• YAKHAK HOEJI
• /
• v.16 no.4
• /
• pp.162-175
• /
• 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.

• Journal of Pharmaceutical Investigation
• /
• v.29 no.1
• /
• pp.47-53
• /
• 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.

• Journal of Life Science
• /
• v.16 no.7 s.80
• /
• pp.1214-1218
• /
• 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

• Applied Chemistry for Engineering
• /
• v.8 no.1
• /
• pp.8-15
• /
• 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.

• Bulletin of the Korean Chemical Society
• /
• v.35 no.12
• /
• pp.3618-3622
• /
• 2014

Simple and practical synthesis of natural benzofuran derivative eupomatenoid-6 via Horner-Emmons type condensation as the key step is described. The umpolung property of aldehyde derivative, ${\alpha}$-aminophosphonate was efficiently employed in this reaction. ${\alpha}$-Aminophosphonate of anisaldehyde subjected to Horner-Emmons type condensation with 5-bromo-2-methoxybenzaldehyde to yield the deoxybenzoin, which was further methylated and then underwent tandem demethylation-cyclodehydration to afford the benzofuran scaffold in excellent yield. Finally Suzuki coupling with propenyl boronic acid afforded eupomatenoid-6 with an overall yield of 56.8%.

• YAKHAK HOEJI
• /
• v.37 no.3
• /
• pp.247-253
• /
• 1993

Eight new derivatives of allylamine which are related to naftifine and expected to have antifungal activity were synthesized. Schiff base 2a-2d and 2'e-2'h were obtained by conventional methods using trans-cinnamylamine or trans-cinnamaldehyde. The reduction of azomethine linkage with NaBH$_{4}$ yielded secondary amine 3a-3h, which were then methylated by means of HCHO and excess NaBH$_{4}$ or HCOOH to give 4a-4h.

• Korean Journal of Food Science and Technology
• /
• v.30 no.3
• /
• pp.638-643
• /
• 1998

The volatile flavor components in Takju made from mashed glutinous rice and barley rice were identified by GC and GC-MS using polar column. Twenty eight kinds of flavor compounds including 10 alcohols, 9 esters, 2 acids, 7 aldehydes were identified. At the beginning of fermentation 14 kinds of volatile components were detected and the kinds of volatile components were increased up to maximum after fermentation for 16 days. The contents of volatile components in the sample made from glutinous rice contained slightly higher than the sample made from barley rice. Ethyl alcohol, n-propyl alcohol, iso-amyl alcohol, n-hexyl alcohol, hexenyl alcohol, 2-phenylethyl alcohol, ethyl acetate, ethyl succinate, 2-phenylethyl acetate, butyic acid, benzaldehyde and 3-methoxybenzaldehyde were detected in the both of the sample throughout the fermentation process. Five kinds of aldehyde including ethyl propionate, iso-amyl acetate, ethyl caprylate and ethylphenyl acetate were detected only in the sample fermented for 16 days. The main components of the both sample were ethyl alcohol, iso-amyl alcohol, 2-phenylethyl alcohol, 2-phenylethyl acetate, hexenyl alcohol and iso-butyl alcohol. Besides ethyl acetate and benzaldehyde from glutinous rice Takju and hexenyl alcohol from barley rice Takju were found as main components.

• Korean journal of applied entomology
• /
• v.60 no.4
• /
• pp.369-377
• /
• 2021

Mass trapping of the western flower thrips, Frankliniella occidentalis, has been considered as an option to control this pest. This study applied the commercial lures to the hot pepper-cultivating greenhouses and assessed the enhancement of the attracting efficiency by adding to sticky traps. There was no color difference in the attracting efficiency between blue and yellow sticky traps. However, the installation position of the traps was crucial in the greenhouses. The more thrips were captured within host cropping area than outside areas of the crop. In vertical trap position, it was the most optimal to install the traps at the crop crown. Using these installation parameters, the yellow sticky traps captured approximately 1% population of the thrips. To enhance the trapping efficiency, the commercial lures containing aggregation pheromone or 4-methoxybenzaldehyde were added to the yellow sticky traps. However, these commercial lures did not significantly enhance the trapping efficiency compared to the yellow sticky trap alone. In contrast, Y-tube olfactometry assays confirmed the high efficiency of the aggregation pheromone or another plant volatile (methyl isonicotinate) to attract the thrips. Interestingly, these lure components had lower attracting efficiencies compared to the hot pepper flowers. The high attractive efficiency of the flowers was supported by the observation that the commercial lure was effective to enhance the trapping efficiency of the yellow sticky trap against F. occidentalis in Welsh onion (Allium fistulosum) field without any flowers. This study indicates the limitation of the commercial lures in application to hot pepper fields for the mass trapping of F. occidentalis. It also suggests active volatile component(s) from hot pepper flowers to attract F. occidentalis.

• Korean Journal of Food Science and Technology
• /
• v.33 no.6
• /
• pp.784-788
• /
• 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.

• Archives of Pharmacal Research
• /
• v.29 no.10
• /
• pp.849-858
• /
• 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.