, Naoki Kanoh, Hiroyuki Shibata and Yoshiharu Iwabuchi

Molecules 2015, 20(8), 15374-15391; https://doi.org/10.3390/molecules200815374 - 24 Aug 2015

Cited by 23 | Viewed by 7578

Abstract

1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one (2) was isolated from Curcuma domestica as a curcumin (1)-related compound, which we named C5-curcumin. Intrigued by the potent antitumor activity of C5-curcumin (2)-related 1,5-bisaryl-1,4-pentadiene-3-ones [bis(arylmethylidene)acetones, termed C5-curcuminoids], we previously conducted a structure–activity relationship study of C5-curcuminoids and showed that highly active [...] Read more.

1,5-Bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one (2) was isolated from Curcuma domestica as a curcumin (1)-related compound, which we named C5-curcumin. Intrigued by the potent antitumor activity of C5-curcumin (2)-related 1,5-bisaryl-1,4-pentadiene-3-ones [bis(arylmethylidene)acetones, termed C5-curcuminoids], we previously conducted a structure–activity relationship study of C5-curcuminoids and showed that highly active GO-Y030 [1,5-bis(3,5-bis(methoxymethoxy)phenyl)-1,4-pentadiene-3-one (4)] is the most promising antitumor compound. In this study, a panel of C5-curcuminoids based on GO-Y030, consisting of 30 new and 10 known compounds, was synthesized to elucidate in detail which moiety of GO-Y030 is significant for antitumor activity. The results confirmed that both the cross-conjugated dienone moiety and the 3,5-bis(methoxymethoxy) substituent are important for the antitumor activity. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Phenyllactic Acid from Lactobacillus plantarum PromotesAdipogenic Activity in 3T3-L1 Adipocyte via Up-Regulationof PPAR-γ2

by Soundharrajan Ilavenil, Da Hye Kim, Mariadhas Valan Arasu, Srisesharam Srigopalram, Ravikumar Sivanesan and Ki Choon Choi

Molecules 2015, 20(8), 15359-15373; https://doi.org/10.3390/molecules200815359 - 24 Aug 2015

Cited by 21 | Viewed by 8037

Abstract

Synthetic drugs are commonly used to cure various human ailments at present. However, the uses of synthetic drugs are strictly regulated because of their adverse effects. Thus, naturally occurring molecules may be more suitable for curing disease without unfavorable effects. Therefore, we investigated [...] Read more.

Synthetic drugs are commonly used to cure various human ailments at present. However, the uses of synthetic drugs are strictly regulated because of their adverse effects. Thus, naturally occurring molecules may be more suitable for curing disease without unfavorable effects. Therefore, we investigated phenyllactic acid (PLA) from Lactobacillus plantarum with respect to its effects on adipogenic genes and their protein expression in 3T3-L1 pre-adipocytes by qPCR and western blot techniques. PLA enhanced differentiation and lipid accumulation in 3T3-L1 cells at the concentrations of 25, 50, and 100 μM. Maximum differentiation and lipid accumulation were observed at a concentration of 100 μM of PLA, as compared with control adipocytes (p < 0.05). The mRNA and protein expression of PPAR-γ2, C/EBP‑α, adiponectin, fatty acid synthase (FAS), and SREBP-1 were increased by PLA treatment as compared with control adipocytes (p < 0.05). PLA stimulates PPAR-γ mRNA expression in a concentration dependent manner, but this expression was lesser than agonist (2.83 ± 0.014 fold) of PPAR-γ2. Moreover, PLA supplementation enhances glucose uptake in 3T3-L1 pre-adipocytes (11.81 ± 0.17 mM) compared to control adipocytes, but this glucose uptake was lesser than that induced by troglitazone (13.75 ± 0.95 mM) and insulin treatment (15.49 ± 0.20 mM). Hence, we conclude that PLA treatment enhances adipocyte differentiation and glucose uptake via activation of PPAR-γ2, and PLA may thus be the potential candidate for preventing Type 2 Diabetes Mellitus (T2DM). Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

The Influence of Sesquiterpenes from Myrica rubra on the Antiproliferative and Pro-Oxidative Effects of Doxorubicin and Its Accumulation in Cancer Cells

by Martin Ambrož, Iva Boušová, Adam Skarka, Veronika Hanušová, Věra Králová, Petra Matoušková, Barbora Szotáková and Lenka Skálová

Molecules 2015, 20(8), 15343-15358; https://doi.org/10.3390/molecules200815343 - 21 Aug 2015

Cited by 59 | Viewed by 7794

Abstract

The sesquiterpenes β-caryophyllene, β-caryophyllene oxide (CAO), α-humulene (HUM), trans-nerolidol (NER), and valencene (VAL) are substantial components of the essential oil from Myrica rubra leaves which has exhibited significant antiproliferative effects in several intestinal cancer cell lines, with CaCo-2 cells being the most [...] Read more.

The sesquiterpenes β-caryophyllene, β-caryophyllene oxide (CAO), α-humulene (HUM), trans-nerolidol (NER), and valencene (VAL) are substantial components of the essential oil from Myrica rubra leaves which has exhibited significant antiproliferative effects in several intestinal cancer cell lines, with CaCo-2 cells being the most sensitive. The present study was designed to evaluate the effects of these sesquiterpenes on the efficacy and toxicity of the anticancer drug doxorubicin (DOX) in CaCo-2 cancer cells and in primary culture of rat hepatocytes. Our results showed that HUM, NER, VAL and CAO inhibited proliferation of CaCo-2 cancer cells but they did not affect the viability of hepatocytes. CAO, NER and VAL synergistically potentiated the efficacy of DOX in cancer cells killing. All sesquiterpenes exhibited the ability to selectively increase DOX accumulation in cancer cells and did not affect DOX concentration in hepatocytes. Additionally, CAO and VAL were able to increase the pro-oxidative effect of DOX in CaCo-2 cells. Moreover, CAO mildly ameliorated DOX toxicity in hepatocytes. Based on all results, CAO seems to be the most promising compound for further testing. Full article

(This article belongs to the Collection Herbal Medicine Research)

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Open AccessArticle

α-Glucosidase Inhibitors from Vauquelinia corymbosa

by Laura Flores-Bocanegra, Araceli Pérez-Vásquez, Mariana Torres-Piedra, Robert Bye, Edelmira Linares and Rachel Mata

Molecules 2015, 20(8), 15330-15342; https://doi.org/10.3390/molecules200815330 - 21 Aug 2015

Cited by 42 | Viewed by 7568

Abstract

The α-glucosidase inhibitory activity of an aqueous extract and compounds from the aerial parts of V. corymbosa was demonstrated with yeast and rat small intestinal α-glucosidases. The aqueous extract inhibited yeast α-glucosidase with a half maximal inhibitory concentration (IC₅₀) of 28.6 [...] Read more.

