• Title/Summary/Keyword: Caffeic acid derivatives

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Choleretic activities of coumarins and their biological precursors (Coumarin계물질 및 그 전구체의 담즙분비촉진 효과에 관한 연구)

  • 한덕용
    • YAKHAK HOEJI
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    • v.13 no.2_3
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    • pp.67-70
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    • 1969
  • Gall duct cannulated rats were given daphnetin, umbelliferone, 4-hydroxy-coumarin, dicoumarol, 4,7-dihydroxycoumarin, 4,7-dimethyl-5-hydroxy-coumarin, coumarin-3-carboxylic acid, cinnamic acid, ferulic acid, caffeic acid by duodenal catheter at room temperature and output of bile flow was detected. All of the subjected compounds in this experiment indicated a significant effect on the biliary elimination except cinnamic acid alone. It is suggested that a relationship exists between chemical pattern and biological activity for coumarin derivatives and their precursors, and that the choleretic activity of these compounds requires hydroxylated cinnamic acid structure as the most fundamental chemical pattern.

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Anti-oxidative and Antibacterial Constituents from Sedum hybridum

  • Gendaram, Odontuya;Choi, Yoen-Hee;Kim, Young-Sup;Ryu, Shi-Yong
    • Natural Product Sciences
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    • v.17 no.4
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    • pp.279-284
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    • 2011
  • Phytochemical studies on the whole extract of Sedum hybridum L., a Mongolian medicinal plant, has been undertaken to isolate active principles responsible for its anti-oxidative and antibacterial activities. Eighteen known compounds, i.e. (1) quercetin, (2) kaempferol, (3) herbacetin-8-O-${\beta}$-D-xylopyranoside, (4) myricetin, (5) gossypetin-8-O-${\beta}$-D-xylopyranoside, (6) gallic acid, (7) 2,4,6-tri-O-galloyl-D-glucopyranose, (8) 6-O-galloylarbutin, (9) myricetin-3-O-${\alpha}$-L-arabinofuranoside, (10) quercetin-3-O-${\alpha}$-L-arabinofuranoside, (11) caffeic acid, (12) ethylgallate, (13) (-) epigallocatechin-3-O-gallate, (14) palmitic acid, (15) stearic acid, (16) stearic acid ethyl ether, (17) ${\beta}$-sitosterol and (18) ${\beta}$-sitosteryl-O-${\beta}$-D-glucopyranose have been isolated and their molecular structures identified by spectroscopic analysis. Thirteen substances including seven flavonol components (1, 2, 3, 4, 5, 9 and 10), five gallic acid derivatives (6, 7, 8, 12 and 13) and caffeic acid (11) exhibited significant, dose-dependent, DPPH radical scavenging activity. Galloyl esters 12 and 13 were revealed to be main active principles for the antibacterial property of the extract of Sedum hybridum L.

Phytochemical Constituents of Lonicera maackii Stems (괴불나무(Lonicera maackii) 줄기의 성분)

  • An, Gye Yeong;Chung, Sung Woo;Cho, Hee Chan;Park, Jin Ryoung;Kim, Myong Jo;Kim, Hyun Pyo;Yang, Hee Jung;Chun, Wanjoo;Kwon, Yongsoo
    • Korean Journal of Pharmacognosy
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    • v.49 no.2
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    • pp.103-107
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    • 2018
  • Two phenylpropanoids, three caffeoylquinic acid deravatives and an iridoid were isolated from the stem of Lonicera macckii. On the basis of physico-chemical data, these compounds were identified as caffeic acid methyl ester(1), 5-caffeoylquinic acid n-butyl ester(2), methyl 3,4-dicaffeoyl quinate(3), 3,5-dicaffeoyl quinic acid n-butyl ester(4), loganin (5) and caffeic acid(6). All compounds were isolated for the first time from the stem of this plant.

