• Title/Summary/Keyword: p-Coumaric acid

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Biosynthesis of Two Flavones, Apigenin and Genkwanin, in Escherichia coli

  • Lee, Hyejin;Kim, Bong Gyu;Kim, Mihyang;Ahn, Joong-Hoon
    • Journal of Microbiology and Biotechnology
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    • v.25 no.9
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    • pp.1442-1448
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    • 2015
  • The flavonoid apigenin and its O-methyl derivative, genkwanin, have various biological activities and can be sourced from some vegetables and fruits. Microorganisms are an alternative for the synthesis of flavonoids. Here, to synthesize genkwanin from tyrosine, we first synthesized apigenin from p-coumaric acid using four genes (4CL, CHS, CHI, and FNS) in Escherichia coli. After optimization of different combinations of constructs, the yield of apigenin was increased from 13 mg/l to 30 mg/l. By introducing two additional genes (TAL and POMT7) into an apigenin-producing E. coli strain, we were able to synthesize 7-O-methyl apigenin (genkwanin) from tyrosine. In addition, the tyrosine content in E. coli was modulated by overexpressing aroG and tyrA. The engineered E. coli strain synthesized approximately 41 mg/l genkwanin.

Study on the Qualitative Discrimination of White, Red, and Black Ginseng Extract (백삼,홍삼과 흑삼 추출물의 정성적 구별법에 관한 연구)

  • Lee, Young-Sang;Im, Deok-Ho;Yang, Jin-Chul;Noh, Deok-Soo;Kim, Kwang-Il;Oh, Soo-Kyo;Choi, Kyo-Chan;Cha, Yun-Hwan
    • The Korean Journal of Food And Nutrition
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    • v.24 no.1
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    • pp.138-143
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    • 2011
  • This study analyzed the maltol quality, composition ratio of fatty acids, and contents of phenolic compounds in white ginseng extracts(four types), red ginseng extracts(five types), black ginseng extracts(two types), and Chinese ginseng extracts(nine types). By examining patterns in these measurements, we determined the characteristic factors of the extracts and measured the possibility of qualitative analysis. In the analysis of maltol using TLC, white ginseng extracts were not detected while red and black ginseng extracts were detected, so the possibility of detection was considered as a characteristic factor for qualitative analysis. Regarding the composition of fatty acids, palmitic and linoleic acids were the main fatty acids in the ginseng extracts palmitic acid was high in white ginseng extracts while linoleic was low in red ginseng extracts. Regarding the ratio(Pal/Lin) of the two fatty acids, there was a large difference between white ginseng extracts(56.7~64.3%) and red ginseng extracts(32.0~38.5%), and these figures seemed to be characteristic factors for the analysis. For the phenolic compounds, extracts contained maltol, caffeic acid, syringic acid, p-coumaric acid, ferulic acid, and cinnamic acid. White ginseng extracts contained similar percentages of phenolic compounds while red ginseng extracts had high maltol content. According to the measurement results of the percentages of maltol and cinnamic acid, white ginseng extracts showed values below five, whereas red and black ginseng extracts showed 53~289, which was also a characteristic factor for qualitative analysis. Consequently, we found that we can differentiate between ginseng extracts using characteristic factors that we analyzed in an experiment on white ginseng extracts from China.

The rate-determining step in the dark state recovery process in the photocycle of PYP

