Molecules

146 KiB

Open AccessCorrection

Hasegawa, T., et al. Structure-Odor Relationships of αSantalol Derivatives with Modified Side Chains. Molecules, 2012, 17, 2259-2270

by Toshio Hasegawa, Hiroaki Izumi, Yuji Tajima and Hideo Yamada

Molecules 2012, 17(9), 11292-11293; https://doi.org/10.3390/molecules170911292 - 21 Sep 2012

Cited by 1 | Viewed by 5547

Abstract

The authors are sorry to report that some of the ¹³C-NMR data reported in their recently published paper [1] were incorrect. While this manuscript was in preparation and pending recording of some ¹³C-NMR spectra the data of α-santalol was used as [...] Read more.

The authors are sorry to report that some of the ¹³C-NMR data reported in their recently published paper [1] were incorrect. While this manuscript was in preparation and pending recording of some ¹³C-NMR spectra the data of α-santalol was used as a placeholder. Upon revising the manuscript according to the reviewers’ comments, they mistakenly thought that all spectral data had been replaced by the correct measured data. Consequently the authors wish to make at this time the following corrections to the paper. [...] Full article

222 KiB

Open AccessArticle

In Vitro Antioxidant Properties of Flavonoids and Polysaccharides Extract from Tobacco (Nicotiana tabacum L.) Leaves

by Qiao-Mei Ru, Li-Juan Wang, Wei-Ming Li, Jing-Lu Wang and Yu-Ting Ding

Molecules 2012, 17(9), 11281-11291; https://doi.org/10.3390/molecules170911281 - 21 Sep 2012

Cited by 43 | Viewed by 10056

Abstract

In the present study, antioxidant properties of flavonoids and polysaccharides from tobacco (Nicotiana tabacum L.) leaves were evaluated in several in vitro systems, e.g., scavenging activities on hydroxyl, superoxide anion, 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radicals, and reducing power. Flavonoids showed [...] Read more.

In the present study, antioxidant properties of flavonoids and polysaccharides from tobacco (Nicotiana tabacum L.) leaves were evaluated in several in vitro systems, e.g., scavenging activities on hydroxyl, superoxide anion, 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radicals, and reducing power. Flavonoids showed much better activity than polysaccharides in scavenging activities on free radicals. When compared to the positive control, ascorbic acid, both showed weaker antioxidant potential. However, flavonoids possessed comparable superoxide anion, DPPH and ABTS radical scavenging abilities to ascorbic acid at high concentration (600 μg/mL). Meanwhile, it was found that flavonoids had prominent effects on the reducing power, which was equivalent to ascorbic acid, and was significantly higher than polysaccharides. These results clearly indicate that flavonoids are effective in scavenging free radicals and have the potential to be powerful antioxidants. Thus, tobacco leaves could be considered as a potential source of natural antioxidants for food, pharmaceutical, cosmetics or nutraceutical industries. Full article

(This article belongs to the Section Natural Products Chemistry)

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222 KiB

Open AccessArticle

Association of KIF6 Variant with Lipid Level and Angiographic Coronary Artery Disease Events Risk in the Han Chinese Population

by Ge Wu, Gui-Bin Li and Bin Dai

Molecules 2012, 17(9), 11269-11280; https://doi.org/10.3390/molecules170911269 - 21 Sep 2012

Cited by 12 | Viewed by 6199

Abstract

KIF6 is a class of molecular motor from the kinesin superfamily. Recently, multiple large studies consisting mainly of Europeans have shown that KIF6 Trp719Arg SNP may be a new predictive factor for coronary artery disease (CAD) event risk. The allelic frequency distribution of [...] Read more.

KIF6 is a class of molecular motor from the kinesin superfamily. Recently, multiple large studies consisting mainly of Europeans have shown that KIF6 Trp719Arg SNP may be a new predictive factor for coronary artery disease (CAD) event risk. The allelic frequency distribution of rs20455 is different in various populations, yet studies among the Han population, one of the largest ethnic groups in the World, have not been conducted. This study is aimed to evaluate the association of KIF6 Trp719Arg variant with angiographic CAD and serum lipid levels in the Han population from northern China. In this case-controlled study, peripheral blood samples were collected from 356 patients and 568 controls of Han Chinese origin. Genotyping was performed by a high-resolution melting curve. The impact of rs20455 on CAD and non-fatal MI was evaluated in a dominant genetic model with stepwise multiple regression analysis. There were no significant differences of genotypes and allele frequency between angiographic CAD and control groups (p > 0.05); however, that of MI and non-MI subgroups were significant differences (p < 0.05). After adjusting for significant risk factors, angiographic CAD risk was not significantly increased in 719Arg allele carriers compared with non-carriers. Further analysis revealed that the non-fatal MI risk and triglyceride levels were significantly higher in 719Arg allele carriers than non-carriers. In conclusion, KIF6 719Arg allele was not an independent risk factor for angiographic CAD susceptibility in Han populations from northern China. However, it was associated with a significantly higher TG level, which may indicate an increased myocardial infarction risk in angiographic CAD patients. Full article

(This article belongs to the Section Medicinal Chemistry)

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265 KiB

Open AccessArticle

Influence of Sample Processing on the Analysis of Carotenoids in Maize

by Sol Rivera and Ramon Canela

Molecules 2012, 17(9), 11255-11268; https://doi.org/10.3390/molecules170911255 - 21 Sep 2012

Cited by 71 | Viewed by 10455

Abstract

We performed a number of tests with the aim to develop an effective extraction method for the analysis of carotenoid content in maize seed. Mixtures of methanol–ethyl acetate (6:4, v/v) and methanol–tetrahydrofuran (1:1, v/v) were the most effective solvent systems for carotenoid extraction [...] Read more.

We performed a number of tests with the aim to develop an effective extraction method for the analysis of carotenoid content in maize seed. Mixtures of methanol–ethyl acetate (6:4, v/v) and methanol–tetrahydrofuran (1:1, v/v) were the most effective solvent systems for carotenoid extraction from maize endosperm under the conditions assayed. In addition, we also addressed sample preparation prior to the analysis of carotenoids by liquid chromatography (LC). The LC response of extracted carotenoids and standards in several solvents was evaluated and results were related to the degree of solubility of these pigments. Three key factors were found to be important when selecting a suitable injection solvent: compatibility between the mobile phase and injection solvent, carotenoid polarity and content in the matrix. Full article

(This article belongs to the Special Issue Carotenoids)

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524 KiB

Open AccessArticle

A Phytoanticipin Derivative, Sodium Houttuyfonate, Induces in Vitro Synergistic Effects with Levofloxacin against Biofilm Formation by Pseudomonas aeruginosa

by Jing Shao, Huijuan Cheng, Changzhong Wang and Yan Wang

Molecules 2012, 17(9), 11242-11254; https://doi.org/10.3390/molecules170911242 - 20 Sep 2012

Cited by 31 | Viewed by 8481

Abstract

Antibiotic resistance has become the main deadly factor in infections, as bacteria can protect themselves by hiding in a self-constructed biofilm. Consequently, more attention is being paid to the search for “non-antibiotic drugs” to solve this problem. Phytoanticipins, the natural antibiotics from plants, [...] Read more.

