• Title/Summary/Keyword: 3.4-dihydroxybenzoic acid

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Peroxynitrite scavengers from Phellinus linteus

  • Jeong, Da-Mi;Jung, Hyun-Ah;Kang, Hye-Sook;Choi, Jae-Sue
    • Natural Product Sciences
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    • v.14 no.1
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    • pp.1-11
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    • 2008
  • Peroxynitrite ($(ONOO^-)$ is a cytotoxic species formed from nitric oxide and superoxide anion, which are highly implicated in the pathogenesis of oxidative stress-mediated diseases. The aim of this study was to investigate the scavenging effects of Phellinus linteus on authentic $ONOO^-$, and further phytochemical studies are planned that will attempt to identify the active principles. From the active EtOAc fraction, a mixture of fungisterol and 5-dihydroergosterol (1), a mixture of betulin and 1,2-benzenedicarboxylic acid bis (2-methyl heptyl) ester (2), protocatechualdehyde (3), protocatechuic acid (4), cirsiumaldehyde (5), hispidin (6), caffeic acid (7), phelligridin D (8), uracil (9), gallic acid (10), 2,5-dihydroxybenzoic acid (11), ferulic acid (12), 2,3-dihydroxybenzaldehyde (13), arbutin (14), isoferulic acid (15), guanosine (16), and ellagic acid (17) were isolated, and their structures were characterized based on spectroscopic data. All compounds except 3, 6, 7 and 16 were isolated for the first time from P. linteus. Compounds 3, 4, 6-8, 10-15, and 17 showed potent scavenging activity on $ONOO^-$, with $IC_{50}$ values of $2.06\;{\pm}\;0.10$, $3.45\;{\pm}\;0.57$, $0.71\;{\pm}\;0.05$, $2.78\;{\pm}\;0.36$, $5.42\;{\pm}\;0.26$, $1.13\;{\pm}\;0.02$, $1.82\;{\pm}\;0.17$, $0.91\;{\pm}\;0.19$, $1.59\;{\pm}\;0.09$, $1.88\;{\pm}\;0.07$, $1.22\;{\pm}\;0.37$, and $2.01\;{\pm}\;0.02\;{\mu}M$, respectively, as compared to the positive control, DL-penicillamine, with an $IC_{50}$ value of $5.04\;{\pm}\;0.06\;{\mu}M$.

Amperometric Detection of Some Catechol Derivatives and o-aminophenol Derivative with Laccase Immobilized Electrode: Effect of Substrate Structure

  • Quan De;Shin Woonsup
    • Journal of the Korean Electrochemical Society
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    • v.7 no.2
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    • pp.83-88
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    • 2004
  • [ $DeniLite^{TM}$ ] laccase immobilized Pt electrode was used for amperometric detection of some catechol derivatives and o-aminophenol (OAP) derivative by means of substrate recycling. In case of catechol derivatives, the obtained sensitivities are 85, 79 and $57 nA/{\mu}M$ with linear ranges of $0.6\~30,\;0.6\~30\;and\; 1\~25 {\mu}M$ and detection limits (S/N=3) of 0.2, 0.2 and $0.3{\mu}M$ for 3,4-dihydroxycinnaminic acid (3,4-DHCA), 3,4-dihydroxybenzoic acid (3,4-DHBA) and 3,4-dihydroxyphenylacetic acid (3,4-DHPAA), respectively. In case of OAP derivative, the obtained sensitivity is $237 nA/{\mu}M$ with linear range of $0.2\~15{\mu}M$ and detection limit of 70 nM for 2-amino-4-chlorophenol (2-A-4-CP). The response time $(t_{90\%})$ is about 2 seconds for each substrate and the long-term stability is around 40-50days for catechol derivatives and 30 days for 2-A-4-CP with retaining $80\%$ of initial activity. The optimal pHs of the sensor for these substrates are in the range of 4.5-5.0, which indicates that stability of the enzymatically oxidized product plays a very important role in substrate recycling. The different sensitivity of the sensor for each substrate can be explained by the electronic effect of the sugstituent on the enzymatically oxidized form.

