• Title/Summary/Keyword: furanone

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Anti-melanogenesis effect of 4-hydroxy-5-methyl-3[2H]-furanone, an antioxidant isolated from pine needles (솔잎에서 분리된 항산화 물질인 4-hydroxy-5methyl-3[2H]-furanone의 멜라닌 생성 억제작용)

  • 부용출;전체옥
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.20 no.1
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    • pp.1-13
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    • 1994
  • An antioxidative compound was isolated from pine needles. This compound was identified as 4-hydroxy-5-methyl-3[2H]-furanone on the basis of spectroscopic evidences. It scavenged 1,1-diphenyl-2-picrylhydrazyl free radicals more efficiently than maltol and tocopherol did. It exhibited an inhibitory effect on the lipid peroxidation of rat liver microsome induced by Fe(ll)/ascorbate, and the protective effect against UV cytotoxicity in cultured human fibroblasts. In addition, HMF appeared to prevent the cellular melanogenesis in the cultured murine melanoma cells, more effectively than kojic acid, a well known inhibitor of melanogenesis, while the former was not so effective as the latter for the inhibilion of the tyrosinase. Considering that cellular melanogenesis is a metabolic process triggered by oxidative stress, it was tentatively deduced that the antioxidative property of HMF may afford the effect against cellular pigmentation by alleviating the causative stress. This study provided a novel inhibitor of melanogenesis, that might be useful for the cosmetic applications.

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Actinofuranone C, a New 3-Furanone-Bearing Polyketide from a Dung Beetle-Associated Bacterium

  • Um, Soohyun;Bang, Hea-Son;Shin, Jongheon;Oh, Dong-Chan
    • Natural Product Sciences
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    • v.19 no.1
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    • pp.71-75
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    • 2013
  • Actinofuranone C (1), a new 3-furanone-bearing polyketide, was isolated from an actinobacterium (Amycolatopsis sp.) associated with a female of the dung beetle, Copris tripartitus Waterhouse. The structure of actinofuranone C was elucidated by the spectroscopic interpretation of NMR, mass, UV, and IR data. The discovery of actinofuranone C indicates that chemical investigation of insect-associated microorganisms would be an effective strategy to explore natural chemical diversity.

The Quantitative Changes of Major Compounds from Aster koraiensis Nakai Essential Oil by Harvesting Time (수확 시기에 따른 벌개미취 정유의 주요 화합물 함량 변화)

  • Choi, Hyang-Sook
    • The Korean Journal of Food And Nutrition
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    • v.27 no.2
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    • pp.194-202
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    • 2014
  • This study investigates the chemical compositions of Aster koraiensis Nakai essential oils and the quantitative changes of major terpene compounds according to various harvesting times. The essential oils obtained by hydrodistillation from the aerial parts of Aster koraiensis Nakai are being analyzed by GC and GC-MS. The essential oil compositions of Aster koraiensis Nakai are characterized byhigher contents of sesquiterpene compounds. Ninety-seven volatile flavor compounds are being identified in the essential oils from Aster koraiensis Nakai harvested in 2010, and caryophyllene oxide (8.38%), aristolene (7.08%), epiglobulol (5.57%), and ethyl furanone (4.73%) are the most abundant compounds. Ninety-five compounds are identified in the essential oils from the plants harvested in 2011, and aristolene (11.56%), calarene (9.33%), phytol (8.28%), ethyl furanone (7.63%), and epiglobulol (7.18%) are the most abundant compounds. Ninety-five compounds are being identified in the essential oils from the plants harvested in 2012, and calarene (15.3%), aristolene (14.24%), ethyl furanone (7.21%), phytol (6.98%) are the major compounds. The contents of aristolene, ${\alpha}$-caryophyllene, ${\alpha}$-muurolene, ${\alpha}$-calacorene, aromadendrene oxide, and calarene increase significantly from 2010 to 2012. The contents of ${\alpha}$-cubebene, isocaryophyllene, and diepi-${\alpha}$-cedrene epoxide decrease significantly from 2010 to 2012. The quantitative changes of aristolene and calarene according to harvesting time can be served as a quality index of the Aster koraiensis Nakai essential oils.

