Challenging Structure Elucidation of Lumnitzeralactone, an Ellagic Acid Derivative from the Mangrove Lumnitzera racemosa

Autor: Jonas Kappen, Jeprianto Manurung, Tristan Fuchs, Sahithya Phani Babu Vemulapalli, Lea M. Schmitz, Andrej Frolov, Andria Agusta, Alexandra N. Muellner-Riehl, Christian Griesinger, Katrin Franke, Ludger A. Wessjohann
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Marine Drugs, Vol 21, Iss 4, p 242 (2023)
Druh dokumentu: article
ISSN: 1660-3397
DOI: 10.3390/md21040242
Popis: The previously undescribed natural product lumnitzeralactone (1), 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 (1), 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 supported by computer-assisted structure elucidation (CASE system applying ACD-SE), density functional theory (DFT) calculations, and a two-step chemical synthesis. Possible biosynthetic pathways involving mangrove-associated fungi have been suggested.
Databáze: Directory of Open Access Journals