• 대한본초학회지
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• 제21권2호
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• pp.1-7
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• 2006

Objectives : The purpose of this study is to isolate tyrosinase inhibitory material from Pinellia ternata and characterize its own structure and activity. Methods : Pinellia ternata (600g) was extracted with 95% methanol (1L) at $37^{\circ}C$ for 4 days, with shaking at 250rpm. The extract was further solvent-fractionated with n-hexane, chloroform, ethylacetate and water. The active fraction was subjected to JAI recycling prep-HPLC JAIGEL GS-320 column. The structure was identified for the active peak with NMR and GC. Results : Tyrosinase was potently inhibited by 95% methanol extracts from Pinellia ternata. The $IC_{50}$ value of the extracts was estimated to be 0.05mg/ml. The extracts was divided into four solvent-fractions, and the most potent tyrosinase inhibition was found in ethylacetate layer. $IC_{50}$ value of ethylacetate fraction was 0.001mg/ml. This fraction was further purified with JAI Recycling Preparative HPLC (Model: LC 9104). The isolated compound showing inhibitory activity was characterized on its chemical structure by NMR and the compound was identified as 3,4-dihydroxybenzaldehyde. $IC_{50}$ was found to be 7.74 ${\mu}M$ which is much lower than that of kojic acid $(66.5{\mu}M)$. Conclusions : The data suggest that 3,4-dihydroxybenzaldehyde isolated and identified from Pinellia ternata is very strong inhibitor to melanin biosynthesis.

• 대한약학회:학술대회논문집
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• 대한약학회 2000년도 춘계총회 및 학술대회
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• pp.209.2-209.2
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• 2000

• 전기화학회지
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• 제7권4호
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• pp.167-172
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• 2004

3,4-dihydroxybenzaldehyde(3,4-DHB) was oxidatively el electropolymerized on glassy carbon (GC) electrodes to prepare CC/p-3,4-DHB type electrodes, which were subsequently modified with 3,4-dihydroxybenzoic acid(3,4-DHBA) using 0.05M HCI as a catalyst. The esterification reactions were performed between -OH sites on the polymeric film surface of the p-3,4-DHB and the -COOH sites within the 3,4-DHBA molecules in solution. These reactions had a rate constant value of $1.1\times10^{-1}\;s^{-1}$ for the esterification step as obtained from the first-order rate constant in the solution. The electrochemical responses of the GC/p-3,4-DHB-3,4-DHBA electrodes exert an influence upon the buffer solution, its pH and applied potential ranges. The redox process of the electrode was more easily controlled by charge transfer kinetics than that of the CC/p-3,4-DHB. The modified electrodes had redox active sites that were 10 times more active than those present before modification. The electrical admittance of the modified electrodes was also three times higher than that of the unmodified electrodes. After being annealed in ethanol for 20 hrs the electrodes brought about a 3.3 times greater change of water molecules in the redox reaction. The modified electrodes are stable in the potential range of 0.4 to 0.55V.

• 동의생리병리학회지
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• 제18권3호
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• pp.846-853
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• 2004

This study was carried out for establishment of toxicological monitoring system in oriental medicinal plants. Hence on our research, we used Banha(Pinellia ternata) and Kangbanha, Bubbanha, Jaebanha, Geokbanha by distinguished processing methods. These are frequently used in Bangyakhabpeon, which is one of the most well-known clinical book in oriental medicine. As we reviewed the reported documents, we judge homogentisic acid(HA) and 3,4-dihydroxybenzaldehyde(3,4-DBA) as poisonous substance and to verify its existence, we established analysis condition of HPLC by gaining sequential fraction extracts and studied the degree of its virulence to provide basic information on the guidelines of using this medicine. Optimum condition of HPLC was H₂O : MeOH : CH₃COOH (57:35:8) in HA and 3,4-DBA analysis. HA content of raw Banha was 11.03mg/100g and HA contents of its processed product were decreased. Exceptionally, Jaebanha was increased in 175.97% than raw Banha. 3,4-DBA content of raw Banha was 2.93mg/100g and 3,4-DBA contents of its processed product were decreased. These results will be applies in intake guideline establishment, quality control and stability evaluation of oriental medicinal plants.

• 대한화학회지
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• 제47권3호
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• pp.199-205
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• 2003

우라닐 이온, $UO^+_2$와 Schiff-base 와의 착화합물이 글리실글라이신과 살리실알데히드, 2-히드록시-1-나프트알데히드, 2,3-디히드록시 벤즈알데히드 그리고 2,4-디히드록시 벤즈알데히드와의 축합에 의해 합성되었으며 이들 착화합물의 특성을 원소분석, 전도도 측정, 자기화율 측정, UV, IR, NMR 스펙트라와 DTA, TG, DSC 결과를 이용하여 조사하였다. 구조와 열분해 메카니즘이 제안되었다.

