• Title/Summary/Keyword: trans-Cinnamic acid

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Screening of Phenolic Compounds with Inhibitory Activities against HMG-CoA Reductase (페놀 화합물로부터 HMG-CoA reductase 저해 활성 물질 탐색)

  • Son, Kun Ho;Lee, Ju Yeon;Lee, Jeong Soon;Kang, Sam Sik;Sohn, Ho Yong;Kwon, Chong Suk
    • Journal of Life Science
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    • v.27 no.3
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    • pp.325-333
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    • 2017
  • High level of plasma cholesterol is strongly associated with the development of atherosclerosis and coronary heart disease. Clinical trials designed to reduce plasma cholesterol level by diet or pharmacological intervention have resulted in marked reduction of disease incidence. The enzyme 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase which reduces cholesterol biosynthesis in the liver is the key enzyme of the mevalonate pathway that produces cholesterol. In this study, 71 naturally occurring phenolic compounds were tested for inhibitory activities against HMG-CoA reductase. Eleven compounds out of 71 showed inhibitory activities: three hydrolyzable tannin (geraniin, acetonyl geraniin and pentagalloyl ${\beta}-D-glucose$), four benzoic acid derivatives (benzoic acid, trans-cinnamic acid, 2,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid), and four naphthoquinone derivatives (1,2-naphthoquinone, 1,4-naphthoquinone, plumbagin and shikonin). At the concentration of $10{\mu}g/ml$, 1,4-naphthoquinone inhibited HMG-CoA reductase by 99.4%, and then plumbagin 91.4%, pentagalloyl ${\beta}-D-glucose$ 46.6%, 2,4-dihydroxybenzoic acid 40.9%, shikonin 37.7%, 1,2-naphthoquinone 36.6%, trans-cinnamic acid 32.0%, acetonyl geraniin 30.2%, benzoic acid 28.5%, geraniin 28.3% and 2,5-dihydroxybenzoic acid 22.3%, respectively. $IC_{50}$ values of 1,4-naphthoquinone and plumbagin was $2.1{\mu}g/ml$ and $5.8{\mu}g/ml$, respectively.

Assessment on Antioxidant Properties of Oplopanax elatus Nakai in vitro

  • Kim, Jun-Heong;Eom, Seok-Hyun;Lee, Han-Shin;Kim, Jae-Kwang;Yu, Chang-Yeon;Kwon, Yong-Soo;Lee, Ju-Kyong;Kim, Myong-Jo
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.2
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    • pp.112-119
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    • 2007
  • Effects of Oplopanax elatus have known to various pharmaceutical therapies. However, chemical prosperities in the plant are rarely investigated. In order to detect biological activity, we evaluated the antioxidant activity of five fractions from methanolic extracts in each part of O. elatus. Also, contents of polyphenols and polysaccharides were measured. Five fractions were of sub-fractions using n-hexane, ethyl-acetate, n-butanol, and water from methanolic extracts. Ethylacetate and n-butanol fractions from stem and root exhibited strong antioxidant activity and high total phenolics content. On the HPLC analysis, ten free phenolics, including p-hydroxybenzoic acid, chlorogenic acid, caffeic acid, syringic acid, p-cou maric acid, ferulic acid, naringin, hesperidin, quercetin and trans-cinnamic acid, were identified from the fractions and were shown to different quantitative proportions. Furthermore, ethylacetate and n-butanol fraction had the highest amount of chlorogenic acids, one of the cinnamic acid derivatives possessing pharmacological properties. These results indicated that the fractions of O. elatus, as well as methanolic extracts, could be used as natural antioxidative ingredients.

Determination of Biosynthetic Pathway of Decursin in Hairy Root Culture of Angelica gigas

  • Ji, Xiuhong;Huh, Bum;Kim, Soo-Un
    • Applied Biological Chemistry
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    • v.51 no.4
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    • pp.258-262
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    • 2008
  • To establish the biosynthetic pathway of decursin in Angelica gigas Nakai, feeding experiment with stable isotope-labeled precursors were conducted. Umbelliferone and decursin were labeled with deuterium at C-3. The umbelliferone, the decursin, and other commercially available putative precursors, L-phenylalanine-ring-$d_5$ and trans-cinnamic acid-$d_7$, were fed to the hairy root culture of A. gigas. Each deuterated compound was incorporated into decursinol, decursinol angelate, and decursin as determined by mass spectrometric analysis. These findings confirmed the coumarin biosynthesis pathway sequence is composed of phenylalanine, cinnamic acid, umbelliferone, decursinol, and decursin.

