Millmerranones A-F: A Meroterpene Cyclic Carbonate and Related Metabolites from the Australian Fungus Aspergillus sp. CMB-MRF324

  • Org Lett. 2021 Nov 5;23(21):8424-8428. doi: 10.1021/acs.orglett.1c03150.
Taizong Wu  1 ,  Angela A Salim  1 ,  Robert J Capon  1
Affiliations
  • 1. Institute for Molecular Bioscience, The University of Queensland, Brisbane, Queensland 4072, Australia.
PMID: 34636579 DOI: 10.1021/acs.orglett.1c03150
Abstract

A brown rice cultivation of Aspergillus sp. CMB-MRF324 yielded six new meroterpenes, millmerranones A-F (1-6), and four known analogues, terreulactones A-D (7-10). Millmerranone A (1) possesses a unique carbon skeleton bearing a rare cyclic carbonate and undergoes an unprecedented base mediated rearrangement to seco-millmerranone A (1a). We also report on an unexpected base rearrangement of 7 to 7a/b; a plausible biosynthetic relationship linking 1, 7, and 9; and acetylcholinesterase inhibitory properties (IC50 37 nM to >30 μM).

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