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

doi:10.1021/acsomega.2c03243

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

Department of Biosystems and Biotechnology

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

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 language	English
Pages (from-to)	26853-26862
Number of pages	10
Journal	ACS Omega
Volume	7
Issue number	30
DOIs	https://doi.org/10.1021/acsomega.2c03243
Publication status	Published - 2022 Aug 2

Bibliographical note

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.

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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title = "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 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.",

author = "Kim, {Jun Gu} and Le, {Thi Phuong Linh} and Han, {Jae Sang} and Cho, {Yong Beom} and Dongho Lee and Lee, {Mi Kyeong} and Hwang, {Bang Yeon}",

note = "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: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

year = "2022",

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doi = "10.1021/acsomega.2c03243",

language = "English",

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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.

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

Abstract

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