Molecules

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Open AccessRetraction

Retraction: Agarwal et al. Dynamic Action of Carotenoids in Cardioprotection and Maintenance of Cardiac Health, Molecules 2012, 17, 4755-4769

by Derek McPhee

Molecules 2014, 19(3), 3850; https://doi.org/10.3390/molecules19033850 - 25 Mar 2014

Viewed by 7378

Abstract

We were recently alerted by an anonymous tip that at least two paragraphs in the title review [1] appeared to be copied verbatim from papers by other authors without attribution. Upon checking these facts we have established that in addition to the parts [...] Read more.

We were recently alerted by an anonymous tip that at least two paragraphs in the title review [1] appeared to be copied verbatim from papers by other authors without attribution. Upon checking these facts we have established that in addition to the parts brought to our attention, large portions of the review are made up of paragraphs copied verbatim from other reviews or books, sometimes cited, but mostly presented without any references other than to the corresponding original primary literature. Full article

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Open AccessCorrection

Correction: Moharam et al., Inhibitory Effects of Phylligenin and Quebrachitol Isolated from Mitrephora vulpina on Platelet Activating Factor Receptor Binding and Platelet Aggregation. Molecules 2010, 15, 7840-7848

by Bushra Abdulkarim Moharam, Ibrahim Jantan, Juriyati Jalil and Khozirah Shaari

Molecules 2014, 19(3), 3848-3849; https://doi.org/10.3390/molecules19033848 - 24 Mar 2014

Cited by 2 | Viewed by 4976

Abstract

The authors wish to inform readers that there are several minor errors and omissions in the chemical structures shown in Figure 1 of this paper [1]. [...] Full article

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Open AccessArticle

Platinum(II) Oxalato Complexes Involving Adenosine-Based N-Donor Ligands: Synthesis, Characterization and Cytotoxicity Evaluation

by Pavel Štarha, Igor Popa and Zdeněk Trávníček

Molecules 2014, 19(3), 3832-3847; https://doi.org/10.3390/molecules19033832 - 24 Mar 2014

Cited by 10 | Viewed by 6568

Abstract

A one-step synthetic procedure using the reaction of potassium bis(oxalato)platinate(II) with the corresponding N6-benzyladenosine derivative (nL) provided the [Pt(ox)(nL)₂]∙1.5H₂O oxalato (ox) complexes 1–5, involving the nL molecules as monodentate coordinated [...] Read more.

A one-step synthetic procedure using the reaction of potassium bis(oxalato)platinate(II) with the corresponding N6-benzyladenosine derivative (nL) provided the [Pt(ox)(nL)₂]∙1.5H₂O oxalato (ox) complexes 1–5, involving the nL molecules as monodentate coordinated N-donor ligands. The complexes were thoroughly characterized by elemental analysis, multinuclear (¹H, ¹³C, ¹⁵N, ¹⁹⁵Pt) and two dimensional NMR, infrared and Raman spectroscopy, and mass spectrometry, proving their composition and purity as well as coordination of nL through the N7 atom of the purine moiety. Geometry of [Pt(ox)(4FL)₂] (5) was optimized at the B3LYP/LANLTZ/6-311G** level of theory. The complexes were screened for their in vitro cytotoxicity against two human cancer cell lines (HOS osteosarcoma and MCF7 breast adenocarcinoma), but they did not show any effect up to the concentration of 50.0 µM (compounds 1, 2) or 20.0 µM (compounds 3–5). Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Goat Milk Fat Naturally Enriched with Conjugated Linoleic Acid Increased Lipoproteins and Reduced Triacylglycerol in Rats

by Raphaela Rodrigues, Juliana Soares, Hugo Garcia, Claudenice Nascimento, Maria Medeiros, Marco Bomfim, Maria Carmo Medeiros and Rita Queiroga

Molecules 2014, 19(3), 3820-3831; https://doi.org/10.3390/molecules19033820 - 24 Mar 2014

Cited by 10 | Viewed by 6745

Abstract

Goat milk is source of different lipids, including conjugated linoleic acid (CLA). CLA reduces body fat and protect against cardiovascular diseases. In the present study fat from goat milk naturally enriched with CLA was used. Male Wistar rats were divided into three groups [...] Read more.

Goat milk is source of different lipids, including conjugated linoleic acid (CLA). CLA reduces body fat and protect against cardiovascular diseases. In the present study fat from goat milk naturally enriched with CLA was used. Male Wistar rats were divided into three groups that received during a 10 week diet with different lipid sources: soybean oil (CON), coconut oil (CO) and goat milk fat naturally enriched with CLA (GM-CLA). We evaluated the effects of a GM-CLA on biochemistry parameters - high density lipoprotein (HDL), triacylglycerol (TAG), TAG/HDL ratio, total cholesterol and glucose -, body weight and histopathological aspects of the intestine and liver. GM-CLA increased body weight from the second to the fifth week of the experiment compared to CON. Feed intake differed between the CON group and GM-CLA early in the first to third week of the experiments and later between the ninth and tenth week. The CLA-diet group showed increased levels of HDL, reduced levels of TAG and TAG/HDL ratio and no effect on LDL, but enhanced total cholesterol. Serum glucose of the GM-CLA group showed no difference from the control group. Thus, a GM-CLA diet promoted growth in young rats and acted as protector of cardiovascular function, but further studies are still needed to clarify these effects. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Isolation and Characterization of Microsatellite Markers for Cotinus coggygria Scop. (Anacardiaceae) by 454 Pyrosequencing

by Wei Wang, Zhuo Li and Yong Li

Molecules 2014, 19(3), 3813-3819; https://doi.org/10.3390/molecules19033813 - 24 Mar 2014

Cited by 10 | Viewed by 5991

Abstract

Cotinus coggygria Scop. (Anacardiaceae) is a deciduous shrub or small tree that is native to a large area covering from southern Europe, east across central Asia, and the Himalayas in northern China. Shotgun 454 pyrosequencing was used to develop microsatellite markers from the [...] Read more.

