• Title/Summary/Keyword: Naringenin

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Assessment of Antioxidant and Phenolic Compound Concentrations as well as Xanthine Oxidase and Tyrosinase Inhibitory Properties of Different Extracts of Pleurotus citrinopileatus Fruiting Bodies

  • Alam, Nuhu;Yoon, Ki-Nam;Lee, Kyung-Rim;Kim, Hye-Young;Shin, Pyung-Gyun;Cheong, Jong-Chun;Yoo, Young-Bok;Shim, Mi-Ja;Lee, Min-Woong;Lee, Tae-Soo
    • Mycobiology
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    • v.39 no.1
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    • pp.12-19
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    • 2011
  • Cellular damage caused by reactive oxygen species has been implicated in several diseases, thus establishing a significant role for antioxidants in maintaining human health. Acetone, methanol, and hot water extracts of Pleurotus citrinopileatus were evaluated for their antioxidant activities against ${\beta}$-carotene-linoleic acid and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, reducing power, ferrous ion-chelating abilities, and xanthine oxidase inhibitory activities. In addition, the tyrosinase inhibitory effects and phenolic compound contents of the extracts were also analyzed. Methanol and acetone extracts of P. citrinopileatus showed stronger inhibition of ${\beta}$-carotene-linoleic acid compared to the hot water extract. Methanol extract (8 mg/mL) showed a significantly high reducing power of 2.92 compared to the other extracts. The hot water extract was more effective than the acetone and methanole extracts for scavenging DPPH radicals. The strongest chelating effect (92.72%) was obtained with 1.0 mg/mL of acetone extract. High performance liquid chromatography analysis detected eight phenolic compounds, including gallic acid, protocatechuic acid, chlorogenic acid, ferulic acid, naringenin, hesperetin, formononetin, and biochanin-A, in an acetonitrile and hydrochloric acid (5 : 1) solvent extract. Xanthine oxidase and tyrosinase inhibitory activities of the acetone, methanol, and hot water extracts increased with increasing concentration. This study suggests that fruiting bodies of P. citrinopileatus can potentially be used as a readily accessible source of natural antioxidants.

Studies on the Naringinase Produced by Aspergillus nidulans (Part I) Purification and Characteristics of Naringinase (Aspergillus nidulans 가 생산하는 Naringinase 관한 연구 (제2보) Naringinase의 정제 및 물리화학적 성질)

  • 변유량;문순옥;유주현
    • Microbiology and Biotechnology Letters
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    • v.6 no.2
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    • pp.65-73
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    • 1978
  • Naringinase extracted from the culture media of Aspergillus nidulans was purified, and the activity was proved to be stronger by 781 fold in the part of precipitation with ammonium sulfate, and column chromatography using DEAE-Sephadex A-25 and Sephadex G-100. Two fractions which had the same enzyme activity were isolated by the purification. Both fractions showed the highest enzymes activity under the reaction conditions of pH 5.0 and 40$^{\circ}C$. Molecular weight of fraction I and fraction II were estimated as 78,000 and 26,000 respectively. This indicated that fraction I would be trimer of fraction II. The enzyme was inhibited by glucose and rhammose, and the Km value was calculated to be 2.3${\times}$ 10$\^$-6/ g/ml.

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Hydroxylation of Compactin (ML-236B) by CYP105D7 (SAV_7469) from Streptomyces avermitilis

  • Yao, Qiuping;Ma, Li;Liu, Ling;Ikeda, Haruo;Fushinobu, Shinya;Li, Shengying;Xu, Lian-Hua
    • Journal of Microbiology and Biotechnology
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    • v.27 no.5
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    • pp.956-964
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    • 2017
  • Compactin and pravastatin are competitive cholesterol biosynthesis inhibitors of 3-hydroxy-3-methylglutaryl-CoA reductase and belong to the statin drugs; however, the latter shows superior pharmacokinetic characteristics. Previously, we reported that the bacterial P450, CYP105D7, from Streptomyces avermitilis can catalyze the hydroxylation of 1-deoxypentalenic acid, diclofenac, and naringenin. Here, we demonstrate that CYP105D7 could also catalyze compactin hydroxylation in vitro. In the presence of both bacterial and cyanobacterial redox partner systems with an NADPH regeneration system, the reaction produced two hydroxylated products, including pravastatin (hydroxylated at the C6 position). The steady-state kinetic parameters were measured using the redox partners of putidaredoxin and its reductase. The $k_m$ and $k_{cat}$ values for compactin were $39.1{\pm}8.8{\mu}M$ and $1.12{\pm}0.09min^{-1}$, respectively. The $k_{cat}/K_m$ value for compactin ($0.029min^{-1}{\cdot}{\mu}M^{-1}$) was lower than that for diclofenac ($0.114min^{-1}{\cdot}{\mu}M^{-1}$). Spectroscopic analysis showed that CYP105D7 binds to compactin with a $K_d$ value of $17.5{\pm}3.6{\mu}M$. Molecular docking analysis was performed to build a possible binding model of compactin. Comparisons of different substrates with CYP105D7 were conclusively illustrated for the first time.

