• Title/Summary/Keyword: 2,3-dihydroxybenzoic acid

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Isolation and Identification of Low Molecular Phenolic Antioxidants from Ethylacetate Layer of Korean Black Raspberry (Rubus coreanus Miquel) Wine (복분자(Rubus coreanus Miquel) 와인의 에틸아세테이트층으로부터 저분자 페놀성 항산화 화합물의 단리·동정)

  • Kim, Seong-Ja;Lee, Hyoung-Jae;Park, Keun-Hyung;Rhee, Chong-Ouk;Lim, Ik-Jae;Chung, Hee-Jong;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.40 no.2
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    • pp.129-134
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    • 2008
  • Five antioxidative active substances were isolated from the EtOAc layer (20 g/56.2 g) of Korean black raspberry (Rubus coreanus Miquel) wine (11 L, black raspberry 15.7 kg fresh wt. eq.) by various column chromatography and high performance liquid chromatography (HPLC). Proton nuclear magnetic resonance ($^1H$-NMR) spectroscopy and gas chromatography Electro Ionization-Mass Spectrometry (GC-EI-MS) identified these as 4-hydroxybenzoic acid (1, 0.1 mg), 3,4-dihydroxybenzoic acid (2, 0.3 mg), 4-(2-hydroxyethyl)-phenol (3, 0.6 mg; tyrosol), pyrocatechol (4, 0.3 mg), 3,4,5-trihydroxybenzoic acid ethyl ester (5, 0.6 mg; ethyl gallate). The presence of 1 and 2 in Korean black raspberry has previously been reported. However, the presence of 3-5 in Korean black raspberry, and the identification of 1-5 from the Korean black raspberry wine have never before been reported.

Chemical Structures of Compounds Isolated from Mushroom Suillus granulatus (젖비단 그물버섯(Suillus granulatus)으로부터 분리한 저분자 화합물)

  • 강희철;윤봉식;유승헌;유익동
    • Microbiology and Biotechnology Letters
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    • v.29 no.3
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    • pp.149-154
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    • 2001
  • We have investigated the secondary metabolites from the mushroom Suillus granulatus. The methanolic extract of fruit body was separated by silica gel and Sephadex LH-20 column chromatographies. TLC and HPLC were also used for the further purification on compounds from the extracts, Nine compounds were finally isolated and their structures were assigned as 4-hydroxyphenylacetic acid 4-hydroxybenzaldehyde 2,5-dihydroxybenzoic acid methyl ester 5'-deoxy-5'methylthioadenosine. indole-3- carboxlic acid methyl ester indole 3-carboxaldehyde 1,3,5-trihydroxy 7-methylanthraquinone nicotinamide and 3-geranylgeranyl-4-hydroxybenzoic acid on the basis of NMR studies.

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Aldose Reductase Inhibitory Constituents from Ganoderma applanatum

  • Shim, Sang-Hee;Ryu, Ji-Young;Kim, Ju-Sun;Kang, Sam-Sik;Chung, Sang-Hun;Lee, Yeon-Sil;Lee, Sang-Hyun;Shin, Kuk-Hyun
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.261.1-261.1
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    • 2003
  • The EtOAc and CH$_2$Cl$_2$ soluble fractions from the fruit body of Ganoderma applanatum showed strong aldose reductase inhibitory activity. Nine compounds were isolated from both fractions. They were identified by spectral data as D-mannitol (1), 2-methoxyfatty acid (2), cerebrosides [(2S,3R,4E,8E)-1-O-${\beta}$-D-glucopyranosyl-3-hydroxy-2-[(R)-2'-hydroxypalmitoyl]amino-9-methyl-4,8-octadecadiene] (3), daucosterol (4), 2,5-dihydroxybenzoic acid (5), protocatechualdehyde (6), 5-dihydroergosterol (7), ergosterol peroxide (8), and cerevisterol (9). (omitted)

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Phenolic constituents of Nelumbinis Semen and Their Tyrosinase Inhibitory Activity (연자육의 페놀성 성분 및 Tyrosinase 저해 활성)

  • Jeong, Ji Yeon;Mo, Eun Jin;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Korean Journal of Pharmacognosy
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    • v.46 no.1
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    • pp.1-5
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    • 2015
  • In the course of screening tyrosinase inhibitory activity, EtOAc-soluble fraction of Nelumbinis Semen (Seeds of Nelumbo nucifera) showed significant inhibition. Further fractionation of the EtOAc-soluble fraction resulted in 12 compounds, which were identified as 4-(hydroxymethyl)phenol (1), tyrosol (2), 4-(hydroxymethyl)benzaldehyde (3), 4-hydroxybenzoic acid (4), 4-(2-methoxyvinyl)benzene-1,2-diol (5), 2,6-dihydroxybenzoic acid (6), (2R-trans)-2,3-dihydro-3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (7), (+)-catechin (8), elephantorrhizol (9), (+)-dehydrovomifoliol (10), (-)-boscialin (11) and uridine (12). Compounds 5 and 7 were first reported from this plant. Among the isolated compounds, compound 7 showed strong inhibition on tyrosinase activity with mixed mechanism of competitive and noncompetitive inhibition.

