• Title, Summary, Keyword: metabolites

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Endophytic Fungi Inhabiting Medicinal Plants and Their Bioactive Secondary Metabolites

  • Lee, Changyeol;Shim, Sang Hee
    • Natural Product Sciences
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    • v.26 no.1
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    • pp.10-27
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    • 2020
  • Endophytes are defined as microorganisms that spend part of lifetime interior of plant tissues without causing negative effects. They have been used for agricultural purpose, biofuel production, bioremediation, medication, etc. In particular, endophytes have been emerged as a good source for bioactive secondary metabolites. A large number of secondary metabolites are currently being reported. In this report, we focus on the secondary metabolites that were originated from endophytic fungi inhabiting medicinal plants. They were classified into several groups such as nitrogenous compounds, steroids, sulfide-containing metabolites, terpenoids, polyketides, and miscellaneous for discussion of chemical structures and biological activities.

Identification of Propentofylline Metabolites in Rats by Gas Chromatography/Mass Spectrometry

  • Kwon, Oh-Seung;Ryu, Jae-Chun
    • Archives of Pharmacal Research
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    • v.23 no.4
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    • pp.374-380
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    • 2000
  • Propentofylline (PPF, 3-methyl-1-(5-oxohexyl)-7-propylxanthine) has been reported to be a compound for treatment of both vascular dementia and dementia of the Alzheimer type. The short half-life (about 15 min) of PPF at the terminal elimination phase and poor bioavailability after oral administration of PPF to rabbits (Kim et al., 1992) suggest in part that this drug takes the extensive first-pass metabolism in the liver. In addition, the metabolic pathway for PPF remains unclear. The objective of this experiment is to identify urinary metabolites of PPF in rats. For the identification of the metabolites, rat urine was collected after oral administration of 100${m}g/kg$ PPF. PPF metabolite, 3-methyl-1-(5-hydroxyhexyl)-7-propylxanthine, was synthesized and confirmed by gas chromatography/mass spectroscopy (GC/MS) and $^1H$ nuclear magnetic resonance spectroscopy. The urinary metabolites of PPF were extracted with diethyl ether and identified by electron impact and chemical ionization GC/MS. One urinary metabolite was confirmed to be 3-methyl-1-(5-hydroxyhexyl)-7-propylxanthine by synthesized authentic compound. Several metabolites of monohydroxy- and dihydroxy-PPF were identified based on mass fragmentation of both intact and trimethylsilylated derivatives of PPF metabolites and the novel structure of these metabolites is suggested based on mass spectra.

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Tentative identification of 20(S)-protopanaxadiol metabolites in human plasma and urine using ultra-performance liquid chromatography coupled with triple quadrupole time-of-flight mass spectrometry

  • Ling, Jin;Yu, Yingjia;Long, Jiakun;Li, Yan;Jiang, Jiebing;Wang, Liping;Xu, Changjiang;Duan, Gengli
    • Journal of Ginseng Research
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    • v.43 no.4
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    • pp.539-549
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    • 2019
  • Background: 20(S)-Protopanaxadiol (PPD), the aglycone part of 20(S)-protopanaxadiol ginsenosides, possesses antidepressant activity among many other pharmacological activities. It is currently undergoing clinical trial in China as an antidepressant. Methods: In this study, an ultra-performance liquid chromatography coupled with triple quadrupole time-of-flight mass tandem mass spectrometry method was established to identify the metabolites of PPD in human plasma and urine following oral administration in phase IIa clinical trial. Results: A total of 40 metabolites in human plasma and urine were identified using this method. Four metabolites identified were isolated from rat feces, and two of them were analyzed by NMR to elucidate the exact structures. The structures of isolated compounds were confirmed as (20S,24S)-epoxydammarane-12,23,25-triol-3-one and (20S,24S)-epoxydammarane-3,12,23,25-tetrol. Both compounds were found as metabolites in human for the first time. Upon comparing our findings with the findings of the in vitro study of PPD metabolism in human liver microsomes and human hepatocytes, metabolites with m/z 475.3783 and phase II metabolites were not found in our study whereas metabolites with m/z 505.3530, 523.3641, and 525.3788 were exclusively detected in our experiments. Conclusion: The metabolites identified using ultra-performance liquid chromatography coupled with triple quadrupole time-of-flight mass spectrometry in our study were mostly hydroxylated metabolites. This indicated that PPD was metabolized in human body mainly through phase I hepatic metabolism. The main metabolites are in 20,24-oxide form with multiple hydroxylation sites. Finally, the metabolic pathways of PPD in vivo (human) were proposed based on structural analysis.

