• Title/Summary/Keyword: 5-hydroxy-2-methyl-1

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Isolation and Identification of Bioactive Compounds from the Tuber of Brassica oleracea var. gongylodes

  • Prajapati, Ritu;Seong, Su Hui;Kim, Hyeung Rak;Jung, Hyun Ah;Choi, Jae Sue
    • Natural Product Sciences
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    • v.26 no.3
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    • pp.214-220
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    • 2020
  • Brassica oleracea var. gongylodes (red kohlrabi) is a biennial herbaceous vegetable whose edible bulbotuber-like stem and leaves are consumed globally. Sliced red kohlrabi tubers were extracted using methanol and the concentrated extract was partitioned successively with dichloromethane (CH2Cl2), ethyl acetate (EtOAc), n-butanol (n-BuOH) and water (H2O). Repeated column chromatography of EtOAc fraction through silica, sephadex LH-20 and RP-18 gel led to isolation of eleven compounds of which compound 1 was a new glycosylated indole alkaloid derivative, 1-methoxyindole 3-carboxylic acid 6-O-β-D-glucopyranoside. Others were known compounds namely, β-sitosterol glucoside (4), 5-hydroxymethyl-2-furaldehyde (5), methyl-1-thio-β-D-glucopyranosyl disulfide (6), 5-hydroxy-2-pyridinemethanol (7), (3S,4R)-2-deoxyribonolactone (8), n-butyl-β-D-fructopyranoside (9), uridine (10) and three fructose derivatives, D-tagatose (11), β-D-fructofuranose (12) and β-D-fructopyranose (13). Similarly, isolation from CH2Cl2 fraction gave two known indole alkaloids, indole 3-acetonitrile (2) and N-methoxyindole 3-acetonitrile (3). The structure elucidation and identification of these compounds were conducted with the help of 13C and 1H NMR, HMBC, HMQC, EIMS, HR-ESIMS and IR spectroscopic data, and TLC plate spots visualization. Compounds 2, 3, 4, 5, 6, 7, 8 and 9 are noted to occur in kohlrabi for the first time. Different bioactivities of these isolated compounds have been reported in literature.

Flame-retardant Coating of Cotton Fabric via UV curing of DMEP

  • Jang, Jin-Ho;Kim, Young-Min;Jeong, Yong-Kyun;Nam, Young Sik
    • Textile Coloration and Finishing
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    • v.19 no.5
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    • pp.1-7
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    • 2007
  • A new UV-curable coating was carried out to impart the flame-retardant property to cotton fabric using Bis[2-(methacryloyloxy)ehtyl]phosphate(DMEP) and 2-hydroxy-2-methyl-1-phenyl-propan-l-one(HMPP) as a UV-curable monomer and a photoinitiator, respectively. The cotton fabrics were applied with various amounts of DMEP and HMPP via padding and UV irradiation, and the optimal concentrations of DMEP and HMPP in the formulation were 40%(w/w) and 7%omp respectively. A limiteed oxygen index(LOI) up to 28.9 was obtained for the UV-cured fabric, which may occur through a condensed phase mechanism as verified by the increased residue number with increased application level. The characterization of the UV-cured coating was made by IR analysis, thermo-gravimetric analysis, LOI test, and scanning electron microscopy.

Formation of Furans during the Acid Hydrolysis of Agar and Their Removal by Treatments of Lime, Steam-stripping and Hydrophobic Resins (한천의 산 당화에 의한 Furan화합물의 생성 및 제거)

  • Kim, Na-Hyun;Lee, Jae-Won;Seo, Yung-Bum;Yoon, Min-Ho
    • Korean Journal of Agricultural Science
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    • v.36 no.2
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    • pp.225-232
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    • 2009
  • The ratio of saccharification and formation of furans during the acid hydrolysis of agar with oxalic acid and sulfuric acid were examined base on the contents of the agar and acids. The ratio of saccharification in oxalic acid appeared to be 51~59% somewhat higher than 49~61% of sulfuric acid. Formation of the furans during the acid hydrolysis increased proportional to the contents of agar and acid. The relative formation ratio was high 10~47% for furfural (FUR) and 15~29% for hydroxy-methyl furfural (HMF) in 0.5~1.25% sulfuric acid rather than those of oxalic acid. When comparing the removal efficiency of the furans using an alkali treatment, steam stripping and hydrophobic resins, FUR was eliminated 60% by the alkali treatment, 62~90% by steam stripping and 71~75% by Amberlite XAD4 and 7HP, while HMF was removed to low levels of 10.5%, 4~17% and 13~25%, respectively. The loss of reducing sugar was also observed in process of the removal of furans, and the loss rate was the level of 2~4% in alkali treatment, 11~16% in steam stripping and 7~9% in Amberlite resins.

