• Title/Summary/Keyword: vanillic acid

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Isolation and Identification of 3-Methoxy-4-hydroxybenzoic acid and 3-Methoxy-4-hydroxycinnamic acid from Hot Water Extracts of Hovenia dulcis Thunb and Confirmation of Their Antioxidative and Antimicrobial Activity (헛개나무 열수추출물로부터 항산화 및 항미생물 활성을 갖는 3-methoxy-4-hydroxybenzoic acid 와 3-methyoxy-4-hydroxycinnamic acid의 분리 및 동정)

  • Cho, Jeong-Yong;Moon, Jae-Hak;Park, Keun-Hyung
    • Korean Journal of Food Science and Technology
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    • v.32 no.6
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    • pp.1403-1408
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    • 2000
  • The methanol soluble fraction of the hot water extracts from Hovenia dulcis Thunb showed antioxidative and antimicrobial activity. The methanol fraction was successively purified with solvent fractionation, silica gel adsorption column chromatography, Sephadex LH-20 column chromatography, and octadecylsilane column chromatography. The purified active substances were isolated by high performance liquid chromatography. The isolated substances were identified as 3-methoxy-4-hydroxybenzoic acid (vanillic acid) and 3-methoxy- 4-hydroxycinnamic acid (ferulic acid) by LC-MS and GC-MS. Vanillic acid and ferulic acid showed antimicrobial activity against Gram-positive bacteria, Gram-negative bacteria and yeast. The DPPH-radical scavenging activity of ferulic acid appeared more active than that of vanillic acid. DPPH-radical scavenging concentration of ferulic acid and vanillic acid were $14\;{\mu}g/mL\;(SC_{50})$, $100\;{\mu}g/mL\;(SC_{10})$, respectively.

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Vanillic Acid Stimulates Anagen Signaling via the PI3K/Akt/β-Catenin Pathway in Dermal Papilla Cells

  • Kang, Jung-Il;Choi, Youn Kyung;Koh, Young-Sang;Hyun, Jin-Won;Kang, Ji-Hoon;Lee, Kwang Sik;Lee, Chun Mong;Yoo, Eun-Sook;Kang, Hee-Kyoung
    • Biomolecules & Therapeutics
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    • v.28 no.4
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    • pp.354-360
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    • 2020
  • The hair cycle (anagen, catagen, and telogen) is regulated by the interaction between mesenchymal cells and epithelial cells in the hair follicles. The proliferation of dermal papilla cells (DPCs), mesenchymal-derived fibroblasts, has emerged as a target for the regulation of the hair cycle. Here, we show that vanillic acid, a phenolic acid from wheat bran, promotes the proliferation of DPCs via a PI3K/Akt/Wnt/β-catenin dependent mechanism. Vanillic acid promoted the proliferation of DPCs, accompanied by increased levels of cell-cycle proteins cyclin D1, CDK6, and Cdc2 p34. Vanillic acid also increased the levels of phospho(ser473)-Akt, phospho(ser780)-pRB, and phospho(thr37/46)-4EBP1 in a time-dependent manner. Wortmannin, an inhibitor of the PI3K/Akt pathway, attenuated the vanillic acid-mediated proliferation of DPCs. Vanillic acid-induced progression of the cell-cycle was also suppressed by wortmannin. Moreover, vanillic acid increased the levels of Wnt/β-catenin proteins, such as phospho(ser9)-glycogen synthase kinase-3β, phospho(ser552)-β-catenin, and phospho(ser675)-β-catenin. We found that vanillic acid increased the levels of cyclin D1 and Cox-2, which are target genes of β-catenin, and these changes were inhibited by wortmannin. To investigate whether vanillic acid affects the downregulation of β-catenin by dihydrotestosterone (DHT), implicated in the development of androgenetic alopecia, DPCs were stimulated with DHT in the presence and absence of vanillic acid for 24 h. Western blotting and confocal microscopy analyses showed that the decreased level of β-catenin after the incubation with DHT was reversed by vanillic acid. These results suggest that vanillic acid could stimulate anagen and alleviate hair loss by activating the PI3K/Akt and Wnt/β-catenin pathways in DPCs.

Production of Vanillic Acid from Vanillin by Pseudomonas sp. GD-088 (Pseudomonas sp. GD-088에 의한 Vanillin으로부터 Vanillic Acid의 생산)

  • 송정화;이일석;방원기
    • Microbiology and Biotechnology Letters
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    • v.22 no.6
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    • pp.672-678
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    • 1994
  • For production of vanillic acid from vanillin, optimum culture conditions for Pseudomo- nas sp. GD-088, having vanillin-oxidizing activity were investigated. The highest vanillin-oxidizing activity was obtained when this strain was cultured at 30$\circ$C for 24 hr in a medium consisting of 3.0 g/l xylose and 0.46 g/l NH$_{4}$CI (pH 7.0). When 18 g/l of whole Pseudomonas sp. GD-088 cells as the enzyme source was used in 50 mM phosphate buffer (pH 7.0) containing 3.0 g/l of vanillin, 2.463 g/l of vanillic acid was produced for 40 minutes. This amount of vanillic acid corresponds to a 90% yield, based on vanillin.

