Tetrahydroprotoberberine N-oxides from Chelidonium majus and their inhibitory effects on NO production in RAW 264.7 cells

Thi Phuong Linh Le; Jin Woo Lee; Jun Gu Kim; Jae Sang Han; Haeun Kwon; Dongho Lee; Mi Kyeong Lee; Bang Yeon Hwang

doi:10.1016/j.phytol.2020.10.014

Tetrahydroprotoberberine N-oxides from Chelidonium majus and their inhibitory effects on NO production in RAW 264.7 cells

Thi Phuong Linh Le, Jin Woo Lee, Jun Gu Kim, Jae Sang Han, Haeun Kwon, 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

Two new tetrahydroprotoberberine N-oxides, 7R,14S-cis-tetrahydrocoptisine N-oxide (1) and 7R,14R-trans-tetrahydrocoptisine N-oxide (2) along with fourteen known compounds (3–16) were isolated from the aerial parts of Chelidonium majus. Their structures were elucidated by spectroscopic and spectrometric methods, such as 1D and 2D-NMR (HSQC, HMBC, NOESY) and HRESIMS. The absolute configurations of 1 and 2 were established by comparison of their experimental and calculated ECD data. All isolates were evaluated for their inhibitory effects on the nitric oxide production in LPS-induced RAW 264.7 macrophages, and compounds 2, 6–10, 13, and 15 showed significant inhibitory effects with the IC₅₀ values ranging from 1.1–31.9 μM.

Original language	English
Pages (from-to)	38-42
Number of pages	5
Journal	Phytochemistry Letters
Volume	41
DOIs	https://doi.org/10.1016/j.phytol.2020.10.014
Publication status	Published - 2021 Feb

Keywords

Chelidonium majus
Nitric oxide, tetrahydrocoptisine N-oxide
Papaveraceae

ASJC Scopus subject areas

Biotechnology
Biochemistry
Agronomy and Crop Science
Plant Science

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10.1016/j.phytol.2020.10.014

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@article{c88c175fdeba4269afb211560ff4cd75,

title = "Tetrahydroprotoberberine N-oxides from Chelidonium majus and their inhibitory effects on NO production in RAW 264.7 cells",

abstract = "Two new tetrahydroprotoberberine N-oxides, 7R,14S-cis-tetrahydrocoptisine N-oxide (1) and 7R,14R-trans-tetrahydrocoptisine N-oxide (2) along with fourteen known compounds (3–16) were isolated from the aerial parts of Chelidonium majus. Their structures were elucidated by spectroscopic and spectrometric methods, such as 1D and 2D-NMR (HSQC, HMBC, NOESY) and HRESIMS. The absolute configurations of 1 and 2 were established by comparison of their experimental and calculated ECD data. All isolates were evaluated for their inhibitory effects on the nitric oxide production in LPS-induced RAW 264.7 macrophages, and compounds 2, 6–10, 13, and 15 showed significant inhibitory effects with the IC50 values ranging from 1.1–31.9 μM.",

keywords = "Chelidonium majus, Nitric oxide, tetrahydrocoptisine N-oxide, Papaveraceae",

author = "Le, {Thi Phuong Linh} and Lee, {Jin Woo} and Kim, {Jun Gu} and Han, {Jae Sang} and Haeun Kwon and Dongho Lee 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 Korea government (MIST) (No. 2020R1A2C1008406), the Medical Research Center Program (MRC, 2017R1A5A2015541 ) through the National Research Foundation of Korea , and by the Korea Basic Science Institute under the R&D program (Project No. C030440) supervised by the Ministry of Science and ICT. Publisher Copyright: {\textcopyright} 2020 Phytochemical Society of Europe",

year = "2021",

month = feb,

doi = "10.1016/j.phytol.2020.10.014",

language = "English",

volume = "41",

pages = "38--42",

journal = "Phytochemistry Letters",

issn = "1874-3900",

publisher = "Elsevier BV",

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AU - Le, Thi Phuong Linh

AU - Lee, Jin Woo

AU - Kim, Jun Gu

AU - Han, Jae Sang

AU - Kwon, Haeun

AU - Lee, Dongho

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 Korea government (MIST) (No. 2020R1A2C1008406), the Medical Research Center Program (MRC, 2017R1A5A2015541 ) through the National Research Foundation of Korea , and by the Korea Basic Science Institute under the R&D program (Project No. C030440) supervised by the Ministry of Science and ICT. Publisher Copyright: © 2020 Phytochemical Society of Europe

PY - 2021/2

Y1 - 2021/2

N2 - Two new tetrahydroprotoberberine N-oxides, 7R,14S-cis-tetrahydrocoptisine N-oxide (1) and 7R,14R-trans-tetrahydrocoptisine N-oxide (2) along with fourteen known compounds (3–16) were isolated from the aerial parts of Chelidonium majus. Their structures were elucidated by spectroscopic and spectrometric methods, such as 1D and 2D-NMR (HSQC, HMBC, NOESY) and HRESIMS. The absolute configurations of 1 and 2 were established by comparison of their experimental and calculated ECD data. All isolates were evaluated for their inhibitory effects on the nitric oxide production in LPS-induced RAW 264.7 macrophages, and compounds 2, 6–10, 13, and 15 showed significant inhibitory effects with the IC50 values ranging from 1.1–31.9 μM.

AB - Two new tetrahydroprotoberberine N-oxides, 7R,14S-cis-tetrahydrocoptisine N-oxide (1) and 7R,14R-trans-tetrahydrocoptisine N-oxide (2) along with fourteen known compounds (3–16) were isolated from the aerial parts of Chelidonium majus. Their structures were elucidated by spectroscopic and spectrometric methods, such as 1D and 2D-NMR (HSQC, HMBC, NOESY) and HRESIMS. The absolute configurations of 1 and 2 were established by comparison of their experimental and calculated ECD data. All isolates were evaluated for their inhibitory effects on the nitric oxide production in LPS-induced RAW 264.7 macrophages, and compounds 2, 6–10, 13, and 15 showed significant inhibitory effects with the IC50 values ranging from 1.1–31.9 μM.

KW - Chelidonium majus

KW - Nitric oxide, tetrahydrocoptisine N-oxide

KW - Papaveraceae

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DO - 10.1016/j.phytol.2020.10.014

M3 - Article

AN - SCOPUS:85095435141

SN - 1874-3900

VL - 41

SP - 38

EP - 42

JO - Phytochemistry Letters

JF - Phytochemistry Letters

ER -

Tetrahydroprotoberberine N-oxides from Chelidonium majus and their inhibitory effects on NO production in RAW 264.7 cells

Abstract

Keywords

ASJC Scopus subject areas

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