• Title/Summary/Keyword: beta-hydroxy acid

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Correlation of Lipid Soluble Compounds of Colored Rices and its Mutagenicity, Antimutagenicity and Antioxidativity (유색미 지용성 성분들의 변이원성.항변이원성.항산화 효과에 대한 상관관계)

  • Shin, Su-Young;Kang, Mi-Young;Nam, Seok-Hyun
    • Applied Biological Chemistry
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    • v.46 no.3
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    • pp.214-219
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    • 2003
  • The fractions extracted with methylene chloride from colored rice seeds of 19 cultivars were prepared to examine the correlationties of both antimutagenicity and antioxidiativity with physiological functionalities. The data revealed a positive correlation of the antimutagenicity with the content of $(3.{\beta},22Z)-Acetate-stigmasta-5,22-dien-3-ol$, 24-Oxocholesterol acetate, 6(E),8(E)-Heptadiene, and Eicosane. For antioxidativity, electron donating ability to DPPH radicals exhibited a positive correlation with the content of (24R,25S)-Aplysterylacetate, however, negative correlations were found between scavenging activity toward hydroxyl radicals and the content of either Tetradecanoic acid or Methyl ester-hexadecanoic acid, $(3.{\beta},24S)-Stigmast-5-en-3-ol$, respectively. In addition, a positive correlation was detected between the inhibitory effect of the fractions and the content of $(3.{\beta},24S)-Stigmast-5-en-3-ol$, however, a negative correlation with the content of 3',3'-Dimethylspiro [acridane-9,1'-indane], $(3.{\beta})-24-Methylene-9,19-cyclolanostan-3-ol$, and some other compounds was observed, respectively.

D-Methionine and 2-hydroxy-4-methylthiobutanoic acid i alter beta-casein, proteins and metabolites linked in milk protein synthesis in bovine mammary epithelial cells

  • Seung-Woo, Jeon;Jay Ronel V., Conejos;Jae-Sung, Lee;Sang-Hoon, Keum;Hong-Gu, Lee
    • Journal of Animal Science and Technology
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    • v.64 no.3
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    • pp.481-499
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    • 2022
  • This study aims to determine the effects of D-methionine (D-Met) isomer and the methionine precursor 2-hydroxy-4-methylthiobutanoic acid i (HMBi) supplementation on milk protein synthesis on immortalized bovine mammary epithelial cell (MAC-T). MAC-T cells were seeded using 10-cm dishes and cultured in Dulbecco's modified Eagle's medium/F12 (DMEM/F12) basic medium. The basic medium of DMEM/F12 was replaced with the lactogenic DMEM/ F12 differentiation medium when 90% of MAC-T cells reached confluency. The best dosage at 0.6 mM of D-Met and HMBi and incubation time at 72 h were used uniformly for all treatments. Each treatment was replicated six times wherein treatments were randomly assigned in a 6-well plate. Cell, medium, and total protein were determined using a bicinchoninic acid protein assay kit. Genes, proteomics and metabolomics analyses were also done to determine the mechanism of the milk protein synthesis pathway. Data were analyzed by two-way analysis of variance (ANOVA) with supplement type and plate as fixed effects. The least significant difference test was used to evaluate the differences among treatments. The HMBi treatment group had the highest beta-casein and S6 kinase beta-1 (S6K1) mRNA gene expression levels. HMBi and D-Met treatments have higher gene expressions compared to the control group. In terms of medium protein content, HMBi had a higher medium protein quantity than the control although not significantly different from the D-Met group. HMBi supplementation stimulated the production of eukaryotic translation initiation factor 3 subunit protein essential for protein translation initiation resulting in higher medium protein synthesis in the HMBi group than in the control group. The protein pathway analysis results showed that the D-Met group stimulated fructose-galactose metabolism, glycolysis pathway, phosphoinositide 3 kinase, and pyruvate metabolism. The HMBi group stimulated the pentose phosphate and glycolysis pathways. Metabolite analysis revealed that the D-Met treatment group increased seven metabolites and decreased uridine monophosphate (UMP) production. HMBi supplementation increased the production of three metabolites and decreased UMP and N-acetyl-L-glutamate production. Taken together, D-Met and HMBi supplementation are effective in stimulating milk protein synthesis in MAC-T cells by genes, proteins, and metabolites stimulation linked to milk protein synthesis.