Cotinus coggygria Scop. (Anacardiaceae) is a deciduous shrub or small tree that is native to a large area covering from southern Europe, east across central Asia, and the Himalayas in northern China. Shotgun 454 pyrosequencing was used to develop microsatellite markers from the genome of C. coggygria. In this study, 349 microsatellite loci were identified from 40,074 individual sequence reads produced by one-sixteenth run, and primer pairs were designed for these loci. To test the primer amplification efficiency, 50 microsatellite primer pairs were tested across 12 individuals from two C. coggygria populations (Wuzhi Mountain: 36°30'N, 113°39'E; Tianlong Mountain: 37°42'N, 112°26'E). Among the 50 tested primer pairs, eight were found to be polymorphic. The average allele number of the microsatellites was 3.5 per locus, with a range from two to five. The inbreeding coefficient ranged from −0.478 to 0.222. The observed and expected heterozygosities varied from 0.167 to 0.750 and from 0.163 to 0.743, respectively. This set of markers is potentially useful for assessing the genetic diversity, as well as for understanding the population structure and phylogeographical and landscape genetic patterns, of C. coggygria. Full article

(This article belongs to the Section Molecular Diversity)

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Open AccessArticle

Synthesis of All-Z-1,6,9,12,15-Octadecapenten-3-one, A Vinyl Ketone Polyunsaturated Marine Natural Product Isolated from Callysponga sp.

by Anne Marie Langseter, Yngve Stenstrøm and Lars Skattebøl

Molecules 2014, 19(3), 3804-3812; https://doi.org/10.3390/molecules19033804 - 24 Mar 2014

Cited by 8 | Viewed by 6441

Abstract

The synthesis of the marine natural product 1,6Z,9Z,12Z,15Z-octadecapentaen-3-one (1) has been achieved by two different routes starting from the ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively. Using EPA ethyl [...] Read more.

The synthesis of the marine natural product 1,6Z,9Z,12Z,15Z-octadecapentaen-3-one (1) has been achieved by two different routes starting from the ethyl esters of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), respectively. Using EPA ethyl ester as starting material the polyunsaturated vinyl ketone lipid 1 was obtained in 17% overall yield. Full article

(This article belongs to the Special Issue Fatty Acids)

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Open AccessArticle

Antischistosomal Activity of the Terpene Nerolidol

by Marcos P.N. Silva, George L.S. Oliveira, Rusbene B.F. De Carvalho, Damião P. De Sousa, Rivelilson M. Freitas, Pedro L.S. Pinto and Josué De Moraes

Molecules 2014, 19(3), 3793-3803; https://doi.org/10.3390/molecules19033793 - 24 Mar 2014

Cited by 54 | Viewed by 8338

Abstract

Schistosomiasis is a neglected tropical disease that affects hundreds of millions of people worldwide. Since the treatment of this disease currently relies on a single drug, praziquantel, new and safe schistosomicidal agents are urgently required. Nerolidol, a sesquiterpene present in the essential oils [...] Read more.

Schistosomiasis is a neglected tropical disease that affects hundreds of millions of people worldwide. Since the treatment of this disease currently relies on a single drug, praziquantel, new and safe schistosomicidal agents are urgently required. Nerolidol, a sesquiterpene present in the essential oils of several plants, is found in many foods and was approved by the U.S. Food and Drug Administration. In this study we analysed the in vitro antiparasitic effect of nerolidol on Schistosoma mansoni adult worms. Nerolidol at concentrations of 31.2 and 62.5 μM reduced the worm motor activity and caused the death of all male and female schistosomes, respectively. In addition, confocal laser scanning microscopy revealed morphological alterations on the tegument of worms such as disintegration, sloughing and erosion of the surface, and a correlation between viability and tegumental damage was observed. In conclusion, nerolidol may be a promising lead compound for the development of antischistosomal natural agents. Full article

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

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Open AccessArticle

Synthesis, Cytotoxic Activity and 2D-QSAR Study of Some Imidazoquinazoline Derivatives

by Hanan Georgey

Molecules 2014, 19(3), 3777-3792; https://doi.org/10.3390/molecules19033777 - 24 Mar 2014

Cited by 7 | Viewed by 5530

Abstract

A novel series of 4-substituted amino-7,8-dimethoxy-1-phenylimidazo[1,5-a]quinazolin-5(4H)-one derivatives was designed, synthesized and tested for their antitumor activity against a human mammary carcinoma cell line (MCF7). Compound 5a was found to be the most active derivative. Physico-chemical parameters were also determined [...] Read more.

A novel series of 4-substituted amino-7,8-dimethoxy-1-phenylimidazo[1,5-a]quinazolin-5(4H)-one derivatives was designed, synthesized and tested for their antitumor activity against a human mammary carcinoma cell line (MCF7). Compound 5a was found to be the most active derivative. Physico-chemical parameters were also determined and revealed that most of the compounds obeyed the “rule of five” properties with good absorption percentages. 2D-QSAR studies revealed a well predictive and statistically significant and cross validated QSAR model that helps to explore some expectedly potent compounds. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Synthesis and Biological Activity of Some Bile Acid-Based Camptothecin Analogues

by Xingnuo Li, Tengfei Zhao, Dongping Cheng, Chu Chu, Shengqiang Tong, Jizong Yan and Qing-Yong Li

Molecules 2014, 19(3), 3761-3776; https://doi.org/10.3390/molecules19033761 - 24 Mar 2014

Cited by 20 | Viewed by 6768

Abstract

In an effort to decrease the toxicity of camptothecin (CPT) and improve selectivity for hepatoma and colon cancer cells, bile acid groups were introduced into the CPT 20 or 10 positions, resulting in the preparation of sixteen novel CPT-bile acid analogues. The compounds [...] Read more.

In an effort to decrease the toxicity of camptothecin (CPT) and improve selectivity for hepatoma and colon cancer cells, bile acid groups were introduced into the CPT 20 or 10 positions, resulting in the preparation of sixteen novel CPT-bile acid analogues. The compounds in which a bile acid group was introduced at the 20-hydroxyl group of CPT showed better cytotoxic selectivity for human hepatoma and colon cancer cells than for human breast cancer cells. Fluorescence microscopy analysis demonstrated that one compound (E2) entered human hepatoma cells more effectively than it did human breast cancer cells. Compound G4 exhibited the best anti-tumour activity in vivo. These results suggested that introduction of a bile acid group at the 20-position of CPT could decrease toxicity in vivo and improve selectivity for hepatoma cells. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Atomic Model and Micelle Dynamics of QS-21 Saponin

by Conrado Pedebos, Laércio Pol-Fachin, Ramon Pons, Cilâine V. Teixeira and Hugo Verli

Molecules 2014, 19(3), 3744-3760; https://doi.org/10.3390/molecules19033744 - 24 Mar 2014

Cited by 21 | Viewed by 9107

Abstract

QS-21 is a saponin extracted from Quillaja saponaria, widely investigated as a vaccine immunoadjuvant. However, QS-21 use is mainly limited by its chemical instability, significant variety in molecular composition and low tolerance dose in mammals. Also, this compound tends to form micelles [...] Read more.

