Structure and cytotoxicity of arnamial and related fungal sesquiterpene aryl esters.
We report on the structure elucidation of arnamial, a new Delta(2,4)-protoilludane everninate ester from the fungus Armillaria mellea, and on the apoptotic activity of arnamial as well as the cytotoxic activity of structurally related compounds on selected human cancer cells. Arnamial showed cytotoxicity against Jurkat T cells, MCF-7 breast adenocarcinoma, CCRF-CEM lymphoblastic leukemia, and HCT-116 colorectal carcinoma cells at IC50 = 3.9, 15.4, 8.9, and 10.7 microM, respectively, and the related aryl ester melledonal C showed cytotoxic activity against CCRF-CEM cells (IC50 = 14.75 microM). [1,2-13C2]Acetate feeding supports a polyketide origin of the orsellinic acid moiety of arnamial.
Pharmaceutical Biology and Biotechnology, Albert-Ludwigs-Universität, Stefan-Meier-Strasse 19, 79104 Freiburg, Germany.
Mathias
M
Misiek
Jessica
J
Williams
Kathrin
K
Schmich
Wolfgang
W
Hüttel
Irmgard
I
Merfort
Christine E
CE
Salomon
Courtney C
CC
Aldrich
Dirk
D
Hoffmeister
D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D055392:Armillaria / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004952:Esters; D005260:Female; D006801:Humans; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D000970:Antineoplastic Agents; D004952:Esters; D012717:Sesquiterpenes; C545136:arnamial