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Structure type: monomer ; 503.2852 [M+H]+
C₂₅H₄₂O₁₀
Trivial name: akanthopyrone C
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 7708
  Kuephadungphan W, Helaly SE, Daengrot C, Phongpaichit S, Luangsa-ard JJ, Rukachaisirikul V, Stadler M "Akanthopyrones A-D, α-pyrones bearing a 4-O-methyl-β-D-glucopyranose moiety from the spider-associated ascomycete Akanthomyces novoguineensis" - Molecules 22(7) (2017) e1202
  

  Hypocrealean fungi have proved to be prolific bioactive metabolite producers; they have caught the attention of mycologists throughout the world. However, only a few studies on the insect and spider parasitic genus Akanthomyces have so far been carried out. In this study, we report the isolation, structural elucidation and biological activities of four unprecedented glycosylated α-pyrone derivatives, akanthopyrones A-D (1-4), from a culture of Akanthomyces novoguineensis collected in Thailand. The chemical structures of the akanthopyrones were determined by extensive 1D- and 2D-NMR, and HRMS spectroscopic analysis. Their absolute configurations were determined. Akanthopyrone A (1) exhibited weak antimicrobial activity against Bacillus subtilis DSM10 and cytotoxicity against the HeLa cell line KB-3-1, while akanthopyrone D (4) showed weak activity against Candida tenuis MUCL 29892.

  Hypocreales, cordycipitaceae, invertebrate-associated fungi, α-pyrones, 4-O-methy-β-D-glucopyranose, 4-O-methyl-β-D-glucopyranose

  NCBI PubMed ID: 28718819
  Publication DOI: 10.3390/molecules22071202
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: marc.stadler@helmholtz-hzi.de
  Institutions: Department of Microbial Drugs, Helmholtz Centre for Infection Research, Braunschweig, Germany, Department of Chemistry, Faculty of Science, Aswan University, Aswan, Egypt, Department of Microbiology, Faculty of Science, Prince of Songkla University, Songkhla, Thailand, National Centre for Genetic Engineering and Biotechnology (BIOTEC), Pathumthani, Thailand, Department of Chemistry, Faculty of Science, Prince of Songkla University, Songkhla, Thailand, Center of Excellence for Innovation in Chemistry, Prince of Songkla University, Songkhla, Thailand, Natural Products Research Center of Excellence, Prince of Songkla University, Songkhla, Thailand
  Methods: 13C NMR, 1H NMR, acid hydrolysis, HPLC-MS, HR-ESI-MS, HMBC, COSY, NOESY, HSQC, HRMS, LCMS
  
   
  
  Akanthomyces novoguineensis BCC47894
  CSDB ID 43268 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: akanthopyrone C
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 6181
  Hussain H, Mamadalieva NZ, Ali I, Elizbit, Green IR, Wang D, Zou L, Simal-Gandara J, Cao H, Xiao J "Fungal glycosides: Structure and biological function" - Trends in Food Science and Technology 110 (2021) 611-651
  

  Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target. Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units. Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.

  glycoside, antimicrobial, fungi, food preservative, secondary metabolites

  Publication DOI: 10.1016/j.tifs.2021.02.029
  Journal NLM ID: 9426004
  Publisher: Cambridge, UK: Elsevier Trends Journals
  Correspondence: Hussain H ; Hussain H ; Xiao J ; Xiao J
  Institutions: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Halle (Saale), Germany, Institute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent, Uzbekistan, School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan, China, Department Materials Engineering, National University of Sciences and Technology (NUST) H12, Islamabad, Pakistan, Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland, South Africa, Key Laboratory of Coarse Cereal Processing, Ministry of Agriculture and Rural Affairs, Chengdu University, Chengdu, China, Nutrition and Bromatology Group, Department of Analytical Chemistry and Food Science, Faculty of Food Science and Technology, University of Vigo - Ourense Campus, Ourense, Spain
  
   
  
  Akanthomyces novoguineensis
  CSDB ID 51247 (all data & tools)