• Journal of the Korean Society of Food Science and Nutrition
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• v.27 no.5
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• pp.1015-1018
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• 1998

Capsaicin(8-methyl-N-vanillyl-6-nonenamide: CAP) known well as a major compound of not taste in hot pepper, was investigated for the inhibition effect on in vitro nitrosation. CAP(100$\mu$mol) inhibited the formation of N-nitrosoproline(NPRO) and N-nitrosothioproline(NTPRO) by 56% and 26%, respectively. Vanillyl alcohol inhibited the nitrosation of proline by a concentration-dependent manner, and vanillic acid and vanillin were less effective in blocking the nitrosation of proline compared to CAP and anillyl alcohol. The inhibitory effect of NPRO formation by CAP was evaluated to similar with alpha-tocopherol, and vanillyl alcohol was more effective than alpha-tocopherol in blocking the nitrosation of proline. Our results suggested that CAP and its metabolites such as vanillyl alcohol could inhibit endogenous nitrosation in hydrophobic biological environment.

• Korean Journal of Medicinal Crop Science
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• v.21 no.4
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• pp.282-288
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• 2013

Gastrodia elata Blume is a achlorophyllous orchid plant that has been used in traditional medicine to treat many human illnesses, such as vertigo, hemiplegia, and epilepsy. It contains three major pharmacological substances; gastrodin, ergothioneine, and vanillyl alcohol. Here we investigated the quantitative changes in those functional components by cultivation conditions and harvest times. The content of ergothioneine was different with cultivation areas, while gastrodin accumulated the higher levels than vanillyl alcohol regardless of cultivation areas. The smaller tubers contained the higher concentrations of gastrodin and the lower concentrations of ergothioneine than did the larger tubers. The cultivation under sun shade screen increased the concentrations of both gastrodin and vanillyl alcohol but decreased the levels of ergothioneine. We also determined the contents of functional substances depending on the harvest times. The concentration of gastrodin was higher in October than in April, while the level of ergothioneine was higher in April than in October. Interestingly, the use of sexually propagated seed tubers produced 1.9 times higher levels of gastrodin compared to vegetatively propagated seed tubers. In this study, we found that three major functional substances in G. elata tubers altered depending on various cultivation practices, which might be important to increase the economic values of G. elata tubers.

• Journal of Microbiology and Biotechnology
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• v.31 no.2
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• pp.317-326
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• 2021

Vanillyl alcohol (VA), which is abundant in Vanilla bean, has strong antioxidant activity. However, the use of VA in the food and cosmetics industries is limited, due to its low solubility in emulsion or organic solvents. Meanwhile, medium chain fatty acids and medium chain monoglycerides have antibacterial activity. We synthesized butyric acid vanillyl ester (BAVE) or caprylic acid vanillyl ester (CAVE) from VA with tributyrin or tricaprylin through transesterification reaction using immobilized lipases. BAVE and CAVE scavenged 2,2-diphenyl-1-picrylhydrazyl radicals in organic solvents. In addition, BAVE and CAVE decreased the production rate of conjugated diene and triene in the menhaden oil-in-water emulsion system. While BAVE showed no antibacterial activity, CAVE showed antibacterial activity against food spoilage bacteria, including Bacillus coagulans. In this study, the antibacterial activity of vanillyl ester with medium chain fatty acid was first revealed. Zeta potential measurements confirmed that BAVE and CAVE were inserted into B. coagulans membrane. In addition, the propidium iodide uptake assay and fluorescent microscopy showed that CAVE increased B. coagulans membrane permeability. Therefore, CAVE is expected to play an important role in the food and cosmetics industries as a bi-functional material with both antioxidant and antibacterial activities.

• Journal of Korean Society of Forest Science
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• v.43 no.1
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• pp.14-19
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• 1979

On treatment with sodium hydroxide at $165^{\circ}$ for 1.5~3hr followed by air oxidation. vanillyl alcohol afforded colored materials. $^{13}C$-NMR spectrum of the material did not show any absorptions assigned to the carbons of chromophoric structures, but gave the valuable information on the chemical structures of the condensation products. On the other hand, the colored material specifically labelled by $^{13}C$ at the benzylic position was prepared by alkali treatment of vanillyl alcohol-[carbinol-$^{13}C$] followed by air oxidation, and $^{13}C$-NMR spectra of the material exhibited absorptions at 101.7 and 104.6 ppm due to the carbons of a quinonemethide structure, indicating that the quinomethide unit would be one of the important types of chromophores in which benzylic carbon of vanillyl alcohol was included.

• Journal of Korean Society of Forest Science
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• v.38 no.1
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• pp.55-59
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• 1978

알카리 리그닌의 착색구조(着色構造)를 확실(確實)히 하기 위(爲)하여 리그닌 모델 화합물(化合物)인 바니릴알콜을 질소하(窒素下)에 알카리로 처리(處理)하였다. 그림-1과 같이 ${\alpha}$-1 결합(結合)인 화합물(化合物) I., ${\alpha}$-1와 ${\alpha}$-5의 결합(結合) 구조(構造)인 화합물(化合物) II, III, IV와 ${\alpha}$-5결합(結合) 구조(構造)인 화합물(化合物) V를 단리(單離) 동정(同定)하였다. 이들 화합물(化合物)은 공기산화(空氣酸化) 및 알카리 처리(處理)에 의(依)해 착색(着色)되었다.