Formation of Volatile Compounds from Maillard Reaction of D-Glucose with DL-Alanine in Propylene Glycol Solution (Propylene Glycol 용매계에서 DL-Alanine과 D-Glucose의 마이야르 반응에 의한 휘발성 화합물의 생성)

  • Kim, Young-Hoi;Kim, Ok-Chan;Lee, Jung-Il;Yang, Kwang-Ku
    • Korean Journal of Food Science and Technology
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    • v.20 no.2
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    • pp.157-163
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    • 1988
  • The volatile compounds produced from the browning reaction of 0.5M DL-alanine and 0.5M D-glucose mixture using propylene glycol as a reaction medium were analysed by gas chromatography and gas chromatography-mass spectrometry and effects of temperature($100^{\circ}C,\;120^{\circ}C,\;140^{\circ}C$) and time(20min, 2hours) on the formation of volatile compounds were investigated. Browning reaction were rapidly increased as the reaction temperature and time increased. From methylene chloride extracts, twenty six compounds, including 7 alkyl pyrazines. 4 pyrroles, 3 furans, 1 furanone and 11 miscellaneous compounds were identified. The relative amounts of pyrazines, pyrroles and furans were markedly increased as reaction temperature and time increased. The results showed that caramel-like and burnt sugar-like aroma produced by alanine -glucose reaction must be mainly comprised of nitrogeneous heterocyclic such as pyrazines, pyrroles and oxygen heterocyclic compounds such as 2-hydroxy-3-methyl-2-cyclopenten-1-one and 2,5-dimethyl-4-hydroxy-3(2H)-furanone.

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Modified Synthetic Method & Cytotoxic Activity of Ranunculin and Protoanemonin (Ranunculin및 Protoanemonin의 합성법의 개선 및 세포독성 평가)

  • 방성철;김용;안병준
    • YAKHAK HOEJI
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    • v.48 no.2
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    • pp.117-121
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    • 2004
  • Ranunculin, a potent cytotoxic component of P. koreana, was synthesized by reacting (s)-(-)-5-(hydroxymethyl)-2(5H)-furanone with 2,3,4,6-tetra-O-acetyl-$\alpha$-D-glucopyranosyl bromide and successive removal of the acetyl protecting group by 0.5 M HCl/MeOH. A new deacetylation process of the intermediate tetraacetylranunculin was deviced giving a yield of 83% of ranunculin. Protoanemonin, the cytotoxic structural moiety of ranunculin, was synthesized by dehydration of (s)-(-)-5-hydroxymethyl-2(5H)-furanone. Ranunculin showed a moderate cytototoxic activity against A-549 (ED$_{50}$=7.53 $\mu\textrm{g}$/$m\ell$), NIH3T (ED$_{50}$=13.6$\mu\textrm{g}$/$m\ell$), and SK-OV-3 (ED$_{50}$=17.5 $\mu\textrm{g}$/$m\ell$). Meanwhile, protoanemonin also exhibited moderate cytotoxicity against A-549 (ED$_{50}$=9.38 $\mu\textrm{g}$/$m\ell$), NIH3T (ED$_{50}$=13.8 $\mu\textrm{g}$/$m\ell$), and SK-OV-3 (ED$_{50}$=15.1 $\mu\textrm{g}$/$m\ell$). It was found that both of the synthetic products showed a potenter cytotoxicity against A-549.ainst A-549.

Microflow Photochemistry - Acetone sensitized Addition of Isopropanol to (5R)-5-Menthyloxy-2-(5H)-furanone

  • Aida, Shin;Nishiyama, Yasuhiro;Kakiuchi, Kiyomi;Hoffmann, Norbert;Fon, Adeline;Oelgemoller, Michael
    • Rapid Communication in Photoscience
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    • v.2 no.3
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    • pp.68-71
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    • 2013
  • Acetone sensitized photoadditions of isopropanol to (5R)-5-menthyloxy-2-(5H)-furanone were investigated in two different microflow reactor systems. Setup A employed a commercially available glass reactor under a UVB-panel. Setup B utilized a FEP microcapillary wrapped tightly around a Pyrex cylinder with a single UVB fluorescent tube at its center. The reactions under flow conditions were subsequently compared to analogue reactions conducted in a batch chamber reactor. Overall, the microflow systems gave faster conversions and higher isolated yields. The flexible microcapillary setup, however, showed the best performance and promise in terms of future scale-up and reactor optimization.