• Toxicological Research
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• 제33권4호
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• pp.325-332
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• 2017

3-Bromo-4,5-dihydroxybenzaldehyde (BDB) is a natural bromophenol compound that is most commonly isolated from red algae. The present study was designed to investigate the anti-inflammatory properties of BDB on atopic dermatitis (AD) in mice induced by 2,4-dinitrochlorobenzene (DNCB) and on lipopolysaccharide (LPS)-stimulated murine macrophages. BDB treatment (100 mg/kg) resulted in suppression of the development of AD symptoms compared with the control treatment (induction-only), as demonstrated by reduced immunoglobulin E levels in serum, smaller lymph nodes with reduced thickness and length, a decrease in ear edema, and reduced levels of inflammatory cell infiltration in the ears. In RAW 264.7 murine macrophages, BDB (12.5, 25, 50, and $100{\mu}M$) suppressed the production of interleukin-6, a proinflammatory cytokine, in a dose-dependent manner. BDB also had an inhibitory effect on the phosphorylation of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-${\kappa}B$) and signal transducer and activator of transcription 1 (STAT1; Tyr 701), two major signaling molecules involved in cellular inflammation. Taken together, the results show that BDB treatment alleviates inflammatory responses in an atopic dermatitis mouse model and RAW 264.7 macrophages. These results suggest that BDB may be a useful therapeutic strategy for treating conditions involving allergic inflammation such as atopic dermatitis.

• Biomolecules & Therapeutics
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• 제17권3호
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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.

• Journal of Microbiology and Biotechnology
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• 제29권8호
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• pp.1193-1203
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• 2019

We investigated the protective effects of 3-bromo-4,5-dihydroxybenzaldehyde (BDB) from Polysiphonia morrowii Harvey against hydrogen peroxide ($H_2O_2$)-induced apoptosis in Vero cells. BDB exhibited scavenging activity for DPPH, hydroxyl, and alkyl radicals. BDB also inhibited $H_2O_2$-induced lipid peroxidation, cell death, and apoptosis in Vero cells by inhibiting the production of ROS. To evaluate the molecular mechanisms of apoptosis inhibition, the expression of Bax/Bcl-xL and $NF-{\kappa}B$ was assessed by western blot assay. BDB significantly suppressed the cleavage of caspase-9 and PARP and reduced Bax levels in $H_2O_2$-induced Vero cells. Besides, BDB suppressed the phosphorylation of $NF-{\kappa}$B and the translocation of p65 in $H_2O_2$-induced cells. Furthermore, we evaluated the effect of BDB on ROS production, cell death, and lipid peroxidation in an $H_2O_2$-stimulated zebrafish embryo model. Taken together, these results indicated that ROS generation and cell death were significantly inhibited by BDB in zebrafish embryos, thereby proving that BDB exerts excellent antioxidant activity in vitro and in vivo.

• 생약학회지
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• 제46권4호
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• pp.352-364
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• 2015

The aim of this study was to quantitatively analyze for quality assessment of eighteen marker compounds, including homogentisic acid, 3,4-dihydroxybenzaldehyde, spinosin, liquiritin, hesperidin, ginsenoside Rg1, liquiritigenin, ginsenoside Rb1, glycyrrhizin, 6-gingerol, atractylenolide III, honokiol, costunolide, dehydrocostuslactone, atractylenolide II, nootkatone, magnolol, and atractylenolide I, in Hyangsayukgunja-tang using an ultra-performance liquid chromatography-electrospray ionization-mass spectrometer. The column for separation of eighteen marker components were used a UPLC BEH $C_{18}$ analytical column ($2.1{\times}100mm$, $1.7{\mu}$) and kept at $45^{\circ}C$ by gradient elution with 0.1% (v/v) formic acid in water and acetonitrile as mobile phase. The flow rate and injection volume were 0.3 mL/min and $2.0{\mu}l$, respectively. The correlation coefficient of all marker compounds was ${\geq}0.9914$, which means good linearity, within the test ranges. The limits of detection and quantification values of the all analytes were in the ranges 0.04-1.11 and 0.13-3.33 ng/mL, respectively. As a result, five compounds, homogentisic acid, 3,4-dihydroxybenzaldehyde, spinosin, liquiritigenin, and atractylenolide I, in this sample were not detected and the amounts of the 13 compounds except for the 5 compounds were $8.10-6736.37{\mu}g/g$ in Hyangsayukgunja-tang extract.

• Applied Biological Chemistry
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• 제50권4호
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• pp.358-361
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• 2007

옻나무 목질부를 열수 추출하고, 얻어진 추출물을 $CHCl_3$, EtOAc, H-BuOH 및 $H_2O$로 용매 분획하였다. 이중 EtOAc와 n-BuOH분획으로부터 silica gel, ODS 및 Sephadex LH-20 column chromatography로 정제하여 4개의 화합물을 분리하였다. 각 화합물의 화학구조는 NMR 스펙트럼 데이터를 해석하여, sinapyl aldehyde (1), 2,4-dihydroxybenzaldehyde (2), 2,4-dihydroxybenzoic acid (3) 및 2,4-dihydroxyphenyl-glyoxylic acid (4)으로 동정하였다. 이 화합물들 중 2-4은 옻나무목질부에서 처음 분리된 화합물이다. 이들 화합물 중 sinapyl aldehyde (1)와 2,4-dihydroxyphenylglyoxylic acid (4)의 DPPH radical 소거작용이 $34.7{\pm}0.6%$와 $43.8{\pm}0.9%$로 나타나 합성항산화제인 $BHT(14.4{\pm}0.3%)$보다 높게 나타났다.