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Vitamin B6 Deficiency, Genome Instability and Cancer

  • Wu, Xia-Yu;Lu, Lin
    • Asian Pacific Journal of Cancer Prevention
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    • v.13 no.11
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    • pp.5333-5338
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    • 2012
  • Vitamin B6 functions as a coenzyme in >140 enzymatic reactions involved in the metabolism of amino acids, carbohydrates, neurotransmitters, and lipids. It comprises a group of three related 3-hydroxy-2-methyl-pyrimidine derivatives: pyridoxine (PN), pyridoxal (PL), pyridoxamine (PM) and their phosphorylated derivatives [pyridoxal 5'-phosphate (PLP) and pyridoxamine 5'-phosphate (PMP)], In the folate metabolism pathway, PLP is a cofactor for the mitochondrial and cytoplasmic isozymes of serine hydroxymethyltransferase (SHMT2 and SHMT1), the P-protein of the glycine cleavage system, cystathionine ${\beta}$-synthase (CBS) and ${\gamma}$-cystathionase, and betaine hydroxymethyltransferase (BHMT), all of which contribute to homocysteine metabolism either through folate-mediated one-carbon metabolism or the transsulfuration pathway. Folate cofactors carry and chemically activate single carbons for the synthesis of purines, thymidylate and methionine. So the evidence indicates that vitamin B6 plays an important role in maintenance of the genome, epigenetic stability and homocysteine metabolism. This article focuses on studies of strand breaks, micronuclei, or chromosomal aberrations regarding protective effects of vitamin B6, and probes whether it is folate-mediated one-carbon metabolism or the transsulfuration pathway for vitamin B6 which plays critical roles in prevention of cancer and cardiovascular disease.

Constituents from the Fruiting Bodies of Ganoderma applanatum and Their Aldose Reductase Inhibitory Activity

  • Lee, Sang-Hyun;Shim, Sang-Hee;Kim, Ju-Sun;Kang, Sam-Sik
    • Archives of Pharmacal Research
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    • v.29 no.6
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    • pp.479-483
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    • 2006
  • Eight compounds were isolated from the fruiting bodies of Ganoderma applanatum, and were identified as 2-methoxyfatty acids (1), 5-dihydroergosterol (2), ergosterol peroxide (3) $3{\beta},7{\beta},20,23{\zeta}-tetrahydroxy-11,15-dioxolanosta-8-en-26-oic$ acid (4), $7{\beta},20,23{\zeta}-trihydroxy-3,11,15-trioxolanosta-8-en-26-oic$ acid (5), cerevisterol (6), $7{\beta},23{\zeta}-dihydroxy-3,11,15-trioxolanosta-8,20E(22)-dien-26-oic$ acid (7), and $7{\beta}-hydroxy-3,11,15,23-tetraoxolanosta-8,20E(22)-dien-26-oic$ acid methyl ester (8) by spectral analysis. All compounds were isolated for the first time from this fruiting bodies, and their effect on rat lens aldose reductase (RLAR) activity was tested. Among these eight compounds, ergosterol peroxide (3) was found to exhibit potent RLAR inhibition, its $IC_{50}$ value being $15.4\;{\mu}g/mL$.

Analysis of Beauvericin and Unusual Enniatins Co-Produced by Fusarium oxysporum FB1501 (KFCC 11363P)

