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Structure type: monomer ; 497.2749 [M-H]-
C₂₆H₄₂O₉
Trivial name: 15-hydroxy-16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid
Compound class: isopimarane diterpene glycoside
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72

• Article ID: 7074
  Shiono Y, Motoki S, Koseki T, Murayama T, Tojima M, Kimura K "Isopimarane diterpene glycosides, apoptosis inducers, obtained from fruiting bodies of the ascomycete Xylaria polymorpha" - Phytochemistry 70(7) (2009) 935-932
  

  The methanol extract of fruiting bodies of the ascomycete Xylaria polymorpha afforded three isopimarane diterpene glycosides, namely, 16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid (1), 15-hydroxy-16-α-D-mannopyranosyloxyisopimar-7-en-19-oic acid (2), and 16-α-D-glucopyranosyloxyisopimar-7-en-19-oic acid (3). Their structures were determined by spectroscopic methods and by single-crystal X-ray analysis. They showed cytotoxicity against human cancer cell lines and exhibited IC50 values ranging from 71 to 607 μM. Further studies on the cytotoxicity of these compounds against HL60 cells demonstrated that they induced apoptosis along with typical DNA fragmentation. It was observed that 2 was less active than 1 and 3.

  cytotoxicity, Isopimarane diterpenoids, Xylaria polymorpha, Ascomycete

  NCBI PubMed ID: 19467682
  Publication DOI: 10.1016/j.phytochem.2009.03.023
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: yshiono@tds1.tr.yamagata-u.ac.jp
  Institutions: Department of Bioresource Engineering, Faculty of Agriculture, Yamagata University, Tsuruoka, Japan, Laboratory of Chemical Biology, Faculty of Agriculture, Iwate University, Morioka, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, X-ray, DNA techniques, TLC, biological assays, analytical methods, enzymatic digestion, extraction, CD, HR-FAB-MS
  
   
  
  Xylaria polymorpha NBRC 33288
  CSDB ID 42160 (all data & tools)

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Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72

• 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
  
   
  
  Xylaria polymorpha
  CSDB ID 51330 (all data & tools)