Antibiotic resistance has become the main deadly factor in infections, as bacteria can protect themselves by hiding in a self-constructed biofilm. Consequently, more attention is being paid to the search for “non-antibiotic drugs” to solve this problem. Phytoanticipins, the natural antibiotics from plants, could be a suitable alternative, but few works on this aspect have been reported. In this study, a preliminary study on the synergy between sodium houttuyfonate (SH) and levofloxacin (LFX) against the biofilm formation of Pseudomonas aeruginosa was performed. The minimal inhibitory concentrations (MIC) of LFX and SH, anti-biofilm formation and synergistic effect on Pseudomonas aeruginosa, and quantification of alginate were determined by the microdilution method, crystal violet (CV) assay, checkerboard method, and hydroxybiphenyl colorimetry. The biofilm morphology of Pseudomonas aeruginosa was observed by fluorescence microscope and scanning electric microscope (SEM). The results showed that: (i) LFX and SH had an obvious synergistic effect against Pseudomonas aeruginosa with MIC values of 0.25 μg/mL and 128 μg/mL, respectively; (ii) ½ × MIC SH combined with 2 × MIC LFX could suppress the biofilm formation of Pseudomonas aeruginosa effectively, with up to 73% inhibition; (iii) the concentration of alginate decreased dramatically by a maximum of 92% after treatment with the combination of antibiotics; and (iv) more dead cells by fluorescence microscope and more removal of extracellular polymeric structure (EPS) by SEM were observed after the combined treatment of LFX and SH. Our experiments demonstrate the promising future of this potent antimicrobial agent against biofilm-associated infections. Full article

(This article belongs to the Section Natural Products Chemistry)

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285 KiB

Open AccessArticle

Bioassay-Guided Isolation and Identification of Cytotoxic Compounds from Gymnosperma glutinosum Leaves

by Ramiro Quintanilla-Licea, Rolando Morado-Castillo, Ricardo Gomez-Flores, Hartmut Laatsch, María Julia Verde-Star, Humberto Hernández-Martínez, Patricia Tamez-Guerra, Reyes Tamez-Guerra and Cristina Rodríguez-Padilla

Molecules 2012, 17(9), 11229-11241; https://doi.org/10.3390/molecules170911229 - 20 Sep 2012

Cited by 18 | Viewed by 8897

Abstract

Bioassay-guided fractionation of hexane extracts of Gymnosperma glutinosum (Asteraceae) leaves, collected in North Mexico, afforded the known compounds hentriacontane (1) and (+)-13S,14R,15-trihydroxy-ent-labd-7-ene (2), as well as the new ent-labdane diterpene (−)-13S [...] Read more.

Bioassay-guided fractionation of hexane extracts of Gymnosperma glutinosum (Asteraceae) leaves, collected in North Mexico, afforded the known compounds hentriacontane (1) and (+)-13S,14R,15-trihydroxy-ent-labd-7-ene (2), as well as the new ent-labdane diterpene (−)-13S,14R,15-trihydroxy-7-oxo-ent-labd-8(9)-ene (3). In addition, D-glycero-D-galactoheptitol (4) was isolated from the methanolic extract of this plant. Their structures were established on the basis of high-field 1D- and 2D NMR methods supported by HR-MS data. The cytotoxic activity was determined by using the in vitro L5178Y-R lymphoma murine model. Hentriacontane (1) and the new ent-labdane 3 showed weak cytotoxicity, whereas the ent-labdane 2 showed significant (p < 0.05) and concentration dependent cytotoxicity (up to 78%) against L5178Y-R cells at concentrations ranging from 7.8 to 250 µg/mL. Full article

(This article belongs to the Section Natural Products Chemistry)

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2612 KiB

Open AccessArticle

Salvianolic Acid A Protects the Peripheral Nerve Function in Diabetic Rats through Regulation of the AMPK-PGC1α-Sirt3 Axis

by Xiaoyan Yu, Li Zhang, Xiuying Yang, Huakang Huang, Zhonglin Huang, Lili Shi, Hengai Zhang and Guanhua Du

Molecules 2012, 17(9), 11216-11228; https://doi.org/10.3390/molecules170911216 - 20 Sep 2012

Cited by 58 | Viewed by 7191

Abstract

Salvianolic acid A (SalA) is one of the main efficacious, water-soluble constituents of Salvia miltiorrhiza Bunge. This study investigated the protective effects of SalA on peripheral nerve in diabetic rats. Administration of SalA (0.3, 1 and 3 mg/kg, ig) was started from the [...] Read more.

Salvianolic acid A (SalA) is one of the main efficacious, water-soluble constituents of Salvia miltiorrhiza Bunge. This study investigated the protective effects of SalA on peripheral nerve in diabetic rats. Administration of SalA (0.3, 1 and 3 mg/kg, ig) was started from the 5th week after strepotozotocin (STZ60 mg/kg) intraperitoneal injection and continued for 8 weeks. Paw withdrawal mechanical threshold (PWMT) and motor nerve conduction velocity (MNCV) were used to assess peripheral nerve function. The western blot methods were employed to test the expression levels of serine-threonine liver kinase B1 (LKB1), AMP-activated protein kinase (AMPK), peroxisome proliferator-activated receptor-gamma coactivator-1alpha (PGC-1α), silent information regulator protein3 (sirtuin 3/Sirt3) and neuronal nitric oxide synthase (nNOS) in sciatic nerve. Results showed that SalA administration could increase PWMT and MNCV in diabetic rats; reduce the deterioration of sciatic nerve pathology; increase AMPK phosphorylation level, up-regulate PGC-1α, Sirt3 and nNOS expression, but had no influence on LKB1. These results suggest that SalA has protective effects against diabetic neuropathy. The beneficial effects of SalA on peripheral nerve function in diabetic rats might be attributed to improvements in glucose metabolism through regulation of the AMPK-PGC1α-Sirt3 axis. Full article

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Open AccessArticle

Physicochemical and Antioxidant Properties of Algerian Honey

by Md. Ibrahim Khalil, Mohammed Moniruzzaman, Laïd Boukraâ, Mokhtar Benhanifia, Md. Asiful Islam, Md. Nazmul Islam, Siti Amrah Sulaiman and Siew Hua Gan

Molecules 2012, 17(9), 11199-11215; https://doi.org/10.3390/molecules170911199 - 20 Sep 2012

Cited by 189 | Viewed by 16162

Abstract

The aim of the present study was to characterize the physical, biochemical and antioxidant properties of Algerian honey samples (n = 4). Physical parameters, such as pH, moisture content, electrical conductivity (EC), total dissolved solids (TDS), color intensity, total sugar and sucrose content [...] Read more.

