• Title/Summary/Keyword: 4-Hydroxybenzoic acid

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Improved NADPH Regeneration for Fungal Cytochrome P450 Monooxygenase by Co-Expressing Bacterial Glucose Dehydrogenase in Resting-Cell Biotransformation of Recombinant Yeast

  • Jeon, Hyunwoo;Durairaj, Pradeepraj;Lee, Dowoo;Ahsan, Md Murshidul;Yun, Hyungdon
    • Journal of Microbiology and Biotechnology
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    • v.26 no.12
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    • pp.2076-2086
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    • 2016
  • Fungal cytochrome P450 (CYP) enzymes catalyze versatile monooxygenase reactions and play a major role in fungal adaptations owing to their essential roles in the production avoid metabolites critical for pathogenesis, detoxification of xenobiotics, and exploitation avoid substrates. Although fungal CYP-dependent biotransformation for the selective oxidation avoid organic compounds in yeast system is advantageous, it often suffers from a shortage avoid intracellular NADPH. In this study, we aimed to investigate the use of bacterial glucose dehydrogenase (GDH) for the intracellular electron regeneration of fungal CYP monooxygenase in a yeast reconstituted system. The benzoate hydroxylase FoCYP53A19 and its homologous redox partner FoCPR from Fusarium oxysporum were co-expressed with the BsGDH from Bacillus subtilis in Saccharomyces cerevisiae for heterologous expression and biotransformations. We attempted to optimize several bottlenecks concerning the efficiency of fungal CYP-mediated whole-cell-biotransformation to enhance the conversion. The catalytic performance of the intracellular NADPH regeneration system facilitated the hydroxylation of benzoic acid to 4-hydroxybenzoic acid with high conversion in the resting-cell reaction. The FoCYP53A19+FoCPR+BsGDH reconstituted system produced 0.47 mM 4-hydroxybenzoic acid (94% conversion) in the resting-cell biotransformations performed in 50 mM phosphate buffer (pH 6.0) containing 0.5 mM benzoic acid and 0.25% glucose for 24 h at $30^{\circ}C$. The "coupled-enzyme" system can certainly improve the overall performance of NADPH-dependent whole-cell biotransformations in a yeast system.

Composition of Phenolic Compounds in Hypochaeris radica L. Extracts and their Allelopathic Effects on Gramineous Forage Crops (서양금혼초(Hypochaeris radicata L.) 추출물의 화본과 사료작물에 대한 타감작용 효과 및 phenole 화합물의 조성)

  • Kim, Og-Yim;Park, Sun-Ill;Jung, Ill-Min;Ha, Sang-Young
    • Korean Journal of Environmental Agriculture
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    • v.24 no.4
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    • pp.391-397
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    • 2005
  • This study was carried out to examine the allelopathic effect of the aqueous extract of Hypochaeris radicata L. on growth of three gramineous forage crops, tall fescue, perennial ryegrass and italian ryegrass. The result on relative elongation ration (RER) of gramineous forage crops treated with the aqueous extract of Hypochaeris radicata L. and the change of quantity generally indicated the inhibitory effect. The inhibitory effect was increased as its concentration was increased. As a result, it is ascertained that the aqueous extract of Hypochaeris radicata L. has allelopathy effect. According to the chemical experiment of the allelochemical substances in Hypochaeris radicata L. by HPLC, there are the differences at each part of plants. However, it is ascertained that there are eleven phenolic compounds, ${\rho}-hydroxybenzoic$ acid, chlorogenic acid, catechin, caffeic acid, syringic acid, salicylic acid, ${\rho}-coumaric$ acid, ferulic acid, hesperidin, trans-cinnamic acid and naringenin. Especially three phenolic acids such as caffeic acid, ferulic acid and naringenin were detected from all part of the plant.

Identification and Growth Inhibition of Phytotoxic Substances from Tomato Plant (토마토식물의 독성물질 확인과 생장억제작용)

  • 김영식
    • Journal of Plant Biology
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    • v.32 no.1
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    • pp.41-49
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    • 1989
  • Phenolic compounds such as gallic acid, ferulic acid, p-hydroxybenzoic acid, vanillic acid, salicylic acid, tannic acid, and hydroquinone were identified from the aqueous extracts and volatile substances of tomato plant by paper chromatography, high performance liquid chromatography and gas chromatography. The seed germination and seedling growth of the experimental species, lettuce and egg plant, were severely inhibited in 5$\times$10-3M of phenolic reagents identical to those identified from tomato plant. Germination and growth rate of test species in 5$\times$10-4M and 5$\times$10-5M were higher than that of 5$\times$10-3M. Therefore, 5$\times$10-3M of phenolic compounds would be assumed to be threshold concentration for allelopathic effects.

