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NMR characterization of guanine DNA site alkylated by kapurimycin A3, an antitumour antibiotic from Streptomyces sp

Chan KL, Sugiyama H, Saito I, Hara M

Phytochemistry, 1995 Nov;40(5):1373-4.
PMID: 8534399

The kapurimycin A3-guanine adduct was formed by alkylation of the antitumour antibiotic with d(CGCG)2. The site of alkylation of the guanine was confirmed by comparative NMR studies with N-7-methyl-guanine in DMSO-d6.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Kinetics and mechanism of large rate enhancement in the alkaline hydrolysis of N'-morpholino-N-(2'-methoxyphenyl)phthalamide

Sim YL, Ariffin A, Khan MN

J Org Chem, 2008 May 16;73(10):3730-7.
PMID: 18410141 DOI: 10.1021/jo702695k

The apparent second-order rate constant (k OH) for hydroxide-ion-catalyzed conversion of 1 to N-(2'-methoxyphenyl)phthalamate (4) is approximately 10(3)-fold larger than k OH for alkaline hydrolysis of N-morpholinobenzamide (2). These results are explained in terms of the reaction scheme 1 --> k(1obs) 3 --> k(2obs) 4 where 3 represents N-(2'-methoxyphenyl)phthalimide and the values of k(2obs)/k(1obs) vary from 6.0 x 10(2) to 17 x 10(2) within [NaOH] range of 5.0 x 10(-3) to 2.0 M. Pseudo-first-order rate constants (k(obs)) for alkaline hydrolysis of 1 decrease from 21.7 x 10(-3) to 15.6 x 10(-3) s(-1) with an increase in ionic strength (by NaCl) from 0.5 to 2.5 M at 0.5 M NaOH and 35 degrees C. The values of k obs, obtained for alkaline hydrolysis of 2 within [NaOH] range 1.0 x 10(-2) to 2.0 M at 35 degrees C, follow the relationship k(obs) = kOH[HO(-)] + kOH'[HO (-)] (2) with least-squares calculated values of kOH and kOH' as (6.38 +/- 0.15) x 10(-5) and (4.59 +/- 0.09) x 10(-5) M (-2) s(-1), respectively. A few kinetic runs for aqueous cleavage of 1, N'-morpholino-N-(2'-methoxyphenyl)-5-nitrophthalamide (5) and N'-morpholino-N-(2'-methoxyphenyl)-4-nitrophthalamide (6) at 35 degrees C and 0.05 M NaOH as well as 0.05 M NaOD reveal the solvent deuterium kinetic isotope effect (= k(obs) (H 2) (O)/ k(obs) (D 2 ) (O)) as 1.6 for 1, 1.9 for 5, and 1.8 for 6. Product characterization study on the cleavage of 5, 6, and N-(2'-methoxyphenyl)-4-nitrophthalimide (7) at 0.5 M NaOD in D2O solvent shows the imide-intermediate mechanism as the exclusive mechanism.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Naturally occurring labdane diterpene and benzofuran from Globba pendula

Maulidiani, Shaari K, Paetz C, Stanslas J, Abas F, Lajis NH

Nat Prod Commun, 2009 Aug;4(8):1031-6.
PMID: 19768978

Phytochemical investigation on Globba pendula resulted in the isolation of a new naturally occurring 16-oxo-(8)17-12-labdadien-15,11-olide 1 and benzofuran-2-carboxaldehyde 2. Other known compounds including isoandrographolide, indirubin, vanillin, vanillic acid, 2(3H)-benzoxazolone, as well as beta-sitosteryl-beta-D-glucopyranoside, beta-sitosterol, and 7alpha-hydroxysitosterol were also isolated. The structures were established based on spectroscopic data and comparison with the literature. Furthermore, the compound isoandrographolide has demonstrated strong cytotoxic properties towards a panel of cancer cell lines (MCF-7, PC-3, and H-460) with the IC50 values of 7.9, 8.7, and 9.0 microM, respectively.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Composition and thermal analysis of lard stearin and lard olein

