• Title/Summary/Keyword: Hydroxy Esters

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Studies on Volatile Flavor Compounds of Soy Sauce Residue (간장박의 휘발성 향기성분에 관한 연구)

  • Cha, Yong-Jun;Wang, Wenfeng;Cha, Ha-Ram
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.45 no.12
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    • pp.1755-1761
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    • 2016
  • Volatile flavor compounds in soy sauce residue (SSR) and acid hydrolysate of SSR (AHSSR) were analyzed by solid phase micro extraction (SPME)/gas chromatography (GC)/mass spectrometry (MSD) methods. A total of 79 compounds were detected in samples (66 SSR and 60 AHSSR). Quantitatively, alcohols (433.37 ng/g), aldehydes (273.01 ng/g), esters (236.80 ng/g), and aromatic hydrocarbons (180.66 ng/g) were dominant in the volatiles of SSR, whereas furans (249.27 ng/g) were only dominant in AHSSR (P<0.05). Among these, four esters, 3-methylbutyl acetate (banana/pear-like), ethyl 3-methyl butanoate (fruity), ethylbenzene acetate (wine-like), and ethyl 3-methyl butanoate (apple-like), three alcohols, 3-methyl-1-butanol (fruity/whisky-like), 2-phenylethanol (floral/sweet), and 1-octen-3-ol (mushroom-like), four aldehydes, (E)-2-phenyl-2-butenal (chocolate-like), benzaldehyde (almond-like), 3-methylbutanal (malty), and 2-phenylacetaldehyde (floral), four aromatic hydrocarbons, 4-ethyl-2-methoxyphenol (smoky/soy sauce-like), 4-ethylphenol (medicine-like), 4-vinyl-2-methoxyphenol (woody), and phenol (woody), and two furans, furfural (almond-like) and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), were major compounds in SSR, whereas seven compounds, including furfural, 5-methylfurfural (almond-like), 3-methyl-1-butanol, 2-phenylethanol, 4-ethyl-2-methoxyphenol, 3-methylbutanal, and benzaldehyde were major compounds in AHSSR.

Chemical Compounds and Volatile Flavor of Rubus coreanum (복분자 열매의 화학성분 및 휘발성 향기성분)

  • 이종원;도재호
    • The Korean Journal of Food And Nutrition
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    • v.13 no.5
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    • pp.453-459
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    • 2000
  • In order to promote the utilization of Rubus coreanum as functional food, and its physicochemical properties and volatile flavor were examined. The contents of chemical compounds showed 5.39% of moisture, 17.3% of total sugars, 8.6% of reducing sugars, 4.5% of crude ash, 3.9% of crude fiber, 10.6% of crude protein and 1.7% of crude fat and that of free sugars was 1.52% of sucrose, 3.98% of fructose, 1.24% of glucose. Among organic acid was 10.2% of citric acid, 6.29% of oxalic acid and 1.94% of malic acid. The highest component of free amino acids was 1,260.3mg of aspartic acid, 1,054.3mg of glutamic acid, respectively. And that of minerals was 38,789ppm of K. A total of 52 volatile flavor components (11 alcohols, 13 acids, 20 carbonyls, 5 hydrocabons, 3 esters) were identified in the Rubus coreanum, respectively. The major volatile flavor components of Rubus coreanum were 3.78% of linalool in alcohols, 14.40% of caproic acid in acids, 2.99% of 2-hydroxy-4-methoxyacetophenone in carbonyls, 1.59% of aromadendrene in hydrocabons and 0.43% of methyl palmitate in esters.

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Fragrance Chemicals in the Essential Oil of Mentha arvensis Reduce Levels of Mental Stress (박하(Mentha arvensis) 향료의 향기성분이 정신적 스트레스 완화에 미치는 효과)

  • Cho, Haeme;Sowndhararajan, Kandhasamy;Jung, Ji-Wook;Jhoo, Jin-Woo;Kim, Songmun
    • Journal of Life Science
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    • v.23 no.7
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    • pp.933-940
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    • 2013
  • The aim of this work was to determine the chemical composition of essential oil from aerial partsof Mentha arvensis L. f. piperascens (MAO) and to evaluate the effect of its fragrant chemicals on electroencephalographic (EEG) activity of human brain. The MAO was obtained by supercritical $CO_2$ extraction. The maximum yield was 2.38% at conditions of $70^{\circ}C$ and 200 bar. There were 32 volatile chemicals with 6 alcohols (67.11%), 13 hydrocarbons (17.05%), 9 esters (11.50%), 2 ketones (7.16%), 1 oxide (2.77%), and 1 aldehyde (0.56%). The major components were (Z,Z,Z)-9,12,15-octadecatrien-1-ol (50.06%), 2-hydroxy-4-methoxyacetophenone (7.50%), and 3,4-dihydro-8-hydroxy-3-methyl-1H-2-benzopyran-1-one (6.60%). Results of the EEG study showed that inhalation of MAO significantly changed the EEG power spectrum values of relative gamma, relative fast alpha, and spectral edge frequency 90%. During the inhalation of MAO, the value of relative fast alpha was significantly increased (p<0.05). On the other hand, the values of gamma and the spectral edge frequency 90% were significantly decreased (p<0.05). The present study suggests that fragrant chemicals of essential oil of M. arvensis reduce the level of mental stress and that they could be used in the treatment of psychophysiological disorders.

