• Title/Summary/Keyword: 4-hydroxy-3-methoxybenzaldehyde

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Synthesis and evaluation of antimicrobial-antitumor activities of methylthiosemi-carbazones and thiocarbohydrazones

  • Rhee, Shang-Hi
    • YAKHAK HOEJI
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    • v.16 no.4
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    • pp.162-175
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    • 1972
  • Fifty six compounds of 4-methylthiosemicarbazone and thiorcarbohydrazone derivatives were prepared and subjected to biological tests. The following five compounds, 2-hydroxybenzaldehyde monothiocarbohydrazone (2),4-methylbenzaldehyde monothiocarbohydrazone (8), 1-(2-hydroxybenzaldehyde)-5(4-hydroxy-3-methoxybenzaldehyde) dithiocarbohydrazone (45), 1-(2-hydroxybenzaldehyde)-5-furfural dithiocarbohydrazone (46) and 1-benzaldehyde-5-cinnamaldehyde dithiocarbohydrazone (49) exhibited marked antimicrobial activity against E. coli, St. aureus and P. chrysogenum. In addition to these compounds, 3-methoxybenzaldehyde monothiocarbohydrazone (12) and 4-methylbenzaldehyde dithiocarbohydrazone (29) showed marked inhibition of HeLa cell growth at the concentration of 10 ${\nu}$g/ml. It was generally observed that most compounds demonstrated significant antifungal activity against P. chrysongenum but only one compound, 3-hydroxy-4-methoxybenzaldehyde dithiocarbohydrazone (39), exerted antituberculosis activity against M. tuberculosis H$_{37}$ RV at the concentration of 10 ${\nu}$g/ml.

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Pharmacokinetics of 4-hydroxy-3-methoxybenzaldehyde and p-hydroxybenzaldehyde, Constituents of Gastrodia Elata, in Rats (천마 성분인 4-히드록시-3-메톡시벤즈알데히드 및 파라-히드록시벤즈알데히드의 흰쥐에서의 약물동태)

  • Yong, Chul-Soon;Quan, Qi-Zhe;Kim, Jeoung-Ae;Ha, Jeoung-Hee;Lee, Dong-Ung;Huh, Keun
    • Journal of Pharmaceutical Investigation
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    • v.29 no.1
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    • pp.47-53
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    • 1999
  • Gastrodia elata (GE) is an oriental medicinal herb which has been used traditionally for the treatment of various brain diseases including convulsion and epilepsy. The purpose of this study was to determine pharmacokinetic parameters of 4-hydroxy-3-methoxybenzaldehyde (HMBA) and p-hydroxybenzaldehyde (PHBA), constituents of GE, in rats. Male rats were cannulated in the femoral vein, femoral artery, bile duct and ureter. They received a single i.v. bolus dose of either HMBA or PHBA through the femoral vein. The concentration of HMBA or PHBA in plasma, bile and urine samples were analyzed by reversed-phase HPLC. HMBA and PHBA have very short half-lives, i.e. 4.03 and 2.26 minutes respectively. Most of HMBA and PHBA were thought to be eliminated through metabolism as the metabolized fraction approaches unity. Derivatives of HMBA or PHBA with longer biological half-lives should be designed to develop better anticonvulsants and more complete qualitative and quantitative understanding of the overall pharmacokinetic fate of these compounds awaits further investigation.

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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

Analysis of 4-hydroxy-3-methoxybenzaldehyde pyrolyzates by Curie-point pyrolyzer-GC/MSD (Curie-point pyrolyzer-GC/MSD를 이용한 4-hydroxy-3-methoxybenzaldehyde의 열분해물 분석)

  • Yu, Euy Kyung;Kim, Ok-Chan
    • Applied Chemistry for Engineering
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    • v.8 no.1
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    • pp.8-15
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    • 1997
  • This study was carried out to present a analysis of pyrolytic degradation of 4-hydroxy-3-methoxybenzal dehyde(vanillin) pyrolyzed at $330^{\circ}C{\sim}920^{\circ}C$ by Curie-point pyrolyzer connected with GC/MSD by on-line system. Identified by GC/MSD were 100 pyrolytic products of vanillin. The pyrolysis of the compound gave benzene, phenol, 1,3-cyclopentadiene, methyl benzene, benzaldehyde, benzofuran, and cresol as major products, which were produced by pyrolytic degradation and synthesis of vanillin radicals.