Yanty NA, Marikkar JM, Man YB, Long K

J Oleo Sci, 2011;60(7):333-8.
PMID: 21701095

Lard being an edible fat could be used in different forms in food systems. In this study, composition and thermal analysis of lard stearin (LS) and lard olein (LO) were undertaken to determine some common parameters which would enable their detection in food. A sample of native lard was partitioned into LS and LO using acetone as solvent and the fractions were compared to the original sample with respect to basic physico-chemical parameters, fatty acid and triacylglycerol (TAG) composition, and thermal characteristics. Although LS and LO displayed wider variations in basic physico-chemical parameters, thermal properties and solidification behavior, they do possess some common characteristic features with regard to composition. In spite of the proportional differences in the major fatty acids, both LS and LO are found to possess extremely high amount of palmitic (C16:0) acid at the sn-2 positions of their TAG molecules. Similar to native lard, both LS and LO contained approximately equal proportions of TAG molecules namely, linoleoyl-palmitoyl-oleoyl glycerol (LPO) and dioleoyl-palmitoyl glycerol (OPO). Hence, the calculated LPO/OPO ratio for LS and LO are comparably similar to that of native lard.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
AChE inhibitor: a regio- and stereo-selective 1,3-dipolar cycloaddition for the synthesis of novel substituted 5,6-dimethoxy spiro[5.3']-oxindole-spiro-[6.3″]-2,3-dihydro-1H-inden-1″-one-7-(substituted aryl)-tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole

Ashraf Ali M, Ismail R, Choon TS, Kumar RS, Osman H, Arumugam N, et al.

Bioorg Med Chem Lett, 2012 Jan 1;22(1):508-11.
PMID: 22142546 DOI: 10.1016/j.bmcl.2011.10.087

Pyrrolothiazolyloxindole analogues share vital pharmacological properties, considered useful in Alzheimer's disease (AD). The aim of this study was synthesis and evaluate pyralothiazolyloxindole analogues if possess acetyl cholinesterase (AChE) inhibitory activity. The easily accessible one-pot synthesis of these compounds resulted to be significantly less difficult and expensive than that of donepezil. Several compounds possess anti-cholinesterase activity in the order of micro and sub-micromolar. Particularly, compound was the most potent inhibitors of the series against acetyl cholinesterase enzyme with IC(50) 0.11μmol/L.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Discrimination of three Pegaga (Centella) varieties and determination of growth-lighting effects on metabolites content based on the chemometry of 1H nuclear magnetic resonance spectroscopy

H M, Khatib A, Shaari K, Abas F, Shitan M, Kneer R, et al.

J Agric Food Chem, 2012 Jan 11;60(1):410-7.
PMID: 22084897 DOI: 10.1021/jf200270y

The metabolites of three species of Apiaceae, also known as Pegaga, were analyzed utilizing (1)H NMR spectroscopy and multivariate data analysis. Principal component analysis (PCA) and hierarchical cluster analysis (HCA) resolved the species, Centella asiatica, Hydrocotyle bonariensis, and Hydrocotyle sibthorpioides, into three clusters. The saponins, asiaticoside and madecassoside, along with chlorogenic acids were the metabolites that contributed most to the separation. Furthermore, the effects of growth-lighting condition to metabolite contents were also investigated. The extracts of C. asiatica grown in full-day light exposure exhibited a stronger radical scavenging activity and contained more triterpenes (asiaticoside and madecassoside), flavonoids, and chlorogenic acids as compared to plants grown in 50% shade. This study established the potential of using a combination of (1)H NMR spectroscopy and multivariate data analyses in differentiating three closely related species and the effects of growth lighting, based on their metabolite contents and identification of the markers contributing to their differences.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods*
Application of differential scanning calorimetry (DSC), HPLC and pNMR for interpretation primary crystallisation caused by combined low and high melting TAGs

Saadi S, Ariffin AA, Ghazali HM, Miskandar MS, Boo HC, Abdulkarim SM

Food Chem, 2012 May 1;132(1):603-12.
PMID: 26434338 DOI: 10.1016/j.foodchem.2011.10.095

