Discovery of ianthelliformisamines D-G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

Sasha Hayes; Yaoying Lu; Bernd H A Rehm; Rohan A Davis

doi:10.3762/bjoc.20.266

Discovery of ianthelliformisamines D-G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

Beilstein J Org Chem. 2024 Dec 9:20:3205-3214. doi: 10.3762/bjoc.20.266. eCollection 2024.

Authors

Sasha Hayes^{1

2}, Yaoying Lu^{1

3}, Bernd H A Rehm^{1

3}, Rohan A Davis^{1

2}

Affiliations

¹ Institute for Biomedicine and Glycomics, Griffith University, Don Young Road, Brisbane, 4111, Australia.
² NatureBank, Griffith University, Don Young Road, Brisbane, 4111, Australia.
³ Centre for Cell Factories and Biopolymers, Griffith University, Don Young Road, Brisbane, 4111, Australia.

Abstract

The marine sponge Suberea ianthelliformis was investigated for new chemistry after the recent discovery that polyamines ianthelliformisamines A-C (1-3) - originally sourced from this Australian sponge - act as Pseudomonas aeruginosa biofilm inhibitors and antibiotic enhancers. Large-scale extraction and isolation studies resulted in the discovery of four new and minor natural products, ianthelliformisamines D-G (4-7) and the known steroid, aplysterol (8). Compounds 4-7 were fully characterised following 1D/2D NMR, MS and UV data analyses. All compounds were assessed for their inhibition on planktonic growth of P. aeruginosa PAO1 in addition to their ability to inhibit the formation of biofilms. None of the tested natural products inhibited planktonic growth or biofilm formation of PAO1 when screened at 50 µM. Ianthelliformisamine D (4) contains a rare N-(3-aminopropyl)-2-pyrrolidone moiety only found in <30 natural products. Owing to the novelty of compound 4, we undertook the first total synthesis of this natural product, which was achieved in three steps.

Keywords: Pseudomonas; Suberea; ianthelliformisamine; marine sponge; natural products; total synthesis.

Grants and funding

The authors acknowledge the Australian Research Council (ARC) for support toward NMR and MS equipment (grants LE0668477, LE140100119, and LE0237908). S.H. acknowledges Griffith University for Ph.D. scholarship support.