Tyrosinase Inhibitory Phenolic Constituents of Smilax china Leaves (청미래덩굴 잎의 페놀성 성분 및 Tyrosinase 저해 활성)

  • Kim, Sang Hyun;Ahn, Jong Hoon;Jeong, Ji Yeon;Kim, Seon Beom;Jo, Yang Hee;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Korean Journal of Pharmacognosy
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    • v.44 no.3
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    • pp.220-223
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    • 2013
  • In the course of screening tyrosinase inhibitory activity, total methanolic extract and EtOAc-soluble fraction of Smilax china leaves showed significant inhibitory activity. Further fractionation and isolation of the EtOAc-soluble fraction resulted in 12 phenolic compounds, which were identified as 4-hydroxybenzoic acid (1), 3,4-dihydroxybenzaldehyde (2), 3,4-dihydroxybenzoic acid (3), 3,4-dihydroxyacetophenone (4), 3-hydroxy-4-methoxy benzoic acid (5), trans-p-hydroxycinnamic acid (6), cis-p-hydroxycinnamic acid (7), trans-resveratrol (8), cis-resveratrol (9), dihydroresveratrol (10), moracin M (11) and kaempferol (12). Compounds 1-11 were first reported from this plant. Among the isolated compounds, compounds 2, 8, 9 and 12 showed strong inhibition on tyrosinase activity.

Inhibitory Effects of Methanol Extract, Phenolic Acids and Flavonoids from the Leaves of Eucalyptus darylmpleana against 1,1-Diphenyl-2-picrylhydrazyl Radical

  • Park, Jong-Cheol;Park, Ju-Gwon;Hur, Jae-Seoun;Choi, Myeong-Rak;Yoo, Eun-Jeong;Kim, Sung-Hwan;Son, Jin-Chang;Kim, Moon-Sung
    • Natural Product Sciences
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    • v.10 no.5
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    • pp.244-247
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    • 2004
  • The inhibitory effects of the leaves of Eucalyptus darylmpleana (Myrtaceae) on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical was examined. The scavenging effect of the ethyl acetate fraction of Eucalyptus darylmpleana leaves on DPPH radical was stronger than the other fractions, and further purified by silica gel and Sephadex LH-20 column chromatography. 3,4-Dihydroxybenzoic acid, gallic acid, quercetin, quercetin $3-O-{\alpha}-_L-rhamnoside$, quercetin $3-O-{\beta}-_D-glucoside$ and quercetin 3-O-rutinoside were isolated and elucidated by spectroscopic data. Among these components, gallic acid and quercetin $3-O-{\alpha}-_L-rhamnoside$ exhibited potent scavenging activities on DPPH radical with $IC_{50}$ values of 6.02 and $5.54\;{\mu}M$, respectively.

Spectroscopic Studies on U(VI) Complex with 2,6-Dihydroxybenzoic acid as a Model Ligand of Humic Acid (분광학을 이용한 흄산의 모델 리간드인 2,6-Dihydroxybenzoic acid와 우라늄(VI)의 착물형성 반응에 관한 연구)

  • Cha, Wan-Sik;Cho, Hye-Ryun;Jung, Euo-Chang
    • Journal of Nuclear Fuel Cycle and Waste Technology(JNFCWT)
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    • v.9 no.4
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    • pp.207-217
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    • 2011
  • In this study the complex formation reactions between uranium(VI) and 2,6-dihydroxybenzoate (DHB) as a model ligand of humic acid were investigated by using UV-Vis spectrophotometry and time-resolved laser-induced fluorescence spectroscopy (TRLFS). The analysis of the spectrophotometric data, i.e., absorbance changes at the characteristic charge-transfer bands of the U(VI)-DHB complex, indicates that both 1:1 and 1:2 (U(VI):DHB) complexes occur as a result of dual equilibria and their distribution varies in a pH-dependent manner. The stepwise stability constants determined (log $K_1$ and log $K_2$) are $12.4{\pm}0.1$ and $11.4{\pm}0.1$. Further, the TRLFS study shows that DHB plays a role as a fluorescence quencher of U(VI) species. The presence of both a dynamic and static quenching process was identified for all U(VI) species examined, i.e., ${UO_2}^{2+}$, $(UO_2)_2{(OH)_2}^{2+}$, and $(UO_2)_3{(OH)_5}^+$. The fluorescence intensity and lifetimes of each species were measured from the time-resolved spectra at various ligand concentrations, and then analyzed based on Stern-Volmer equations. The static quenching constants (log $K_s$) obtained are $4.2{\pm}0.1$, $4.3{\pm}0.1$, and $4.34{\pm}0.08$ for ${UO_2}^{2+}$, $(UO_2)_2{(OH)_2}^{2+}$, and $(UO_2)_3{(OH)_5}^+$, respectively. The results of Stern-Volmer analysis suggest that both mono- and bi-dentate U(VI)-DHB complexes serve as groundstate complexes inducing static quenching.

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 $5.04\;{\pm}\;0.06\;{\mu}M$.

Detection of Long Alkyl Esters of Succinic and Maleic Acid Using TLC-MALDI-MS

  • Kim, Hin-Hee;Han, Sang-Pil;Kim, Jeong-Kwon;Kim, Yeong-Joon
    • Bulletin of the Korean Chemical Society
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    • v.32 no.3
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    • pp.915-920
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    • 2011
  • Four esters of succinic and maleic acid were synthesized, separated by thin-layer chromatography (TLC), and identified using matrix-assisted laser desorption/ionization-mass spectrometry (MALDI-MS). A comparison of matrix materials showed that 2,6-dihydroxybenzoic acid (2,6-DHB) yielded a greater ionization efficiency than 2,5-DHB prior to TLC separation. The location of each ester sample on the TLC plate was estimated by comparing the developed plate with a duplicate plate that had been visualized by immersion in a $KMnO_4$ solution. Generally, mass spectra obtained from the $KMnO_4$-visualized plate were relatively poor. Reproducible mass spectra with high peak abundance were difficult to obtain using the 2,6-DHB matrix from crude synthetic esters extracted from the TLC plates. Significant improvements in both reproducibility and sensitivity were realized by using pencil lead as the MALDI matrix. The current methodology will be beneficial to organic chemists since it can provide a guideline for simple and rapid characterization of small organic compounds.

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.