• Title/Summary/Keyword: Cinnamic acid

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Preparation of Fully Substituted 1,3,4-Oxadiazole Derivatives from N-Isocyaniminotriphenylphosphorane, (E)-Cinnamic Acids, Chloroacetone and Primary Amines

  • Ramazani, Ali;Nasrabadi, Fatemeh Zeinali;Karimi, Zahra;Rouhani, Morteza
    • Bulletin of the Korean Chemical Society
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    • v.32 no.8
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    • pp.2700-2704
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    • 2011
  • The 1:1 imine intermediate generated by the addition of primary amine to chloroacetone is trapped by N-isocyaniminotriphenylphosphorane in the presence of (E)-cinnamic acids and the corresponding iminophosphorane intermediate was formed. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

Determination of Phenolic Compounds Responsible for Allelopathy in Upland Weeds (밭 잡초(雜草)중에 존재(存在)하는 Allelopathy 관련(關聯) Phenol 화합물(化合物)의 검색(檢索))

  • Chon, J.C.;Han, K.W.;Jang, B.C.;Shin, H.S.
    • Korean Journal of Weed Science
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    • v.8 no.3
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    • pp.258-264
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    • 1988
  • Phenolic compounds present in upland weeds (Artemisia asiatica Nakai, Capsella bursa-pastoris (L.) Medik, Portulaca orleracea L. and Trifolium repens L.) which have shown allelopathic activity were determined using paper chromatography (PC) and high performance liquid chromatography (HPLC). Effect of the determined phenolic compounds on germination and post-germination growth of test plants was also investigated. Kinds of phenolic compounds determined by PC in the four weed species were greater in the aqueous extract than in the methanol extract. Ferulic acid was found in both extracts of the weeds studied, whereas benzoic acid was that the weeds commonly contained hydroquinone, p-hydroxybenzoic, ferulic and cinnamic acids. Out of the phenolic compounds determined by PC and HPLC p-hydroxybenzoic, cinnamic and ferulic acids inhibited germination and post-germination growth of radish and sesame. Inhibition of the phenolic compounds on the radicle growth was greater than on the germination of the test plants.

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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.

Analysis of Cinnamic Acid, Cinnamaldehyde and 2-Methoxycinnamaldehyde in Cinnamomi Ramulus on the Market in Seoul by HPLC (서울시내 유통 중인 계지의 지표성분 함량분석)

  • Lee, Jeong-Sook;Lee, Sung-Deuk;Hwang, Kwang-Ho;Kim, Hee-Soon;Yoo, In-Sil;Han, Ki-Young;Chae, Young-Zoo
    • YAKHAK HOEJI
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    • v.57 no.4
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    • pp.235-240
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    • 2013
  • For the quality control of traditional herbal medicine, Cinnamomi Ramulus, simultaneous determination of cinnamic acid, cinnamaldehyde, and 2-methoxycinnamaldehyde was established by using a high performance liquid chromatographic (HPLC) method with diode array detector. To separate three constituents, Eclipse XDB C18 ($5{\mu}m$, $4.6{\times}250mm$) was used with 0.1% acetic acid and acetonitrile. Validation of the chromatography method was evaluated by linearity, recovery, and precision test. Calibration curve of standard components showed excellent linearity ($R^2$ >0.9999). A simple and efficient method by HPLC was developed to evaluate the quality of traditional herbal medicines made from Cinnami Ramulus. Three major bioactive ingredients in 30 samples that are from China(8) and Vietnam(22) were separated and quantified.

Allelopathy and Quantification of Causative Allelochemicals in Sweet Potato

  • Chon, Sang-Uk
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.48 no.5
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    • pp.402-406
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    • 2003
  • Greenhouse and laboratory studies were conducted to determine the allelopathic potentials of extracts or residues from sweet potato (Ipomoea batatas L. (Lam). The extracts applied on filter paper in a Petri dish bioassay significantly inhibited root growth of alfalfa. Aqueous leachates at 40g dry tissue $\textrm{L}^{-1}$ (g $\textrm{L}^{-1}$) from leaves showed the highest inhibition against alfalfa, and followed by stems and roots. Alfalfa root growth was significantly inhibited by methanol extracts of the same plants as the concentration increased. The effect of residue incorporation into soil on seedling growth of com, soybean, barnyard grass and eclipta was examined in the greenhouse, and results showed that the leaf residues at 200g $\textrm{kg}^{-1}$ by plant parts inhibited shoot dry and root dry weights of test plants by 60-80%. By means of HPLC, causative allelopathic substances present in plant parts of sweet potato "Sinyulmi" were identified as coumarin, trans-cinnamic acid, o-coumaric acid, p-coumaric acid, and chlorogenic acid. Total content of these compounds for leaves extracts were detected as the greatest amount in EtOAc fraction, especially trans-cinnamic acid was the greatest component. These results suggest that sweet potato plants have herbicidal potentials, and that their activities exhibit differently depending on plant parts.ant parts.

