1.Synthesis and antiproliferative activity of two diastereomeric lignan amides serving as dimeric caffeic acid-l-DOPA hybrids.
Magoulas GE1, Rigopoulos A2, Piperigkou Z3, Gialeli C4, Karamanos NK5, Takis PG6, Troganis AN6, Chrissanthopoulos A7, Maroulis G7, Papaioannou D2. Bioorg Chem. 2016 Apr 23;66:132-144. doi: 10.1016/j.bioorg.2016.04.003. [Epub ahead of print]
Two new diastereomeric lignan amides (4 and 5) serving as dimeric caffeic acid-l-DOPA hybrids were synthesized. The synthesis involved the FeCl3-mediated phenol oxidative coupling of methyl caffeate to afford trans-diester 1a as a mixture of enantiomers, protection of the catechol units, regioselective saponification, coupling with a suitably protected l-DOPA derivative, separation of the two diastereomers thus obtained by flash column chromatography and finally global chemoselective deprotection of the catechol units. The effect of hybrids 4 and 5 and related compounds on the proliferation of two breast cancer cell lines with different metastatic potential and estrogen receptor status (MDA-MB-231 and MCF-7) and of one epithelial lung cancer cell line, namely A-549, was evaluated for concentrations ranging from 1 to 256μM and periods of treatment of 24, 48 and 72h. Both hybrids showed interesting and almost equipotent antiproliferative activities (IC50 64-70μM) for the MDA-MB-231 cell line after 24-48h of treatment, but they were more selective and much more potent (IC50 4-16μM) for the MCF-7 cells after 48h of treatment.
2.A new sesquiterpene lactone glycoside and a new quinic acid methyl ester from Patrinia villosa.
Yang YF1,2, Ma HM3, Chen G1,2, Wang HF1,2, Xiang Z4, Feng QM1,2, Hua HM1, Pei YH1. J Asian Nat Prod Res. 2016 May 7:1-7. [Epub ahead of print]
A new sesquiterpene lactone glycoside (1) and a new quinic acid methyl ester (2) were isolated from Patrinia villosa, together with another two known compounds chlorogenic acid n-butyl ester (3), 3, 4-di-O-caffeoylquinic acid methyl ester (4). Their structures were established using 1D/2D-NMR spectroscopy, mass spectrometry, and comparing with spectroscopic data reported in the literature.
3.Quantification of trace fatty acid methyl esters in diesel fuel by using multidimensional gas chromatography with electron and chemical ionization mass spectrometry.
Webster RL1,2, Rawson PM1,3, Evans DJ1, Marriott PJ2. J Sep Sci. 2016 May 9. doi: 10.1002/jssc.201600307. [Epub ahead of print]
Measurement of contamination of marine and naval diesel fuels (arising from product mixing or adulteration) with biodiesel or fatty acid methyl esters can be problematic, especially at very low levels. A suitable solution for this task for trace amounts of individual fatty acid methyl esters was resolution and quantification by using a multidimensional gas chromatographic approach with electron and chemical ionisation mass spectrometric detection. A unique column set comprising a 100 m methyl-siloxane non-polar first dimension column and high-temperature ionic liquid column in the second dimension enabled identification of individual fatty acid methyl esters at below the lowest concentrations required to be reported in a diesel fuel matrix. Detection limits for individual fatty acid methyl esters compounds ranged from 0.5 to 5.0 mg/L, with excellent linearity up to 5000 mg/L and repeatability of the method from 1.3-3.2%. The method was applied to the analysis of diesel fuel samples with suspected biodiesel contamination.