The α-glucosidase inhibitory activity of an aqueous extract and compounds from the aerial parts of V. corymbosa was demonstrated with yeast and rat small intestinal α-glucosidases. The aqueous extract inhibited yeast α-glucosidase with a half maximal inhibitory concentration (IC₅₀) of 28.6 μg/mL. Bioassay-guided fractionation of the extract led to the isolation of several compounds, including one cyanogenic glycoside [prunasin (1)], five flavonoids [(−)-epi-catechin (2), hyperoside (3), isoquercetin (4), quercitrin (5) and quercetin-3-O-(6′′-benzoyl)-β-galactoside (6)] and two simple aromatic compounds [picein (7) and methylarbutin (8)]. The most active compound was 6 with IC₅₀ values of 30 μM in the case of yeast α-glucosidase, and 437 μM in the case of the mammalian enzyme. According to the kinetic analyses performed with rat and yeast enzymes, this compound behaved as mixed-type inhibitor; the calculated inhibition constants (K_i) were 212 and 50 μM, respectively. Molecular docking analyses with yeast and mammalian α-glucosidases revealed that compound 6 bind differently to these enzymes. Altogether, the results of this work suggest that preparations of V. corymbosa might delay glucose absorption in vivo. Full article

(This article belongs to the Collection Bioactive Compounds)

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Open AccessArticle

Aqueous Extract of Tomato (Solanum lycopersicum L.) and Ferulic Acid Reduce the Expression of TNF-α and IL-1β in LPS-Activated Macrophages

by Simón Navarrete, Marcelo Alarcón and Iván Palomo

Molecules 2015, 20(8), 15319-15329; https://doi.org/10.3390/molecules200815319 - 21 Aug 2015

Cited by 54 | Viewed by 9247

Abstract

Acute inflammation is essential for defending the body against pathogens; however, when inflammation becomes chronic, it is harmful to the body and is part of the pathophysiology of various diseases such as Diabetes Mellitus type 2 (DM2) and Cardiovascular Disease (CVD) among others. [...] Read more.

Acute inflammation is essential for defending the body against pathogens; however, when inflammation becomes chronic, it is harmful to the body and is part of the pathophysiology of various diseases such as Diabetes Mellitus type 2 (DM2) and Cardiovascular Disease (CVD) among others. In chronic inflammation macrophages play an important role, mainly through the secretion of proinflammatory cytokines such as Tumor necrosis factor (TNF)-α and Interleukin (IL)-1β, explained in part by activation of the Toll-like receptor 4 (TLR4), a signaling pathway which culminates in the activation of Nuclear factor (NF)-κB, an important transcription factor in the expression of these proinflammatory genes. On the other hand, the benefits on health of a diet rich in fruit and vegetables are well described. In this work, the effects of aqueous extract of tomato and ferulic acid on the expression of proinflammatory cytokines in LPS activated monocyte-derived THP-1 macrophages were investigated. In addition, using Western blot, we investigated whether the inhibition was due to the interference on activation of NF-κB. We found that both the tomato extract and ferulic acid presented inhibitory activity on the expression of TNF-α and IL-1β cytokine by inhibiting the activation of NF-κB. The current results suggest that tomatoes and ferulic acid may contribute to prevention of chronic inflammatory diseases. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Optimization of Micellar Electrokinetic Chromatography Method for the Simultaneous Determination of Seven Hydrophilic and Four Lipophilic Bioactive Components in Three Salvia Species

by Jiliang Cao, Ji Hu, Jinchao Wei, Baocai Li, Mi Zhang, Cheng Xiang and Peng Li

Molecules 2015, 20(8), 15304-15318; https://doi.org/10.3390/molecules200815304 - 21 Aug 2015

Cited by 7 | Viewed by 4957

Abstract

A micellar electrokinetic chromatography (MEKC) method was developed for the simultaneous determination of seven hydrophilic phenolic acids and four lipophilic tanshinones in three Salvia species. In normal MEKC mode using SDS as surfactant, the investigated 11 compounds could not be well separated. Therefore, [...] Read more.

A micellar electrokinetic chromatography (MEKC) method was developed for the simultaneous determination of seven hydrophilic phenolic acids and four lipophilic tanshinones in three Salvia species. In normal MEKC mode using SDS as surfactant, the investigated 11 compounds could not be well separated. Therefore, several buffer modifiers including β-cyclodextrins (β-CD), ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) and organic solvents have been added to the buffer solution to improve the separation selectivity. Under the optimized conditions (BGE, 15 mM sodium tetraborate with 10 mM SDS, 5 mM β-CD, 10 mM [bmim]BF4 and 15% ACN (v/v) as additives; buffer pH, 9.8; voltage, 20 kV; temperature, 25 °C), the 11 investigated analytes could achieve baseline separation in 34 min. The proposed MEKC was additionally validated by evaluating the linearity (R² ≥ 0.9965), LODs (0.27–1.39 μg·mL^–1), and recovery (94.26%–105.17%), demonstrating this method was reproducible, accurate and reliable. Moreover, the contents of the 11 compounds in three Salvia species, including S. miltiorrhiza, S. przewalskii and S. castanea were analyzed. The result showed that the established MEKC method was simple and practical for the simultaneous determination of the hydrophilic and lipophilic bioactive components in Salvia species, which could be used to effectively evaluate the quality of these valued medicinal plants. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Design and Synthesis of Imidazopyrazolopyridines as Novel Selective COX-2 Inhibitors

by Mohamed G. Badrey, Hassan M. Abdel-Aziz, Sobhi M. Gomha, Mohamed M. Abdalla and Abdelrahman S. Mayhoub

Molecules 2015, 20(8), 15287-15303; https://doi.org/10.3390/molecules200815287 - 21 Aug 2015

Cited by 24 | Viewed by 7368

Abstract

The usefulness of non-steroidal anti-inflammatory drugs (NSAIDs) is hampered by their gastrointestinal side effects. Non-selective cyclooxygenases inhibitors interfere with both COX-1 and COX-2 isozymes. Since COX-1 mediates cytoprotection of gastric mucosa, its inhibition leads to the undesirable side effects. On the other hand, [...] Read more.

