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Nguyen D.H.,Catholic University of Daegu | Zhao B.T.,Catholic University of Daegu | Le D.D.,Catholic University of Daegu | Yoon Y.H.,Functional Cereal Crop Research Division | And 5 more authors.
Journal of Agricultural and Food Chemistry | Year: 2016

Two new fatty acid derivatives, echinochlorins A (8) and B (9) and a racemic lignan, (±)-anti-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-acetoxypropen-1-yl]-2-methoxyphenoxy}propan-1,3-diol 3-acetate (1), were isolated from Echinochloa utilis grains, along with six known lignans (2-7) and two fatty acid derivatives (10, 11). Their structures were established by spectroscopic data analyses (IR, UV, HR-FABMS, GC-MS, and 1D and 2D NMR). The configuration of 1 was determined by Mosher's method. Compound 5 displayed potential inhibitory activity on lipopolysaccharide-induced NO production in macrophage RAW 264.7 cells with an IC50 value of 4.8 ± 0.5 μM. These isolated compounds in crude EtOH extract were also quantitated by HPLC. © 2016 American Chemical Society.


Nguyen D.H.,Catholic University of Daegu | Zhao B.T.,Catholic University of Daegu | Le D.D.,Catholic University of Daegu | Kim K.Y.,Kyungpook National University | And 5 more authors.
Natural Product Sciences | Year: 2016

Seven phenolic compounds including p-coumaric acid (1), 4-hydroxybenzoic acid (2), 4-hydroxy-benzaldehyde (3), vanillic acid (4), luteolin (5), acacetin (6), and tricin (7), were isolated from the methylene chloride and ethyl acetate fractions of Echinochloa utilis grains. Compounds (1 - 4, 6) were isolated for the first time from this plant. These compounds were tested for inhibitory activities against LPS-induced NO production in RAW 264.7 cells. Compounds 5 and 6 displayed significant inhibitory effects, with IC50 values of 27.9 ± 2.6 and 14.0 ± 1.1 µM, respectively. The results suggested that E. utilis ethanolic extract may be used as a potential source of anti-inflammatory agents and functional foods for the treatment of allergic diseases. © 2016 Korean Society of Pharmacognosy. All rights reserved.


Woo H.J.,Kyungpook National University | Oh I.T.,Kyungpook National University | Lee J.Y.,Kyungpook National University | Jun D.Y.,Kyungpook National University | And 4 more authors.
Process Biochemistry | Year: 2012

Treatment of human promyelocytic leukemia HL-60 cells with apigeninidin could induce cytotoxicity (IC50 = ∼80 μM), along with apoptotic sub-G1 cells, TUNEL-positive apoptotic DNA fragmentation, activation of the multidomain pro-apoptotic Bcl-2 proteins (Bak and Bax), mitochondrial membrane potential (Δψm) loss, release of mitochondrial cytochrome c and AIF into the cytoplasm, activation of caspase-9, -3, -8, and -7, and cleavage of PARP and lamin B. These induced apoptotic events were accompanied by decrease of Bcl-2 level and increase of Bak and Bax levels. Apigeninidin-induced sub-G1 cells and activation of Bak and Bax were also detected in human acute leukemia Jurkat T cells, but not in Jurkat T cells overexpressing Bcl-2. Pretreatment of HL-60 cells with the pan-caspase inhibitor z-VAD-fmk reduced significantly apigeninidin-induced sub-G1 cells and caspase cascade activation, whereas it failed to suppress Bak and Bax activations, Δψm loss, and release of mitochondrial cytochrome c and AIF. None of FADD and caspase-8 deficiencies affected the sensitivity of Jurkat T cells to apigeninidin-induced cytotoxicity. These results demonstrated that apigeninidin-induced apoptosis was mediated by activation of Bak and Bax, mitochondrial damage and resultant release of not only cytochrome c, causing caspase cascade activation, but also caspase-independent death effector AIF in HL-60 cells. © 2012 Elsevier Ltd.


PubMed | Kyungpook National University, Catholic University of Daegu and Functional Cereal Crop Research Division
Type: Journal Article | Journal: Journal of agricultural and food chemistry | Year: 2016

Two new fatty acid derivatives, echinochlorins A (8) and B (9) and a racemic lignan, ()-anti-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-acetoxypropen-1-yl]-2-methoxyphenoxy}propan-1,3-diol 3-acetate (1), were isolated from Echinochloa utilis grains, along with six known lignans (2-7) and two fatty acid derivatives (10, 11). Their structures were established by spectroscopic data analyses (IR, UV, HR-FABMS, GC-MS, and 1D and 2D NMR). The configuration of 1 was determined by Moshers method. Compound 5 displayed potential inhibitory activity on lipopolysaccharide-induced NO production in macrophage RAW 264.7 cells with an IC50 value of 4.8 0.5 M. These isolated compounds in crude EtOH extract were also quantitated by HPLC.


Hwang I.G.,Chungbuk National University | Kim H.Y.,Chungbuk National University | Woo K.S.,Functional Cereal Crop Research Division | Lee J.,Chungbuk National University | Jeong H.S.,Chungbuk National University
Food Chemistry | Year: 2011

The various biological activities of Maillard reaction products (MRPs) from sugar (fructose and glucose) and 20 amino acid model systems were evaluated. Colour development, in vitro antioxidant, α-glucosidase inhibitory, antihypertensive, and antiproliferative activities of aqueous solutions of MRPs produced by heating at 130 °C for 2 h were measured. The fructose-amino acid mixture showed higher UV-absorbance and browning intensity than the glucose-amino acid mixture. The fructose-amino acid model MRPs showed higher DPPH and ABTS radical scavenging and ACE inhibitory activities than the glucose-amino acid model MRPs. The α-glucosidase inhibitory effect of MRPs derived from fructose- and glucose-tyrosine showed higher α-glucosidase inhibitory activity than that of other MRPs. Sugar-amino acid model MRPs inhibited the growth of HCT116 colon cancer cell in a dose-dependent manner (from 0.5 to 1.5 mg/ml). Glucose MRPs showed slightly higher antiproliferative activity than fructose MRPs. In particular, sugar-tryptophan and -tyrosine MRPs exerted higher biological activities than the other MRPs. © 2010 Elsevier Ltd. All rights reserved.


Hwang I.G.,Chungbuk National University | Kim H.Y.,Chungbuk National University | Woo K.S.,Functional Cereal Crop Research Division | Hong J.T.,Chungbuk National University | And 4 more authors.
Food Chemistry | Year: 2011

An α-glucosidase inhibitory substance was isolated and characterised from fructose-tyrosine Maillard reaction products (MRPs) and the inhibition mode of the active substance determined. The ethyl acetate fraction of fructose-tyrosine MRPs showed strong α-glucosidase inhibitory activity; this fraction was isolated and purified using silica gel column chromatography and semi-preparative RP-HPLC. The structure of the purified compound was determined using spectroscopic methods. The isolated compound was identified as 2,4-bis (p-hydroxyphenyl)-2-butenal (C16H14O3, HPB242). This is the first report of baker's yeast α-glucosidase inhibitory activity of HPB242 isolated from fructose-tyrosine MRPs. The IC 50 value of HPB242 on α-glucosidase inhibition was 4.00 ± 0.09 μg/ml. Kinetic data revealed that HPB242 inhibits the p-NPG hydrolysing activity of baker's yeast α-glucosidase noncompetitively with a Ki value of 0.870 mM. © 2011 Elsevier Ltd. All rights reserved.

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