- Lipase catalysed synthesis of N-trans-feruloyltyramine and a quantitative HPLC-UV method for analysis
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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.
- Alrub, Mohammad Abu,Basri, Mahiran,Malek, Emilia Abd,Alang Ahmad, Shahrul Ainliah,Abdul Rahman, Mohd Basyaruddin,Salleh, Abu Bakar
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- 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
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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.
- Takao, Koichi,Toda, Kazuhiro,Saito, Takayuki,Sugita, Yoshiaki
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p. 1020 - 1027
(2017/11/17)
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- Identification and quantification of potential anti-inflammatory hydroxycinnamic acid amides from wolfberry
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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.
- Wang, Siyu,Suh, Joon Hyuk,Zheng, Xi,Wang, Yu,Ho, Chi-Tang
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p. 364 - 372
(2017/12/01)
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- Dihydrobenzofuran Neolignanamides: Laccase-Mediated Biomimetic Synthesis and Antiproliferative Activity
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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.
- Cardullo, Nunzio,Pulvirenti, Luana,Spatafora, Carmela,Musso, Nicolò,Barresi, Vincenza,Condorelli, Daniele Filippo,Tringali, Corrado
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p. 2122 - 2134
(2016/09/09)
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- Study of the UV light conversion of feruloyl amides from Portulaca oleracea and their inhibitory effect on IL-6-induced STAT3 activation
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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.
- Hwang, Joo Tae,Kim, Yesol,Jang, Hyun-Jae,Oh, Hyun-Mee,Lim, Chi-Hwan,Lee, Seung Woong,Rho, Mun-Chual
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supporting information
(2016/08/02)
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- Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides
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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.
- Georgiev, Lyubomir,Chochkova, Maya,Totseva, Iskra,Seizova, Katya,Marinova, Emma,Ivanova, Galya,Ninova, Mariana,Najdenski, Hristo,Milkova, Tsenka
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p. 4173 - 4182
(2013/09/02)
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- The development of a general strategy for the synthesis of tyramine-based natural products by using continuous flow techniques
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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.
- Achanta, Srinivas,Liautard, Virginie,Paugh, Robert,Organ, Michael G.
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supporting information; experimental part
p. 12797 - 12800
(2011/02/22)
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- Induction of adiponectin by natural and synthetic phenolamides in mouse and human preadipocytes and its enhancement by docosahexaenoic acid
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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.
- Yamazaki, Yoshimitsu,Kawano, Yasuhiro,Uebayasi, Masami
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p. 290 - 300
(2008/09/16)
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- PARA-COUMARIC ACID OR PARA-HYDROXYCINNAMIC ACID DERIVATIVES AND THEIR USE IN COSMETIC OR DERMATOLOGICAL COMPOSITIONS
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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
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Page/Page column 7
(2010/11/28)
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- Analogues of N-hydroxycinnamoylphenalkylamides as inhibitors of human melanocyte-tyrosinase
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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.
- Okombi, Sabrina,Rival, Delphine,Bonnet, Sebastien,Mariotte, Anne-Marie,Perrier, Eric,Boumendjel, Ahcene
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p. 2252 - 2255
(2007/10/03)
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- Synthesis of amide compounds of ferulic acid, and their stimulatory effects on insulin secretion in vitro
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We prepared amide compounds which were derived from ferulic acid using various amines, and investigated their stimulatory effects on insulin secretion using rat pancreatic RIN-5F cells. Most of these compounds exhibited significant promotion of the insulin-release at a concentration of 10 μM and in particular, the amides having n-butyl, n-pentyl, pyrrolidine, and piperidine groups showed high activity.
- Nomura, Eisaku,Kashiwada, Ayumi,Hosoda, Asao,Nakamura, Kozo,Morishita, Hideko,Tsuno, Takuo,Taniguchi, Hisaji
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p. 3807 - 3813
(2007/10/03)
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- Induction of N-hydroxycinnamoyltyramine synthesis and tyramine N-hydroxycinnamoyltransferase (THT) activity by wounding in maize leaves
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Both N-p-coumaroyl-and N-feruloyltyramine accumulated in response to wounding in leaf segments of maize. The amount of N-hydroxycinnamoyltyramines started to increase 3-6 h after wounding and peaked at 12 h. Thereafter, the amount of N-p-coumaroyltyramine decreased rapidly, while the N-feruloyltyramine content remained at a high level. The accumulation of N-hydroxycinnamoyltyramines was accompanied by an increase in the tyramine N-hydroxycinnamoyltransferase (THT) activity. This increase was initially detected 3 h after wounding and reached a maximum at 36 h, the level of activity being 40 and 11 times that in the leaves before wounding and in the control leaves, respectively. Partial purification of THT from wounded leaves by (NH4)2SO4 precipitation and subsequent two steps of anion-exchange chromatography resulted in a 12.5-fold increase in specific activity. Kinetic studies with this partially purified enzyme revealed that the best substrates were tyramine and feruloyl-CoA, although tryptamine and sinapoyl-CoA also efficiently served as substrates. The apparent native molecular weight of the enzyme was determined by gel filtration as 40 kDa.
- Ishihara, Atsushi,Kawata, Naoki,Matsukawa, Tetsuya,Iwamura, Hajime
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p. 1025 - 1031
(2007/10/03)
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- Formation of hydroxycinnamoylamides and α-hydroxyacetovanillone in cell cultures of Solanum khasianum
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In elicitor-elicited photomixotrophic Solanum khasianum cell cultures, nine phenolic compounds accumulated in the cell culture medium. They were isolated and structurally identified at the cis- and trans-isomers of N-p- coumaroyloctopamine, N-feruloyloctopamine, N-p-coumaroyltyramine and N- feruloyltyramine as well as α-hydroxyacetovanillone. The cis-isomers of the hydroxycinnamoyl moieties were only formed during illumination of the cultures. The hydroxycinnamoylamides showed a transient accumulation with maximum values between 6 and 24 hr after elicitation, depending on the compound. The decrease of the compounds is very likely a peroxidase-mediated reaction.