Enzyme Metabolite Analysis Using Data Mining (데이터 마이닝을 활용한 효소 대사물의 분석)

  • Ceong, Hyi-Thaek;Park, Chun-Goo
    • The Journal of the Korea institute of electronic communication sciences
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    • v.11 no.10
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    • pp.969-982
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    • 2016
  • Recently, the researches to discovery drug candidates from natural herbs have received considerable attention. In human body, enzyme mostly metabolize the compounds of natural herbs. In this study, we analysis the enzyme interactions using assoication mining. We get this data from BRENDA(: BRaunschweig ENzyme DAtabase) system. Based on enzyme interaction model, we divide the metabolites into substrate metabolites, product metabolites, inhibitor metabolites, and activating metabolites. We then compose substrate metabolite transaction, product metabolite transaction with each metabolites and enzyme interaction transaction with all metabolites. Also we take account of organism for each transactions. We mine frequent metabolites and patterns from six transactions using association rule mining. And we analysis the relationship among metabolites. As a result, we identify the distributions and patterns of metabolites consist in enzyme interactions. We found that metabolites include in only substrate are identified and have very low supports. This results can be useful to develop the effective metabolism prediction model for compounds of natural herbs.

Synthesis of Glucuronic Acid Conjugates of Linoleic Acid Metabolites (리놀레산 대사체들의 글루쿠론산 결합화합물 합성)

  • Kang, Dong Wook
    • Journal of the Korean Chemical Society
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    • v.57 no.6
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    • pp.738-743
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    • 2013
  • Linoleic acid and its metabolites have various medicinal effects with carboxylic acid functional group. General carboxylic acid compounds are discovered as glucuronide metabolites by UGT glucuronosyl transferase at liver. Consequently, glucuronides of linoleic acid metabolites are expected as potent conjugated metabolite. A previous study reported two epoxide metabolites and two dihydroxy metabolites of linoleic acid. There are prepared their glucuronic acid conjugated compounds as potent linoleic acid metabolites.

Antimicrobial and Antineoplastic Tyrosine Metabolites from a Marine Sponge, Aplysina fistularis

  • Goo, Yang-M.
    • Archives of Pharmacal Research
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    • v.8 no.1
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    • pp.21-30
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    • 1985
  • Examination of the constituents of a marine sponge, Aplysina fishtularis, indicated that brominated tyrosine metabolites were mainly responsible for antimicrobial and antineoplastic activities. Halogenated tyrosine metabolites, 2, 6-dibromo-(2), 2-bromo-3-chloro-(3) and 2, 6-dibromo-(5), 5-a mino-2-bromo-6-chloro-(6) and 5-amino-2, 6-dich-loro-(7) 4-hydroxy-2-cyclohexenone-4-acetic acid lactams were identified as the major antineoplastic and antimicrobial principles. Many other brominated tyrosine metabolites were also confirmed, but they did not show antimicrobial and antineoplastic activities.

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Effect of Food on the Pharmacokinetics of YH439 and Its Metabolites in Rats

  • Kim, Moon-Kyoung;Ahn, Byung-Nak;Yoo, Joong-Keun;Lee, Jong-Wook
    • Archives of Pharmacal Research
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    • v.20 no.6
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    • pp.629-632
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    • 1997
  • The pharmacokinetics of YH439 and its metabolites were investigated after oral administration of YH439 to rats to investigate the food effect. After oral administration of YH439, its metabolites, M4 and M5 were detected in plasma. YH439 was not detected in the plasma for both fasted and fed rats for all doses studied. The pharmacokinetic parameters of the metabolites were not affected by food at all doses studied. The results of this study indicated that there are no significant food effects on the pharmacokinetics of YH439 and its metabolites in rats.

