Xanthone derivatives from the fermentation products of an endophytic fungus Phomopsis sp

Fitoterapia. 2013 Dec:91:189-193. doi: 10.1016/j.fitote.2013.09.004. Epub 2013 Sep 13.

Abstract

Three new xanthones, 1,5-dihydroxy-3-hydroxyethyl-6-methoxycarbonylxanthone (1), 1-hydroxy-5- methoxy-3-hydroxyethyl-6-methoxycarbonylxanthone (2), and 1-hydroxy-3-hydroxyethyl- 8-ethoxycarbonylxanthone (3), along with seven known xanthones (4-10) were isolated from the fermentation products of an endophytic fungus Phomopsis sp.. Their structures were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques. Compounds 1-10 were also tested for their cytotoxicity against five human tumor cell lines (NB4, A549, SHSY5Y, PC3, and MCF7) by MTT method using paclitaxel as positive control. Compounds 1 and 3 showed cytotoxicity against A549 cell lines with IC50 values of 3.6 and 2.5 μM, respectively. In addition, 1 was cytotoxic to MCF7 cells with IC50 value of 2.7 μM.

Keywords: 1,5-dihydroxy-3-hydroxyethyl-6-methoxycarbonylxanthone;1-hydroxy-5-methoxy-3-hydroxyethyl-6-methoxycarbonylxanthone;1-hydroxy-3-hydroxyethyl-8-ethoxycarbonylxanthone; 1,7-dihydroxy-2-methoxy-3-(3-methylbut-2-enyl)xanthone;1-hydroxy-4,7-dimethoxy-6-(3-oxobutyl) xanthone; 6-O- methyl-2-deprenylrheediaxanthone B; Asperxanthone (PubChem CID: 5748546); Cytotoxicity; Phomopsis sp; Pinselin (PubChem CID: 5377796); Secosterigmatocystin; Structure elucidation; Xanthones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Antineoplastic Agents / therapeutic use
  • Ascomycota / chemistry*
  • Biological Products / chemistry*
  • Biological Products / pharmacology
  • Biological Products / therapeutic use
  • Cell Line, Tumor
  • Endophytes / chemistry
  • Fermentation
  • Humans
  • Inhibitory Concentration 50
  • MCF-7 Cells
  • Molecular Structure
  • Neoplasms / drug therapy*
  • Xanthones / chemistry
  • Xanthones / isolation & purification*
  • Xanthones / pharmacology
  • Xanthones / therapeutic use

Substances

  • 1,5-dihydroxy-3-hydroxyethyl-6-methoxycarbonylxanthone
  • 1-hydroxy-3-hydroxyethyl-8-ethoxycarbonylxanthone
  • Antineoplastic Agents
  • Biological Products
  • Xanthones