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

Jun Gu Kim, Thi Phuong Linh Le, Jae Sang Han, Yong Beom Cho, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang

Research output: Contribution to journalArticlepeer-review

Abstract

The MolNetEnhancer workflow was applied to molecular networking analysis of the CH2Cl2-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 IC50values of 12.4 and 11.8 μM, respectively.

Original languageEnglish
Pages (from-to)26853-26862
Number of pages10
JournalACS Omega
Volume7
Issue number30
DOIs
Publication statusPublished - 2022 Aug 2

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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