The aim of the present study was to characterize the physical, biochemical and antioxidant properties of Algerian honey samples (n = 4). Physical parameters, such as pH, moisture content, electrical conductivity (EC), total dissolved solids (TDS), color intensity, total sugar and sucrose content were measured. Several biochemical and antioxidant tests were performed to determine the antioxidant properties of the honey samples. The mean pH was 3.84 ± 0.01, and moisture the content was 13.21 ± 0.16%. The mean EC was 0.636 ± 0.001, and the mean TDS was 316.92 ± 0.92. The mean color was 120.58 ± 0.64 mm Pfund, and the mean 5-hydroxymethylfurfural (HMF) content was 21.49 mg/kg. The mean total sugar and reducing sugar contents were 67.03 ± 0.68 g/mL and 64.72 ± 0.52 g/g, respectively. The mean sucrose content was 2.29 ± 0.65%. High mean values of phenolic (459.83 ± 1.92 mg gallic acid/kg), flavonoid (54.23 ± 0.62 mg catechin/kg), ascorbic acid (159.70 ± 0.78 mg/kg), AEAC (278.15 ± 4.34 mg/kg), protein (3381.83 ± 6.19 mg/kg) and proline (2131.47 ± 0.90) contents, as well as DPPH (39.57% ± 4.18) and FRAP activities [337.77 ± 1.01 µM Fe (II)/100 g], were also detected, indicating that Algerian honey has a high antioxidant potential. Strong positive correlations were found between flavonoid, proline and ascorbic acid contents and color intensity with DPPH and FRAP values. Thus, the present study revealed that Algerian honey is a good source of antioxidants. Full article

(This article belongs to the Section Natural Products Chemistry)

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336 KiB

Open AccessArticle

In Vitro Antioxidant Activity Potential of Lantadene A, a Pentacyclic Triterpenoid of Lantana Plants

by Chong Grace-Lynn, Ibrahim Darah, Yeng Chen, Lachimanan Yoga Latha, Subramanion L. Jothy and Sreenivasan Sasidharan

Molecules 2012, 17(9), 11185-11198; https://doi.org/10.3390/molecules170911185 - 19 Sep 2012

Cited by 27 | Viewed by 6286

Abstract

Lantadenes are pentacyclic triterpenoids present in the leaves of the plant Lantana camara. In the present study, in vitro antioxidant activity and free radical scavenging capacity of lantadene A was evaluated using established in vitro models such as ferric reducing antioxidant power (FRAP), [...] Read more.

Lantadenes are pentacyclic triterpenoids present in the leaves of the plant Lantana camara. In the present study, in vitro antioxidant activity and free radical scavenging capacity of lantadene A was evaluated using established in vitro models such as ferric reducing antioxidant power (FRAP), 2,2-diphenyl-1-picryl-hydrazyl (DPPH•), hydroxyl radical (OH•), nitric oxide radical (NO•), superoxide anion scavenging activities and ferrous ion chelating assay. Interestingly, lantadene A showed considerable in vitro antioxidant, free radical scavenging capacity activities in a dose dependant manner when compared with the standard antioxidant in nitric oxide scavenging, superoxide anion radical scavenging and ferrous ion chelating assay. These findings show that the lantadene A possesses antioxidant activity with different mechanism of actions towards the different free radicals tested. Since lantadene A is a very popular drug in modern medicine, it is a promising candidate for use as an antioxidant and hepatoprotective agent. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents

by Nallely E. Sandoval-Montemayor, Abraham García, Elizabeth Elizondo-Treviño, Elvira Garza-González, Laura Alvarez and María Del Rayo Camacho-Corona

Molecules 2012, 17(9), 11173-11184; https://doi.org/10.3390/molecules170911173 - 19 Sep 2012

Cited by 84 | Viewed by 13590

Abstract

The main aim of this study was to isolate and characterize the active compounds from the hexane extract of the fruit peels of Citrus aurantiifolia, which showed activity against one sensitive and three monoresistant (isoniazid, streptomycin or ethambutol) strains of Mycobacterium tuberculosis [...] Read more.

The main aim of this study was to isolate and characterize the active compounds from the hexane extract of the fruit peels of Citrus aurantiifolia, which showed activity against one sensitive and three monoresistant (isoniazid, streptomycin or ethambutol) strains of Mycobacterium tuberculosis H₃₇Rv. The active extract was fractionated by column chromatography, yielding the following major compounds: 5-geranyloxypsoralen (1); 5-geranyloxy-7-methoxycoumarin (2); 5,7-dimethoxycoumarin (3); 5-methoxypsoralen (4); and 5,8-dimethoxypsoralen (5). The structures of these compounds were elucidated by 1D and 2D NMR spectroscopy. In addition, GC-MS analysis of the hexane extract allowed the identification of 44 volatile compounds, being 5,7-dimethoxycoumarin (15.79%), 3-methyl-1,2-cyclopentanedione (8.27%), 1-methoxy-ciclohexene (8.0%), corylone (6.93%), palmitic acid (6.89%), 5,8-dimethoxypsoralen (6.08%), a-terpineol (5.97%), and umbelliferone (4.36%), the major constituents. Four isolated coumarins and 16 commercial compounds identified by GC-MS were tested against M. tuberculosis H₃₇Rv and three multidrug-resistant M. tuberculosis strains using the Microplate Alamar Blue Assay. The constituents that showed activity against all strains were 5 (MICs = 25–50 mg/mL), 1 (MICs = 50–100 mg/mL), palmitic acid (MICs = 25–50 mg/mL), linoleic acid (MICs = 50–100 mg/mL), oleic acid (MICs = 100 mg/mL), 4-hexen-3-one (MICs = 50–100 mg/mL), and citral (MICs = 50–100 mg/mL). Compound 5 and palmitic acid were the most active ones. The antimycobacterial activity of the hexane extract of C. aurantifolia could be attributed to these compounds. Full article

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226 KiB

Open AccessArticle

Antioxidant Profile of Trifolium pratense L.

by Biljana Kaurinovic, Mira Popovic, Sanja Vlaisavljevic, Heidy Schwartsova and Mirjana Vojinovic-Miloradov

Molecules 2012, 17(9), 11156-11172; https://doi.org/10.3390/molecules170911156 - 18 Sep 2012

Cited by 43 | Viewed by 7881

Abstract

In order to examine the antioxidant properties of five different extracts of Trifolium pratense L. (Leguminosae) leaves, various assays which measure free radical scavenging ability were carried out: 1,1-diphenyl-2-picrylhydrazyl, hydroxyl, superoxide anion and nitric oxide radical scavenger capacity tests and lipid peroxidation assay. [...] Read more.

