• 제목/요약/키워드: 2, 3-dihydroxybenzoic acid

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

  • 김성자;이형재;박근형;이종욱;임익재;정희종;문제학
    • 한국식품과학회지
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    • 제40권2호
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    • pp.129-134
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    • 2008
  • 복분자 와인은 복분자 열매를 발효ㆍ숙성시켜 제조하기 때문에 그들 양자 간의 성분에는 차이가 있을 것으로 추측되었다. 그러나 복분자 와인의 음용률이 높음에도 불구하고 복분자 와인 중에 함유된 성분들에 관한 체계적인 연구는 거의 전무한 실정이다. 그래서 먼저 복분자 와인 중에 함유되어 있는 성분들의 chemical profile의 검토를 위해 항산화 활성에 초점을 맞추어 화합물의 단리ㆍ구조해석에 착수하였다. 복분자 와인 11 L(신선 복분자 열매 15.7 kg 상당량)의 농축액(928.3 g)을 용매분획한 후 얻어진 EtOAc층(20 g/56.2 g)을 대상으로 각종 column chromatography 및 HPLC를 행하여 5종의 항산화 활성 화합물을 단리하였다. 그들을 대상으로 $^1H$-NMR 분석 및 TMS 유도체화 후 GCMS 분석을 행한 결과, 4-hydroxybenzoic acid(1, 0.1 mg), 3,4-dihydroxybenzoic acid(2, 0.3 mg), 4-(2-hydroxyethyl)-phenol(3, 0.6 mg), pyrocatechol(4, 0.3 mg), 3,4,5-trihydroxybenzoic acid ethyl ester(5, 0.6 mg)로 동정하였다. 화합물 1과 2는 복분자 열매중에 존재함이 보고되어 있으나 화합물 3-5는 복분자 열매로부터 그 존재가 보고되어진 바 없으며, 이들 5종의 화합물 모두가 복분자 와인으로부터 동정되어진 것 또한 처음이다.

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

  • 강희철;윤봉식;유승헌;유익동
    • 한국미생물·생명공학회지
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    • 제29권3호
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    • pp.149-154
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    • 2001
  • 버섯유래 저분자 대사산물을 탐색하던 중 대전근교에서 채집한 젖비단 그물버섯(Suillus granulatus)으로 부터 9종의 화합물을 분리하였다. 젖비단 그물버섯을 메탄올로 추출한 후 용매분획하여 그 중 대산산물이 많이 함유된 chloro-form 층 및 ethyl acetate층 에 대하여 각각 silica gel 및 Sephadx LH-20 column chromatography를 수행하였다. 주요대사산물을 함유하고 있는 분획물을 TLC및 분취용 HPLC를 사용하여 정제한 결과 9종의 화합물을 분리하였다. 분리된 화합물의 화학구조를 규명하기 위하여 NMR 및 mass 분석을 수행하여쓰며 그 결과 이들의 화합물은 4-hydro-xyphenylacetic acid, 4-hydroxybenzaldhyde, 2, 5-dihydro-xybenzoic acid methyl ester, 5-deoxy-5 methylthioadeno- sine. indole 3-carboxlic methyl ester indole-3-carbox-aldehyde 1,3,5-trihydroxy 7-methylanthraquinone nicotinamide, 3-geranylgeranyl-4-hydroxybenzoic acid로 동정하였다.

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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
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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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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연자육의 페놀성 성분 및 Tyrosinase 저해 활성 (Phenolic constituents of Nelumbinis Semen and Their Tyrosinase Inhibitory Activity)

  • 정지연;모은진;황방연;이미경
    • 생약학회지
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    • 제46권1호
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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.

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

  • 김상현;안종훈;정지연;김선범;조양희;황방연;이미경
    • 생약학회지
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    • 제44권3호
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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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    • 제10권5호
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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.

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

  • 차완식;조혜륜;정의창
    • 방사성폐기물학회지
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    • 제9권4호
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    • pp.207-217
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    • 2011
  • UV-Vis 분광광도법과 시간분해 레이저 유도 형광분광법(TRLFS)을 이용하여 흄산의 모사 리간드로 사용한 2,6-Dihydroxybenzoate(DHB)와 U(VI)의 착물형성반응을 조사하였다. U(VI)-DHB 착물 고유의 전하이동 흡수 스펙트럼을 분석한 결과, 착물형성반응은 우라늄-리간드 비가 1:1 또는 1:2 착물을 형성하는 이중 평형반응이며, 산도에 따라 착물종의 분포가 변한다는 것을 밝혔다. 계산된 착물형성상수 (log $K_1$ and log $K_2$)는 $12.4{\pm}0.1$$11.4{\pm}0.1$이다. 이에 더하여, TRLFS 방법으로 조사한 결과, DHB는 U(VI) 화학종들의 형광 소광제(quencher)로서 역할을 한다는 것을 확인하였다. 특히, 확인된 U(VI) 화학종 모두(${UO_2}^{2+}$, $(UO_2)_2{(OH)_2}^{2+}$$(UO_2)_3(OH)_5{^+})$에서 정적 (static) 및 동적 (dynamic) 소광작용이 공존하는 것으로 관찰되었다. 시간분해 형광 스펙트럼으로부터 리간드 농도에 따른 U(VI) 화학종의 형광세기와 형광수명을 측정하였으며, Stern-Volmer 식을 이용하여 분석하였다. 결정된 정적소광계수(KS)는 ${UO_2}^{2+}$, $(UO_2)_2{(OH)_2}^{2+}$$(UO_2)_3(OH)_5+$에 대하여 각각 $4.2{\pm}0.1$, $4.3{\pm}0.1$$4.34{\pm}0.08$이다. Stern-Volmer 식을 이용한 분석 결과, 단일 또는 이중 배위자 구조(mono- and bi-dentate)의 U(VI)-DHB 착물이 모두 정적소광효과에 관여하는 바닥상태 착물임을 확인하였다.

Peroxynitrite scavengers from Phellinus linteus

  • Jeong, Da-Mi;Jung, Hyun-Ah;Kang, Hye-Sook;Choi, Jae-Sue
    • Natural Product Sciences
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    • 제14권1호
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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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    • 제32권3호
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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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    • 제24권3호
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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.