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Structure type: monomer ; 491.2987 [M+Na]+
C₂₆H₄₄O₇
Trivial name: Phaeoside
Compound class: glycoside
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 7783
  Kenmoku H, Sugai T, Yajima H, Sassa T "Phaeoside, a novel galactoside of hydroxymanoyl oxide from the gibberellin A1-producing Phaeosphaeria sp. L487" - Bioscience, Biotechnology, and Biochemistry 68(11) (2004) 2418–2420
  

  Isolation and examination of a diterpene glycoside from the culture filtrate of the gibberellin A(1)-producing Phaeosphaeria sp. L487 allowed us to identify a novel fungal galactoside of hydroxymanoyl oxide together with (-)-ent-13-epi-manoyl oxide. It was designated phaeoside and determined to be 1α-hydroxy-ent-13-epi-manoyl oxide 1-O-β-D-galactopyranoside based on its chemical degradation and spectroscopic methods. This is the first report of the isolation of a diterpene galactoside from fungi.

  galactoside, fungal metabolite, Phaeosphaeria sp. L487, phaeoside, manoyl oxide

  NCBI PubMed ID: 15564689
  Publication DOI: 10.1271/bbb.68.2418
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Institutions: Department of Bioresource Engineering, Faculty of Agriculture, Yamagata University, Tsuruoka, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, GC, methanolysis, HPLC, extraction, optical rotation measurement, CC, cell growth, HR-FAB-MS
  
   
  
  Phaeosphaeria sp. L487
  CSDB ID 45604 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: phaeoside
Compound class: glycoside
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• 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
  
   
  
  Phaeosphaeria sp. L487
  CSDB ID 51339 (all data & tools)