• Title/Summary/Keyword: trans-Cinnamic acid

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Composition of Phenolic Compounds in Hypochaeris radica L. Extracts and their Allelopathic Effects on Gramineous Forage Crops (서양금혼초(Hypochaeris radicata L.) 추출물의 화본과 사료작물에 대한 타감작용 효과 및 phenole 화합물의 조성)

  • Kim, Og-Yim;Park, Sun-Ill;Jung, Ill-Min;Ha, Sang-Young
    • Korean Journal of Environmental Agriculture
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    • v.24 no.4
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    • pp.391-397
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    • 2005
  • This study was carried out to examine the allelopathic effect of the aqueous extract of Hypochaeris radicata L. on growth of three gramineous forage crops, tall fescue, perennial ryegrass and italian ryegrass. The result on relative elongation ration (RER) of gramineous forage crops treated with the aqueous extract of Hypochaeris radicata L. and the change of quantity generally indicated the inhibitory effect. The inhibitory effect was increased as its concentration was increased. As a result, it is ascertained that the aqueous extract of Hypochaeris radicata L. has allelopathy effect. According to the chemical experiment of the allelochemical substances in Hypochaeris radicata L. by HPLC, there are the differences at each part of plants. However, it is ascertained that there are eleven phenolic compounds, ${\rho}-hydroxybenzoic$ acid, chlorogenic acid, catechin, caffeic acid, syringic acid, salicylic acid, ${\rho}-coumaric$ acid, ferulic acid, hesperidin, trans-cinnamic acid and naringenin. Especially three phenolic acids such as caffeic acid, ferulic acid and naringenin were detected from all part of the plant.

Cometabolism of $\omega$-Phenylalkanoic Acids with Butyric Acid for Efficient Production of Aromatic Polyesters in Pseudomonas putida BM01

  • Song, Jae-Jun;Choi, Mun-Hwan;Yoon, Sung-Chul;Huh, Nam-Eung
    • Journal of Microbiology and Biotechnology
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    • v.11 no.3
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    • pp.435-442
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    • 2001
  • Poly(3-hydroxy-5-phenylvalerate) [P(3HPV)] was efficiently accumulated from 5-phenylvalerate (5PV) in Pseudomonas putida BM01 in a mineral salts medium containing butyric acid (BA) as the cosubstrate. A nove aromatic copolyester, poly(5 mol% 3-hydroxy-4-phenylbutyrate-co- 95 mol% 3-hydroxy-6-phenylhexanoate) [P(3HPB-co-3HPC)] was also synthesized from 6-phenylhexanoate (6PC) plus Ba. The two aromatic polymers, P(3HPV) and P(3HPB-co-3HPC), were found to be amorphous and showed different glass-transition temperatures at $15^{\circ}C$ and $10^{\circ}C$, respectively. When the bacterium was grown ina medium containing 20 mM 5PV as the sole carbon source for 140 h, 0.4 g/l of dry cells was obtained in a flask cultivation and 20 wt% of P(3HPV) homopolymer was accumulated in the cells. However, when it was grown with a mixture of 2 mM 5PV and 50 mM BA for 40 h, the yield of dry biomass was increased up to 2.5 g/l and the content of P(3HPV) in the dry cells was optimally 56 wt%. This efficient production of P(3HPV) homopolymer from the mixed substrate was feasible because BA only supported cell growth and did not induce any aliphatic PHA accumulation. The metabolites released into the PHA synthesis medium were analyzed using GC or GC/MS. Two $\beta$-oxidation derivatives, 3-phenylpropionic acid and trans-cinnamic acid, were found in the 5V-grown cell medium and these comprised 55-88 mol% of the 5PV consumed. In the 6PC-grown medium containing Ba, seven ${\beta}$-oxidation and related intermediates were found, which included phenylacetic acid, 4-phenylbutyric acid, cis-4-phenyl-2-butenoic acid, trans-4-phenyl-3-butenoic acid, trans-4-phenyl-2-butenoic acid, 3-hydroxy-4-phenylbutyric acid, and 3-hydroxy-6-phenylhexanoic acid. Accordingly, based on the metabolite analysis, PHA synthesis pathways from the two aromatic carbon sources are suggested.

