• Title/Summary/Keyword: trans-cinnamic acid

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$TiO_2$-Mediated Photoreactions of Cinnamic Acid and Related Compounds in Methanol

  • Kim, Sung-Sik;Kim, Hyun-Jin;Lee, Hye-Jong;Park, Sang-Kyu
    • Journal of Photoscience
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    • v.10 no.2
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    • pp.181-184
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    • 2003
  • Photochemical reactions of some organic molecules on titanium dioxide were investigated in methanol. A methanolic solution of trans-cinnamic acid and titanium dioxide was irradiated with 300 nm UV lamps for 24 h to afford methyl cinnamate. In the case of trans-cinnamamide, the major product was found to be 3-phenylpropionamide, i.e., a saturation product of ethylenic double bond. However, irradiation of urocanic acid, caffeic acid, ethyl cinnamate, trans-chalcone, trans-cinnamonitrile, trans-stilbene or trans, trans-1,4-diphenyl-1,3-butadiene on titanium dioxide under the same conditions did not give any noticeable products. Meanwhile, when irradiated some aromatic aldehydes, such as trans-cinnamaldehyde, l-naphthaldehyde, and 2-naphthaldehyde in methanol, vicinal diols and alcohols derived from the diols were produced. On the other hand, irradiation of 9-anthraldehyde and titanium dioxide in methanol afforded only alcohols, in which diol was not observed.

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Conversion of trans-Cinnamic Acid to L-Phenylalanine by Phenylalanine Ammonia Lyase

  • Chang, Ji-Young;Goo, Yang-Mo;Lee, Chang-Hoon;Lee, Youn-Young;Kim, Kyoung-Ja
    • Bulletin of the Korean Chemical Society
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    • v.15 no.5
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    • pp.387-390
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    • 1994
  • The conversion of trans-cinnamic acid to phenylalanine using phenylalanine ammonia lyase (PAL) was examined. The optimum concentration of trans-cinnamic acid for the reaction was observed at 100 mM in cells and at 20 mM in cell free extracts, respectively. The production of L-phenylalanine was increased in both experiments as the concentration of ammonia was increased up to 10 M. The optimal pHs for the maximal conversion of trans-cinnamic acid to L-phenylalanine were 9.5 and 9.0 in experiments carried out with cells and with cell free extracts, respectively.

Reverse Reaction of L-Phenylalanine Ammonia-Lyase derived from Rhodotorula glutinis for the Production of L-Phenylalanine (Rhodotorula glutinis의 L-Phenylalanine Ammonia-Lyase의 역반응을 이용한 L-Phenylalanine 생성)

  • Kang, Bong-Kyung;Park, Jin-Young;Kiomin Chung
    • Microbiology and Biotechnology Letters
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    • v.15 no.2
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    • pp.80-83
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    • 1987
  • During the enzymatic production of L-phenylalanine exploiting L-phenylalanine ammonia lyase(E.C 4.3.1.5) and trans-cinnamic acid, the conversion yield of L-phenylalanine and the stability of L-phenylalanine ammonia-lyase per so or induced Rhodotorula glutinis IFO 0559 were investigated. And the glycerol added to the conversion reaction as stabilizer had effect only on L-phenylalanine and made it possible to obtain the 80% conversion yield from trans-cinnamic acid. In addition, the more rapid and reliable method than the thin layer chromatography for determining the conversion yield will be disscused.

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A New Analysis of p-Coumaric Acid and Trans-cinnamic Acid in Propolis By UPLC (UPLC를 이용한 프로폴리스 중 p-Coumaric Acid와 Trans-cinnamic Acid 분석법)

  • Kim, Se Gun;Hong, In Pyo;Woo, Soon Ok;Jang, Hye Ri;Han, Sang Mi
    • Korean Journal of Pharmacognosy
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    • v.47 no.2
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    • pp.186-191
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    • 2016
  • A new UPLC-DAD method for simultaneous determination of p-coumaric acid and trans-cinnamic acid in propolis was developed using Halo-C18 column and step gradient elution of MeCN and $0.1%H_3PO_4$ in 8 min. The method was validated by specificity, linearity, limit of detection, limit of quantification, precision(intra- and inter-day variability) and recovery tests. The validated method was sufficiently applicable for quantitative analysis of propolis products as well as propolis collected from different regions in Korea. The established method is simple, appropriate and efficient, and can be used for quality assessment of Korean propolis.

Inhibition of Fusarium oxysporum f. sp. nicotianae Growth by Phenylpropanoid Pathway Intermediates

  • Shull, Timothy E.;Kurepa, Jasmina;Miller, Robert D.;Martinez-Ochoa, Natalia;Smalle, Jan A.
    • The Plant Pathology Journal
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    • v.36 no.6
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    • pp.637-642
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    • 2020
  • Fusarium wilt in tobacco caused by the fungus Fusarium oxysporum f. sp. nicotianae is a disease-management challenge worldwide, as there are few effective and environmentally benign chemical agents for its control. This challenge results in substantial losses in both the quality and yield of tobacco products. Based on an in vitro analysis of the effects of different phenylpropanoid intermediates, we found that the early intermediates trans-cinnamic acid and para-coumaric acid effectively inhibit the mycelial growth of F. oxysporum f. sp. nicotianae strain FW316F, whereas the downstream intermediates quercetin and caffeic acid exhibit no fungicidal properties. Therefore, our in vitro screen suggests that trans-cinnamic acid and para-coumaric acid are promising chemical agents and natural lead compounds for the suppression of F. oxysporum f. sp. nicotianae growth.

