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Planta Med 2018; 84(18): 1348-1354
DOI: 10.1055/a-0647-1901
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

New Hirsutinolide-Type Sesquiterpenoids from Vernonia cinerea Inhibit Nitric Oxide Production in LPS-Stimulated RAW264.7 Cells

Li-Ming Yang Kuo   *
1   School of Pharmacy, Taipei Medical University, Taipei, Taiwan, Republic of China
,
Pei-Yi Tseng   *
2   Department of Life Sciences and Institute of Genome Sciences, National Yang Ming University, Taipei, Taiwan, Republic of China
3   National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan, Republic of China
,
Yu-Chi Lin
3   National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan, Republic of China
,
Chia-Ching Liaw
3   National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan, Republic of China
,
Li-Jie Zhang
3   National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan, Republic of China
,
Keng-Chang Tsai
3   National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan, Republic of China
5   The Ph. D. Program for Medical Biotechnology, College of Medical Science and Technology, Taipei Medical University, Taipei, Taiwan, Republic of China
,
Zhi-Hu Lin
3   National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan, Republic of China
,
Hsiu-O Ho
1   School of Pharmacy, Taipei Medical University, Taipei, Taiwan, Republic of China
,
Yao-Haur Kuo
3   National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan, Republic of China
4   Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University,Taichung, Taiwan, Republic of China
6   Ph. D. Program in Clinical Drug Development of Chinese Herbal Medicine, College of Pharmacy, Taipei Medical University, Taipei, Taiwan, Republic of China
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Publikationsverlauf

received 14. November 2017
revised 12. Juni 2018

accepted 18. Juni 2018

Publikationsdatum:
09. Juli 2018 (online)

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Abstract

Phytochemical investigation of ethanol extracts from two Taiwanese collections of Vernonia cinerea resulted in the isolation of eighteen hirsutinolide-type sesquiterpenoids, including seven new ones designated as vernolides E – K (1–7). All structures were determined by a combination of detailed spectroscopic analyses (NMR and MS) and comparison with reported data. In an in vitro anti-inflammatory assay, compounds 3, 7, 9, 11, and 14 exhibited strong inhibitory activities toward NO production by LPS-induced RAW264.7 macrophages, with IC50 values of 1.18, 0.85, 0.66, 0.71 and 0.45 µM, respectively, without affecting cellular viability at 40 µM. Preliminary structure-activity relationships indicate that the ester groups at C-8 and C-13 may enhance inhibition of NO production.

Key words

Vernonia cinerea - Asteraceae - hirsutinolide - vernolide - anti-inflammatory - RAW264.7 cells - nitric oxide

* These authors contributed equally to this work.


Supporting Information

    1H- and 13C-NMR spectra, as well as dose-response column graphs for compounds 1–7, are available as Supporting Information.

  • Supporting Information
 

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