Chasing molecules - a structure elucidation journey

Monday, 03/July/2023 11:30am - 11:45am
ID: 135 / Session 2
Oral Presentation

Chasing molecules - a structure elucidation journey

Jonas Kappen

Leibniz Institute of Plant Biochemistry (IPB), Halle (Saale), Germany; jkappen@ipb-halle.de

The novel natural product lumnitzeralactone, which represents a derivative of ellagic acid, was isolated from the anti-bacterial extract of the Indonesian mangrove species Lumnitzera racemosa Willd. The structure of lumnitzeralactone, a proton-deficient and highly challenging condensed aromatic ring system, was unambiguously elucidated by extensive spectroscopic analyses involving high-resolution mass spectrometry (HRMS), 1D 1H and 13C nuclear magnetic resonance spectroscopy (NMR), and 2D NMR (including 1,1-ADEQUATE and 1,n-ADEQUATE). Determination of the structure was a.o. supported by a two-step chemical synthesis.

References

Kappen, J.; Manurung, J.; Fuchs, T.; Vemulapalli, S.P.B.; Schmitz, L.M.; Frolov, A.; Agusta, A.; Muellner-Riehl, A.N.; Griesinger, C.; Franke, K.; et al. Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove Lumnitzera racemosa. Mar. Drugs 2023, 21, 242. https://doi.org/10.3390/md21040242

Manurung, J.; Kappen, J.; Schnitzler, J.; Frolov, A.; Wessjohann, L.A.; Agusta, A.; Muellner-Riehl, A.N.; Franke, K. Analysis of Unusual Sulfated Constituents and Anti-infective Properties of Two Indonesian Mangroves, Lumnitzera littorea and Lumnitzera racemosa (Combretaceae). Separations 2021, 8, 82. https://doi.org/10.3390/separations8060082