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Identification of phenolic antioxidative components in Terminalia Chebula Retz (가자 항산화성 물질의 분리 및 확인)

  • Kim, Jeong-Sook;Lee, Gee-Dong;Kwon, Joong-Ho;Yoon, Hyung-Sik
    • Applied Biological Chemistry
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    • v.36 no.4
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    • pp.239-243
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    • 1993
  • Chemical structures of phenolic antioxidative components of defatted Terminalia chebula R. were elucidated by used MS and H-NMR. The results showed that the phenolic antioxidative components were identified as ferulic acid, vanillic acid, p-coumaric acid in free-acid extracts, and caffecic acid, vanillic acid and p-coumaric acid in soluble-acid extracts, and caffeic acid, phloroglucinol and pyrogallol in insoluble-bound extracts, respectively.

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Genotoxic and Anti-Genotoxic Effects of Vanillic Acid Against Mitomycin C-Induced Genomic Damage in Human Lymphocytes In Vitro

  • Erdem, Merve Guler;Cinkilic, Nilufer;Vatan, Ozgur;Yilmaz, Dilek;Bagdas, Deniz;Bilaloglu, Rahmi
    • Asian Pacific Journal of Cancer Prevention
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    • v.13 no.10
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    • pp.4993-4998
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    • 2012
  • Vanillic acid, a vegetable phenolic compound, is a strong antioxidant. The aim of the present study was to determine its effects on mitomycin C-induced DNA damage in human blood lymphocyte cultures in vitro, both alone and in combination with mitomycin C (MMC). The cytokinesis block micronucleus test and alkaline comet assay were used to determine genotoxic damage and anti-genotoxic effects of vanillic acid at the DNA and chromosome levels. MMC induced genotoxicity at a dose of $0.25{\mu}g/ml$. Vanillic acid ($1{\mu}g/ml$) significantly reduced both the rates of DNA damaged cells and the frequency of micronucleated cells. A high dose of vanillic acid ($2{\mu}g/ml$) itself had genotoxic effects on DNA. In addition, both test systems showed similar results when tested with the negative control, consisting of dimethyl sulfoxide (DMSO) in combination with vanillic acid ($1{\mu}g/ml$)+MMC. In conclusion, vanillic acid could prevent oxidative damage to DNA and chromosomes when used at an appropriately low dose.

Antioxidant Effects of Phenolic Acids and Ginseng Extract in Aqueous System (수용성 계에서 Phenolic Acid류와 인삼 추출물이 갖는 산화방지 효과)

  • Lee, Hyung-Ok;Park, Ock-Jin
    • Korean Journal of Food Science and Technology
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    • v.30 no.2
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    • pp.434-438
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    • 1998
  • The antioxidant effects of 700 ppm ginseng extract, 100ppm caffeic acid, ferulic acid, vanillic acid, or ${\alpha}-topherol$ on the 1% linoleic acid aqueous buffer system was studied by measuring malondialdehyde (MDA) and headspace oxygen. The compounds showed antioxidant activities in the following order: $caffeic\;acid{\geq}ferulic\;acid\;>\;{\alpha}-tocopherol$>ginseng extract>vanillic acid, with the oxidation inhibition ratio of 63.5, 62.9, 52.3, 51.2 and 5.6% of the control according to MDA results. The mixture of 100 ppm caffeic acid, 100 ppm ${\alpha}-tocopherol$ and 700 ppm ginseng extract had a high oxidation inhibition ratio of 91.2%. Headspace oxygen results had a similar trend with the MDA results. Headspace oxygen results showed that the antioxidant activities were in order of ferulic acid>caffeic acid>${\alpha}-tocopherol$>ginseng extract>vanillic acid and headspace oxygen contents were 18.56, 17.78, 17.17, 16.65 and 15.95%, respectively.

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Analysis of the Degradation Products of Turmeric using GC-MS (GC-MS법을 이용한 울금의 퇴화물 분석)

  • Ahn, Cheun-Soon
    • Journal of the Korean Society of Clothing and Textiles
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    • v.31 no.6 s.165
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    • pp.859-868
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    • 2007
  • Degradation products of the dye extracted from turmeric and the turmeric dyed textiles were examined by using GC-MS after 100 oven (OV) and $H_2O_2/UV/O_2$(PER) treatments for up to 28 days. Throughout the OV degradation times, 2-propenoic acid, 3-(2-hydroxyphenyl)- was found consistently, while isovanillin, and vanillic acid were newly detected. In 28 day PER degradation sample, feruloylmethane, 2-propenoic acid, 3-(2-hydroxyphenyl)-, benzoic acid, and vanillic acid were detected as well as isovanillin. Feruloylrnethane, and 2-propenoic acid, 3-(2-hydroxyphenyl)- were detected from the degraded fabric samples. With the absence of curcuminoids in the GC-MS result, the decreasing pattern of 2-propenoic acid, 3-(2-hydrokyphenyl)- reflect the degradation of curcuminoids in turmeric extraction with the progression of OV degradation times. It is suggested that isovanillin, feruloylmethane, 2-propenoic acid,3-(2-hydroxyphenyl)-, and vanillic acid are the probable fingerprint products for determining the turmeric dye from the badly faded archaeological textiles.

