• Title/Summary/Keyword: HSQC

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Nuclear Magnetic Resonance (NMR)-Based Quantification on Flavor-Active and Bioactive Compounds and Application for Distinguishment of Chicken Breeds

  • Kim, Hyun Cheol;Yim, Dong-Gyun;Kim, Ji Won;Lee, Dongheon;Jo, Cheorun
    • Food Science of Animal Resources
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    • v.41 no.2
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    • pp.312-323
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    • 2021
  • The purpose of this study was to use 1H nuclear magnetic resonance (1H NMR) to quantify taste-active and bioactive compounds in chicken breasts and thighs from Korean native chicken (KNC) [newly developed KNCs (KNC-A, -C, and -D) and commercial KNC-H] and white-semi broiler (WSB) used in Samgye. Further, each breed was differentiated using multivariate analyses, including a machine learning algorithm designed to use metabolic information from each type of chicken obtained using 1H-13C heteronuclear single quantum coherence (2D NMR). Breast meat from KNC-D chickens were superior to those of conventional KNC-H and WSB chickens in terms of both taste-active and bioactive compounds. In the multivariate analysis, meat portions (breast and thigh) and chicken breeds (KNCs and WSB) could be clearly distinguished based on the outcomes of the principal component analysis and partial least square-discriminant analysis (R2=0.945; Q2=0.901). Based on this, we determined the receiver operating characteristic (ROC) curve for each of these components. AUC analysis identified 10 features which could be consistently applied to distinguish between all KNCs and WSB chickens in both breast (0.988) and thigh (1.000) meat without error. Here, both 1H NMR and 2D NMR could successfully quantify various target metabolites which could be used to distinguish between different chicken breeds based on their metabolic profile.

Isolation of Flavonoids and Lignans from the Stem Wood of Lindera obtusiloba Blume (생강나무(Lindera obtusiloba Blume) 목부로부터 Flavonoid 및 Lignan 화합물의 분리)

  • Seo, Kyeong-Hwa;Baek, Mi-Young;Lee, Dae-Young;Cho, Jin-Gyeong;Kang, Hee-Cheol;Ahn, Eun-Mi;Baek, Nam-In;Lee, Youn-Hyung
    • Journal of Applied Biological Chemistry
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    • v.54 no.3
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    • pp.178-183
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    • 2011
  • The stem woods of Lindera obtusiloba Blume were extracted in 80% aqueous methanol and the concentrated extract was partitioned with ethyl acetate (EtOAc), butanol (n-BuOH), and $H_2O$, successively. From the EtOAc and n-BuOH fractions, five compounds were isolated through the repeated silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies. On the basis of spectroscopic data including mass spectrometry, IR, $^1H$-NMR, $^{13}C$-NMR, distortionless enhancement by polarization transfer, and two-dimensional-NMR gradient correlated spectroscopy (gCOSY), gradient heteronuclear single quantum correlation (gHSQC), gradient heteronuclear multiple bonding connectivity (gHMBC), the chemical structures of the compounds were determined as asarinin (1), (+)-catechin (2), (-)-epicatechin (3), hyperin (4), and nudiposide (5). Compounds 1 and 5 were isolated for the first time from the stem wood of L. obtusiloba Blume.

Alkyl Glycosides from the Flowers of Magnolia obovata (황목련 꽃으로부터 Alkyl Glycoside의 분리 동정)

  • Oh, Eun-Ji;Seo, Kyeong-Hwa;Kwon, Jung-Hwa;Lee, Dae-Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.58 no.3
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    • pp.233-236
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    • 2015
  • The flowers of Magnolia obovata were extracted with aqueous MeOH and fractionated into EtOAc, n-BuOH, and $H_2O$ fractination. Three alkyl glycosides were isolated from the EtOAc fraction through repeated silica gel and ODS column chromatography. The structures were identified to be 2-methylbutan-1-ol-${\beta}$-$\small{D}$-galacto-pyranoside (1), 2-methylbutan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (2), and 2-methylpropan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (3) on the basis of spectroscopic analyses such as fast atom bombardment mass spectrometry, infrared spectroscopy, 1D nuclear magnetic resonance (NMR) ($^1H$ and $^{13}C-NMR$), and 2D NMR (gCOSY, gHSQC, and gHMBC). These compounds were isolated for the first time from the flower of M. obovata in this study.

