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Molecules 2016, 21(5), 669; doi:10.3390/molecules21050669

Anti-Inflammatory Oleanolic Triterpenes from Chinese Acorns

1
School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China
2
Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen 518055, China
*
Author to whom correspondence should be addressed.
Academic Editors: Vassilios Roussis and Efstathia Ioannou
Received: 2 March 2016 / Revised: 17 May 2016 / Accepted: 17 May 2016 / Published: 20 May 2016
(This article belongs to the Special Issue Triterpenes and Triterpenoids 2016)
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Abstract

Acorns play an important role in human history and are a source of food and recipes for many cultures around the world. In this study, eleven oleanolic triterpenes, one of which was novel, were isolated from Chinese acorns (Quercus serrata var. brevipetiolata). The chemical structure of the novel triterpene, which was identified as 2α,3β,19α-trihydroxy-24-oxo-olean-12-en-28-oic acid (1), was established based on the interpretation of chemical and spectroscopic analyses, including IR, HR-ESI-MS, and NMR experiments (1H, 13C NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY). All isolated compounds were tested for their inhibitory effects on LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages. Compared with the positive control drug indomethacin (IC50 = 47.4 μM), compounds 1, 3, 6 and 8 exhibited remarkable anti-inflammatory activities with IC50 values of 5.4, 7.8, 4.0 and 8.9 μM, respectively. Besides, compounds 2, 4, 7 and 9 also showed moderate anti-inflammatory activities with IC50 values of 10.1, 13.0, 20.1 and 17.2 μM, respectively. Furthermore, Compound 1 could inhibit TNF-α-induced IL-6 and IL-8 production in MH7A cells. View Full-Text
Keywords: Chinese acorns; oleanolic triterpenes; Quercus serrata var. brevipetiolata; anti-inflammatory activity; NO production; IL-6; IL-8 Chinese acorns; oleanolic triterpenes; Quercus serrata var. brevipetiolata; anti-inflammatory activity; NO production; IL-6; IL-8
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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. (CC BY 4.0).

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Huang, J.; Wang, Y.; Li, C.; Wang, X.; He, X. Anti-Inflammatory Oleanolic Triterpenes from Chinese Acorns. Molecules 2016, 21, 669.

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