The main goal of the present work was to assess the mechanism of crystallisation, more precisely the dominant component responsible for primary crystal formations and fat agglomerations. Therefore, DSC results exhibited significant effect on temperature transition; peak sharpness and enthalpy at palm stearin (PS) levels more than 40wt.%. HPLC data demonstrated slight reduction in the content of POO/OPO at PS levels less than 40wt.%, while the excessive addition of PS more than 40wt.% increased significantly PPO/POP content. The pNMR results showed significant drop in SFC for blends containing PS less than 40wt.%, resulting in low SFC less than 15% at body temperature (37°C). Moreover, the values of viscosity (η) and shear stress (τ) at PS levels over 40wt.% expressed excellent internal friction of the admixtures. All the data reported indicate that PPO/POP was the major component of primary nucleus developed. In part, the levels of PS should be less than 40wt.%, if these blends are designed to be used for margarine production.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods*
Characterisation of a remineralising Glass Carbomer® ionomer cement by MAS-NMR spectroscopy

Zainuddin N, Karpukhina N, Law RV, Hill RG

Dent Mater, 2012 Oct;28(10):1051-8.
PMID: 22841162 DOI: 10.1016/j.dental.2012.06.011

The purpose of this study was to characterize commercial glass polyalkenoate cement (GPC) or glass ionomer cement (GIC), Glass Carbomer(®), which is designed to promote remineralization to fluorapatite (FAp) in the mouth. The setting reaction of the cement was followed using magic angle spinning nuclear magnetic resonance (MAS-NMR) spectroscopy.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods*
Fulltext The isolation of a new S-methyl benzothioate compound from a marine-derived Streptomyces sp

Mahyudin NA, Blunt JW, Cole AL, Munro MH

J Biomed Biotechnol, 2012;2012:894708.
PMID: 22291452 DOI: 10.1155/2012/894708

The application of an HPLC bioactivity profiling/microtiter plate technique in conjunction with microprobe NMR instrumentation and access to the AntiMarin database has led to the isolation of a new 1. In this example, 1 was isolated from a cytotoxic fraction of an extract obtained from marine-derived Streptomyces sp. cultured on Starch Casein Agar (SCA) medium. The 1D and 2D (1)H NMR and ESIMS data obtained from 20 μg of compound 1 fully defined the structure. The known 2 was also isolated and readily dereplicated using this approach.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Improved diagnostic accuracy in differentiating malignant and benign lesions using single-voxel proton MRS of the breast at 3 T MRI

Suppiah S, Rahmat K, Mohd-Shah MN, Azlan CA, Tan LK, Aziz YF, et al.

Clin Radiol, 2013 Sep;68(9):e502-10.
PMID: 23706826 DOI: 10.1016/j.crad.2013.04.002

To investigate the diagnostic accuracy of single-voxel proton magnetic resonance spectroscopy (SV (1)H MRS) by quantifying total choline-containing compounds (tCho) in differentiating malignant from benign lesions, and subsequently, to analyse the relationship of tCho levels in malignant breast lesions with their histopathological subtypes.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Complete NMR assignments of bioactive rotameric (3 → 8) biflavonoids from the bark of Garcinia hombroniana