QS-21 is a saponin extracted from Quillaja saponaria, widely investigated as a vaccine immunoadjuvant. However, QS-21 use is mainly limited by its chemical instability, significant variety in molecular composition and low tolerance dose in mammals. Also, this compound tends to form micelles in a concentration-dependent manner. Here, we aimed to characterize its conformation and the process of micelle formation, both experimentally and computationally. Therefore, molecular dynamics (MD) simulations were performed in systems containing different numbers of QS-21 molecules in aqueous solution, in order to evaluate the spontaneous micelle formation. The applied methodology allowed the generation of micelles whose sizes were shown to be in high agreement with small-angle X-ray scattering (SAXS). Furthermore, the ester linkage between fucose and acyl chain was less solvated in the micellar form, suggesting a reduction in hydrolysis. This is the first atomistic interpretation of previous experimental data, the first micellar characterization of saponin micelles by SAXS and first tridimensional model of a micelle constituted of saponins, contributing to the understanding of the molecular basis of these compounds. Full article

(This article belongs to the Special Issue Oligosaccharides and Glyco-Conjugates)

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Graphical abstract

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Open AccessArticle

Microencapsulation of Purified Amylase Enzyme from Pitaya (Hylocereus polyrhizus) Peel in Arabic Gum-Chitosan using Freeze Drying

by Mehrnoush Amid, Yazid Manap and Nor Khanani Zohdi

Molecules 2014, 19(3), 3731-3743; https://doi.org/10.3390/molecules19033731 - 24 Mar 2014

Cited by 29 | Viewed by 9444

Abstract

Amylase is one of the most important enzymes in the world due to its wide application in various industries and biotechnological processes. In this study, amylase enzyme from Hylocereus polyrhizus was encapsulated for the first time in an Arabic gum-chitosan matrix using freeze [...] Read more.

Amylase is one of the most important enzymes in the world due to its wide application in various industries and biotechnological processes. In this study, amylase enzyme from Hylocereus polyrhizus was encapsulated for the first time in an Arabic gum-chitosan matrix using freeze drying. The encapsulated amylase retained complete biocatalytic activity and exhibited a shift in the optimum temperature and considerable increase in the pH and temperature stabilities compared to the free enzyme. Encapsulation of the enzyme protected the activity in the presence of ionic and non-ionic surfactants and oxidizing agents (H₂O₂) and enhanced the shelf life. The storage stability of amylase is found to markedly increase after immobilization and the freeze dried amylase exhibited maximum encapsulation efficiency value (96.2%) after the encapsulation process. Therefore, the present study demonstrated that the encapsulation of the enzyme in a coating agent using freeze drying is an efficient method to keep the enzyme active and stable until required in industry. Full article

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Open AccessArticle

Discrimination of Dendrobium officinale and Its Common Adulterants by Combination of Normal Light and Fluorescence Microscopy

by Chu Chu, Huimin Yin, Li Xia, Dongping Cheng, Jizhong Yan and Lin Zhu

Molecules 2014, 19(3), 3718-3730; https://doi.org/10.3390/molecules19033718 - 24 Mar 2014

Cited by 18 | Viewed by 8222

Abstract

The stems of Dendrobium officinale Kimura et Migo, named Tie-pi-shi-hu, is one of the most endangered and precious species in China. Because of its various pharmacodynamic effects, D. officinale is widely recognized as a high-quality health food in China and other countries [...] Read more.

The stems of Dendrobium officinale Kimura et Migo, named Tie-pi-shi-hu, is one of the most endangered and precious species in China. Because of its various pharmacodynamic effects, D. officinale is widely recognized as a high-quality health food in China and other countries in south and south-east Asia. With the rising interest of D. officinale, its products have a high price due to a limited supply. This high price has led to the proliferation of adulterants in the market. To ensure the safe use of D. officinale, a fast and convenient method combining normal and fluorescence microscopy was applied in the present study to distinguish D. officinale from three commonly used adulterants including Zi-pi-shi-hu (D. devonianum), Shui-cao-shi-hu (D. aphyllum), Guang-jie-shi-hu (D. gratiosissimum). The result demonstrated that D. officinale could be identified by the characteristic “two hat-shaped” vascular bundle sheath observed under the fluorescence microscopy and the distribution of raphides under normal light microscopy. The other three adulterants could be discriminated by the vascular bundle differences and the distribution of raphides under normal light microscopy. This work indicated that combination of normal light and fluorescence microscopy is a fast and efficient technique to scientifically distinguish D. officinale from the commonly confused species. Full article

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Open AccessArticle

Antiadhesive Properties of Arabinogalactan Protein from Ribes nigrum Seeds against Bacterial Adhesion of Helicobacter pylori

by Jutta Messing, Michael Niehues, Anna Shevtsova, Thomas Borén and Andreas Hensel

Molecules 2014, 19(3), 3696-3717; https://doi.org/10.3390/molecules19033696 - 24 Mar 2014

Cited by 28 | Viewed by 8998

Abstract

Fruit extracts from black currants (Ribes nigrum L.) are traditionally used for treatment of gastritis based on seed polysaccharides that inhibit the adhesion of Helicobacter pylori to stomach cells. For detailed investigations an arabinogalactan protein (F2) was isolated from seeds and characterized [...] Read more.

Fruit extracts from black currants (Ribes nigrum L.) are traditionally used for treatment of gastritis based on seed polysaccharides that inhibit the adhesion of Helicobacter pylori to stomach cells. For detailed investigations an arabinogalactan protein (F2) was isolated from seeds and characterized concerning molecular weight, carbohydrate, amino acid composition, linkage, configuration and reaction with β-glucosyl Yariv. Functional testing of F2 was performed by semiquantitative in situ adhesion assay on sections of human gastric mucosa and by quantitative in vitro adhesion assay with FITC-labled H. pylori strain J99 and human stomach AGS cells. Bacterial adhesins affected were identified by overlay assay with immobilized ligands. ¹²⁵I-radiolabeled F2 served for binding studies to H. pylori and interaction experiments with BabA and SabA. F2 had no cytotoxic effects against H. pylori and AGS cells; but inhibited bacterial binding to human gastric cells. F2 inhibited the binding of BabA and fibronectin-binding adhesin to its specific ligands. Radiolabeled F2 bound non-specifically to different strains of H. pylori; and to BabA deficient mutant. F2 did not lead to subsequent feedback regulation or increased expression of adhesins or virulence factors. From these data the non-specific interactions between F2 and the H. pylori lead to moderate antiadhesive effects. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Rooibos Flavonoids Inhibit the Activity of Key Adrenal Steroidogenic Enzymes, Modulating Steroid Hormone Levels in H295R Cells

by Lindie Schloms and Amanda C. Swart

Molecules 2014, 19(3), 3681-3695; https://doi.org/10.3390/molecules19033681 - 24 Mar 2014

Cited by 22 | Viewed by 8371

Abstract

Major rooibos flavonoids—dihydrochalcones, aspalathin and nothofagin, flavones—orientin and vitexin, and a flavonol, rutin, were investigated to determine their influence on the activity of adrenal steroidogenic enzymes, 3β-hydroxysteroid dehydrogenase (3βHSD2) and cytochrome P450 (P450) enzymes, P450 17α-hydroxylase/17,20-lyase (CYP17A1), P450 21-hydroxylase (CYP21A2) and P450 11β-hydroxylase [...] Read more.

