• Title/Summary/Keyword: bioactive metabolites

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Biotransformation of Ginsenoside Rb1, Crocin, Amygdalin, Geniposide, Puerarin, Ginsenoside Re, Hesperidin, Poncirin, Glycyrrhizin, and Baicalin by Human Fecal Microflora and Its Relation to Cytotoxicity Against Tumor Cells

  • Kim, Young-Suk;Kim, Jung-Jin;Cho, Ki-Ho;Jung, Woo-Sang;Moon, Sang-Kwan;Park, Eun-Kyung;Kim, Dong-Hyun
    • Journal of Microbiology and Biotechnology
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    • v.18 no.6
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    • pp.1109-1114
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    • 2008
  • To understand the role of intestinal microflora in the biological effect of functional herbs, which have been used in Korea, Japan, and China as traditional medicines, and suggest new bioactive compounds transformed from herbal constituents, the metabolic activities of the functional herb components (ginsenoside Rb1, crocin, amygdalin, geniposide, puerarin, ginsenoside Re, poncirin, hesperidin, glycyrrhizin, and baicalin) toward their bioactive compounds (compound K, crocetin, benzaldehyde, genipin, daidzein, ginsenoside Rh1, ponciretin, hesperetin, 18b-glycyrrhetic acid, and baicalein) were measured in fecal specimens. The metabolic activities of these components were $882.7{\pm}814.5$, $3,938.1{\pm}2,700.8$, $2,375.5{\pm}913.7$, $1,179.4{\pm}795.7$, $24.6{\pm}10.5$, $11.4{\pm}10.8$, $578.8{\pm}206.1$, $1,150.0{\pm}266.1$, $47.3{\pm}58.6$, and $12,253.0{\pm}6,527.6\;{\mu}mol/h/g$, respectively. No differences were found in the metabolic activities of the tested components between males and females, although these metabolic activities between individuals are extensively different. The metabolites of functional herb components showed more potent cytotoxicity against tumor cells than nonmetabolites. These findings suggest that intestinal microflora may activate the pharmacological effect of herbal food and medicines and must be the biocatalytic converter for the transformation of herbal components to bioactive compounds.

Nuclear Magnetic Resonance (NMR)-Based Quantification on Flavor-Active and Bioactive Compounds and Application for Distinguishment of Chicken Breeds

  • Kim, Hyun Cheol;Yim, Dong-Gyun;Kim, Ji Won;Lee, Dongheon;Jo, Cheorun
    • Food Science of Animal Resources
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    • v.41 no.2
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    • pp.312-323
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    • 2021
  • The purpose of this study was to use 1H nuclear magnetic resonance (1H NMR) to quantify taste-active and bioactive compounds in chicken breasts and thighs from Korean native chicken (KNC) [newly developed KNCs (KNC-A, -C, and -D) and commercial KNC-H] and white-semi broiler (WSB) used in Samgye. Further, each breed was differentiated using multivariate analyses, including a machine learning algorithm designed to use metabolic information from each type of chicken obtained using 1H-13C heteronuclear single quantum coherence (2D NMR). Breast meat from KNC-D chickens were superior to those of conventional KNC-H and WSB chickens in terms of both taste-active and bioactive compounds. In the multivariate analysis, meat portions (breast and thigh) and chicken breeds (KNCs and WSB) could be clearly distinguished based on the outcomes of the principal component analysis and partial least square-discriminant analysis (R2=0.945; Q2=0.901). Based on this, we determined the receiver operating characteristic (ROC) curve for each of these components. AUC analysis identified 10 features which could be consistently applied to distinguish between all KNCs and WSB chickens in both breast (0.988) and thigh (1.000) meat without error. Here, both 1H NMR and 2D NMR could successfully quantify various target metabolites which could be used to distinguish between different chicken breeds based on their metabolic profile.

