TY - JOUR
T1 - Molecular Networking-Guided Isolation of Cycloartane-type Triterpenoids from Curculigo orchioides and Their Inhibitory Effect on Nitric Oxide Production
AU - Kim, Jun Gu
AU - Le, Thi Phuong Linh
AU - Han, Jae Sang
AU - Cho, Yong Beom
AU - Lee, Dongho
AU - Lee, Mi Kyeong
AU - Hwang, Bang Yeon
N1 - Funding Information:
This study was supported by a National Research Foundation of Korea (NRF) grant funded by the Korean government (MIST) (No. 2020R1A2C1008406). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.
Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/8/2
Y1 - 2022/8/2
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85136204962&partnerID=8YFLogxK
U2 - 10.1021/acsomega.2c03243
DO - 10.1021/acsomega.2c03243
M3 - Article
AN - SCOPUS:85136204962
VL - 7
SP - 26853
EP - 26862
JO - ACS Omega
JF - ACS Omega
SN - 2470-1343
IS - 30
ER -