In order to examine the antioxidant properties of five different extracts of Trifolium pratense L. (Leguminosae) leaves, various assays which measure free radical scavenging ability were carried out: 1,1-diphenyl-2-picrylhydrazyl, hydroxyl, superoxide anion and nitric oxide radical scavenger capacity tests and lipid peroxidation assay. In all of the tests, only the H₂O and (to some extent) the EtOAc extracts showed a potent antioxidant effect compared with BHT and BHA, well-known synthetic antioxidants. In addition, in vivo experiments were conducted with antioxidant systems (activities of GSHPx, GSHR, Px, CAT, XOD, GSH content and intensity of LPx) in liver homogenate and blood of mice after their treatment with extracts of T. pratense leaves, or in combination with CCl₄. Besides, in the extracts examined the total phenolic and flavonoid amounts were also determined, together with presence of the selected flavonoids: quercetin, luteolin, apigenin, naringenin and kaempferol, which were studied using a HPLC-DAD technique. HPLC-DAD analysis showed a noticeable content of natural products according to which the examined Trifolium pratense species could well be regarded as a promising new source of bioactive natural compounds, which can be used both as a food supplement and a remedy. Full article

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210 KiB

Open AccessArticle

Antitrypanosomal Alkaloids from the Marine Bacterium Bacillus pumilus

by Sergio Martínez-Luis, José Félix Gómez, Carmenza Spadafora, Héctor M. Guzmán and Marcelino Gutiérrez

Molecules 2012, 17(9), 11146-11155; https://doi.org/10.3390/molecules170911146 - 18 Sep 2012

Cited by 54 | Viewed by 7192

Abstract

Fractionation of the ethyl acetate extract of the marine bacterium Bacillus pumilus isolated from the black coral Antipathes sp. led to the isolation of five compounds: cyclo-(L-Leu-L-Pro) (1), 3-hydroxyacetylindole (2), N-acetyl-b-oxotryptamine (3 [...] Read more.

Fractionation of the ethyl acetate extract of the marine bacterium Bacillus pumilus isolated from the black coral Antipathes sp. led to the isolation of five compounds: cyclo-(L-Leu-L-Pro) (1), 3-hydroxyacetylindole (2), N-acetyl-b-oxotryptamine (3), cyclo-(L-Phe-L-Pro) (4), and 3-formylindole (5). The structures of compounds 1−5 were established by spectroscopic analyses, including HRESITOF-MS and NMR (¹H, ¹³C, HSQC, HMBC and COSY). Compounds 2, 3 and 5 caused the inhibition on the growth of Trypanosoma cruzi (T. cruzi), with IC₅₀ values of 20.6, 19.4 and 26.9 μM, respectively, with moderate cytotoxicity against Vero cells. Compounds 1−5 were found to be inactive when tested against Plasmodium falciparum and Leishmania donovani, therefore showing selectivity against T. cruzi parasites. Full article

(This article belongs to the Section Natural Products Chemistry)

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184 KiB

Open AccessArticle

Proximate Composition, Nutritional Attributes and Mineral Composition of Peperomia pellucida L. (Ketumpangan Air) Grown in Malaysia

by Der-Jiun Ooi, Shahid Iqbal and Maznah Ismail

Molecules 2012, 17(9), 11139-11145; https://doi.org/10.3390/molecules170911139 - 17 Sep 2012

Cited by 89 | Viewed by 14141

Abstract

This study presents the proximate and mineral composition of Peperomia pellucida L., an underexploited weed plant in Malaysia. Proximate analysis was performed using standard AOAC methods and mineral contents were determined using atomic absorption spectrometry. The results indicated Peperomia pellucida to be rich [...] Read more.

This study presents the proximate and mineral composition of Peperomia pellucida L., an underexploited weed plant in Malaysia. Proximate analysis was performed using standard AOAC methods and mineral contents were determined using atomic absorption spectrometry. The results indicated Peperomia pellucida to be rich in crude protein, carbohydrate and total ash contents. The high amount of total ash (31.22%) suggests a high-value mineral composition comprising potassium, calcium and iron as the main elements. The present study inferred that Peperomia pellucida would serve as a good source of protein and energy as well as micronutrients in the form of a leafy vegetable for human consumption. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Effects of Sorghum [Sorghum bicolor (L.) Moench] Crude Extracts on Starch Digestibility, Estimated Glycemic Index (EGI), and Resistant Starch (RS) Contents of Porridges

by Dilek Lemlioglu-Austin, Nancy D. Turner, Cassandra M. McDonough and Lloyd W. Rooney

Molecules 2012, 17(9), 11124-11138; https://doi.org/10.3390/molecules170911124 - 17 Sep 2012

Cited by 77 | Viewed by 9889

Abstract

Bran extracts (70% aqueous acetone) of specialty sorghum varieties (tannin, black, and black with tannin) were used to investigate the effects of sorghum phenolic compounds on starch digestibility, Estimated Glycemic Index (EGI), and Resistant Starch (RS) of porridges made with normal corn starch, [...] Read more.

Bran extracts (70% aqueous acetone) of specialty sorghum varieties (tannin, black, and black with tannin) were used to investigate the effects of sorghum phenolic compounds on starch digestibility, Estimated Glycemic Index (EGI), and Resistant Starch (RS) of porridges made with normal corn starch, enzyme resistant high amylose corn starch, and ground whole sorghum flours. Porridges were cooked with bran extracts in a Rapid Visco-analyser (RVA). The cooking trials indicated that bran extracts of phenolic-rich sorghum varieties significantly reduced EGI, and increased RS contents of porridges. Thus, there could be potential health benefits associated with the incorporation of phenolic-rich sorghum bran extracts into foods to slow starch digestion and increase RS content. Full article

(This article belongs to the Collection Bioactive Compounds)

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201 KiB

Open AccessArticle

Biological Activity and Safety of Tripterygium Extract Prepared by Sodium Carbonate Extraction

by Wei Fang, Fan Peng, Tao Yi, Cong Zhang, Chunxi Wan, Huibi Xu, Christopher Waikei Lam and Xiangliang Yang

Molecules 2012, 17(9), 11113-11123; https://doi.org/10.3390/molecules170911113 - 17 Sep 2012

Cited by 12 | Viewed by 6654

Abstract

The commercial preparation named “Tripterygium glycosides” prepared by column chromatography has been used for the treatment of inflammatory and autoimmune diseases with significant efficacy but concurrent toxicity. The aim of this study was to reduce the toxicity of Tripterygium extracts, using cytotoxicity [...] Read more.