Overexpression of afsR and Optimization of Metal Chloride to Improve Lomofungin Production in Streptomyces lomondensis S015

  • Wang, Wei;Wang, Huasheng;Hu, Hongbo;Peng, Huasong;Zhang, Xuehong
    • Journal of Microbiology and Biotechnology
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    • v.25 no.5
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    • pp.672-680
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    • 2015
  • As a global regulatory gene in Streptomyces, afsR can activate the biosynthesis of many secondary metabolites. The effect of afsR on the biosynthesis of a phenazine metabolite, lomofungin, was studied in Streptomyces lomondensis S015. There was a 2.5-fold increase of lomofungin production in the afsR-overexpressing strain of S. lomondensis S015 N1 compared with the wild-type strain. Meanwhile, the transcription levels of afsR and two important genes involved in the biosynthesis of lomofungin (i.e., phzC and phzE) were significantly upregulated in S. lomondensis S015 N1. The optimization of metal chlorides was investigated to further increase the production of lomofungin in the afsR-overexpressing strain. The addition of different metal chlorides to S. lomondensis S015 N1 cultivations showed that CaCl2, FeCl2, and MnCl2 led to an increase in lomofungin biosynthesis. The optimum concentrations of these metal chlorides were obtained using response surface methodology. CaCl2 (0.04 mM), FeCl2 (0.33 mM), and MnCl2 (0.38 mM) gave a maximum lomofungin production titer of 318.0 ± 10.7 mg/l, which was a 4.1-fold increase compared with that of S. lomondensis S015 N1 without the addition of a metal chloride. This work demonstrates that the biosynthesis of phenazine metabolites can be induced by afsR. The results also indicate that metal chlorides addition might be a simple and useful strategy for improving the production of other phenazine metabolites in Streptomyces.

Simultaneous Analysis of Bioactive Metabolites from Rehmannia glutinosa by HPLC-DAD-MS/MS

  • Won, Tae-Hyung;Ryu, Sung-Kwang;Kang, Sam-Sik;Shin, Jong-Heon
    • Natural Product Sciences
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    • v.16 no.2
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    • pp.116-122
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    • 2010
  • A high-performance liquid chromatography (HPLC) with diode array detector (DAD) and electrospray ionization mass spectrometry (ESI-MS) was established for the simultaneous determination of five representative metabolites of the iridoid and phenolic classes from Rehmannia glutinosa. The optimal chromatographic conditions were obtained on an ODS column (5 mm, $4.6{\times}250\;mm$) with the column temperature at $25^{\circ}C$. The mobile phase was composed of water and acetonitrile using a gradient elution with the flow rate 0.3 mL/min. Detection wavelength was set at 205 nm. All calibration curves showed good linear regression ($r^2$ > 0.997) within test ranges. Limits of detection (LOD) and quantitation (LOQ) values were lower than 0.123 and $0.373\;{\mu}g/mL$, respectively. The developed method provided satisfactory precision and accuracy with overall intra-day and inter-day variations of 0.09 - 0.76% and 0.16 - 1.41%, respectively, and the overall recoveries of 99.03 - 102.67% for all of the compounds analyzed. In addition, effectiveness of diverse extraction methods was compared to each other for the development of standard analytic method. The verified method was successfully applied to the quantitative determination of five representative metabolites in twenty-one commercial Rehmannia glutinosa samples from different markets in Korea and China. The analytical results showed that the contents of the five analytes vary significantly with sources.

Control of Anthracnose and Gray Mold in Pepper Plants Using Culture Extract of White-Rot Fungus and Active Compound Schizostatin

