Chemical constituents of the leaves of butterbur (Petasites japonicus) and their anti-inflammatory effects

Jin Su Lee; Miran Jeong; Sangsu Park; Seung Mok Ryu; Jun Lee; Ziteng Song; Yuanqiang Guo; Jung Hye Choi; Dongho Lee; Dae Sik Jang

doi:10.3390/biom9120806

Chemical constituents of the leaves of butterbur (Petasites japonicus) and their anti-inflammatory effects

Jin Su Lee, Miran Jeong, Sangsu Park, Seung Mok Ryu, Jun Lee, Ziteng Song, Yuanqiang Guo, Jung Hye Choi, Dongho Lee, Dae Sik Jang

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

28 Citations (Scopus)

Abstract

Two new aryltetralin lactone lignans, petasitesins A and B were isolated from the hot water extract of the leaves of butterbur (Petasites japonicus) along with six known compounds. The chemical structures of lignans 1 and 2 were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Petasitesin A and cimicifugic acid D showed significant inhibitory effects on the production of both prostaglandin E2 (PGE2) and NO in RAW264.7 macrophages. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were inhibited by compound 1 in RAW264.7 cells. Furthermore, compounds 1 and 3 exhibited strong affinities with both iNOS and COX-2 enzymes in molecular docking studies.

Original language	English
Article number	806
Journal	Biomolecules
Volume	9
Issue number	12
DOIs	https://doi.org/10.3390/biom9120806
Publication status	Published - 2019

Bibliographical note

Funding Information:
Funding: This research was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Agri-Bio Industry Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA), Republic of Korea (116044-1, 118046-03). This work was also supported by the National Research Foundation of Korea (NRF) grant funded by Ministry of Science and ICT (MSIT), Republic of Korea (NRF-2019R1A2C1083945).

Funding Information:
This research was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Agri-Bio Industry Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA), Republic of Korea (116044-1, 118046-03). This work was also supported by the National Research Foundation of Korea (NRF) grant funded by Ministry of Science and ICT (MSIT), Republic of Korea (NRF-2019R1A2C1083945).

Publisher Copyright:
© 2019 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

Anti-inflammation
Asteraceae
COX-2
INOS
Lignan
Molecular docking
NO
PGE2
Petasites japonicus

ASJC Scopus subject areas

Biochemistry
Molecular Biology

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10.3390/biom9120806

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@article{55e29c176f374473a563710ccf1a9d7e,

title = "Chemical constituents of the leaves of butterbur (Petasites japonicus) and their anti-inflammatory effects",

abstract = "Two new aryltetralin lactone lignans, petasitesins A and B were isolated from the hot water extract of the leaves of butterbur (Petasites japonicus) along with six known compounds. The chemical structures of lignans 1 and 2 were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Petasitesin A and cimicifugic acid D showed significant inhibitory effects on the production of both prostaglandin E2 (PGE2) and NO in RAW264.7 macrophages. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were inhibited by compound 1 in RAW264.7 cells. Furthermore, compounds 1 and 3 exhibited strong affinities with both iNOS and COX-2 enzymes in molecular docking studies.",

keywords = "Anti-inflammation, Asteraceae, COX-2, INOS, Lignan, Molecular docking, NO, PGE2, Petasites japonicus",

author = "Lee, {Jin Su} and Miran Jeong and Sangsu Park and Ryu, {Seung Mok} and Jun Lee and Ziteng Song and Yuanqiang Guo and Choi, {Jung Hye} and Dongho Lee and Jang, {Dae Sik}",

note = "Funding Information: Funding: This research was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Agri-Bio Industry Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA), Republic of Korea (116044-1, 118046-03). This work was also supported by the National Research Foundation of Korea (NRF) grant funded by Ministry of Science and ICT (MSIT), Republic of Korea (NRF-2019R1A2C1083945). Funding Information: This research was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Agri-Bio Industry Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA), Republic of Korea (116044-1, 118046-03). This work was also supported by the National Research Foundation of Korea (NRF) grant funded by Ministry of Science and ICT (MSIT), Republic of Korea (NRF-2019R1A2C1083945). Publisher Copyright: {\textcopyright} 2019 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2019",

doi = "10.3390/biom9120806",

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volume = "9",

journal = "Biomolecules",

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AU - Lee, Jin Su

AU - Jeong, Miran

AU - Park, Sangsu

AU - Ryu, Seung Mok

AU - Lee, Jun

AU - Song, Ziteng

AU - Guo, Yuanqiang

AU - Choi, Jung Hye

AU - Lee, Dongho

AU - Jang, Dae Sik

N1 - Funding Information: Funding: This research was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Agri-Bio Industry Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA), Republic of Korea (116044-1, 118046-03). This work was also supported by the National Research Foundation of Korea (NRF) grant funded by Ministry of Science and ICT (MSIT), Republic of Korea (NRF-2019R1A2C1083945). Funding Information: This research was supported by Korea Institute of Planning and Evaluation for Technology in Food, Agriculture and Forestry (IPET) through Agri-Bio Industry Technology Development Program, funded by Ministry of Agriculture, Food and Rural Affairs (MAFRA), Republic of Korea (116044-1, 118046-03). This work was also supported by the National Research Foundation of Korea (NRF) grant funded by Ministry of Science and ICT (MSIT), Republic of Korea (NRF-2019R1A2C1083945). Publisher Copyright: © 2019 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2019

Y1 - 2019

N2 - Two new aryltetralin lactone lignans, petasitesins A and B were isolated from the hot water extract of the leaves of butterbur (Petasites japonicus) along with six known compounds. The chemical structures of lignans 1 and 2 were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Petasitesin A and cimicifugic acid D showed significant inhibitory effects on the production of both prostaglandin E2 (PGE2) and NO in RAW264.7 macrophages. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were inhibited by compound 1 in RAW264.7 cells. Furthermore, compounds 1 and 3 exhibited strong affinities with both iNOS and COX-2 enzymes in molecular docking studies.

AB - Two new aryltetralin lactone lignans, petasitesins A and B were isolated from the hot water extract of the leaves of butterbur (Petasites japonicus) along with six known compounds. The chemical structures of lignans 1 and 2 were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Petasitesin A and cimicifugic acid D showed significant inhibitory effects on the production of both prostaglandin E2 (PGE2) and NO in RAW264.7 macrophages. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were inhibited by compound 1 in RAW264.7 cells. Furthermore, compounds 1 and 3 exhibited strong affinities with both iNOS and COX-2 enzymes in molecular docking studies.

KW - Anti-inflammation

KW - Asteraceae

KW - COX-2

KW - INOS

KW - Lignan

KW - Molecular docking

KW - NO

KW - PGE2

KW - Petasites japonicus

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U2 - 10.3390/biom9120806

DO - 10.3390/biom9120806

M3 - Article

C2 - 31795455

AN - SCOPUS:85075960916

SN - 2218-273X

VL - 9

JO - Biomolecules

JF - Biomolecules

IS - 12

M1 - 806

ER -

Chemical constituents of the leaves of butterbur (Petasites japonicus) and their anti-inflammatory effects

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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