期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 36, 页码 19609-19613出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202103878
关键词
alkaloids; building blocks-based molecular network; natural products; neuronal differentiation; structure elucidation
资金
- National Natural Science Foundation of China [81630095, 81803379]
- National Mega-Project for Innovative Drugs [2019ZX09735002]
- Science & Technology Key Project of Guangdong Province [2020B1111110004]
- Local Innovative & Research Teams Project of Guangdong Pearl River Talents Program [2017BT01Y036]
This study utilized a novel BBMN strategy to identify three SEAs compounds with unique chemical structures in the total alkaloid fraction of Flueggea suffruticosa. These compounds include a previously unseen octacyclic compound and two highly modified SEA dimers.
A combined strategy of building blocks recognition and molecular network construction, termed the building blocks-based molecular network (BBMN), was first presented to facilitate the efficient discovery of novel natural products. By mapping the BBMN of the total alkaloid fraction of Flueggea suffruticosa, three Securinega alkaloids (SEAs) with unusual chemical architectures, suffranidines A-C (1-3), were discovered and isolated. Compound 1 characterizes an unprecedented 8/5/6/5/6/6/6/6-fused octacyclic scaffold with a unique cage-shaped 3-azatricyclo[6.4.0.0(3,11)]dodecane core. Compounds 2 and 3 are highly modified SEA dimers that incorporate additional C6 motifs. A hypothetical biosynthetic pathway for 1-3 was proposed. In addition, 1 significantly induced neuronal differentiation and neurite extension by upregulating eukaryotic elongation factor 2 (eEF2)-mediated protein synthesis.
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