Waspergillamide A, a Nitro depsi-Tetrapeptide Diketopiperazine from an Australian Mud Dauber Wasp-Associated Aspergillus sp. (CMB-W031)

Michelle Quezada, Zhuo Shang, Pabasara Kalansuriya, Angela A. Salim, Ernest Lacey, and Robert J. Capon

J. Nat. Prod., 2017, 80, 1192–1195.

Publication Date: February 24, 2017

https://doi.org/10.1021/acs.jnatprod.6b01062

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.

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