Limonoids with modified furan rings from root barks of Toona sinensis

被引:22
作者
Li, Jun-He [1 ]
Li, Yi [2 ]
An, Fa-Liang [1 ]
Zhou, Miao-Miao [1 ]
Luo, Jie [1 ]
Jian, Kai-Li [1 ]
Luo, Jun [1 ]
Kong, Ling Yi [1 ]
机构
[1] China Pharmaceut Univ, Dept Nat Med Chem, State Key Lab Nat Med, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China
[2] Nanjing Normal Univ, Testing & Anal Ctr, Nanjing 210046, Jiangsu, Peoples R China
关键词
Toona sinensis (A. Juss.) Roem; Limonoids; Modified furan rings; Cytotoxicity; anti-Inflammatory activity; TETRANORTRITERPENOID DERIVATIVES; BEARING LIMONOIDS; CHINESE MANGROVE; ANTIFEEDANTS;
D O I
10.1016/j.tet.2016.09.061
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Toonasinemines A-K (1-12), 12 new azadirone- and gedunin-type limonoids with eight-classes of modified furan rings, were isolated from the root barks of Toona sinensis (A. Juss.) Roem. Their structures were elucidated based on detailed spectroscopic analyses, and the absolute configurations of 1-9 were established by the electronic circular dichroism exciton chirality method. The lactam-bearing moieties in compounds 1-7 were rare in limonoids family. Results of bioactivities screening exhibited that 1, 4, and 8 showed moderate cytotoxicities against HepG2, MCF-7, and U2OS human cancer cell lines, and 1, 2, 6, 8, and 9 exhibited marked inhibitory effects on nitric oxide (NO) production in LPS-activated RAW 264.7 macrophages at nontoxic concentration. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7481 / 7487
页数:7
相关论文
共 21 条
[1]   Mechanism of Toona sinensis-stimulated adrenal steroidogenesis in primary rat adrenal cells [J].
Chen, Yung-Chia ;
Liang, Yi-Lin ;
Huang, Yuan-Li ;
Huang, Bu-Miin .
JOURNAL OF FUNCTIONAL FOODS, 2015, 14 :318-323
[2]   Tetranortriterpenoid derivatives from Turraea parvifolia (Meliaceae) [J].
Cheplogoi, PK ;
Mulholland, DA .
PHYTOCHEMISTRY, 2003, 62 (08) :1173-1178
[3]   Structure elucidation of an unprecedented alkaloid and a new limonoid from Xylocarpus granatum [J].
Cui, Jianxin ;
Ouyang, Jie ;
Deng, Zhiwei ;
Lin, Wenhan .
MAGNETIC RESONANCE IN CHEMISTRY, 2008, 46 (09) :894-897
[4]   New Limonoids and a Dihydrobenzofuran Norlignan from the Roots of Toona sinensis [J].
Dong, Xiao-Jie ;
Zhu, Yun-Fei ;
Bao, Guan-Hu ;
Hu, Feng-Lin ;
Qin, Guo-Wei .
MOLECULES, 2013, 18 (03) :2840-2850
[5]  
Edmonds Jennifer M., 1998, Curtis's Botanical Magazine, V15, P186, DOI 10.1111/1467-8748.00169
[6]   Salvinicins A and B, new neoclerodane diterpenes from Salvia divinorum [J].
Harding, WW ;
Tidgewell, K ;
Schmidt, M ;
Shah, K ;
Dersch, CM ;
Snyder, J ;
Parrish, D ;
Deschamps, JR ;
Rothman, RB ;
Prisinzano, TE .
ORGANIC LETTERS, 2005, 7 (14) :3017-3020
[7]   Toona sinensis and its major bioactive compound gallic acid inhibit LPS-induced inflammation in nuclear factor-κB transgenic mice as evaluated by in vivo bioluminescence imaging [J].
Hsiang, Chien-Yun ;
Hseu, You-Cheng ;
Chang, Yi-Chih ;
Kumar, K. J. Senthil ;
Ho, Tin-Yun ;
Yang, Hsin-Ling .
FOOD CHEMISTRY, 2013, 136 (02) :426-434
[8]   Limonoids isolated from Toona sinensis and their radical scavenging, anti-inflammatory and cytotoxic activities [J].
Hu, Jiang ;
Song, Yan ;
Mao, Xia ;
Wang, Zhen-Ji ;
Zhao, Qin-Jie .
JOURNAL OF FUNCTIONAL FOODS, 2016, 20 :1-9
[9]  
KRAUS W, 1987, LIEBIGS ANN CHEM, P337
[10]   A Targeted Multiple Antigenic Peptide Vaccine Augments the Immune Response to Self TGF-β1 and Suppresses Ongoing Hepatic Fibrosis [J].
Li, Yaping ;
Wang, Wenjun ;
Jia, Xiaoli ;
Zhai, Song ;
Wang, Xiufang ;
Wang, Yuan ;
Dang, Shuangsuo .
ARCHIVUM IMMUNOLOGIAE ET THERAPIAE EXPERIMENTALIS, 2015, 63 (04) :305-315