Characterization of an alkaline esterase from an enriched metagenomic library derived from an oil-spill area

  • Baek, Seung Cheol;Jo, Jeong Min;Jeong, Soo-Mi;Lee, Jae Pil;Lee, Hyun Woo;Kim, Jungho;Kim, Hoon
    • Journal of Applied Biological Chemistry
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    • v.62 no.1
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    • pp.73-79
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    • 2019
  • A novel esterase gene (est7S) was cloned from an enriched metagenomic library derived from an oil-spill area. The gene encoded a protein of 505 amino acids, and the molecular mass of the Est7S was estimated to be 54,512 Da with no signal peptide. Est7S showed the highest identity of 40% to an esterase from a sludge metagenome compared to the characterized enzymes with their properties, although it showed 99% identity to a carboxylesterase in the genome sequence of Alcanivorax borkumensis SK2. Est7S had catalytic triad residues, Ser183, Glu312, and His420, and the GESAG motif in most family VII lipolytic enzymes. Est7S was purified from the crude extract of clone SM7 using Sephacryl S-200 HR and HiTrap Q column chromatographies. The purified Est7S was optimally active at $50^{\circ}C$ and pH 10.0. Est7S showed a high specific activity of 366.7 U/mg protein. It preferred short length esters, particularly p-nitrophenyl acetate, efficiently hydrolyzed R- and S-enantiomers of methyl-3-hydroxy-2-methylpropionate, and glyceryl tributyrate. These properties of Est7S may provide potential merits in biotechnological applications such as detergent and paper processing under alkaline conditions.

Isolation of Guaianolides with ACAT Inhibitory Activity from the Leaves and Stems of Chrysanthemum boreale Makino (산국의 잎과 줄기에서 ACAT 저해활성을 가지는 Guaianolides의 분리)

  • Lee, Jong Rok;Park, Moon Ki
    • Journal of Environmental Science International
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    • v.26 no.11
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    • pp.1275-1284
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    • 2017
  • Acyltransferase (AT) catalyzes the transfer of an acyl moiety from acyl-coenzyme A (acyl-CoA) to an acceptor. ATs play important roles in the maintenance of homeostasis in the human body and have been linked to various diseases; therefore, several ATs have been proposed as potential targets for the treatment or prevention of such diseases. The AT family includes acyl-CoA:cholesterol AT (ACAT), diacylglycerol AT, and monoacylglycerol AT for the metabolism of lipids. Furthermore, recent molecular biological studies revealed the existence of their isozymes with distinct functions in the body. ACAT plays a critical role in the formation of cholesteryl esters from cholesterol and fatty acids, and is a potential target for treating hypercholesterolemia. During an experiment designed to discover biologically active compounds from herbal medicines, we isolated two known guaianolide sesquiterpene lactones from Chrysanthemum boreale Makino (Compositae). The lactones were characterized from their spectroscopic data (NMR, IR, MASS). These compounds were subjected to ACAT inhibition assay. Here, we report the isolation and structural elucidation of the compounds 8-o-acetyl-2-methoxy-10-hydroxy-3,11(13)-guaiadiene-12,6-olide and 8-acetyl-3,10-hydroxy-4(15),11(13)-guaiadiene-12,6-olide. In the ACAT inhibition assay, compound 1 showed strong inhibitory activity, with an $IC_{50}$ value $45{\mu}g/mL$, whereas compound 2 did not exhibit significant inhibitory activity with an over $100{\mu}g/mL$.