  • Song Hyuk-Hwan;Ahn Joong-Hoon;Lim Yoong-Ho;Lee Chan
    • Journal of Microbiology and Biotechnology
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    • v.16 no.7
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    • pp.1111-1119
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    • 2006
  • Beauvericins and enniatins are cyclohexadepsipeptides exhibiting various biological activities on animal systems, including humans. Fusarium oxysporum FB1501 (KFCC 11363P) that produces four different cyclohexadepsipeptides was isolated from soil in Korea and the structures of the four cyclohexadepsipeptides elucidated by HPLC, MS, IR, and NMR analyses. The molecular weights for compounds 1,2,3, and 4 were determined to be 654.5, 784.5, 668.6, and 682.5, respectively, on the basis of ESI-MS measurements. The IR spectra for all the compounds exhibited absorptions for ester $(1,733-1,743\;cm^{-1})$ and amide $(1,649-1,655\;cm^{-1})$ bonds that were very similar to those for beauvericin and enniatins with ester and amide absorptions. The results of the NMR analysis $(^{1}H,\;^{13}C,\;135-DEPT,\;COSY,\;HMQC,\;and\;HMBC;\;in\;COCl_{3})$ revealed that compounds 1,3, and 4 consisted of $_{L}-N-methyl\;valine$ (N-MeVal), $_{D}-{\alpha}-hydroxyisovaleic\;acid$ (Hiv), and 2-hydroxy-3-methylpentanoic acid (Hmp) residues (compound 1: three N-MeVal residues, two Hiv residues, and one Hmp residue; compound 3: three N-MeVal residues, one Hiv, and two Hmp residues; compound 4: three N-MeVal residues and three Hmp residues). Therefore, the compounds were identified as enniatin H (compound 1), enniatin I (compound 3), and enniatin MK1688 (compound 4). Compound 2 was analyzed as beauvericin according to 1D and 2D NMR analyses. This study is the first report related to the co-production of beauvericin with other unusual enniatins, such as enniatin H, enniatin I, and enniatin MK1688, by Fusarium oxysporum.

Effects of Apigenin on Glutamate-induced $[Ca^{2+}]_i$ Increases in Cultured Rat Hippocampal Neurons

  • Han, Ji-Hwa;Kim, Ki-Jung;Jang, Hyun-Jong;Jang, Ju-Ho;Kim, Myung-Jun;Sung, Ki-Wug;Rhie, Duck-Joo;Jo, Yang-Hyeok;Hahn, Sang-June;Lee, Mun-Yong;Yoon, Shin-Hee
    • The Korean Journal of Physiology and Pharmacology
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    • v.12 no.2
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    • pp.43-49
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    • 2008
  • Flavonoids have been shown to affect calcium signaling in neurons. However, there are no reports on the effect of apigenin on glutamate-induced calcium signaling in neurons. We investigated whether apigenin affects glutamate-induced increase of free intracellular $Ca^{2+}$ concentration ($[Ca^{2+}]_i$) in cultured rat hippocampal neurons, using fura-2-based digital calcium imaging and microfluorimetry. The hippocampal neurons were used between 10 and 13 days in culture from embryonic day 18 rats. Pretreatment of the cells with apigenin ($1{\mu}M$ to $100{\mu}M$) for 5 min inhibited glutamate ($100{\mu}M$, 1 min) induced $[Ca^{2+}]_i$ increase, concentration-dependently. Pretreatment with apigenin ($30{\mu}M$) for 5 min significantly decreased the $[Ca^{2+}]_i$ responses induced by two ionotropic glutamate receptor agonists, alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic (AMPA, $10{\mu}M$, 1 min) and N-methyl-D-aspartate (NMDA, $100{\mu}M$, 1 min), and significantly inhibited the AMPA-induced peak currents. Treatment with apigenin also significantly inhibited the $[Ca^{2+}]_i$ response induced by 50 mM KCl solution, decreased the $[Ca^{2+}]_i$ responses induced by the metabotropic glutamate receptor agonist, (S)-3,5-dihydroxy-phenylglycine (DHPG, 100 $[Ca^{2+}]_i$, 90 s), and inhibited the caffeine (10 mM, 2 min)-induced $[Ca^{2+}]_i$ responses. Furthermore, treatment with apigenin ($30{\mu}M$) significantly inhibited the amplitude and frequency of 0.1 mM $[Mg^{2+}]_o$-induced $[Ca^{2+}]_i$ spikes. These data together suggest that apigenin inhibits glutamate-induced calcium signaling in cultured rat hippocampal neurons.