Major rooibos flavonoids—dihydrochalcones, aspalathin and nothofagin, flavones—orientin and vitexin, and a flavonol, rutin, were investigated to determine their influence on the activity of adrenal steroidogenic enzymes, 3β-hydroxysteroid dehydrogenase (3βHSD2) and cytochrome P450 (P450) enzymes, P450 17α-hydroxylase/17,20-lyase (CYP17A1), P450 21-hydroxylase (CYP21A2) and P450 11β-hydroxylase (CYP11B1). All the flavonoids inhibited 3βHSD2 and CYP17A1 significantly, while the inhibition of downstream enzymes, CYP21A2 and CYP11B1, was both substrate and flavonoid specific. The dihydrochalcones inhibited the activity of CYP21A2, but not that of CYP11B1. Although rutin, orientin and vitexin inhibited deoxycortisol conversion by CYP11B1 significantly, inhibition of deoxycorticosterone was <20%. These three flavonoids were unable to inhibit CYP21A2, with negligible inhibition of deoxycortisol biosynthesis only. Rooibos inhibited substrate conversion by CYP17A1 and CYP21A2, while the inhibition of other enzyme activities was <20%. In H295R cells, rutin had the greatest inhibitory effect on steroid production upon forskolin stimulation, reducing total steroid output 2.3-fold, while no effect was detected under basal conditions. Nothofagin and vitexin had a greater inhibitory effect on overall steroid production compared to aspalathin and orientin, respectively. The latter compounds contain two hydroxyl groups on the B ring, while nothofagin and vitexin contain a single hydroxyl group. In addition, all of the flavonoids are glycosylated, albeit at different positions—dihydrochalcones at C3' and flavones at C8 on ring A, while rutin, a larger molecule, has a rutinosyl moiety at C3 on ring C. Structural differences regarding the number and position of hydroxyl and glucose moieties as well as structural flexibility could indicate different mechanisms by which these flavonoids influence the activity of adrenal steroidogenic enzymes. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Flavonoids)

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Open AccessArticle

Additional New Minor Cucurbitane Glycosides from Siraitia grosvenorii

by Indra Prakash and Venkata Sai Prakash Chaturvedula

Molecules 2014, 19(3), 3669-3680; https://doi.org/10.3390/molecules19033669 - 24 Mar 2014

Cited by 14 | Viewed by 7162

Abstract

Continuous phytochemical studies of the crude extract of Luo Han Guo (Siraitia grosvenorii) furnished three additional new cucurbitane triterpene glycosides, namely 11-deoxymogroside V, 11-deoxyisomogroside V, and 11-deoxymogroside VI. The structures of all the isolated compounds were characterized on the basis of [...] Read more.

Continuous phytochemical studies of the crude extract of Luo Han Guo (Siraitia grosvenorii) furnished three additional new cucurbitane triterpene glycosides, namely 11-deoxymogroside V, 11-deoxyisomogroside V, and 11-deoxymogroside VI. The structures of all the isolated compounds were characterized on the basis of extensive NMR and mass spectral data as well as hydrolysis studies. The complete ¹H- and ¹³C-NMR spectral assignments of the three unknown compounds are reported for the first time based on COSY, TOCSY, HSQC, and HMBC spectroscopic data. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Artichoke, Cynarin and Cyanidin Downregulate the Expression of Inducible Nitric Oxide Synthase in Human Coronary Smooth Muscle Cells

by Ning Xia, Andrea Pautz, Ursula Wollscheid, Gisela Reifenberg, Ulrich Förstermann and Huige Li

Molecules 2014, 19(3), 3654-3668; https://doi.org/10.3390/molecules19033654 - 24 Mar 2014

Cited by 33 | Viewed by 11991

Abstract

Artichoke (Cynara scolymus L.) is one of the world’s oldest medicinal plants with multiple health benefits. We have previously shown that artichoke leaf extracts and artichoke flavonoids upregulate the gene expression of endothelial-type nitric oxide synthase (eNOS) in human endothelial cells. Whereas [...] Read more.

Artichoke (Cynara scolymus L.) is one of the world’s oldest medicinal plants with multiple health benefits. We have previously shown that artichoke leaf extracts and artichoke flavonoids upregulate the gene expression of endothelial-type nitric oxide synthase (eNOS) in human endothelial cells. Whereas NO produced by the eNOS is a vasoprotective molecule, NO derived from the inducible iNOS plays a pro-inflammatory role in the vasculature. The present study was aimed to investigate the effects of artichoke on iNOS expression in human coronary artery smooth muscle cells (HCASMC). Incubation of HCASMC with a cytokine mixture led to an induction of iNOS mRNA expression. This iNOS induction was concentration- and time-dependently inhibited by an artichoke leaf extract (1–100 µg/mL, 6 h or 24 h). Consistently, the artichoke leaf extract also reduced cytokine-induced iNOS promoter activation and iNOS protein expression. In addition, treatment of HCASMC with four well-known artichoke compounds (cynarin > cyanidin > luteolin ≈ cynaroside) led to a downregulation iNOS mRNA and protein expression, with cynarin being the most potent one. In conclusion, artichoke contains both eNOS-upregulating and iNOS-downregulating compounds. Such compounds may contribute to the beneficial effects of artichoke and may per se have therapeutic potentials. Full article

(This article belongs to the Special Issue Biosynthesis and Biotransformation)

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Open AccessArticle

Synthesis of New 1,2,3-Triazol-4-yl-quinazoline Nucleoside and Acyclonucleoside Analogues

by Abdelaaziz Ouahrouch, Moha Taourirte, Joachim W. Engels, Soumaya Benjelloun and Hassan B. Lazrek

Molecules 2014, 19(3), 3638-3653; https://doi.org/10.3390/molecules19033638 - 24 Mar 2014

Cited by 25 | Viewed by 8333

Abstract

In this study, we describe the synthesis of 1,4-disustituted-1,2,3-triazolo-quinazoline ribonucleosides or acyclonucleosides by means of 1,3-dipolar cycloaddition between various O or N-alkylated propargyl-quinazoline and 1'-azido-2',3',5'-tri-O-benzoylribose or activated alkylating agents under microwave conditions. None of the compounds selected showed significant anti-HCV [...] Read more.

