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Open AccessArticle

Chemical Constituents of the Leaves of Butterbur (Petasites japonicus) and Their Anti-Inflammatory Effects

1
Department of Life and Nanopharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, Korea
2
College of Pharmacy, Kyung Hee University, Seoul 02447, Korea
3
Department of Fundamental Pharmaceutical Sciences, Graduate School, Kyung Hee University, Seoul 02447, Korea
4
Herbal Medicine Resources Research Center, Korea Institute of Oriental Medicine, Jeollanam-do 58245, Korea
5
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Tianjin Key Laboratory of Molecular Drug Research, and Drug Discovery Center for Infectious Disease, Nankai University, Tianjin 300350, China
6
Department of Biosystems and Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul 02841, Korea
*
Authors to whom correspondence should be addressed.
Biomolecules 2019, 9(12), 806; https://doi.org/10.3390/biom9120806
Received: 30 October 2019 / Revised: 26 November 2019 / Accepted: 27 November 2019 / Published: 29 November 2019
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: Petasites japonicus; Asteraceae; lignan; anti-inflammation; NO; PGE2; iNOS; COX-2; molecular docking Petasites japonicus; Asteraceae; lignan; anti-inflammation; NO; PGE2; iNOS; COX-2; molecular docking
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Lee, J.S.; Jeong, M.; Park, S.; Ryu, S.M.; Lee, J.; Song, Z.; Guo, Y.; Choi, J.-H.; Lee, D.; Jang, D.S. Chemical Constituents of the Leaves of Butterbur (Petasites japonicus) and Their Anti-Inflammatory Effects. Biomolecules 2019, 9, 806.

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