Anti-inflammatory Effects of Chitosan-phytochemical Conjugates against Propionibacterium acnes-induced Inflammation (Propionibacterium acnes에 의해 유도된 염증에 대한 Chitosan-phytochemical Conjugates의 항염증 효과)

  • Kim, Ji-Hoon;Je, Jae-Young;Kim, Young-Mog
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.49 no.5
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    • pp.589-593
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    • 2016
  • Propionibacterium acnes infection in skin tissue often causes acne vulgaris, commonly characterized by inflammatory papules, pustules, and nodules. Chitosan and its derivatives possess strong anti-inflammatory effects. In this study, the anti-inflammatory activity of chitosan-phytochemical conjugates on P. acnes-infected human skin keratinocytes (HaCaT) was evaluated. We designed a model of P. acnes-induced inflammation in viable HaCaT cells. Nitric oxide (NO), an inflammatory marker, was successfully elevated by P. acnes infection in HaCaT cells in a dose-dependent manner. Furthermore, the levels of NO were reduced by treatment with chitosan-phytochemical conjugates (chitosan-caffeic acid, -ferulic acid and -sinapic acid) in a dose-dependent manner. Among these conjugates, chitosan-caffeic acid exhibited the strongest NO suppression in HaCaT cells infected with P. acnes. The results obtained in this study suggest that chitosan-phytochemical conjugates could be used as a potential therapeutic agent against acne vulgaris.

Design and Synthesis of Chromenone derivatives as Potential Antioxidants

  • Kang, Hae-Eun;Lee, Kum-Ho;Lee, Dae-Hee;Cho , Jung-Sook;Lee, Hee-Soon
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.351.3-353
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    • 2002
  • Oxygen radicals are produced in many pathophysiologic states whether the event is a causal factor of illness or is a result of their progression. Oxygen radicals including superoxide anions. hydrogen peroxide are thought to be involved in a number of type of acute. and chronic pathologic condition in the brain and neural tissue. So the antioxidants have recently received much attention as therapeutic agent for the treatment of neurodegenerative disease. In this study. we describe synthesis of a series of chromenone derivatives as antioxidant agents. The target compounds are designed to include the structural frature of caffeic acid. flavoniod. and focopherol known as antioxidants.

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Auxin Affects on Production of Adventitious Roots and Secondary Metabolites in Echinacea angustifolia (오옥신 처리가 에키네시아의 부정근 및 생리활성물질 생산에 미치는 영향)

  • Jang, Young Se;Cui, Hai Yan;Lee, Eun Jung;Kim, Hae Won;Paek, Kee-Yoeup
    • Korean Journal of Medicinal Crop Science
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    • v.20 no.6
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    • pp.479-486
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    • 2012
  • The production of adventitious roots derived from root explant of Echinacea angustifolia and its secondary metabolite content were assessed in different types and levels of auxin. The induction of adventitious roots from root explant cultured in Murashige and Skoog solid medium supplemented with 1.0 mg/L indole -3-butyric acid (IBA) attained highest as 20.87 mg fresh weight and 3.07 mg dry weight per culture but root suspension culture at the same concentration of IBA enhanced biomass production as 3.07 g fresh weight and 0.38 g per culture after 4 weeks in culture. 3.0 mg/L ${\alpha}$-naphthalene acetic acid (NAA) treatment had similar effect on root biomass production as 3.07 g fresh weight and 0.38 g per culture with liquid suspension culture, whereas adventitious roots exposed to over 3.0-5.0 mg/L IBA or 5.0 mg/L NAA were less responsive by reducing the number of adventitious roots and/or changing root morphology such as short and thick. The content of secondary metabolites such as phenolic, flavonoids and total caffeic acid in adventitious roots cultured on MS medium supplemented with 1.0 mg/L IBA were attained highest as 27.20, 9.60. 10.67 mg/g dry weight, respectively. Overall, the best production of root biomass and secondary metabolites were given by 1.0 mg/L IBA.

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.

Analysis of Phenolic Acids in Tobacco Leaf by GC/MS (GC/MS에 의한 잎담배중 Phenolic Acid의 분석)

  • 박진우
    • YAKHAK HOEJI
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    • v.26 no.2
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    • pp.129-132
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    • 1982
  • A GC/MS method was developed to analyze phenolic acid extract from tobacco leaf. Extracted acids were converted to their methyl esters by refluxing with 3M hydrogen chloride in methanol, and the esters were reacted with his (trimethylsilyl) trifluoroacetamide plus 10% trimethylchlorosilane to silylate the phenolic groups. Derivatives of standard salicylic, p-hydroxybenzoic, vanillic, gentisic, p-coumaric, syringic, ferulic, and sinapic acids prepared by this procedure were analyzed by GC/MS on $20m{\times}0.2mm$ column of SE-54 glass capillary. GC/MS analysis of the extract from tobacco leaf revealed the presence of salicylic, p-hydtoxybenzoic, vanillic, gentisic, protocatechuic, p-coumaric, syringic, gallic, ferulic, caffeic, sinapic, and quinic acids, respectively. The quantitative analysis of these phenolic acids were achieved by using multiple ion selection technique.