Antifungal Activity of Eucalyptus-Derived Phenolics Against Postharvest Pathogens of Kiwifruits

  • Oh, Soon-Ok;Kim, Jung-A;Jeon, Hae-Sook;Park, Jong-Cheol;Koh, Young-Jin;Hur, Hyun;Hur, Jae-Seoun
    • The Plant Pathology Journal
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    • v.24 no.3
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    • pp.322-327
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    • 2008
  • Antifungal activities of natural substrances from Eucalyptus darlympleana, E. globules, E. gunnii and E. unigera were evaluated against postharvest pathogens of kiwifruits, Botrytis cinerea, Botryosphaeria dothidea, and Diaporthe actinidiae, to screen effective natural substances as an alternative to chemical fungicides. Methanol extract of the Eucalyptus trees showed strong antagonistic activity against the pathogenic fungi. Among them, E. unigera and E. darlympleana effectively inhibited mycelial growth of the pathogens. For chemical identification of the antifungal substances, the methanol extract of E. darlympleana leaves was successively partitioned with $CH_2Cl_2$, EtOAc, n-BuOH and $H_2O$. Among the fractions, $CH_2Cl_2$ and n-BuOH showed strong inhibitory activity of mycelial growth of the fungi. Five compounds were isolated from EtOAc and n-BuOH fractions subjected to $SiO_2$ column chromatography. Two phenolic compounds(gallic acid and 3,4-dihydroxybenzoic acid) and three flavonoid compounds(quercetin, quercetin-3-O-$\alpha$-L-rhamnoside, quercetin-3-O-$\beta$-glucoside) were identified by $^1H$-NMR and $^{13}C$-NMR spectroscopy. Among them, only gallic acid was found to be effective in mycelial growth and spore germination of B. cinerea at relatively high concentrations. The results suggest that gallic acid can be a safer and more acceptable alternative to current synthetic fungicides controlling soft rot decay of kiwifruit during postharvest storage.

Phenolic Compounds from the Twigs of Corylopsis coreana Uyeki and Their Cytotoxic Activity (히어리나무의 페놀성 화합물 및 세포독성활성)

  • Kwon, Oh Kil;Kim, Chung Sub;Suh, Won Se;Park, Kyoung Jin;Cha, Joon Min;Choi, Sang Un;Kwon, Hak Cheol;Lee, Kang Ro
    • Korean Journal of Pharmacognosy
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    • v.47 no.1
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    • pp.1-6
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    • 2016
  • Phytochemical investigation of the twigs of Corylopsis coreana afforded 10 phenolic compounds, bergenin (1), 6'-O-galloylbergenin (2), 3'-O-galloylbergenin (3), (-)-catechin (4), (-)-epicatechin (5), (-)-epicatechin-3-O-galloyl ester (6), 4-methoxy-3,-5-dihydroxybenzoic acid (7), gallic acid (8), 2,4,6-trimethoxyphenol-1-O-${\beta}-\small{D}$-glucopyranoside (9), and 2,4,6-trimethoxyphenol-1-O-${\beta}-\small{D}$-(6-O-galloyl)-glucopyranoside (10). Their structures were characterized by spectroscopic data and identified by comparing these data with those in the literatures. The compounds 3, 9 and 10 were isolated for the first time from this source. All the isolates (1-10) were tested for their cytotoxic activity against A549, SK-OV-3, SK-MEL-2, and HCT15 cell lines in vitro using the SRB bioassay. The compounds 5, 7 and 8 exhibited selective cytotoxic activity against SK-MEL-2 cell line.

