• Title/Summary/Keyword: Protocatechuic acid

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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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The Preventive and Curative Effect of Cyanidin-3β-D-Glycoside and Its Metabolite Protocatechuic Acid Against TNBS-induced Colitis in Mice

  • Jang, Se-Eun;Choi, Jong-Ryul;Han, Myung Joo;Kim, Dong-Hyun
    • Natural Product Sciences
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    • v.22 no.4
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    • pp.282-286
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    • 2016
  • Cyanidin-$3{\beta}$-D-glycoside (C3G), which is widely distributed in herbal medicines and functional foods, exhibits anti-inflammatory, anti-oxidant, and anti-scratching behavioral effects. Orally administered C3G is metabolized to protocatechuic acid (PA) by gut microbiota. Therefore, we compared the anti-colitic effect of C3G to that of PA in mice with 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis. Orally administered C3G and PA preventively and curatively ameliorated TNBS-induced colitis parameters, including macroscopic colitis score, colon shortening, and increase of myeloperoxidase activity. Treatment with C3G or PA also inhibited the expression of cyclooxygenase-2, inducible NO synthatase, $IL-1{\beta}$, IL-6, and $TNF-{\alpha}$ and the activation of $NF-{\kappa}B$ in the colon of mice with TNBS-induced colitis. Furthermore, these also inhibited lipopolysaccharide-induced $NF-{\kappa}B$ activation and $TNF-{\alpha}$ expression in peritoneal macrophages. The anti-colitic effect of PA was more effective than C3G. Orally administered PA more potently attenuate colitis than C3G by inhibiting $NF-{\kappa}B$ activation and the anti-colitic efficacy of C3G may be dependent on the biotransformation of C3G to PA by gut microbiota.

Isolation and Identification of Inhibitory Compounds on Helicobacter pylori from Rosa multiflora Thunberg Fruit Extracts (Rosa multiflora Thunberg fruit 추출물로부터 Helicobacter pylori 억제물질의 분리 및 동정)

  • Park, Ki-Tae;Kim, Jin-Sung;Jo, Bun-Sung;An, Bong-Jeun;Chun, Sung-Sook;Kim, Jeung-Hoan;Cho, Young-Je
    • Journal of Life Science
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    • v.20 no.10
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    • pp.1511-1518
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    • 2010
  • The antimicrobial activity of 70% ethanol extracts from Rosa multiflora Thunberg fruit against Helicobacter pylori was examined. The inhibitory activity of Rosa multiflora Thunberg fruit extracts against H. pylori was determined to clear a zone of 14 mm with 70% ethanol extracts. Purification of inhibitory compounds was carried on Sephadex LH-20 and $C_{18}$ cartridge column chromatography using a gradient procedure, with increasing ethanol ($0{\rightarrow}100%$) in $H_2O$. The chemical structure of the purified inhibitory compounds on H. pylori was identified to be protocatechuic acid, chlorogenic acid and quercetin by FAB-MS, NMR and IR spectrum.

Monoamine Oxidase and Dopamine β-Hydroxylase Inhibitors from the Fruits of Gardenia jasminoides

  • Kim, Ji-Ho;Kim, Gun-Hee;Hwang, Keum-Hee
    • Biomolecules & Therapeutics
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    • v.20 no.2
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    • pp.214-219
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    • 2012
  • This research was designed to determine what components of Gardenia jasminoides play a major role in inhibiting the enzymes related antidepressant activity of this plant. In our previous research, the ethyl acetate fraction of G. jasminosides fruits inhibited the activities of both monoamine oxidase-A (MAO-A) and monoamine oxidase-B (MAO-B), and oral administration of the ethanolic extract slightly increased serotonin concentrations in the brain tissues of rats and decreased MAO-B activity. In addition, we found through in vitro screening test that the ethyl acetate fraction showed modest inhibitory activity on dopamine-${\beta}$ hydroxylase (DBH). The bioassay-guided fractionation led to the isolation of five bio-active compounds, protocatechuic acid (1), geniposide (2), 6'-O-trans-p-coumaroylgeniposide (3), 3,5-dihydroxy-1,7-bis(4-hydroxyphenyl) heptanes (4), and ursolic acid (5), from the ethyl acetate fraction of G. jasminoides fruits. The isolated compounds showed different inhibitory potentials against MAO-A, -B, and DBH. Protocatechuic acid showed potent inhibition against MAO-B ($IC_{50}$ $300{\mu}mol/L$) and DBH ($334{\mu}mol/L$), exhibiting weak MAO-A inhibition (2.41 mmol/L). Two iridoid glycosides, geniposide ($223{\mu}mol/L$) and 6'-O-trans-p-coumaroylgeniposide ($127{\mu}mol/L$), were selective MAO-B inhibitor. Especially, 6'-O-trans-p-coumaroylgeniposide exhibited more selective MAO-B inhibition than deprenyl, well-known MAO-B inhibitor for the treatment of early-stage Parkinson's disease. The inhibitory activity of 3,5-dihydroxy-1,7-bis (4-hydroxyphenyl) heptane was strong for MAO-B ($196{\mu}mol/L$), modest for MAO-A ($400{\mu}mol/L$), and weak for DBH ($941{\mu}mol/L$). Ursolic acid exhibited significant inhibition of DBH ($214{\mu}mol/L$), weak inhibition of MAO-B ($780{\mu}mol/L$), and no inhibition against MAO-A. Consequently, G. jasminoides fruits are considerable for development of biofunctional food materials for the combination treatment of depression and neurodegenerative disorders.