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In silico Analysis of Natural Compounds as Modulators of Type I Collagen

  • Narayanaswamy, Radhakrishnan;Wai, Lam Kok;Esa, Norhaizan Mohd;Ismail, Intan Safinar
    • Journal of Integrative Natural Science
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    • v.9 no.3
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    • pp.166-170
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    • 2016
  • Collagen plays a vital role in the maintenance of structure and function of a human body. It has been widely applied in various fields including biomedical, cosmeceutical, food, pharmaceutical and tissue engineering. In the present study, the docking behaviour of type I collagen with 15 different ligands namely hydroxymethylfurfural, methylglyoxal, methylsyringate, O-methoxyacetophenone, 3-phenyllactic acid, 4-hydroxybenzoic acid, kojic acid, lumichrome, galangin, artoindonesianin F, caffeic acid, 4-coumaric acid, origanol A, thymoquinone and quercetin was evaluated along with their putative binding sites using Discovery Studio Version 3.1. Docking studies and binding free energy calculations revealed that origanol A has maximum interaction energy (-40.48 kcal/mol) and quercetin with the least interaction energy (-15.44 kcal/mol) as compared to the other investigated ligands. Three ligands which are galangin, methylsyringate and origanol A were shown to interact with Asp21 amino acid residue of chain B (type I collagen). Therefore, it is strongly suggested that the outcomes from the present study might provide new insight in understanding these 15 ligands as potential type I collagen modulators for the prevention of collagen associate disorders.

Isolation and Identification of Low Molecular Phenolic Antioxidants from Ethylacetate Layer of Korean Black Raspberry (Rubus coreanus Miquel) Wine (복분자(Rubus coreanus Miquel) 와인의 에틸아세테이트층으로부터 저분자 페놀성 항산화 화합물의 단리·동정)

  • Kim, Seong-Ja;Lee, Hyoung-Jae;Park, Keun-Hyung;Rhee, Chong-Ouk;Lim, Ik-Jae;Chung, Hee-Jong;Moon, Jae-Hak
    • Korean Journal of Food Science and Technology
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    • v.40 no.2
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    • pp.129-134
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    • 2008
  • Five antioxidative active substances were isolated from the EtOAc layer (20 g/56.2 g) of Korean black raspberry (Rubus coreanus Miquel) wine (11 L, black raspberry 15.7 kg fresh wt. eq.) by various column chromatography and high performance liquid chromatography (HPLC). Proton nuclear magnetic resonance ($^1H$-NMR) spectroscopy and gas chromatography Electro Ionization-Mass Spectrometry (GC-EI-MS) identified these as 4-hydroxybenzoic acid (1, 0.1 mg), 3,4-dihydroxybenzoic acid (2, 0.3 mg), 4-(2-hydroxyethyl)-phenol (3, 0.6 mg; tyrosol), pyrocatechol (4, 0.3 mg), 3,4,5-trihydroxybenzoic acid ethyl ester (5, 0.6 mg; ethyl gallate). The presence of 1 and 2 in Korean black raspberry has previously been reported. However, the presence of 3-5 in Korean black raspberry, and the identification of 1-5 from the Korean black raspberry wine have never before been reported.

Phenolic constituents of Nelumbinis Semen and Their Tyrosinase Inhibitory Activity (연자육의 페놀성 성분 및 Tyrosinase 저해 활성)

  • Jeong, Ji Yeon;Mo, Eun Jin;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Korean Journal of Pharmacognosy
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    • v.46 no.1
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    • pp.1-5
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    • 2015
  • In the course of screening tyrosinase inhibitory activity, EtOAc-soluble fraction of Nelumbinis Semen (Seeds of Nelumbo nucifera) showed significant inhibition. Further fractionation of the EtOAc-soluble fraction resulted in 12 compounds, which were identified as 4-(hydroxymethyl)phenol (1), tyrosol (2), 4-(hydroxymethyl)benzaldehyde (3), 4-hydroxybenzoic acid (4), 4-(2-methoxyvinyl)benzene-1,2-diol (5), 2,6-dihydroxybenzoic acid (6), (2R-trans)-2,3-dihydro-3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (7), (+)-catechin (8), elephantorrhizol (9), (+)-dehydrovomifoliol (10), (-)-boscialin (11) and uridine (12). Compounds 5 and 7 were first reported from this plant. Among the isolated compounds, compound 7 showed strong inhibition on tyrosinase activity with mixed mechanism of competitive and noncompetitive inhibition.