  • Sasaki, Jun;Kumauchi, Masato;Hamada, Norio;Tokunaga, Fumio
    • Journal of Photoscience
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    • v.9 no.2
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    • pp.130-133
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    • 2002
  • The last step in the photocycle of photoactive yellow protein (PYP) is a spontaneous recovery of the dark state from the active state in which the p-coumaric acid chromophore is thermally isomerized, concomitantly with the deprotona- tion of the chtomophore and the refolding of the protein moicty. For the purpose of understanding the mechanism of the thermal back-isomerization, we have investigated the rate-determining step by analyzing mutant PYPs of Met100, which was previously shown to play a major role in facilitating the reaction (1). The mutation to Lys, Leu, Ala, or Glu decelerated the dark state recovery by 1 to 3 three orders of magnitude. By evaluating temperature-dependence and pH-dependence of the kinetics of the dark state recovery, it was found that the retardation by mutations resulted from elevation of the activation enthalpy ( H$\^$┿/) and that the pKa of the chromophore, which was affected by the mutation, is in a linier correlation with the amplitude of the rate constants. It was, therefore, deduced from the correlation that the free energy for crossing the activated state in the dark recovery process is proportional to the free energy for the deprotonation of the chromophore, identifying the rate-determining step as the deprotonation of the chromophore. (1) Devanathan, S. Genick, U. K. Canestrelli, I. L. Meyer, T. E. Cusanovich, M. A. Getzoff, E. D. Tollin, G., Biochemistry 1998, 37, 11563 - 11568

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Phenolic Compounds Content and Tyrosinase Inhibitory Effect of Unripe Apple Extracts

  • Choi, Sang-Yoon;Kim, Sung-Soo;Lee, Yeon-Mi;Lee, Bog-Hieu;Han, Chan-Kyu
    • Journal of Applied Biological Chemistry
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    • v.53 no.2
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    • pp.87-90
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    • 2010
  • This study consisted of a quantitative analysis of five phenolic ingredients in differently sized unripe apple extracts, and their tyrosinase inhibitory effects were examined. In the HPLC analysis of phenolic ingredients, small ($4{\pm}1\;g$ per one) unripe apple extracts were observed to have significantly higher quercetin content than larger ($8{\pm}1\;g$ per one) unripe apple and ripe apple extracts. The amount of catechin, epicatechin, p-coumaric acid and chlorogenic acid contents were similar in both the small and large unripe apple extracts. For the results of the tyrosinase assay, small unripe apple extracts provided a potent tyrosinase inhibitory effect, showing 89.2% at 1000 ppm. The tyrosinase inhibitory effects of large unripe apple and ripe apple extracts were weaker than those of the small unripe apple extract. These results suggest that the small unripe apple extract could be useful for de-pigmenting material, while quercetin could be responsible for the potent tyrosinase inhibitory properties of small unripe apple extracts.

Inhibitory Activity against Helicobacter pylori of Isolated Compounds from Pinus koraiensis Siebold et Zucc Leaves

  • Jo, Bun-Sung;Cho, Young-Je
    • Journal of Applied Biological Chemistry
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    • v.59 no.1
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    • pp.19-23
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    • 2016
  • A phenol substance was extracted from Pinus koraiensis Siebold et Zucc leaf extracts and its biological efficacy was measured. The highest content of the phenol substance contained in Pinus koraiensis Siebold et Zucc leaves was 13.5 mg/g, which was obtained when it was extracted with 80% ethanol. At a concentration of 200 mg/mL, the phenolic substances extracted with 80% ethanol and water showed antimicrobial activities against Helicobacter pylori, producing clear zones of 10 and 12 mm diameter, respectively. Pinus koraiensis Siebold et Zucc. leaf extracts were separated using a Sephadex LH-20 column and 4 fractions were obtained (fractions A-D). Fractions C and D showed the greatest inhibitory activity against Helicobacter pylori producing 10.1 and 12.3 mm clear zones, respectively. These two fractions were purified using a Sephadex LH-20 and MCI-gel column ($H_2O{\rightarrow}100%$ ethanol). Purified compounds A and B were identified as syringic acid and compound C was identified as p-coumaric acid based on $^1H$-nuclear magnetic resonance (NMR), $^{13}C$-NMR, and fast atom bombardment mass spectrometry spectra. When two or more purified compounds were mixed, a synergistic effect of anti-Helicobacter pylori activity was evident. This result indicates that extracts of Pinus koraiensis Siebold et Zucc leaves could be considered a functional food because of their high antimicrobial properties.