• 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 Industrial and Engineering Chemistry
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• v.68
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• pp.380-386
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• 2018

A sustainable method was developed for the upgrade of biomass derived vanillin (a typical model compound of lignin) into the potential liquid biofuels over a layered double hydroxide supported Pd catalyst (abbreviated as CoAl-LDH/Pd). The CoAl-LDH/Pd catalyst showed high catalytic activity towards the hydrodeoxygenation of vanillin into 2-methoxy-4-methylphenol (MMP) under mild conditions in aqueous media. High MMP yield up to 86% was produced at $120^{\circ}C$ after 4 h. Kinetic studies revealed that the rate-determining step for the hydrodeoxygenation of vanillin was the hydrogenolysis of vanillyl alcohol. More importantly, the CoAl-LDH/Pd catalyst was highly stable without the loss of activity.

• Food Science and Preservation
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• v.13 no.2
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• pp.131-137
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• 2006

In order to reduce the damage of effective component during processing, we carried out hot-water extraction monitering in Gastrodia elata Blume by response surface methodology. The extraction con야tions for vanillyl alcohol, vanillin and coumarin were optimized at 91.07, 93.73 and $96.30^{\circ}C$, for 2.64, 2.58 and 3.84 hr, at the concentration of 15.16, 21.56 and 19.88 mL/g, respectively. The optimal condition for extraction of total phenolics was acheved at $98.14^{\circ}C$, 3.20 hr and 18.63 mL/g. This study elicited regression formula for each variable, and superimposed the total optimal conditions of extraction for effective compounds and optimal condition for antioxidant characteristics dividing processing factors. It is shown that the predicted result under the extraction condition as follows: extraction temperature for $90{\sim}100^{\circ}C$, extraction time for $3{\sim}4hr$, and solvent volume of $15{\sim}20mL/g$ of sample.

• Journal of the Korean Wood Science and Technology
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• v.9 no.2
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• pp.1-30
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• 1981

To investigate the formation of the chromophoric structures taking place during the alkaline pulping vanillyl alcohol [${\alpha}-^{13}C$] guaiacylglycerol-${\beta}$-aryl ether [${\alpha}-^{13}C$ or ${\gamma}-^{13}C$] and phenylcoumarn [${\alpha}-^{13}C$] units as model lignins were treated with 1N sodium hydroxide at 165$^{\circ}C$ for 1.5-3 hours. From the chemical structures of the isolated products and $^{13}C$-NMR Spectra of the reaction mixtures, the main conclusion is as follows; 1) Condensation products of II-1-5 were identified from the reaction mixture of vanillyl alcohol treated with alkali and theses compounds afforded the quinonmethide structure(Fig. 3-7) by air oxidation. 2) Treatment of guaiacylglycerol-${\beta}$-aryl ether unit gave ${\varphi}$-aryl-${\beta}$-aroxy quinone structures (IV-15, IV-16), diguaiacyl-1, 4-penta-diene ${\beta}$, ${\beta}$'-diaroxyl distyrene methane unit, ${\beta}$-aroxy distyrene methane. These distyrene methanes of the compounds are transformed by air oxidation into the corresponding o-quinonemethide units (V-8, V-9). 3) On the treatment of phenylcoumaran, the stilbene derivative was formed in quantitative yield and dimerized(VI-11) in preference to oxidation to the corresponding extended quinone structures. The chromophoric structures taken place during the alkaline treatment of the model lignins are thought to be some important types in alkaline pulping on the basis of the reaction mechanism in this experiment.

• The Korean Journal of Food And Nutrition
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• v.30 no.5
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• pp.973-982
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• 2017

Gastrodia elata Blume often has been used for the treatment of headaches, convulsions, hypertension, and neurodegenerative diseases. The main active constituents are gastrodin, 4-hydroxybenzyl alcohol, vanillyl alcohol, 4-hydroxybenzylaldehyde and parishin A, B, C and E. Because Gastrodia elata has also unacceptable off-odor (swine barnyard-like) for food, there is a need to reduce it as well as allow for greater utilization as a functional food materials. In this study, a major off-odor producing substance of Gastrodia elata was fractionated by steam distillation and silica gel column chromatography. The substance was identified as p-cresol(4-methyl phenol) by GC-MS analysis and comparison of the retention time with that of an authentic compound in GC. The content of p-cresol in fermented Gastrodia elata was decreased. A fermented sample of Latobacillus sakei for 2 days was reduced to 54.7%, when compared with a unfermented sample. The five parishin derivatives in Gastrodia elata were identified by HPLC-MS analyses, and a comparison of HPLC retention times with those of authentic compounds. When compared with parishin derivatives of an unfermented Gastrodia elata, those of Gastrodia elata fermented by L. sakei, increased to 18.3% for 2 days. Increases of about 14.0~38.4% of the total phenolic compounds and 57.4~77.3% total flavonoids were found in fermented extracts, by 3 lactic acid bacteria strains. They were compared with $97.1{\pm}2.9{\mu}g/g$ and $40.9{\pm}2.0{\mu}g/g$ in the unfermented control, respectively. The extracts of Gastrodia elata Blume that were fermented by lactic acid bacteria had higher DPPH free radical scavenging activity and FRAP reducing power than the unfermented control.