The usefulness of non-steroidal anti-inflammatory drugs (NSAIDs) is hampered by their gastrointestinal side effects. Non-selective cyclooxygenases inhibitors interfere with both COX-1 and COX-2 isozymes. Since COX-1 mediates cytoprotection of gastric mucosa, its inhibition leads to the undesirable side effects. On the other hand, COX-2 is undetectable in normal tissues and selectively induced by inflammatory stimuli. Therefore, it is strongly believed that the therapeutic benefits derive from inhibition of COX-2 only. The presence of a strong connection between reported COX-2 inhibitors and cardiac toxicity encourages medicinal chemists to explore new scaffolds. In the present study, we introduced imidazopyrazolopyridines as new potent and selective COX-2 inhibitors that lack the standard pharmacophoric binding features to hERG. Starting from our lead compound 5a, structure-based drug-design was conducted and more potent analogues were obtained with high COX-2 selectivity and almost full edema protection, in carrageenan-induced edema assay, in case of compound 5e. Increased bulkiness around imidazopyrazolopyridines by adding a substituted phenyl ring(s) afforded less active compounds. Full article

(This article belongs to the Section Organic Chemistry)

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Open AccessArticle

Ultrasound-Assisted Aqueous Two-Phase System for Extraction and Enrichment of Zanthoxylum armatum Lignans

by Tao Guo, Dan Su, Yan Huang, Ya Wang and Yong-Hui Li

Molecules 2015, 20(8), 15273-15286; https://doi.org/10.3390/molecules200815273 - 20 Aug 2015

Cited by 33 | Viewed by 5885

Abstract

In the study, an aqueous two phase system (ATPS) coupled with ultrasound was employed to extract lignans from Zanthoxylum armatum. Three standard lignans, namely (−)-fargesin, sesamin and L-asarinin, were used as marker compounds, and extraction was optimized and projected by response surface [...] Read more.

In the study, an aqueous two phase system (ATPS) coupled with ultrasound was employed to extract lignans from Zanthoxylum armatum. Three standard lignans, namely (−)-fargesin, sesamin and L-asarinin, were used as marker compounds, and extraction was optimized and projected by response surface methodology (RSM) and artificial neural network (ANN). The optimal condition for ATPS with 20% n-propanol and 24% (NH₄)₂SO₄ coupled with ultrasonic-assisted extraction including a solvent to solid ratio of 15:1, a temperature of 40 °C, and a treatment time of 55 min was obtained. Under the condition, the yield of (−)-fargesin increased 15.12%, and the purities of (−)-fargesin, sesamin and L-asarinin reached 2.222%, 1.066%, and 1.583%, with an increase of 44.38%, 25.70%, and 26.34% compared to those extracted with 95% ethanol, respectively. Coefficient of the determined (0.9855) and mean squared error (0.0018) of ANN model suggested good fitness and generalization of the ANN. Taken together, the results showed that ultrasonic-assisted ATPS can be a suitable method for extraction and enrichment of lignans from Z. armatum. Full article

(This article belongs to the Special Issue New Technologies for the Recovery of Natural Products)

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Open AccessReview

Optimal Energy Transfer in Light-Harvesting Systems

by Lipeng Chen, Prathamesh Shenai, Fulu Zheng, Alejandro Somoza and Yang Zhao

Molecules 2015, 20(8), 15224-15272; https://doi.org/10.3390/molecules200815224 - 20 Aug 2015

Cited by 41 | Viewed by 10177

Abstract

Photosynthesis is one of the most essential biological processes in which specialized pigment-protein complexes absorb solar photons, and with a remarkably high efficiency, guide the photo-induced excitation energy toward the reaction center to subsequently trigger its conversion to chemical energy. In this work, [...] Read more.

Photosynthesis is one of the most essential biological processes in which specialized pigment-protein complexes absorb solar photons, and with a remarkably high efficiency, guide the photo-induced excitation energy toward the reaction center to subsequently trigger its conversion to chemical energy. In this work, we review the principles of optimal energy transfer in various natural and artificial light harvesting systems. We begin by presenting the guiding principles for optimizing the energy transfer efficiency in systems connected to dissipative environments, with particular attention paid to the potential role of quantum coherence in light harvesting systems. We will comment briefly on photo-protective mechanisms in natural systems that ensure optimal functionality under varying ambient conditions. For completeness, we will also present an overview of the charge separation and electron transfer pathways in reaction centers. Finally, recent theoretical and experimental progress on excitation energy transfer, charge separation, and charge transport in artificial light harvesting systems is delineated, with organic solar cells taken as prime examples. Full article

(This article belongs to the Special Issue Light-Harvesting Complexes)

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Open AccessArticle

Synthesis and Evaluation of Selected Benzimidazole Derivatives as Potential Antimicrobial Agents

by Fatmah A. S. Alasmary, Anna M. Snelling, Mohammed E. Zain, Ahmed M. Alafeefy, Amani S. Awaad and Nazira Karodia

Molecules 2015, 20(8), 15206-15223; https://doi.org/10.3390/molecules200815206 - 20 Aug 2015

Cited by 97 | Viewed by 15681

Abstract

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial [...] Read more.

