• Korean Journal of Pharmacognosy
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• v.19 no.3
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• pp.188-192
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• 1988

An aromatic hydrocarbon, $mp\;79{\sim}80^{\circ},\;C_{11}H_{12}O_5$, was first isolated from Phyllostachys sp. and identified as 1, 4-benzenedicarboxylic and 2'-hydroxyethylmethyl ester. Five compounds isolated after alkali hydrolysis were identified as vanillin, 4-hydroxyacetophenone, terephthalic acid, 4-hydroxybenzaldehyde and friedelin.

• Natural Product Sciences
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• v.21 no.3
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• pp.219-225
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• 2015

In the previous experiments, we reported that ethanol extract of Gastrodiae Rhizoma, the dried tuber of Gastrodia ElataBlume (Orchidaceae) increased pentobarbital-induced sleeping behaviors. These experiments were undertaken to know whether 4-hydroxybenzaldehyde (4-HBD), is one of the major compounds of Gastrodiae Rhizoma increases pentobarbital-induced sleeping behaviors and changes sleep architectures via activating GABA_A-ergic systems in rodents. 4-HBD decreased locomotor activity in mice. 4-HBD increased total sleep time, and decreased of sleep onset by pentobarbital (28 mg/kg and 40 mg/kg). 4-HBD showed synergistic effects with muscimol (a GABA_A receptor agonist), shortening sleep onset and enhancing sleep time on pentobarbital-induced sleeping behaviors. On the other hand, 4-HBD (200 mg/kg, p.o.) itself significantly inhibited the counts of sleepwake cycles, and prolonged total sleep time and non-rapid eye movement (NREM) in rats. Moreover, 4-HBD increased intracellular Cl⁻ levels in the primary cultured cerebellar cells. The protein levels of glutamic acid decarboxylase (GAD) and GABA_A receptors subunits were over-expressed by 4-HBD. Consequently, these results demonstrate that 4-HBD increased NREM sleep as well as sleeping behaviors via the activation of GABA_A-ergic systems in rodents.

• Parasites, Hosts and Diseases
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• v.58 no.1
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• pp.7-14
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• 2020

Toxoplasma gondii is an intracellular protozoan parasite that infects approximately one third of the human population worldwide. Considering the toxicity and side effects of anti-toxoplasma medications, it is important to develop effective drug alternatives with fewer and less severe off-target effects. In this study, we found that 4-hydroxybenzaldehyde (4-HBA) induced autophagy and the expression of NAD-dependent protein deacetylase sirtuin-1 (SIRT1) in primary murine bone marrow-derived macrophages (BMDMs). Interestingly, treatment of BMDMs with 4-HBA significantly reduced the number of macrophages infected with T. gondii and the proliferation of T. gondii in infected cells. This effect was impaired by pretreating the macrophages with 3-methyladenine or wortmannin (selective autophagy inhibitors) or with sirtinol or EX527 (SIRT1 inhibitors). Moreover, we found that pharmacological inhibition of SIRT1 prevented 4-HBA-mediated expression of LC3-phosphatidylethanolamine conjugate (LC3-II) and the colocalization of T. gondii parasitophorous vacuoles with autophagosomes in BMDMs. These data suggest that 4-HBA promotes antiparasitic host responses by activating SIRT1-mediated autophagy, and 4-HBA might be a promising therapeutic alternative for the treatment of toxoplasmosis.

• Biomolecules & Therapeutics
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• v.17 no.3
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• pp.263-269
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• 2009

4-Hydroxybenzaldehyde, a phenolic compound found in a variety of natural sources, was previously shown to contain anti-inflammatory and related anti-angiogenic and anti-nociceptive activities. The present work was designed to assess some pharmacological activities of 2,4-dihydroxybenzaldehyde (DHD), an analogue of 4-hydroxybenzaldehyde. DHD exhibited a significant inhibition in the chick chorioallantoic membrane (CAM) angiogenesis, and its $IC_{50}$ value was $2.4\;{\mu}g/egg$. DHD also contained in vivo anti-inflammatory activity using acetic acid-induced permeability and carrageenan-induced air pouch models in mice. In the air pouch model, DHD showed significant suppression in exudate volume, number of polymorphonuclear leukocytes and nitrite content. DHD showed an anti-nociceptive activity in the acetic acid-induced writhing test in mice. It also suppressed enhanced production of nitric oxide (NO) and elevated expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. It was able to slightly decrease the level of reactive oxygen species in the stimulated macrophages. DHD at the used concentrations couldn't modulate the viabilities of RAW264.7 cells. Taken together, like 4-hydroxybenzaldehyde, DHD contains anti-angiogenic, anti-inflammatory and anti-nociceptive activities.

• Applied Biological Chemistry
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• v.43 no.4
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• pp.298-302
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• 2000

In our investigation on chemical constituents of edible mushrooms, seven compounds I-VII have been isolated from the methanolic extract of the fruit body of Sarcodon aspratus. The methanolic extract was separated by solvent partition, silica gel column chromatography and Sephadex LH-20 column chromatography, and compounds I-VII were finally purified by preparative HPLC or TLC. Their structures were assigned as 4-hydroxybenzoic acid methyl ester, 4-hydroxybenzaldehyde, cyclo(Ala-Pro), adenosine, nicotinamide, BL V, linoleic acid, respectively, on the basis of mainly $^1H\;NMR$ spectra.