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Capsaicin Intake Estimated by Urinary Metabolites as Biomarkers (뇨중 대사체 정량에 의한 capsaicinoid의 생화학적 섭취지표 개발 연구)

  • Choo, Yeon-Soo;Kwon, Hoon-Jeong
    • Korean Journal of Food Science and Technology
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    • v.33 no.6
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    • pp.784-788
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    • 2001
  • Reliable data on the exposure of capsaicin, which evokes hot sensation in hot red pepper, are important prerequisites for studying biological functions of capsaicin in human body since its roles are controversial according to animal and epidemiological studies. To get accurate data, the use of urinary biomarkers was considered as a measure of internal exposure of capsaicin. After 2-day-capsaicin depletion five to six women in their 20's were instructed to eat 60 or 80 g/day hot red pepper soybean paste as a capsaicin source with meal which did not contain capsaicinoid, and to collect their urine separately. HPLC conditions were set to detect capsaicinoid and urinary metabolites at the same time. Most of capsaicinoid were excreted in the form of 4-hydroxy-3-methoxybenzoic acid in three subjects at the highest dose. This result suggests the oxidation of the 4-hydroxy3-methoxybenzaldehyde, the hydrolysis product of capsaicin, is the major metabolic pathway in the human body, whereas the reduction of the aldehyde is the major route in rats. However, neither any metabolite nor the parent compound was ever shown in two of the subjects reflecting large individual differences of capsaicin absorption and/or biotransformation.

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Anti-inflammatory Action of Phenolic Compounds from Gastrodia elata Root

  • Lee, Ji-Yun;Jang, Young-Woon;Kang, Hyo-Sook;Moon, Hee;Sim, Sang-Soo;Kim, Chang-Jong
    • Archives of Pharmacal Research
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    • v.29 no.10
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    • pp.849-858
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    • 2006
  • Previous screening of the pharmacological action of Gastrodia elata (GE) root (Orchidaceae) showed that methanol (MeOH) extracts have significant anti-inflammatory properties. The antiinflammatory agents of GE, however, remain unclear. In this experiment, MeOH extracts of GE were fractionated with organic solvents for the anti-inflammatory activity-guided separation of GE. Eight phenolic compounds from the ether (EtOEt) and ethyl acetate (EtOAc) fractions were isolated by column chromatography: 4-hydroxybenzaldehyde (I), 4-hydroxybenzyl alcohol (II), benzyl alcohol (III), bis-(4-hydroxyphenyl) methane (IV), 4(4'-hydroxybenzyloxy)benzyl-methylether (V), 4-hydroxy-3-methoxybenzyl alcohol (VI), 4-hydroxy-3-methoxybenzaldehyde (VII), and 4-hydroxy-3-methoxybenzoic acid (VIII). To investigate the anti-inflammatory and anti-oxidant activity of these compounds, their effects on carrageenan-induced paw edema, arachidonic acid (AA)-induced ear edema and analgesic activity in acetic acid (HAc)-induced writhing response were carried out in vivo; cyclooxygenase (COX) activity, reactive oxygen species (ROS) generation in rat basophilic leukemia (RBL 2H3) cells and 1,1-diphenyl-2-picryl-hydroazyl (DPPH) scavenging activity were determined in vitro. These phenolic compounds not only had anti-inflammatory and analgesic properties in vivo, but also inhibited COX activity and silica-induced ROS generation in a dose-dependent manner. Among these phenolic compounds, compound VII was the most potent anti-inflammatory and analgesic. Compound VII significantly inhibited silica-induced ROS generation and compound VI significantly increased DPPH radical scavenging activity. Compounds I, II and III significantly inhibited the activity of COX-I and II. These results indicate that phenolic compounds of GE are anti-inflammatory, which may be related to inhibition of COX activity and to anti-oxidant activity. Consideration of the structure-activity relationship of the phenolic derivatives from GE on the anti-inflammatory action revealed that both C-4 hydroxy and C-3 methoxy radicals of benzyl aldehyde play an important role in anti-inflammatory activities.