A library of 53 benzimidazole derivatives, with substituents at positions 1, 2 and 5, were synthesized and screened against a series of reference strains of bacteria and fungi of medical relevance. The SAR analyses of the most promising results showed that the antimicrobial activity of the compounds depended on the substituents attached to the bicyclic heterocycle. In particular, some compounds displayed antibacterial activity against two methicillin-resistant Staphylococcus aureus (MRSA) strains with minimum inhibitory concentrations (MICs) comparable to the widely-used drug ciprofloxacin. The compounds have some common features; three possess 5-halo substituents; two are derivatives of (S)-2-ethanaminebenzimidazole; and the others are derivatives of one 2-(chloromethyl)-1H-benzo[d]imidazole and (1H-benzo[d]imidazol-2-yl)methanethiol. The results from the antifungal screening were also very interesting: 23 compounds exhibited potent fungicidal activity against the selected fungal strains. They displayed equivalent or greater potency in their MIC values than amphotericin B. The 5-halobenzimidazole derivatives could be considered promising broad-spectrum antimicrobial candidates that deserve further study for potential therapeutic applications. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessEditorial

Protein-Carbohydrate Interactions, and Beyond …

by Kristof De Schutter and Els J. M. Van Damme

Molecules 2015, 20(8), 15202-15205; https://doi.org/10.3390/molecules200815202 - 20 Aug 2015

Cited by 8 | Viewed by 4797

Abstract

Carbohydrates are ubiquitous and play an intriguing role inside the cell as well as on the cell surface.[...] Full article

(This article belongs to the Special Issue Protein-Carbohydrate Interactions, and Beyond)

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Open AccessArticle

A New Ionone Glycoside and Three New Rhemaneolignans from the Roots of Rehmannia glutinosa

by Meng Li, Xiaolan Wang, Xiaoke Zheng, Jianchao Wang, Wei Zhao, Kai Song, Xuan Zhao, Yanli Zhang, Haixue Kuang and Weisheng Feng

Molecules 2015, 20(8), 15192-15201; https://doi.org/10.3390/molecules200815192 - 20 Aug 2015

Cited by 20 | Viewed by 5494

Abstract

A new ionone glycoside, frehmaglutoside I (1), and three new rhemaneolignans A–C (2–4) were isolated from the 95% EtOH extract of the roots of Rehmannia glutinosa. Their structures were determined by extensive spectroscopic (UV, IR, [...] Read more.

A new ionone glycoside, frehmaglutoside I (1), and three new rhemaneolignans A–C (2–4) were isolated from the 95% EtOH extract of the roots of Rehmannia glutinosa. Their structures were determined by extensive spectroscopic (UV, IR, HR-ESI-MS, 1D and 2D NMR) analyses. In addition, these compounds were evaluated for their protective effects on cardiocytes impaired by doxorubicin in H9c2 cells. Among them, compounds 1–3 exhibited protective effects against DOX-induced cardiotoxicity. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Characterization of the Sublimation and Vapor Pressure of 2-(2-Nitrovinyl) Furan (G-0) Using Thermogravimetric Analysis: Effects of Complexation with Cyclodextrins

by Vivian Ruz, Mirtha Mayra González, Danny Winant, Zenaida Rodríguez and Guy Van den Mooter

Molecules 2015, 20(8), 15175-15191; https://doi.org/10.3390/molecules200815175 - 19 Aug 2015

Cited by 13 | Viewed by 6934

Abstract

In the present work, the sublimation of crystalline solid 2-(2-nitrovinyl) furan (G-0) in the temperature range of 35 to 60 °C (below the melting point of the drug) was studied using thermogravimetric analysis (TGA). The sublimated product was characterized using Fourier-transformed-infrared spectroscopy (FT-IR) [...] Read more.

In the present work, the sublimation of crystalline solid 2-(2-nitrovinyl) furan (G-0) in the temperature range of 35 to 60 °C (below the melting point of the drug) was studied using thermogravimetric analysis (TGA). The sublimated product was characterized using Fourier-transformed-infrared spectroscopy (FT-IR) and thin layer chromatography (TLC). The sublimation rate at each temperature was obtained using the slope of the linear regression model and followed apparent zero-order kinetics. The sublimation enthalpy from 35 to 60 °C was obtained from the Eyring equation. The Gückel method was used to estimate the sublimation rate and vapor pressure at 25 °C. Physical mixtures, kneaded and freeze-dried complexes were prepared with 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) and sulfobutyl ether-β-cyclodextrin (SBE-β-CD) and analyzed using isothermal TGA at 50 °C. The complexation contributed to reducing the sublimation process. The best results were achieved using freeze-dried complexes with both cyclodextrins. Full article

(This article belongs to the Collection Poorly Soluble Drugs)

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Open AccessArticle

Mitochondrial DNA Variation Reveals a Sharp Genetic Break within the Distribution of the Blue Land Crab Cardisoma guanhumi in the Western Central Atlantic

by Maria Rosimere Xavier Amaral, Marc Albrecht, Alan Shane McKinley, Adriana Márcia Ferreira De Carvalho, Severino Cavalcante de Sousa, Júnior and Fabio Mendonça Diniz

Molecules 2015, 20(8), 15158-15174; https://doi.org/10.3390/molecules200815158 - 19 Aug 2015

Cited by 11 | Viewed by 5869

Abstract

The blue land crab Cardisoma guanhumi is widely distributed throughout tropical and subtropical estuarine regions in the Western Central Atlantic (WCA). Patterns of population genetic structure and historical demographics of the species were assessed by mtDNA control region sequence analysis to examine [...] Read more.

The blue land crab Cardisoma guanhumi is widely distributed throughout tropical and subtropical estuarine regions in the Western Central Atlantic (WCA). Patterns of population genetic structure and historical demographics of the species were assessed by mtDNA control region sequence analysis to examine the connectivity among five populations (n = 97) within the region for future conservation strategies and decision-making of fishery management. A total of 234 polymorphic nucleotides were revealed within the sequence region, which have defined 93 distinct haplotypes. No dominant mtDNA haplotypes were found but instead a distribution of a few low-frequency recurrent haplotypes with a large number of singletons. A NJ-tree and a median-joining haplotype network revealed two distinct clusters, corresponding to individuals from estuaries located along the Caribbean Sea and Brazilian waters, respectively. AMOVA and F_ST statistics supported the hypothesis that two main geographic regions exists. Phylogeographical discontinuity was further demonstrated by the Bayesian assignment analysis and a significant pattern of isolation-by-distance. Additionally, tests of neutral evolution and analysis of mismatch distribution indicate a complex demographic history in the WCA, which corresponds to bottleneck and subsequent population growth. Overall, a sharp genetic break between Caribbean and Brazilian populations raised concerns over the conservation status of the blue land crab. Full article

(This article belongs to the Section Molecular Diversity)

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Open AccessArticle

Laccase Gene Expression and Vinasse Biodegradation by Trametes hirsuta Strain Bm-2

by Raúl Tapia-Tussell, Daisy Pérez-Brito, Claudia Torres-Calzada, Alberto Cortés-Velázquez, Liliana Alzate-Gaviria, Rubí Chablé-Villacís and Sara Solís-Pereira

Molecules 2015, 20(8), 15147-15157; https://doi.org/10.3390/molecules200815147 - 19 Aug 2015

Cited by 15 | Viewed by 6183

Abstract

Vinasse is the dark-colored wastewater that is generated by bioethanol distilleries from feedstock molasses. The vinasse that is generated from molasses contains high amounts of pollutants, including phenolic compounds and melanoindin. The goal of this work was to study the expression of laccase [...] Read more.

