• Title/Summary/Keyword: 4-coumaric acid

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Common Ragweed-Derived Phenolic Compounds and Their Effects on Germination and Seedling Growth of Weed Species (돼지풀의 페놀화합물 동정 및 이들 화합물이 잡초의 유식물 생장에 미치는 영향)

  • Choi, Bong-Su;Song, Duk-Young;Sung, Jwa-Kyung;Kim, Chung-Guk;Song, Beom-Heon;Woo, Sun-Hee;Lee, Chul-Won
    • Korean Journal of Weed Science
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    • v.30 no.4
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    • pp.396-404
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    • 2010
  • Phenolic compounds, which are products of secondary metabolism, have been demonstrated to be widespread growth substances in plants. The objectives of this study were to identify the phenolic compounds in common ragweed (Ambrosia artemisiifolia var. elatior) by HPLC and to evaluate their effects on germination and seedling growth of three weed species. Under controlled conditions in Petri dishes at $25^{\circ}C$, $10^{-3}$ and $10^{-4}$ M solutions of phenolic compounds were evaluated in seed germination tests. Four phenolic compounds (caffeic acid, O-coumaric acid, ${\rho}$-coumaric acid and ferulic acid) in common ragweed plant were identified and their concentration was increased from the stage before flowering through full flowering stage. Treatment of O- and ${\rho}$-coumaric acids delayed the seed germination of Digitalia ciliaris, while the treatment of caffeic acid delayed the seed germination of Echinochloa crus-galli. In time to 50% germination ($T_{50}$), phenolic compounds at $10^{-4}$ M promoted in Cyperus microiria and E. crus-galli but the level of $10^{-3}$ M delayed the $T_{50}$ of those weeds. The O-coumaric acid inhibited seed germination and seedling growth of the tested weeds and especially it perfectly inhibited the root growth of E. crus-galli.

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.

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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Synthesis and Evaluation of Coumaroyl Dipeptide Amide as Potential Whitening Agents

  • Lee, Hye-Suk;Shin, Kyong-Hoon;Ryu, Geun-Seog;Cho, In-Shik;Kim, Jae-Il;Lee, Jae-Ho;Kim, Han-Young
    • Bulletin of the Korean Chemical Society
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    • v.34 no.10
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    • pp.3017-3021
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    • 2013
  • Coumaroyl dipeptide amide, Coumaric acid-LG-$NH_2$, was prepared successfully using the solid-phase method, and its efficacy as a skin whitening agent was studied. Coumaric acid-LG-$NH_2$ was prepared with Rink-amide resin, and 96.354% of purity was obtained. Using MTT assay and LDH release assay, we found that it exhibited very low cytotoxicity. And, we found that Coumaric acid-LG-$NH_2$ inhibited tyrosinase activity dose-dependently and showed superior tyrosinase inhibitory activity to well-known whitening agent, arbutin. $IC_{50}$ value of Coumaric acid-LG-$NH_2$ was 182.4 ${\mu}M$, and $IC_{50}$ value of arbutin was 384.6 ${\mu}M$. Also, in measurement of melanin contents using B16F1 melanoma cell lines, Coumaric acid-LG-$NH_2$ reduced melanin production induced by ${\alpha}$-MSH statistically significant, and showed superior melanin inhibitory activity to p-coumaric acid or arbutin. In addition, Coumaric acid-LG-$NH_2$ reduced MC1R mRNA expression level. Thus, we concluded that MC1R pathway is the significant pathway of Coumaric acid-LG-$NH_2$, and Coumaric acid-LG-$NH_2$ has great potential to be used as novel whitening agents.

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.

Optimization of Ethanol Extraction Conditions for Artemisis capillaris Effective Components Using Response Surface Methodology (반응표면분석법을 이용한 인진쑥 유효성분의 에탄올 추출조건 최적화)

  • Kim, Seong-Ho
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.43 no.5
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    • pp.741-748
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    • 2014
  • This study was conducted to monitor the quality characteristics of Artemisis capillaris ethanolic extract by response surface methodology. The independent variables were extraction temperature ($X_1$; 60, 70, 80, 90, and $100^{\circ}C$), extraction time ($X_2$; 1, 2, 3, 4, and 5 hr), and ethanol concentration ($X_3$; 0, 20, 40, 60, and 80%). Soluble solid content ($Y_1$), chlorogenic acid content ($Y_2$), and coumaric acid content ($Y_3$), etc. were analyzed as the dependent variables. Estimated optimal conditions for soluble solids were an extraction temperature of $87.65^{\circ}C$, extraction time of 3.19 hr, and ethanol concentration of 42.40%. The optimal extraction conditions for chlorogenic acid were $84.30^{\circ}C$, 3.14 hr, and 47.85%, respectively. Further, those for coumaric acid were $83.45^{\circ}C$, 3.40 hr, and 45.39%, respectively. Extraction conditions for effective components of Artemisis capillaris were superimposed by response surface plots on optimization extraction condition of each dependent variable, including soluble solid, chlorogenic acid, and coumaric acid contents. As a result, superimposed extraction conditions were $80{\sim}90^{\circ}C$, 3~4 hr, and 40~50%, respectively. Under these conditions, soluble solid, chlorogenic acid, and coumaric acid contents were 1.09%, 25.66 mg%, and 20.25 mg%, respectively.

Phytochemical Study on the Vitis thunbergii var. sinuata

  • Jon
    • Korean Journal of Plant Resources
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    • v.9 no.1
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    • pp.55-62
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    • 1996
  • The caffeic acid, 4-O-$\beta$-D-glucopyranosyl caffeic acid, 4-O-$\beta$-D-glucopyranosyl-$\rho$-coumaric acid and 7-O-$\beta$-D-glucuronide of ($\pm$)-eriodictyol have been isolated from the root of Vitis thunbergii var. sinuata. The structures of compounds were determined by chemical and spectroscopic methods.

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Antioxidative Activity of Phenolic Acids Isolated from Jindalrae Flower (Rhododendron mucronulatum Turzaninow) (진달래꽃으로부터 분리된 페놀산 화합물의 항산화성에 관한 연구)

  • Kim, Mi-Ae;Jones, A. Daniel;Chung, Tae-Yung
    • Applied Biological Chemistry
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    • v.39 no.6
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    • pp.506-511
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    • 1996
  • Six phenolic acids were isolated from Jindalrae flowers (Rhododendron mucronulatum Turcz.), an edible plant in Korea. These compounds were identified as chlorogenic acid, 3,5-O-dicaffeoylquinic acid, 4,5-O-dicaffeoylquinic acid, caffeic acid, ferulic acid, and p-coumaric acid on the basis of IR, UV, $^{1}H$ and $^{13}C$ NMR, FAB-MS, ES-MS and/or El-MS data. Chlorogenic acid (0.2 g) present in both ethyl acetate and ethyl ether fractions comprised up to 38.5% of the total phenolic acid amount (0.52 g) finally recovered by means of polyamide C-200 column chromatography, preparative TLC, recrystallization, and Sephadex LH-20 column chromatography The antioxidant activities were measured in an ethanol solution of linoleic acid in the presence of ferric thiocyanate. The antioxidant efficiency increased in the order of p-coumaric acid<${\alpha}-tocopherol$

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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).