• Title/Summary/Keyword: Dihydrobenzofuran

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Isolation and Identification of Antimicrobial Compound from UlGeum (Curcuma longa L.) (울금으로부터 식품부패미생물에 대한 항균성 물질의 분리 및 동정)

  • Choi, Hae-Yeon
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.38 no.9
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    • pp.1202-1209
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    • 2009
  • Antimicrobial activity of UlGeum (Curcuma longa L.) was investigated. Methanol extract of dried UlGeum was fractionated to hexane, chloroform, ethyl acetate, butanol and water fraction. The antimicrobial activity of five crude fractions were examined using impregnated paper disk agar diffusion. Ethyl acetate fraction showed the highest inhibitory effect on the microorganisms such as B. subtilis, S. aureus, E. coli, L. monocytogenes and V. parahaemolyticus at 1,000 ${\mu}g$/disc. Ethyl acetate fraction was further fractionated by silica gel column and thin layer chromatography (TLC). The antimicrobial compound was isolated from their fractions and its chemical structure was identified as a 2,3-dihydrobenzofuran by GC-MS and $^1H$-NMR.

Glycosidically Bound Volatile Components in Apricot (Prunus armeniaca var. ansu Max.) (살구에서 배당체의 형태로 존재하는 휘발성 성분)

  • Kim, Young-Hoi;Kim, Kun-Soo;Park, Joon-Young;Kim, Yong-Tae
    • Korean Journal of Food Science and Technology
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    • v.22 no.5
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    • pp.549-554
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    • 1990
  • Glycosidically bound fraction was separated from apricot by Amberlite XAD-2 adsorption and eluted with methanol. Aglycones were liberated from the bound fraction by enzymatic hydrolysis, acid hydrolysis or by means of simultaneous distillation-extraction at pH 3.0. A total of 40 components were identified in three bound volatile fractions. Besides linalool oxide, linalool. ${\alpha}-terpineol$, nerol, geraniol, benzyl alcohol and 2-phenylethyl alcohol, previously reported as glycosidically bound volatiles, the following components were identified for the first time as glycosidically bound volatiles in apricot: 2,6-dimethyl-3,7-octadiene-2,6-diol , 3.7-dimethyl-1,5-octadiene-3,7-diol, (E)- and (Z)-2.6-dimethyl-2,7-octadiene-1,6-diol, $3,4-didehydro-{\beta}-ionol,\;3-oxo-{\alpha}-ionol$, $3-hydroxy-7,8-dihydro-{\beta}-ionol,\;3-oxo-7,8-dihydro-{\alpha}-ionol ,\;3-hydroxy-{\beta}-ionone$, eugenol, 4-hydroxyethylphenyl acetate and 2,3-dihydrobenzofuran.

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Synthesis and Biological Activities of New 5-Substituted Uracil Derivatives (새로운 5-치환 Uracil 유도체의 합성 및 생물활성)

  • Yi, Won-Hui;Park, Jung-Sup;Won, Jeong-Hee;Lee, Chong-Ock;Ryu, Eung-K.
    • YAKHAK HOEJI
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    • v.35 no.6
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    • pp.497-503
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    • 1991
  • Six novel 5-substituted-1-[2-(3-methoxy-2-hydroxyphenyl)-1-methoxyethyl]uracils 2a-f were prepared by condensation of 2,4-bis(trimethylsilyloxy)-5-substituted uracils with 2,7-dimethoxy-2,3-dihydrobenzofuran (9) in the presence of Lewis acid. The 2,3-dihydrobenzofuran derivative 9 was obtained by intramolecular acetalization of 2-acetoxy-3-methoxyphenyl acetaldehyde (8) which was synthesized by oxidative cleavage of 1-allyl-2-acetoxy-3-methoxybenzene (7) using osmium tetroxide followed by $NaIO_4$. Compounds 2a-f were evaluated for in vitro antiviral activity against HSV-1, HSV-2 and HRV. None of these compounds showed activity with $ID_{50}$ values up to $100\;{\mu}g/ml$ except for 5-chlorouracil derivative 2d which exhibited antiviral activity against HSV-1 with $ED_{50}$ $30\;{\mu}g/ml$. In the antitumor activity against L1210 and P388 leukemia cell lines, 2d showed activity with $ID_{50}$ values of $14\;{\mu}g/ml$ and $11.6\;{\mu}g/ml$, and 2c with $ID_{50}$ values of $22.9\;{\mu}g/ml$ and $8.8\;{\mu}g/ml$, respectively.

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Volatile Oil Composition of Boxthorn (Lycium chinense M.) Leaves

  • Ryu, Su-Noh;Kim, Seong-Min
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.43 no.3
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    • pp.189-193
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    • 1998
  • Volatile components were extracted from leaves of two Boxthorn (Lycium chinense M.) cultivars by using simultaneous distillation and extraction, analyzed by gas chromatography-mass spectrometry. Seventy components were identified : 13 acids, 15 alcohols, 18 hydrocarbons, 13 carbonyls, three esters, three ionones, and five others. The principal volatile components (and their peak area percentage) were n-pentanol (11.2~30.2%), phytol (14.5~28.3%), hexadecanoic acid (13.5~17.1%) 2,3-dihydrobenzofuran (1.5~4.2%), benzyl alcohol (1.9-4.8%), phenylacetaldehyde (1.8~3.2%), and octadecadienoic acid (1.7~10.7%). Fresh leaves showed much higher peak area than that of dried leaf in n-pentanol, n-hexanol, cis-2-penten-l-ol, cis-3-hexen-l-ol, benzyl alcohol, and $\beta$-phenylethyl alcohol, while dried leaves showed much higher content than that of fresh leaves in 9-hydroxytheaspran A, octadecanoic acid and octadecadienic acid.

