• Title/Summary/Keyword: 3,4-dihydroxybenzaldehyde

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Quantification of the 25 Components in Onkyung-Tang by Ultra Performance Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry (UPLC-ESI-MS/MS를 이용한 온경탕 중 25종 성분의 함량분석)

  • Seo, Chang-Seob;Shin, Hyeun-Kyoo
    • Korean Journal of Pharmacognosy
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    • v.47 no.1
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    • pp.92-101
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    • 2016
  • In this study, an ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS/MS) method was established for simultaneous determination of the 25 marker components, including chlorogenic acid, gallic acid, oxypaeoniflorin, homogentisic acid, methyl gallate, caffeic acid, 3,4-dihydroxybenzaldehyde, paeoniflorin, albiflorin, liquiritin, nodakenin, ferulic acid, ginsenoside Rg1, liquiritigenin, coumarin, cinnamic acid, benzoylpaeoniflorin, ginsenoside Rb1, cinnamaldehyde, paeonol, glycyrrhizin, 6-gingerol, evodiamine, rutecarpine, and spicatoside A in traditional Korean formula, Onkyung-tang. All analytes were separated on a Waters Acquity UPLC BEH $C_{18}$ analytical column ($2.1{\times}100mm$, $1.7{\mu}m$) at $45^{\circ}C$ using a mobile phase of 0.1% (v/v) formic acid in water and acetonitrile with gradient elution. The MS analysis was carried out using a Waters ACQUITY TQD LC-MS/MS coupled with an electrospray ionization (ESI) source in the positive and negative modes. The flow rate and injection volume were 0.3 mL/min and $2.0{\mu}L$, respectively. The correlation coefficient of all analytes in the test ranges was greater than 0.98. The limits of detection and quantification values of the 25 marker compounds were in the ranges 0.03-19.43 and 0.09-58.29 ng/mL, respectively. As a result, methyl gallate, 3,4-dihydroxybenzaldehyde, evodiamine, and rutecarpine were not detected in this sample and the concentrations of the 21 compounds except for the above 4 compounds were $33.09-3,496.32{\mu}g/g$ in Onkyung-tang decoction. Among these compounds, paeonol was detected at the highest amount as a $3,496.32{\mu}g/g$.

Phenolic Compounds from Caesalpinia sappan and Their Inhibitory Effects on LPS-induced NO Production in RAW264.7 Cells

  • Min, Byung Sun;Cuong, To Dao
    • Natural Product Sciences
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    • v.19 no.3
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    • pp.201-205
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    • 2013
  • Thirteen phenolic compounds, 1,4-dimethoxybenzene (1), 3,4-dihydroxybenzaldehyde (2), (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acrylaldehyde (3), 3,7-dihydroxy-4H-chromen-4-one (4), 2,3-dihydroxy-1-(3,4-dihydroxyphenyl)propan-1-one (5), 4-hydroxy-3-methoxybenzoic acid (6), 4-hydroxy-3,5-dimethoxybenzoic acid (7), methyl 3,4-dihydroxybenzoate (8), 4-hydroxy-3,5-dimethoxybenzaldehyde (9), 3,4-dihydroxybenzoic acid (10), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (11), 2,4,6-trihydroxybenzaldehyde (12) and benzene-1,2,4-triol (13) were isolated from the heartwood of Caesalpinia sappan. Their anti-inflammatory activity was evaluated against LPS-induced NO production in macrophage RAW264.7 cells. Among them, compounds 3 and 8 showed strong inhibitory activities toward the LPS-induced NO production in macrophage RAW264.7 cells with $IC_{50}$ values of 14.5 and 21.5 ${\mu}M$, respectively.

Determination of Trace Germanium by Anodic Stripping Polarography (Anodic Stripping Polarograph에 의한 극미량 게르마늄의 분석(II))

  • Choi, Won-Hyung;Lee, Jong-Moo
    • Analytical Science and Technology
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    • v.5 no.1
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    • pp.17-24
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    • 1992
  • Germanium(IV) was determinated in perchloric acid supporting electrolyte solution containing catechol derivates 3.4-dihydroxy benzoic acid, 3.4-dihydroxy benzaldehyde, adrenaline by hanging mercury electrode(HMDE) of anodic stripping polarography. And then to apply this experimental method for determination of germanium(IV) in natural samples. Germanium(IV) was determinated $300{\mu}g/L$ in ginseng and $210{\mu}g/L$ in mineral water.

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Syntheses Bis or Tri Crown Ethers Containing Imine Group(V) (이민기를 포함하는 비스 또는 트리 크라운에테르의 합성 (V))

  • Chang, Seung-Hyun;Kim, Jung-Sung
    • Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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    • 2003.08a
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    • pp.110-113
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    • 2003
  • We report herein synthetic results obtained six new types of bis-benzocrown ethers containing imine group. Bis crown ethers l~3 are aminobenzo-15-crown-5-ether linked with terephthalaldehyde, isophthalaldehyde, phthaldehyde respectively by imine reaction. Bis crown ethers l~3 are different distances in each crown ether rings. Bis crown ether 4 has large cavity in crown ethers. Functionalized crown ether 5 is synthesized amonobenzo-l5-crown-5-ether and terephthaladehyde same ratio at one to one. Bis crown ether 6 has phothosensitive linkage between crown ethers. Bis crown ether 7 is prepared by amonobenzo-l5-crown-5-ether and triethyl ortho formate. 4'-Nitrobenzo-crown ethers and 3',4'-dinitrobenzo-crown ethers were prepared by nitration of benzo crown ethers, obtained from the reaction of catechol and oligoethylene glycol ditosylate. Crown ethers containing aldehyde group were synthesized from the reaction of 3,4-dihydroxybenzaldehyde and corresponding ditosylate respectively. The synthesized crown ethers were characterized respectively by IR, NMR. GC-Mass.