Vinasse is the dark-colored wastewater that is generated by bioethanol distilleries from feedstock molasses. The vinasse that is generated from molasses contains high amounts of pollutants, including phenolic compounds and melanoindin. The goal of this work was to study the expression of laccase genes in the Trametes hirsuta strain Bm-2, isolated in Yucatan, Mexico, in the presence of phenolic compounds, as well as its effectiveness in removing colorants from vinasse. In the presence of all phenolic compounds tested (guaiacol, ferulic acid, and vanillic acid), increased levels of laccase-encoding mRNA were observed. Transcript levels in the presence of guaiacol were 40 times higher than those in the control. The lcc1 and lcc2 genes of T. hirsuta were differentially expressed; guaiacol and vanillin induced the expression of both genes, whereas ferulic acid only induced the expression of lcc2. The discoloration of vinasse was concomitant with the increase in laccase activity. The highest value of enzyme activity (2543.7 U/mL) was obtained in 10% (v/v) vinasse, which corresponded to a 69.2% increase in discoloration. This study demonstrates the potential of the Bm-2 strain of T. hirsuta for the biodegradation of vinasse. Full article

(This article belongs to the Special Issue Biocatalytic Lignin Modification)

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Open AccessArticle

Porphyrins as Corrosion Inhibitors for N80 Steel in 3.5% NaCl Solution: Electrochemical, Quantum Chemical, QSAR and Monte Carlo Simulations Studies

by Ambrish Singh, Yuanhua Lin, Mumtaz A. Quraishi, Lukman O. Olasunkanmi, Omolola E. Fayemi, Yesudass Sasikumar, Baskar Ramaganthan, Indra Bahadur, Ime B. Obot, Abolanle S. Adekunle, Mwadham M. Kabanda and Eno E. Ebenso

Molecules 2015, 20(8), 15122-15146; https://doi.org/10.3390/molecules200815122 - 18 Aug 2015

Cited by 79 | Viewed by 9161

Abstract

The inhibition of the corrosion of N80 steel in 3.5 wt. % NaCl solution saturated with CO₂ by four porphyrins, namely 5,10,15,20-tetrakis(4-hydroxyphenyl)-21H,23H-porphyrin (HPTB), 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphyrin (T4PP), 4,4′,4″,4‴-(porphyrin-5,10,15,20-tetrayl)tetrakis(benzoic acid) (THP) and 5,10,15,20-tetraphenyl-21H,23H-porphyrin [...] Read more.

The inhibition of the corrosion of N80 steel in 3.5 wt. % NaCl solution saturated with CO₂ by four porphyrins, namely 5,10,15,20-tetrakis(4-hydroxyphenyl)-21H,23H-porphyrin (HPTB), 5,10,15,20-tetra(4-pyridyl)-21H,23H-porphyrin (T4PP), 4,4′,4″,4‴-(porphyrin-5,10,15,20-tetrayl)tetrakis(benzoic acid) (THP) and 5,10,15,20-tetraphenyl-21H,23H-porphyrin (TPP) was studied using electrochemical impedance spectroscopy (EIS), potentiodynamic polarization, scanning electrochemical microscopy (SECM) and scanning electron microscopy (SEM) techniques. The results showed that the inhibition efficiency, η% increases with increasing concentration of the inhibitors. The EIS results revealed that the N80 steel surface with adsorbed porphyrins exhibited non-ideal capacitive behaviour with reduced charge transfer activity. Potentiodynamic polarization measurements indicated that the studied porphyrins acted as mixed type inhibitors. The SECM results confirmed the adsorption of the porphyrins on N80 steel thereby forming a relatively insulated surface. The SEM also confirmed the formation of protective films of the porphyrins on N80 steel surface thereby protecting the surface from direct acid attack. Quantum chemical calculations, quantitative structure activity relationship (QSAR) were also carried out on the studied porphyrins and the results showed that the corrosion inhibition performances of the porphyrins could be related to their E_HOMO, E_LUMO, ω, and μ values. Monte Carlo simulation studies showed that THP has the highest adsorption energy, while T4PP has the least adsorption energy in agreement with the values of σ from quantum chemical calculations. Full article

(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)

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Open AccessArticle

Unconventional Bifunctional Lewis-Brønsted Acid Activation Mode in Bicyclic Guanidine-Catalyzed Conjugate Addition Reactions

by Bokun Cho and Ming Wah Wong

Molecules 2015, 20(8), 15108-15121; https://doi.org/10.3390/molecules200815108 - 18 Aug 2015

Cited by 13 | Viewed by 8082

Abstract

DFT calculations have demonstrated that the unconventional bifunctional Brønsted-Lewis acid activation mode is generally applicable to a range of nucleophilic conjugate additions catalyzed by bicyclic guanidine catalysts. It competes readily with the conventional bifunctional Brønsted acid mode of activation. The optimal pro-nucleophiles for [...] Read more.

DFT calculations have demonstrated that the unconventional bifunctional Brønsted-Lewis acid activation mode is generally applicable to a range of nucleophilic conjugate additions catalyzed by bicyclic guanidine catalysts. It competes readily with the conventional bifunctional Brønsted acid mode of activation. The optimal pro-nucleophiles for this unconventional bifunctional activation are acidic substrates with low pK_a, while the best electrophiles are flexible 1,4-diamide and 1,4-diester conjugated systems. Full article

(This article belongs to the Special Issue Brønsted Base Catalysis in Organic Synthesis)

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Open AccessArticle

Addition of CFCl₃ to Aromatic Aldehydes via in Situ Grignard Reaction

by Balaka Barkakaty, Bandana Talukdar and Bradley S. Lokitz

Molecules 2015, 20(8), 15098-15107; https://doi.org/10.3390/molecules200815098 - 18 Aug 2015

Cited by 1 | Viewed by 7972

Abstract

Synthetic modification of trichlorofluoromethane (CFCl₃) to non-volatile and useful fluorinated precursors is a cost-effective and an environmentally benign strategy for the safe consumption/destruction of the ozone depleting potential of the reagent. In this report, we present a novel method for in [...] Read more.

