Novel antiinsectan oxalicine alkaloids from two undescribed fungicolous Penicillium spp.
15-Deoxyoxalicine B (1) and decaturins A (2) and B (3) have been isolated from Penicillium decaturense and Penicillium thiersii, two previously undescribed species obtained as colonists of wood-decay fungi. The structures were determined by 2D NMR experiments and/or single-crystal X-ray diffraction analysis. These compounds are members of a rare structural class, and decaturins A and B feature a new polycyclic ring system. Decaturin B (3) exhibited potent antiinsectan activity against the fall armyworm (Spodoptera frugiperda).
Zhang
Yichao
Y
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA.
Li
Chen
C
Swenson
Dale C
DC
Gloer
James B
JB
Wicklow
Donald T
DT
Dowd
Patrick F
PF
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D018360:Crystallography, X-Ray; D007306:Insecticides / Q000737:chemistry* / Q000302:isolation & purification; D008958:Models, Molecular; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry* / Q000302:isolation & purification; D013141:Spiro Compounds / Q000737:chemistry* / Q000302:isolation & purification; D018411:Spodoptera
C474593:15-dexoyoxalicine B; D000470:Alkaloids; D007306:Insecticides; D011753:Pyrones; D013141:Spiro Compounds; C474594:decaturin A; C474595:decaturin B