In this study, we describe the synthesis of 1,4-disustituted-1,2,3-triazolo-quinazoline ribonucleosides or acyclonucleosides by means of 1,3-dipolar cycloaddition between various O or N-alkylated propargyl-quinazoline and 1'-azido-2',3',5'-tri-O-benzoylribose or activated alkylating agents under microwave conditions. None of the compounds selected showed significant anti-HCV activity in vitro. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessCommunication

Entrapment of Probiotics in Water Extractable Arabinoxylan Gels: Rheological and Microstructural Characterization

by Adriana Morales-Ortega, Elizabeth Carvajal-Millan, Francisco Brown-Bojorquez, Agustín Rascón-Chu, Patricia Torres-Chavez, Yolanda L. López-Franco, Jaime Lizardi-Mendoza, Ana L. Martínez-López and Alma C. Campa-Mada

Molecules 2014, 19(3), 3628-3637; https://doi.org/10.3390/molecules19033628 - 24 Mar 2014

Cited by 23 | Viewed by 7209

Abstract

Due to their porous structure, aqueous environment and dietary fiber nature arabinoxylan (AX) gels could have potential applications for colon-specific therapeutic molecule delivery. In addition, prebiotic and health related effects of AX have been previously demonstrated. It has been also reported that cross-linked [...] Read more.

Due to their porous structure, aqueous environment and dietary fiber nature arabinoxylan (AX) gels could have potential applications for colon-specific therapeutic molecule delivery. In addition, prebiotic and health related effects of AX have been previously demonstrated. It has been also reported that cross-linked AX can be degraded by bacteria from the intestinal microbiota. However, AX gels have not been abundantly studied as carrier systems and there is no information available concerning their capability to entrap cells. In this regard, probiotic bacteria such as Bifidobacterium longum have been the focus of intense research activity lately. The objective of this research was to investigate the entrapment of probiotic B. longum in AX gels. AX solution at 2% (w/v) containing B. longum (1 × 10⁷ CFU/cm) formed gels induced by laccase as cross-linking agent. The entrapment of B. longum decreased gel elasticity from 31 to 23 Pa, probably by affecting the physical interactions taking place between WEAX chains. Images of AX gels containing B. longum viewed under a scanning electron microscope show the gel network with the bacterial cells entrapped inside. The microstructure of these gels resembles that of an imperfect honeycomb. The results suggest that AX gels can be potential candidates for the entrapment of probiotics. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Trigocherrierin A, a Potent Inhibitor of Chikungunya Virus Replication

by Mélanie Bourjot, Pieter Leyssen, Johan Neyts, Vincent Dumontet and Marc Litaudon

Molecules 2014, 19(3), 3617-3627; https://doi.org/10.3390/molecules19033617 - 24 Mar 2014

Cited by 46 | Viewed by 8780

Abstract

Trigocherrierin A (1) and trigocherriolide E (2), two new daphnane diterpenoid orthoesters (DDOs), and six chlorinated analogues, trigocherrins A, B, F and trigocherriolides A–C, were isolated from the leaves of Trigonostemon cherrieri. Their structures were identified by mass [...] Read more.

Trigocherrierin A (1) and trigocherriolide E (2), two new daphnane diterpenoid orthoesters (DDOs), and six chlorinated analogues, trigocherrins A, B, F and trigocherriolides A–C, were isolated from the leaves of Trigonostemon cherrieri. Their structures were identified by mass spectrometry, extensive one- and two-dimensional NMR spectroscopy and through comparison with data reported in the literature. These compounds are potent and selective inhibitors of chikungunya virus (CHIKV) replication. Among the DDOs isolated, compound 1 exhibited the strongest anti-CHIKV activity (EC₅₀ = 0.6 ± 0.1 µM, SI = 71.7). Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Antimicrobial Activities against Periodontopathic Bacteria of Pittosporum tobira and Its Active Compound

by Jung-Hyun Oh, Yong Joon Jeong, Hyun Jung Koo, Dae Won Park, Se Chan Kang, Hoang Viet Bach Khoa, Le Ba Le, Joon Hyeong Cho and Jin-Yong Lee

Molecules 2014, 19(3), 3607-3616; https://doi.org/10.3390/molecules19033607 - 24 Mar 2014

Cited by 10 | Viewed by 7928

Abstract

The study of medicinal plants for treatment of periodontitis is of great value to establish their efficacy as sources of new antimicrobial drugs. Five hundred and fifty eight Korean local plant extracts were screened for antibacterial activity against representative periodontopathic bacteria such as [...] Read more.

The study of medicinal plants for treatment of periodontitis is of great value to establish their efficacy as sources of new antimicrobial drugs. Five hundred and fifty eight Korean local plant extracts were screened for antibacterial activity against representative periodontopathic bacteria such as Porphyromonas gingivalis, Prevotella intermedia, and Fusobacterium nucleatum. Among the various medicinal plants, the alcohol extract of Pittosporum tobira, which significantly exhibited antibacterial effect for all tested strains, showed the highest activity in the antimicrobial assays. NMR analyses revealed that R1-barrigenol, a triterpene sapogenin, was the most effective compound in P. tobira. These results demonstrated that P. tobira possesses antimicrobial properties and would be beneficial for the prevention and treatment of periodontitis. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Synthesis and Properties of a Lacquer Wax-Based Quarternary Ammonium Gemini Surfactant

by Hongxia Chen, Chengzhang Wang, Jianzhong Ye, Hao Zhou, Li Lu and Zhibing Yang

Molecules 2014, 19(3), 3596-3606; https://doi.org/10.3390/molecules19033596 - 24 Mar 2014

Cited by 10 | Viewed by 6979

Abstract

Lacquer wax is an important fatty resource obtained from the mesocarp of the berries of Toxicodendron vernicifluum. In order to expand the applications of lacquer wax, we hydrolyzed it after establishing the best conditions for the acid-catalyzed hydrolysis using a Box-Behnken design. [...] Read more.

