• Title/Summary/Keyword: Hydroxycinnamic Acids

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Research Trend about the Development of White Biotech-Based Aromatic Compounds (화이트바이오텍기반 방향족화합물 개발에 관한 연구동향)

  • Lee, Jin-Ho
    • Microbiology and Biotechnology Letters
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    • v.37 no.4
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    • pp.306-315
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    • 2009
  • Due to the depleting petroleum reserve, recurring energy crisis, and global warming, it is necessary to study the development of white biotech-based aromatic chemical feedstock from renewable biomass for replacing petroleum-based one. In particular, the production of aromatic intermediates and derivatives in biosynthetic pathway of aromatic amino acids from glucose might be replaced by the production of petrochemical-based aromatic chemical feedstock including benzene-derived aromatic compounds. In this review, I briefly described the production technology for hydroquinone, catechol, adipic acid, shikimic acid, gallic acid, pyrogallol, vanillin, p-hydroxycinnamic acid, p-hydroxystyrene, p-hydroxybenzoic acid, indigo, and indole 3-acetic acid using metabolic engineering, bioconversion, and chemical process. The problems and possible solutions regarding development of production technology for competitive white biotech-based aromatic compounds were also discussed.

Quantitative Changes of Hydroxycinnamic Acid Derivatives and Anthocyanin in Corn (Zea mays L.) According to Cultivars and Heat Processes (옥수수의 품종별 및 가공별 Hydroxycinnamic Acid 유도체 및 Anthocyanin 색소의 함량 변화)

  • Yu, Myeong-Hwa;Kim, Eun-Ok;Choi, Sang-Won
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.39 no.6
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    • pp.843-852
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    • 2010
  • Hydroxycinnamic acid derivatives (HADs) and anthocyanins in corn (Zea mays L.) have recently been reported to have anticarcinogenic, anti-hypertensive, antidiabetic, antifungal, antioxidant, and anti-melanogenic activities. Five HADs and anthocyanins in corn were quantified by HPLC according to cultivars and heat processes. In addition, major anthocyanin of a black waxy corn was isolated and identified by several instrumental analysis, and its content was also quantified by HPLC according to heat processes. Of the ten corn cultivars, five waxy corn cultivars had moderate five HADs contents except "Baksa" waxy corn with higher two free cinnamic acids (FCAs), p-coumaric and ferulic acids. In contrast, three dent corn cultivars contained higher levels of three polyamine conjugates (PCs), CFP, DCP and DFP, and especially "P3394" had the highest amount of the three PCs. Two sweet corn cultivars had generally intermediate HADs levels between waxy and dent corn cultivars. Of the three colored-waxy corns, a black Mibaek waxy corn had the highest anthocyanin content. During heat processes, levels of two FCAs in the black waxy corn generally increased, whereas no significant change on three PCs contents was observed except the puffing process. Roasting, retort and puffing processes significantly increased two FCAs and especially, the puffed black waxy corn had the highest amount of FCAs. Meanwhile, most heat treatments except retort process, considerably decreased total anthocyanin contents, and especially the puffed black waxy corn had nearly no anthocyanin. Level of one major anthocyanin, pelargonidin 3-glucoside (P3G) isolated from a black waxy corn was appreciably decreased by heat treatments except retort process, which greatly increased P3G content. These results suggest that the retorted black waxy corn may be a promising high quality functional corn product.

Effect of Thermal Pretreatment on the Functional Constituents of Waxy Corn (Zea mays L.)

  • Kim, Eun-Ok;Yu, Myong-Hwa;Lee, Ki-Teak;Yun, Kyoung-Seob;Choi, Sang-Won
    • Food Science and Biotechnology
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    • v.18 no.6
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    • pp.1336-1341
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    • 2009
  • Quantitative changes in functional constituents of waxy corn (Zea mays L.) by 5 different thermal pretreatments, including roasting, steaming, microwave, puffing, and extruding, were determined and compared with those of the raw waxy corn. There were no significant differences in fatty acid compositions among the corn treated with 5 thermal treatments. Levels of $\alpha$- and $\gamma$-tocopherols, soluble amino acids, and phytosterols decreased by thermal treatments, while those of p-coumaric and ferulic acids considerably increased by thermal treatments. In particular, the contents of tocopherols and phytosterols, and souble amino acid decreased significant in the steaming and puffing processes, respectively, whereas those of 2 free cinnamic acids increased significantly in the steaming and puffing processes. The extruding process showed smaller quantitative changes in tocopherols, phytosterols, and hydroxycinnamic acid derivatives compared to other heat pretreatments. These results suggest that the extruding process have a positive effect on valuable phytochemicals in waxy corn.