  • Dutta, Swarnalee;Woo, E-Eum;Yu, Sang-Mi;Nagendran, Rajalingam;Yun, Bong-Sik;Lee, Yong Hoon
    • Mycobiology
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    • v.47 no.1
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    • pp.87-96
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    • 2019
  • Fungi produce various secondary metabolites that have beneficial and harmful effects on other organisms. Those bioactive metabolites have been explored as potential medicinal and antimicrobial resources. However, the activities of the culture filtrate (CF) and metabolites of whiterot fungus (Schizophyllum commune) have been underexplored. In this study, we assayed the antimicrobial activities of CF obtained from white-rot fungus against various plant pathogens and evaluated its efficacy for controlling anthracnose and gray mold in pepper plants. The CF inhibited the mycelial growth of various fungal plant pathogens, but not of bacterial pathogens. Diluted concentrations of CF significantly suppressed the severity of anthracnose and gray mold in pepper fruits. Furthermore, the incidence of anthracnose in field conditions was reduced by treatment with a 12.5% dilution of CF. The active compound responsible for the antifungal and disease control activity was identified and verified as schizostatin. Our results indicate that the CF of white-rot fungus can be used as an eco-friendly natural product against fungal plant pathogens. Moreover, the compound, schizostatin could be used as a biochemical resource or precursor for development as a pesticide. To the best of our knowledge, this is the first report on the control of plant diseases using CF and active compound from white-rot fungus. We discussed the controversial antagonistic activity of schizostatin and believe that the CF of white-rot fungus or its active compound, schizostatin, could be used as a biochemical pesticide against fungal diseases such as anthracnose and gray mold in many vegetables.

Prebiotics enhance the biotransformation and bioavailability of ginsenosides in rats by modulating gut microbiota

  • Zhang, Xiaoyan;Chen, Sha;Duan, Feipeng;Liu, An;Li, Shaojing;Zhong, Wen;Sheng, Wei;Chen, Jun;Xu, Jiang;Xiao, Shuiming
    • Journal of Ginseng Research
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    • v.45 no.2
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    • pp.334-343
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    • 2021
  • Background: Gut microbiota mainly function in the biotransformation of primary ginsenosides into bioactive metabolites. Herein, we investigated the effects of three prebiotic fibers by targeting gut microbiota on the metabolism of ginsenoside Rb1 in vivo. Methods: Sprague Dawley rats were administered with ginsenoside Rb1 after a two-week prebiotic intervention of fructooligosaccharide, galactooligosaccharide, and fibersol-2, respectively. Pharmacokinetic analysis of ginsenoside Rb1 and its metabolites was performed, whilst the microbial composition and metabolic function of gut microbiota were examined by 16S rRNA gene amplicon and metagenomic shotgun sequencing. Results: The results showed that peak plasma concentration and area under concentration time curve of ginsenoside Rb1 and its intermediate metabolites, ginsenoside Rd, F2, and compound K (CK), in the prebiotic intervention groups were increased at various degrees compared with those in the control group. Gut microbiota dramatically responded to the prebiotic treatment at both taxonomical and functional levels. The abundance of Prevotella, which possesses potential function to hydrolyze ginsenoside Rb1 into CK, was significantly elevated in the three prebiotic groups (P < 0.05). The gut metagenomic analysis also revealed the functional gene enrichment for terpenoid/polyketide metabolism, glycolysis, gluconeogenesis, propanoate metabolism, etc. Conclusion: These findings imply that prebiotics may selectively promote the proliferation of certain bacterial stains with glycoside hydrolysis capacity, thereby, subsequently improving the biotransformation and bioavailability of primary ginsenosides in vivo.

Inhibition of Tyrosinase by Metabolites Originating from Thrichoderma atroviride (Thrichoderma atroviride 배양액의 tyrosinase 억제제에 관한 연구)

  • Kang, Dong Woo;Kim, Kyu-Min;Kim, Ye-Seong;Seo, Yu-Jin;Song, Da-Yeong;Oh, Da-Yun;Choi, Si-On;Hwang, Ju-Hyeon;Kim, Sam Woong;Bang, Kyu Ho;Gal, Sang Wan
    • Journal of Life Science
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    • v.31 no.1
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    • pp.47-51
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    • 2021
  • In today's society, functional whitening cosmetics are important to beauty. Fungi are known to produce a variety of whitening-related metabolites. In this study, we searched for tyrosinase inhibitors with metabolic products derived from Trichoderma atroviride supernatant in order to apply a material for whitening functional cosmetics. In addition, the inhibitory effect was compared to arbutin, which has already been approved as a whitening raw material by the Korea Ministry of Food and Drug Safety (KMFDS). The metabolites from the T. atroviride supernatant showed higher tyrosinase inhibitory activity than that of arbutin. Some of the tyrosinase inhibitors were stable to heat, whereas some were unstable. The heat unstable material was exhibited in the case of samples treated with little amounts, such as 0.02~0.2%. They were very unstable in acidic and alkali pHs, especially under acidic conditions. However, it was found that a weakly-acidic to neutral pH range was the optimal working pH, especially neutral pH. Since the activity of the inhibitory substances in the T. atroviride supernatant was maintained regardless of proteinase K treatment, it was assumed that the metabolites, but not the bioactive peptides, were involved in the activity. In summary, we propose that the metabolites derived from T. atroviride supernatant have strong potential as whitening raw material.