Volatile Flavor Components of Soybean Paste(Doenjang) Prepared from Different Types of Strains (균주를 달리한 된장의 향기 성분)

  • Park, Jung-Suk;Lee, Myung-Yul;Kim, Kyong-Su;Lee, Taik-Soo
    • Korean Journal of Food Science and Technology
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    • v.26 no.3
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    • pp.255-260
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    • 1994
  • Four types of soybean paste(Doenjang), using traditional meju, koji, natto meju and mixture of koji and natto meju, were manufactured and fermented for 90 days. Analyzed volatile flavor components by GC-MS were confirmed to be thirty-six components including 5 alcohols, 5 aldehydes. 8 ketones, 3 acids, 9 esters and 6 miscellaneous ones. Traditional soybean paste tested had 29 components, koji and koji-natto soybean paste $26{\sim}24$ and natto soybean paste had 20 ones. Alcohol was found to be the most abundant volatile flavor components in all samples group. Traditional soybean paste had higher ratio of carbonyl to ester than any other types of soybean paste while koji-natto soybean paste had the lowest ratio of their components. The newly identified five volatile flavor components were 3-ethoxy-l-propene, dihydro-2-methyl-3-furanone. 1-hydroxy-2-propanone, 1-(2-furanyl)ethanone and 2-acethyl ethylhexanoate.

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Studies on the Chemical Constituents of the New Zealand Deer Velvet Antler Cervus elaphus var. scoticus-(I)

  • Lee, Nam Kyung;Shin, Hyun Jung;Kim, Wan Seok;Lee, Jong Tae;Park, Chae Kyu
    • Natural Product Sciences
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    • v.20 no.3
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    • pp.160-169
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    • 2014
  • 44 compounds and 9 minerals were isolated from and detected in the New Zealand deer velvet antler Cervus elaphus var. scoticus L$\ddot{o}$nnberg. The chemical structures of (1 - 26) were identified on the basis of the spectroscopic methods and comparisons with literature, respectively. The structures were identified as cholesterol (CS, 6), 7-keto-CS (7), $7{\beta}$-hydroxy-CS (8), and $7{\alpha}$-hydroxy-CS (9), and included 12 steroid $3{\beta}$-O-(palmitic/stearic/myristic acid esters; PM/SA/MS) [CS-$3{\beta}$-O-PM (1 - 1), CS-$3{\beta}$-O-SA (1 - 2), CS-$3{\beta}$-O-MR (1 - 3), 7-keto-CS-$3{\beta}$-O-PM (2 - 1), 7-keto-CS-$3{\beta}$-O-SA (2 - 2), 7-keto-CS-$3{\beta}$-O-MR (2 - 3), $7{\beta}$-hydroxy-CS-$3{\beta}$-O-SA (3 -1), $7{\beta}$-hydroxy-CS-$3{\beta}$-O-PM (3 - 2), $7{\beta}$-hydroxy-CS-$3{\beta}$-O-MR (3 - 3), $7{\alpha}$-hydroxy-CS-$3{\beta}$-O-SA (4 - 1), $7{\alpha}$-hydroxy-CS-$3{\beta}$-O-PM (4 - 2), and $7{\alpha}$-hydroxy-CS-$3{\beta}$-O-MR (4 - 3)], dinonyl phthalate (5), 8 nucleic acids analogues [uracil (10), deoxyguanosine (11), deoxyuridine (12), uridine (13), deoxyadenosine (14), adenosine (15), inosine (16), and guanosine (17)], and the 9 free amino acids [L-phenylalanine (18), L-isoleucine (19), L-leucine (20), L-tyrosine (21), L-valine (22), L-proline (23), L-threonine (24), L-alanine (25), and L-hydroxyproline (26)]. Also, there are 8 kinds of amino acids [asparagine, serine, glutamine, glycine, histidine, arginine, methionine, and lysine], 2 sialic acids [N-acetylneuraminic acid (27), ketodeoxynonulosonic acid (28)], and 9 minerals [Na > K > Ca > Mg > Fe > Zn > B > Al > Cu] were detected from the autoaminoacid analyzer and ICP spectrometer, HPAEC-PAD/HPLC-FLD, respectively. 9 kinds of oxycholesterol-$3{\beta}$-O-fatty acid ester (2 - 1, 2 - 2, 2 - 3, 3 - 1, 3 - 2, 3 - 3, 4 - 1, 4 - 2, and 4 - 3) and 3 nucleic acids (12, 14, and 15) were isolated from the velvet antler for the first time. 6 kinds of steroids (7, 8, 9, 2 - 1, 3 - 1, and 4 - 1) were examined for their anti-proliferative effects against L1210, P388D1, K562, MEG-01, KG-1, MOLT-4, A549, HepG2, MCF-7, SK-OV-3, and SW-620 cancer cell lines. They showed anti-proliferative effects with $IC_{50}$ values of 0.06, 2.16, 2.42, > 50.0, 1.66 and $8.31{\mu}M$ against L1210, while the values were 24.05, 9.44, 5.22, 0.25. 9.48 and $49.77{\mu}M$ against P388D1, respectively. The others were inactive.