The Nitrite Scavenging and Electron Donating Ability of Phenolic Compounds (페놀성 화합물의 아질산염 소거 및 전자공여 작용)

  • Kang, Yoon-Han;Park, Yong-Kon;Lee, Gee-Dong
    • Korean Journal of Food Science and Technology
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    • v.28 no.2
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    • pp.232-239
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    • 1996
  • Phenolic compounds are known to inhibit the nitrosation or oxidation reaction. In the present work, the effects of phenolic compounds including phenolic acids and flavonoids on the nitrite-scavenging and electron donating ability were tested as scavenger of nitrite which is believed to participate in the formation of N-nitroso compounds and investigated as electron donator. The nitrite scavenging ability appeared in all the phenolic acids and showed the highest value at PH 1.2. Among the Phenolic compounds, phenolic acids showed higher nitrite-scavenging action than some flavonoids. Futhermore, the nitrite scavenging action of phenolic compounds was pH dependent highest at pH 1.2 and lowest at pH 6.0. The electron donating ability (EDA) by reduction of ${\alpha},{\alpha}$-diphenyl-${\beta}$-picrylhydrazyl (DPPH) among hydroxybenzoic acids was in the decreasing order of gallic acid, gentisic acid, syringic acid, protocatechuic acid, salicylic acid, vanillic acid, benzoic acid and p-hydroxybenzoic acid. EDA of hydroxycinnamic acids was in the decreasing order of hydrocaffeic acid, caffeic acid, ferulic acid, p-coumaric acid and trans-cinnamic acid. EDA of flavonoids was in the decreasing order of (+)catechin, rutin, quercetin, naringin and hesperidin. Other phenolic compounds were significantly high in electron donating abilities.

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Structural Characteristics of Cell Walls of Forage Grasses - Their Nutritional Evaluation for Ruminants - - Review -

  • Iiyama, Kenji;Tuyet Lam, Thi Bach
    • Asian-Australasian Journal of Animal Sciences
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    • v.14 no.6
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    • pp.862-879
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    • 2001
  • The walls of all higher plants are organized as a cellulosic, fibrillar phase embedded in a matrix phase composed of non-cellulosic polysaccharides, some proteins and, in most secondary walls, lignin. At the effective utilization of plant biomass, qualitative and quantitative analyses of plant cell walls are essential. Structural features of individual components are being clarified using newly developed equipments and techniques. However, "empirical" procedures to elucidate plant cell walls, which are not due to scientific definition of components, are still applied in some fields. These procedures may give misunderstanding for the effective utilization of plant biomass. In addition, interesting the investigation of wall organization is moving towards not only qualitatively characterisation, but also quantitation of the associations between wall components. These involve polysaccharide-polysaccharide and polysaccharide-lignin cross-links. Investigation of the associations is being done in order to understand the chemical structure, organization and biosynthesis of the cell wall and physiology of the plants. Procedures for qualitative and quantitative analyses based on the definition of cell wall components are reviewed focussing in nutritional elucidation of forage grasses by ruminant microorganisms.

Evolution of 49 Phenolic Compounds in Shortly-aged Red Wines Made from Cabernet Gernischt (Vitis vinifera L. cv.)

