• Title/Summary/Keyword: p-Coumaric acid

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p-Coumaric Acid Potently Down-regulates Zebrafish Embryo Pigmentation: Comparison of in vivo Assay and Computational Molecular Modeling with Phenylthiourea

  • Kim, Dong-Chan;Kim, Seonlin;Hwang, Kyu-Seok;Kim, Cheol-Hee
    • Biomedical Science Letters
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    • v.23 no.1
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    • pp.8-16
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    • 2017
  • p-Coumaric acid is an organic compound that is a hydroxyl derivative of cinnamic acid. Due to its multiple biological activities p-coumaric acid has been widely studied in biochemical and cellular systems and is also considered as a useful therapeutic candidate for various neuronal diseases. However, the efficacy of p-coumaric acid on zebrafish developmental regulation has not been fully explored. In this study, therefore, we first investigated the action mechanism of the p-coumaric acid on the zebrafish development in a whole-organism model. p-Coumaric acid treated group significantly inhibited the pigmentation of the developing zebrafish embryos compared with control embryos without any severe side effects. In addition, p-coumaric acid down-regulated more effectively in a lower concentration than the well-known zebrafish's melanogenic inhibitor, phenylthiourea. We also compared the molecular docking property of p-coumaric acid with phenylthiourea on the tyrosinase's kojic acid binding site, which is the key enzyme of zebrafish embryo pigmentation. Interestingly, p-coumaric acid interacted with higher numbers of the amino acid residues and exhibited a tight binding affinity to the enzyme than phenylthiourea. Taken all together, these results strongly suggest that p-coumaric acid inhibits the activity of tyrosinase, consequently down-regulating zebrafish embryo pigmentation, and might play an important role in the reduction of dermal pigmentation. Thus, p-coumaric acid can be an effective and non-toxic ingredient for anti-melanogenesis functional materials.

Antimicrobial Activity of Extracts and Coumaric Acid Isolated from Artemisia princeps var. orientalis (쑥의 추출물 및 Coumaric Acid의 항균활성)

  • 박석규;박종철
    • KSBB Journal
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    • v.9 no.5
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    • pp.506-511
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    • 1994
  • Antimicrobial activity of methanol extract and fraction from mugwort leaves(Artemisia princeps val. orientalis) was investigated for the screening of natural antiwucroblal components. By using agar diffusion method, ethyl acetate(EtOAc) layer fractionated from methanol extract of mugwort leaves showed the highest inhibitory effects against tested microorganisms. The ortho-coumaric acid(200∼600ppm) isolated from EtOAc layer showed strong antibacterial activities for Bacillus subtilis and Salmonella typhimurium. As derivatives of o-coumaric acid, antibacterial activity of para-coumaric acid was 1.2∼1.7 fold higher than that of o-coumaric acid. Three types of coumaric acids strong inhibited the growth of B. subtilis in the culture medium. Growth of S. tyhimurium, P. aeruginosa and S. aureus were effectively inhibited by o-, m- and p-coumaric acids, respectively. Minimum inhibitory dose of p-coumaric acid for B. subtilis was $\100∼200mu\textrm{g}$/paper disk.

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Activation of Pro-Apoptotic Multidomain Bcl-2 Family Member Bak and Mitochondria-Dependent Caspase Cascade are Involved in p-Coumaric Acid-Induced Apoptosis in Human Jurkat T Cells (p-Coumaric acid에 의해 유도되는 인체 Jurkat T 세포의 에폽토시스 기전)

  • Lee, Je-Won;Kim, Young-Ho
    • Journal of Life Science
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    • v.21 no.12
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    • pp.1678-1688
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    • 2011
  • The apoptogenic effect of p-coumaric acid, a phenolic acid found in various edible plants, on human acute leukemia Jurkat T cells was investigated. Exposure of Jurkat T cells to p-coumaric acid (50-$150{\mu}M$) caused cytotoxicity and TdT-mediated dUTP nick-end labeling (TUNEL)-positive apoptotic DNA fragmentation along with Bak activation, ${\Delta}{\psi}m$ loss, activation of caspase-9, -3, -7, and -8, and PARP degradation in a dose-dependent manner. However,these apoptotic events were completely abrogated in Jurkat T cells overexpressing Bcl-2.Under these conditions, necrosis was not accompanied. Pretreatment of the cells with the pan-caspase inhibitor (z-VAD-fmk) could prevent p-coumaric acid-induced sub-$G_1$ peak representing apoptotic cells, whereas it failed to block ${\Delta}{\psi}m$ loss, indicating that the activation of caspase cascade was prerequisite for p-coumaric acid-induced apoptosis as a downstream event of ${\Delta}{\psi}m$ loss. FADD- and caspase-8-positive wild-type Jurkat T cell clone A3, FADD-deficient Jurkat T cell clone I2.1, and caspase-8-deficient Jurkat T cell clone I9.2 exhibited similar susceptibilities to the cytotoxicity of p-coumaric acid, excluding an involvement of Fas/FasL system in triggering the apoptosis. The apoptogenic activity of p-coumaric acid is more potent in malignant Jurkat T cells than in normal human peripheral T cells. Together, these results demonstrated that p-coumaric acid-induced apoptogenic activity in Jurkat T cellswas mediated by Bak activation, ${\Delta}{\psi}m$ loss, and subsequent activation of multiple caspases such as caspase-9, -3, -7, and-8, and PARP degradation, which could be regulated by anti-apoptotic protein Bcl-2.