Jamila N, Khairuddean M, Khan SN, Khan N

Magn Reson Chem, 2014 Jul;52(7):345-52.
PMID: 24700704 DOI: 10.1002/mrc.4071

The genus Garcinia is reported to possess antimicrobial, anti-inflammatory, anticancer, hepatoprotective and anti-HIV activities. Garcinia hombroniana in Malaysia is used to treat itching and as a protective medicine after child birth. This study was aimed to isolate the chemical constituents from the bark of G. hombroniana and explore their possible pharmacological potential. Ethyl acetate extract afforded one new (1) and six (2-7) known 3 → 8 rotameric biflavonoids. Their structures were elucidated by UV, IR and NMR (1D and 2D) spectroscopy together with electron ionization/ESI mass spectrometric techniques and were identified as (2R, 3S) volkensiflavone-7-O-rhamnopyranoside (1), volkensiflavone (2), 4″-O-methyl-volkensiflavone (3), volkensiflavone-7-O-glucopyranoside (4), morelloflavone (5), 3″-O-methyl-morelloflavone (6) and morelloflavone-7-O-glucopyranoside (7). The absolute configuration of compound 1 was assigned by circular dichroism spectroscopy as 2R, 3S. The coexistence of conformers of isolated biflavonoids in solution at 25 °C in different solvents was confirmed by variable temperature NMR studies. At room temperature (25 °C), compounds 1-7 exhibited duplicate NMR signals, while at elevated temperature (90 °C), a single set of signals was obtained. Compound 5 showed significant in vitro antioxidant activities against 1,1-diphenyl-2-picrylhydrazyl and 2,2'-azino-bis-3-ethyl benzthiazoline-6-sulfonic acid radicals. The antibacterial studies showed that compounds 5 and 6 are the most active against Staphylococcus aureus, Bacillus subtilis and Escherichia coli. Compounds 3 and 6 also showed moderate antituberculosis activity against H38 Rv. Based on the research findings, G. hombroniana could be concluded as a rich source of flavanone-flavone (3 → 8) biflavonoids that exhibit rotameric behaviour at room temperature and display significant antioxidant and antibacterial activities.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Fulltext Bioconversion of rebaudioside I from rebaudioside A

Prakash I, Bunders C, Devkota KP, Charan RD, Ramirez C, Snyder TM, et al.

Molecules, 2014 Oct 28;19(11):17345-55.
PMID: 25353385 DOI: 10.3390/molecules191117345

To supply the increasing demand of natural high potency sweeteners to reduce the calories in food and beverages, we have looked to steviol glycosides. In this work we report the bioconversion of rebaudioside A to rebaudioside I using a glucosyltransferase enzyme. This bioconversion reaction adds one sugar unit with a 1→3 linkage. We utilized 1D and 2D NMR spectroscopy (1H, 13C, COSY, HSQC-DEPT, HMBC, 1D TOCSY and NOESY) and mass spectral data to fully characterize rebaudioside I.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Multinuclear MR and multilevel data processing: an insight into morphologic assessment of in vivo knee articular cartilage

Hani AF, Kumar D, Malik AS, Walter N, Razak R, Kiflie A

Acad Radiol, 2015 Jan;22(1):93-104.
PMID: 25481518 DOI: 10.1016/j.acra.2014.08.008

Quantitative assessment of knee articular cartilage (AC) morphology using magnetic resonance (MR) imaging requires an accurate segmentation and 3D reconstruction. However, automatic AC segmentation and 3D reconstruction from hydrogen-based MR images alone is challenging because of inhomogeneous intensities, shape irregularity, and low contrast existing in the cartilage region. Thus, the objective of this research was to provide an insight into morphologic assessment of AC using multilevel data processing of multinuclear ((23)Na and (1)H) MR knee images.

Matched MeSH terms: Proton Magnetic Resonance Spectroscopy/methods*
Investigation of interaction studies of cefpirome with ACE-inhibitors in various buffers

Nawaz M, Arayne MS, Sultana N, Abbas HF

Spectrochim Acta A Mol Biomol Spectrosc, 2015 Feb 25;137:1050-4.
PMID: 25300038 DOI: 10.1016/j.saa.2014.08.152

This work describes a RP-HPLC method for the determination and interaction studies of cefpirome with ACE-inhibitors (captopril, enalapril and lisinopril) in various buffers. The separation and interaction of cefpirome with ACE-inhibitors was achieved on a Purospher Star, C18 (5 μm, 250×4.6 mm) column. Mobile phase consisted of methanol: water (80:20, v/v, pH 3.3); however, for the separation of lisinopril, it was modified to methanol-water (40:60, v/v, pH 3.3) and pumped at a flow rate of 1 mL min(-1). In all cases, UV detection was performed at 225 nm. Interactions were carried out in physiological pH i.e., pH 1 (simulated gastric juice), 4 (simulated full stomach), 7.4 (blood pH) and 9 (simulated GI), drug contents were analyzed by reverse phase high performance liquid chromatography. Method was found linear in the concentration range of 1.0-50.0 μg mL(-1) with correlation coefficient (r(2)) of 0.999. Precision (RSD%) was less than 2.0%, indicating good precision of the method and accuracy was 98.0-100.0%. Furthermore, cefpirome-ACE-inhibitors' complexes were also synthesized and results were elucidated on the basis of FT-IR, and (1)H NMR. The interaction results show that these interactions are pH dependent and for the co-administration of cefpirome and ACE-inhibitors, a proper interval should be given.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Fulltext Synthesis, molecular structure and spectroscopic investigations of novel fluorinated spiro heterocycles