Degraded Products Induced by Gamma-Irradiation of Mangiferin with Anti-Diabetic Complication Effects (감마선 조사에 의한 Mangiferin 변화물의 항당뇨합병증 활성)

  • Jeong, Gyeong Han;Kim, Tae Hoon
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.46 no.11
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    • pp.1414-1418
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    • 2017
  • Inhibition of advanced glycation end product (AGE) formation is a valuable therapeutic strategy for the regulation of diabetic complications. This study was conducted to identify potential therapeutic targets of anti-diabetic complications from irradiated mangiferin using AGE formation assay. Radiolytic degradation of the xanthone glucoside mangiferin by gamma-irradiation resulted in three degraded mangiferin analogues: mangiferdiol (1), mangiferinol (2), and isomangiferinol (3). Structures of the three newly generated compounds were characterized by interpretation of nuclear magnetic resonance ($^1H$, $^{13}C$ NMR, $^1H-^1H$ COSY, HSQC, HMBC, and NOESY) and mass spectroscopic data. The anti-diabetic complication of the generated mangiferin derivatives were tested using in vitro AGE formation method. Among the tested degraded products, mangiferinol (2) and isomangiferinol (3) exhibited significantly improved potency against AGE formation inhibitory activities with $IC_{50}$ values of $5.6{\pm}0.8$ and $7.6{\pm}0.9{\mu}M$, respectively. This result implies that xanthone derivatives generated from gamma-irradiated mangiferin might be beneficial for prevention of diabetic complication and related diseases.

Structure Determination of the Extractives from the Taxus Cuspidata Fruits (주목열매 추출물 구조분석)

  • Park, Se-Yeong;Choi, In-Gyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.41 no.6
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    • pp.566-575
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    • 2013
  • The fruits of Taxus cuspidata were collected, divided into seeds and fruits, and extracted with 95% EtOH. The extracts were evaporated under the reduced vacuum pressure, concentrated, then successively fractionated with a series of n-hexane, dichloromethane, ethyl acetate and water on a separatory funnel to get some freeze dried samples. A portion of the EtOAc (arils:1.65 g, seeds:1.04 g) and $H_2O$ (arils:7 g, seeds:10 g) soluble samples were chromatographed on a Sephadex column using MeOH-$H_2O$ (1:1, 1:3, 1:5, v/v), EtOH-hexane (3:1, v/v) mixture and 100% $H_2O$ as eluting solvents to isolate pure compounds from the fractions. The isolates were developed by cellulose TLC using t-BuOH-HOAc-$H_2O$ (TBA; 3:1:1, v/v/v) and 6% aqueous HOAc. Visualization was done under ultraviolet light and by spraying the vanillin-HCl-EtOH reagent (4.8:12:480, v/v/v). followed by heating. The structures of the isolates were characterized by $^1H$- and $^{13}C$-NMR, DEPT, 2D-NMR, LC/MS and EI-MS spectra. In addition to the NMR and MS spectra, acid hydrolysis and permethylation were used to determine the correct structure of the isolated sugar compound. Their structures were elucidated as (+)-catechin (1), (-)-epicatechin (2), (+)-gallocatechin (3), (-)-epigallocatechin (4) and ${\beta}$-D-fructofuranose-($2{\rightarrow}4$)-O-${\beta}$-D-glucopyranose($1{\rightarrow}4$)-O-${\alpha}$-D-glucopyranose ($1{\rightarrow}2$)-O-${\beta}$-D-fructofuranose (5) on the basis of the above experimental evidences.

Isolation of 20(S)-Ginsenoside Rg3 and Rg5 from the Puffed Red Ginseng (팽화 홍삼으로부터 20(S)-Ginsenoside Rg3와 Rg5의 분리 및 구조동정)

  • An, Young-Eun;Cho, Jin-Gyeong;Baik, Nam-In;Choi, Sung-Won;Hur, Nam-Yoon;Park, Seok-Jun;Kim, Byung-Yong;Baik, Moo-Yeol
    • Food Engineering Progress
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    • v.14 no.2
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    • pp.159-165
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    • 2010
  • Red ginseng tail roots (9.8 g water/100 g sample) were puffed at 7, 8, 9, and 10 $kg_{f}/cm^{2}$ using a rotational puffing gun. Puffed red ginseng was extracted with 70% ethanol, and the concentrated extract was successively partitioned with diethyl ether, n-butanol and $H_{2}O$. Two unknown ginsenosides from puffed red ginseng were found at 63 and 65 min of retention time in HPLC chromatogram suggesting that chemical structure of some ginsenosides might be altered during the puffing process. Identification of two unknown compounds was carried out using TLC, HPLC and NMR. Two major compounds were isolated from TLC. According to TLC result, compound I was expected to be the mixture of ginsenosides Rk1 and Rg5, and compound II was expected to be a 20(S)-ginsenoside $Rg_{3}$. Three compounds were isolated from n-butanol fraction through repeated silica gel and octadecyl silica gel column chromatographies. From the result of $^{1}H$- and $^{13}C$-NMR data, the chemical structures of unknown compounds were determined as ginsenoside $Rg_{5}$ and 20(S)-ginsenoside $Rg_{3}$. Unfortunately, ginsenoside $Rk_{1}$ could not be separated from ginsenoside-$Rg_{5}$ in the compound I. It was carefully reexamined using HPLC and confirmed that the last unknown compound was ginsenoside-$Rk_{1}$.