Differential Effects of Methoxylated p-Coumaric Acids on Melanoma in B16/F10 Cells

  • Yoon, Hoon Seok;Lee, Nam-Ho;Hyun, Chang-Gu;Shin, Dong-Bum
    • Preventive Nutrition and Food Science
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    • v.20 no.1
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    • pp.73-77
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    • 2015
  • As an approach to search for chemopreventive agents, we tested p-coumaric acid, 3-methoxy-p-coumaric acid (ferulic acid), and 3,5-dimethoxy-p-coumaric acid (sinapic acid) in B16/F10 melanoma cells. Intracellular melanin contents were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay and cytotoxicity of the compounds were examined by lactate dehydrogenase (LDH) release. p-Coumaric acid showed inhibitory effect on melanogenesis, but ferulic acid increased melanin content, and sinapic acid had almost no effect on melanogenesis. Treatment with ferulic acid resulted in a 2 to 3 fold elevation in the production of melanin. Correlatively, cell viability decreased in a dose-dependent manner when treated with ferulic acid. However, ferulic acid did not affect the LDH release from the cells. Treatment with sinapic acid resulted in a 50~60% elevation in the release of LDH when treated with a $200{\mu}g/mL$ concentration and showed neither cytostasis nor increase of melanin synthesis in a dose-dependent manner. Taken together, p-coumaric acid inhibits melanogenesis, ferulic acid induces melanogenesis, and sinapic acid exerts cytotoxic effects in B16/F10 murine melanoma cells. The results indicate that the addition of methoxy groups to p-coumaric acid shows the melanogenic or cytotoxic effects in melanoma cells compared to the original compound. Therefore, this study suggests the possibility that methoxylated p-coumaric acid, ferulic acid can be used as a chemopreventive agent.

Assessment of Allelopathic Potentiality and Identification of Allelopathic Compounds on Korean Local Rice Varieties

  • Chung, Ill-Min;Ahn, Joung-Kuk;Kim, Jung-Tae;Kim, Choon-Song
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.45 no.1
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    • pp.44-49
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    • 2000
  • This study was conducted to assess the allelopathic potentiality of Korea traditional seventy-nine rice (Oryza sativa L.) cultivars on barnyardgrass (Echinochloa crus-galli P. Beauv. var. oryzicola Ohwi) and to identify possible allelopathic compounds from selected rice cultivars, such as Seogandodobyeo, Huadobyeo and Heugbalbyeo. In the straw mixture, Seogandodobyeo showed the greatest inhibition (67.07%) on total emergence percentage. The greatest inhibition on total seedling length and dry weight of barnyardgrass occurred in Huadobyeo (58.32 %) and Heugbalbyeo (81.20%), respectively. An HPLC analysis with nine standard compounds showed that the concentrations and compositions of allelopathic compound depend upon the cultivars. Four compounds including Ο-coumaric acid in Seogandodobyeo extracts, four compounds including p-coumaric acid in Huadobyeo extracts, and seven compounds including Ο-coumaric acid in Heugbalbyeo were detected, respectively. Ο-coumaric acid (0.97 mg/g) in Seogandodobyeo, p-coumaric acid (0.92mg/g) in Huadobyeo and Ο-coumaric acid (1.02 mg/g) in Heugbalbyeo was detected as the highest amounts, respectively. The preliminary identification by HPLC analysis resulted in peaks with retention times close to those of standards which were confirmed with EI/MS. The mass spectra of p-coumaric, and Ο-coumaric acids showed molecular ions (m/z) at 164 and 164, and their base peaks (m/z) at 164 and 118, respectively.