Islam MS, Al-Majid AM, Barakat A, Soliman SM, Ghabbour HA, Quah CK, et al.

Molecules, 2015 May 07;20(5):8223-41.
PMID: 25961163 DOI: 10.3390/molecules20058223

This paper describes an efficient and regioselective method for the synthesis of novel fluorinated spiro-heterocycles in excellent yield by cascade [5+1] double Michael addition reactions. The compounds 7,11-bis(4-fluorophenyl)-2,4-dimethyl- 2,4-diazaspiro[5.5] undecane-1,3,5,9-tetraone (3a) and 2,4-dimethyl-7,11-bis (4-(trifluoromethyl)phenyl)-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone (3b) were characterized by single-crystal X-ray diffraction, FT-IR and NMR techniques. The optimized geometrical parameters, infrared vibrational frequencies and NMR chemical shifts of the studied compounds have also been calculated using the density functional theory (DFT) method, using Becke-3-Lee-Yang-Parr functional and the 6-311G(d,p) basis set. There is good agreement between the experimentally determined structural parameters, vibrational frequencies and NMR chemical shifts of the studied compounds and those predicted theoretically. The calculated natural atomic charges using NBO method showed higher polarity of 3a compared to 3b.The calculated electronic spectra are also discussed based on the TD-DFT calculations.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods
Optimization of cell disruption methods for efficient recovery of bioactive metabolites via NMR of three freshwater microalgae (chlorophyta)

Ma NL, Teh KY, Lam SS, Kaben AM, Cha TS

Bioresour Technol, 2015 Aug;190:536-42.
PMID: 25812996 DOI: 10.1016/j.biortech.2015.03.036

This study demonstrates the use of NMR techniques coupled with chemometric analysis as a high throughput data mining method to identify and examine the efficiency of different disruption techniques tested on microalgae (Chlorella variabilis, Scenedesmus regularis and Ankistrodesmus gracilis). The yield and chemical diversity from the disruptions together with the effects of pre-oven and pre-freeze drying prior to disruption techniques were discussed. HCl extraction showed the highest recovery of oil compounds from the disrupted microalgae (up to 90%). In contrast, NMR analysis showed the highest intensity of bioactive metabolites obtained for homogenized extracts pre-treated with freeze-drying, indicating that homogenizing is a more favorable approach to recover bioactive substances from the disrupted microalgae. The results show the potential of NMR as a useful metabolic fingerprinting tool for assessing compound diversity in complex microalgae extracts.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods*
Fulltext Metabolomic profiles of hepatocellular carcinoma in a European prospective cohort

Fages A, Duarte-Salles T, Stepien M, Ferrari P, Fedirko V, Pontoizeau C, et al.