Lacquer wax is an important fatty resource obtained from the mesocarp of the berries of Toxicodendron vernicifluum. In order to expand the applications of lacquer wax, we hydrolyzed it after establishing the best conditions for the acid-catalyzed hydrolysis using a Box-Behnken design. Then we synthesized a quarternary ammonium gemini surfactant by a three-step reaction. The surface properties of an aqueous solution of the final product were investigated. The optimum conditions were 9% catalyst, 100 °C of reaction temperature and 14 h of reaction time, while the maximum free fatty acids (FFA)% was 99.67%. From the gas chromatography, the main fatty acids of the lacquer wax were palmitic, oleic and octadecanoic acid. The lacquer wax gemini surfactant was synthesized, and its structure was confirmed by IR and NMR. The experiments showed that the critical micelle concentration (CMC) is 5 × 10⁻⁴ mol·L⁻¹, the surface tension is 33.6 mN·m⁻¹. When the content of surfactant was 0.1%, the separation time of 5 mL water was 10 min. Full article

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Open AccessReview

Structure-Activity Association of Flavonoids in Lung Diseases

by João Henrique G. Lago, Alessandra C. Toledo-Arruda, Márcia Mernak, Kaidu H. Barrosa, Milton A. Martins, Iolanda F. L. C. Tibério and Carla M. Prado

Molecules 2014, 19(3), 3570-3595; https://doi.org/10.3390/molecules19033570 - 24 Mar 2014

Cited by 130 | Viewed by 17430

Abstract

Flavonoids are polyphenolic compounds classified into flavonols, flavones, flavanones, isoflavones, catechins, anthocyanidins, and chalcones according to their chemical structures. They are abundantly found in Nature and over 8,000 flavonoids have from different sources, mainly plant materials, have been described. Recently reports have shown [...] Read more.

Flavonoids are polyphenolic compounds classified into flavonols, flavones, flavanones, isoflavones, catechins, anthocyanidins, and chalcones according to their chemical structures. They are abundantly found in Nature and over 8,000 flavonoids have from different sources, mainly plant materials, have been described. Recently reports have shown the valuable effects of flavonoids as antiviral, anti-allergic, antiplatelet, antitumor, antioxidant, and anti-inflammatory agents and interest in these compounds has been increasing since they can be helpful to human health. Several mechanisms of action are involved in the biological properties of flavonoids such as free radical scavenging, transition metal ion chelation, activation of survival genes and signaling pathways, regulation of mitochondrial function and modulation of inflammatory responses. The anti-inflammatory effects of flavonoids have been described in a number of studies in the literature, but not frequently associated to respiratory disease. Thus, this review aims to discuss the effects of different flavonoids in the control of lung inflammation in some disorders such as asthma, lung emphysema and acute respiratory distress syndrome and the possible mechanisms of action, as well as establish some structure-activity relationships between this biological potential and chemical profile of these compounds. Full article

(This article belongs to the Special Issue Structure-Activity Relationship of Flavonoids)

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Open AccessArticle

Protein-Rich Fraction of Cnidoscolus urens (L.) Arthur Leaves: Enzymatic Characterization and Procoagulant and Fibrinogenolytic Activities

by Yamara A. S. De Menezes, Juliana Félix-Silva, Arnóbio A. Da Silva-Júnior, Ivanise M. M. Rebecchi, Adeliana S. De Oliveira, Adriana F. Uchoa and Matheus De F. Fernandes-Pedrosa

Molecules 2014, 19(3), 3552-3569; https://doi.org/10.3390/molecules19033552 - 21 Mar 2014

Cited by 17 | Viewed by 7915

Abstract

Proteolytic enzymes are important macromolecules in the regulation of biochemical processes in living organisms. Additionally, these versatile biomolecules have numerous applications in the industrial segment. In this study we have characterized a protein-rich fraction of Cnidoscolus urens (L.) Arthur leaves, rich in proteolytic [...] Read more.

Proteolytic enzymes are important macromolecules in the regulation of biochemical processes in living organisms. Additionally, these versatile biomolecules have numerous applications in the industrial segment. In this study we have characterized a protein-rich fraction of Cnidoscolus urens (L.) Arthur leaves, rich in proteolytic enzymes, and evaluated its effects on the coagulation cascade. Three protein-rich fractions were obtained from the crude extract of C. urens leaves by precipitation with acetone. Fraction F1.0 showed higher proteolytic activity upon azocasein, and thus, was chosen for subsequent tests. The proteolytic activity of F1.0 on fibrinogen was dose-dependent and time-dependent. The extract demonstrated procoagulant activity on citrated plasma and reduced the APTT, not exerting effects on PT. Despite the fibrin(ogen)olytic activity, F1.0 showed no defibrinogenating activity in vivo. The fraction F1.0 did not express hemorrhagic nor hemolytic activities. The proteolytic activity was inhibited by E-64, EDTA and in the presence of metal ions, and increased when pretreated with reducing agents, suggesting that the observed activity was mostly due to cysteine proteases. Several bands with proteolytic activity were detected by zymography with gelatin, albumin and fibrinogen. The optimal enzymatic activity was observed in temperature of 60 °C and pH 5.0, demonstrating the presence of acidic proteases. In conclusion, these results could provide basis for the pharmacological application of C. urens proteases as a new source of bioactive molecules to treat bleeding and thrombotic disorders. Full article

(This article belongs to the Section Natural Products Chemistry)

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Open AccessArticle

Design, Synthesis and SAR Study of Novel Trisubstituted Pyrimidine Amide Derivatives as CCR4 Antagonists

by Libao Xu, Yang Zhang, Wenjie Dai, Ying Wang, Dan Jiang, Lili Wang, Junhai Xiao, Xiaohong Yang and Song Li

Molecules 2014, 19(3), 3539-3551; https://doi.org/10.3390/molecules19033539 - 21 Mar 2014

Cited by 7 | Viewed by 7462

Abstract

The design, synthesis and structure-activity relationship studies of some novel trisubstituted pyrimidine amide derivatives prepared as CCR4 antagonists are described. The activities of these compounds were evaluated by the CCR4-MDC chemotaxis inhibition assay. Compound 1, which we have previously reported as a [...] Read more.