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Lignans from the Stem Barks of Kalopanax septemlobus

  • Hong, Seong-Su;Han, Xiang-Hua;Park, Seon-Soon;Lee, kyong-Soon;Lee, Myung-Koo;Hwang, Bang-Yeon;Ro, Jai-Seup
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.194.3-194.3
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    • 2003
  • As a part of an ongoing collaborative program to discover novel bioactive components of plant origin, the stem barks of Kalopanax septemlobus were extracted with MeOH, and successively partitioned with CH$_2$Cl$_2$, EtOAc, BuOH and water. Repeated column chromatographic separation of the CH$_2$Cl$_2$ fraction resulted in the isolation of four compounds. Their structures were identified as vladinol E (1), (-)-simulanol{4-[3-hydroxymethyl-5-((E)-3-hydroxypropenyl)-7-methoxy-2,3-dihydrobenzofuran-2-yl]-2,6-dimethoxy-phenol} (2), vladinol F (3), and (${\pm}$)-secoisolariciresinol (4). This is the first report on the isolation of these compounds from Kalopanax species.

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Volatile Flavor Components in Cooked Black Rice (취반된 흑미의 휘발성 향기 성분)

  • Song, Seon-Joo;Lee, You-Seok;Rhee, Chong-Ouk
    • Korean Journal of Food Science and Technology
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    • v.32 no.5
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    • pp.1015-1021
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    • 2000
  • Volatile flavor components (VFCs) in cooked black rices (Suwon-415 and Chindo) were studied. The major reactions during cooking, which result in aroma volatiles, are the Maillard reaction between amino acids and reducing sugars, and thermal degradation of lipid. Black rices washed with water were soaked in 1.5 folds water and heated at $110^{\circ}C$ in oil bath for 30min. VFCs in cooked black rices were extracted for three hours by SDE and were analyzed by GC and GC/MS. A total of 91, 82 volatiles were identified in Suwon-415 and Chindo black rice, respectively. Suwon-415 was composed of 26 alcohols, 10 aldehydes, 5 acids, 11 esters, 15 ketones, 9 hydrocarbons, 3 furans, 3 nitrogen containing compounds and 9 sulfur containing compounds. Chindo was composed of 28 alcohols, 9 aldehydes, 4 acids, 12 esters, 14 ketones, 5 hydrocarbons, 3 furans, 3 nitrogen containing compounds and 4 sulfur containing compounds.

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Flavor Components of Artemisia Lavandulaefolia DC (참쑥(Artemisia Lavandulaefolia DC)의 방향성분)

  • Choi, Kyoung-Sook;Choi, Bong-Young;Park, Hyoung-Kook;Kim, Jung-Han;Park, Jong-Sei;Yoon, Chang-No
    • Korean Journal of Food Science and Technology
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    • v.20 no.6
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    • pp.774-779
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    • 1988
  • The essential oil of Artemiisa lavandulaefolia DC was analyzed by gas chromatography/mass spectrometry (GC/MS). The oil was stored at different conditions for 6 weeks and the changes of color and chemical composition during storage were checked by GC/MS. The experimental results were as follows; (1) More than 186 chemicals were detected by GC. Major components were 1,8-cineol, thujone, camphor, borneol, coumarin, 2,3-dihydrobenzofuran and ${\beta}-biasbolene$. In this study, 3,3,6-trimethyl norpinanol, ${\beta}-farnesene,\;{\alpha}-curmene$ and 7-methoxy coumarin were detected as new compounds in Artemisia species. (2) It was proved that temperature and/ or light had and important effect on the changes of color and volatile components of the essential oil. The relative amounts of limonene and 1.8-cineol were decreasad, on the other hand, ${\beta}-phellandrene\;and\;{\alpha}-terpineol$ were increased during storage.

