66648-43-9Relevant articles and documents
Lipase catalysed synthesis of N-trans-feruloyltyramine and a quantitative HPLC-UV method for analysis
Alrub, Mohammad Abu,Basri, Mahiran,Malek, Emilia Abd,Alang Ahmad, Shahrul Ainliah,Abdul Rahman, Mohd Basyaruddin,Salleh, Abu Bakar
, p. 385 - 390,6 (2012)
N-trans feruloyltyramine amide was successfully synthesized from 4-hydroxy-3-methoxycinnamic acid and tyramine hydrochloride in a one-step lipase catalysed reaction. The use of immobilized lipase, lipozyme TL IM as the catalyst in the reaction allowed simple isolation of the enzyme from the products and other components in the reaction mixture. N-feruloyltyramine amide was characterized using Fourier Transform Infrared (FTIR) Spectroscopy, Proton Nuclear Magnetic Resonance (1H NMR) and elemental analysis. Under optimized conditions 93.5% yield was obtained when the process was carried out for 48 h using a molar ratio of cinnamic acid:tyramine HCl, 6:1 at 40°C. In addition, a rapid simple and sensitive HPLC-UV method was developed for the determination of N-feruloyltyramine using an Rp-8 endcapped column. The optimum mobile phase used was acetonitrile:disodium hydrogen phosphate, 30:70(v/v.). N-feruloyltyramine amide was detected at a retention time of 12 min. The calibration curve was linear over the range of 5.2712.30 × 10-4 M with correlation factor r 0.9958. Consequently, the method was considered valid for quantitative analysis samples of N-trans-feruloyltyramine amide.
Identification and quantification of potential anti-inflammatory hydroxycinnamic acid amides from wolfberry
Wang, Siyu,Suh, Joon Hyuk,Zheng, Xi,Wang, Yu,Ho, Chi-Tang
, p. 364 - 372 (2017/12/01)
Wolfberry or Goji berry, the fruit of Lycium barbarum, exhibits health-promoting properties that leads to an extensive study of their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized LC-MS/MS and NMR analysis, nine amide compounds were identified from the fruits. Seven of these compounds were identified in this plant for the first time. The amide compounds with a tyramine moiety were the most abundant. In vitro studies indicated that five HCCA compounds showed inhibitory effect on NO production inuded by lipopolysaccharides with IC50 less than 15.08 μM (trans-N-feruloyl dopamine). These findings suggested that wolfberries demonstrated anti-inflammatory properties.
Study of the UV light conversion of feruloyl amides from Portulaca oleracea and their inhibitory effect on IL-6-induced STAT3 activation
Hwang, Joo Tae,Kim, Yesol,Jang, Hyun-Jae,Oh, Hyun-Mee,Lim, Chi-Hwan,Lee, Seung Woong,Rho, Mun-Chual
supporting information, (2016/08/02)
Two new feruloyl amides, N-cis-hibiscusamide (5) and (7′ S)-N-cis-feruloylnormetanephrine (9), and eight known feruloyl amides were isolated from Portulaca oleracea L. and the geometric conversion of the ten isolated feruloyl amides by UV light was verified. The structures of the feruloyl amides were determined based on spectroscopic data and comparison with literature data. The NMR data revealed that the structures of the isolated compounds showed cis/trans-isomerization under normal laboratory light conditions. Therefore, cis and trans-isomers of feruloyl amides were evaluated for their convertibility and stability by UV light of a wavelength of 254 nm. After 96 h of UV light exposure, 23.2%-35.0% of the cis and trans-isomers were converted to trans-isomers. Long-term stability tests did not show any significant changes. Among all compounds and conversion mixtures collected, compound 6 exhibited the strongest inhibition of IL-6-induced STAT3 activation in Hep3B cells, with an IC50 value of 0.2 μM. This study is the first verification of the conversion rates and an equilibrium ratio of feruloyl amides. These results indicate that this natural material might provide useful information for the treatment of various diseases involving IL-6 and STAT3.