Isolation and Characterization of Cinnamic Acid with Antimicrobial Activity from Needle of Pinus densiflora (솔잎에서 항미생물 활성을 갖는 Cinnamic Acid 의 분리 및 동정)

  • Kuk, Ju-Hee;Ma, Seung-Jin;Park, Keun-Hyung
    • Korean Journal of Food Science and Technology
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    • v.29 no.4
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    • pp.823-826
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    • 1997
  • The EtOAc extracts from needles of Pinus densiflora showed antimicrobial activities against bacteria, yeast and fungi. The antimicrobial principle was successively purified by solvent fractionation, silica gel adsorption column chromatography and Sephadex LH-20 column chromatography. The active substance was further purified by HPLC using $C_{18}$ column. The active substance was identified as trans-cinnamic acid by MS, $^{1}H-NMR\;and\;^{13}C-NMR$. The amount of cinnamic acid was $9.27\;{\mu}g$ Per gram of fresh needle of Pinus densiflora.

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Detection of Wound-inducible Trans-Cinnamic Acid-4-Hydroxylase in Avocado, Persea americana, Roots

  • Joo, Eun-Young
    • Preventive Nutrition and Food Science
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    • v.2 no.4
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    • pp.333-337
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    • 1997
  • Trans-cinnamic acid-4-hydroxylase(tC4H) is the first cytochrome P450-dependent monooxygenase of the phenylpropanoid pathway. The roots of avocado seedlings were wounded and examined to determine whether the tC4H would be activated in response to wounding and/or whether tC4H activity be modulated by the application of exogenous p-coumarate. At the specified length of times, the wounded and treated roots were either frozen in liquid nitrogen or used immediately to extract microsomal proteins. The microsomal proteins were subjected to immunoblot analysis using polyclonal antibodies against CYP73 of tC4H gene. In this study, tC4H was induced in wounded roots sealed in bags within 6 hours, and in low level({TEX}$10^{-8}${/TEX}M) of p-coumarate solution within 24 hours, whereas the olution without p-coumarate and high levels of p-coumarate solution repressed tC4H induction in wounded roots. These results indicate that tC4H is induced by wounding in the root of avocado, and is inhibited by the application of exogenous p-coumarate.

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Protective Effects of Cinnamic Acid Derivatives on Gastric Lesion

  • Lee, Sun Yi;Hwang, In Young;Jeong, Choon Sik
    • Natural Product Sciences
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    • v.23 no.4
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    • pp.299-305
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    • 2017
  • P-methoxycinnamic acid and 3,4,5-trimethoxycinnamic acid are the compounds found in Polygalae Radix, the root of Polygala tenuifolia Willdenow, and have been reported to have hepatoprotective and anti-neurodegenerative effects. On the other hand, there are no reports of their effects on gastric lesions. This study examined the inhibitory effects of cinnamic acids, including p-methoxycinnamic acid, 3,4,5-trimethoxycinnamic acid, and 8 compounds (cinnamic acid, 2-(trifluoromethyl) cinnamic acid, 3-(trifluoromethyl) cinnamic acid, trans-4-(trifluoromethyl) cinnamic acid, 4-(dimethylamino) cinnamic acid, 3,4-(methylenedioxy) cinnamic acid and 3,4-dihydroxycinnamic acid), which were selected based on their presence in medicinal herbs and molecular weight, against gastric lesions. Animal models were used to confirm the protective effects on acute gastritis caused by the administration of HCl/EtOH. Gastric acid inhibition was examined by an acid-neutralizing test and the proton pump ($H^+/K^+$-ATPase) inhibiting activity. In addition, antioxidant tests were performed and the gastric emptying rate was determined. The results showed that cinnamic acid, p-methoxycinnamic acid, and 3,4,5-trimethoxycinnamic acid had an inhibitory effect on gastric lesions.

Metabolic Fate of Phenylalanine in the Corn Smut Fungus Ustilago maydis (옥수수 깜부기균에 의한 페닐알라닌의 대사적 분해)

  • Hyun, Min-Woo;Kim, Seong-Hwan
    • The Korean Journal of Mycology
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    • v.39 no.3
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    • pp.249-253
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    • 2011
  • Cetecol has been known as a component of melanin in teliospores of the corn smut fungus Ustilago maydis. Its metabolic precursor has been assumed to be benzoic acid but it has not been proven yet. This study was carried out to verify the synthesis of benzoic acid and to chase its metabolic origin in U. maydis. For this aim, the catabolic process of phenylalanine was investigated by culturing the fungus in the complete medium containing L-$^{14}C$-phenylalanine and $^{14}C$-trans-cinnamic acid. We detected trans-cinnamic acid, benzoic acid, 4-hydroxybenzoic acid and hydroxybenzoic acid derivatives from the extracts of the fungus cells and cultural filtrates by thin layered chromatography analysis. We also observed that the fungus could completely catabolize L-$^{14}C$-phenylalanine and produce $^{14}CO_2$ in the air. Conclusively, this study provided an evidence that U. maydis could produce benzoic acid through catabolic process of phenylalanine.