Superoxide Radical Scavengers from the Whole Plant of Veronica peregrina

  • Ahn, Dal-Rae;Lee, Sa-Im;Yang, Jae-Heon;Cho, Chong-Hyeon;Hwang, Yong-Hun;Park, Jong-Han;Kim, Dae-Keun
    • Natural Product Sciences
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    • v.17 no.2
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    • pp.142-146
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    • 2011
  • In the course of screening for antioxidant compounds by measuring the radical scavenging effect on 1,1-diphenyl- 2-picrylhydrazyl (DPPH), a total extract from the whole plant of Veronica peregrina (Scrophulariaceae) was found to show potent antioxidant activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of six phenolic compounds including chrysoeriol (1), diosmetin (2), 4-hydroxybenzoic acid (3), apigenin (4), caffeic acid methylester (5) and protocatechuic acid (6). Their structures were elucidated by spectroscopic studies. Compounds 1-5 were isolated for the first time from this plant. Compounds 5 and 6 showed significant antioxidative effects in DPPH free radical scavenging and superoxide quenching activity assays.

Changes of phenolic acid contents and radical scavenging activities of ginseng according to steaming times (수삼의 증숙 횟수에 따른 페놀산 함량 변화와 라디칼 소거활성)

  • Kim, Young-Chan;Hong, Hee-Do;Rho, Jeong-Hae;Cho, Chang-Won;Rhee, Young-Kyung;Yim, Joo-Hyuk
    • Journal of Ginseng Research
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    • v.31 no.4
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    • pp.230-236
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    • 2007
  • This study was conducted to investigate the contents of the total phenolic compounds, and DPPH, ABTS radical scavenging activities of phenolic acid fractions of ginseng according to steaming times. Also the individual phenolic acid compositions and contents were analyzed by GC. The contents of the total phenolic compounds proportionally increased from 0.530 to 2.893% according to steaming times. Phenolic acid fractions were separated according to bound types, and the insoluble bound form fraction showed the highest contents followed by ester form fraction and free form fraction. The total contents of these three fractions (1.031-1.416%) were not significantly influenced by steaming times. Salicylic, cinamic, p-hydroxybenzoic, gentisic, vanillic, syringic, caffeic, ferolic acid were found in each fraction, and gentisic and ferolic acid were the major phenolic acid. Each phenolic acid fraction showed over 50% of DPPH and ABTS radical scavenging activities. There were no differences between the phenolic acid fractions according to binding types. Free radical scavenging activities were affected by a number of steaming times and augmented as steaming times increased.

Antioxidant Compounds Isolated from the Roots of Phlomis umbrosa Turcz.

  • Nguyen, Duc Hung;Le, Duc Dat;Zhao, Bing Tian;Ma, Eun Sook;Min, Byung Sun;Woo, Mi Hee
    • Natural Product Sciences
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    • v.24 no.2
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    • pp.119-124
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    • 2018
  • Two triterpenoids, arjunolic acid (1), belleric acid (2), five phenylethanoids, martynoside (3), orobanchoside (4), 3,4-dihydroxyphenethylalcohol-6-O-caffeoyl-${\beta}$-$\text\tiny{D}$-glucoside (5), leucosceptoside B (6), lunariifolioside (7), four phenolic acids, ferulic acid (8), syringic acid (9), vanillic acid (10), 4-hydroxybenzoic acid (11), and one lignan, (+)-syringaresinol-${\beta}$-$\text\tiny{D}$-glucoside (12), were isolated from the roots of P. umbrosa. All isolated compounds were explored for their antioxidant potential in the DPPH and ABTS assays. In DPPH assay, compound 5 showed high antioxidant capacity. Compounds 3, 4, 6, and 7 displayed considerable antioxidant activities. In addition, compounds 5-7 exhibited potential antioxidant capacities in the ABTS assay.

Tyrosinase Inhibitory Phenolic Constituents of Smilax china Leaves (청미래덩굴 잎의 페놀성 성분 및 Tyrosinase 저해 활성)

  • Kim, Sang Hyun;Ahn, Jong Hoon;Jeong, Ji Yeon;Kim, Seon Beom;Jo, Yang Hee;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Korean Journal of Pharmacognosy
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    • v.44 no.3
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    • pp.220-223
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    • 2013
  • In the course of screening tyrosinase inhibitory activity, total methanolic extract and EtOAc-soluble fraction of Smilax china leaves showed significant inhibitory activity. Further fractionation and isolation of the EtOAc-soluble fraction resulted in 12 phenolic compounds, which were identified as 4-hydroxybenzoic acid (1), 3,4-dihydroxybenzaldehyde (2), 3,4-dihydroxybenzoic acid (3), 3,4-dihydroxyacetophenone (4), 3-hydroxy-4-methoxy benzoic acid (5), trans-p-hydroxycinnamic acid (6), cis-p-hydroxycinnamic acid (7), trans-resveratrol (8), cis-resveratrol (9), dihydroresveratrol (10), moracin M (11) and kaempferol (12). Compounds 1-11 were first reported from this plant. Among the isolated compounds, compounds 2, 8, 9 and 12 showed strong inhibition on tyrosinase activity.