Polyacetylenes from the roots of Cirsium japonicum var. ussuriense

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

doi:10.1016/j.phytochem.2022.113319

Polyacetylenes from the roots of Cirsium japonicum var. ussuriense

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

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

4 Citations (Scopus)

Abstract

Eight previously undescribed polyacetylenes, cirussurynes A-H, were isolated from the methanolic extract of the roots of Cirsium japonicum var. ussuriense. Their structures were elucidated by interpretation of extensive 1D and 2D NMR spectroscopy and HRESIMS spectrometry data. The configuration of triols in cirussurynes A, B, and E-G was deduced by the J-value based configuration analysis together with specific rotation values. All compounds were evaluated for their inhibitory effects on nitric oxide production against LPS-induced RAW 264.7 macrophages, and exhibited IC₅₀ values ranging from 5.5 to 68.7 μM.

Original language	English
Article number	113319
Journal	Phytochemistry
Volume	202
DOIs	https://doi.org/10.1016/j.phytochem.2022.113319
Publication status	Published - 2022 Oct

Bibliographical note

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

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

Publisher Copyright:
© 2022 Elsevier Ltd

Keywords

Asteraceae
Cirsium japonicum var. ussuriense
Nitric oxide
Polyacetylene
Structure elucidation

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Plant Science
Horticulture

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10.1016/j.phytochem.2022.113319

Cite this

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title = "Polyacetylenes from the roots of Cirsium japonicum var. ussuriense",

abstract = "Eight previously undescribed polyacetylenes, cirussurynes A-H, were isolated from the methanolic extract of the roots of Cirsium japonicum var. ussuriense. Their structures were elucidated by interpretation of extensive 1D and 2D NMR spectroscopy and HRESIMS spectrometry data. The configuration of triols in cirussurynes A, B, and E-G was deduced by the J-value based configuration analysis together with specific rotation values. All compounds were evaluated for their inhibitory effects on nitric oxide production against LPS-induced RAW 264.7 macrophages, and exhibited IC50 values ranging from 5.5 to 68.7 μM.",

keywords = "Asteraceae, Cirsium japonicum var. ussuriense, Nitric oxide, Polyacetylene, Structure elucidation",

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

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

year = "2022",

month = oct,

doi = "10.1016/j.phytochem.2022.113319",

language = "English",

volume = "202",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd",

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AU - Lee, Seung Hyun

AU - Kim, Jun Gu

AU - Le, Thi Phuong Linh

AU - Han, Jae Sang

AU - Cho, Yong Beom

AU - Lee, Mi Kyeong

AU - Lee, Dongho

AU - Hwang, Bang Yeon

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

PY - 2022/10

Y1 - 2022/10

N2 - Eight previously undescribed polyacetylenes, cirussurynes A-H, were isolated from the methanolic extract of the roots of Cirsium japonicum var. ussuriense. Their structures were elucidated by interpretation of extensive 1D and 2D NMR spectroscopy and HRESIMS spectrometry data. The configuration of triols in cirussurynes A, B, and E-G was deduced by the J-value based configuration analysis together with specific rotation values. All compounds were evaluated for their inhibitory effects on nitric oxide production against LPS-induced RAW 264.7 macrophages, and exhibited IC50 values ranging from 5.5 to 68.7 μM.

AB - Eight previously undescribed polyacetylenes, cirussurynes A-H, were isolated from the methanolic extract of the roots of Cirsium japonicum var. ussuriense. Their structures were elucidated by interpretation of extensive 1D and 2D NMR spectroscopy and HRESIMS spectrometry data. The configuration of triols in cirussurynes A, B, and E-G was deduced by the J-value based configuration analysis together with specific rotation values. All compounds were evaluated for their inhibitory effects on nitric oxide production against LPS-induced RAW 264.7 macrophages, and exhibited IC50 values ranging from 5.5 to 68.7 μM.

KW - Asteraceae

KW - Cirsium japonicum var. ussuriense

KW - Nitric oxide

KW - Polyacetylene

KW - Structure elucidation

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SN - 0031-9422

VL - 202

JO - Phytochemistry

JF - Phytochemistry

M1 - 113319

ER -

Polyacetylenes from the roots of Cirsium japonicum var. ussuriense

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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