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Changes of Volatile Flavor Compounds of Seibel Grape Must during Alcohol Fermentation and Aging (Seibel 포도즙 알코올 발효 및 저장 중 휘발성 향기성분의 변화)

  • 고경희;장우영
    • Microbiology and Biotechnology Letters
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    • v.27 no.6
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    • pp.491-499
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    • 1999
  • A great variety of the volatile metabolic by-products was formed in yeast cell during alcohol fermentation. The seibel grape (Vitis labrasca) which was grown in the Southern Korea used for wines. The objective of this research was to identify the volatile flavor compounds during alcohol fermentation and aging at 12$^{\circ}C$. saccharomyces cerevisiae and Schizosaccharomyces pombe were inoculated and fermented in seibel grape must. The volatile flavor compounds of logarithmic, stationary and death phases were extracted, concentrated and identified by gas chromatography/mass spectrometer (GC/MS). The volatile flavor compounds were determined by a Hewlett-Packard 5890 II Plus GC which was equipped with Supelcowax 10 fused silica capillary column (60m$\times$0.32mm$\times$0.25${\mu}{\textrm}{m}$ film thickness) wall coated with polyethyleneglycerol. The scan detection method allowed the comparison of the spectrum from the chromatogram of volatile flavor compounds to those in data Wileynbs base library. Among the volatile compounds collected by ether-hexane extraction method, the evolution of 20 main compounds, such as 9 esters (ethyl butyrate, isoamyl acetate, ethyl caproate, n-hexyl acetate, ethl caprylate, ethyl caprate, diethy succinate, ethyl hexadecanoate, 2-pheneethyl acetate), 4 alcohols (3-methyl-1-butanol, 1-hexanol, 1-heptanol, benzoethanol), 4 ketones and acids (2-octanone, caproic acid, caprylic acid, capric acid), 2 furan and phenol (2,6-bis(1,1-dimethyl ethyl)phenol, 2,3-dihydrobenzofuran) were observed during alcohol fermentation and aging. The production of the esters during alcohol fermentation with S. cerevisiae was higher than those of Sch. pombe. The sensory scores of the aged wine samples in aroma, taste and overall acceptability were not significantly different(p<0.05).

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Comparison of Pyrolytic Components in lamina and Midrib of Flue-Cured Tobacco Leaves

  • Lee, Jae-Gon;Jang, Hee-Jin;Kwag, Jae-Jin;Lee, Dong-Wook
    • Journal of the Korean Society of Tobacco Science
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    • v.22 no.2
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    • pp.176-183
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    • 2000
  • This study was conducted to compare the volatile components of lamina(cutter group) and midrib of flue-cured tobacco leaves by two analytical methods, Curie-Point pyrolysis and Purge & Trap headspace technique. The pyrolysis of lamina and midrib part of tobacco leaves was performed at the temperature of $330^{\circ}C$, $650^{\circ}C$, and $920^{\circ}C$ by Curie-Point Pyrolyzer, and 33 compounds were identified in the pyrolyzates by GC/MSD. The composition of the components identified showed a quite difference between lamina and midrib. However, the amount of the pyrolyzed products from the both of lamina and midrib was increased with temperature increase except that of acetic acid, furfural, and nicotine. The content of phenolic compounds including phenol, 4-methyl phenol, and 3-methyl phenol was higher in midrib than in lamina, while that of furan compounds such as 2,3-dihydrobenzofuran, 5-hydroxymethyl furfural, was high in lamina. Interestingly, acetamide, 2-propenamide and 3-acetoxy pyridine were not defected in the pyrolyzates of lamina. By Purge & Trap headspace technique, 28 volatile components were identified in both lamina and midrib. The composition of the identified compounds and their chromatograpic patterns also showed the complete difference between the two. The content of solanone, $\beta$-damascone, $\beta$-damascenone, and megastigmatrienones, key components of tobacco aroma, was much higher in lamina than in midrib. The results indicate that lamina contains much more carbonyl compounds known to enhance the smoke taste of cigarette, whereas midrib takes nitrogenous and phenolic compounds, which are known to cause a deteriorate effect of smoke such as irritation.

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Conditions for Rapid Processing of Modified Fish Sauce using Enzymatic Hydrolysis and Improvement of Product Quality 4. Flavor Components of Fish Sauce from Whole Sardine (효소분해법에 의한 개량어장유의 속성제조 및 품질에 관한 연구 4. 정어리 전어체를 이용한 어장유의 냄새 성분)

  • BAE Tae-Jin;HAN Bong-Ho;CHO Hyun-Duk;KIM Byeong-Sam;LEE Hyun-Suk
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.23 no.5
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    • pp.373-377
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    • 1990
  • Volatile components of whole sardine sauce which was prepared with $7\%$ of complex enzyme-2000($2.18{\cdot}10^4\;U/g solid$), mixed with $6\%$ of invert sugar and heated at $90^{\circ}C$ for 2 hours were compared with those of without invert sugar. Thirty seven kinds were identified from the whole volatile components of hydrolysate heated without invert sugar and fourty three kinds were identified from the hydrolysate heated with $6\%$ of invert sugar. Amines were not detected from the whole volatile components of the chopped whole sardine hydrolysate. Considerable amount of 2,3-dihydrobenzofuran and 2-acetylpyrrole, a little amount of 2,5-hydrofuran, 2-ethylbutanol, 2-pyrone, 2-acetylfuran, 2,6-dimethylpyrazine, 2-acetylpyrazine, 5-methyl-2-furfural, furfuryl acetate, butylpyrrole and 2-methyl-3-hydroxypyrone were detected in the hydrolysate thermally treated with $6\%$ of invert sugar while these were not found in the hydrolysate heated without invert sugar. But the amount of 2-methyt-1-propa-not, hexane, butyl acetate and butyl alcohol were decreased, and acetic acid and butanoic acid were detected as volatile fatty acids.

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