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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Characterization of Biological Treatment by an Isolated Phenol-Degrading Bacterium (페놀분해세균의 분리 및 생물학적 처리 특성)

  • 송형의;김진욱
    • Journal of Environmental Health Sciences
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    • v.24 no.3
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    • pp.54-62
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    • 1998
  • 20 bacterial strains capable of growing on phenol minimal medium were isolated from soil and wastewater by the enrichment culture technique, and among them, one isolate which was the best in the cell growth was selected and identified as Bacillus sp. SH3 by its characteristics. Strain SH3 could grow with phenol as the sole carbon source up to 15 mM, but did not grow in minimal medium containing above 20 mM of phenol. The optimal conditions of temperature and initial pH for growth and phenol degradation were 30$^{\circ}$C and 7.5, respectively. This strain could grow on various aromatic compounds such as catechol, protocatechuic acid, gentisic acid, o-, m-, p-cresol, benzoic acid, p-hydroxybenzoic acid, anthranilic acid, phenyl acetate and pentachlorophenol, and the growth-limiting log P value of strain SH3 on organic solvents was 3.1. In batch culture, strain SH3 degraded 97% of 10 mM phenol in 48 hours. In continuous culture under the conditions of 20 mM of influent phenol concentration and 0.050 hr$^{-1}$ of dilution rate, the treatment rate of phenol was 94%.

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Antioxidative Activity and Tyrosinase Inhibition Effect of Fractions from the Extract of Inonotus obliquus (차가버섯 용매별 분획물의 항산화 활성과 Tyrosinase 저해 활성)

  • Im, Do-Youn;Lee, Kyoung-In
    • Korean Journal of Pharmacognosy
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    • v.48 no.1
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    • pp.46-50
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    • 2017
  • This study was conducted to investigate the antioxidative activities and tyrosinase inhibition effects of fractions from the distilled water extract of Inonotus obliquus. Moreover, GC-MS based analysis with trimethylsilyl (TMS) derivatization was carried out for active compound in the extract of I. obliquus. In DPPH radical scavenging ability, $SC_{50}$ values of the ethyl acetate fraction was 0.393 mg/ml as a result of the most effective than other fractions. Meanwhile, aqueous fraction showed higher effect in tyrosinase inhibitoty activity. In GC-MS based analysis with TMS derivatization, 7 compounds including syringic acid, vanillic acid and protocatechuic acid were observed in ethyl acetate fraction, and oxalic acid is the main compound in aqueous fraction. As a result, it was confirmed that oxalic acid in aqueous fraction from the distilled water extract of I. obliquus was a compound showing tyrosinase inhibition effect.

Antioxidant Activity of Blackish Purple Rice

  • Ryu Su-Noh;Han Sang-Jun;Park Sun-Zik;Kim Hong-Reol
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.51 no.2
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    • pp.173-178
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    • 2006
  • Anthocyanin in blackish purple rice is composed of cyanidin, peonidin, malvidin, pelargonidin and delphinidin flavylium ion and their glucosides, which shows antioxidant activity similar to a-tocoperol. It has been demonstrated that cyanidin-3-glucoside(C3G) of anthocyanin has a high-potency antioxidant activity, and is a prominent in anticancer and antithrombotic activity. In analysis of content of anthocyanin from the genetic source of blackish purple rice, the level of C3G was approximately 80% of total contents of anthocyanins, and showed the highest content in Heugjinjubyeo, of which contains an amount of 500 mg by weight of 100g brown rice in comparison that most of varieties has less than 50mg by weight of 100g brown rice. We found that C3G pigment in blackish purple rice was considerably affected by cultural season, cultivation area, ripening temperature, and weather condition, etc. as well as genetic properties. In cross combination between Heugjinjubyeo and Suwon425, intermediate parent $F_9$ generation which was three times higher or more in C3G content than that of Heugjinjubyeo was bred, of which it contained an amount of 1678 mg by weight of 100g brown rice, and we called it 'C3GHi' Rice. And, we found that the C3GHi rice was more excellent than that of the existing Heugjinjubyeo in anticancer and antithrombotic activity. Methanol extract from Heugjinjubyeo was fractionated by organic solvents in order of n-hexane, $CH_{2}Cl_2$ and n-BuOH, and then oryzafuran, quercetin, vanillic acid and protocatechuic acid and their structures from the n-BuOH fraction were ascertained. Oryzafuran of these compounds was a natural compound found firstly in nature. Quercetin and protocatechuic acid besides new compound oryzafuran showed excellent antioxidant ability to vitamin C. These results suggest that blackish purple rice has very high value as a source of various functional food as well as staple food.

