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Planta Med 2015; 81(01): 62-70
DOI: 10.1055/s-0034-1383307
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

5β,19-Epoxycucurbitane Triterpenoids from Momordica charantia and Their Anti-Inflammatory and Cytotoxic Activity

Chia-Ching Liaw   *
1   R&D Department, Starsci Biotech Co. Ltd., Taipei, Taiwan
,
Hui-Chi Huang   *
2   Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung, Taiwan
,
Ping-Chun Hsiao
3   Division of Chinese Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, Taiwan
4   Endemic Species Research Institute, Council of Agriculture, Nantou, Taiwan
,
Li-Jie Zhang
3   Division of Chinese Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, Taiwan
,
Zhi-Hu Lin
3   Division of Chinese Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, Taiwan
,
Syh-Yuan Hwang
4   Endemic Species Research Institute, Council of Agriculture, Nantou, Taiwan
,
Feng-Lin Hsu
5   Graduate Institute of Pharmacognosy, Taipei Medical University, Taipei, Taiwan
,
Yao-Haur Kuo
3   Division of Chinese Materia Medica Development, National Research Institute of Chinese Medicine, Taipei, Taiwan
6   Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung, Taiwan
7   Ph.D Program for the Clinical Drug Discovery from Botanical Herbs, School of Pharmacy, Taipei Medical University, Taipei, Taiwan
› Author Affiliations
Further Information

Publication History

received 22 May 2014
revised 17 September 2014

accepted 19 October 2014

Publication Date:
03 December 2014 (online)

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Abstract

Five new 5β,19-epoxycucurbitane triterpenoids, taikugausins A–E (1–5), together with 5β,19-epoxy-25-methoxycucurbita-6,23-diene-3β,19-diol (6), have been isolated and characterized from the 70 % EtOH extract of the fresh fruits of Momordica charantia. The chemical structures of compounds 1–6 were elucidated on the basis of extensive spectroscopic analyses, especially 2D NMR (HMQC, HMBC, and NOESY) experiments and HRESIMS data. The relationship between NMR chemical shifts and the configuration of C-19 with an OMe group in 5β,19-epoxycucurbitane are described. Among them, compounds 3 and 4 exhibited remarkable anti-inflammatory activities by the inhibition of nitric oxide production at the concentration of 10 µg/mL. In addition, 3 and 4 also showed moderate cytotoxicity against WiDr, Hep G2, MCF-7, and HEp-2 human tumor cell lines.

Key words

Momordica charantia - Cucurbitaceae - 5β,19-epoxycucurbitane - taikuguasins - anti-inflammatory activity - cytotoxicity

* Equal contribution as first authors.


Supporting Information

 

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