Molecular Networking-Guided Isolation of Cycloartane-type Triterpenoids from Curculigo orchioides and Their Inhibitory Effect on Nitric Oxide Production.
Jun Gu KimThi Phuong Linh LeJae Sang HanYong Beom ChoDongho LeeMi-Kyeong LeeBang Yeon HwangPublished in: ACS omega (2022)
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.
Keyphrases
- lps induced
- nitric oxide
- inflammatory response
- high resolution
- mass spectrometry
- nitric oxide synthase
- hydrogen peroxide
- induced apoptosis
- multiple sclerosis
- liquid chromatography
- single molecule
- toll like receptor
- ms ms
- oxidative stress
- immune response
- cell cycle arrest
- solid state
- molecular docking
- room temperature
- molecular dynamics simulations
- capillary electrophoresis
- cell proliferation
- crystal structure