BMC Med, 2015 Sep 23;13:242.
PMID: 26399231 DOI: 10.1186/s12916-015-0462-9

BACKGROUND: Hepatocellular carcinoma (HCC), the most prevalent form of liver cancer, is difficult to diagnose and has limited treatment options with a low survival rate. Aside from a few key risk factors, such as hepatitis, high alcohol consumption, smoking, obesity, and diabetes, there is incomplete etiologic understanding of the disease and little progress in identification of early risk biomarkers.
METHODS: To address these aspects, an untargeted nuclear magnetic resonance metabolomic approach was applied to pre-diagnostic serum samples obtained from first incident, primary HCC cases (n = 114) and matched controls (n = 222) identified from amongst the participants of a large European prospective cohort.
RESULTS: A metabolic pattern associated with HCC risk comprised of perturbations in fatty acid oxidation and amino acid, lipid, and carbohydrate metabolism was observed. Sixteen metabolites of either endogenous or exogenous origin were found to be significantly associated with HCC risk. The influence of hepatitis infection and potential liver damage was assessed, and further analyses were made to distinguish patterns of early or later diagnosis.
CONCLUSION: Our results show clear metabolic alterations from early stages of HCC development with application for better etiologic understanding, prevention, and early detection of this increasingly common cancer.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods*
Fulltext Detection of Butter Adulteration with Lard by Employing (1)H-NMR Spectroscopy and Multivariate Data Analysis

Fadzillah NA, Man Yb, Rohman A, Rosman AS, Ismail A, Mustafa S, et al.

J Oleo Sci, 2015;64(7):697-703.
PMID: 25994556 DOI: 10.5650/jos.ess14255

The authentication of food products from the presence of non-allowed components for certain religion like lard is very important. In this study, we used proton Nuclear Magnetic Resonance ((1)H-NMR) spectroscopy for the analysis of butter adulterated with lard by simultaneously quantification of all proton bearing compounds, and consequently all relevant sample classes. Since the spectra obtained were too complex to be analyzed visually by the naked eyes, the classification of spectra was carried out.The multivariate calibration of partial least square (PLS) regression was used for modelling the relationship between actual value of lard and predicted value. The model yielded a highest regression coefficient (R(2)) of 0.998 and the lowest root mean square error calibration (RMSEC) of 0.0091% and root mean square error prediction (RMSEP) of 0.0090, respectively. Cross validation testing evaluates the predictive power of the model. PLS model was shown as good models as the intercept of R(2)Y and Q(2)Y were 0.0853 and -0.309, respectively.

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods*
Fulltext 1H NMR-based metabolomics investigation of copper-laden rat: a model of Wilson's disease

Xu J, Jiang H, Li J, Cheng KK, Dong J, Chen Z

PLoS One, 2015;10(4):e0119654.
PMID: 25849323 DOI: 10.1371/journal.pone.0119654

Wilson's disease (WD), also known as hepatoleticular degeneration (HLD), is a rare autosomal recessive genetic disorder of copper metabolism, which causes copper to accumulate in body tissues. In this study, rats fed with copper-laden diet are used to render the clinical manifestations of WD, and their copper toxicity-induced organ lesions are studied. To investigate metabolic behaviors of 'decoppering' process, penicillamine (PA) was used for treating copper-laden rats as this chelating agent could eliminate excess copper through the urine. To date, there has been limited metabolomics study on WD, while metabolic impacts of copper accumulation and PA administration have yet to be established.

Matched MeSH terms: Proton Magnetic Resonance Spectroscopy/methods*
Fulltext Novel application of chemical shift gradient echo in- and opposed-phase sequences in 3 T MRI for the detection of H-MRS visible lipids and grading of glioma

Ramli N, Khairy AM, Seow P, Tan LK, Wong JH, Ganesan D, et al.

Eur Radiol, 2016 Jul;26(7):2019-29.
PMID: 26560718 DOI: 10.1007/s00330-015-4045-0

OBJECTIVES: We evaluated the feasibility of using chemical shift gradient-echo (GE) in- and opposed-phase (IOP) imaging to grade glioma.
METHODS: A phantom study was performed to investigate the correlation of (1)H MRS-visible lipids with the signal loss ratio (SLR) obtained using IOP imaging. A cross-sectional study approved by the institutional review board was carried out in 22 patients with different glioma grades. The patients underwent scanning using IOP imaging and single-voxel spectroscopy (SVS) using 3T MRI. The brain spectra acquisitions from solid and cystic components were obtained and correlated with the SLR for different grades.
RESULTS: The phantom study showed a positive linear correlation between lipid quantification at 0.9 parts per million (ppm) and 1.3 ppm with SLR (r = 0.79-0.99, p

Matched MeSH terms: Magnetic Resonance Spectroscopy/methods*

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