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- Title
Miniaturized Cultivation Profiling (MATRIX)-Facilitated Discovery of Noonazines A–C and Noonaphilone A from an Australian Marine-Derived Fungus, Aspergillus noonimiae CMB-M0339.
- Authors
Kankanamge, Sarani; Bernhardt, Paul V.; Khalil, Zeinab G.; Capon, Robert J.
- Abstract
Subjecting the Australian marine-derived fungus Aspergillus noonimiae CMB-M0339 to cultivation profiling using an innovative miniaturized 24-well plate format (MATRIX) enabled access to new examples of the rare class of 2,6-diketopiperazines, noonazines A–C (1–3), along with the known analogue coelomycin (4), as well as a new azaphilone, noonaphilone A (5). Structures were assigned to 1–5 on the basis of a detailed spectroscopic analysis, and in the case of 1–2, an X-ray crystallographic analysis. Plausible biosynthetic pathways are proposed for 1–4, involving oxidative Schiff base coupling/dimerization of a putative Phe precursor. Of note, 2 incorporates a rare meta-Tyr motif, typically only reported in a limited array of Streptomyces metabolites. Similarly, a plausible biosynthetic pathway is proposed for 5, highlighting a single point for stereo-divergence that allows for the biosynthesis of alternate antipodes, for example, the 7R noonaphilone A (5) versus the 7S deflectin 1a (6).
- Subjects
SCHIFF bases; FUNGI; ASPERGILLUS; RHODOMELACEAE; STREPTOMYCES; DIMERIZATION
- Publication
Marine Drugs, 2024, Vol 22, Issue 6, p243
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md22060243