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Identification of phenolic antioxidative components in Terminalia Chebula Retz (가자 항산화성 물질의 분리 및 확인)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Applied Biological Chemistry
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    • v.36 no.4
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    • pp.239-243
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    • 1993
  • Chemical structures of phenolic antioxidative components of defatted Terminalia chebula R. were elucidated by used MS and H-NMR. The results showed that the phenolic antioxidative components were identified as ferulic acid, vanillic acid, p-coumaric acid in free-acid extracts, and caffecic acid, vanillic acid and p-coumaric acid in soluble-acid extracts, and caffeic acid, phloroglucinol and pyrogallol in insoluble-bound extracts, respectively.

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Free Radicals Scavenging Activity of Bulro Kugi (Lycium chinense Mill) Fruit, Leaf and Root (불로 구기 부위별 자유라디칼 소거효과에 관한 연구)

  • Kim, Eun-Hae;Kim, Hyeon-Wee;Kim, Su-Dong;Lee, Bo-Hee;Lee, Cherl-Ho;Koh, Kyung-Hee
    • Korean Journal of Food Science and Technology
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    • v.37 no.1
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    • pp.6-10
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    • 2005
  • Free radical-scavenging activities of Korean Bulro Kugi (Lycium chinense Mill) fruit, leaf, and root were evaluated. Total phenolic contents of fruit, leaf, and root were $1,078.4{\pm}61.0$, $939.9{\pm}19.8$, and $3,792.2{\pm}106.6mg/L$, and their flavonoids were $396.7{\pm}15.2$, $1,952.9{\pm}21.3$, and $425.3{\pm}13.5mg/L$, respectively (p<0.001). HPLC revealed main polyphenolic compounds in fruit were p-coumaric and syringic acids in fruit, p-coumaric, syringic, and procatechuic acids in leaf, and p-coumaric, syringic, caffeic, and procatechuic acids in root. Highest radical-scavenging activities of superoxide anion and hydroxyl were found in leaf and root, respectively (p<0.001).

Effect of Sasa quelpaertensis Nakai Extracts and its Constituent p-coumaric Acid on the Apoptosis of Human Cancer Cell Lines

  • Jang, Mi Gyeong;Ko, Hee Chul;Kim, Se Jae
    • Natural Product Sciences
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    • v.24 no.4
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    • pp.293-297
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    • 2018
  • Sasa quelpaertensis Nakai leaves contain a mixture of polysaccharides, amino acids, and polyphenols, which mediate various biological activities. For efficient utilization of its leaf, we reported the preparation procedure for phytochemical-rich extract (PRE) using the leaf residue, which was by-product of hot water extraction. This study was undertaken to evaluate the effects of PRE and its major constituent, p-coumaric acid,on the growth of several human cancer cell lines (MKN-74, MKN-45, SNU-1, SNU-16, and HL-60). The ethyl acetate fraction of PRE and p-coumaric acid significantly inhibited the proliferation of MKN-74 and HL-60 cells, respectively, and induced cell apoptosis, down-regulated Bcl-2 and poly (ADP-ribose) polymerase levels, and up-regulated those of Bax and caspase-3. These results show the potential utility of S. quelpaertensis Nakai leaves in cancer prevention.

Comparative study of antioxidant and anti-neuroinflammatory activity of leaf extracts of three different species of Bamboos in different extraction solvents containing caffeic acid, p-coumaric acid and tricin (왕대, 조릿대, 오죽의 추출 용매에 따른 항산화, 신경염증제어 활성 및 지표성분 caffeic acid, p-coumaric acid, tricin의 함량 비교)

  • Kim, Yon-Suk;Cho, Duk-Yeon;Kim, Mikyung;Choi, Dong-Kug
    • Korean Journal of Food Science and Technology
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    • v.53 no.3
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    • pp.296-303
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    • 2021
  • The antioxidant and anti-neuroinflammatory activities of water, 30, 70, and 100% ethanol extracts of leaves of three different species of bamboo (Phyllostachys nigra, P. bambusoides, and Sasa borealis) were investigated. The levels of total polyphenol and flavonoid were measured, and antioxidant activity was evaluated using various antioxidant assays (DPPH, ABTS, and FRAP). Lipopolysaccharide (LPS)-induced BV2 microglial cell activation was used to evaluate the anti-neuroinflammatory properties of the bamboo leaf extracts. Treatment with both aqueous and ethanolic extracts showed no cytotoxicity in BV-2 microglial cells. Pre-treatment of BV-2 cells with bamboo leaf extracts significantly inhibited LPS-induced excessive production of nitric oxide in a dose-dependent manner. Moreover, phytochemical analysis based on the extraction solvent showed that caffeic acid, p-coumaric acid, and tricin are the principal constituents of all three bamboo leaf extracts. Therefore, our findings suggest that bamboo leaf extract contains potent antioxidants and anti-neuroinflammatory compounds that can be used as potential therapeutic agents for the treat neuroinflammatory diseases.

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.