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Structural Features of Polyphenolic Compounds in Their NO Inhibitory Activities

  • Kim, Byung-Hun;Lee, Yong-Gyu;Kim, Tae-Woong;Cho, Jae-Youl
    • Biomolecules & Therapeutics
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    • v.17 no.1
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    • pp.79-85
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    • 2009
  • Polyphenolic compounds are reported to have various pharmacological activities such as anti-oxidative, anti-cancerous, anti-inflammatory and anti-aging effects. Although numerous papers explore their functional roles in many different cellular actions, not many studies handle their structural features in anti-inflammatory responses. In this study, therefore, we examined structural role of substituted transstilbenes in their NO inhibitory and NF-${\kappa}B$ suppressive activities. Of 10 compounds tested, 4 compounds (cinnamic acid, resveratrol, piceatannol and curcumin) displayed NO inhibitory activities in a dose-dependent manner. Similarly, these compounds blocked LPS-induced cytotoxicity of RAW264.7 cells. All NO inhibitory compounds also inhibited $I{\kappa}B{\alpha}$ phosphorylation, a hallmark for NF-${\kappa}B$ activation. However, these inhibitory compounds exhibited distinct suppressive pattern in tumor necrosis factor (TNF)-${\alpha}$- or phorbol-12-myristate-13-acetate (PMA)-induced NF-${\kappa}B$ and AP-1 activation. According to structure-activity relationship study, polarity and size of ring B seem to be important for diminishing NO production. Therefore, our data suggest that substituted trans-stilbenes can be developed as novel anti-inflammatory drug or further developed as lead compounds for another improvement.

Cloning and mRNA Expression Analysis of the Gene Encoding Phenylalanine Ammonia-Lyase of the Ectomycorrhizal Fungus Tricholoma matsutake

  • Yoon, Hyeokjun;You, Young-Hyun;Kim, Ye-Eun;Kim, Young Ja;Kong, Won-Sik;Kim, Jong-Guk
    • Journal of Microbiology and Biotechnology
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    • v.23 no.8
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    • pp.1055-1059
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    • 2013
  • The ectomycorrhizal fungus Tricholoma matsutake grows symbiotically with Pinus densiflora. Phenylalanine ammonia-lyase (E.C. 4.3.1.24) catalyzes the conversion of L-phenylalanine to trans-cinnamic acid. The role of fungal phenylalanine ammonia-lyase, however, has not been clear until now. In this study, the gene encoding phenylalanine ammonia-lyase (PAL), which was isolated from T. matsutake, was cloned and characterized. The PAL gene (tmpal) consists of 2,160 nucleotides, coding for a polypeptide containing 719 amino acid residues. The deduced amino acid sequence of tmpal from T. matsutake shows high identity (70%) with that from Laccaria bicolor. Comparative analysis of the PAL genes among T. matsutake and other species of the class Agaricomycetes showed that both active sites and binding sites were significantly conserved among these genes. The transcriptional analysis of the PAL gene revealed a differential gene expression pattern depending on the developmental stages (mycelium, primordium, stipe, pileus, and gills) of T. matsutake. These results suggest that the PAL gene in T. matsutake plays an important role in multiple physiological functions.

Anticoagulant Properties of the Active Compound Derived from Cinnamomum cassia Bark

  • Lee, Hoi-Seon
    • Food Science and Biotechnology
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    • v.16 no.2
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    • pp.218-222
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    • 2007
  • The anticoagulant properties of Cinnamomum cassia bark-derived materials were evaluated against platelet aggregation induced by arachidonic acid (AA), collagen, platelet activating factor (PAF), or thrombin, and these effects were then compared to those of three commercially available compounds (cinnamic acid, cinnamyl alcohol, and aspirin). The active constituent obtained from C. cassia barks was isolated by silica gel column chromatography and high pressure liquid chromatography (HPLC), and was characterized as trans-cinnamaldehyde by MS, $^1H-NMR$, $^{13}C-NMR$, and IR spectroscopy. With regard to 50% inhibitory concentration ($IC_{50}$) values, cinnamaldehyde was found to effectively inhibit platelet aggregation induced by AA ($IC_{50},\;43.2\;{\mu}M$) and collagen ($IC_{50},\;3.1\;{\mu}M$). By way of comparison, cinnamaldehyde proved to be a significantly more potent platelet inhibitor against platelet aggregation induced by collagen than aspirin. The effect exerted by cinnamaldehyde against platelet aggregation induced by AA was 1.2 times less than that of aspirin. These results indicate that cinnamaldehyde may prove useful as a lead compound for the inhibition of platelet aggregation induced by AA and collagen.