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Sedative Effects of Combined Administration of 4-Hydroxy-3-methoxybenzaldehyde, a Component of Gastrodia elata, and 2,3-Dihydroxybenzaldehyde in Rats (천마성분인 4-hydroxy-3-methoxybenzaldehyde와 2,3-dihydroxy-benzaldehyde의 병용투여에 의한 진정효과)

  • Lee, Dong-Ung;Choi, Hyung-Chul;Lee, Kwang-Youn;Lee, Soo-Kwan;Kim, Jung-Ae;Yong, Chul-Soon;Kim, Jin-Sook;Huh, Geun;Shin, Son-Moon;Koo, Byung-Soo;Ha, Jeoung-Hee
    • Journal of Life Science
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    • v.16 no.7 s.80
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    • pp.1214-1218
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    • 2006
  • The present study was performed to investigate the sedative effects of the combined administration of phenolic compounds. 4-hydroxy-3-methoxybenzaldehyde, a component of Gastrodia elnta, showing positive GABAergic neuromodulation was administered intraperitoneally together with an identical dose of 2,3-dihydroxybenzaldehyde, a potent antioxidant, to the rats and then evaluated for its effects on the convulsion, the hypnosis, the inxiety and the muscle relaxation. Combined administration of both compounds significantly reduced the pentyleneterazole-induced lethality. In addition, this mixture significantly enhanced the pentobarbital-induced sleeping time. Contrary to the anticonvulsive and sedative effects, the combined administration did not exhibit anxiolytic or muscle relaxant activities. These results indicated that the combined treatment of 2,3-dihydroxybenzaldehtyde and 4-hydroxy-3-methoxybenzaldehyde with different effects leads to the anticonvulsion and/or sedation

Synthesis of New Crown Ethers Containing Benzothiazole Group (벤조티아졸기를 갖는 새로운 크라운 에테르의 합성)

  • Chang, Seung-Hyun;Yeon, Ae-Sook;Chung, Kwang-Bo
    • Journal of the Korean Chemical Society
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    • v.40 no.2
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    • pp.117-121
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    • 1996
  • Two new crown ethers containing nitrogen and sulfur atoms adjacent to the crown rings were prepared. 4'-Benzothiazolylbenzo-12-crown-4 (1) or 4'-benzothiazolylbenzo-15-crown-5 (2) were synthesized by reaction of 2-aminothiophenol with 4'-formylbenzo-12-crown-4 (3) or 4'-formylbenzo-15-crown-5 (4) respectively. (3) and (4) were obtained by reaction of 3, 4-dihydroxybenzaldehyde with tri- or tetraethyleneglycol ditosylate. Triethyleneglycol ditosylate or tetraethyleneglycol ditosylate were synthesized by reaction of p-toluenesulfonylchloride with triethyleneglycol or tetraethyleneglycol in the presence of sodium hydroxide.

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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.

Antioxidative Activities of Phenolic Compounds Isolated from Inonotus obliquus (차가버섯으로부터 분리한 페놀성 화합물의 항산화효과)

  • Kim, Hyoung-Ja;Jin, Chang-Bae;Lee, Yong-Sup
    • Korean Journal of Pharmacognosy
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    • v.38 no.2 s.149
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    • pp.164-169
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    • 2007
  • ln our continued search for biologically active compounds from traditional medicine, we found that ethyl acetate fraction from Inonotus obliquus showed potent antioxidant activities on three different cell-free bioassay systems. Bioassay-directed chromatographic fractionation of the ethyl acetate fraction from Inonotus obliquus afforded four phenolic compounds, 4-(3,4-dihydroxyphenyl)-(E)-3-buten-2-one (1) , 3,4-dihydroxybenzaldehyde (2), protocatechuic acid (3) and caffeic acid (4) along with three sterols such as lanosterol (5), ergosterol peroxide (6) and 9,11-dehydroergosterol peroxide (7). Among isolates, phenolic compounds (1-4) were assessed for antioxidant activities. Almost phenolic compounds showed potent DPPH and superoxide anion radicals scavenging and lipid peroxidation inhibitory activities indicating that these phenolic compounds contribute to the antioxidative activities of I. obliquus. Compounds 2-3 and 7 were isolated for the first time from this plant.

Syntheses New Bis-Crown Ethers Containing Imine Group(III) (새로운 이민기를 포함하는 비스 크라운 에테르의 합성)

  • Lee, Sang-Hwoon;Jang, Dong-Chun;Chang, Seung-hyun
    • Journal of the Korean Society of Industry Convergence
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    • v.6 no.1
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    • pp.73-80
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    • 2003
  • We report herein synthetic results obtained six new types of bis-benzocrown ethers containing imine group. Bis crown ethers1~3 are aminobenzo-15-crown-5-ether linked with terephthalaldehyde, isophthalaldehyde, phthaldehyde respectively by imine reaction. Bis crown ethers1~3 are different distances in each crown ether rings. Bis crown ether 4 has large cavity in crown ethers. Functionalized crown ether 5 is synthesized amonobenzo-15-crown-5-ether and terephthaladehyde same ratio at one to one. Bis crown ether 6 has photosensitive linkage between crown ethers. Bis crown ether 7 is prepared by amonobenzo-15-crown-5-ether and triethyl ortho formate. 4'-Nitrobenzo-crown ethers and 3',4'-dinitrobenzo-crown ethers were prepared by nitration of benzo crown ethers, obtained from the reaction of catechol and oligoethylene glycol ditosylate. Crown ethers containing aldehyde group were synthesized from the reaction of 3,4-dihydroxybenzaldehyde and corresponding ditosylate respectively. The synthesized crown ethers were characterized respectively by IR, NMR, GC-Mass.

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