1. Academic Validation
  2. Menominin A and B: Cytotoxic Cyclodepsipeptides from the Freshwater Sponge-Associated Cyanobacterium Nostoc sp. UIC 10607

Menominin A and B: Cytotoxic Cyclodepsipeptides from the Freshwater Sponge-Associated Cyanobacterium Nostoc sp. UIC 10607

  • J Nat Prod. 2025 Feb 20. doi: 10.1021/acs.jnatprod.4c01445.
Lydia J Davis 1 2 Aleksej Krunić 1 Kelsey Alexander 1 Manead Khin 1 Jared S Wood 2 Cody Earp 3 Manuel Rangel-Grimaldo 3 Alessandra S Eustáquio 1 Joanna E Burdette 1 R Thomas Williamson 2 Nicholas H Oberlies 3 Jimmy Orjala 1
Affiliations

Affiliations

  • 1 Department of Pharmaceutical Sciences, College of Pharmacy, University of Illinois Chicago, Chicago, Illinois 60612, United States.
  • 2 Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Wilmington, North Carolina 28409, United States.
  • 3 Department of Chemistry and Biochemistry, University of North Carolina Greensboro, Greensboro, North Carolina 27412, United States.
Abstract

Menominin A (1) and B (2), two cyclodepsipeptides containing a 3,8-dihydroxy-2-methyltetradecanoic acid residue, were isolated from the freshwater sponge-associated cyanobacterium, Nostoc sp. UIC 10607, using bioactivity-guided and spectroscopic approaches. The planar structures of 1 and 2 were established using HRESIMS and one- and two-dimensional NMR experiments. Comparative genomic analysis revealed unique differences in the putative menominin biosynthetic gene cluster compared to that of the closely related cyanobacterial cyclic lipodepsipeptide, hapalosin, assisting in structure elucidation and highlighting the structural diversity of this class of compounds. Configuration assignments were determined using a combination of J-based configuration analysis, chiral HPLC, modified Mosher's ester analysis, and DFT calculations. Menominin A and B demonstrate antiproliferative bioactivity against the high-grade serous ovarian Cancer cell line OVCAR3 (IC50 = 3.1 (1) and 2.4 μM (2)). Menominin A and B are the first reported secondary metabolites from a freshwater sponge-associated cyanobacterium, underscoring the potential of freshwater sponges as a microbial culture source in natural product discovery.

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