  • Li, Zheng;Pan, Qiu-Hong;Jin, Zan-Min;He, Jian-Jun;Liang, Na-Na;Duan, Chang-Qing
    • Food Science and Biotechnology
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    • v.18 no.4
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    • pp.1001-1012
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    • 2009
  • A total of 49 phenolic compounds were identified from the aged red wines made from Cabernet Gernischt (Vitis vinifera L. cv.) grapes, a Chinese characteristic variety, including 13 anthocyanins, 4 pryanocyanins, 4 flavan-3-ol monomers, 6 flavan-3-ol polymers, 7 flavonols, 6 hydroxybenzoic acids, 5 hydroxycinnamic acids, 3 stilbenes, and 1 polymeric pigment. Evolution of these compounds was investigated in wines aged 1 to 13 months. Variance analysis showed that the levels of most phenolics existed significant difference in between wines aged 3 and 9 months. Cluster analysis indicated that 2 groups could be distinguished, one corresponding to wines aged 1 to 3 months and the other to wines aged 4 to 13 months. It was thus suggested that there were 2 key-stages for the development of fine wine quality, at the aged 3 and 9 months, respectively. This work would provide some helpful information for quality control in wine production.

Properties and Antioxidative Activities of Phenolic Acid Concentrates of Rice Bran (미강 페놀산 농축물의 특성 및 항산화 활성)

  • Jung, Eun-Hee;Hwang, In-Kyeong;Ha, Tae-Youl
    • Korean Journal of Food Science and Technology
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    • v.42 no.5
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    • pp.593-597
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    • 2010
  • This study investigated the properties and antioxidative activities of phenolic acid concentrates of rice bran. Rice bran contains bioactive substances such as phenolic compounds, which can provide health benefits as natural antioxidants. This study examined how levels of phenolic acids can be obtained efficiently through various extraction methods. The extractions of defatted rice bran were followed by using ethylacetate (RBE-I), ethylacetate after alkaline hydrolysis (RBE-II), and 80% methanol (RBE-III). For all extracts, yields (%), total polyphenol contents (TPC), various phenolic acids and antioxidative activities were estimated. RBE-II had the highest total polyphenol contents (526.72 mg/100 g rice bran) and showed high antioxidative activity (74.7%). To concentrate the phenolic acids, RBE-II was passed through Sep-pak $C_{18}$ Vac cartridge and F1-RBE-II was collected by the elution of 50% methanol. The total phenolic content of F1-RBE-II (736.8 mg/100 g rice bran) was higher than that of RBE-II (367.1 mg/100 g rice bran), and the ratios of ferulic acid (73%) and sinapic acid (14%) increased. As RBE-II was analysed by HPLC, 6 different phenolic acids were found via chromatography, whereas F1-RBE-II showed 5 different peaks and the major phenolic acid was identified as ferulic acid. The ABTS radical scavenging activity of F1-RBE-II was the highest among the rice bran extracts. In a ${\beta}$-carotene-linoleic acid model system, linoleic acid oxidation was reduced by F1-RBE-II (73%) and RBE-II (35%).

Comparison of Phenolic Acid from Shoots of Aralia elata and Kalopanax pictus Cultivated in Korea Using UPLC-DAD-ESI(+)-QToF/MS (UPLC-DAD-ESI(+)-QToF/MS를 이용한 국내산 두릅나무 및 음나무 순 내 페놀산 특성 비교)

  • Kim, Young Jin;Kim, Heon-Woong;Lee, Min-Ki;Lee, Seon-Hye;Asamenew, Gelila;Lee, Suji;Lee, Sang Hoon;Cha, Youn-Soo;Kim, Jung Bong
    • Korean Journal of Environmental Agriculture
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    • v.37 no.4
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    • pp.260-267
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    • 2018
  • BACKGROUND: In this study, shoots of Aralia elata and Kalopanax pictus which belong to the Araliaceae family were analyzed using UPLC-DAD-ESI(+)-QToF/MS to characterize of individual phenolic acids. METHODS AND RESULTS: Total thirteen phenolic acids were identified, and nine hydroxycinnamic acid derivatives have been identified for the first time in shoots of Aralia elata and Kalopanax pictus. For total phenolic acid content (mg/100g dry weight), shoots of Aralia elata and Kalopanax pictus showed 754.8 and 845.3 mg/100g, respectively. 5-O-Caffeoylquinic acid (49%) and 3,5-di-O-caffeoylquinic acid (44%) were found as major phenolic acids in Aralia elata, while 5-O-caffeoylquinic acid (91%) was a major component in Kalopanax pictus. CONCLUSION: On comparing the two plants, it was considered that the biosynthesis of 3,5-di-O-caffeoylquinic acid can be affected by 5-O-caffeoylquinic acid in Aralia elata.

