title: Anti-Inflammatory Oleanolic Triterpenes from Chinese Acorns.
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, (13)C 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.
authors.affiliation: School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China. hj_yellow@163.com.
authors.forename: Jie
authors.initials: J
authors.lastname: Huang
authors.affiliation: School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China. wangyihai@whu.edu.cn.
authors.forename: Yihai
authors.initials: Y
authors.lastname: Wang
authors.affiliation: School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China. inuyashachuanli@163.com.
authors.forename: Chuan
authors.initials: C
authors.lastname: Li
authors.affiliation: Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen 518055, China. xl.wang@siat.ac.cn.
authors.forename: Xinluan
authors.initials: X
authors.lastname: Wang
authors.affiliation: School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, China. hexiangjiu@163.com.
authors.forename: Xiangjiu
authors.initials: X
authors.lastname: He
mesh_terms: D000818:Animals; D006801:Humans; D007249:Inflammation / Q000139:chemically induced / Q000188:drug therapy*; D015850:Interleukin-6 / Q000096:biosynthesis; D016209:Interleukin-8 / Q000096:biosynthesis; D008070:Lipopolysaccharides / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D009828:Oleanolic Acid / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D029963:Quercus / Q000737:chemistry*; D000067996:RAW 264.7 Cells; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis
chemical_list: D015850:Interleukin-6; D016209:Interleukin-8; D008070:Lipopolysaccharides; D014315:Triterpenes; D014409:Tumor Necrosis Factor-alpha; D009828:Oleanolic Acid
keywords: Chinese acorns; IL-6; IL-8; NO production; Quercus serrata var. brevipetiolata; anti-inflammatory activity; oleanolic triterpenes