MyMedR

Displaying all 8 publications

Abstract:

Sort:

Unusual phenethylamine-containing alkaloids from Elaeocarpus tectorius

Ezeoke MC, Krishnan P, Sim DS, Lim SH, Low YY, Chong KW, et al.

Phytochemistry, 2018 Feb;146:75-81.
PMID: 29247894 DOI: 10.1016/j.phytochem.2017.12.003

From the leaves of Elaeocarpus tectorius (Lour.) Poir. four previously undescribed phenethylamine-containing alkaloids were isolated, namely, tectoricine, possessing an unprecedented isoquinuclidinone ring system incorporating a phenethylamine moiety, tectoraline, representing a rare alkamide incorporating two phenethylamine moieties, and tectoramidines A and B, representing the first naturally occurring trimeric and dimeric phenethylamine alkaloids incorporating an amidine function. The structures of these alkaloids were established by detailed spectroscopic analysis. The absolute configuration of tectoricine was determined by comparison of the experimental and calculated ECD spectra. Plausible biosynthetic pathways to the four alkaloids are proposed.

Matched MeSH terms: Phenethylamines/isolation & purification; Phenethylamines/chemistry*
Schwarzinicines A-G, 1,4-Diarylbutanoid-Phenethylamine Conjugates from the Leaves of Ficus schwarzii

Krishnan P, Lee FK, Yap VA, Low YY, Kam TS, Yong KT, et al.

J Nat Prod, 2020 01 24;83(1):152-158.
PMID: 31935094 DOI: 10.1021/acs.jnatprod.9b01160

Schwarzinicines A-G (1-7), representing the first examples of 1,4-diarylbutanoid-phenethylamine conjugates, were isolated from the leaves of Ficus schwarzii. The structures of these compounds were determined by detailed analysis of their MS, 1D and 2D NMR data. Compounds 1-4 exhibited pronounced vasorelaxant effects in the rat isolated aorta (Emax 106-120%; EC50 0.96-2.10 μM). However, compounds 1 and 2 showed no cytotoxic effects against A549, MCF-7, and HCT 116 human cancer cells (IC50 > 10 μM).

Matched MeSH terms: Phenethylamines/isolation & purification; Phenethylamines/pharmacology; Phenethylamines/chemistry*
Beta-agonist residues in cattle, chicken and swine livers at the wet market and the environmental impacts of wastewater from livestock farms in Selangor State, Malaysia

Sakai N, Sakai M, Mohamad Haron DE, Yoneda M, Ali Mohd M

Chemosphere, 2016 Dec;165:183-190.
PMID: 27654221 DOI: 10.1016/j.chemosphere.2016.09.022

Fourteen beta-agonists were quantitatively analyzed in cattle, chicken and swine liver specimens purchased at 14 wet markets in Selangor State, Malaysia, by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The health risks of ractopamine and clenbuterol residues in the Malaysian population were assessed based on quantitative data and meat consumption statistics in Malaysia. Wastewater samples collected at swine farms (n = 2) and cattle/cow farms (n = 2) in the Kuala Langat district were analyzed for the presence for the 14 compounds. Wastewater in chicken farms was not collected because there was negligible discharge during the breeding period. The environmental impacts caused by beta-agonists discharged from livestock farms were spatially assessed in the Langat River basin using a geographic information system (GIS). As a result, 10 compounds were detected in the liver specimens. Ractopamine, which is a permitted compound for swine in Malaysia, was frequently detected in swine livers; also, 9 other compounds that are prohibited compounds could be illegally abused among livestock farms. The health risks of ractopamine and clenbuterol were assessed to be minimal as their hazard quotients were no more than 7.82 × 10(-4) and 2.71 × 10(-3), respectively. Five beta-agonists were detected in the wastewater samples, and ractopamine in the swine farm resulted in the highest contamination (30.1 μg/L). The environmental impacts of the beta-agonists in the Langat River basin were generally concluded to be minimal, but the ractopamine contamination released from swine farms was localized in coastal areas near the estuary of the Langat River basin because most swine farms were located in that region.