Monoamine Oxidase Inhibitors from Cinnamomi Cortex

  • Huong, Dang Thi Lan;Jo, Young-Su;Lee, Myung-Koo;Bae, Ki-Hwan;Kim, Young-Ho
    • Natural Product Sciences
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    • v.6 no.1
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    • pp.16-19
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    • 2000
  • Four compounds were isolated from the dichloromethane fraction of Cinnamomi Cortex through bioassay-guided isolation. Their structures were identified as coumarin (1), 3,3-dimethoxy-1-propenyl benzene (2), cinnamic acid (3) and o-methoxy cinnamaldehyde (4) on the basis of spectroscopic data. All four compounds showed inhibitory activities in vitro against monoamine oxidase (MAO) prepared by mouse brain. The $IC_{50}$ values were $41.4\;{\mu}M\;(1),\;110.6\;{\mu}M\;(2),\;252.5\;{\mu}M\;(3)\;and\;83.1\;{\mu}M$ (4), respectively.

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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.

Inhibitory Action of Cinnamic Acid Derivatives on Heterologous Passive Cutaneous Anaphylaxis

  • Lee, Ji-Yun;Kim, Youn-Joung;Yoon, Mi-Yun;Sim, Sang-Soo;Kim, Chang-Jong
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.195.2-196
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    • 2003
  • Cinnamic acid derivatives (CAD) originating from medicinal plants have some biological activity. In this study. effect of CAD on heterologous passive cutaneous anaphylaxis (PCA) were studied by the method of Levine and Vaz(1970). Anti-serum was prepared from OA-sensitized male Balb/c mouse at two weeks after the last challenge of ovalbumin (OA) and alumina gel, and these serum diluted with HEPES buffer by means of the heterologous PCA titer, i.e. the highest dilution inducing PCA in rats. (omitted)

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Inhibitory Action of Cinnamic Acid Derivatives on Reversed Cutaneous Anaphylasis and Hemolysin Titer

  • Kim, Tae-Doo;Lee, Ji-Yun;Kim, Youn-Joung;Lee, Jin-Hee;Sim, Sang-Soo;Kim, Chang-Jong
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.196.1-196.1
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    • 2003
  • Cinnamic acid derivatives(CAD) originating from vegetable kingdom have some biological activity. Effect of CAD on reversed cutaneous anaphylaxis (RCA) and hemolysin (HY) titer were studied in rats. Experiments were carried out to determine RCA as the skin edema induced at 2 hours after injection of 0.05 $m\ell$/site of anti-rat serum rabbit serum. Drugs were orally administered at one hour before antigen challenge. (omitted)

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Preparation and Characterizations of Complex Composed of ${\beta}$-Cyclodextrin Polymer/Cinnamic Acid (베타-사이클로 덱스트린 중합체/신남산 복합체의 제조 및 특성 연구)

  • Mok, Eun Young;Cha, Hyun Ju;Kim, Jin-Chul
    • Applied Chemistry for Engineering
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    • v.23 no.5
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    • pp.462-466
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    • 2012
  • $\beta$-cyclodextrin ($\beta$-CD) polymers were prepared in a strong alkali condition solution (NaOH solution 30% (w/v)) using epichlorohydrin (EPI) as a cross-linker, and the molar ratio of EPI to $\beta$-CD was 10 : 1. The $\beta$-CD content in $\beta$-CD polymers is about 52%. In order to get the photo-responsible and pH-responsible, cinnamic acid was added to be inserted into the cavities of $\beta$-CD due to the hydrophobic interaction. The complex formation was confirmed using transmission electron microscope. The dimerization degree of complexes increased under UV irradiation at $\lambda$ = 365 nm but decreased under the UV irradiation at $\lambda$ = 254 nm. Dynamic light scattering analysis of particle sizes showed that the sizes of complexes did not change with different UV wavelength. Moreover, the complexes were pH-responsible because of the carboxyl group of cinnamic acid, but the size and zeta potential of the complex did not change in strong acid and alkali conditions.