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1.
Mar Drugs ; 13(6): 3849-76, 2015 Jun 18.
Article in English | MEDLINE | ID: mdl-26096274

ABSTRACT

Northern shrimp (Pandalus borealis) oil, which is rich in omega-3 fatty acids, was recovered from the cooking water of shrimp processing facilities. The oil contains significant amounts of omega-3 fatty acids in triglyceride form, along with substantial long-chain monounsaturated fatty acids (MUFAs). It also features natural isomeric forms of astaxanthin, a nutritional carotenoid, which gives the oil a brilliant red color. As part of our efforts in developing value added products from waste streams of the seafood processing industry, we present in this paper a comprehensive characterization of the triacylglycerols (TAGs) and astaxanthin esters that predominate in the shrimp oil by using HPLC-HRMS and MS/MS, as well as 13C-NMR. This approach, in combination with FAME analysis, offers direct characterization of fatty acid molecules in their intact forms, including the distribution of regioisomers in TAGs. The information is important for the standardization and quality control, as well as for differentiation of composition features of shrimp oil, which could be sold as an ingredient in health supplements and functional foods.


Subject(s)
Chromatography, High Pressure Liquid/methods , Oils/analysis , Pandalidae/chemistry , Tandem Mass Spectrometry/methods , Animals , Fatty Acids, Omega-3/analysis , Fatty Acids, Omega-3/isolation & purification , Magnetic Resonance Spectroscopy/methods , Oils/chemistry , Oils/isolation & purification , Triglycerides/analysis , Triglycerides/chemistry , Triglycerides/isolation & purification , Xanthophylls/analysis , Xanthophylls/chemistry , Xanthophylls/isolation & purification
2.
Chem Commun (Camb) ; 48(91): 11250-2, 2012 Nov 25.
Article in English | MEDLINE | ID: mdl-23070293

ABSTRACT

The addition of the ambiphilic molecule Me(2)AlCH(2)PMe(2) (1) to the allenyl vinyl ketone 2 gave a trapped Nazarov reaction product. Under kinetic control, the addition of the phosphine was on the methylated carbon, contrary to expected steric and electronic considerations. Computational data pointed to hydrogen bonding between the phosphine and the methyl group guiding the regiochemistry of this reaction. This product rearranged to provide the expected, regioisomeric Nazarov product. With additional 1 this compound yielded a Michael-addition product via a retro-Nazarov process.

3.
Chem Commun (Camb) ; 47(39): 11131-3, 2011 Oct 21.
Article in English | MEDLINE | ID: mdl-21897982

ABSTRACT

Species R(2)PCH(2)AlMe(2) (R = Me, Ph) are stable Lewis adducts but still react with CO(2) both in solution and in the solid state. The CO(2) adducts undergo a rearrangement unprecedented for ambiphilic molecules to form aluminium carboxylates. A new spirocyclic compound was also obtained by double Lewis pair activation of CO(2).

4.
Dalton Trans ; 40(36): 9202-11, 2011 Sep 28.
Article in English | MEDLINE | ID: mdl-21829831

ABSTRACT

A series of N,N',N''-trisubstituted guanidines (1-6) and their copper(II) complexes, [κ(2)(O,N)-C(6)H(5)CONHC(NHC(6)H(4)Cl)NR](2)Cu(ii) (R = iso-propyl (1a), n-butyl (2a), sec-butyl (3a), tert-butyl (4a), benzyl (5a), and para-tolyl (6a)) were synthesized and characterized using elemental analysis, FTIR and NMR spectroscopy. DFT studies were used to assess the location of the protons in the free ligands. However, calculations have shown that, in all cases, hydrogen bonding from either N-H group gives conformations that are very similar in energy. Single crystal XRD studies were used to characterize ligands 1 and 4 and the related complexes 1a and 4a. The structures reveal that these complexes are mononuclear in the solid state and that copper adopts a regular square planar geometry. In both metallic species, the N, N', N''-trisubstituted guanidine ligands chelate the Cu(II) atom using the oxygen and one nitrogen. The synthesized compounds were investigated for urease inhibition using thiourea as a standard drug. Most complexes exhibit a better activity than the respective guanidines and compound 1a was found to be the most active with IC(50) = 9.83 ± 0.07 µM (the IC(50) for thiourea is 21.0 ± 0.1 µM). The species were also screened for their anti-leishmanial activity. However, all of the compounds were devoid of any significant activity.


Subject(s)
Antiprotozoal Agents/pharmacology , Copper/pharmacology , Guanidines/pharmacology , Leishmania/drug effects , Urease/antagonists & inhibitors , Antiprotozoal Agents/chemistry , Copper/chemistry , Fabaceae/enzymology , Guanidines/chemistry , Humans , Leishmaniasis/drug therapy , Models, Molecular , Organometallic Compounds/chemistry , Organometallic Compounds/pharmacology , Urease/metabolism
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