Quality and antioxidant activity of ginseng seed processed by fermentation strains

  • Lee, Myung-Hee;Lee, Young-Chul;Kim, Sung-Soo;Hong, Hee-Do;Kim, Kyung-Tack
    • Journal of Ginseng Research
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    • v.39 no.2
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    • pp.178-182
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    • 2015
  • Background: Fermentation technology is widely used to alter the effective components of ginseng. This study was carried out to analyze the characteristics and antioxidant activity of ginseng seeds fermented by Bacillus, Lactobacillus, and Pediococcus strains. Methods: For ginseng seed fermentation, 1% of each strainwas inoculated on sterilized ginseng seeds and then incubated at $30^{\circ}C$ for 24 h in an incubator. Results: The total sugar content, acidic polysaccharides, and phenolic compounds, including p-coumaric acid, were higher in extracts of fermented ginseng seeds compared to a nonfermented control, and highest in extracts fermented with B. subtilis KFRI 1127. Fermentation led to higher antioxidant activity. The 2,2'-azine-bis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging activity was higher in ginseng seeds fermented by Bacillus subtilis than by Lactobacillus and Pediococcus, but Superoxide dismutase (SOD) enzyme activity was higher in ginseng seeds fermented by Lactobacillus and Pediococcus. Conclusion: Antioxidant activities measured by ABTS and SOD were higher in fermented ginseng seeds compared to nonfermented ginseng seeds. These results may contribute to improving the antioxidant activity and quality of ginseng subjected to fermentation treatments.

Profiling of the leaves and stems of Curcuma longa using LC-ESI-MS and HPLC analysis

  • Gia Han Tran;Hak-Dong Lee;Sun-Hyung Kim;Seok Lee;Sanghyun Lee
    • Journal of Applied Biological Chemistry
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    • v.66
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    • pp.338-344
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    • 2023
  • Curcuma longa is a plant belonging to the genus Curcuma and is distributed across various Asian regions. This plant is widely known for its rhizomes, which possess a variety of pharmacological properties. However, although the leaves and stems of this plant also contain several health-promoting secondary metabolites, very few studies have characterized these compounds. Therefore, our study sought to quantify the secondary metabolites from the leaves and stems of Curcuma longa L. (LSCL) using liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) and high-performance liquid chromatography (HPLC). Our LC-ESI-MS analyses detected twenty-one phenolic compounds in the LSCL, among which fifteen compounds were detected via HPLC analysis. Four compounds, namely vanillic acid (0.129 mg/g), p-coumaric acid (0.431 mg/g), 4-methylcatechol (0.199 mg/g), and afzelin (0.074 mg/g) were then quantified. These findings suggest that LSCL is rich in secondary metabolites and holds potential as a valuable resource for the development of functional and nutritional supplements in the future.

Anthocyanin Composition and Characteristics of 'Gaeryangmeoru', 'Kyoho', and 'Hongisul' Grape Varieties ('개량머루', '거봉' 및 '홍이슬' 품종의 anthocyanin 조성과 특징)

  • Kwon, YongHee;Park, Hee-Seung
    • Horticultural Science & Technology
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    • v.33 no.4
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    • pp.470-478
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    • 2015
  • This study was investigated the anthocyanin composition of 'Gaeryangmeoru', 'Kyoho', and 'Hongisul' grapes cultivated in Korea using ultra-performance liquid chromatography (UPLC) coupled to a mass spectrometer (MS) equipped with an ESI (electrospray ionization) source. 'Gaeryangmeoru' is a dark-blue grape used for winemaking that can reach its coloring in unfavorable weather. The 'Kyoho' and 'Hongisul' varieties are hybrid grapes that feature black and pink skin, respectively. The anthocyanins extracted from the peels of grapes were analyzed using UPLC-ESI-MS/MS. Twenty-five anthocyanins were identified in the 'Gaeryangmeoru' and 'Kyoho' varieties, and 21 were identified in the 'Hongisul' variety. Eight, 14 and five predominant anthocyanins were identified in 'Gaeryangmeoru', 'Kyoho' and 'Hongisul' grape respectively. In all three varieties, mono-glucosides were 2.3-5.9 times more abundant than di-glucoside. Malvidin was the predominant anthocyanidin in 'Gaeryangmeoru' (44.1%) and 'Kyoho' (56.5%), but cyanidin (96.8%) was in 'Hongisul'. The acylated anthocyanins in 'Gaeryangmeoru' (2.0%) were rare, whereas acylated anthocyanins with p-coumaric acid were predominant in 'Kyoho' (40.9%) and 'Hongisul' (70.7%). In particular, cyanidin feruloyl glucoside was found only in the 'Hongisul' cultivar and considered to be useful as a criterion for identification of the variety. As a result, the grape varieties were demonstrated to have variety-specific anthocyanin characteristics, enabling classification based on anthocyanin composition in terms of anthocyanidins, glucosylation and acylation. The taxonomical application of anthocyanin composition confirmed the possibility that 'Gaeryangmeoru' originated from Vitis amurensis or its hybrids, and the 'Hongisul' grape was distinguished from other grapes by cyanidin feruloyl glucoside.