Matched MeSH terms: Phenethylamines/analysis*; Phenethylamines/toxicity
Concise synthesis of the vasorelaxant alkaloids schwarzinicines A and B

Lee FK, Krishnan P, Muhamad A, Low YY, Kam TS, Ting KN, et al.

Nat Prod Res, 2021 Mar 22.
PMID: 33749454 DOI: 10.1080/14786419.2021.1903005

A concise synthesis of the 1,4-diarylbutanoid-phenethylamine alkaloids, schwarzinicines A (1) and B (2), recently isolated from Ficus schwarzii, is reported. Key steps include a Claisen condensation to assemble the 1,4-diaryl-2-butanone intermediate, followed by a reductive amination to furnish the core skeleton of the target compounds. The overall synthetic yields of 1 and 2 were 9.1% and 3.5%, respectively. Synthetic (-)-1, (+)-1 and (±)-1 exhibited comparable vasorelaxation as natural schwarzinicine A on rat isolated aortic rings, suggesting that the observed vasorelaxant effects were not influenced by the chirality at C-2.

Matched MeSH terms: Phenethylamines
Electrochemical detection of ractopamine at arrays of micro-liquid | liquid interfaces

Sairi M, Arrigan DW

Talanta, 2015 Jan;132:205-14.
PMID: 25476299 DOI: 10.1016/j.talanta.2014.08.060

The behaviour of protonated ractopamine (RacH(+)) at an array of micro-interfaces between two immiscible electrolyte solutions (micro-ITIES) was investigated via cyclic voltammetry (CV) and linear sweep stripping voltammetry (LSSV). The micro-ITIES array was formed at silicon membranes containing 30 pores of radius 11.09±0.12 µm and pore centre-to-centre separation of 18.4±2.1 times the pore radius. CV shows that RacH(+) transferred across the water |1,6-dichlorohexane µITIES array at a very positive applied potential, close to the upper limit of the potential window. Nevertheless, CV was used in the estimation of some of the drug's thermodynamic parameters, such as the formal transfer potential and the Gibbs transfer energy. LSSV was implemented by pre-concentration of the drug, into the organic phase, followed by voltammetric detection, based on the back-transfer of RacH(+) from the organic to aqueous phase. Under optimised pre-concentration and detection conditions, a limit of detection of 0.1 µM was achieved. In addition, the impact of substances such as sugar, ascorbic acid, metal ions, amino acid and urea on RacH(+) detection was assessed. The detection of RacH(+) in artificial serum indicated that the presence of serum protein interferes in the detection signal, so that sample deproteinisation is required for feasible bioanalytical applications.

Matched MeSH terms: Phenethylamines/analysis*
Preparation and in vitro evaluation of mebeverine HCl colon-targeted drug delivery system

Abdullah GZ, Abdulkarim MF, Chitneni M, Mutee AF, Ameer OZ, Salman IM, et al.

Pharm Dev Technol, 2011 Aug;16(4):331-42.
PMID: 20429815 DOI: 10.3109/10837451003739255

Mebeverine HCl is a water soluble drug commonly used to treat irritable bowel syndrome by acting directly on the smooth muscles of the colon. This work was aimed at the formulation and in vitro evaluation of a colon-targeted drug delivery system containing mebeverine HCl. Matrix tablets were prepared using ethyl cellulose (EC), Eudragit RL 100 either solely or in combination by wet granulation technique. Dissolution was carried out in 0.1 N HCl for 2?h followed by pH 6.8 phosphate buffer for eight hours. Uncoated forms released more than 5% drug in 0.1 N HCl therefore, Eudragit L100 was used as a coat. The results indicated very slow release profile. As a result, single retardant was used to prepare the matrix and coated by Eudragit L 100. The matrix containing 7% Eudragit RL 100 and 6% of binder was subjected to further studies to assess the effect of different coats (Eudragit L 100-55 and cellulose acetate phthalate) and different binders (pectin and sodium alginate) on the release profile. Eudragit L 100 and pectin were the best coating agent and binder, respectively. The final formula was stable and it can be concluded that the prepared system has the potential to deliver mebeverine HCl in vivo to the colon.

Matched MeSH terms: Phenethylamines/administration & dosage*; Phenethylamines/pharmacokinetics
Fulltext Mini review : the effects of food processing on biogenic amines formation

Chong, C.Y., Abu Bakar, F., Russly, A.R., Jamilah, B., Mahyudin, N.A.