The commercial preparation named “Tripterygium glycosides” prepared by column chromatography has been used for the treatment of inflammatory and autoimmune diseases with significant efficacy but concurrent toxicity. The aim of this study was to reduce the toxicity of Tripterygium extracts, using cytotoxicity and anti-inflammatory activity of the three principal active components of Tripterygium wilfordii Hook. F. (TWHF) as guiding parameters. Column chromatography was replaced by sodium carbonate extraction for removing the acidic compounds and enriching epoxyditerpenoids and alkaloids in the extract. Results showed that the therapeutic index (IC₅₀/EC₅₀) on murine macrophage Raw 264.7 cells and rat mesangial HBZY-1 cells of the extract prepared by sodium carbonate extraction was significantly higher than that of Tripterygium glycosides (0.8 and 5.2 vs. 0.3 and 2.6, p < 0.05), while its cytotoxicity on human liver HL7702 cells was significantly lower (14.5 ± 1.4 vs. 6.8 ± 0.9, p < 0.05). Further acute oral toxicity experiments showed that the LD₅₀ value of this extract was 1,210 mg/kg compared to 257 mg/kg for Tripterygium glycosides. All the above results suggest that Tripterygium extract prepared by sodium carbonate extraction may represent a potentially optimal source of medicine with good therapeutic index. Full article

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Open AccessCommunication

A 3-D Metal-Organic Framework Constructed with Manganese(ΙΙ), 4,4'-Oxybis(benzoic acid) and 2,2'-Biphenyl: Synthesis, Crystal Structure and Photoelectric Property Characterization

by Kai-Sheng Diao, Long Li, Yu-Qiu Ding and Fu-Hou Lei

Molecules 2012, 17(9), 11103-11112; https://doi.org/10.3390/molecules170911103 - 14 Sep 2012

Cited by 1 | Viewed by 5212

Abstract

Assembly of 4,4'-oxybis(benzoic acid) (H₂L) with manganese chloride in the presence of 2,2'-biphenyl (2,2'-bpy) affords a new coordination polymer [Mn₃L₃(2,2'-bpy)₂]_n (1), in which the [MnL₂]_n layers are extended by [...] Read more.

Assembly of 4,4'-oxybis(benzoic acid) (H₂L) with manganese chloride in the presence of 2,2'-biphenyl (2,2'-bpy) affords a new coordination polymer [Mn₃L₃(2,2'-bpy)₂]_n (1), in which the [MnL₂]_n layers are extended by L bridges resulting in a three-dimensional (3-D) coordination framework. The network structure of 1 has unusual (2,6)-connectivity and represents a new type of (8¹²·12³)(8)(3) topology. These identical and complementary networks are entangled to generate a self-penetrating supramolecular lattice. Moreover, the fluorescence spectrum of 1 exhibits fluorescent emission in the solution of methanol at room temperature. Electrochemical investigation illustrates the electrochemical properties of the title compound. The structure (C₆₂H₄₀Mn₃N₄O₁₅)_n is monoclinic with a = 14.2304(18), b = 17.019(2), c = 25.805(3) Å, α = γ = 90, β = 92.932(2)° and space group C2/c. Full article

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484 KiB

Open AccessArticle

Enhancement of Gene Silencing Effect and Membrane Permeability by Peptide-Conjugated 27-Nucleotide Small Interfering RNA

by Takanori Kubo, Kazuyoshi Yanagihara, Yuichiro Sato, Yasuhiro Morita and Toshio Seyama

Molecules 2012, 17(9), 11089-11102; https://doi.org/10.3390/molecules170911089 - 14 Sep 2012

Cited by 6 | Viewed by 6085

Abstract

Two different sizes of siRNAs, of which one type was 21-nucleotide (nt) siRNA containing 2-nt dangling ends and the other type was 27-nt siRNA with blunt ends, were conjugated with a nuclear export signal peptide of HIV-1 Rev at the 5′-sense end. Processing [...] Read more.

Two different sizes of siRNAs, of which one type was 21-nucleotide (nt) siRNA containing 2-nt dangling ends and the other type was 27-nt siRNA with blunt ends, were conjugated with a nuclear export signal peptide of HIV-1 Rev at the 5′-sense end. Processing by Dicer enzyme, cell membrane permeability, and RNAi efficiency of the peptide-conjugated siRNAs were examined. Dicer cleaved the peptide-conjugated 27-nt siRNA leading to the release of 21-nt siRNA, whereas the peptide-conjugated 21-nt siRNA was not cleaved. High membrane permeability and cytoplasmic localization was found in the conjugates. Moreover, the peptide-conjugated 27-nt siRNA showed increased potency of RNAi in comparison with the nonmodified 21-nt and 27-nt siRNAs, whereas the peptide-conjugated 21-nt siRNA showed decreased RNAi efficacy. This potent RNAi efficacy is probably owing to acceleration of RISC through recognition by Dicer, as well as to the improvement of cell membrane permeability and intracellular accumulation. Full article

(This article belongs to the Special Issue Nucleic Acid Analogs)

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Open AccessArticle

Cyclizations Producing Hydrindanones with Two Methyl Groups at the Juncture Positions Mediated by Samarium Diiodide and Electrolysis

by Masakazu Sono, Natsuko Ise, Tsutomu Shoji and Motoo Tori

Molecules 2012, 17(9), 11079-11088; https://doi.org/10.3390/molecules170911079 - 13 Sep 2012

Cited by 5 | Viewed by 5524

Abstract

One-electron reductive intramolecular cyclization of enones with ketones or aldehydes mediated by samarium diiodide and electrolysis to afford cis-trimethyl- hydrindanolones. The reactions gave selectivities ranging from 1:1 to 100:0 depending on the conditions. Full article

(This article belongs to the Special Issue Challenges in Synthetic Chemistry)

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Open AccessArticle

Primary Investigation of the Preparation of Nanoparticles by Precipitation

by Eliska Vaculikova, Veronika Grunwaldova, Vladimir Kral, Jiri Dohnal and Josef Jampilek

Molecules 2012, 17(9), 11067-11078; https://doi.org/10.3390/molecules170911067 - 13 Sep 2012

Cited by 19 | Viewed by 4936

Abstract

The absorption, distribution, biotransformation and excretion of a drug involve its transport across cell membranes. This process is essential and influenced by the characteristics of the drug, especially its molecular size and shape, solubility at the site of its absorption, relative lipid solubility, [...] Read more.

