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Molecules 2014, 19(4), 4608-4623; doi:10.3390/molecules19044608
Article

Anti-Inflammatory Triterpenoids from the Stems of Microtropis Fokienensis

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1 School of Chinese Medicine for Post Baccalaureate, College of Medicine, I Shou University, Kaohsiung 82445, Taiwan 2 Department of Botanicals, Medical and Pharmaceutical Industry Technology and Development Center, New Taipei City 248, Taiwan 3 Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan 4 Department of Biomedical Engineering, College of Medicine, I Shou University, Kaohsiung 82445, Taiwan 5 School of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan 6 National Museum of Natural Science, Taichung 404, Taiwan 7 Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan 8 Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan 9 Cancer Center, Kaohsiung Medical University Hospital, No. 100 Tz-You First Road, Kaohsiung 807, Taiwan 10 Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan 11 Center for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan
* Authors to whom correspondence should be addressed.
Received: 3 March 2014 / Revised: 9 April 2014 / Accepted: 9 April 2014 / Published: 14 April 2014
(This article belongs to the Section Metabolites)
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Abstract

Three new ursane- and four new oleanane- type triterpenoids 17 were isolated, along with six known compounds 813, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates 410 and known compounds 1417 that were previously isolated from this material were evaluated for anti-inflammatory activity based on effects against superoxide anion generation and elastase release by neutrophils in response to fMLP/CB. 11α,30-Dihydroxy-2,3-seco-olean-12-en-2,3-dioic anhydride (7) was the first triterpene anhydride from the genus of Microtropis to have the ring A expanded to a seven-membered ring; it showed significant anti-inflammatory activity against superoxide anion generation and elastase release. Unexpectedly, 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17) showed the best effect against superoxide anion generation and elastase release with IC50 values of 0.06 ± 0.01 and 1.03 ± 0.35 µg/mL, respectively. Compound 17 had a dioic acid function, and compound 7 had an anhydride function modification in ring A; both showed promising activity in the target assays.
Keywords: Microtropis fokienensis; triterpenoids; ursane; oleanane; anti-inflammatory Microtropis fokienensis; triterpenoids; ursane; oleanane; anti-inflammatory
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Chen, I.-H.; Du, Y.-C.; Hwang, T.-L.; Chen, I.-F.; Lan, Y.-H.; Yen, H.-F.; Chang, F.-R.; Wu, Y.-C. Anti-Inflammatory Triterpenoids from the Stems of Microtropis Fokienensis. Molecules 2014, 19, 4608-4623.

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