Isolation and structure elucidation by LC-MS-SPE/NMR: PR toxin- and cuspidatol-related eremophilane sesquiterpenes from Penicillium roqueforti.
Three eremophilane sesquiterpenes (1, 2, and 3) were isolated from Penicillium roqueforti DAOM 232127, and their structures were established. The new (3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one (3) is a likely biosynthetic precursor of PR toxin. 1-Hydroxyeremophil-7(11),9(10)-dien-8-one (1) is related to the immunosuppressant cuspidatol. The application of semihyphenated LC-MS-SPE/NMR to rapidly identify, purify, and elucidate the structures of 1, 2, and 3 is described.
Sørensen
Dan
D
Merck Frosst Centre for Therapeutic Research, Merck Frosst Canada Ltd., 16711 Trans Canada Highway, Kirkland, Québec, H9H 3L1, Canada. dan_sorensen@merck.com
Raditsis
Annie
A
Trimble
Laird A
LA
Blackwell
Barbara A
BA
Sumarah
Mark W
MW
Miller
J David
JD
D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
C517727:(3S)-3-acetoxyeremophil-1(2),7(11),9(10)-trien-8-one; C517726:(3S)-3-acetoxyeremophil-7(11),9(10)-dien-8-one; C517725:1-hydroxyeremophil-7(11),9(10)-dien-8-one; D009284:Naphthols; D012717:Sesquiterpenes; C015483:PR Toxin