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Structure type: monomer ; 524.3609 [M]+
C₃₀H₄₆N₅O₃
Compound class: nucleoside

• Article ID: 5682
  Lau SK, Lam CW, Curreem SO, Lee KC, Lau CC, Chow WN, Ngan AH, To KK, Chan JF, Hung IF, Yam WC, Yuen KY, Woo PC "Identification of specific metabolites in culture supernatant of Mycobacterium tuberculosis using metabolomics: exploration of potential biomarkers" - Emerging Microbes and Infections 4(1) (2015) ID e6
  

  Although previous studies have reported the use of metabolomics for Mycobacterium species differentiation, little is known about the potential of extracellular metabolites of Mycobacterium tuberculosis (MTB) as specific biomarkers. Using an optimized ultrahigh performance liquid chromatography-electrospray ionization-quadruple time of flight-mass spectrometry (UHPLC-ESI-Q-TOF-MS) platform, we characterized the extracellular metabolomes of culture supernatant of nine MTB strains and nine non-tuberculous Mycobacterium (NTM) strains (four M. avium complex, one M. bovis Bacillus Calmette-Guérin (BCG), one M. chelonae, one M. fortuitum and two M. kansasii). Principal component analysis readily distinguished the metabolomes between MTB and NTM. Using multivariate and univariate analysis, 24 metabolites with significantly higher levels in MTB were identified. While seven metabolites were identified by tandem mass spectrometry (MS/MS), the other 17 metabolites were unidentified by MS/MS against database matching, suggesting that they may be potentially novel compounds. One metabolite was identified as dexpanthenol, the alcohol analog of pantothenic acid (vitamin B5), which was not known to be produced by bacteria previously. Four metabolites were identified as 1-tuberculosinyladenosine (1-TbAd), a product of the virulence-associated enzyme Rv3378c, and three previously undescribed derivatives of 1-TbAd. Two derivatives differ from 1-TbAd by the ribose group of the nucleoside while the other likely differs by the base. The remaining two metabolites were identified as a tetrapeptide, Val-His-Glu-His, and a monoacylglycerophosphoglycerol, phosphatidylglycerol (PG) (16:0/0:0), respectively. Further studies on the chemical structure and biosynthetic pathway of these MTB-specific metabolites would help understand their biological functions. Studies on clinical samples from tuberculosis patients are required to explore for their potential role as diagnostic biomarkers

  specific, Mycobacterium tuberculosis, metabolomics, diagnosis, biomarkers

  NCBI PubMed ID: 26038762
  Publication DOI: 10.1038/emi.2015.6
  Journal NLM ID: 101594885
  Publisher: Philadelphia, PA: Taylor & Francis
  Correspondence: Lau SK ; Woo PC
  Institutions: State Key Laboratory of Emerging Infectious Diseases, Hong Kong, China, Research Centre of Infection and Immunology, The University of Hong Kong, Hong Kong, China, Carol Yu Centre for Infection, The University of Hong Kong, Hong Kong, China, Department of Microbiology, The University of Hong Kong, Hong Kong, China, Department of Pathology, The University of Hong Kong, Hong Kong, China
  Methods: MS/MS, LC-MS, ESI-QTOF-MS, cell growth, sonication, centrifugation, ion chromatography, UHPLC, PCA, PLS-DA
  
   
  
  Mycobacterium tuberculosis H37Rv ATCC 27294T, Mycobacterium tuberculosis H107, Mycobacterium tuberculosis H112, Mycobacterium tuberculosis 4777, Mycobacterium tuberculosis 2538, Mycobacterium tuberculosis 5521, Mycobacterium tuberculosis 5886, Mycobacterium tuberculosis 4067, Mycobacterium tuberculosis H506261
  CSDB ID 49307 (all data & tools)

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Structure type: monomer
Trivial name: 2'-deoxyinosine
Compound class: nucleoside

• Article ID: 9275
  Dewantari AA, Yongwattana N, Payongsri P, Seemakhan S, Borwornpinyo S, Ojida A, Wongkongkatep J "Fluorescence detection of deoxyadenosine in Cordyceps spp. by indicator displacement assay" - Molecules 25(9) (2020) ID 2045
  

  A rapid, sensitive and reliable indicator displacement assay (IDA) for specific detection of 2'- and 3'-deoxyadenosine (2'-dAde and 3'-dAde), the latter is also known as cordycepin, was established. The formation of inclusion complex between protonated acridine orange (AOH+) and cucurbit[7]uril (CB7) resulted in the hypochromic shift of fluorescent emission from 530 nm to 512 nm. Addition of cordycepin to the highly fluorescent AOH+/CB7 complex resulted in a unique tripartite AOH+/CB7/dAde complex with diminished fluorescence, and such reduction in emission intensity serves as the basis for our novel sensing system. The detection limits were 11 and 82 μM for 2'- and 3'-deoxyadenosine, respectively. The proposed method also demonstrated high selectivity toward 2'- and 3'-deoxyadenosine, owing to the inability of other deoxynucleosides, nucleosides and nucleotides commonly found in Cordyceps spp. to displace the AOH+ from the AOH+/CB7 complex, which was confirmed by isothermal titration calorimetry (ITC), UV-Visible and proton nuclear magnetic resonance (1H-NMR) spectroscopy. Our method was successfully implemented in the analysis of cordycepin in commercially available Ophiocordyceps and Cordyceps supplements, providing a novel and effective tool for quality assessment of these precious fungi with several health benefits.

  fluorescence, detection, fungi, cordycepin, acridine orange, cucurbit uril, indicator displacement assay

  NCBI PubMed ID: 32353945
  Publication DOI: 10.3390/molecules25092045
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: Dewantari AA ; Yongwattana N ; Payongsri P ; Borwornpinyo S ; Seemakhan S ; Ojida A ; Wongkongkatep J
  Institutions: Department of Biotechnology, Faculty of Science, Mahidol University, Bangkok, Thailand, Excellent Center for Drug Discovery, Faculty of Science, Mahidol University, Bangkok, Thailand, Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
  Methods: HPLC, spectrofluorometry, extraction, centrifugation, isothermal titration calorimetry
  
   
  
  Cordyceps, Ophiocordyceps
  CSDB ID 50783 (all data & tools)