Anti-complement Activity of Triterpenoids from the Whole Plant of Patrinia saniculaefolia

  • An, Ren-Bo;Na, Min-Kyun;Min, Byung-Sun;Lee, Hyeong-Kyu;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.14 no.4
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    • pp.249-253
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    • 2008
  • Two oleanane-type triterpenes (1, 2) and their glycosides (4-6), and one ursane-type triterpene (3) have been isolated from a methanolic extract of Patrinia saniculaefolia Hemsley (Valerianaceae) through repeated silica gel and reversed-phase C-18 column chromatography. Their chemical structures were determined as oleanolic acid (1), oleanonic acid (2), 23-hydroxyursolic acid (3), 3-O-${\alpha}$-L-arabinopyranosyl-oleanolic acid (4), 3-O-${\beta}$-D-glucopyranosyl-oleanolic acid (5), and oleanolic acid 3-O-[${\alpha}$-D-xylopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucuronopyranoside-6-O-butyl-ester] (6) on the basis of their MS, $^1H$-, and $^{13}C$-NMR spectral data. All compounds were isolated from the whole plant of the P. saniculaefolia for the first time. These compounds were examined for their anti-complement activity against the classical pathway of the complement system. Among them, compounds 1 - 3 exhibited anti-complement activity with $IC_{50}$ values of 470.1, 212.2, and 121.0 ${\mu}M$, respectively, whereas compounds 4 - 6 were inactive. These results suggest that the carbonyl or hydroxy group at C-3 in the oleananeand/or ursane-triterpenes are important for the anti-complement activity against the classical pathway.

Triterpenes from Perilla frutescens var. acuta and Their Cytotoxic Activity

  • Woo, Kyeong Wan;Han, Ji Young;Choi, Sang Un;Kim, Ki Hyun;Lee, Kang Ro
    • Natural Product Sciences
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    • v.20 no.2
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    • pp.71-75
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    • 2014
  • Nine triterpenes were isolated from the petroleum ether and MeOH extract of Perilla frutescens var. acuta leaves. Their structures were determined to be arjunic acid (1), maslinic acid (2), oleanolic acid (3), euscaphic acid (4), tormentic acid (5), 3-O-trans-p-coumaroyltormentic acid (6), 28-formyloxy-$3{\beta}$-hydroxy-urs-12-ene (7), ursolic acid (8), and corosolic acid (9) by spectroscopic methods. The compounds 1, 2, 4, 6, and 7 were isolated for the first time from this plant and the Genus Labiatae. The isolated compounds (1-9) were tested for cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) in vitro using a Sulforhodamin B bioassay.

The Stereospecific Synthesis of Abscisic Acid

  • Park, Oee-Sook;Lee, W.Y.;Park, J.C.
    • Korean Journal of Pharmacognosy
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    • v.17 no.1
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    • pp.67-72
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    • 1986
  • A stereospecific synthesis of 3-methyl-5-(1-hydroxy-4-oxo-2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2,4-pentadienoic acid (abscisic acid) from ${\alpha}-ionone$ has been investigated. Ethyl 5-(2,6,6-trimetyl-2-cyclohexen-1-yl)-trans-4-penten-2-ynoate $({\alpha},{\beta}-acetylenic\;ester)$, which was synthesized from alpha-ionone in two steps, was stereospecifically converted in good yield into ethyl 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2, 4-pentadienoate $({\alpha}-ionylideneacetate)$ by the conjugate addition of lithium dimethylcuprate at $-78^{\circ}C$. Basic hydrolysis of the ethyl ${\alpha}-ionylideneacetate$ gave an abscisic acid precursor, 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2,4-pentadienoic acid, which can be oxidized to yield abscisic acid.

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Isolation and Structural Determination of Free Radical Scavenging Compounds from Korean Fermented Red Pepper Paste (Kochujang)

  • Chung, Jin-Ho;Shin, Heung-Chule;Cho, Jeong-Yong;Kang, Seong-Koo;Lee, Hyoung-Jae;Shin, Soo-Cheol;Park, Keun-Hyung;Moon, Jae-Hak
    • Food Science and Biotechnology
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    • v.18 no.2
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    • pp.463-470
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    • 2009
  • Sixteen antioxidative active compounds isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste, were structurally elucidated as fumaric acid, methyl succinate, succinic acid furan-2-yl ester methyl ester (gochujangate, a novel compound), 2-hydroxy-3-phenylpropanoic acid, 3,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 6,7-dihydroxy-2H-chromen-2-one (esculetin), caffeic acid, cis-p-coumaric acid, trans-p-coumaric acid, daidzin, genistin, apigenin 7-O-$\beta$-D-apiofuranosyl($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, apigenin 7-O-$\beta$-Dglucopyranoside, and quercetin 3-O-$\alpha$-L-rhamnopyranoside by mass spectrometry (MS) and nuclear magnetic resonance (NMR) experiments. These compounds were analyzed for the first time as antioxidants from kochujang.

Physiological Activity and Effects on Lipid Peroxidation of Hot Water-Extract Obtained from Euonymus alatus in Cultured Rat Hepatocyte (Rat의 hepatocyte에서 $amyloid-{\beta$}$로 유발된 세포사, 지질과산화 및 세포산화에 대한 귀전우 열수 추출물의 보호효과)

