• Title/Summary/Keyword: 2,3-dihydro-3,5-dihydroxy-6methyl-4(H)-pyran-4-one

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Changes in Fructosazines and Major Volatile Components of Burley Leaf Tobacco Extracts by Heat Treatment (버어리잎담배 추출물의 열처리에 의한 화학성분 변화)

  • 이재곤;곽재진;장희진;김옥찬
    • Journal of the Korean Society of Tobacco Science
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    • v.19 no.2
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    • pp.151-158
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    • 1997
  • Burley leaf tobacco extracts has been heated at loot for 2 hours and changes in non-volatile fructosazines and volatile components were investigated. Major changes for the heat treatment with corn syrup of burley leaf tobacco extracts were as follows, increases in the contents of 2,5-deoxyfructosazine and 2,5-fructosazine that is produce for the heating reaction of sugar and ammonia, production of pyraEine compounds, such as 2,6-dimethyl pyrazine,2,4-dimethyl pyrazine, ethrnyl pyrazine, methylethyl pyraxine, trimethyl pyrazine, 2-ethenyl-5-methyl pyrazine, 2-acetyl parazine and 2-acetyl-3-methyl pyrazine, increases in the content of furfuryl alcohol derived from sugar degrad ation, production of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one derived from thermal degradation of Amadori compounds.

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Isolation and Identification of an Antioxidant Substance from Heated Onion (Allium cepa L.) (열처리 양파로부터 항산화물질의 분리동정)

  • Hwang, In-Guk;Kim, Hyun-Young;Lee, Sang-Hoon;Hwang, Cho-Rong;Oh, Seung-Hee;Woo, Koan-Sik;Kim, Dae-Joong;Lee, Jun-Soo;Jeong, Heon-Sang
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.40 no.3
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    • pp.470-474
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    • 2011
  • The objectives of this study were to identify antioxidant substance in heated onion. The isolation of active compound was performed in three steps: silica gel column chromatography, preparative TLC, and preparative HPLC. The structure of the purified compound was determined using spectroscopic methods, i.e., ultraviolet, mass spectrometry, $^1H$-NMR, $^{13}C$-NMR, and DEPT. The antioxidant activities of isolated compound were evaluated and compared with $\alpha$-tocopherol, ascorbic acid, and butylated hydroxytoluene (BHT) using DPPH and ABTS assay. The isolated compound was identified as 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one(DDMP). The DPPH radical-scavenging activity ($IC_{50}$) of the DDMP was in the following order: ascorbic acid (45.3 ${\mu}g/mL$)>$\alpha$-tocopherol (69.2 ${\mu}g/mL$)>DDMP (241.6 ${\mu}g/mL$)>BHT (268.0 ${\mu}g/mL$). In addition, DDMP showed strong ABTS radical-scavenging activity of 569.0 mg AA eq/g.

Isolation and Identification of the Antioxidant DDMP from Heated Pear (Pyrus pyrifolia Nakai)

  • Hwang, In Guk;Kim, Hyun Young;Woo, Koan Sik;Lee, Sang Hoon;Lee, Junsoo;Jeong, Heon Sang
    • Preventive Nutrition and Food Science
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    • v.18 no.1
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    • pp.76-79
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    • 2013
  • We evaluated antioxidant activities of heated pear juice (HPJ) exposed to 120, 130, and $140^{\circ}C$ for 2 hr. HPJ was partitioned using n-hexane, chloroform, ethyl acetate, n-butanol, and water. The ethyl acetate fraction treated at $130^{\circ}C$ for 2 hr showed strong antioxidant activity; thus, this extract was isolated and purified using silica gel column chromatography and preparative high performance liquid chromatography. The structure of the purified compound was determined using ultraviolet and mass spectrometry, $^1H$-nucelar magnetic resonance (NMR), and $^{13}C$-NMR. Antioxidant activities of the isolated compound were evaluated and compared with ${\alpha}$-tocopherol, ascorbic acid, and butylated hydroxytoluene (BHT) using DPPH and ABTS assays. The isolated compound was identified as 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP). The DPPH radical-scavenging activity ($IC_{50}$) of DDMP occurred in the following order: ascorbic acid ($45.3{\mu}g/mL$) > ${\alpha}$-tocopherol ($69.2{\mu}g/mL$) > DDMP ($241.6{\mu}g/mL$) > BHT ($268.0{\mu}g/mL$). Furthermore, DDMP showed strong ABTS radical-scavenging activity (569.0 mg AA eq/g).