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Phenolic Acids and Antioxidant Activities of Wild Ginseng (Panax ginseng C. A. Meyer) Leaves

  • Seog, Ho-Moon;Jung, Chang-Hwa;Kim, Yoon-Sook;Park, Hyeon-Suk
    • Food Science and Biotechnology
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    • v.14 no.3
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    • pp.371-374
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    • 2005
  • The compositions and antioxidant activities of tree and hydrolyzed phenolic acids, which are aglycones of esterified phenolic acids, in wild ginseng leaves were investigated. The contents of tree and hydrolyzed phenolic acids in the wild ginseng leaves were $422.4\;{\pm}\;3.5$ and $319.6\;{\pm}\;5.7\;mg/100\;g$, respectively, as gallic acid equivalents. Free phenolic acids were composed of 55.3% benzoic acid derivatives and 44.6% phenylpropanoids. The major constituents of free phenolic acids in the ginseng leaves were syringic (139.4 mg/l00 g) and sinapic (131.2 mg/100 g) acids. On the other hand, hydrolyzed phenolic acids in the ginseng leaves were mainly composed of caffeic (59.4 mg/100 g), ferulic (49.5 mg/100 g), and p-coumaric (33.8 mg/100g) acids. Phenylpropanoid content was higher (82.7%) than benzoic acid derivatives (17.3%). $IC_{50}$ values of DPPH radical scavenging activity were $10.2\;{\mu}g/mL$ for tree phenolic acids and 8.0 mg/mL for hydrolyzed phenolic acids, as gallic acid equivalents. Hydrolyzed phenolic acids also exhibited higher hydroxyl and superoxide radical scavenging activities than free phenolic acids did. These results indicated that the antioxidant activities of the wild ginseng leaves were correlated more closely with phenylpropanoid contents than with total amount of phenolics.

Methyl p-Hydroxycinnamate Suppresses Lipopolysaccharide-Induced Inflammatory Responses through Akt Phosphorylation in RAW264.7 Cells

  • Vo, Van Anh;Lee, Jae-Won;Shin, Seung-Yeon;Kwon, Jae-Hyun;Lee, Hee Jae;Kim, Sung-Soo;Kwon, Yong-Soo;Chun, Wanjoo
    • Biomolecules & Therapeutics
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    • v.22 no.1
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    • pp.10-16
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    • 2014
  • Derivatives of caffeic acid have been reported to possess diverse pharmacological properties such as anti-inflammatory, anti-tumor, and neuroprotective effects. However, the biological activity of methyl p-hydroxycinnamate, an ester derivative of caffeic acid, has not been clearly demonstrated. This study aimed to elucidate the anti-inflammatory mechanism of methyl p-hydroxycinnamate in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. Methyl p-hydroxycinnamate significantly inhibited 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. Methyl p-hydroxycinnamate also suppressed LPS-induced overproduction of pro-inflammatory cytokines such as IL-$1{\beta}$ and TNF-${\alpha}$. In addition, methyl p-hydroxycinnamate significantly suppressed LPS-induced degradation of $I{\kappa}B$, which retains NF-${\kappa}B$ in the cytoplasm, consequently inhibiting the transcription of pro-inflammatory genes by NF-${\kappa}B$ in the nucleus. Methyl p-hydroxycinnamate exhibited significantly increased Akt phosphorylation in a concentration-dependent manner. Furthermore, inhibition of Akt signaling pathway with wortmaninn abolished methyl p-hydroxycinnamate-induced Akt phosphorylation. Taken together, the present study clearly demonstrates that methyl p-hydroxycinnamate exhibits anti-inflammatory activity through the activation of Akt signaling pathway in LPS-stimulated RAW264.7 macrophage cells.