Bioactive sesquiterpenoids from the flowers of Inula japonica

被引:29
作者
Wu, Xing-De [1 ]
Ding, Lin-Fen [2 ,3 ]
Tu, Wen-Chao [1 ,2 ,3 ]
Yang, Hui [1 ,2 ,3 ]
Su, Jia [1 ]
Peng, Li-Yan [1 ]
Li, Yan [1 ]
Zhao, Qin-Shi [1 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
[2] Kunming Med Univ, Sch Pharmaceut Sci, Kunming 650500, Peoples R China
[3] Kunming Med Univ, Yunnan Key Lab Pharmacol Nat Prod, Kunming 650500, Peoples R China
基金
中国国家自然科学基金;
关键词
Inula japonica; Asteraceae; Sesquiterpenoids; Inujaponins A-I; Cytotoxicity; Nitric oxide (NO); NITRIC-OXIDE PRODUCTION; LACTONES; BRITANNICA; CONSTITUENTS; THUNB;
D O I
10.1016/j.phytochem.2016.07.008
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Phytochemical investigation of the flowers of Inula japonica led to isolation of nine sesquiterpenoids, inujaponins A-I, as well as eighteen known ones. These sesquiterpenoids belong to six skeletal-types, including eudesmane, 1,10-seco-eudesmane, germacrane, guaiane, 4,5-seco-guaiane, and pseudoguaiane sesquiterpenoids. Their structures were established by extensive spectroscopic analysis. The absolute configurations of inujaponin A, eupatolide, and deacetylovatifolin were determined by Cu-K alpha Xray crystallographic analysis. Most of the isolated compounds exhibited potent cytotoxicity against HL 60, SMMC-7721, A-549, MCF-7, and SW-480 cancer cell lines, with IC50 values ranging from 1.57 to 22.58 mu M. Some selected compounds also possessed significant inhibitory activity against LPS-induced NO production in RAW264.7 macrophages with IC50 values ranging from 1.42 to 8.99 mu M. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:68 / 76
页数:9
相关论文
共 50 条
[21]   Sesquiterpenoids from Inula lineariifolia Inhibit Nitric Oxide Production [J].
Nie, Li-Yue ;
Qin, Jiang-Jiang ;
Huang, Ying ;
Tan, Lan ;
Liu, Yu-Bo ;
Pan, Yue-Xing ;
Jin, Hui-Zi ;
Zhang, Wei-Dong .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (06) :1117-1120
[22]   SECOEUDESMANOLIDES FROM INULA-JAPONICA [J].
JESKE, F ;
HUNECK, S ;
JAKUPOVIC, J .
PHYTOCHEMISTRY, 1993, 34 (06) :1647-1649
[23]   Sesquiterpenoids from Inula racemosa Hook. f. Inhibit Nitric Oxide Production [J].
Zhang, Shou-De ;
Qin, Jiang-Jiang ;
Jin, Hui-Zi ;
Yin, Yin-Hua ;
Li, Hong-Lin ;
Yang, Xian-Wen ;
Li, Xia ;
Shan, Lei ;
Zhang, Wei-Dong .
PLANTA MEDICA, 2012, 78 (02) :166-171
[24]   New sesquiterpenes from Inula japonica Thunb. with their inhibitory activities against LPS-induced NO production in RAW264.7 macrophages [J].
Qin, Jiang-Jiang ;
Jin, Hui-Zi ;
Zhu, Jia-Xian ;
Fu, Jian-Jun ;
Zeng, Qi ;
Cheng, Xiang-Rong ;
Zhu, Yan ;
Shan, Lei ;
Zhang, Shou-De ;
Pan, Yue-Xing ;
Zhang, Wei-Dong .
TETRAHEDRON, 2010, 66 (48) :9379-9388
[25]   Antitumour Activities of Sesquiterpene Lactones from Inula helenium and Inula japonica [J].
Li, Yong ;
Ni, Zhi-Yu ;
Zhu, Meng-Chu ;
Dong, Mei ;
Wang, Si-Ming ;
Shi, Qing-Wen ;
Zhang, Man-Li ;
Wang, Yu-Fang ;
Huo, Chang-hong ;
Kiyota, Hiromasa ;
Cong, Bin .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, 2012, 67 (7-8) :375-380
[26]   Camellia japonica Flowers as a Source of Nutritional and Bioactive Compounds [J].
Pereira, Antia G. ;
Cassani, Lucia ;
Liu, Chao ;
Li, Ningyang ;
Chamorro, Franklin ;
Barreira, Joao C. M. ;
Simal-Gandara, Jesus ;
Prieto, Miguel A. .
FOODS, 2023, 12 (15)
[27]   A monoterpene and two sesquiterpenoids from the flowers of Achillea millefolium [J].
Ni, Zhiyu ;
Wu, Yibing ;
Zhang, Kai ;
Dong, Mei ;
Sauriol, Francoise ;
Huo, Changhong ;
Gu, Yucheng ;
Shi, Qingwen .
CHEMISTRY OF NATURAL COMPOUNDS, 2013, 49 (03) :450-453
[28]   Sesquiterpenoids and flavonoids from Inula viscosa induce programmed cell death in kinetoplastids [J].
Zeouk, Ikrame ;
Sifaoui, Ines ;
Lopez-Arencibia, Atteneri ;
Reyes-Batlle, Maria ;
Bethencourt-Estrella, Carlos J. ;
Bazzocchi, Isabel L. ;
Bekhti, Khadija ;
Lorenzo-Morales, Jacob ;
Jimenez, Ignacio A. ;
Pinero, Jose E. .
BIOMEDICINE & PHARMACOTHERAPY, 2020, 130
[29]   Selective cytotoxicity, inhibition of cell cycle progression, and induction of apoptosis in human breast cancer cells by sesquiterpenoids from Inula lineariifolia Turcz [J].
Qin, Jiang-Jiang ;
Jin, Hui-Zi ;
Huang, Ying ;
Zhang, Shou-De ;
Shan, Lei ;
Voruganti, Sukesh ;
Nag, Subhasree ;
Wang, Wei ;
Zhang, Wei-Dong ;
Zhang, Ruiwen .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 68 :473-481
[30]   Sesquiterpenoids isolated from the flower of Inula japonica as potential antitumor leads for intervention of paclitaxel-resistant non-small-cell lung cancer [J].
Ding, Yahui ;
Wang, Tianpeng ;
Chen, Tianyang ;
Xie, Chunfeng ;
Zhang, Quan .
BIOORGANIC CHEMISTRY, 2020, 101