Ginsenoside, Phenolic Acid Composition and Physiological Significances of Fermented Ginseng Leaf (발효처리가 인삼잎의 진세노사이드 및 페놀산 조성 변화와 생리활성에 미치는 영향)

  • Lee, Ka-Soon;Seong, Bong-Jae;Kim, Gwan-Hou;Kim, Sun-Ick;Han, Seung-Ho;Kim, Hyun-Ho;Baik, Nam-Doo
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.39 no.8
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    • pp.1194-1200
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    • 2010
  • This study was carried out to investigate the compositional changes of ginsenosides and phenolic acids of ginseng leaf by fermentation in order to promote the utilization of ginseng leaf. The chief ginsenosides in non-fermented ginseng leaf (NFGL) were ginsenoside-Rg1 (26.0 mg/g), -Re (47.3 mg/g) and -Rd (23.9 mg/g). By fermentation, ginsenoside-Rg1, -Rb1, -Rb2, -Rb3, -Rc and -Re were decreased tremendously and new ginsenoside-Rh2, -Rh1, -Rg2 and -Rg3 appeared. Especially, ginsenoside-Rg3 (3.7 mg/g) on FGL was increased 15-fold compared to that of NFGL (0.2 mg/g). Total phenolic compound content of NFGL and FGL measured by colorimetric analysis was 350.4 and 312.5 mg%, respectively. There were 8 free and 6 ester forms of phenolic acids in NFGL. Among them, content of ferulic acid was the highest, comprised of 12.6 and 50.7 mg%, respectively. In FGL, total content of protocatechuic acid, p-hydroxybenzoic acid, and vanillic acid were increased by 28, 5 and 7.8 fold and ferulic acid was decreased greatly. Tyrosinase inhibitory activity of FGL was stronger than NFGL, while electron donating abilities of FGL were similar to NFGL.

Analysis of Useful Components for Freeze-Dried Persimmon Flower Powder by Cultivar (품종별 감꽃 동결건조 분말의 유효성분 분석)

  • Kim, Jun-Han;Park, Seok-Hee;Mun, Hye-Gyeong;Lee, In-Seon;Kim, Jong-Kuk
    • Food Science and Preservation
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    • v.13 no.6
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    • pp.691-696
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    • 2006
  • This study was carried out to analyze useful component in freeze-dried persimmon flower powder made from six cultivais. The cultivais were Dogunjosang, Kojongsi, Kabjubaeknok, Chalang, Weolhasi and SangjuDungsi. Powder of persimmon flower was prepared by milling after freeze drying at $-70^{\circ}C$. Crude lipid was the highest in Dogunjosang (57.26%). Major free sugars of the persimmon flowers were fructose ($95{\sim}310mg%$), glucose ($75{\sim}281mg%$) and sucrose ($7{\sim}28mg%$). Major organic acids were malic acid (225 mg% in Kabjubaeknok (Jun. 4th)) and tartaric acid (189 mg% in Kabjubaeknok (Jun. 4th)). Predominant free amino acids were hydroxy-L-proline(25.33 mg% in Weolhasi), L-citrulline (58.83 mg% in SangjuDungsi (May 280)) and L-threonine (11.88 mg% in SangjuDungsi (May 280)). Major phenolic compounds in the persimmon flowers were caffeic acid ($1,946{\mu}g/100 g$ in Kabjubaeknok (Jun. 4th)), p-hydioxybenzoic acid($418{\mu}g/100 g$ in SangjuDungsi (May 29th)) and protocatechuic acid($181{\mu}g/100 g$ in Kabjubaeknok(Jun. 1st)). The results suggest that persimmon flowers be potential materials as useful food ingredients.