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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Mycotoxin Prevention and Applied Microbiology Research » Research » Publications at this Location » Publication #323031
Title: Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum

Author
item HWANG, HYUN - University Of Iowa
item CHE, YONGSHENG - University Of Iowa
item SWENSON, DALE - University Of Iowa
item GLOER, JAMES - University Of Iowa
item Wicklow, Donald
item Peterson, Stephen
item Dowd, Patrick

Submitted to: Journal of Antibiotics
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/30/2016
Publication Date: 6/22/2016
Citation: Hwang, I.H., Che, Y., Swenson, D.C., Gloer, J.B., Wicklow, D.T., Peterson, S.W., Dowd, P.F. 2016. Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum. Journal of Antibiotics. 69(8):631-636.

Interpretive Summary: The fall armyworm is a perennial pest of corn often causing significant losses to corn farmers. We screened fall army worms for reactivity to chemical extracts from novel fungi isolated in diverse habitats. A mold isolate from Hawaii caused death among the fall armyworms tested in the laboratory. The chemical mold extract was further examined to determine what chemical might be causing the death of the insect. Two previously unknown compounds that kill fall armyworms were identified and their structures determined. This will be of interest to insecticide producers and academic chemists.

Technical Abstract: Two new amino acid-derived compounds, lanosindole (1) and 2'-epi-fumiquinazoline C (2), were isolated from cultures of a fungicolous isolate of Penicillium lanosum (MYC 1813 = NRRL 66231), together with 2'-epi-fumiquinazoline D (3), previously reported only as a product of an in vitro enzymatic step and of a genetically engineered fungal culture. Structure elucidation of these metabolites was based mainly on HRMS and NMR data analysis, which enabled identification of an unusual ß-Phe unit in 1. X-ray crystallographic analysis of 1 confirmed its structure and enabled assignment of relative configuration. The absolute configuration of 1 was determined by analysis of the products of acid hydrolysis. Compounds 1 and 3 showed antiinsectan activity against the fall armyworm Spodoptera frugiperda.