title: Haenamindole and fumiquinazoline analogs from a fungicolous isolate of Penicillium lanosum.
abstract: Three amino acid-derived compounds, haenamindole (1) and 2'-epi-fumiquinazolines C (2) and D (3), were isolated from cultures of a fungicolous isolate of Penicillium lanosum (MYC-1813=NRRL 66231). Compound 1 was also encountered in cultures of P. corylophilum (MYC-418=NRRL 28126). Structure elucidation of these metabolites was based mainly on high resolution mass spectrometry and NMR data analysis. Haenamindole (1) was found to be a recently reported diketopiperazine-type metabolite that incorporates an unusual β-Phe unit. Analysis of X-ray crystallographic data and the products of acid hydrolysis of 1 enabled a conclusive, slightly modified stereochemical assignment for haenamindole. Fumiquinazoline analog 2 is a new natural product, while related compound 3 has been previously reported only as a product of an in vitro enzymatic step and of a genetically engineered fungal culture. Compounds 1 and 3 showed antiinsectan activity against the fall armyworm Spodoptera frugiperda.
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, IA, USA.
authors.forename: In Hyun
authors.initials: IH
authors.lastname: Hwang
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, IA, USA.
authors.forename: Yongsheng
authors.initials: Y
authors.lastname: Che
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, IA, USA.
authors.forename: Dale C
authors.initials: DC
authors.lastname: Swenson
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, IA, USA.
authors.forename: James B
authors.initials: JB
authors.lastname: Gloer
authors.affiliation: Bacterial Foodborne Pathogens and Mycology Research Unit, Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL, USA.
authors.forename: Donald T
authors.initials: DT
authors.lastname: Wicklow
authors.affiliation: Mycotoxin Prevention and Applied Microbiology Research Unit, Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL, USA.
authors.forename: Stephen W
authors.initials: SW
authors.lastname: Peterson
authors.affiliation: Crop Bioprotection Research Unit, Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL, USA.
authors.forename: Patrick F
authors.initials: PF
authors.lastname: Dowd
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D054659:Diketopiperazines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010407:Penicillium / Q000737:chemistry*; D011799:Quinazolines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018411:Spodoptera / Q000187:drug effects*
chemical_list: D054659:Diketopiperazines; D007306:Insecticides; D011799:Quinazolines; C454622:fumiquinazoline C; C000612925:haenamindole