Molecular Networking-Guided Isolation of Cycloartane-type Triterpenoids from Curculigo orchioides and Their Inhibitory Effect on Nitric Oxide Production

Abstract

The MolNetEnhancer workflow was applied to molecular networking analysis of the CH 2 Cl 2 -soluble fraction of the rhizomes of Curculigo orchioides , which showed a potent inhibitory effect on the lipopolysaccharide (LPS)-induced nitric oxide production. Among the molecular network, clusters of cycloartane-type triterpenoids were classified using the ClassyFire module of MolNetEnhancer, and their structures were predicted by the in silico fragment analysis tool, Network Annotation Propagation (NAP). Using mass spectrometry (MS)-guided isolation methods, six cycloartane-type triterpenoids ( 1 – 6 ) were isolated, and their structures were elucidated based on the interpretation of NMR, HRESIMS, and single-crystal X-ray diffraction. Among the isolates, compounds 1 and 4 , which have an α,β-unsaturated carbonyl moiety on the A-ring, exhibited significant inhibitory effects on LPS-induced nitric oxide production in RAW264.7 cells with IC 50 values of 12.4 and 11.8 μM, respectively.

Molecular Networking-Guided Isolation of a Phenolic Constituent from Prunus mume Seed and Its Antioxidant and Anti-Inflammatory Activities

“…Network Annotation Propagation (NAP) and the Mass2Motifs LDA parameter (MS2LDA) can be used to improve the accuracy of candidate prediction and discover unsupervised substructure pattern in MS data [ 12 , 13 , 14 ]. Outputs from MN, NAP, and MS2LDA can be integrated using MolNetEnhancer workflow, which provides a more extensive chemical overview of metabolomics data through the Classyfire automatic classification module [ 15 , 16 , 17 , 18 ].…”

Cytotoxicity and Identification of Antibacterial Compounds from Baillonella toxisperma Bark Using a LC-MS/MS and Molecular Networking Approach

“…One of the few studies that isolated a compound (3-hydroxy uridine, a plant growth inhibitor) was performed by Hajime et al [ 13 ]. Thus, in the present study, we propose a molecular networking (MN) dereplication approach based on high-resolution liquid chromatography/mass spectrometry (LC-HRMS/MS) data to more efficiently and rapidly target compounds present in the ethanolic extracts of B. toxisperma [ 14 ]. Molecular networking (MN) is a valuable tool for revealing the metabolomes of plants, humans, microorganisms and animals [ 15 ].…”