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Pharmacological Evaluation of Proprietary Preparation from Bacterial Metabolites with Special Reference to its Immunomodulatory Actions

  • Auddy, Biswajit;Mitra, Susil K.;Mukherjee, Biswapati
    • Natural Product Sciences
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    • v.5 no.1
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    • pp.7-11
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    • 1999
  • A mixture of several bacterial metabolites $(Sterodin{\circledR})$ was used to study its effect on major immunocytes, in vivo and in vitro. This mixture of bacterial metabolites increased number of macrophages and neutrophils and their phagocytic activity in experimental animals for a transient period. BSA induced antibody production was found to be higher in the drug treated group. These results indicated that the bacterial metabolites probably acted through non-specific defence mechanism against invading organisms and the chance of reinfection was reduced.

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Covalent Interactions of Reactive Pentachlorophenol Metabolites with Cellular Macromolecules (Pentachlorophenol 대사물과 세포내 거대분자물의 반응에 관한 연구)

  • 정요찬;윤병수;이영순;조명행
    • Toxicological Research
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    • v.13 no.3
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    • pp.257-263
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    • 1997
  • Pentachlorophenol(PCP) which ks widely used in wood preservation, pulp and paper mills, has led to a substantial envirortmental contamination. To get the reliable data for the effective health risk assessment with PCP, covalent binding potential of PCP to cellular macromolecules and glutathione(GSH) was investigated after intraperitoneal administration of $^{14}C-PCP$ to rats. PCP metabolites were able to bind covalently to serum albumin and hepatic protein in a dose- and time-dependent manner. Hepatic protein adducts of PCP metabolites were increased as a function of cytochrome P-450 activities, whereas, albumin adducts significantly decreased. Covalent binding of PCP metabolites with DNA or hemoglobin was not observed. GSH levels in liver tissue decreased over 12hrs, however, the level was recovered after 48hrs. Tetrachloro-1,4-benzoquinone (1,4-TCBQ), one of the most reactive PCP metabolites, conjugated with GSH very rapidly. Base on our results, we could conclude that PCP metabolized to reactive electrophilic metabolites by cytochrome P-450 isoenzymes and conjugated rapidly with neighboring protein or nonprotein sulfhydryl before reacting with DNA or hemoglobin. We propose that albumin adducts and mercapturic acids of PCP metabolites can be used good biomarker of recent PCP exposure.

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Relationship of Transformation Efficiency and Metabolites Induced in Korean Soybean Cotyledons Treated with Sonication

  • Song, Kitae;Yim, Won Cheol;Jung, Gun-Ho;Kim, Sun Lim;Kwon, Young-Up;Lee, Byung-Moo
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.58 no.2
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    • pp.119-127
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    • 2013
  • The interaction between Agrobacterium and soybean has been studied at the transcriptome level but not at the metabolic level. However, it is necessary to investigate the difference in metabolites between susceptible and non-susceptible cultivars for high efficiency transformation. We investigated the difference in metabolites from sonicated soybean cotyledons of Korean cultivars and Bert cultivar. To identify difference in metabolites, sonicated extracts were analysed by Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR/MS). The soybean cultivars were classified by susceptibility using green fluorescent protein expression. We found a difference in metabolites between the high susceptible and low susceptible cultivars. The FT-ICR/MS experimental m/z data of different metabolites were compared with theoretical m/z in KNApSAcK database. The candidate list was made using KNApSAcK and focused on phenolic compounds. These candidate metabolites are speculated to influence factors in the interaction. This list of candidates may be useful to investigate the interaction between Agrobacterium and plants to increase transformation efficiency.