The absorption, distribution, biotransformation and excretion of a drug involve its transport across cell membranes. This process is essential and influenced by the characteristics of the drug, especially its molecular size and shape, solubility at the site of its absorption, relative lipid solubility, etc. One of the progressive ways for increasing bioavaibility is a nanoparticle preparation technique. Cholesterol, cholestenolone and pregnenolone acetate as model active pharmaceutical ingredients and some of the commonly used excipients as nanoparticle stabilizers were used in the investigated precipitation method that was modified and simplified and can be used as an effective and an affordable technique for the preparation of nanoparticles. All 120 prepared samples were analyzed by means of dynamic light scattering (Nanophox). The range of the particle size of the determined 100 nanoparticle samples was from 1 nm to 773 nm, whereas 82 samples contained nanoparticles of less than 200 nm. Relationships between solvents and used excipients and their amount are discussed. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Chemical Composition and Biological Activities of the Essential Oils from Duguetia lanceolata St. Hil. Barks

by Orlando V. Sousa, Glauciemar Del-Vechio-Vieira, Maria S. Alves, Aílson A. L. Araújo, Míriam A. O. Pinto, Maria P. H. Amaral, Mírian P. Rodarte and Maria A. C. Kaplan

Molecules 2012, 17(9), 11056-11066; https://doi.org/10.3390/molecules170911056 - 13 Sep 2012

Cited by 29 | Viewed by 5742

Abstract

Essential oils of Duguetia lanceolata barks, obtained at 2 (T2) and 4 h (T4), were identified by gas chromatography and gas chromatography/mass spectrometry. β-Elemene (12.7 and 14.9%), caryophyllene oxide (12.4 and 10.7%) and β-selinene (8.4 and 10.4%) were the most abundant components in [...] Read more.

Essential oils of Duguetia lanceolata barks, obtained at 2 (T2) and 4 h (T4), were identified by gas chromatography and gas chromatography/mass spectrometry. β-Elemene (12.7 and 14.9%), caryophyllene oxide (12.4 and 10.7%) and β-selinene (8.4 and 10.4%) were the most abundant components in T2 and T4, respectively. The essential oils inhibited the growth of Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Candida albicans. The essential oils were cytotoxic against brine shrimp. The extraction time influenced the chemical composition and biological activities of essential oils obtained from the barks of D. lanceolata. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Synthesis of Highly Substituted Oxazoles through Iodine(III)-Mediated Reactions of Ketones with Nitriles

by Akio Saito, Nao Hyodo and Yuji Hanzawa

Molecules 2012, 17(9), 11046-11055; https://doi.org/10.3390/molecules170911046 - 13 Sep 2012

Cited by 30 | Viewed by 7776

Abstract

In the presence of trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethane-sulfonyl)imide (Tf₂NH), iodosobenzene (PhI=O) efficiently promoted the reactions of dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions. Full article

(This article belongs to the Special Issue Organic Iodine Chemistry 2012)

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Open AccessArticle

Synthesis and Chromatography-Free Purification of PNA-PEO Conjugates for the Functionalisation of Gold Sensors

by Monica Dettin, Davide Silvestri, Roberta Danesin, Erica Cretaio, Gianluca Picariello, Elisabetta Casarin, Agnese Sonato, Filippo Romanato and Margherita Morpurgo

Molecules 2012, 17(9), 11026-11045; https://doi.org/10.3390/molecules170911026 - 13 Sep 2012

Cited by 10 | Viewed by 6703

Abstract

Peptide Nucleic Acids (PNAs) linked to high molecular weight (MW) poly(ethylene oxide) (PEO) derivatives could be useful conjugates for the direct functionalisation of gold surfaces dedicated to Surface Plasmon Resonance (SPR)-based DNA sensing. However their use is hampered by the difficulty to obtain [...] Read more.

Peptide Nucleic Acids (PNAs) linked to high molecular weight (MW) poly(ethylene oxide) (PEO) derivatives could be useful conjugates for the direct functionalisation of gold surfaces dedicated to Surface Plasmon Resonance (SPR)-based DNA sensing. However their use is hampered by the difficulty to obtain them through a convenient and economical route. In this work we compared three synthetic strategies to obtain PNA-high MW PEO conjugates composed of (a) a 15-mer PNA sequence as the probe complementary to genomic DNA of Mycobacterium tuberculosis, (b) a PEO moiety (2 or 5 KDa MW) and (c) a terminal trityl-protected thiol necessary (after acidic deprotection) for grafting to gold surfaces. The 15-mer PNA was obtained by solid-phase synthesis. Its amino terminal group was later condensed to bi-functional PEO derivatives (2 and 5 KDa MW) carrying a Trt-cysteine at one end and a carboxyl group at the other end. The reaction was carried out either in solution, using HATU or PyOxim as coupling agents, or through the solid-phase approach, with 49.6%, 100% and 5.2% yield, respectively. A differential solvent extraction strategy for product purification without the need for chromatography is described. The ability of the 5 KDa PEO conjugate to function as a probe for complementary DNA detection was demonstrated using a Grating-Coupling Surface Plasmon Resonance (GC-SPR) system. The optimized PEO conjugation and purification protocols are economical and simple enough to be reproduced also within laboratories that are not highly equipped for chemical synthesis. Full article

(This article belongs to the Special Issue Nucleic Acid Analogs)

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Open AccessArticle

Novel Coumarin Derivatives Containing 1,2,4-Triazole, 4,5-Dicyanoimidazole and Purine Moieties: Synthesis and Evaluation of Their Cytostatic Activity

by Krešimir Benci, Leo Mandić, Tomislav Suhina, Mirela Sedić, Marko Klobučar, Sandra Kraljević Pavelić, Krešimir Pavelić, Karlo Wittine and Mladen Mintas

Molecules 2012, 17(9), 11010-11025; https://doi.org/10.3390/molecules170911010 - 12 Sep 2012

Cited by 49 | Viewed by 6962

Abstract

We report here on the synthesis and in vitro anti-tumor effects of a series of novel 1,2,4-triazole (compounds 3–6), 4,5-dicyanoimidazole (compound 7), and purine (compounds 8–13) coumarin derivatives and their acyclic nucleoside analogues 14–18 [...] Read more.