Isolation and Structure Determination of a Proteasome Inhibitory Metabolite from a Culture of Scytonema hofmanni

  • Shim, Sang-Hee;Chlipala, George;Orjala, Jimmy
    • Journal of Microbiology and Biotechnology
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    • v.18 no.10
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    • pp.1655-1658
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    • 2008
  • Cyanobacteria, blue-green algae, are a rich source of bioactive secondary metabolites with many potential applications. The ubiquitin-proteasome proteolytic system plays an important role in selective protein degradation and regulates cellular events including apoptosis. Cancer cells are more sensitive to the proapoptotic effects of proteasome inhibition than normal cells. Thus, proteasome inhibitors can be potential anticancer agents. Cyanobacteria have been shown to be a rich source of highly effective inhibitors of proteases. A proteasome inhibitor was screened from an extract of the culture of Scytonema hofmanni on the basis of its inhibitory activity, which led to the isolation of nostodione A with an $IC_{50}$ value of 50${\mu}M$. Its structure was determined by spectroscopic methods such as $^{1}H$-NMR and ESI-MS spectral analyses.

Bioactive Metabolites from the Brittle Star Ophioplocus japonicus

  • Wang, Wei-Hong;Hong, Jong-Ki;Lee, Chong-Ok;Cho, Hee-Young;Shin, Sook;Jung, Jee-H.
    • Natural Product Sciences
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    • v.10 no.6
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    • pp.253-261
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    • 2004
  • Ten terpenes (1-10), two sterols (11 and 12), and two unusual phenylpropanoids (13 and 14) were isolated from the brittle star Ophioplocus japonicus (Family Ophiuridae). Their structures were identified by analyses of the spectral data and by comparison with the literature data. The terpenes (1-10) and phenylpropanoids (13 and 14) are first encountered in brittle stars. These compounds were evaluated for cytotoxicity against a small panel of human solid tumor cell lines. Compounds 6-10 and 14 displayed moderate to significant cytotoxicity. The compounds were evaluated for antibacterial activity against 20 clinically isolated strains. Compound 5 exhibited antibacterial activities against three Streptococcus and three Staphylococcus strains.

Isolation and Structure Determination of an Imidazo-pyrimidine, 5-Chlorocavernicolin, Maleimide oximes and Nucleosides from a Marine Sponge Extract

  • Kulkarni, Roshan R.;Kim, Jang Hoon;Kim, Young Ho;Oh, Sangtaek;Na, MinKyun
    • Natural Product Sciences
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    • v.21 no.1
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    • pp.25-29
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    • 2015
  • In a continuation of our studies to discover bioactive secondary metabolites from marine sources, we further investigated samples from a tryptamine and phenyl-alkane producing sponge, which resulted in the isolation of four uncommon small molecules and five nucleosides. Their structures were determined to be 7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one (1), 5-chlorocavernicolin (2), maleimide-5-oxime (3), 3-methylmaleimide-5-oxime (4), uridine (5), 2'-deoxyuridine (6), thymidine (7), adenine (8), and adenosine (9) by spectroscopic analyses. The isolated compounds were evaluated for inhibitory activity against soluble epoxide hydrolase (sEH) as well as the Wnt/${\beta}$-catenine signaling pathway.