Elution Profiles of Volatile Compounds and Free Amino Acids during Alcohol Soaking of Garlic(Allum sativum L.) (마늘의 alcohol 침지 중 휘발성 향기성분과 침출유리아미노산 함량)

  • Lee, Young-Guen
    • Journal of Life Science
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    • v.17 no.2 s.82
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    • pp.286-292
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    • 2007
  • Free amino acids and volatile compounds of fresh garlic and its liqueur were investigated to search elution profile of those components as basic data for development of garlic liqueur. The garlic was soaked in 20% alcohol solution and then sampled every week for 5 weeks. The major free amino acids were L-aspartic acid, L-glutamic acid, L-arginine, L-alanine, L-proline, L-asparagine and L-serine. Neutral amino acids such as L-threonine, L-proline, L-valine and L-leucine, and aromatic amino acids such as tyrosine and phenylalanine were eluted over 80% of those content in fresh garlic after 3 weeks of soaking, but acidic, basic and sulfur containing amino acids were below 80% even after 5 weeks. Sulfide compounds such as diallyl trisulfide, diallyl disulfide, methyl allyl disulfide, 2-vinyl-4H-1,3-dithi in, 3-vinyl-3,4-dihydro-1,2-dithiin, 3,5-diethyl-1,24-trithiolane, isobutyl isothiocyanate and diallyl sulfide were identified as major volatile compounds of fresh garlic by using GC/MS. Among volatile compounds of fresh garlic, allyl alcohol, diallyl disulfide, 3,5-diethyl-1,2,4-trithiolane, diallyl trisulfide and 3,4-dimethoxy furan were eluted to liqueur, but those compounds except 3,5-diethyl-1,2,4-trithiolane were lowered in liqueur during soaking. Furfural, 5-methylfurfural, 5-hydroxymethylfurfural, dimethyl pyrazine, furfuryl alcohol, 3-hydroxy-2-bytanone and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyr-an-4-one were generated newly and their content increased in liqueur during soaking.

Study of Reaction Products and Color Changes in Glutamine-Glucose Model System during Heating (Glutamine-Glucose Model System에서 가열조건별 반응생성물과 색의 변화)

  • Lee, Young-Guen
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.35 no.7
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    • pp.881-885
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    • 2006
  • The product formation and changes in color of glucose/glutamine model system were investigated in relation to heating temperature and time. The mixtures of glucose and glutamine in equal molar ratio were heated at 125, 150 and $175^{\circ}C$ for 10, 20 and 30 minute, respectively. Acetic acid, butanoic acid, 2-butenoic acid, di-(2-cthylhexyl)phthalate, 2,3-dihydro-3,5-dihydroxy-6-methly-4H-pyran-4-one and 5-hydroxymethylfurfural were identified as a major compounds, and 1,3-dimethylbenzene, 2-ethylhexanol, furfural, 5-methylfurfural, 2-pyrrolidinone, and 2,6-di(t-butyl)-4-hydroxy-4-methyl-2.5-cyclohexadien-1-one as 6 minor compounds by using GC/MS. The contents of acetic acid, 2-ehylhexanol and 2-pyrrolidinone increased with increased heating temperature and time, whereas the formation of the other 9 compounds increased up th heating conditions of $150^{\circ}C$ for 10 or 20 min or $175^{\circ}C$ for 10 min, and decreased dramatically with heating above those conditions. Color parameter $L^*$ decreased with increasing heating conition, resulting in dark brown color in final products. Changes of redness parameter $a^*$ and yellowness $b^*$ showed similar to those of the contents of 9 compounds mentioned as above.