Anti-melanogenesis effect of 2,5-dimethyl-4-hydroxy-3 [2H]-furanone

  • Jeon, Che-Ok;Ohf, Ji-Yeon;Koh, Jae-Sook;Jung, Sung-Won;Kim, Jung-Yeon
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.22 no.2
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    • pp.70-75
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    • 1996
  • DMHF (2.5-dimethyl-4-hydroxy-3[2H]-furanone), an antioxidative compound from the reaction of L-cysteine/D-glucose scavenged efficiently 1,1-diphenyl-2-picryl hydrazyl free radicals. It exhibited an inhibitory effect on the autoxidation of linolenic acid, and the protective effect against UV cytotoxicity in cultured human fibroblast. In addition, DMHF appeared to prevent the cellular melanogenesis in the cultured murine melanoma cells more effectively than kojic acid, a well known inhibitor of melanogenesis, while the former was not so effective as the latter for the inhibition of the tyrosinase. Considering that cellular melanogenesis is a metabolic process triggered by oxidative stress, it ovas tentatively deduced that the antioxidative property of DMHF might afford the effect against cellular pigmentation by alleviating the causative stress. In toxicological tests such as irritation and sensitization, this compound turned out to be safe. The results of this study suggest that DMHF may be a novel inhibitor of melanogenesis, and that night be useful for application in cosmetics.

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Volatile Flavor Components of Korean Auricularia polytricha (Mont.) sacc. Mushroom (한국산 털목이버섯의 휘발성 향기성분)

  • Lee, Jae-Gon;Do, Jae-Ho;Sung, Hyun-Soon;Lee, Jong-Won
    • Applied Biological Chemistry
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    • v.38 no.6
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    • pp.546-548
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    • 1995
  • An attempt was made to determine the volatile flavor components of Auricularia polytricha mushroom. Essential oils from the dried mushroom were isolated by a simultaneous steam distillation-extraction(SDE) method using diethyl ether as a solvent. Total 30 components were identified bt GC-MS from the in essential oils including 11 acids, 10 alcohols, 5 aldehydes, 3 ketons, 1 other components. The major volatile components were heaxadecanoic acid(16.74%), benzeneethanol(7.77%), pentadecanoic acid(7.59%), dihydro-5-penhtyl-2-(3H)-furanone acid(4.28%), tetradecanoic acid(3.37%), pentanoic acid(3.38%) and 1-octen-3-ol(1.26%).

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The study of analysis of mutagen in drinking water (음용수 중 변이원성 물질(MX)에 관한 연구)

  • Yoo, Eun-Ah;Won, Jung-In
    • Analytical Science and Technology
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    • v.19 no.4
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    • pp.290-300
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    • 2006
  • Disinfection by-products(DBPs), such as volatile trihalomethanes and the nonvolatile organochlorine acids, created by chlorination have been extensively studied. However MX which contributes 20-50% of the mutagenic activity in drinking water began to people's attention since 1990. Its chemical name is 3-chloro-4-dichloromethyl-5-hydroxy-2(5H)-furanone. According to WHO guidelines its concentration should be controlled, but its value has not been set up. Due to analytical difficulties in measuring this compound at such a low concentrations and lack of information on toxicity to human. Because concentration (ng/L) of MX in drinking water is low traditional testing methods are ineffective. Therefore this study compared LLE and SPE and have chosen SPE to improve preconcentration. MX has been identified in chlorinated drinking water samples in several countries but not in korea Therefore this study analyzed concentration of MX in different water sources and in spring water. This study examined the causes of changing MX content. Chlorine dosage, seasons, water temperature and distance from the source was all discoverd to be relavant. MX was analyzed in various treatment to find optimum disinfection methods. The outcome was that the concentration of MX was minimized when using biological activated carbon-O3 and granular activated carbon.