title: Waspergillamide A, a Nitro depsi-Tetrapeptide Diketopiperazine from an Australian Mud Dauber Wasp-Associated Aspergillus sp. (CMB-W031).
abstract: Chemical profiling of extracts from a mud dauber wasp-associated fungus, Aspergillus sp. (CMB-W031), revealed a remarkably diverse array of secondary metabolites, with many biosynthetic gene clusters being transcriptionally responsive to specific culture conditions. Chemical fractionation of a jasmine rice cultivation yielded many known fungal metabolites, including the highly cytotoxic (-)-stephacidin B and an unprecedented nonribosomal peptide synthase derived nitro depsi-tetrapeptide diketopiperazine, waspergillamide A (1). All structures were assigned by detailed spectroscopic analysis and, where appropriate, chemical degradation and Marfey's analysis.
authors.affiliation: Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland , St Lucia, Queensland 4072, Australia.
authors.forename: Michelle
authors.initials: M
authors.lastname: Quezada
authors.affiliation: Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland , St Lucia, Queensland 4072, Australia.
authors.forename: Zhuo
authors.initials: Z
authors.lastname: Shang
authors.affiliation: Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland , St Lucia, Queensland 4072, Australia.
authors.forename: Pabasara
authors.initials: P
authors.lastname: Kalansuriya
authors.affiliation: Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland , St Lucia, Queensland 4072, Australia.
authors.forename: Angela A
authors.initials: AA
authors.lastname: Salim
authors.affiliation: Microbial Screening Technologies , Smithfield, NSW 2164, Australia.
authors.forename: Ernest
authors.initials: E
authors.lastname: Lacey
authors.affiliation: Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland , St Lucia, Queensland 4072, Australia.
authors.forename: Robert J
authors.identifier: 0000-0002-8341-7754
authors.initials: RJ
authors.lastname: Capon
mesh_terms: D000818:Animals; D001230:Aspergillus / Q000737:chemistry*; D001315:Australia; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D054659:Diketopiperazines / Q000737:chemistry / Q000302:isolation & purification*; D026121:Indole Alkaloids / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D014863:Wasps / Q000382:microbiology*
chemical_list: D047630:Depsipeptides; D054659:Diketopiperazines; D026121:Indole Alkaloids; C470894:stephacidin B; C000621408:waspergillamide A