Issue 70, 2020

Molecular networking assisted discovery and biosynthesis elucidation of the antimicrobial spiroketals epicospirocins

Abstract

Two pairs of dibenzospiroketal racemates, (±)-epicospirocin A (1a/1b) and (±)-1-epi-epicospirocin A (2a/2b), and two (+)-enantiomers of aspermicrones, ent-aspermicrone B (3b) and ent-aspermicrone C (4b), together with two hemiacetal epimeric mixtures, epicospirocin B/1-epi-epicospirocin B (5/6) and epicospirocin C/1-epi-epicospirocin C (7/8), were investigated from the phytopathogenic fungus Epicoccum nigrum 09116 via MS/MS molecular networking guided isolation and chiral separation for the first time. A plausible epicospirocin biosynthetic pathway was elucidated through in silico gene function annotation together with knock-out experiments. This is the first report that has applied MS/MS molecular networking to identify intermediates correlated with a biosynthetic pathway.

Graphical abstract: Molecular networking assisted discovery and biosynthesis elucidation of the antimicrobial spiroketals epicospirocins

Supplementary files

Article information

Article type
Communication
Submitted
07 Jun 2020
Accepted
20 Jul 2020
First published
23 Jul 2020

Chem. Commun., 2020,56, 10171-10174

Molecular networking assisted discovery and biosynthesis elucidation of the antimicrobial spiroketals epicospirocins

G. Zhu, C. Hou, W. Yuan, Z. Wang, J. Zhang, L. Jiang, L. Karthik, B. Li, B. Ren, K. Lv, W. Lu, Z. Cong, H. Dai, T. Hsiang, L. Zhang and X. Liu, Chem. Commun., 2020, 56, 10171 DOI: 10.1039/D0CC03990J

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