Tissue Factor Inhibitory Flavonoids from the Fruits of Chaenomeles sinensis

  • Lee, Ming-Hong;Son, Yeon-Kyoung;Han, Yong-Nam
    • Archives of Pharmacal Research
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    • v.25 no.6
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    • pp.842-850
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    • 2002
  • Tissue factor (TF, tissue thromboplastin or coagulation factor III) accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor. In order to isolate TF inhibitors from the fruits of Chaenomeles sinensis, an activity-guided purification utilizing a bio-assay method of prothrombin time prolongation, was carried out to yield five active flavoniods such as hovetrichoside C (1) ($IC_{50}$ = 14.0 $\mu$g), luteolin-7-Ο-$\beta$-D-glucuronide (3) ($IC_{50}$ = 31.9$\mu$g), hyperin (4) ($IC_{50}$ = 20.8 $\mu$g), avicularin (6) ($IC_{50}$ = 54.8 $\mu$g) and quercitrin (10) ($IC_{50}$ = 135.7 $\mu$g), along with other inactive compounds such as ($\pm$)-(2E,4E)-Ο-$\beta$-D-glucopyranosyl-4'-hydroxy-$\beta$-ionylideneacetic acid ester (2), genistein-7-Ο-$\beta$-D-glucopyranoside (5), luteolin-3'-methoxy-4'-Ο-$\beta$-D-glucopyranoside (7), luteolin-7-Ο-$\beta$-D-glucuronide methyl ester (8), tricetin-3'-methoxy-4'-Ο-$\beta$-D-glucopyranoside (selagin-4'-Ο-$\beta$-D-glucopyranoside) (9), (-)-epicatechin (11), luteolin-4'-Ο-$\beta$-D-glucopyranoside (12) and apigenin-7-Ο-$\beta$-D-glucuronide methyl ester (13). The structures of the isolated compounds were elucidated through spectral analysis. Among them, compounds 1 to 9, 12 and 13 were isolated for the first time from the fruits of this plant and the compound 9 is a new flavonoid.

Regeneration Effects of Lespedeza cuneata Ethanol Extract on Experimental Open Wound in Rat (흰쥐의 외과적 창상에 대한 야관문 에탄올 추출물의 피부재생 효과)

  • Kim, Dae-Ik;Kim, Hye-Jeong
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.43 no.4
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    • pp.516-521
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    • 2014
  • The purpose of this study was to examine the skin regeneration ability of Lespedeza cuneata extract (LC) as well as verify its wound healing effects on an open wound in rats. Rats were divided into six groups (NO, saline treated group; CO, 1% carboxy methyl cellulose (CMC) treated group; PC, fucidin treated group; LCL, 1% LC treated group; LCM, 3% LC treated group; LCH, 5% LC treated group), and the experimental material was applied for 5 weeks. Elastase inhibition rate of the LCM group was 2.7% lower than that of butylated hydroxy anisole (BHA), which is an antioxidant. Futher, the collagenase inhibition rate of the LCM showed 7% higher activity than that of BHA. The left wound areas in the LCL group, LCM group, and LCH group after the 21st day were noticeably reduced in wound area by 54.2%, 53.5%, and 48.7%, respectively, compared to the CO group. This suggests that Lespedeza cuneata extract has healing effects on surgical wounds by promoting regeneration of skin epithelial tissue and synthesis of collagen.

Chemical Constituents from the Stems of Lagerstroemia indica and Their Anti-oxidant Effect (배롱나무의 항산화 활성 성분)

  • Woo, Kyeong Wan;Sim, Mi Ok;Park, Eel Jong;Kim, Min Suk;Suh, Won Se;Cho, Hyun Woo;Kwon, Hak Cheol;Park, Jong Cheol;Lee, Kang Ro
    • Korean Journal of Pharmacognosy
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    • v.47 no.3
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    • pp.204-210
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    • 2016
  • Phytochemical investigation of the 80% MeOH extract from the stems of Lagerstroemia indica resulted in the isolation of eighteen compounds; four norsesquiterpenes, fourteen phenolic derivatives. Their chemical structures were characterized by spectroscopic methods to be tachioside (1), isotachioside (2), 2,4,6-trimethoxyphenyl ${\beta}$-D-glucopyranoside (3), gallic acid 4-methyl ether (4), protocatechuic acid (5), gallic acid (6), vanillic acid (7), vanillin (8), 2-methoxy-5-hydroxymethyl-phenyl-1-O-(6"-galloyl)-${\beta}$-D-glucopyranoside (9), 2,4,6-trimethoxyphenol-1-O-${\beta}$-D-(6'-O-galloyl)-glucopyranoside (10), 4-hydroxy-3-methoxyphenyl-1-O-(6'-O-galloyl)-${\beta}$-D-glucopyranoside (11), vomifoliol (12), vomifoliol 9-O-${\beta}$-D-glucopyranoside (13), 6R,9R-3-oxo-${\alpha}$-ionol-9-O-${\beta}$-D-glucopyranoside (14), dihydrophaseic acid 4'-O-${\beta}$-D-glucopyranoside (15), ${\beta}$-hydroxypropiovanillone 3-O-${\beta}$-D-glucopyranoside (16), myrciaphenone A (17), and coumaric acid (18). Compounds 1-5 and 7-18 were isolated for the first time from this plant. Compounds 1-18 were investigated for their antioxidant properties using DPPH and ABTS radical scavenging capacity assay, $Fe^{2+}$ chelating, and FRAP assay. It was found that 4, 6, and 11 possessed the highest antioxidant capacities.