Antioxidant Activities and Tyrosinase Inhibitory Effects of Different Extracts from Pleurotus ostreatus Fruiting Bodies

  • Alam, Nuhu;Yoon, Ki-Nam;Lee, Kyung-Rim;Shin, Pyung-Gyun;Cheong, Jong-Chun;Yoo, Young-Bok;Shim, Mi-Ja;Lee, Min-Woong;Lee, U-Youn;Lee, Tae-Soo
    • Mycobiology
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    • v.38 no.4
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    • pp.295-301
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    • 2010
  • We evaluated the antioxidant activity and tyrosinase inhibitory effects of Pleurotus ostreatus fruiting bodies extracted with acetone, methanol, and hot water. The antioxidant activities were tested against $\beta$-carotene-linoleic acid, reducing power, 1,1-diphenyl-2-picrylhydrazyl free radical scavenging activity, and ferrous chelating ability. Furthermore, phenolic acid and flavonoid contents were also analyzed. The methanol extract showed the strongest $\beta$-carotene-linoleic acid inhibition as compared to the other exracts. The acetone extract (8 mg/mL) showed a significantly high reducing power of 1.54 than the other extracts. The acetone extract was more effective than other extracts for scavenging on 1,1-diphenyl-2-picrylhydrazyl radicals. The strongest chelating effect (85.66%) was obtained from the acetone extract at 1.0 mg/mL. The antioxidant activities of the extracts from the P. ostreatus fruiting bodies increased with increasing concentration. A high performance liquid chromatography analysis detected seven phenolic compounds, including gallic acid, protocatechuic acid, chlorogenic acid, naringenin, hesperetin, formononetin, and biochanin-A in an acetonitrile and 0.1 N hydrochloric acid (5 : 1) solvent extract. The total phenolic compound concentration was $188{\mu}g$/g. Tyrosinase inhibition of the acetone, methanol, and hot water P. ostreatus extracts increased with increasing concentration. The results revealed that the methanol extract had good tyrosinase inhibitory ability, whereas the acetone and hot water extracts showed moderate activity at the concentrations tested. The results suggested that P. ostreatus may have potential as a natural antioxidant.

Antioxidant Activities and Phenolic Compounds Composition of Extracts from Mulberry (Morus alba L.) Fruit

  • Bang, In-Soo;Park, Hee-Yong;Yuh, Chung-Suk;Kim, Ae-Jung;Yu, Chang-Yeon;Ghimire, Bimal;Lee, Han-Shin;Park, Jae-Gun;Choung, Myoung-Gun;Lim, Jung-Dae
    • Korean Journal of Medicinal Crop Science
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    • v.15 no.2
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    • pp.120-127
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    • 2007
  • The objective of this research was to evaluate the ability of water and ethanol extracts from mulberry fruit (Morus alba L.) to influence the inhibitory activity of angiotensin converting enzyme (ACE) and xanthine oxidase(XOase). The total phenol contents and sixteen phenolic compounds were investigated in water and ethanol extracts. In order to understand the factors responsible for the potent antioxidant and antihypertensive ability of mulberry, it has been evaluated for anti-oxidative activity using Fenton's reagent/ethyl linoleate system and for free radical scavenging activity using the 1,1-diphenyl-2-picryl hydrazyl free radical generating system. The total phenol contents and total of phenolic compounds in ethanol extract showed higher levels than water extract in mulberry fruit six phenolic compounds (chlorogenic acid, narigin, syringic acid, quercetin, naringenin, kampferol) has a higher individual phenolic compound content in the 60% ethanol extraction than 80% ethanol extract. The inhibitory activity on angiotensin converting enzyme (ACE) were highest in 80% ethanol extract (9.0%). Also, activity of xanthine oxidase(XOase) inhibition appeared highest in 80% ethanol extracts and correlated well with the total phenolic content, which was modulated by the concentration of individual phenolic compounds. This result revealed, that strong biological activity was caused by specific phenol compound contents. Utilization of water and ethanol extracts from mulberry fruit are expected to be good candidate for development into source of free radical scavengers and anti-hypertentive activity