Antioxidant Activities of Naturaceuticals Extract In Vitro

  • Park, Sung-Jin;Kwon, Woo-Taeg;Rha, Young-Ah
    • Culinary science and hospitality research
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    • v.20 no.5
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    • pp.29-33
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    • 2014
  • In this study, we examined the antioxidant activity of the naturaceutical extract in vitro using total phenolic contents, total flavonoids contents, DPPH radical scavenging activity, reducing power assay, and phenolic acid contents. The total phenolic and total flavonoids contents of naturaceutical extract were 5.46 mg/g, 2.21 mg/g, respectively. The DPPH radical scavenging activity of natraceutical extract varied from 18.77 ($200{\mu}g/mL$) to 3.44 ($1,000{\mu}g/mL$). The reducing power of the natraceutical extract absorbance varied from 1.07 (0.78 mg/mL) to 3.44 (12.5 mg/mL), and reducing power of extract presented a concentration-dependent activity increase. The highest amounts of trans-ferulic acid, p-hydroxybenzoic acid, p-coumaric acid, vanillin, vanillic acid, p-hydroxybenzaldehyde, and trans-cinnamic acid were observed in the naturaceutical extract at the levels of 750.79, 619.75, 531.34, 222.04, 219.28, 107.40, and $89.56{\mu}g/g$, respectively. The results imply that this antioxidant effect of the naturaceuticals extract could be harnessed in the management and prevention of degenerative diseases associated with oxidative stress.

L-phenylalanine ammonia-lyase activity of fungi, yeasts and streptomyces (Fungi, 이스트, 그리고 streptomyces에서 L-phenylalanine ammonia-lyase의 활성도 비교)

  • 장지영;구양모;김공환
    • Korean Journal of Microbiology
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    • v.26 no.3
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    • pp.270-277
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    • 1988
  • Microorganisms isolated from soil (150 strains), fungi (39 strains), yeasts (9 strains) and Streptomyces species (39 strains) were assayed for L-phenylalanine ammonia-lyase(PAL) activity. 17 strains of fungi and 46 strains of soil isolates were proved to produce PAL, Aspergillus panamensis, Penicillium varioti and 11 soil isolates showed comparatively large PAL activity. When PAL activity was assayed with cell-free extracts of these 13 strains and 7 strains of Rhodotorula and Rhodosporidium geni, Rhodosporidium toruloides (IFO 0559) showed the highest PAL activity with 0.333 units per g of the wet cell weight.

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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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Antioxidative Effectiveness of Extract of Nut and Leaf of Ginkgo biloba L. (은행(Ginkgo biloba L.) 종실 및 잎 추출물의 항산화 효과에 관하여)

  • Bae, Jae Oh;Lee, Gee Dong;Kim, Jeong Sook;Yoon, Hyung Sik
    • Current Research on Agriculture and Life Sciences
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    • v.9
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    • pp.61-69
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    • 1991
  • Free phenolic acid, esterified and insoluble phenolic acid extract were extracted from Ginkgo nuts and leaves. Antioxidative effectiveness was measured by Peroxide value and TBA value at each extract, control, 0.02%(w/w) BHA and BHT in corn oil, at $45{\pm}1^{\circ}C$ and dark thermo static oven for 45 days. Laboratory tube was added by BHA, BHT, separated free phenolic acids, esterified and insoluble-bound phenolic acid extract of Ginkgo nuts and leaves 127, 95, 140, 121, 280 meq/kg, oil. On the other hand, at the same condition TBA values of each antioxidative matter were 0.430, 0.153, 0.059, 0.175, 0.260, 0.187, 0.160, 0.174, 0.195. This result remarkably appeared antioxidative effectiveness in corn oil substrate, ${\rho}$-Hydroxybenzoic acid, Syringic acid, Gallic acid, Protocatechuic acid, Pyrogallol, Caffeic acid, Coumaric acid, trans-Cinnamic acid, Phloroglucinol.