Comparison of Flavor Compounds in Steamed- and Nonsteamed-Roasted Polygonatum odoratum Roots by Solid-Phase Microextraction (Solid-Phase Microextraction(SPME)을 이용한 둥굴레차의 증자 여부에 따른 향기성분 특성 비교)

  • Park, Nan-Young;Seo, Ji-Hyung;Kim, Young-Hoi;Kwon, Joong-Ho
    • Korean Journal of Food Science and Technology
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    • v.32 no.3
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    • pp.507-512
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    • 2000
  • The headspace flavors of roasted tea, prepared with steamed and nonsteamed polygonatum roots, were absorbed in solid-phase microextraction(SPME) fiber coated with $65\;{\mu}m$ of carbowax/divinylbenzene(CW/DVB) and analysed by GC-MS. The absorption conditions of SPME fiber for equilibrated headspace were selected as $60^{\circ}C$ and 30 min. In a comparison for both samples roasted at $130^{\circ}C$ for 15 min, gas chromatograms showed a similar pattern in overall profiles between steamed and nonsteamed samples before roasting, but some differences were observed in peak characteristics. From 40 separated peaks, 25 compounds were identified with both GC-MS and retention time comparison. The pyrazines including 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, 2-acetyl-1-pyrroline, etc. were higher in their contents in nonsteamed-roasted sample than steamed-roasted one. In particular, steamed-roasted polygonatum showed higher contents of acetic acid(8.17%) and hexanoic acid(5.43%) than the corresponding compounds of nonsteamed-roasted one, 2.40% and 2.00%.

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Studies on the ROS(Reactive Oxygen Species)-Scavenging Activities of DDMP saponins Isolated from Glycine max (L.) Merrill (대두 (Glycine max (L.) merrill.)에서 추출한 DDMP 사포닌의 활성산소종 제거 작용)

  • 조수진;백희준;이상선;정일민;하지희;강주섭;고현철;신인철;이창호
    • Biomolecules & Therapeutics
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    • v.8 no.1
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    • pp.32-37
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    • 2000
  • Recently new soybean saponins with D DMP (2,5-dihydroxy-6-methyl-2,3,- dihydro-4H-pyran-4-one) moiety have been isolated from legumes. The purpose of this study is to characterize ROS scavenging activities of DDMP saponins ($\alpha$g, $\beta$g saponin) isolated from Glycine max (L.) Merrill. The scavenging activity on OH was examined in terms of lipid peroxidation in the rat liver homogenates and the same activity on $O_2$ was also determined in the xanthine-xanthine oxidase system, respectively. Up to 0.25 mg DDMP saponins ($\alpha$g and $\beta$g saponins) did not cause any significant effects on the prevention of lipid peroxidation as compared with the control group. In terms of superoxide scavenging activities, 0.25 and 0.5 mg $\alpha$g saponin inhibits only 2.6% and 5.5% (p<0.05) of the control group, respectively. However, $\alpha$g saponin dose-dependently (p<0.01, r=0.955) inhibits the formation of superoxide radical unto 21.3% of the control group with a maximal dose of 0.5 mg (p<0.01), equivalent to 0.17 units of superoxide dismutase activity.

