Show legend Show as text

Structure type: monomer ; 387.1413 [M+Na]+
C₁₉H₂₄O₇
Trivial name: conoideoglucoside B
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 8893
  Sadorn K, Saepua S, Boonyuen N, Komwijit S, Rachtawee P, Pittayakhajonwut P "Phenolic glucosides and chromane analogs from the insect fungus Conoideocrella krungchingensis BCC53666" - Tetrahedron 2019 (1975) 3463-3471
  

  Six new compounds, named conoideoglucosides A-C and conoideochromanes A-C, together with eight known compounds, including eutypinic acid, 2,2-dimethyl-2H-1-chromene-6-carboxylic acid, (-)-luteoskyrin, (-)-4a-oxyluteoskyrin, chrysophanol, islandicin, catenarin, and (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol were isolated from the insect fungus Conoideocrella krungchingensis BCC53666. (-)-Luteoskyrin exhibited a broad range of antimicrobial activity such as antimalarial (IC50 0.51 μg/mL), antitubercular (MIC 6.25 μg/mL), antibacterial (both Gram positive; MIC 0.39-1.56 μg/mL and Gram negative; MIC 3.13-12.50 μg/mL), and antifungal (against various plant pathogens; MIC 3.13-50.00 μg/mL) activities, while (-)-4a-oxyluteoskyrin and catenarin showed weaker antibacterial activity. Moreover, eutypinic acid, (-)-luteoskyrin, (-)-4a-oxyluteoskyrin, and catenarin showed cytotoxicity against NCI-H187 cells with IC50 in a range of 0.16-17.99 μg/mL, while eutypinic acid and catenarin had no cytotoxicity against non-cancerous (Vero) cells at maximum tested concentration (50 mg/mL). The complete NMR spectral data and biological activity of the known (-)-4a-oxyluteoskyrin was also reported for the first time.

  biological activity, Conoideocrella, conoideoglucosides, conoideochromanes, (-)-4a-oxyluteoskyrin

  Publication DOI: 10.1016/j.tet.2019.05.007
  Journal NLM ID: 2984170R
  Publisher: Pergamon Press
  Correspondence: Sadorn K
  Institutions: Integrated Applied Chemistry Research Unit, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Bangkok, Thailand, Department of Chemistry, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Bangkok, Thailand, National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Pathumthani, Thailand
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, extraction, optical rotation measurement, CD, CC, cell growth, melting point determination, HR-ESI-MS, cytotoxicity assay, evaporation, antimicrobial assay, chiral HPLC
  
   
  
  Conoideocrella krungchingensis BCC53666
  CSDB ID 49658 (all data & tools)