  • Soo-Sung, Kim;Jong-Dae, Kim
    • The Journal of Korean Medicine
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    • v.22 no.2
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    • pp.53-63
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    • 2001
  • This study was carried out to investigate the physiological activityof the water extract from EA. The present study was done to investigate the effects of EA on cultured hepatocyte cell system and lipid peroxidation in $A{\beta}$ treatment conditions. Pretreatment of EA attenuated in cell cytotoxicity enhanced by increasing concentrations of $A{\beta}$. MDA level induced by $A{\beta}$ treatment was significantly increased and the level was slightly reduced by pretreatment of EA. The ability of EA to reduce cell death and MDA level induced by $A{\beta}$ suggest that EA may be a protective agent against free radical generating compounds such as $A{\beta}$. EA exhibited anti oxidative activity at all concentration tested.The extract was as good as antioxidative activity of the synthetic antioxidants, butylated hydroxy toluene and ascorbic acid. Furthermore, this was superior to that of natural antioxidant, a-tocopherol. In the presence of heavy metal ions ($Fe^{2+},{\;}Zn^{2+}$), EA showed strong antioxidative activity. The extracts showed about 3075% in the nitrite scavenging effect under pH 1.2 and $37^{\circ}C$ for 1 hr. There was significant difference among concentration of extracts.

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Long-term supplementation with a combination of beta-hydroxy-beta-methylbutyrate, arginine, and glutamine for pressure ulcer in sedentary older adults: a retrospective matched case-control study

  • Igor Kisil;Yuri Gimelfarb
    • Journal of Yeungnam Medical Science
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    • v.40 no.4
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    • pp.364-372
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    • 2023
  • Background: Growing evidence suggests that beta-hydroxy-beta-methylbutyrate (HMB), arginine (Arg), and glutamine (Gln) positively affect wound recovery. This study investigated the effects of long-term administration of HMB/Arg/Gln on pressure ulcer (PU) healing in sedentary older adults admitted to geriatric and rehabilitation care facilities. Methods: This was a pilot retrospective case (standard of care and HMB/Arg/Gln)-control (standard of care alone) clinical study. Outcome measures were relative healing rates and Pressure Ulcer Scale for Healing (PUSH) scores (calculated after 4, 8, 12, 16, and 20 weeks) and time to healing. Results: The study subpopulation was comprised of 14 participants (four males, 28.6%) with the median age of 85.5 years (interquartile range [IQR], 82.0-90.2 years). The control subpopulation was comprised of 31 participants (18 males, 58.1%) with the median age of 84.0 years (IQR, 78.0-90.0 years). At the beginning of follow-up, there were no statistically significant demographic (sex and age) and clinical (main diagnosis, baseline area, and PU perimeter) differences between the groups. During the study period, there were no significant differences in the relative healing rates and PUSH scores between the subpopulations. The median time to complete healing in the study and control populations was 170.0 days (95% confidence interval [CI], 85.7-254.3) and 218.0 days (95% CI, 149.2- 286.7) (log-rank, chi-square=3.99; p<0.046), respectively. Conclusion: More than 20 weeks of HMB/Arg/Gln supplementation had a positive effect on difficult PU healing in older adults with multiple comorbidities.

ent-Kaurane- and ent-Pimarane-Type Diterpenoids from Siegesbeckia pubescens and Their Cytotoxicity in Caki Cells

  • Lee Sanghyun;Noh Eun Jung;Kim Jung Sook;Son Eun Mi;Pan Xu;Kim Yeong Shik;Kim Bak-Kwang;Lee Burm-Jong
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.50 no.2
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    • pp.147-150
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    • 2005
  • ent-Kaurane- and ent-pimarane-type diterpenoids were isolated from the methanol extract of Siegesbeckia pubescens by column chromatography. Their structures were elucidated as ent-16$\alpha$H,17-hydroxy-kau­ran-19-oic acid (1), ent-4,17-dihydroxy-16$\alpha$-methyl-kau­ran-19-oic acid (2), ent-16$\beta$,17-dihydroxy-kauran-19-oic acid (3), kirenol (4) and ent-16$\beta$,17,18-trihydroxy-kauran­19-oic acid (5) by spectral analysis. The cytotoxicity of these compounds in Caki cells was assayed by a cell counting kit. Only one group treated with kirenol (4), an entpimarane-type diterpenoid, showed the inhibition of the cell growth in Caki cells.

Chemical constituents from the whole plants of Euphorbia supina Rafin (애기땅빈대의 화학적 성분)

  • An, Ren-Bo;Kwon, Ji-Wung;Kwon, Tae-Oh;Chung, Wan-Tae;Lee, Hye-Suk;Kim, Youn-Chul
    • Korean Journal of Pharmacognosy
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    • v.38 no.3 s.150
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    • pp.291-295
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    • 2007
  • Eight compounds were isolated from the whole plants of Euphorbia supina (Euphorbiaceae) through repeated silica gel, YMC gel and Sephadex LH-20 column chromatography. Their chemical structures were elucidated as 7-hydroxy-6-methoxycoumarin (scopoletin) (1), p-hydroxybenzaldehyde (2), methyl gallate (3), gallic acid (4), quercetin (5), quercetin $3-O-{\alpha}-L-arabinofuranoside$ (avicularin) (6), kaempferol $3-O-{\alpha}-L-arabinofuranoside$ (juglanin) (7) and kaempferol $3-O-{\beta}-D-glucopyranoside$ (astragaline) (8) by spectroscopic (NMR and MS) analysis.