Phytotoxic Effect of Xanthium occidentale Leaf Extract on Seed Germination and Early Seedling Growth of Alfalfa and Barnyard Grass

  • Chon, Sang-Uk
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.49 no.1
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    • pp.30-35
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    • 2004
  • Compositae plants are known to contain biologically active substances that are allelopathic to agricultural crops as well as weed species. Aqueous extracts from leaves of Xanthium occidentale were assayed against alfalfa (Medicago sativa) to determine their allelopathic effects, and the result showed that the extracts applied onto filter paper significantly inhibited seed germination as well as root growth of alfalfa. Untreated seeds germinated in 60h, but extract concentrations greater than 30g $\textrm{L}^{-1}$ delayed seed germination. The extracts significantly inhibited seed germination of alfalfa, and $\beta$-amylase activity of alfalfa and barley seeds during 24-36 hours after treatment. Aqueous extracts of 40 g $\textrm{L}^{-1}$ from X. occidentale were completely inhibited the hypocotyl and root growth of alfalfa. Aqueous leaf extracts showed the highest inhibitory effect and followed by root and stem extracts. Early seedling growth of both alfalfa and barnyard grass (Echinochloa crus-galli) was significantly reduced by methanol extracts. By means of high-performance liquid chromatography, chlorogenic acid and trans-cinnamic acid were quantified as the highest amounts from water and EtOAc fractions, respectively. BuOH and EtOAc fractions of X. occidentale reduced alfalfa root growth more than did hexane and water fractions. The findings of the bioassays for aqueous or methanol extracts reflected that the inhibitory effect of extract was closely related to the level of responsible allelochemicals found in plant extracts.

Production and Characterization of Phenylalanine Ammonia-lyase from Rhodotorula aurantiaca K-505

  • Cho, Dae-Haeng;Chae, Hee-Jeong;Kim, Eui-Yong
    • Preventive Nutrition and Food Science
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    • v.2 no.4
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    • pp.354-359
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    • 1997
  • Optimal cultivation conditions for the production of phenylalanine ammonia-lyase(PAL) from Rhodotorula aurantiaca K-505 were selected, and the kinetic parameters of the produced PAL were determined. The most suitable carbon and nitrogen sources were glucose and tryptone, respectively. The strain expressed PAL constituttively when using the optimized semi-complex media. High cell density culture could be critical for maximal production of PAl since the PAL ynthesis was growth associated. maximum PAL activity was observed at initial pH 6.0. although the ll growth was not markedly affected by temperature between 22 and 28$^{\circ}C$, the cells yielded the maximum PAL activity when cultivated at 22$^{\circ}C$. The maximum activity for deamination of L-phenylalnine to trans-cinnamic acid was observed around pH 8.8. The PAL activity gave the maximum at 45$^{\circ}C$, and greatly decreased at higher than 5$0^{\circ}C$. Activation energy({TEX}$E_{a}${/TEX}) calculated from Arrhenius equation was 6.28 kcal/mol in the range of 22$^{\circ}C$ to 4$0^{\circ}C$. A oolf plot showed that the enzyme reaction follows Michaelis-Menten equation, whose {TEX}$K_{M}${/TEX} and {TEX}$V_{max}${/TEX} values were 4.65$\times${TEX}$10^{-3}${/TEX} M and 0.89$\mu$ mol/mg-min respectively.