Synthetic modification of trichlorofluoromethane (CFCl₃) to non-volatile and useful fluorinated precursors is a cost-effective and an environmentally benign strategy for the safe consumption/destruction of the ozone depleting potential of the reagent. In this report, we present a novel method for in situ Grignard reaction using magnesium powder and CFCl₃ for synthesis of dichlorofluoromethyl aromatic alcohols. Full article

(This article belongs to the Special Issue Frontier in Green Chemistry Approaches)

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Open AccessArticle

Phytophthora austrocedri Elicitates Changes in Diterpene Profile of Austrocedrus chilensis

by Verónica Rachel Olate, María Laura Vélez, Alina Greslebin and Guillermo Schmeda-Hirschmann

Molecules 2015, 20(8), 15084-15097; https://doi.org/10.3390/molecules200815084 - 18 Aug 2015

Cited by 2 | Viewed by 6012

Abstract

The populations of the Andean Cupressaceae Austrocedrus chilensis have been severely affected by a disease caused by the phytopathogenic fungus Phytophthora austrocedri. A study was undertaken to disclose changes in the resin composition of P. austrocedri-infected individuals, including naturally infected and [...] Read more.

The populations of the Andean Cupressaceae Austrocedrus chilensis have been severely affected by a disease caused by the phytopathogenic fungus Phytophthora austrocedri. A study was undertaken to disclose changes in the resin composition of P. austrocedri-infected individuals, including naturally infected and artificially inoculated trees, compared with healthy A. chilensis trees. GC-MS and ¹H-NMR studies showed a clear differentiation among healthy and infected resins, with the diterpene isopimara-8(9),15-dien-19-ol as a relevant constituent in resins from infected trees. The effect of resin fractions from P. austrocedri infected trees on the pathogen was assessed by measuring the mycelial growth in agar plates. The most active fractions from resin obtained from infected trees inhibited fungal growth by nearly 50% at 1 mg/dish (35.37 µg/cm²). The main constituent in the active fractions were 18-hydroxymanool and the aldehyde torulosal. Both compounds are oxidation products of manool and can be a chemical response of the tree to the pathogen or be formed from the pathogen as a biotransformation product of manool by microbial oxidation. While the diterpene profiles from A. chilensis tree resins can easily differentiate healthy and P. austrocedri infected individuals, the possible conversion of manool to the antifungal derivatives 4 and 6 by the microorganism remains to be established. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Preformulation Studies of Bee Venom for the Preparation of Bee Venom-Loaded PLGA Particles

by Min-Ho Park, Ju-Heon Kim, Jong-Woon Jeon, Jin-Kyu Park, Bong-Joo Lee, Guk-Hyun Suh and Cheong-Weon Cho

Molecules 2015, 20(8), 15072-15083; https://doi.org/10.3390/molecules200815072 - 18 Aug 2015

Cited by 16 | Viewed by 8233

Abstract

It is known that allergic people was potentially vulnerable to bee venom (BV), which can induce an anaphylactic shock, eventually leading to death. Up until recently, this kind of allergy was treated only by venom immunotherapy (VIT) and its efficacy has been recognized [...] Read more.

It is known that allergic people was potentially vulnerable to bee venom (BV), which can induce an anaphylactic shock, eventually leading to death. Up until recently, this kind of allergy was treated only by venom immunotherapy (VIT) and its efficacy has been recognized worldwide. This treatment is practiced by subcutaneous injections that gradually increase the doses of the allergen. This is inconvenient for patients due to frequent injections. Poly (D,L-lactide-co-glycolide) (PLGA) has been broadly studied as a carrier for drug delivery systems (DDS) of proteins and peptides. PLGA particles usually induce a sustained release. In this study, the physicochemical properties of BV were examined prior to the preparation of BV-loaded PLGA nanoparticles NPs). The content of melittin, the main component of BV, was 53.3%. When protected from the light BV was stable at 4 °C in distilled water, during 8 weeks. BV-loaded PLGA particles were prepared using dichloromethane as the most suitable organic solvent and two min of ultrasonic emulsification time. This study has characterized the physicochemical properties of BV for the preparation BV-loaded PLGA NPs in order to design and optimize a suitable sustained release system in the future. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Antioxidant, Antimicrobial Effects and Phenolic Profile of Lycium barbarum L. Flowers

by Andrei Mocan, Laurian Vlase, Dan Cristian Vodnar, Ana-Maria Gheldiu, Radu Oprean and Gianina Crișan

Molecules 2015, 20(8), 15060-15071; https://doi.org/10.3390/molecules200815060 - 17 Aug 2015

Cited by 27 | Viewed by 6948

Abstract

L. barbarum L. is a widely-accepted nutraceutical presenting highly advantageous nutritive and antioxidant properties. Its flowers have been previously described as a source of diosgenin, β-sitosterol and lanosterol that can be further pharmaceutically developed, but no other data regarding their composition is available. [...] Read more.

L. barbarum L. is a widely-accepted nutraceutical presenting highly advantageous nutritive and antioxidant properties. Its flowers have been previously described as a source of diosgenin, β-sitosterol and lanosterol that can be further pharmaceutically developed, but no other data regarding their composition is available. The purpose of this work was to investigate the chemical constituents, antioxidant and antimicrobial activities of L. barbarum flowers, as an alternative resource of naturally-occurring antioxidant compounds. The free radical scavenging activity of the ethanolic extract was tested by TEAC, two enzymatic assays with more physiological relevance and EPR spectroscopy. The presence of several phenolic compounds, such as chlorogenic, p-coumaric and ferulic acids, but also isoquercitrin, rutin and quercitrin, was assessed by an HPLC/MS method. The antioxidant assays revealed that the extract exhibited a moderate antioxidant potential. The antimicrobial activity was mild against Gram-positive bacteria and lacking against Escherichia coli. These findings complete the scarce existing data and offer new perspectives for further pharmaceutical valorization of L. barbarum flowers. Full article

(This article belongs to the Special Issue Selected papers from the 2nd International Conference on Natural Products Utilization: from Plants to Pharmacy Shelf (ICNPU 2015, Plovdiv, Bulgaria))

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Open AccessArticle

One-Pot Synthesis of Organic-Sulfur-Zinc Hybrid Materials via Polycondensation of a Zinc Salt and Thiols Generated in Situ from Cyclic Dithiocarbonates

by Bungo Ochiai and Hirohisa Konta

Molecules 2015, 20(8), 15049-15059; https://doi.org/10.3390/molecules200815049 - 17 Aug 2015

Cited by 4 | Viewed by 6640

Abstract

Soluble organic-sulfur-zinc hybrid polymers were prepared via a one-pot reaction consisting of ring-opening addition and subsequent polycondensation. The first reaction is the nucleophilic ring-opening addition of 2-ethylhexylamine to multifunctional cyclic dithiocarbonates giving multiple thiols in situ. The sequential polycondensation of the in [...] Read more.

