Targeted isolation of sesquiterpene lactone dimers from Aucklandia lappa guided by LC-HRMS/MS-based molecular networking

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

doi:10.1016/j.phytochem.2022.113557

Targeted isolation of sesquiterpene lactone dimers from Aucklandia lappa guided by LC-HRMS/MS-based molecular networking

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

Department of Biosystems and Biotechnology

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

Abstract

An LC-HRMS/MS-based molecular networking strategy was applied to investigate the potential sesquiterpene dimers of Aucklandia lappa, leading to the isolation of three undescribed guaiane-guaiane dimers and one guaiane-eudesmane dimer together with six known sesquiterpenes. The structures were determined by analyzing their 1D, 2D NMR, and HRESIMS data as well as ECD calculations. The biogenetic pathway of the sesquiterpene dimers was postulated to involve the Diels-Alder cycloaddition as the key step. All compounds exhibited their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages with IC₅₀ values ranging from 0.3 to 25.1 μM.

Original language	English
Article number	113557
Journal	Phytochemistry
Volume	206
DOIs	https://doi.org/10.1016/j.phytochem.2022.113557
Publication status	Published - 2023 Feb

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MIST) (No. 2020R1A2C1008406 and 2017R1A5A2015541). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government ( MIST ) (No. 2020R1A2C1008406 and 2017R1A5A2015541 ). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.

Publisher Copyright:
© 2022 Elsevier Ltd

Keywords

Asteraceae
Aucklandia lappa
Molecular networking
Nitric oxide
Sesquiterpene lactone dimer

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

Access to Document

10.1016/j.phytochem.2022.113557

Cite this

@article{3c4b7f1531dc499cab382ded596866f6,

title = "Targeted isolation of sesquiterpene lactone dimers from Aucklandia lappa guided by LC-HRMS/MS-based molecular networking",

abstract = "An LC-HRMS/MS-based molecular networking strategy was applied to investigate the potential sesquiterpene dimers of Aucklandia lappa, leading to the isolation of three undescribed guaiane-guaiane dimers and one guaiane-eudesmane dimer together with six known sesquiterpenes. The structures were determined by analyzing their 1D, 2D NMR, and HRESIMS data as well as ECD calculations. The biogenetic pathway of the sesquiterpene dimers was postulated to involve the Diels-Alder cycloaddition as the key step. All compounds exhibited their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values ranging from 0.3 to 25.1 μM.",

keywords = "Asteraceae, Aucklandia lappa, Molecular networking, Nitric oxide, Sesquiterpene lactone dimer",

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

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MIST) (No. 2020R1A2C1008406 and 2017R1A5A2015541). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government ( MIST ) (No. 2020R1A2C1008406 and 2017R1A5A2015541 ). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2023",

month = feb,

doi = "10.1016/j.phytochem.2022.113557",

language = "English",

volume = "206",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Targeted isolation of sesquiterpene lactone dimers from Aucklandia lappa guided by LC-HRMS/MS-based molecular networking

AU - Han, Jae Sang

AU - Kim, Jun Gu

AU - Linh Le, Thi Phuong

AU - Cho, Yong Beom

AU - Lee, Dongho

AU - Hong, Jin Tae

AU - Lee, Mi Kyeong

AU - Hwang, Bang Yeon

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MIST) (No. 2020R1A2C1008406 and 2017R1A5A2015541). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government ( MIST ) (No. 2020R1A2C1008406 and 2017R1A5A2015541 ). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Publisher Copyright: © 2022 Elsevier Ltd

PY - 2023/2

Y1 - 2023/2

N2 - An LC-HRMS/MS-based molecular networking strategy was applied to investigate the potential sesquiterpene dimers of Aucklandia lappa, leading to the isolation of three undescribed guaiane-guaiane dimers and one guaiane-eudesmane dimer together with six known sesquiterpenes. The structures were determined by analyzing their 1D, 2D NMR, and HRESIMS data as well as ECD calculations. The biogenetic pathway of the sesquiterpene dimers was postulated to involve the Diels-Alder cycloaddition as the key step. All compounds exhibited their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values ranging from 0.3 to 25.1 μM.

AB - An LC-HRMS/MS-based molecular networking strategy was applied to investigate the potential sesquiterpene dimers of Aucklandia lappa, leading to the isolation of three undescribed guaiane-guaiane dimers and one guaiane-eudesmane dimer together with six known sesquiterpenes. The structures were determined by analyzing their 1D, 2D NMR, and HRESIMS data as well as ECD calculations. The biogenetic pathway of the sesquiterpene dimers was postulated to involve the Diels-Alder cycloaddition as the key step. All compounds exhibited their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages with IC50 values ranging from 0.3 to 25.1 μM.

KW - Asteraceae

KW - Aucklandia lappa

KW - Molecular networking

KW - Nitric oxide

KW - Sesquiterpene lactone dimer

UR - http://www.scopus.com/inward/record.url?scp=85144357000&partnerID=8YFLogxK

U2 - 10.1016/j.phytochem.2022.113557

DO - 10.1016/j.phytochem.2022.113557

M3 - Article

C2 - 36496006

AN - SCOPUS:85144357000

SN - 0031-9422

VL - 206

JO - Phytochemistry

JF - Phytochemistry

M1 - 113557

ER -

Targeted isolation of sesquiterpene lactone dimers from Aucklandia lappa guided by LC-HRMS/MS-based molecular networking

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this