Nematicidal alkaloids and related compounds produced by the fungus Penicillium cf. simplicissimum.
A new nematicidal alkaloid, peniprequinolone (1), together with the known alkaloids penigequinolones A and B (2a, 2b), 3-methoxy-4-hydroxy-4-(4'-methoxyphenyl)quinolinone (3), and 3-methoxy-4,6-dihydroxy-4-(4'-methoxyphenyl)quinolinone (4), were isolated from Penicillium cf. simplicissimum (Oudemans) Thom. Cyclopenin (5) and a compound (6a/6b) structurally related to cyclopenin also were isolated from the fungus, and their structures were established by spectroscopic analysis. The biological activities of 1, 2, 3, 4, and 5 were examined by a bioassay with root-lesion nematodes.
Kusano
M
M
Department of Agricultural Chemistry, Faculty of Agriculture, Tottori University, Japan.
Koshino
H
H
Uzawa
J
J
Fujioka
S
S
Kawano
T
T
Kimura
Y
Y
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D000969:Antinematodal Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001570:Benzodiazepinones / Q000737:chemistry / Q000494:pharmacology; D017173:Caenorhabditis elegans / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012275:Oryza / Q000469:parasitology; D021261:Parasitic Sensitivity Tests / Q000379:methods; D010407:Penicillium / Q000378:metabolism*; D018517:Plant Roots / Q000469:parasitology; D015363:Quinolones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
D000470:Alkaloids; D000969:Antinematodal Agents; D001570:Benzodiazepinones; D015363:Quinolones; C425555:penigequinolone A; C425554:peniprequinolone; C007200:cyclopenin