Dimeric- and trimeric sesquiterpenes from the flower of Inula japonica

Qinghao Jin; Jin Woo Lee; Hari Jang; Hye Lim Lee; Jun Gu Kim; Wanying Wu; Dongho Lee; Eun Hee Kim; Youngsoo Kim; Jin Tae Hong; Mi Kyeong Lee; Bang Yeon Hwang

doi:10.1016/j.phytochem.2018.07.008

Dimeric- and trimeric sesquiterpenes from the flower of Inula japonica

Qinghao Jin, Jin Woo Lee, Hari Jang, Hye Lim Lee, Jun Gu Kim, Wanying Wu, Dongho Lee, Eun Hee Kim, Youngsoo Kim, Jin Tae Hong, Mi Kyeong Lee, Bang Yeon Hwang

Department of Biosystems and Biotechnology

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

20 Citations (Scopus)

Abstract

An undescribed unusual sesquiterpene trimer and three sesquiterpene dimers were isolated from the flowers of Inula japonica. Their structures were elucidated by extensive analysis of 1D and 2D NMR spectroscopic data as well as HRESIMS data. Inulajaponicolide A has an undescribed carbon skeleton comprising of one xanthanolide and two guaianolide units with the linkage mode of C-11/C-3ʹ and C-11ʹ/C-1ʹʹ via a Diels-Alder cycloaddition reaction. Inulajaponicolides C and D exhibited moderate cytotoxic activity against A 549 and NCI-H460 human cancer cell lines with IC₅₀ values ranging from 8.5 to 17.8 μM. Inulajaponicolides A-D and lineariifolianoid A possessed significant inhibitory potency against nitric oxide production in LPS-induced RAW264.7 cells with IC₅₀ values ranging from 1.0 to 4.1 μM.

Original language	English
Pages (from-to)	107-113
Number of pages	7
Journal	Phytochemistry
Volume	155
DOIs	https://doi.org/10.1016/j.phytochem.2018.07.008
Publication status	Published - 2018 Nov

Keywords

Asteraceae
Cytotoxic activity
Inula japonica
Nitric oxide
Sesquiterpene trimer
Sesquiterpenes dimer

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.phytochem.2018.07.008

Cite this

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title = "Dimeric- and trimeric sesquiterpenes from the flower of Inula japonica",

abstract = "An undescribed unusual sesquiterpene trimer and three sesquiterpene dimers were isolated from the flowers of Inula japonica. Their structures were elucidated by extensive analysis of 1D and 2D NMR spectroscopic data as well as HRESIMS data. Inulajaponicolide A has an undescribed carbon skeleton comprising of one xanthanolide and two guaianolide units with the linkage mode of C-11/C-3ʹ and C-11ʹ/C-1ʹʹ via a Diels-Alder cycloaddition reaction. Inulajaponicolides C and D exhibited moderate cytotoxic activity against A 549 and NCI-H460 human cancer cell lines with IC50 values ranging from 8.5 to 17.8 μM. Inulajaponicolides A-D and lineariifolianoid A possessed significant inhibitory potency against nitric oxide production in LPS-induced RAW264.7 cells with IC50 values ranging from 1.0 to 4.1 μM.",

keywords = "Asteraceae, Cytotoxic activity, Inula japonica, Nitric oxide, Sesquiterpene trimer, Sesquiterpenes dimer",

author = "Qinghao Jin and Lee, {Jin Woo} and Hari Jang and Lee, {Hye Lim} and Kim, {Jun Gu} and Wanying Wu and Dongho Lee and Kim, {Eun Hee} and Youngsoo Kim and Hong, {Jin Tae} and Lee, {Mi Kyeong} and Hwang, {Bang Yeon}",

note = "Funding Information: This work was supported by the Medical Research Center Program ( MRC, 2017R1A5A2015541 ) through the National Research Foundation of Korea . The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

year = "2018",

month = nov,

doi = "10.1016/j.phytochem.2018.07.008",

language = "English",

volume = "155",

pages = "107--113",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - Dimeric- and trimeric sesquiterpenes from the flower of Inula japonica

AU - Jin, Qinghao

AU - Lee, Jin Woo

AU - Jang, Hari

AU - Lee, Hye Lim

AU - Kim, Jun Gu

AU - Wu, Wanying

AU - Lee, Dongho

AU - Kim, Eun Hee

AU - Kim, Youngsoo

AU - Hong, Jin Tae

AU - Lee, Mi Kyeong

AU - Hwang, Bang Yeon

N1 - Funding Information: This work was supported by the Medical Research Center Program ( MRC, 2017R1A5A2015541 ) through the National Research Foundation of Korea . The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Publisher Copyright: © 2018 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2018/11

Y1 - 2018/11

N2 - An undescribed unusual sesquiterpene trimer and three sesquiterpene dimers were isolated from the flowers of Inula japonica. Their structures were elucidated by extensive analysis of 1D and 2D NMR spectroscopic data as well as HRESIMS data. Inulajaponicolide A has an undescribed carbon skeleton comprising of one xanthanolide and two guaianolide units with the linkage mode of C-11/C-3ʹ and C-11ʹ/C-1ʹʹ via a Diels-Alder cycloaddition reaction. Inulajaponicolides C and D exhibited moderate cytotoxic activity against A 549 and NCI-H460 human cancer cell lines with IC50 values ranging from 8.5 to 17.8 μM. Inulajaponicolides A-D and lineariifolianoid A possessed significant inhibitory potency against nitric oxide production in LPS-induced RAW264.7 cells with IC50 values ranging from 1.0 to 4.1 μM.

AB - An undescribed unusual sesquiterpene trimer and three sesquiterpene dimers were isolated from the flowers of Inula japonica. Their structures were elucidated by extensive analysis of 1D and 2D NMR spectroscopic data as well as HRESIMS data. Inulajaponicolide A has an undescribed carbon skeleton comprising of one xanthanolide and two guaianolide units with the linkage mode of C-11/C-3ʹ and C-11ʹ/C-1ʹʹ via a Diels-Alder cycloaddition reaction. Inulajaponicolides C and D exhibited moderate cytotoxic activity against A 549 and NCI-H460 human cancer cell lines with IC50 values ranging from 8.5 to 17.8 μM. Inulajaponicolides A-D and lineariifolianoid A possessed significant inhibitory potency against nitric oxide production in LPS-induced RAW264.7 cells with IC50 values ranging from 1.0 to 4.1 μM.

KW - Asteraceae

KW - Cytotoxic activity

KW - Inula japonica

KW - Nitric oxide

KW - Sesquiterpene trimer

KW - Sesquiterpenes dimer

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SN - 0031-9422

VL - 155

SP - 107

EP - 113

JO - Phytochemistry

JF - Phytochemistry

ER -

Dimeric- and trimeric sesquiterpenes from the flower of Inula japonica

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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