Flavonoid Inhibitors of β-Ketoacyl Acyl Carrier Protein Synthase III against Methicillin-Resistant Staphylococcus aureus

  • Lee, Jee-Young;Lee, Ju-Ho;Jeong, Ki-Woong;Lee, Eun-Jung;Kim, Yang-Mee
    • Bulletin of the Korean Chemical Society
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    • v.32 no.8
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    • pp.2695-2699
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    • 2011
  • ${\beta}$ Ketoacyl acyl carrier protein synthase III (KAS III) initiates fatty acid synthesis in bacteria and is a key target enzyme to overcome the antibiotic resistance problem. In our previous study, we found flavonoid inhibitors of Enterococcus faecalis KAS III and proposed three potent antimicrobial flavonoids against Enterococcus faecalis and Vancomycin-resistant Enterococcus faecalis with MIC values in the range of 128-512 ${\mu}g/mL$ as well as high binding affinities on the order from $10^6$ to $10^7\;M^{-1}$. Using these series of flavonoids, we conducted biological assays as well as docking study to find potent flavonoids inhibitors of Staphylococcus aureus KAS III with specificities against Staphylococcus aureus and Methicillin-resistant Staphylococcus aureus. Here, we propose that naringenin (5,7,4'-trihydroxyflavanone) and eriodictyol (5,7,3',4'-tetrahydroxyflavanone) are potent antimicrobial inhibitors of Staphylococcus aureus KAS III with binding affinity of $3.35{\times}10^5$ and $2.01{\times}10^5\;M^{-1}$, respectively. Since Arg38 in efKAS III is replaced with Met36 in saKAS III, this key difference caused one hydrogen bond missing in saKAS III compared with efKAS III, resulting in slight discrepancy in their binding interactions as well as decrease in binding affinities. 4'-OH and 7-OH of these flavonoids participated in hydrogen bonding interactions with backbone carbonyl of Phe298 and Ser152, respectively. In particular, these flavonoids display potent antimicrobial activities against various MRSA strains in the range of 64 to 128 ${\mu}M$ with good binding affinities.

ARYL HYDROCARBON- AND ESTROGEN-MEDIATED SIGNALS POSSIBLY CROSS TALK TO REGULATE CYP1A1 GENE EXPRESSION

  • Joung, Ki-Eun;Kim, Yeo-Woon;Min, Kyung-Nan;Sheen, Yhun-Yhong
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 2001.11a
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    • pp.112-112
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    • 2001
  • 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) is an environmental toxin that activates the aryl hydrocarbon receptor (AhR) and disrupts multiple endocrine signaling pathways by enhancing ligand metabolism, altering hormone synthesis, down regulating receptor levels, and interfering with gene transcription. And TCDD-mediated gene transactivation via the AhR has been shown to be dependent upon estrogen receptor (ER) expression in human breast cancer cells. In the present study, we have examined the effect of natural estrogen, phytoestrognes and environmental estrogens on the regulation of CYP1A1 gene expression in MCF-7 human breast cancer cell line. that ER and AhR are co-expressed. pCYP1A1 -luc reporter gene was transiently transfected into MCF-7 cells. These cells were treated with various chemicals and then luciferase assay was carried out. 17be1a-estradiol significantly inhibited TCDD stimulated luciferase activity dose dependently and this inhibition was partially recovered by concomitant treatment of tamoxifen. 17beta-estradiol metabolites, 2-hydroxyestradiol and 16alpha-estriol resulted in less potent inhibitory effect than estradiol and synthetic estrogen, diethylstilbestrol (DES) showed no effect on CYP1A1 gene expression. This study demonstrated that estrogen down-regulated TCDD stimulated CYP1A1 expression via ER mediation. And we have found out that several flavonoids such as genistein, kaempferol, daidzein, naringenin, and alkylphenols such as nonylphenol, 4-octylphenol and resveratrol also inhibited TCDD induced CYP1A1 expression like estrogen.

