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Discovery of Neuritogenic Securinega Alkaloids from Flueggea suffruticosa by a Building Blocks‐Based Molecular Network Strategy
Author(s) -
He QiFang,
Wu ZhenLong,
Li Liuren,
Sun WanYang,
Wang GuiYang,
Jiang RenWang,
Hu LiJun,
Shi Lei,
He RongRong,
Wang Ying,
Ye WenCai
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202103878
Subject(s) - chemistry , stereochemistry
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.