Hypopigmenting Effects of Extracts from Bulbs of Lilium Oriental Hybrid 'Siberia' in Murine B16/F10 Melanoma Cells (백합뿌리 추출물의 멜라닌 생성 억제효과)

  • Yoon, Hoon Seok;Yang, Kyung-Wol;Kim, Jung Eun;Kim, Jeong Mi;Lee, Nam Ho;Hyun, Chang-Gu
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.43 no.5
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    • pp.705-711
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    • 2014
  • In order to develop a skin-whitening agent, melanin contents and intracellular tyrosinase activity were determined by western blotting. Ethyl acetate fractions of 80% ethanol extracts from lily (Lilium Oriental Hybrid 'Siberia') bulbs (R-EA) inhibited melanin synthesis in a dose-dependent manner in ${\alpha}$-melanocyte stimulating hormone (${\alpha}$-MSH)-treated B16/F10 murine melanoma cells. Intracellular tyrosinase activity and melanin contents were suppressed by 45% and 74%, respectively, in response to treatment with $100{\mu}g/mL$ of R-EA. Examination of protein expression associated with ${\alpha}$-MSH-induced melanogenesis showed that tyrosinase related protein (TRP)-1 was inhibited more strongly than tyrosinase, and these results were correlated with stronger inhibition of melanin synthesis than intracellular tyrosinase activity. Taken together, R-EA containing p-coumaric acid and resveratrol could be used as a hypopigmentation agent through suppression of sustained extracellular signal-regulated kinase (ERK) activation via melanogenic induction.

Phenolic Acid Composition and Antioxidative Activity of Red Ginseng Prepared by High Temperature and High Pressure Process (고온고압 처리 홍삼의 페놀산 조성과 항산화 활성)

  • Jung, Kyung Hee;Hong, Hee-Do;Cho, Chang-Won;Lee, Min-Young;Choi, Ung-Kyu;Kim, Young-Chan
    • The Korean Journal of Food And Nutrition
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    • v.25 no.4
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    • pp.827-832
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    • 2012
  • This study was conducted to develop HTHP ginseng (high temperature and high pressure ginseng) with improved antioxidative activity and phenolic acid composition by high temperature and high pressure process. The HTHP ginseng extract was analyzed for the total phenol content, DPPH radical scavenging activity and phenolic acid composition. The total phenol content was increased in HTHP ginseng (14.76 mg/g) compared to raw ginseng (3.59 mg/g) and red ginseng (3.93 mg/g). DPPH radical scavenging activities of HTHP ginseng, raw ginseng and red ginseng extracts were 4.8~78.4%, 1~47.4% and 1.8~56.5% at $1{\sim}100mg/m{\ell}$ concentration. Also ABTS radical scavenging activities of HTHP ginseng, raw ginseng and red ginseng extracts were 8.9~99.8%, 3.4~96% and 1.2~96.5% at $1{\sim}100mg/m{\ell}$ concentration. In HPLC analysis, amounts of measured phenolic acid of HTHP ginseng greatly increased than raw ginseng and red ginseng, but salicylic acid was not detected in HTHP ginseng. In addition, DPPH radical scavenging activity of phenolic acid from HTHP ginseng was increased. Consequently, we believe high temperature and high pressure process is better method than existing method to increase the bioactivity of ginseng.