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Isolation of the Constituents from Clinopodium chinense var. shibetchense and Inhibition Activity on Cancer Cell Growth and Nitric Oxide Production (산층층이꽃 추출물로부터 성분 분리 및 암세포성장 및 NO 생성 억제활성)

  • Kim, Donghwa;Lee, Sang Kook;Park, Kyoung-Sik;Park, Hee-Juhn
    • Korean Journal of Pharmacognosy
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    • v.51 no.2
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    • pp.93-99
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    • 2020
  • This study was performed to find anti-inflammatory or antitumor compounds from the polar fraction obtained from the extract of Clinopodium chinense var. shibetchense (H. Lev) Koidz (Labiatae). Chromatography of the BuOH fraction yielded two flavonoid glycosides (compounds 1 and 2) and two saponins (compounds 3 and 4). On the basis of spectroscopic data, compounds 1 and 2 were identified to be ponciretin 7-O-α-L-rhamnopyranosyl-(1→6)-α-D-glucopyranoside (neoponcirin) and naringenin 7-O-α-L-rhamnopyranosyl-(1→6)-α-D-glucopyranoside (isonaringin). Compounds 3 and 4 were identified to be 3-O-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-fucopyranosyl}-saikogenin F (buddlejasaponin IV) and 3-O-{β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-fucopyranosyl}-21β-hydroxysaikogenin F (clinoposaponin XV). In addition, ursolic acid (5) was isolated and identified from the CHCl3 fraction. Inducible nitric oxide synthase (iNOS) assay and sulforhodamine B (SRB) assay were performed to lead a potential anti-inflammatory or anti-tumor compounds from C. chinense var. shibetchense. Of the four compounds (1 - 4), compound 3 considerably inhibited cancer cell growth and NO production (IC50s, 5.59 μM in iNOS assay and 6.62 - 14.88 μM in SRB assay).

Phenolic Compounds from the Fruits of Paulownia coreana Uyeki (오동나무 열매 추출물의 페놀성 화합물)

  • Si, Chuan-Ling;Kim, Jin-Kyu;Kwon, Dong-Joo;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.1
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    • pp.79-85
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    • 2006
  • Paulownia coreana Uyeki fruits were collected, extracted with acetone-$H_2O$ (7:3, v /v), fractionated with n-hexane, methylene chloride, and ethyl acetate, then freeze dried to give some dark brown powder. The ethyl acetate soluble mixture was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. Spectrometric analysis such as NMR and MS including TLC were performed to establish the structures of the isolated compounds. From the ethyl acetate fraction, one phenolic acid (I) and five flavonoids (II~VI) and were isolated and elucidated. The antioxidative activities were tested on the isolated compounds, crude and fractionated extractives by DPPH radical scavenging method. The result showed that caffeic acid, kaempferol, luteolin, quercetin and the EtOAc soluble fraction exhibited higher activities than those of ${\alpha}$-tocopherol and BHT.

Extractives of the Wood of Black Locust and the Bark of Poplar as Decay-Resistant Hardwood Tree Species (내후성 활엽수종인 아까시나무 목질부와 현사시나무 수피의 추출성분)

  • Bae, Young-Soo;Ham, Yeon-Ho
    • Journal of the Korean Wood Science and Technology
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    • v.28 no.3
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    • pp.52-61
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    • 2000
  • Black locust(Robinia pseudoacacia) and poplar(Populus alba ${\times}$ glandulosa) trees were collected, extracted with acetone-$H_2O$(7:3, v/v) after drying, fractionated with hexane, chloroform and ethylacetate, and freeze dried to get some brown powder. Each fraction of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluting solvents. The wood extractives of black locust contained (+)-leucorobinetinidin as flavan, robtin as flavanone and dihydrorobinetin as flavanonol, and robinetin as flavonol. The poplar bark extractives contained various kinds of phenolic compounds : (+)-catechin as flavan, naringeoin, eriodictyol, sakuranetin, aromadendrin and taxifolin as flavanonol, salireposide as salicin derivative, and minor compounds such as aesculin and p-coumaric acid. However, aesculin has not been reported as a constituent of the poplar bark in Korea yet. NMR and FAB-MS analyses were done to elucidate the structures of isolated phenolic constituents.

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