Neopetrotaurines A–C, Isoquinoline Alkaloids with an Unprecedented Taurine Bridge from the Sponge Neopetrosia sp

• DOI: 10.1021/acs.jnatprod.3c01041
• Publication Date: 2024-01-31T16:41:15Z
• Authors: Dongdong Wang; Wei Jiang; Mehal Churiwal; Katrina Jia; Sarath P. D. Sena...; Heidi R. Bokesch; Girma M. Woldemic...; Yong Kim; Robert G. Hawley; Jun S. Wei; Javed Khan; Barry R. O’Keefe; John A. Beutler; Kirk R. Gustafson
• Keywords: Heteronuclear molecule; Isoquinoline; Sponge

Neopetrotaurines A–C (1–3), unusual alkaloids possessing two isoquinoline-derived moieties that are linked via a unique taurine bridge, were isolated from Neopetrosia sp. marine sponge. These new compounds have proton-deficient structural scaffolds difficult to unambiguously assign using only conventional 2- and 3-bond 1H–13C 1H–15N heteronuclear correlation data. Thus, the application of LR-HSQMBC HMBC NMR experiments optimized detect 4- 5-bond long-range correlations facilitated structure elucidation these taurine-bridged metabolites. (1–3) showed significant inhibition transcription driven by oncogenic fusion protein PAX3-FOXO1, which is associated with alveolar rhabdomyosarcoma, cytotoxic activity against PAX3-FOXO1-positive cell lines.