• Korean Journal of Pharmacognosy
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• v.38 no.3 s.150
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• pp.291-295
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• 2007

Eight compounds were isolated from the whole plants of Euphorbia supina (Euphorbiaceae) through repeated silica gel, YMC gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as 7-hydroxy-6-methoxycoumarin (scopoletin) (1), p-hydroxybenzaldehyde (2), methyl gallate (3), gallic acid (4), quercetin (5), quercetin $3-O-{\alpha}-L-arabinofuranoside$ (avicularin) (6), kaempferol $3-O-{\alpha}-L-arabinofuranoside$ (juglanin) (7) and kaempferol $3-O-{\beta}-D-glucopyranoside$ (astragaline) (8) by spectroscopic (NMR and MS) analysis.

• Natural Product Sciences
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• v.11 no.3
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• pp.123-126
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• 2005

Gastrodia elata Blume (Chunma) belongs to Orchidaceae, which is a perennial parasitic herbaceous plant and grows in the woods of the central provinces of China, Korea and Japan. Recently, the constituents of the tubers of this plant have been investigated by researchers who have revealed the presence of phenolic compounds including gastrodin as a major constituent, together with 4-hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, parishin, 4,4-dihydroxybenzyl sulfoxide, vanillin, vanillyl alcohol, beta-sitosterol, organic acids and polysaccharides, etc. In this study, we used ultrasonicator and two kinds of enzymes for enhancement of extraction yield. We also used electronic nose for the aroma pattern analysis of Chunma extracts. The concentrations of glucose and functional constituents (gastrodin, vanillin, 4-hydroxybenzaldehyde and 4-hydroxybenzyl alcohol) were measured by biochemistry analyzer and HPLC, respectively. Therefore, we showed that the yield of extraction was increased and discomfortable odor was reduced.

• Journal of Applied Biological Chemistry
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• v.60 no.1
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• pp.49-54
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• 2017

In the course of screening tyrosinase inhibitory activity, EtOAc-soluble fraction of Coix lachryma-jobi var. mayuen Stapf. (Gramineae) roots showed significant inhibition. Further fractionation of the EtOAc-soluble fraction resulted in six compounds, which were identified as (+)-icariol $A_2$ (1), zhepiresionol (2), 4-hydroxybenzaldehyde (3), trans-${\rho}$-coumaric acid (4), N-(2-hydroxy-4-methoxyphenyl)-2-hydroxyacetamide (5), and coixol (6). The chemical structures of these compounds were identified on the basis of spectroscopic methods (MS, 1D and 2D NMR) and comparison with literature values. Compound 1 was first reported from this plant. Also, this is the first time that the isolation of compound 5 has been reported from nature source. Among the isolated compounds, compounds 4 and 6 showed enzyme inhibitory activity, with $IC_{50}$ values of 6.5 and $62.4{\mu}M$, respectively, in comparison with these of positive control, arbutin.

• Analytical Science and Technology
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• v.32 no.6
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• pp.217-224
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• 2019

In this study, to evaluate the effectiveness and safety of oral therapy using Gastrodiae Rhizoma, a new HPLC-PDA analysis method was developed for the simultaneous quantitation of the three major components: (1) gastrodin, (2) gastrodigenin, and (3) p-hydroxybenzaldehyde, in steam processed and unprocessed tubers of Gastrodia elata Blume. The clear separation of the three components was achieved on a C18 column (250 × 4.6 mm, 5 ㎛) by gradient elution using water (including 0.1 % formic acid) and acetonitrile as the mobile phase. The flow rate was 1.0 mL/min, and the UV detector wavelength was set at 270 nm. The results demonstrate satisfactory linearity, recovery, precision, accuracy, stability, and robustness. The established HPLC-PDA method was applied to quantify three major compounds in 59 samples of G. elata Blume tubers. Finally, the steam processed and unprocessed tubers of G. elata Blume were successfully distinguished by pattern recognition analysis.

• Applied Biological Chemistry
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• v.51 no.4
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• pp.316-320
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• 2008

Ten compounds, (+)-pinoresinol (1), (-)-balanophonin (2), gallicin (3), vanillin (4), 4-hydroxybenzaldehyde (5), coniferaldehyde (6), betulinic acid (7), ursolic acid (8), 5-hydroxymethyl furfural (9), and malic acid (10), were isolated from a EtOAc-soluble fraction of the seeds of Cornus officinalis. The structures of these compounds were elucidated by spectroscopic methods as well as by comparison with reported values. Compounds 1, 2, and 4-7 were isolated from this species for the first time. All the isolates (1-10) were subjected to an in vitro bioassay to evaluate their inhibitory activity against advanced glycation end products (AGEs) formation. Among these, compounds 2 and 3 showed the significant inhibitory activity on AGEs formation with $IC_{50}$ values of 27.81 and 18.04${\mu}M$, respectively.