• Title/Summary/Keyword: 4-hydroxybenzaldehyde

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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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Antioxidant and α-Glucosidase Inhibitory Activities of the Extract from Sparganium stoloniferum Buch.-Ham. Root and Its Constituent Compounds

  • Xu, Ming Lu;Wang, Lan;Hu, Jian He;Wang, Myeong-Hyeon
    • Preventive Nutrition and Food Science
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    • v.14 no.4
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    • pp.354-357
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    • 2009
  • Three compounds, vanillic acid, p-hydroxylcinnamic acid, p-hydroxybenzaldehyde have been isolated from the ethylacetate extract of Sparganium stoloniferum Buch.-Ham roots using silica gel open column chromatography, preparative thin-layer chromatography (pTLC) and reverse phase high performance liquid chromatography. The structures of the compounds were established on the basis of IR, extensive 1D NMR, and MS analyses. The ethylacetate (EtOAc) extract, vanillic acid, and p-hydroxybenzaldehyde showed $\alpha$-glucosidase inhibition activity of 72.71%, 20.13%, and 30.42%, at the concentration of 10 ${\mu}g/mL$, respectively. The EtOAc extract exhibited strong antioxidant activity with an $IC_50$ value of 24.37 ${\mu}g/mL$ against DPPH radical scavenging activity, the vanillic acid, p-hydroxylcinnamic acid, and p-hydroxybenzaldehyde with an $IC_50$ value of 2.10 ${\mu}M$, 1.59 ${\mu}M$, and 2.72 ${\mu}M$ against DPPH, respectively.

Chemical constituents from Polygonum bistorta rhizomes (권삼의 성분)

  • Choi, So-Young;Kwon, Yong-Soo;Kim, Chang-Min
    • Korean Journal of Pharmacognosy
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    • v.31 no.4
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    • pp.426-429
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    • 2000
  • Five compounds have been isolated from the rhizomes of Polygonum bistorta. On the basis of spectral evidences, these compounds were identified as catechol, 4- hydroxybenzaldehyde, umbelliferone, scopoletin and pyrogallol.

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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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DPPH Radical Scavenging Activity of Phenolic Compounds Isolated from the Stem Wood of Acer tegmentosum (산겨릅나무 목질부에서 분리한 페놀성 화합물의 DPPH 라디칼 소거활성)

  • Kwon, Dong-Joo;Kim, Jin-Kyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.39 no.1
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    • pp.104-112
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    • 2011
  • There have been few reports on the constituents and biological activity of stem bark of $Acer$ $tegmentosum$, and no phytochemical and biological studies have been reported for stem wood of $A.$ $tegmentosum$. Two flavan 3-ols (1 and 2), three phenolic acid/alcohols (3~5), and two coumarins (6 and 7) were isolated from the stem wood of $A.$ $tegmentosum$ by repeated column chromatography. The structure of isolated compounds were identified as (+)-catechin (1), (-)-epicatechin (2), $p$-hydroxybenzaldehyde (3), syringic alcohol (4), $p$-tyrosol (5), scopoletin (6), and cleomiscosin A (7) on the basis of spectroscopic evidences such as $^1H$-NMR, $^{13}C$-NMR, 2D-NMR and MS spectrum. $p$-Hydroxybenzaldehyde (3), syringic alcohol (4), scopoletin (6), and cleomiscosin A (7) have not been reported from this plant so far. (+)-Catechin (1) and (-)-epicatechin (2) showed the higher 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity than butylated hydroxyanisole (BHA) used as a positive control.

Anti-Inflammatory, Anti-Angiogenic and Anti-Nociceptive Activities of 4-Hydroxybenzaldehyde

  • Lim, Eun-Ju;Kang, Hyun-Jung;Jung, Hyun-Joo;Kim, Kyung-Hoon;Lim, Chang-Jin;Park, Eun-Hee
    • Biomolecules & Therapeutics
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    • v.16 no.3
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    • pp.231-236
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    • 2008
  • The current work was designed to assess novel pharmacological activities of 4-hydroxybenzaldehyde (HD), a major phenolic constituent of various natural products of plant origin, such as Gastrodia elata Blume. HD exhibited a significant inhibition in the chick chorioallantoic membrane (CAM) angiogenesis. HD also displayed an inhibitory effect in acetic acid-induced permeability in mice. Anti-nociceptive activity of HD was convinced using the acetic acid-induced writhing test in mice. HD was able to suppress production of nitric oxide (NO) and induction of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in the lipopolysaccharide (LPS)-activated RAW264.7 macrophages. HD also diminished the reactive oxygen species (ROS) level elevated in the LPS-activated macrophages. In brief, HD exhibits anti-angiogenic, anti-inflammatory and anti-nociceptive activities possibly via down-regulating iNOS and/or COX-2, which may be partly responsible for pharmacological efficacies of various natural products.

Flavonoids and Aromatic Compounds from the Rhizomes of Zingiber zerumbet

  • Jang Dae Sik;Han Ah-Reum;Park Gowooni;Jhon Gil-Ja;Seon Eun-Kyoung
    • Archives of Pharmacal Research
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    • v.27 no.4
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    • pp.386-389
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    • 2004
  • Repeated column chromatography of the CHCI_3-soluble fraction of Zingiber zerumbet led to the isolation and identification of two aromatic compounds, p-hydroxybenzaldehyde (1) and vanillin (2), and six kaempferol derivatives, kaempferol-3,4',7-O-trimethylether (3), kaempferol-3-O-methylether (4), kaempferol-3,4'-O-dimethylether (5), 4'-O-acetylafzel in (6), kaempferol-3-O-(4-O-acetyl-$\alpha$-L-rhamnopyranoside)], 2',4'-O-diacetylafzelin (7), kaempferol-3-O-(2,4-O-diacetyl-$\alpha$-L-rhamnopyranoside)], and 3',4'-O-diacetylafzelin (8), kaempferol-3-O-(3,4-O-diacetyl-$\alpha$-L-rhamnopyranoside)]. The structures of 1-8 were identifed by analysis of spectroscopic data as well as by comparison with published values. This is the first report on the isolation of compounds 1-3 from this plant.

Anti-platelet Effect of the Phenolic Constituents Isolated from the Leaves of Magnolia obovata

  • Pyo, Mi-Kyung;Koo, Yean-Kyoung;YunChoi, Hye-Sook
    • Natural Product Sciences
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    • v.8 no.4
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    • pp.147-151
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    • 2002
  • In the course of our work on anti-platelet constituents from plants, eight phenolic compounds, $({\pm})-syringaresinol$ (1), 4-hydroxybenzaldehyde (2), 4-hydroxybenzoic acid (3), vanillic acid (4), 4-hydroxy cinnamic acid (5), quercetin 3-O-rhamnoside (6), rutin (7), and quercetin $3-(2^G-rhamnosylrutinoside)$ (8) were isolated from the methanol extract of the leaves of Magnolia obovata. The compounds were identified based on the spectroscopic data. Compound 2, 3, 5, 6, 7 and 8 were isolated for the first time from genus Magnolia. 1 and 6 showed same order of inhibitory potencies as acetylsalicylic acid (ASA) to rat platelet aggregation induced by all the stimulators tested. The remaining six compounds showed only mild effects.