We report here on the synthesis and in vitro anti-tumor effects of a series of novel 1,2,4-triazole (compounds 3–6), 4,5-dicyanoimidazole (compound 7), and purine (compounds 8–13) coumarin derivatives and their acyclic nucleoside analogues 14–18. Structures of novel compounds 3–18 were deduced from their ¹H- and ¹³C-NMR and corresponding mass spectra. Results of anti-proliferative assays performed on a panel of selected human tumor cell lines revealed that compound 6 had moderate cytostatic activity against the HeLa cell line (IC₅₀ = 35 µM), whereas compound 10 showed moderate activity against the HeLa (IC₅₀ = 33 µM), HepG2 (IC₅₀ = 25 µM) and SW620 (IC₅₀ = 35 µM) cell lines. These compounds showed no cytotoxic effects on normal (diploid) human fibroblasts. Full article

(This article belongs to the Section Medicinal Chemistry)

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428 KiB

Open AccessArticle

Inhibition of Cytochrome P450 3A in Rat Liver by the Diorganotin (IV) Compound di-n-Butyl-di-(4-chlorobenzo-hydroxamato)tin (IV) and Its Probable Mechanism

by Yunxia Zhang, Yunlan Li and Qingshan Li

Molecules 2012, 17(9), 10994-11009; https://doi.org/10.3390/molecules170910994 - 12 Sep 2012

Cited by 12 | Viewed by 4663

Abstract

The specific aims of this study were to evaluate the inhibition effect on CYP3A of di-n-butyl-di-(4-chlorobenzohydroxamato)tin (IV) (DBDCT), a tin-based complex with high antitumor activity, and the probable mechanism(s) of this action. Adult male SD rats were treated separately with natural [...] Read more.

The specific aims of this study were to evaluate the inhibition effect on CYP3A of di-n-butyl-di-(4-chlorobenzohydroxamato)tin (IV) (DBDCT), a tin-based complex with high antitumor activity, and the probable mechanism(s) of this action. Adult male SD rats were treated separately with natural saline (NS), lipopolysaccharide (LPS, 5 mg/kg), DBDCT (1.25, 2.5 and 5.0 mg/kg) intraperitoneally for 2 days after induction of CYP3A with dexamethasone (DEX, 100 mg/kg) for 4 days. Western blot analysis and fluorescent quantitation PCR (FQ-PCR) were conducted to determine the changes in expression of CYP3A, PXR, CAR and RXR. The biological accumulation of DBDCT and total Sn were determined by high-performance liquid chromatography (HPLC) and atomic fluorescence spectrometry (AFS). CYP450 content and CYP3A activities were significantly inhibited (p < 0.05) in DBDCT-treated rats compared with the control group, as was the expression of CYP3A (p < 0.05) at both protein and mRNA levels. In DBDCT-treated groups, the expression of PXR protein and mRNA increased, while the expression of CAR decreased. The biological accumulation of DBDCT and Sn in rat livers treated with DBDCT was high. The accumulation of DBDCT and Sn due to the inhibition of CYP3A may be involved in the mechanism of toxicity of DBDCT in rat liver. Full article

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Open AccessArticle

A Structural Study of Epoxidized Natural Rubber (ENR-50) and Its Cyclic Dithiocarbonate Derivative Using NMR Spectroscopy Techniques

by Rosniza Hamzah, Mohamad Abu Bakar, Melati Khairuddean, Issam Ahmed Mohammed and Rohana Adnan

Molecules 2012, 17(9), 10974-10993; https://doi.org/10.3390/molecules170910974 - 12 Sep 2012

Cited by 51 | Viewed by 10476

Abstract

A structural study of epoxidized natural rubber (ENR-50) and its cyclic dithiocarbonate derivative was carried out using NMR spectroscopy techniques. The overlapping ¹H-NMR signals of ENR-50 at δ 1.56, 1.68–1.70, 2.06, 2.15–2.17 ppm were successfully assigned. In this work, the ¹³C-NMR [...] Read more.

A structural study of epoxidized natural rubber (ENR-50) and its cyclic dithiocarbonate derivative was carried out using NMR spectroscopy techniques. The overlapping ¹H-NMR signals of ENR-50 at δ 1.56, 1.68–1.70, 2.06, 2.15–2.17 ppm were successfully assigned. In this work, the ¹³C-NMR chemical shift assignments of ENR-50 were consistent to the previously reported work. A cyclic dithiocarbonate derivative of ENR-50 was synthesized from the reaction of purified ENR-50 with carbon disulfide (CS₂), in the presence of 4-dimethylaminopyridine (DMAP) as catalyst at reflux temperature. The cyclic dithiocarbonate formation involved the epoxide ring opening of the ENR-50. This was followed by insertion of the C–S moiety of CS₂ at the oxygen attached to the quaternary carbon and methine carbon of epoxidized isoprene unit, respectively. The bands due to the C=S and C–O were clearly observed in the FTIR spectrum while the ¹H-NMR spectrum of the derivative revealed the peak attributed to the methylene protons had split. The ¹³C-NMR spectrum of the derivative further indicates two new carbon peaks arising from the >C=S and quaternary carbon of cyclic dithiocarbonate. All other ¹H- and ¹³C-NMR chemical shifts of the derivative remain unchanged with respect to the ENR-50. Full article

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Open AccessEditorial

Steady Impact Factor Growth for MDPI Open Access Journals

by Alexander Thiesen

Molecules 2012, 17(9), 10971-10973; https://doi.org/10.3390/molecules170910971 - 12 Sep 2012

Viewed by 6692

Abstract

For the past three years MDPI has announced the newly released impact factors for its Open Access journals by the means of an annual editorial [1–3]. In 2012 we are—once again—pleased to report that the growth of the impact factors of MDPI’s Open [...] Read more.

For the past three years MDPI has announced the newly released impact factors for its Open Access journals by the means of an annual editorial [1–3]. In 2012 we are—once again—pleased to report that the growth of the impact factors of MDPI’s Open Access journals continues. This year’s edition of the Journal Citation Reports (JCR), which is published annually by Thomson Reuters, includes 10 journals published by MDPI, including three that have received their first official Impact Factors—International Journal of Environmental Research and Public Health (IJERPH), Materials and Nutrients. Table 1 reports the latest Impact Factors for 2011. Figure 1 graphically depicts the evolution of the Impact Factors for four MDPI open access journals that have received Impact Factors in the past. Table 2 reports the ranking of the MDPI journals within the subject categories of the Science Citation Index Expanded (SCIE). [...] Full article

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Open AccessArticle

Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine

by Eduardo Sobarzo-Sánchez, Patricio González Soto, Cristóbal Valdés Rivera, Georgina Sánchez and María Eliana Hidalgo

Molecules 2012, 17(9), 10958-10970; https://doi.org/10.3390/molecules170910958 - 12 Sep 2012

Cited by 17 | Viewed by 6486

Abstract

The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, toxicity and singlet oxygen photosensitization biological properties of isoquinoline alkaloid frameworks. Thus, oxoisoaporphine derivatives 1– [...] Read more.