The design, synthesis and structure-activity relationship studies of some novel trisubstituted pyrimidine amide derivatives prepared as CCR4 antagonists are described. The activities of these compounds were evaluated by the CCR4-MDC chemotaxis inhibition assay. Compound 1, which we have previously reported as a potent antagonist of CCR4, was employed as the positive control. The results indicated that most of the synthesized compounds exhibited some chemotaxis inhibition activity against CCR4. Of these new compounds, compounds 6c, 12a and 12b, with IC₅₀values of 0.064, 0.077 and 0.069 μM, respectively, showed higher or similar activity compared with compound 1 (IC₅₀ of 0.078 μM). These compounds provide a basis for further structural modifications. The systematic structure-activity relationship of these trisubstituted pyrimidine amide derivatives was discussed based on the obtained experimental data. The results from the SAR study may be useful for identifying more potent CCR4 antagonists. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Structure-Activity Relationship Study of Sesquiterpene Lactones and Their Semi-Synthetic Amino Derivatives as Potential Antitrypanosomal Products

by Stefanie Zimmermann, Gerda Fouché, Maria De Mieri, Yukiko Yoshimoto, Toyonobu Usuki, Rudzani Nthambeleni, Christopher J. Parkinson, Christiaan Van der Westhuyzen, Marcel Kaiser, Matthias Hamburger and Michael Adams

Molecules 2014, 19(3), 3523-3538; https://doi.org/10.3390/molecules19033523 - 21 Mar 2014

Cited by 32 | Viewed by 8973

Abstract

Sesquiterpene lactones (STLs) are natural products that have potent antitrypanosomal activity in vitro and, in the case of cynaropicrin, also reduce parasitemia in the murine model of trypanosomiasis. To explore their structure-antitrypanosomal activity relationships, a set of 34 natural and semi-synthetic STLs and [...] Read more.

Sesquiterpene lactones (STLs) are natural products that have potent antitrypanosomal activity in vitro and, in the case of cynaropicrin, also reduce parasitemia in the murine model of trypanosomiasis. To explore their structure-antitrypanosomal activity relationships, a set of 34 natural and semi-synthetic STLs and amino-STLs was tested in vitro against T. b. rhodesiense (which causes East African sleeping sickness) and mammalian cancer cells (rat bone myoblast L6 cells). It was found that the α-methylene-γ-lactone moiety is necessary for both antitrypanosomal effects and cytotoxicity. Antitrypanosomal selectivity is facilitated by 2-(hydroxymethyl)acrylate or 3,4-dihydroxy-2-methylenebutylate side chains, and by the presence of cyclopentenone rings. Semi-synthetic STL amines with morpholino and dimethylamino groups showed improved in vitro activity over the native STLs. The dimethylamino derivative of cynaropicrin was prepared and tested orally in the T. b. rhodesiense acute mouse model, where it showed reduced toxicity over cynaropicrin, but also lost antitrypanosomal activity. Full article

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

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Open AccessArticle

Celastrol Induces Apoptosis in Gefitinib-Resistant Non-Small Cell Lung Cancer Cells via Caspases-Dependent Pathways and Hsp90 Client Protein Degradation

by Xing-Xing Fan, Na Li, Jian-Lin Wu, Yan-Ling Zhou, Jian-Xing He, Liang Liu and Elaine Lai-Han Leung

Molecules 2014, 19(3), 3508-3522; https://doi.org/10.3390/molecules19033508 - 21 Mar 2014

Cited by 41 | Viewed by 9137

Abstract

Celastrol, a triterpene extracted from the Chinese herb Tripterygium wilfordii, has been shown to have multiple bioactivities. Although among these activities, its anti-cancer effects have attracted the most attention, the effect of celastrol on gefitinib-resistant non-small cell lung cancer (NSCLC) cells is [...] Read more.

Celastrol, a triterpene extracted from the Chinese herb Tripterygium wilfordii, has been shown to have multiple bioactivities. Although among these activities, its anti-cancer effects have attracted the most attention, the effect of celastrol on gefitinib-resistant non-small cell lung cancer (NSCLC) cells is not clearly known. Here, we examined the potency of celastrol in three different NSCLC cell lines. We explored its treatment mechanism in two gefitinib-resistant NSCLC cell lines (H1650 and H1975). Our data demonstrated that celastrol exerted its apoptotic effect in a dose- and time-dependent manner. Also, the mitochondria membrane potential was gradually lost and the ratio of Bax/Bcl-2 increased after the treatment of celastrol, both of which are indicators of mitochondria membrane integrity. Although the caspases were activated, the treatment with pan-caspase inhibitor could partially inhibit the level of apoptosis. Moreover, the protein level of Hsp90 client proteins, EGFR and AKT, was measured. Interestingly, both client proteins were remarkably down-regulated after the treatment of celastrol. Taken together, our data showed that celastrol may be developed as a promising agent for treating gefitinib-resistant NSCLCs by inducing apoptosis through caspase-dependent pathways and Hsp90 client protein degradation. Full article

(This article belongs to the Section Medicinal Chemistry)

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Open AccessArticle

Antioxidant Activity of Hispidin Oligomers from Medicinal Fungi: A DFT Study

by El Hassane Anouar, Syed Adnan Ali Shah, Normahanim Binti Hassan, Najoua El Moussaoui, Rohaya Ahmad, Mohd Zulkefeli and Jean-Frédéric F. Weber

Molecules 2014, 19(3), 3489-3507; https://doi.org/10.3390/molecules19033489 - 21 Mar 2014

Cited by 43 | Viewed by 8880

Abstract

Hispidin oligomers are styrylpyrone pigments isolated from the medicinal fungi Inonotus xeranticus and Phellinus linteus. They exhibit diverse biological activities and strong free radical scavenging activity. To rationalize the antioxidant activity of a series of four hispidin oligomers and determine the favored [...] Read more.

Hispidin oligomers are styrylpyrone pigments isolated from the medicinal fungi Inonotus xeranticus and Phellinus linteus. They exhibit diverse biological activities and strong free radical scavenging activity. To rationalize the antioxidant activity of a series of four hispidin oligomers and determine the favored mechanism involved in free radical scavenging, DFT calculations were carried out at the B3P86/6-31+G (d, p) level of theory in gas and solvent. The results showed that bond dissociation enthalpies of OH groups of hispidin oligomers (ArOH) and spin density delocalization of related radicals (ArO^•) are the appropriate parameters to clarify the differences between the observed antioxidant activities for the four oligomers. The effect of the number of hydroxyl groups and presence of a catechol moiety conjugated to a double bond on the antioxidant activity were determined. Thermodynamic and kinetic studies showed that the PC-ET mechanism is the main mechanism involved in free radical scavenging. The spin density distribution over phenoxyl radicals allows a better understanding of the hispidin oligomers formation. Full article

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Open AccessArticle

Inhibition of GlcNAc-Processing Glycosidases by C-6-Azido-NAG-Thiazoline and Its Derivatives

by Jana Krejzová, Petr Šimon, Lubica Kalachova, Natallia Kulik, Pavla Bojarová, Petr Marhol, Helena Pelantová, Josef Cvačka, Rüdiger Ettrich, Kristýna Slámová and Vladimír Křen

Molecules 2014, 19(3), 3471-3488; https://doi.org/10.3390/molecules19033471 - 20 Mar 2014

Cited by 12 | Viewed by 7607

Abstract

NAG-thiazoline is a strong competitive inhibitor of GH20 β-N-acetyl- hexosaminidases and GH84 β-N-acetylglucosaminidases. Here, we focused on the design, synthesis and inhibition potency of a series of new derivatives of NAG-thiazoline modified at the C-6 position. Dimerization of NAG-thiazoline [...] Read more.