Soluble organic-sulfur-zinc hybrid polymers were prepared via a one-pot reaction consisting of ring-opening addition and subsequent polycondensation. The first reaction is the nucleophilic ring-opening addition of 2-ethylhexylamine to multifunctional cyclic dithiocarbonates giving multiple thiols in situ. The sequential polycondensation of the in situ generated thiols with Zn(OAc)₂ gave the target hybrid polymers. This one-pot method enabled the use of a shorter amine than the previous polycondensation of Zn(OAc)₂ and purified thiols, which required octadecylamine to obtain a soluble product. The obtained hybrid polymers may be cast as composite films with polystyrene and poly(methyl methacrylate). Owing to the shorter alkyl chain, the calculated n_D values of the products (1.60 or 1.61) are higher than that of the previous product bearing octadecyl chains (1.53). Full article

(This article belongs to the Special Issue Ring-Opening Polymerization)

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Open AccessArticle

Inhibition of Cytosolic Phospholipase A2α (cPLA2α) by Medicinal Plants in Relation to Their Phenolic Content

by Eva Arnold, Thorsten Benz, Cornelia Zapp and Michael Wink

Molecules 2015, 20(8), 15033-15048; https://doi.org/10.3390/molecules200815033 - 17 Aug 2015

Cited by 15 | Viewed by 12413

Abstract

The cytosolic phospholipase A₂α(cPLA₂α) is one of the potential targets for anti-inflammatory drugs, since this enzyme plays a key role in the inflammation processes seen in health disorders, like asthma, allergic reactions, arthritis and neuronal diseases. In this study, [...] Read more.

The cytosolic phospholipase A₂α(cPLA₂α) is one of the potential targets for anti-inflammatory drugs, since this enzyme plays a key role in the inflammation processes seen in health disorders, like asthma, allergic reactions, arthritis and neuronal diseases. In this study, cPLA₂α inhibition by 43 methanol extracts from medicinal plants rich in polyphenols was determined. The eight most active extracts were derived from Ribes nigrum (IC50 of 27.7 μg/mL), Ononis spinosa (IC50 of 39.4 μg/mL), Urtica dioica (IC50 of 44.32 μg/mL), Betula sp. (IC50 of 58.02 μg/mL), Sanguisorba officinalis (IC50 of 76.25 μg/mL), Orthosiphon stamineus (IC50 of 78.83 μg/mL), Petasites hybridus (IC50 of 81.02 μg/mL) and Tussilago farfara (IC50 of 123.28 μg/mL). Additionally, the antioxidant activities of these extracts were determined with the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and their phenolic content with the Folin–Ciocalteu reagent. Antioxidant activity showed a non-linear, positive correlation to the phenolic content, but no correlation of PLA2 inhibition with phenolic content could be established. This study provides evidence that cPLA₂αmay be a relevant target for anti-inflammatory agents. Full article

(This article belongs to the Special Issue Proceedings of the the 4th Young Researcher Meeting, Münster, March 13-14, 2015)

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Open AccessArticle

Copper-Catalyzed Dimerization/Cyclization of Itaconates

by Zhiqiang Li, Ruirui Li, Lan Jiang and Zhengning Li

Molecules 2015, 20(8), 15023-15032; https://doi.org/10.3390/molecules200815023 - 17 Aug 2015

Cited by 4 | Viewed by 4574

Abstract

A copper-catalyzed domino reaction between itaconate esters and diethyl zinc (or silane) is developed, affording itaconate dimerization products, multi-ester-substituted cyclopentanones, in moderate to high yields. Full article

(This article belongs to the Section Organic Chemistry)

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755 KiB

Open AccessReview

Ethnomedicinal, Phytochemical and Pharmacological Profile of Anthriscus sylvestris as an Alternative Source for Anticancer Lignans

by Octavian Tudorel Olaru, George Mihai Niţulescu, Alina Orțan and Cristina Elena Dinu-Pîrvu

Molecules 2015, 20(8), 15003-15022; https://doi.org/10.3390/molecules200815003 - 17 Aug 2015

Cited by 29 | Viewed by 9069

Abstract

Anthriscus sylvestris (L.) Hoffm. is a wild herbaceous plant common in most temperate regions. It has been used traditionally to treat headaches, as a tonic, as antitussive, antipyretic, analgesic and diuretic. The plant contains deoxypodophyllotoxin, which is proven to have antitumor and anti-proliferative [...] Read more.

Anthriscus sylvestris (L.) Hoffm. is a wild herbaceous plant common in most temperate regions. It has been used traditionally to treat headaches, as a tonic, as antitussive, antipyretic, analgesic and diuretic. The plant contains deoxypodophyllotoxin, which is proven to have antitumor and anti-proliferative effects, anti-platelet aggregation, antiviral, anti-inflammatory and insecticidal activity. Deoxypodophyllotoxin is considered to be the plant’s most important constituent, because of its pharmacological properties and because it can be converted into epipodophyllotoxin, the main raw material for the semisynthesis of the cytostatic agents etoposide and teniposide. This work summarizes for the first time the results related to the botanical description, distribution and habitat, phytochemical and pharmacological properties and emphasizes the aspects for future biotechnological research to establish its utility in the therapeutic arsenal. Full article

(This article belongs to the Section Natural Products Chemistry)

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Effect of Brewing Duration on the Antioxidant and Hepatoprotective Abilities of Tea Phenolic and Alkaloid Compounds in a t-BHP Oxidative Stress-Induced Rat Hepatocyte Model

by Laura Braud, Ludovic Peyre, Georges De Sousa, Martine Armand, Roger Rahmani and Jean-Michel Maixent

Molecules 2015, 20(8), 14985-15002; https://doi.org/10.3390/molecules200814985 - 17 Aug 2015

Cited by 12 | Viewed by 6772

Abstract

Tea is an interesting source of antioxidants capable of counteracting the oxidative stress implicated in liver diseases. We investigated the impact of antioxidant molecules provided by a mixture of teas’ leaves (green, oolong, pu-erh) after different infusion durations in the prevention of oxidative [...] Read more.