Effects of Vaniltic Acid on the Cell Viability and Melanogenesis in Cultured Human Skin Melanoma Cells Damaged by ROS-Induced Cytotoxicity

  • Ha, Dae-Ho;Choi, Yong-Ja;Yoo, Sun-Mi
    • Biomedical Science Letters
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    • v.13 no.4
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    • pp.349-354
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    • 2007
  • The purpose of this study was to examine the effect of vanillic acid on the cell viability and melanogenesis in melanocytes damaged by reactive oxygen species (ROS). The human skin melanoma cells (SK-MEL-3) were cultured with various concentrations of hydrogen peroxide $(H_2O_2)$. The cell viability for $H_2O_2$-induced cytotoxicity or vanillic acid against $H_2O_2$ was measured by XTT assay in these cultures. For the effect of vanillic acid on the melanogenesis, the tyrosinase inhibitory activity was measured by colorimetric assay at a wavelength of 490 nm, and melanin synthesis activity were assessed after cells were cultured in the media with or without various cencentrations of vanillic acid. In this study, $H_2O_2$ decreased cell viability dose- and time-dependent manners and $XTT_{50}$ was determined at a concentration of 80 ${\mu}M$, $H_2O_2$. Vanillic acid increased the cell viability dose dependently in human skin melanoma cells damaged by $H_2O_2$-induced cytotoxicity. In the tyrosinase inhibitory activity, vanillic acid supresssed tyrosinase activity in dosedependent manner, and also decreased significantly melanin synthesis activity compared with $H_2O_2$-treated group. From these results. It is suggested that $H_2O_2$-mediated cytotoxicity was highly by the toxic criteria of Borenfreund and Puerner and also, vanillic acid has the protective effect on ROS-induced cytotoxicity and melanogenesis in these cultures.

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Effects of Phenolic Compounds in Milled Barley Grains on the Growth of Saccharomyces cerevisiae (보리쌀중의 Phenol 화합물이 Saccharomyces cerevisiae의 생육에 미치는 영향)

  • 정기택;김욱한;송형익
    • Korean Journal of Microbiology
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    • v.24 no.2
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    • pp.168-174
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    • 1986
  • The phenolic compounds contained in milled barley grains were seperated and identified by gas liquid chromatography and the effects of phenolic compounds extracted from milled barley grains and each authentic phenolic compound on the growth of Saccharomyces cerevisiae were studied. Severn phenolic acids, namely cinnamic, protocatechuic, ferulic, sinapid, vanillic, syringic, gallic acids, were identified in milled barley grains by gas liquid chromatography. The contents of sinapic, ferulic, cinnamic, protocatechuic acids were larger than those of vanillic and gallic acids. Phenolic compounds, extracted from milled barley grains and supplemented in culture broth, were inhibitory to the growth of Saccharomyces cerevisiae at levels above 100ppm to 24 hours but not inhibitory at all levels after 48 hours. Cinnamic, ferulic, vanillic acids at all levels were inhibitory to the growth of Saccharomyces cerevisiae, among them cinnamic acid was most inhibitory. Syringic acid was inhibitory to the growth of the yeast at the initial stage of culture. But sinapic and protocatechuic acids were slightly stimulatory to the growth of the yeast and gallic acid was ineffective to the growth of the yeast.

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Antimicrobial Effect of Organic Acid and Distribution of Vibrio parahaemolyticus from the Incheon Adjacent Sea (연안 해역에서 분리한 Vibrio parahaemolyticus에 대한 유기산의 증식억제 효과)

  • Jang, Jae-Seon;Kim, Yong-Hee;Yoon, Byoung-Jun
    • Journal of Environmental Health Sciences
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    • v.35 no.3
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    • pp.209-213
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    • 2009
  • This study was carried out to investigate the distribution of V. parahaemolyticus in Incheon adjacent sea, and anti-microbial effect on growth of V. parahaemolyticus in organic acid. The detected strains were compared for geography, months and sample types. V. parahaemolyticus was detected form 28.5 percent of 287 samples collected from Incheon area, and 34.7 percent of 91 samples collected in the months of July through September, and 24.7 percent of 279 shellfish samples respectively. The minimun inhibitory concentration(MIC) of organic acid in V. parahaemolyticus were 1,250ppm at propionic acid, citric acid and acetic acid, 2,500ppm at vanillic acid, respectively. MICs of combined treatment of acetic acid and vanillic acid, citric acid and vanillic acid, propionic acid and vanillic acid were 1,250 ppm. MICs of combined treatment of citric acid and acetic acid, propionic acid and acetic acid, propionic acid and citric acid was 12.5ppm. The antimicrobial effect of organic acid in V. parahaemolyticus was confirmed from the result of this experiment.