Phosphorylation of Akt Mediates Anti-Inflammatory Activity of 1-p-Coumaroyl ${\beta}$-D-Glucoside Against Lipopolysaccharide-Induced Inflammation in RAW264.7 Cells

  • Vo, Van Anh;Lee, Jae-Won;Kim, Ji-Young;Park, Jun-Ho;Lee, Hee Jae;Kim, Sung-Soo;Kwon, Yong-Soo;Chun, Wanjoo
    • The Korean Journal of Physiology and Pharmacology
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    • v.18 no.1
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    • pp.79-86
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    • 2014
  • Hydroxycinnamic acids have been reported to possess numerous pharmacological activities such as antioxidant, anti-inflammatory, and anti-tumor properties. However, the biological activity of 1-p-coumaroyl ${\beta}$-D-glucoside (CG), a glucose ester derivative of p-coumaric acid, has not been clearly examined. The objective of this study is to elucidate the anti-inflammatory action of CG in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. In the present study, CG significantly suppressed LPS-induced excessive production of pro-inflammatory mediators such as nitric oxide (NO) and $PGE_2$ and the protein expression of iNOS and COX-2. CG also inhibited LPS-induced secretion of pro-inflammatory cytokines, IL-$1{\beta}$ and TNF-${\alpha}$. In addition, CG significantly suppressed LPS-induced degradation of $I{\kappa}B$. To elucidate the underlying mechanism by which CG exerts its anti-inflammatory action, involvement of various signaling pathways were examined. CG exhibited significantly increased Akt phosphorylation in a concentration-dependent manner, although MAPKs such as Erk, JNK, and p38 appeared not to be involved. Furthermore, inhibition of Akt/PI3K signaling pathway with wortmannin significantly, albeit not completely, abolished CG-induced Akt phosphorylation and anti-inflammatory actions. Taken together, the present study demonstrates that Akt signaling pathway might play a major role in CG-mediated anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells.

3,4,5-Trihydroxycinnamic Acid Inhibits LPS-Induced iNOS Expression by Suppressing NF-${\kappa}B$ Activation in BV2 Microglial Cells

  • Lee, Jae-Won;Bae, Chang-Jun;Choi, Yong-Jun;Kim, Song-In;Kim, Nam-Ho;Lee, Hee-Jae;Kim, Sung-Soo;Kwon, Yong-Soo;Chun, Wan-Joo
    • The Korean Journal of Physiology and Pharmacology
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    • v.16 no.2
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    • pp.107-112
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    • 2012
  • Although various derivatives of caffeic acid have been reported to possess a wide variety of biological activities such as neuronal protection against excitotoxicity and anti-inflammatory property, the biological activity of 3,4,5-trihydroxycinnamic acid (THC), a derivative of hydroxycinnamic acids, has not been clearly examined. The objective of the present study is to evaluate the anti-inflammatory effects of THC on lipopolysaccharide (LPS)-stimulated BV2 microglial cells. THC significantly suppressed LPS-induced excessive production of nitric oxide (NO) and expression of iNOS, which is responsible for the production of iNOS. THC also suppressed LPS-induced overproduction of pro-inflammatory cytokines such as IL-$1{\beta}$and TNF-${\alpha}$ in BV2 microgilal cells. Furthermore, THC significantly suppressed LPS-induced degradation of $I{\kappa}B$, which retains NF-${\kappa}B$ in the cytoplasm. Therefore, THC attenuated nuclear translocation of NF-${\kappa}B$, a major pro-inflammatory transcription factor. Taken together, the present study for the first time demonstrates that THC exhibits antiinflammatory activity through the suppression of NF-${\kappa}B$ transcriptional activation in LPS-stimulated BV2 microglial cells.