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A fragmentation database of soyasaponins by liquid chromatography with a photodiode array detector and tandem mass spectrometry

  • Son, Haereon;Mukaiyama, Kyosuke;Omizu, Yohei;Tsukamoto, Chigen
    • Analytical Science and Technology
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    • v.34 no.4
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    • pp.172-179
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    • 2021
  • Oleanane-type triterpenoids exist as secondary metabolites in various plants. In particular, soyasaponin, an oleanane-type triterpenoid, is abundant in the hypocotyl of soybean, one of the most widely cultivated crops in the world. Depending on their chemical structure, soyasaponins are categorized as group A saponins or group DDMP (2,3-dihydro-2,5-dihydroxy-6-methyl-4H-pyran-4-one) saponins. The different soyasaponin chemical structures present different health functionalities and taste characteristics. However, conventional phenotype screening of soybean requires a substantial amount of time for functionality of soyasaponins. Therefore, we attempted to use liquid chromatography with a photodiode array detector and tandem mass spectrometry (LC-PDA/MS/MS) for accurately predicting the phenotype and chemical structure of soyasaponins in the hypocotyl of five common soybean natural mutants. In this method, the aglycones (soyasapogenol A [SS-A] and soyasapogenol B [SS-B]) were detected after acid hydrolysis. These results indicated that the base peak and fragmentation differ depending on the chemical structure of soyasaponin with aglycone. Thus, a fragmentation database can help predict the chemical structure of soyasaponins in soyfoods and plants.

Maillard Reaction Products Formed from D-Glucose-Glycine, System and Their Formation Mechanism (D-Glucose-Glycine 계의 Maillard 반응생성물 및 그 생성기구)

  • KIM Seon-Bong;PARK Yeung-Ho
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.19 no.1
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    • pp.45-51
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    • 1986
  • Equimolar aqueous solutions of D-glucose and glycine were heated at $50^{\circ}C\;and\;95^{\circ}C$ at pH 6.7. The headspace volatiles and the ether extracts from the reaction mixture were analyzed by gas chromatography and gas chromatography-mass spectrometry using a fused silica capillary column. The major components formed were identified as diacetyl, three furfurals, two pyrroles, one furanone, two pyranones and two amides. In order to elucidate the formation mechanisms of the amides formed front amino-carbonyl reaction, two model systems were adopted. N-butylacetamide were formed as major components from diacetyl-butylamine ana glyoxal-butylamine systems, respectively. The results obtained suggest that such ${\alpha}-dicarbonyls$ as 3-deoxy-D-erythro-2,3-hexodiulose and diacetyl generated in the amino-carbonyl reaction react with amino compounds, amides then being formed by cleavage of the C-C bond in the ${\alpha}-dicarbonyls$.

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Evaluation of Lethality by Chemical Marker (Chemical Marker를 이용한 살균도 예측)

  • Choi, Yang-Mun;Kim, Hie-Joon
    • Korean Journal of Food Science and Technology
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    • v.29 no.1
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    • pp.32-37
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    • 1997
  • The rate constants and activation energies for formation of two chemical markers, M-1 and M-2 at sterilization temperatures were determined in a meatball system. Destruction rates for bacterial spores were also determined. The rate constants for M-1 and M-2 formation at $121^{\circ}C$ were 0.03 and 0.28 Abs/min, respectively. The activation energies for M-1 and M-2 were 27.9 and 24.6 Cal/mol. M-2 was formed faster than M-1 and reached a maximum and decreased. M-1 formation continued up to 30 min at $121^{\circ}C$ and 10 min at $131^{\circ}C$, which makes M-1 a more useful chemical marker for high $F_0$ values. The D-values for spores (B. stearothermophilus ATCC 12980) at 111, 114.4, 117.7 and $121^{\circ}C$ were 7.5, 4.5, 1.9 and 0.58 respectively. At temperatures between 111 and $121^{\circ}C$, there was a liner correlation between destruction of the spores and the M-1 formation. It was difficult to get accurate D-value at $126^{\circ}C\;and\;131^{\circ}C$, because almost all spores were dead before temperature at the center of the meatball reached $126^{\circ}C$. These data suggest that the chemical marker should be used to evaluate overprocessing as well as microbial lethality in aseptic processing.

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