Tea is an interesting source of antioxidants capable of counteracting the oxidative stress implicated in liver diseases. We investigated the impact of antioxidant molecules provided by a mixture of teas’ leaves (green, oolong, pu-erh) after different infusion durations in the prevention of oxidative stress in isolated rat hepatocytes, by comparison with pure epigallocatechin-3-gallate (EGCG), the main representative of tea catechins. Dried aqueous tea extracts (ATE) obtained after 5, 15 and 30 min infusion time were characterized for total polyphenols (gallic acid equivalent), catechins, gallic acid and caffeine (HPLC-DAD/ESI-MS) contents, and for scavenging ability against 2,2-diphenyl-1-picrylhydrazyl free radical. Hepatoprotection was evaluated through hepatocyte viability tests using tert-butyl hydroperoxide as a stress inducer, (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, neutral red uptake, real-time cellular impedance) and mitochondrial function tests. We showed that a 5-min incubation time is sufficient for an optimal bioaccessibility of tea compounds with the highest antioxidative ability, which decreases for longer durations. A 4-h pretreatment of cells with ATE significantly prevented cell death by regulating reactive oxygen species production and maintaining mitochondrial integrity. Pure EGCG, at doses similar in ATE (5–12 µM), was inefficient, suggesting a plausible synergy of several water-soluble tea compounds to explain the ATE beneficial effects. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Fast Identification of Radical Scavengers from Securigera varia by Combining ¹³C-NMR-Based Dereplication to Bioactivity-Guided Fractionation

by Pacôme Sientzoff, Jane Hubert, Coralie Janin, Laurence Voutquenne-Nazabadioko, Jean-Hugues Renault, Jean-Marc Nuzillard, Dominique Harakat and Abdulmagid Alabdul Magid

Molecules 2015, 20(8), 14970-14984; https://doi.org/10.3390/molecules200814970 - 14 Aug 2015

Cited by 17 | Viewed by 7587

Abstract

Securigera varia (Fabaceae) is a common herbaceous perennial plant widely growing in Europe and Asia and purposely established for erosion control, roadside planting, and soil rehabilitation. The aim of this study was to determine the radical scavenging activity of a crude methanol extract [...] Read more.

Securigera varia (Fabaceae) is a common herbaceous perennial plant widely growing in Europe and Asia and purposely established for erosion control, roadside planting, and soil rehabilitation. The aim of this study was to determine the radical scavenging activity of a crude methanol extract of S. varia aerial parts by using the free radical DPPH (1,1-diphenyl-2-picrylhydrazyl) and to rapidly identify the compounds involved in this activity. The crude extract was initially separated in five fractions on Diaion HP20 resin and the most active part was fractionated by Centrifugal Partition Extraction (CPE). Known compounds were directly identified by a ¹³C-NMR-based dereplication method. Semi-preparative high performance liquid chromatography purification experiments were further performed to identify unknown or minor active compounds. As a result, one new (13) and twelve known flavonoid glycosides together with three nitropropanoylglucopyranoses were isolated, including astragalin (1), kaempferol-3-O-(6-O-acetyl)-β-D-glucopyranoside (2), kaempferol-3,4′-di-O-β-D-glucopyranoside (3), trifolin (4), isoquercitrin (5), hyperoside (6), isovitexin (7), isoorientin (8), isovitexin 4′-O-β-D-glucopyranoside (9), apigenin 7-O-β-D-glucuronopyranoside (10), luteolin 7-O-β-D-glucuronopyranoside (11), apigenin 7-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranoside (12), apigenin 7-O-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyranoside (13), 6-O-(3-nitropropanoyl)-β-D-glucopyranoside (14), coronillin (16) and coronarian (15). 120 mg of the most active compound isoorientin against the free radical DPPH was recovered by CPE with an HPLC purity of 99%. Full article

(This article belongs to the Special Issue Applications of Metabolomics within Natural Products Chemistry)

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Open AccessArticle

Inhibitory Activity of Yokukansankachimpihange against Nerve Growth Factor-Induced Neurite Growth in Cultured Rat Dorsal Root Ganglion Neurons

by Chiaki Murayama, Shimpei Watanabe, Motokazu Nakamura and Hisayoshi Norimoto

Molecules 2015, 20(8), 14959-14969; https://doi.org/10.3390/molecules200814959 - 14 Aug 2015

Cited by 7 | Viewed by 6163

Abstract

Chronic pruritus is a major and distressing symptom of many cutaneous diseases, however, the treatment remains a challenge in the clinic. The traditional Chinese-Japanese medicine (Kampo medicine) is a conservative and increasingly popular approach to treat chronic pruritus for both patients and medical [...] Read more.

Chronic pruritus is a major and distressing symptom of many cutaneous diseases, however, the treatment remains a challenge in the clinic. The traditional Chinese-Japanese medicine (Kampo medicine) is a conservative and increasingly popular approach to treat chronic pruritus for both patients and medical providers. Yokukansankachimpihange (YKH), a Kampo formula has been demonstrated to be effective in the treatment of itching of atopic dermatitis in Japan although its pharmacological mechanism is unknown clearly. In an attempt to clarify its pharmacological actions, in this study, we focused on the inhibitory activity of YKH against neurite growth induced with nerve growth factor (NGF) in cultured rat dorsal root ganglion (DRG) neurons because epidermal hyperinnervation is deeply related to itch sensitization. YKH showed approximately 200-fold inhibitory activity against NGF-induced neurite growth than that of neurotropin (positive control), a drug used clinically for treatment of chronic pruritus. Moreover, it also found that Uncaria hook, Bupleurum root and their chemical constituents rhynchophylline, hirsutine, and saikosaponin a, d showed inhibitory activities against NGF-induced neurite growth, suggesting they should mainly contribute to the inhibitory activity of YKH. Further study on the effects of YKH against epidermal nerve density in “itch-scratch” animal models is under investigation. Full article

(This article belongs to the Section Medicinal Chemistry)

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