66648-43-9Relevant academic research and scientific papers
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.
Synthesis of amide and ester derivatives of cinnamic acid and its analogs: Evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities
Takao, Koichi,Toda, Kazuhiro,Saito, Takayuki,Sugita, Yoshiaki
, p. 1020 - 1027 (2017/11/17)
A series of cinnamic acid derivatives, amides (1–12) and esters (13–22), were synthesized, and structure–activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1–10, 12–18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxy-indole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9–11, 15, 17–22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer’s disease.
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.
Dihydrobenzofuran Neolignanamides: Laccase-Mediated Biomimetic Synthesis and Antiproliferative Activity
Cardullo, Nunzio,Pulvirenti, Luana,Spatafora, Carmela,Musso, Nicolò,Barresi, Vincenza,Condorelli, Daniele Filippo,Tringali, Corrado
, p. 2122 - 2134 (2016/09/09)
The biomimetic synthesis of a small library of dihydrobenzofuran neolignanamides (the natural trans-grossamide (4) and the related compounds 21-28) has been carried out through an eco-friendly oxidative coupling reaction mediated by Trametes versicolor laccase. These products, after complete spectroscopic characterization, were evaluated for their antiproliferative activity against Caco-2 (colon carcinoma), MCF-7 (mammary adenocarcinoma), and PC-3 (prostate cancer) human cells, using an MTT bioassay. The racemic neolignamides (±)-21 and (±)-27, in being the most lipophilic in the series, were potently active, with GI50 values comparable to or even lower than that of the positive control 5-FU. The racemates were resolved through chiral HPLC, and the pure enantiomers were subjected to ECD measurements to establish their absolute configurations at C-2 and C-3. All enantiomers showed potent antiproliferative activity, with, in particular, a GI50 value of 1.1 μM obtained for (2R,3R)-21. The effect of (±)-21 on the Caco-2 cell cycle was evaluated by flow cytometry, and it was demonstrated that (±)-21 exerts its antiproliferative activity by inducing cell cycle arrest and apoptosis.
Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides
Georgiev, Lyubomir,Chochkova, Maya,Totseva, Iskra,Seizova, Katya,Marinova, Emma,Ivanova, Galya,Ninova, Mariana,Najdenski, Hristo,Milkova, Tsenka
, p. 4173 - 4182 (2013/09/02)
Synthetic hydroxycinnamoylamides of amino acids (precursors of aromatic amines) were studied for their antioxidant activity in vitro by two antioxidant assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibition of lipid peroxidation (LPO). Furthermore, these compounds were tested and compared with their corresponding cinnamoylamides of aromatic amines for their inhibitory activity using mushroom tyrosinase. In addition, five hydroxycinnamoyl amino acid amides were investigated for their antimicrobial effect. Structure-activity relationships analysis disclosed that the presence of catechol rest at amino acid or at benzene moieties of substituted cinnamic acid amides significantly scavenged DPPH radical and inhibited LPO. The results obtained by LPO clearly expressed the positive influence of indole moiety on the activity. Moreover, the existence of p-hydroxy substituted cinnamic acid moiety leads to better tyrosinase inhibition. Amongst the tested compounds, amides of p-coumaroyldopamine or tyramine and their corresponding amino acid precursors are the most potent tyrosinase inhibitors.
The development of a general strategy for the synthesis of tyramine-based natural products by using continuous flow techniques
Achanta, Srinivas,Liautard, Virginie,Paugh, Robert,Organ, Michael G.
supporting information; experimental part, p. 12797 - 12800 (2011/02/22)
A flowing future! A multistep, general flow chemistry protocol has been developed for the preparation of tyramine-based natural products. The process integrates room-temperature reactions with high-temperature Heck coupling reactions, where the heat has been supplied by microwave irradiation. As a proof of concept for 'scaling out' to attain larger quantities of the desired products, the four primary tyramine-based natural products were prepared on a gram scale using this synthetic protocol.
Induction of adiponectin by natural and synthetic phenolamides in mouse and human preadipocytes and its enhancement by docosahexaenoic acid
Yamazaki, Yoshimitsu,Kawano, Yasuhiro,Uebayasi, Masami
, p. 290 - 300 (2008/09/16)
Adiponectin, the adipose-derived cytokine, plays an important role in preventing metabolic syndromes. To develop new adiponectin inducers, eight species of ferulic esters and amides, and five related compounds were synthesized and tested on the stimulation of adiponectin production in mouse 3T3-L1 and normal human preadipocytes. The ferulamides with an aromatic ring in the N-substituent are very active in inducing adiponectin as compared with the known active compounds, curcumin, [6]-gingerol, and capsaicin, and furthermore the activities of these ferulamides are remarkably stronger than those of the corresponding esters or the straight chain octylamide. The most active compound, N-(2-phenylethyl)ferulamide (7), was found to activate the PPAR (peroxisome proliferator-activated receptor) γ-RXR (retinoid X receptor) α heterodimeric complex in the PPRE (PPAR-responsive element)-driven luciferase reporter assay. The adiponectin production by 7 is synergistically enhanced by coaddition of a PPARγ-specific agonist, pioglitazone (PGZ), or another PPARγ agonist, docosahexaenoic acid (DHA), in cultured preadipocytes. The compound 7 alone did not show a statistically significant effect on the plasma adiponectin level in KK-Ay/Ta mice, while 1% 7 in the diets significantly lowered the blood glucose and triglyceride levels and 0.3% 7 mixed with DHA oil in the diets significantly increased the adiponectin level as compared with the control. These results suggest that the present ferulamides would be useful lead compounds in developing more potent agents for treatment of metabolic syndromes through promoting the endogenous adiponectin production, and that such an activity is possibly enhanced by the coadministration with DHA.
PARA-COUMARIC ACID OR PARA-HYDROXYCINNAMIC ACID DERIVATIVES AND THEIR USE IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS
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Page/Page column 7, (2010/11/28)
The invention relates to the use of para-coumaric acid or para-hydroxycinnamic acid derivatives in cosmetic or derma-tological compositions, specifically to the use of at least one compound derived from para-coumaric acid having a general formula (I) below: in which, especially, Z represents an oxygen or an -NH- group; X and Y are identical and each represent a CH or CH2 group, as an active principle with depigmenting, free-radical- scavenging and/or antiinflammatory activity. The invention also relates to the use of the above compounds for cosmetic care or for the preparation of a pharmaceutical composition, especially for depigmenting an area of skin, having antiradi-cal and/or antiinflammatory activity
Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase
Okombi, Sabrina,Rival, Delphine,Bonnet, Sebastien,Mariotte, Anne-Marie,Perrier, Eric,Boumendjel, Ahcene
, p. 2252 - 2255 (2007/10/03)
Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin synthesis, catalyzing the transformation of tyrosine to l-dopaquinone. The aim of the present study was to study molecules able to inhibit melanin synthesis through inhibition of tyrosinase and their potential use in treating pigmentation-related disorders. We targeted amides obtained from coupling p-hydroxycinnamic acid derivatives with phenylalkylamines. The biological activity was evaluated on human melanocytes by an assay which measures tyrosine-catalyzed l-Dopa oxidation. The most active amides were: trans-N-caffeoyltyramine, N-dihydrocaffeoyltyramine, and trans-N-dihydro-p- hydroxycinnamoyltyramine which induce complete inhibition at 0.1 mM. At the latter concentration, kojic acid, which was used as the reference inhibitor, was inactive.