- Muehlenbeck, Ute,Kortenbusch, Albertus,Barz, Wolfgang
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p. 1573 - 1579
(2007/10/03)
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- TERMITE ANTIFEEDANT ACTIVITY IN XYLOPIA AETHIOPICA
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A heaxne extract of xylopia aethiopica fruits and an aqueous methanol extract of the seeds were studied for termite antifeedant activity against workers of the subterranean termite, Reticullitermes speratus.The crude extract, at1percent exhibited strong antifeedant activity in a choice filter paper disk bioassay.Bioassay-directed fractionation led to the isolation and identification of six ent-kaurane diterpenes in the hexane extract.Feeding deterrent activity varied significantly with the structures when the compounds were tested at concentrations ranging from 5000 ppm (40 μg cm-2) to 100 ppm (0.824 μg cm-2). (-)-Kaur-16-en-19-oic acid had the strongest termite antifeedants activity among the ent-kauranes isolated.Two phenolic amides and four lignanamides were also isolated from the aqueous methanolic extract of seeds.E-3-(4-hydroxy-3-methoxyphenyl)-N-2-2-propenamide was more active than E-3 (3,4-dihydroxyphenyl)-N-2-2-propenamide, whilst grossamide and the new lignanamide, demethylgrossamide, as well as (-)-cannabisins B and D exhibited potent feeding deterrent activity at 5000 ppm.The identity of these compounds was established by spectroscopic analysis and synthesis.Two synthetic amides, E-3-(3,4-methylenedioxyphenyl)-N-2- propenamide and E-3-(3,4-methylenedioxyphenyl)-N-2--2-propenamide were also tested for antifeedant activity. - Keywords: xylopia aethiopica; Annonaceae; seeds; fruits; Reticullitermes speratus; Isoptera; antifeedants; ent-kaurane diterpenes; phenolic amides; lignanamides.
- Lajide, Labunmi,Escoubas, Pierre,Mizutani, Junya
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p. 1105 - 1112
(2007/10/02)
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- Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives
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N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to M essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC50 value was 2.3 nM in our assay system, in which an IC50 value of AA 861, a specific inhibitor of 5-lipoxygenase, was 8 nM.
- Tseng,Iwakami,Mikajiri,Shibuya,Hanaoka,Ebizuka,Padmawinata,Sankawa
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p. 396 - 400
(2007/10/02)
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- CANNABISIN A, AN ARYLNAPHTHALENE LIGNANAMIDE FROM FRUITS OF CANNABIS SATIVA
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A new lignanamide, named cannabisin A, a known lignanamide, grossamide, and three known amides, N-trans-caffeoyltyramine, N-trans-feruloyltyramine, N-p-coumaroyltyramine, were isolated from the fruits of Cannabis sativa.The structure of cannabisin A has been established as 6,7-dihydroxy-1-(3,4-dihydroxyphenyl)-N1,N2-bis--2,3-naphthalenedicarboxamide, on the basis of chemical and spectral evidence.Key Word Index - Cannabis sativa; Cannabidaceae; fruits; cannabisin A; grossamide; N-trans-caffeoyltyramine; N-trans-feruloyltyramine; N-p-coumaroyltyramine.
- Sakakibara, Iwao,Katsuhara, Takao,Ikeya, Yukinobu,Hayashi, Koji,Mitsuhashi, Hiroshi
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p. 3013 - 3016
(2007/10/02)
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- A PHENOLIC AMIDE FROM ACTINODAPHNE LONGIFOLIA
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Further examination of Actinodaphne longifolia has led to the isolation of a new phenolic amide, N-trans-feruloyl 3-methyldopamine, along with N-trans-feruloyl tyramine.The structure of this compound was elucidated by spectroscopic and chemical means.Key Word Index - Actinodaphne longifolia; Lauraceae; N-trans-feruloyl 3-methyldopamine; N-trans-feruloyl tyramine; phenolic amide.
- Tanaka, Hitoshi,Nakamura, Takeshi,Ichino, Kazuhiko,Ito, Kazuo
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p. 2516 - 2517
(2007/10/02)
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- A New Lignan Amide, Grossamide, from Bell Pepper (Capsicum annuum var. grossum)
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Two new phenolic amides, grossamide (7) and N-cis-feruloyl tyramine (2), have been isolated from the roots of bell pepper (Capsicum annuum var. grossum) together with p-aminobenzaldehyde (1), N-trans-feruloyl tyramine (3), N-trans-p-coumaroyl tyramine (4), N-trans-feruloyl octopamine (5), and N-trans-p-coumaroyl octopamine.
- Yoshihara, Teruhiko,Yamaguchi, Katsuyoshi,Takamatsu, Seiji,Sakamura, Sadao
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p. 2593 - 2598
(2007/10/02)
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- Structures and Syntheses of Two Phenolic Amides from Piper nigrum L.
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Two phenolic amides were isolated from the fruits of white pepper (Piper nigrum L.) and identified to be N-trans-feruloyl tyramine (2a) and N-5-(4-hydroxyphenyl)-2E,4E-pentadienoyl piperidine (6a) on the basis of chemical and spectral evidence.Both compounds were synthesized.
- Nakatani, Nobuji,Inatani, Reiko,Fuwa, Hidetsugu
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p. 2831 - 2836
(2007/10/02)
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