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Development of trans-cinnamaldehyde self-microemulsifying drug delivery system(SMEDDS) with superior stability (안정성이 우수한 신남알데히드 자가미세유화 약물전달시스템 개발)

  • Bang, Kyu-Ho;Kim, Kyeong Soo
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.20 no.12
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    • pp.555-562
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    • 2019
  • This study was undertaken to develop a stable self-microemulsifying drug delivery system (SMEDDS) for trans-cinnamaldehyde, a known antibacterial and antifungal agent. A simultaneous analytical method was established for quantification of trans-cinnamaldehyde and its degradant, cinnamic acid. Various surfactants were applied to assess their effect on the aqueous solubility of trans-cinnamaldehyde, and pseudo-ternary phase diagrams were plotted. Of the various formulations tested, the liquid SMEDDS composed of trans-cinnamaldehyde (oil), Cremophor EL (surfactant) and Transcutol P (cosurfactant) at a volume ratio of 10/70/20, produced the smallest emulsion droplet size (around 23 nm). The stability test determined the superior stability of the trans-cinnamaldehyde SMEDDS with constant trans-cinnamaldehyde content and z-average diameter of emulsion, under accelerated and heat stressed condition. Thus, we believe that this novel trans-cinnamaldehyde SMEDDS formulation has the potential to be applied for the development of trans-cinnamaldehyde medicines in the pharmaceutical industry.

Cytotoxic and Mutagenic Effects of Cinnamomum cassia Bark-Derived Materials

  • LEE , HOI-SEON;KIM, SUN-YEOU;LEE, CHI-HOON;AHN, YOUNG-JOON
    • Journal of Microbiology and Biotechnology
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    • v.14 no.6
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    • pp.1176-1181
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    • 2004
  • The cytotoxic activities of Cinnamomum cassia (Blume) bark-derived materials toward six human HeLa epithelioid cervix, A549 lung, SK-OV-3 ovarian, SK-MEL-2 melanoma, XF-498 central nerve system, and HCT-15 colon tumor cell lines were evaluated by using sulforhodamine B assay and compared to those of the anticancer agents, cisplatin and mitomycin C. The biologically active constituent of the Cinnamomum bark was characterized as trans­cinnamaldehyde by spectroscopic analysis. The cytotoxic activity of cinnamaldehyde against HeLa, SK-MEL-2, and HCT -15 cell lines was comparable to that of cisplatin and mitomycin C. The compound showed lower activity against A549, SK-OV-3, and XF-498 cell lines than the anticancer agents. Eugenol exhibited moderate activity against SK-OV­3, XF-498, and HCT-15 tumor cells, and trans-cinnamic acid, cinnamyl alcohol, $\alpha-pinene,\;and\;\beta-pinene$ showed little or no activity against model tumor cells. Cinnamaldehyde was not mutagenic against four strains (TA 98, TA 100, TA 1535, and TA 1537) of Salmonella typhimurium (Castel and Chalm). These results indicate at least one pharmacological action of C. cassia.

Phytotoxic Effect of Lettuce (Lactuca sativa L.) Leaf Extract on Seedling Growth of Crops and Weeds

  • Chon, Sang-Uk;Choi, Seong-Kyu
    • Plant Resources
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    • v.7 no.1
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    • pp.69-76
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    • 2004
  • Lettuce (Lactuca sativa L.) is known to contain water-soluble substances that are biologically active. Aqueous or methanol extracts and residues from leaves of lettuce plants were assayed to determine their allelopathic effects, and the causative allelochemicals from fractions were quantified by means of HPLC analysis and bioassayed. Extracts from oven-dried leaf samples were more phytotoxic than those from freeze-dried samples. Leaf extracts of 40 g L$^{-1}$ were completely inhibitory on root growth of alfalfa (Medicago sativa L.), while root growths of barley (Hordeum vulgare L.) and soybean (Glycine max L.) were less sensitive. Early seedling growth of both alfalfa and barnyard grass (Echinochloa crus-galli) was significantly reduced by methanol leaf extracts. The major allelopathic substances analyzed by HPLC were coumarin, trans-cinnamic acid, o-coumaric acid, p-coumaric acid and chlorogenic acid. Of them p-coumaric acid was found as the greatest amount (8.9 mg 100 g$^{-1}$ ) in the EtOAc fraction; only coumarin was found in all the fractions. Hexane and EtOAc fractions of L. sativa reduced alfalfa root growth more than did BuOH and water fractions. These results suggest that lettuce had potent herbicidal activity, and that its activity differed depending on type and amount of causative compounds by fraction.

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