International Food Research Journal, 2011;18(3):-.
MyJurnal

Biological amines are nitrogenous compounds that occur naturally in wide variety of food. Histamine, putrescine, cadavarine, tyramine, spermine, spermidine, tryptamine and β-phenylethylamine are the biogenic amines that are normally present in foods. Although the biogenic amines play some important physiological functions but high level of amines can cause toxicological effects. High amount of amines can be produced by bacteria during amino acids decarboxylation and have been identified as one of the important agent causing seafood intoxication. Temperature is the major factor for controlling the biogenic amines formation in food. The effects of other alternatives are also discussed including salting, packaging, irradiation, high pressure processing and the use of starter culture. A variety of techniques can be combined together to control the microbial growth and enzyme activity during processing and storage for better shelf life extension and food safety.

Matched MeSH terms: Phenethylamines
Anti-depressant activity of Erythrina variegata bark extract and regulation of monoamine oxidase activities in mice

Martins J, Brijesh S

J Ethnopharmacol, 2019 Oct 07.
PMID: 31600560 DOI: 10.1016/j.jep.2019.112280

ETHNOPHARMACOLOGICAL RELEVANCE: Erythrina variegata, commonly referred to as 'tiger's claw' or 'Indian coral tree' and 'Parijata' in Sanskrit, belongs to the Fabaceae family. It is a plant native to the coast of India, China, Malaysia, East Africa, Northern Australia and distributed in tropical and subtropical regions worldwide. In traditional medicine, 'Paribhadra' an Indian preparation, makes use of the leaves and bark of E. variegata to destroy pathogenic parasites and relieve joint pains. E. variegata is known to exhibit anxiolytic and anti-convulsant activities. Folkore medicine also suggests that E. variegata barks act on the central nervous system. However, there is a lack of data demonstrating this. The anti-depressant activity of E. variegata bark has not been reported in literature.
AIM OF THE STUDY: Our study focuses on previously unreported anti-depressant activity of E. variegata bark ethanolic extract (EBE) and determination of its mechanism of action possibly through regulation of monoamine oxidase activity in mouse brain homogenates.
MATERIALS AND METHODS: EBE was characterized using standard protocols for phytochemical analysis, followed by liquid chromatography-mass spectrometry (LC-MS) and gas chromatography-mass spectrometry (GC-MS) analysis. Anti-depressant activity of EBE (50, 100, 200 and 500 mg/kg) was evaluated in Swiss white albino mice using acute and chronic forced swim test (FST) models. Furthermore, the potential use of the extract as an adjunct to selective serotonin reuptake inhibitor (SSRI), escitalopram, was evaluated using the chronic unpredictable mild stress test model wherein inhibitory effects on monoamine oxidase (MAO) A and B were assessed by spectrophotometric-chemical analysis in mouse whole brain homogenates.
RESULTS: The extract showed significant reduction in immobility time periods in both acute (200 mg/kg) and chronic (100, 200 and 500 mg/kg) FST models. When used as an adjunct with escitalopram (15 mg/kg), the extract (100, 200 and 500 mg/kg) showed significantly greater inhibition of MAO-A and B activities when compared to escitalopram alone (30 mg/kg). Phytochemical analysis of EBE revealed presence of sugars, steroids, glycosides, alkaloids and tannins. LC-MS and GC-MS analysis identified components such as 2-amino-3-methyl-1-butanol, phenylethylamine, eriodictyol, daidzein and pomiferin, N-ethyl arachidonoyl amine, inosine diphosphate, trimipramine, granisetron, 3,4-dihydroxymandelic acid, ethyl ester, tri-TMS and dodecane, previously reported for their anti-depressant activity.
CONCLUSIONS: The study thus demonstrated potential for use of the E. variegata bark ethanolic extract as an adjunct to currently available SSRI treatment. The study also identified components present in E. variegata bark ethanolic extract that may be responsible for its anti-depressant activity. Furthermore, the study thus confirms the traditional use of E. variegata barks in improving CNS function through its anti-depressant like activity.

Matched MeSH terms: Phenethylamines