NAG-thiazoline is a strong competitive inhibitor of GH20 β-N-acetyl- hexosaminidases and GH84 β-N-acetylglucosaminidases. Here, we focused on the design, synthesis and inhibition potency of a series of new derivatives of NAG-thiazoline modified at the C-6 position. Dimerization of NAG-thiazoline via C-6 attached triazole linkers prepared by click chemistry was employed to make use of multivalency in the inhibition. Novel compounds were tested as potential inhibitors of β-N-acetylhexosaminidases from Talaromyces flavus, Streptomyces plicatus (both GH20) and β-N-acetylglucosaminidases from Bacteroides thetaiotaomicron and humans (both GH84). From the set of newly prepared NAG-thiazoline derivatives, only C-6-azido-NAG-thiazoline displayed inhibition activity towards these enzymes; C-6 triazole-substituted NAG-thiazolines lacked inhibition activity against the enzymes used. Docking of C-6-azido-NAG-thiazoline into the active site of the tested enzymes was performed. Moreover, a stability study with GlcNAc-thiazoline confirmed its decomposition at pH < 6 yielding 2-acetamido-2-deoxy-1-thio-α/β-D-glucopyranoses, which presumably dimerize oxidatively into S-S linked dimers; decomposition products of NAG-thiazoline are void of inhibitory activity. Full article

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Open AccessArticle

Metabonomic Analysis of Water Extracts from Different Angelica Roots by ¹H-Nuclear Magnetic Resonance Spectroscopy

by Pui Hei Chan, Wendy L. Zhang, Chung-Ho Lau, Chi Yuen Cheung, Hector C. Keun, Karl W. K. Tsim and Henry Lam

Molecules 2014, 19(3), 3460-3470; https://doi.org/10.3390/molecules19033460 - 20 Mar 2014

Cited by 13 | Viewed by 8713

Abstract

Angelica Radix, the roots of the genus Angelica, has been used for more than 2,000 years as a traditional medicine in Eastern Asia. The Chinese Pharmacopoeia records more than 100 herbal formulae containing Angelica roots. There are two common sources of Angelica [...] Read more.

Angelica Radix, the roots of the genus Angelica, has been used for more than 2,000 years as a traditional medicine in Eastern Asia. The Chinese Pharmacopoeia records more than 100 herbal formulae containing Angelica roots. There are two common sources of Angelica roots, Angelica sinensis from China and A. gigas from Korea. The two species of Angelica roots differ in their chemical compositions, pharmacological properties and clinical efficacy. ¹H-NMR metabolic profiling has recently emerged as a promising quality control method for food and herbal chemistry. We explored the use of ¹H-NMR metabolic profiling for the quality control of Angelica Radix. Unlike previous work, we performed the metabolic profiling on hot water extracts, so as to mimic the clinically relevant preparation method. Unsupervised principle component analyses of both the full spectral profile and a selection of targeted molecules revealed a clear differentiation of three types of Angelica roots. In addition, the levels of 13 common metabolites were measured. Statistically significant differences in the levels of glucose, fructose and threonine were found between different sources of Angelica. Ferulic acid, a marker commonly used to evaluate Angelica root, was detected in our samples, but the difference in ferulic acid levels between the samples was not statistically significant. Overall, we successfully applied ¹H-NMR metabolic profiling with water extraction to discriminate all three sources of Angelica roots, and obtained quantitative information of many common metabolites. Full article

(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)

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Open AccessArticle

Authentication of Bulbus Fritillariae Cirrhosae by RAPD-Derived DNA Markers

by Gui-Zhong Xin, Yin-Ching Lam, Maitinuer Maiwulanjiang, Gallant K. L. Chan, Kevin Yue Zhu, Wai-Lun Tang, Tina Ting-Xia Dong, Zi-Qi Shi, Ping Li and Karl W. K. Tsim

Molecules 2014, 19(3), 3450-3459; https://doi.org/10.3390/molecules19033450 - 20 Mar 2014

Cited by 31 | Viewed by 8838

Abstract

Bulbus Fritillariae is the most commonly used antitussive herb in China. Eleven species of Fritillaria are recorded as Bulbus Fritillariae in the Chinese Pharmacopoeia. Bulbus Fritillariae Cirrhosae is a group of six Fritillaria species with higher efficiency and lower toxicity derived mainly from [...] Read more.

Bulbus Fritillariae is the most commonly used antitussive herb in China. Eleven species of Fritillaria are recorded as Bulbus Fritillariae in the Chinese Pharmacopoeia. Bulbus Fritillariae Cirrhosae is a group of six Fritillaria species with higher efficiency and lower toxicity derived mainly from wild sources. Because of their higher market price, five other Fritillaria species are often sold deceptively as Bulbus Fritillariae Cirrhosae in the herbal market. To ensure the efficacy and safety of medicinal herbs, the authentication of botanical resources is the first step in quality control. Here, a DNA based identification method was developed to authenticate the commercial sources of Bulbus Fritillariae Cirrhosae. A putative DNA marker (0.65 kb) specific for Bulbus Fritillariae Cirrhosae was identified using the Random Amplified Polymorphic DNA (RAPD) technique. A DNA marker representing a Sequence Characterized Amplified Region (SCAR) was developed from a RAPD amplicon. The SCAR marker was successfully applied to differentiate Bulbus Fritillariae Cirrhosae from different species of Fritillaria. Additionally, the SCAR marker was also useful in identifying the commercial samples of Bulbus Fritillariae Cirrhosae. Our results indicated that the RAPD-SCAR method was rapid, accurate and applicable in identifying Bulbus Fritillariae Cirrhosae at the DNA level. Full article

(This article belongs to the Special Issue Phytochemicals: Analytical and Medicinal Chemistry)

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Molecules, Volume 19, Issue 3 (March 2014) – 77 articles , Pages 2707-3850

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