Nine constituents including six xanthone-related compounds isolated from two ascomycetes, Gelasinospora santi-florii and Emericella quadrilineata, found in a screening study focused on immunomodulatory activity

Chem Pharm Bull (Tokyo). 2006 Apr;54(4):550-3. doi: 10.1248/cpb.54.550.

Abstract

Five metabolites tentatively called GS-1 (1)-5 (5) from Gelasinospora santi-florii, and four tentatively called EQ-4 (6), EQ-6 (7)-8 (9) together with 1-4 from Emericella quadrilineata have been isolated in a screening study on immunomodulatory fungal constituents. Among these nine metabolites, EQ-7 and 8 have been unknown. This time, the structures of GS-4 which has previously been isolated, EQ-7, and -8 have been determined to be (4R,4aS,9aR)-1,9a-dihydronidulalin A (4), (4S,4aR,9aR)-4a-carbomethoxy-1,4,4a,9a-tetrahydro-4,8-dihydroxy-6-methylxanthone (8), and 9-hydroxymicroperfuranone (9), respectively, and the six other metabolites have been identified. On bioassay, a dihydroxanthone, nidulalin A (1), a hexaketide, sordarial (5), and a xanthone, pinselin (7) have displayed significant immunosuppressive activities. The structure-activity relationships of these constituents have also been discussed.

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Cell Proliferation / drug effects*
  • Cells, Cultured
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / isolation & purification
  • Immunosuppressive Agents / pharmacology*
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Mice
  • Spleen / cytology
  • Spleen / metabolism
  • Structure-Activity Relationship
  • Xanthones / chemistry
  • Xanthones / isolation & purification
  • Xanthones / pharmacology*

Substances

  • Immunosuppressive Agents
  • Xanthones