Continuous Surface Treatment and Dyeability of PTT Film via $UV/O_3$ Irradiation (UV/Ozone 조사에 의한 PTT 필름의 연속식 표면처리와 염색성)

  • Jang Jinho;Park Dae Sun
    • Textile Coloration and Finishing
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    • v.17 no.1
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    • pp.7-13
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    • 2005
  • Continuous and intense UV irradiation on PTT film using two types of UV bulbs at different irradiation power level was carried out to modify surface characteristics of the film including zeta potential, wettability, surface energy, and dyeability. ESCA analysis of the irradiated film showed higher O/C ratio than the untreated film indicating photooxidation of outer surface layer. ATR analysis showed that the ester bonds were broken and some new groups were produced such as carboxylic acid, phenolic hydroxy, and other esters, implying that ester bonds of PTT was responsible for the observed photooxidation effect. The surface of the treated PTT film became more hydrophilic and wettable to water, coupled with increased surface energy. Polar component of the surface energy increased and nonpolar component decreased with increasing irradiation energy. The treatment also decreased zeta potential of the modified surface and nanoscale roughness increased with increasing irradiation. The dyeability of the treated films to catonic dyes was significantly improved by electrostatic and polar interaction between dye molecules and the anionic film surface. The UV irradiation seems to be a viable polymer surface modification technology, which has advantages such as no vacuum requirement and continuous process unlike plasma treatment.

Characterization of an Alkaline Family I.4 Lipase from Bacillus sp. W130-35 Isolated from a Tidal Mud Flat with Broad Substrate Specificity

  • Kim, Hee Jung;Jung, Won Kyeong;Lee, Hyun Woo;Yoo, Wanki;Kim, T. Doohun;Kim, Hoon
    • Journal of Microbiology and Biotechnology
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    • v.25 no.12
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    • pp.2024-2033
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    • 2015
  • A gene encoding lipolytic enzyme, lip7-3, was isolated from Bacillus sp. W130-35 isolated from a tidal mud flat. The gene encoded a protein of 215 amino acids with a signal peptide composed of 34 amino acid residues. Lip7-3 belonged to the family I.4 lipase and showed its maximal activity at pH 9.0 and 60℃. Its activity increased in the presence of 30% methanol and, remarkably, increased as well to 154.6% in the presence of Ca2+. Lip7-3 preferred p-nitrophenyl octanoate (C8) as a substrate and exhibited broad specificity for short- to long- chain fatty acid esters. Additionally, Lip7-3 showed a low degree of enantioselectivity for an S-enantiomer (e.g., (S)-methyl-3-hydroxy-2-methylpropionate). It efficiently hydrolyzed glyceryl tributyrate, but did not hydrolyze glyceryl trioleate, fish oil, or olive oil. Its substrate specificity and activation by the solvent might offer a merit to the biotechnological enzyme applications like transesterification in the production of biodiesel.

Synthesis of New Aromatic Ester Plasticizers and Their Endocrine Disrupting Screening (새로운 방향족 에스테르계 가소제 합성 및 내분비계 장애성 시험)

  • Yoo, Kyung-Ho;Ryu, Jae-Chun
    • Journal of the Korean Applied Science and Technology
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    • v.24 no.3
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    • pp.211-218
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    • 2007
  • Based on the Benzoflex (Vesicol Chemical Co.) as PVC plasticizer substituents for Di-n-octyl phthalate (DOP), a series of new aromatic carboxylic acid ester compounds were designed as plasticizers, synthesized, and screened for the endocrine disrupting activity. 2-Hydroxybenzoic acid (1) and 2-methoxybenzoic acid (2) as the commercially available starting materials were reacted with diethylene glycol (3) in the presence of p-toluenesulfonic acid using Dean-Stark column to give diethylene glycol di-(2-hydroxy)benzoate (4, KH01) and diethylene glycol di-(2-methoxy)benzoate (5, KH02), respectively. And diethylene glycol di-(3-pyridinyl) ester (7, KH03) and dipropylene glycol di-(3-pyridinyl) ester (9, KH04) were obtained in high yields by treatment of nicotinoyl chloride (6) with diethylene glycol (3) and dipropylene glycol (8) in the presence of triethylamine as a base. To determine the estrogenic disrupting effect of new synthetic phthalate analogues, E-screen assay method was used. Of these compounds, 4 (KH01) was found to be compound without endocrine disrupting effect.