sinapyl-alcohol and cinnamyl-alcohol

A series of 25 selected oxyprenylated natural phenylpropanoids were synthesized, and their growth inhibitory activities were evaluated in vitro together with 14 other commercially available non-alkylated compounds belonging to the same chemical series. The compounds were tested on six human cancer cell lines using MTT colorimetric assays. The data reveal that of the six chemical groups (G) studied, coumarins (G1), cinnamic and benzoic acids (G2), chalcones (G3), acetophenones (G4), anthraquinones (G5), and cinnamaldehydes and cinnamyl alcohols (G6), G2-related compounds displayed the weakest growth inhibitory activities in vitro, whereas G5-related compounds displayed the highest activities. Quantitative videomicroscopy analyses were then carried out on human U373 glioblastoma cells, which are characterized by various levels of resistance to different pro-apoptotic stimuli. These analyses revealed that compounds 20 (4,2',4'-trihydroxychalcone), and 30 and 31 (two cinnamaldehydes) were cytostatic and able to overcome the intrinsic resistance of U373 cancer cells to pro-apoptotic stimuli.

Topics: Acetophenones; Acrolein; Anthraquinones; Antineoplastic Agents; Apoptosis; Benzoates; Biological Products; Cell Line, Tumor; Chalcones; Cinnamates; Coumarins; Drug Screening Assays, Antitumor; Humans; Prenylation; Propanols

Two methyl esters of fatty acids, namely octadecanoic acid methyl ester (methyl stearate) and hexadecanoic acid methyl ester (methyl palmitate), in addition to four cinnamyl alcohol derivatives, sinapyl alcohol, coniferyl alcohol, p-coumaryl alcohol and coniferyl alcohol 4-O-glucoside (coniferin), were isolated from callus cultures of Wedelia prostrata. The structure of coniferin was established by spectroscopic and chemical methods, while the other compounds were identified by gas chromatography-mass spectrometry and thin layer chromatography in comparison with standards.

Topics: Cell Culture Techniques; Chromatography, Thin Layer; Cinnamates; Coumaric Acids; Esters; Gas Chromatography-Mass Spectrometry; Methanol; Palmitates; Phenols; Phenylpropionates; Plant Shoots; Propanols; Propionates; Stearates; Wedelia

The thermochemolytic behavior of 4-O-etherified cinnamyl alcohols and aldehydes in lignin was investigated in the presence of tetramethylammonium hydroxide (TMAH) (315 degrees C/4 s), using veratrylglycol-beta-(coniferyl alcohol) ether (1a), veratrylglycol-beta-(sinapyl alcohol) ether (1b), and veratrylglycol-beta-(coniferyl aldehyde) ether (2). The methylated products were monitored with gas chromatography-mass spectrometry. Dimers 1a and 1b provided the coniferyl and sinapyl alcohol dimethyl ethers consisting of three isomers, respectively. Coniferyl alcohol dimethyl ether isomers were also observed in the TMAH thermochemolysis pyrolysates of a bulk dehydrogenation polymer of coniferyl alcohol and a Japanese cedar (Cryptomeria japonica) wood. Coniferyl aldehyde methyl ether was not provided from TMAH thermochemolyses of coniferyl aldehyde, 2, a dehydrogenation polymer of coniferyl aldehyde, and the cedar wood. The former three provided veratryl aldehyde in a large abundance, instead of coniferyl aldehyde methyl ether. Sinapyl aldehyde provided 3,4,5-trimethoxybenzaldehyde in a large abundance and sinapyl aldehyde methyl ether in a trace abundance. The results showed that TMAH thermochemolysis is an effective tool to obtain information on cinnamyl alcohol end groups, but is not applicable to analysis of cinnamyl aldehyde end groups.

Topics: Acrolein; Aldehydes; Dimerization; Ethers; Gas Chromatography-Mass Spectrometry; Lignin; Methylation; Phenols; Phenylpropionates; Propanols; Quaternary Ammonium Compounds; Tracheophyta; Wood