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Targeted isolation of two disesquiterpenoid macrocephadiolides A and B from Ainsliaea macrocephala using a molecular networking-based dereplication strategy

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Abstract

A molecular networking-based dereplication strategy was applied for the phytochemical investigation of Ainsliaea macrocephala, leading to the isolation of two novel disesquiterpenoid macrocephadiolides A (1) and B (2). Their structures, featuring a rare 5,6-spirocyclic ketal lactone core and a C-15/C-15′ linkage between a guaianolide and a 3,4-seco-guaianolide monomer, respectively, were established by extensive spectroscopic analysis and confirmed further by single-crystal X-ray crystallography. Compounds 1 and 2 showed a potent inhibitory effect on nitric oxide (NO) production, with IC50 values of 0.99 and 6.13 μM, respectively, in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Compound 1 dose-dependently suppressed the expression of inducible NO oxidase (iNOS) through inhibiting nuclear factor-κB (NF-κB) activation.

Graphical abstract: Targeted isolation of two disesquiterpenoid macrocephadiolides A and B from Ainsliaea macrocephala using a molecular networking-based dereplication strategy

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Article information


Submitted
07 Jan 2020
Accepted
08 May 2020
First published
09 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Targeted isolation of two disesquiterpenoid macrocephadiolides A and B from Ainsliaea macrocephala using a molecular networking-based dereplication strategy

Y. Ren, S. Zhou, T. Zhang, M. Qian, R. Zhang, S. Yao, H. Zhu, C. Tang, L. Lin and Y. Ye, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00030B

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