The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, toxicity and singlet oxygen photosensitization biological properties of isoquinoline alkaloid frameworks. Thus, oxoisoaporphine derivatives 1–5 and 3-azaoxoisoaporphine (6), some of them with phenolic structures, did not present any antioxidant capacity, possibly either by formation of keto-enol tautomerism species or the formation of unstable free radicals. Due to the singlet oxygen quantum yields (F_D) near to unity, and greater photostability than phenalenone, oxoisoaporphines 4–6 may be considered as photosensitizers for singlet oxygen production and can be used as new universal study tools. The biological application as antibacterial agents is an important and possible tool in the study of compounds with low cytotoxicity and high reactivity in antineoplastic chemotherapy. On the other hand, when boldine and its annelated derivatives B1–4 are irradiated, a photoprotector effect is observed (SPF = 2.35), even after 30 minutes of irradiation. They also act as photoprotectors in cell fibroblast cultures. No hemolysis was detected for boldine hydrochloride and its salts without irradiation. In solutions irradiated before incubation (at concentrations over 200 ppm) photoproducts were toxic to the nauplii of Artemia salina. Full article

(This article belongs to the Special Issue Aporphines and Oxoaporphines)

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Open AccessArticle

A Comparative Study of the Characteristics of Cross-Linked, Oxidized and Dual-Modified Rice Starches

by Hua-Xi Xiao, Qin-Lu Lin, Gao-Qiang Liu and Feng-Xiang Yu

Molecules 2012, 17(9), 10946-10957; https://doi.org/10.3390/molecules170910946 - 12 Sep 2012

Cited by 86 | Viewed by 6831

Abstract

Rice starch was cross-linked with epichlorohydrin (0.3%, w/w, on a dry starch basis) and oxidized with sodium hypochlorite (2.5% w/w), respectively. Two dual-modified rice starch samples (oxidized cross-linked rice starch and cross-linked oxidized rice starch) were obtained by the oxidation of cross-linked rice [...] Read more.

Rice starch was cross-linked with epichlorohydrin (0.3%, w/w, on a dry starch basis) and oxidized with sodium hypochlorite (2.5% w/w), respectively. Two dual-modified rice starch samples (oxidized cross-linked rice starch and cross-linked oxidized rice starch) were obtained by the oxidation of cross-linked rice starch and the cross-linking of oxidized rice starch at the same level of reagents. The physicochemical properties of native rice starch, cross-linked rice starch and oxidized rice starch were also studied parallel with those of the two dual-modified rice starch samples using rapid visco analysis (RVA), differential scanning calorimetry (DSC), dynamic rheometry and scanning electron microscopy (SEM). It was found that the levels of cross-linking and oxidation used in this study did not cause any significant changes in the morphology of rice starch granules. Cross-linked oxidized starch showed lower swelling power (SP) and solubility, and higher paste clarity in comparison with native starch. Cross-linked oxidized rice starch also had the lowest tendency of retrogradation and highest ability to resistant to shear compared with native, cross-linked, oxidized and oxidized cross-linked rice starches. These results suggest that the undesirable properties in native, cross-linked and oxidized rice starch samples could be overcome through dual-modification. Full article

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Open AccessArticle

Systematic Study of the Physicochemical Properties of a Homologous Series of Aminobisphosphonates

by Aino-Liisa Alanne, Helena Hyvönen, Manu Lahtinen, Markku Ylisirniö, Petri Turhanen, Erkki Kolehmainen, Sirpa Peräniemi and Jouko Vepsäläinen

Molecules 2012, 17(9), 10928-10945; https://doi.org/10.3390/molecules170910928 - 12 Sep 2012

Cited by 36 | Viewed by 6253

Abstract

Aminobisphosphonates, e.g., alendronate and neridronate, are a well known class of molecules used as drugs for various bone diseases. Although these molecules have been available for decades, a detailed understanding of their most important physicochemical properties under comparable conditions is lacking. In this [...] Read more.

Aminobisphosphonates, e.g., alendronate and neridronate, are a well known class of molecules used as drugs for various bone diseases. Although these molecules have been available for decades, a detailed understanding of their most important physicochemical properties under comparable conditions is lacking. In this study, ten aminobisphosphonates, H₂N(CH₂)_nC(OH)[P(O)(OH)₂]₂, in which n = 2–5, 7–11 and 15 have been synthesized. Their aqueous solubility as a function of temperature and pH, pK_a-values, thermal stability, IR absorptions, and NMR spectral data for bothliquid (¹H, ¹³C, ³¹P-NMR) and solid state (¹³C, ¹⁵N and ³¹P-CPMAS NMR) were determined. Full article

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Open AccessArticle

Antiproliferation and Induction of Apoptosis in Ca9-22 Oral Cancer Cells by Ethanolic Extract of Gracilaria tenuistipitata

by Chi-Chen Yeh, Chao-Neng Tseng, Jing-Iong Yang, Hurng-Wern Huang, Yi Fang, Jen-Yang Tang, Fang-Rong Chang and Hsueh-Wei Chang

Molecules 2012, 17(9), 10916-10927; https://doi.org/10.3390/molecules170910916 - 11 Sep 2012

Cited by 91 | Viewed by 8778

Abstract

The water extract of Gracilaria tenuistipitata have been found to be protective against oxidative stress-induced cellular DNA damage, but the biological function of the ethanolic extracts of G. tenuistipitata (EEGT) is still unknown. In this study, the effect of EEGT on oral squamous [...] Read more.

The water extract of Gracilaria tenuistipitata have been found to be protective against oxidative stress-induced cellular DNA damage, but the biological function of the ethanolic extracts of G. tenuistipitata (EEGT) is still unknown. In this study, the effect of EEGT on oral squamous cell cancer (OSCC) Ca9-22 cell line was examined in terms of the cell proliferation and oxidative stress responses. The cell viability of EEGT-treated OSCC cells was significantly reduced in a dose-response manner (p < 0.0001). The annexin V intensity and pan-caspase activity of EEGT-treated OSCC cells were significantly increased in a dose-response manner (p < 0.05 to 0.0001). EEGT significantly increased the reactive oxygen species (ROS) level (p < 0.0001) and decreased the glutathione (GSH) level (p < 0.01) in a dose-response manner. The mitochondrial membrane potential (MMP) of EEGT-treated OSCC cells was significantly decreased in a dose-response manner (p < 0.005). In conclusion, we have demonstrated that EEGT induced the growth inhibition and apoptosis of OSCC cells, which was accompanied by ROS increase, GSH depletion, caspase activation, and mitochondrial depolarization. Therefore, EEGT may have potent antitumor effect against oral cancer cells. Full article

(This article belongs to the Section Natural Products Chemistry)

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Molecules, Volume 17, Issue 9 (September 2012) – 92 articles , Pages 10000-11293

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