Hydroxylated anthraquinones produced by Geosmithia species.
Geosmithia fungi are little known symbionts of bark beetles. Secondary metabolites of lilac colored species G. lavendula and other nine Geosmithia species were investigated in order to elucidate their possible role in the interactions of the fungi with environment. Hydroxylated anthraquinones (yellow, orange, and red pigments), were found to be the most abundant compounds produced into the medium during the submerged cultivation. Three main compounds were identified as 1,3,6,8-tetrahydroxyanthraquinone (1), rhodolamprometrin (1-acetyl-2,4,5,7-tetrahydroxyanthraquinone; 2), and 1-acetyl-2,4,5,7,8-pentahydroxyanthraquinone (3). Compounds 2 and 3 (representing the majority of produced metabolites) inhibited the growth of G+-bacteria Staphylococcus aureus and Bacillus subtilis with minimum inhibitory concentration of 64-512 microg/mL. Anti-inflammatory activity detected as inhibition of cyclooxygenase-2 was found only for compound 3 at 1 and 10 microg/mL. Compound 2 interfered with the morphology, compound 3 with cell-cycle dynamics of adherent mammalian cell lines.
Stodůlková
E
E
Department of Biogenesis and Biotechnology, Institute of Microbiology, Academy of Sciences of the Czech Republic v.v.i., Prague 4, Czech Republic.
Kolarík
M
M
Kresinová
Z
Z
Kuzma
M
M
Sulc
M
M
Man
P
P
Novák
P
P
Marsík
P
P
Landa
P
P
Olsovská
J
J
Chudícková
M
M
Pazoutová
S
S
Cerný
J
J
Bella
J
J
Flieger
M
M
D000818:Animals; D000880:Anthraquinones / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D001709:Biotechnology / Q000379:methods; D002453:Cell Cycle / Q000187:drug effects; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D030681:Ficus / Q000469:parasitology; D006367:HeLa Cells; D006801:Humans; D006900:Hydroxylation; D006999:Hypocreales / Q000254:growth & development / Q000378:metabolism*; D010860:Pigments, Biological / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D013172:Spores, Fungal / Q000254:growth & development / Q000378:metabolism; D013211:Staphylococcus aureus / Q000187:drug effects; D048889:Weevils / Q000382:microbiology / Q000502:physiology
C544950:1-acetyl-2,4,5,7,8-pentahydroxyanthraquinone; C544949:1-acetyl-2,4,5,7-tetrahydroxyanthraquinone; D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D016861:Cyclooxygenase Inhibitors; D010860:Pigments, Biological; C544948:1,3,6,8-tetrahydroxyanthraquinone