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The Allelopathic Effects of Aqueous Extracts of Hypochaeris radicata L. on forage Crops (서양금혼초(Hypochaeris radicata L.)의 수용추출물이 사료작물에 미치는 allelopathy 효과)

  • Kim Og-Yim;Park Sun-Ill;Jung Ill-Min;Ha Sang-Young
    • Journal of Life Science
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    • v.15 no.6 s.73
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    • pp.871-878
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    • 2005
  • This experiment was performed to examine the allelopathy effect of allelochemical substance on the crop plants. According to the experiment of the allelochemical substances in Hypochaeris radicata by HPLC, there are the differences at each part of plants. However, it is ascertained that there are 14 kinds of phenolic compounds ingredients that are $\rho$-hydroxybenzoic acid, chlorogenic acid, catechin, caffeic acid, syringic acid, salicylic acid, $\rho$-coumaric acid, ferulic acid, naringin, hesperidin, myricetin, trans-cinnamic acid, quercetin and naringenin. The chemicals like caffeic acid, ferulic acid, and naringenin are commonly included. The result of the chemical experiment shows that there are the differences at each season and part of plants. The leaves in May and blossoms and roots in July contain lots of phenolic acids. It is very high contents such as salicylic acid 2085.6 ${\mu}g/g$ and quercetin 1522.0 ${\mu}g/g$, especially in roots of plants. The result on the growth of crop plants treated by the aqueous extract of Hypochaeris radicata shows that the value of the control group and the test group are same in some cases. However, because the treat value of test group is towel'than that of control group in all items of the experiment, it is cofirmed that the growth of crop plants was inhibited and that the inhibitory effect was increased as its density of treatment was increased. The result of change in quantity shows that there are the differences at each kind of crop plants, but the inhibitory effect was increased as its concentration of treatment was increase with entire. As results, it is confirmed that H. radicata has the allelopathy effect to the crop plants. Especially the inhibitory effect on growth is high in gramineous crop, italian ryegrass and leguminous crop. purple alfalfa.

Effects of High Pressure Treatment on Antioxidant Compounds and Activity of Germinated Rough Rice (Oryza sativa L.) (고압처리가 발아벼의 항산화 성분과 활성에 미치는 영향)

  • Kim, Min Young;Lee, Sang Hoon;Jang, Gwi Young;Park, Hye Jin;Meishan, Li;Kim, Shinje;Lee, Youn Ri;Lee, Junsoo;Jeong, Heon Sang
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.42 no.11
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    • pp.1783-1791
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    • 2013
  • This study is investigated to evaluate the enhancement of antioxidant compound and activity of rough rice with different germination periods and high pressure treatment. The subject was germinated at $37^{\circ}C$ for 6 days (HP0), and then the germinated rough rice were subjected to 30 MPa for 24 hr (HP24) and 48 hr (HP48), respectively. HP0, HP24 and HP48 samples were prepared and extracted with 80% ethanol. The highest total polyphenol contents (5.15 mg/g) occurred in treating at HP48 after germination for 5 days. The total phenolic acid contents including gallic acid, chlorogenic acid, catechin, ${\rho}$-coumaric acid, ferulic acid, salicylic acid, naringin, myricetin, trans-cinnamic acid, naringenin and kaempferol increased from $37.26{\sim}204.32{\mu}g/g$ at HP0 to $77.29{\sim}283.05{\mu}g/g$ at HP48. In antioxidant activity analyses, HP48 extracts showed higher values in ABTS and DPPH radical scavenging activity, reducing power, and $Fe^{2+}$ iron chelating effect than those of the HP24 and HP0 extracts. These results suggest that the combined treatment of high pressure treatment and germination process efficiently enhanced antioxidant compound and activity of rough rice.

A Major Antioxidative Components and Comparison of Antioxidative Activities in Black Soybean (검정콩의 주요 항산화 원인물질 및 항산화 효과의 비교)

  • Kim, Sun-Hee;Kwon, Tai-Wan;Lee, Young-Soon;Choung, Myoung-Gun;Moon, Gap-Soon
    • Korean Journal of Food Science and Technology
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    • v.37 no.1
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    • pp.73-77
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    • 2005
  • Contents of isoflavone, phenolic acids, tocopherol, and anthocyanin in black soybean (Glycine max) were measured by HPLC. To compare antioxidative activities of main black soybean components, antioxidative effects of the same levels of commercial standard components were measured by Trolox equivalent antioxidant capacity assay (TEAC). Most effective component was gentisic acid followed by anthocyanin, p-coumaric acid, ferulic acid, genistein, syringic acid, and daidzein. TEAC assay results revealed genistein in isoflavone, gentisic acid in phenolic acids, p-tocopherol in tocopherol, and anthocyanin showed highest antioxidative and synergistic acitivities, with anthocyanin showing strongest synergy effect.