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

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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
Molecules 2014, 19(3), 3850; https://doi.org/10.3390/molecules19033850
Received: 20 March 2014 / Accepted: 25 March 2014 / Published: 25 March 2014
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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
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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
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
Molecules 2014, 19(3), 3848-3849; https://doi.org/10.3390/molecules19033848
Received: 4 March 2014 / Accepted: 11 March 2014 / Published: 24 March 2014
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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
Molecules 2014, 19(3), 3832-3847; https://doi.org/10.3390/molecules19033832
Received: 31 January 2014 / Revised: 11 March 2014 / Accepted: 21 March 2014 / Published: 24 March 2014
Cited by 7 | PDF Full-text (643 KB) | HTML Full-text | XML Full-text | Supplementary Files
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 15, involving the nL molecules as monodentate coordinated
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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 15, 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 35). 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
Molecules 2014, 19(3), 3820-3831; https://doi.org/10.3390/molecules19033820
Received: 30 December 2013 / Revised: 16 March 2014 / Accepted: 17 March 2014 / Published: 24 March 2014
Cited by 2 | PDF Full-text (594 KB) | HTML Full-text | XML Full-text
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
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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
Molecules 2014, 19(3), 3813-3819; https://doi.org/10.3390/molecules19033813
Received: 7 February 2014 / Revised: 20 March 2014 / Accepted: 21 March 2014 / Published: 24 March 2014
Cited by 8 | PDF Full-text (181 KB) | HTML Full-text | XML Full-text
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
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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)
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.
Molecules 2014, 19(3), 3804-3812; https://doi.org/10.3390/molecules19033804
Received: 31 December 2013 / Revised: 7 March 2014 / Accepted: 10 March 2014 / Published: 24 March 2014
Cited by 6 | PDF Full-text (212 KB) | HTML Full-text | XML Full-text
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
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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
Molecules 2014, 19(3), 3793-3803; https://doi.org/10.3390/molecules19033793
Received: 7 January 2014 / Revised: 13 March 2014 / Accepted: 19 March 2014 / Published: 24 March 2014
Cited by 27 | PDF Full-text (1080 KB) | HTML Full-text | XML Full-text
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
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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
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Open AccessArticle Synthesis, Cytotoxic Activity and 2D-QSAR Study of Some Imidazoquinazoline Derivatives
Molecules 2014, 19(3), 3777-3792; https://doi.org/10.3390/molecules19033777
Received: 14 January 2014 / Revised: 17 March 2014 / Accepted: 19 March 2014 / Published: 24 March 2014
Cited by 3 | PDF Full-text (339 KB) | HTML Full-text | XML Full-text
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
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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
Molecules 2014, 19(3), 3761-3776; https://doi.org/10.3390/molecules19033761
Received: 16 January 2014 / Revised: 17 March 2014 / Accepted: 18 March 2014 / Published: 24 March 2014
Cited by 5 | PDF Full-text (717 KB) | HTML Full-text | XML Full-text
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
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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
Molecules 2014, 19(3), 3744-3760; https://doi.org/10.3390/molecules19033744
Received: 27 January 2014 / Revised: 28 February 2014 / Accepted: 5 March 2014 / Published: 24 March 2014
Cited by 6 | PDF Full-text (2340 KB) | HTML Full-text | XML Full-text
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
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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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Open AccessArticle Microencapsulation of Purified Amylase Enzyme from Pitaya (Hylocereus polyrhizus) Peel in Arabic Gum-Chitosan using Freeze Drying
Molecules 2014, 19(3), 3731-3743; https://doi.org/10.3390/molecules19033731
Received: 15 January 2014 / Revised: 10 March 2014 / Accepted: 11 March 2014 / Published: 24 March 2014
Cited by 9 | PDF Full-text (425 KB) | HTML Full-text | XML Full-text
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
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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
Molecules 2014, 19(3), 3718-3730; https://doi.org/10.3390/molecules19033718
Received: 16 January 2014 / Revised: 13 March 2014 / Accepted: 14 March 2014 / Published: 24 March 2014
Cited by 6 | PDF Full-text (3985 KB) | HTML Full-text | XML Full-text
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
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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
Molecules 2014, 19(3), 3696-3717; https://doi.org/10.3390/molecules19033696
Received: 4 February 2014 / Revised: 7 March 2014 / Accepted: 15 March 2014 / Published: 24 March 2014
Cited by 13 | PDF Full-text (1425 KB) | HTML Full-text | XML Full-text
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
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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
Molecules 2014, 19(3), 3681-3695; https://doi.org/10.3390/molecules19033681
Received: 15 January 2014 / Revised: 15 March 2014 / Accepted: 19 March 2014 / Published: 24 March 2014
Cited by 7 | PDF Full-text (826 KB) | HTML Full-text | XML Full-text
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
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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
Molecules 2014, 19(3), 3669-3680; https://doi.org/10.3390/molecules19033669
Received: 25 February 2014 / Revised: 14 March 2014 / Accepted: 17 March 2014 / Published: 24 March 2014
Cited by 7 | PDF Full-text (251 KB) | HTML Full-text | XML Full-text | Supplementary Files
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
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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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