Isolation and Identification of Low Molecular Volatile Compounds from Ethyl Acetate Layer of Korean Black Raspberry (Rubus coreanus Miq.) Wine (복분자(Rubus coreanus Miquel) 와인의 ethyl acetate 획분으로부터 저분자 휘발성 화합물들의 분리 및 구조해석)

  • Cho, Jeong-Yong;Kim, Seong-Ja;Lee, Hyoung-Jae;Kim, Jin-Young;Lym, Ik-Jae;Kang, Seong-Koo;Park, Keun-Hyung;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.43 no.5
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    • pp.558-563
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    • 2011
  • In the course of our investigation for chemical constituents in the ethyl acetate layer of Korean black raspberry wine, five compounds were isolated and purified by silica gel column chromatography and high-performance liquid chromatography. The isolated compounds were identified as ethyl succinate (1), vanillic acid (2), ethyl 3,4-dihydroxybenzoate (3), furan-2-ol (4), and 4-(4-hydroxyphenyl)butan-2(S)-ol (5) based on the spectroscopic data of electrospray ionization tandem mass spectrometry and nuclear magnetic resonance. The presence of 2 in Korean black raspberry has previously reported. However, 1 and 3-5 in Korean black raspberry and its wine were isolated for the first time.

Comparison of Phenolic Acid from Shoots of Aralia elata and Kalopanax pictus Cultivated in Korea Using UPLC-DAD-ESI(+)-QToF/MS (UPLC-DAD-ESI(+)-QToF/MS를 이용한 국내산 두릅나무 및 음나무 순 내 페놀산 특성 비교)

  • Kim, Young Jin;Kim, Heon-Woong;Lee, Min-Ki;Lee, Seon-Hye;Asamenew, Gelila;Lee, Suji;Lee, Sang Hoon;Cha, Youn-Soo;Kim, Jung Bong
    • Korean Journal of Environmental Agriculture
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    • v.37 no.4
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    • pp.260-267
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    • 2018
  • BACKGROUND: In this study, shoots of Aralia elata and Kalopanax pictus which belong to the Araliaceae family were analyzed using UPLC-DAD-ESI(+)-QToF/MS to characterize of individual phenolic acids. METHODS AND RESULTS: Total thirteen phenolic acids were identified, and nine hydroxycinnamic acid derivatives have been identified for the first time in shoots of Aralia elata and Kalopanax pictus. For total phenolic acid content (mg/100g dry weight), shoots of Aralia elata and Kalopanax pictus showed 754.8 and 845.3 mg/100g, respectively. 5-O-Caffeoylquinic acid (49%) and 3,5-di-O-caffeoylquinic acid (44%) were found as major phenolic acids in Aralia elata, while 5-O-caffeoylquinic acid (91%) was a major component in Kalopanax pictus. CONCLUSION: On comparing the two plants, it was considered that the biosynthesis of 3,5-di-O-caffeoylquinic acid can be affected by 5-O-caffeoylquinic acid in Aralia elata.

Focused Electrospray Deposition for Matrix-assisted Laser Desorption/Ionization Mass Spectrometry

  • Jeong, Kyung-Hwan;Seo, Jong-Cheol;Yoon, Hye-Joo;Shin, Seung-Koo
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2293-2298
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    • 2010
  • Focused electrospray (FES) deposition method is presented for matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. FES ion optics consists of two cylindrical focusing electrodes capped with a truncated conical electrode through which an electrospray emitter passes along the cylindrical axis. A spray of charged droplets is focused onto a sample well on a MALDI target plate under atmospheric pressure. The shape and size distributions of matrix crystals are visualized by scanning electron microscope and the mass spectra are obtained by time-of-flight mass spectrometry. Angiotensin II, bradykinin, and substance P are used as test samples, while $\alpha$-cyano-4-hydroxycinnamic acid and dihydroxybenzoic acid are employed as matrices. FES of a sample/matrix mixture produces fine crystal grains on a 1-3 mm spot and reproducibly yields the mass spectra with little shot-to-shot and spot-to-spot variations. Although FES greatly stabilizes the signals, the space charge due to matrix ions limits the detection sensitivity of peptides. To avoid the space charge problem, we adopted a dual FES/FES mode, which separately deposits matrix and sample by FES in sequence. The dual FES/FES mode reaches the detection sensitivity of 0.88 amol, enabling ultrasensitive of peptides by homogeneously depositing matrix and sample under atmospheric pressure.