Three New Sesquiterpene Glycosides from the Rhizomes of Trillium tschonoskii

作者: Jie Yang , Yin-Jun Yang , Xin-Guang Sun , Jie Zhang , Yang Zhao

DOI: 10.3390/MOLECULES22081283

关键词: SulfonylGlycosideOrganic chemistryStereochemistryTrillium tschonoskiiAglyconeRhizomeTwo-dimensional nuclear magnetic resonance spectroscopySesquiterpeneChemistry

摘要: Three new sesquiterpene glycosides, possessing a rare aglycone with sulfonyl between C-1 and C-15 positions, named 3-(3′E-7′R,8′-dihydroxy-4′,8′-dimethyl-3′-nonenyl)-2,5-dihydro-1,1-dioxo-thiophen 7′-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranoside (1), 7′-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranoside (2), 7′-O-β-d-glucopyranosyl-6′-O-acetyl-(1→4)-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranoside (3), respectively, were isolated from the rhizomes of Trillium tschonoskii. Their structures established on basis spectroscopic data, including HR-ESI-MS, IR, 1D 2D NMR. The cytotoxic properties three compounds investigated using human hepatic L02 cells.

参考文章(14)
Bing-Jie Zhang, Xi-Feng Teng, Mei-Fen Bao, Xiu-Hong Zhong, Ling Ni, Xiang-Hai Cai, Cytotoxic indole alkaloids from Tabernaemontana officinalis. Phytochemistry. ,vol. 120, pp. 46- 52 ,(2015) , 10.1016/J.PHYTOCHEM.2014.12.025
Chun-Wang Meng, Cheng Peng, Qin-mei Zhou, Huai Yang, Li Guo, Liang Xiong, Spirostanols from the roots and rhizomes of Trillium tschonoskii Phytochemistry Letters. ,vol. 14, pp. 134- 137 ,(2015) , 10.1016/J.PHYTOL.2015.09.008
Yuhua Li, Changxu Liu, Dan Xiao, Jing Han, Zhenggang Yue, Yang Sun, Lei Fan, Feng Zhang, Jin Meng, Rong Zhang, Zhipeng Wang, Qibing Mei, Aidong Wen, Trillium tschonoskii steroidal saponins suppress the growth of colorectal Cancer cells in vitro and in vivo. Journal of Ethnopharmacology. ,vol. 168, pp. 136- 145 ,(2015) , 10.1016/J.JEP.2015.03.063
Junzhi Wang, Kun Zou, Yanming Zhang, Chuang Liu, Jun Wu, Yuan Zhou, Feijun Dan, Yaxiong Zhang, An 18-norspirostanol saponin with inhibitory action against COX-2 production from the underground part of Trillium tschonoskii. Chemical & Pharmaceutical Bulletin. ,vol. 55, pp. 679- 681 ,(2007) , 10.1248/CPB.55.679
Akihito Yokosuka, Yoshihiro Mimaki, Steroidal glycosides from the underground parts of Trillium erectum and their cytotoxic activity. Phytochemistry. ,vol. 69, pp. 2724- 2730 ,(2008) , 10.1016/J.PHYTOCHEM.2008.08.004
Masateru Ono, Chika Takamura, Fumie Sugita, Chikako Masuoka, Hitoshi Yoshimitsu, Tsuyoshi Ikeda, Toshihiro Nohara, Two new steroid glycosides and a new sesquiterpenoid glycoside from the underground parts of Trillium kamtschaticum Chemical & Pharmaceutical Bulletin. ,vol. 55, pp. 551- 556 ,(2007) , 10.1248/CPB.55.551
Hui Wang, Zhenbo Zhai, Nanlin Li, Haifeng Jin, Jianghao Chen, Shifang Yuan, Ling Wang, Juliang Zhang, Yongping Li, Jun Yun, Jing Fan, Jun Yi, Rui Ling, Steroidal saponin of Trillium tschonoskii. Reverses multidrug resistance of hepatocellular carcinoma Phytomedicine. ,vol. 20, pp. 985- 991 ,(2013) , 10.1016/J.PHYMED.2013.04.014
Jiang Chai, Xiaomei Song, Xin Wang, Qibing Mei, Zhao Li, Jiucheng Cui, Zhishu Tang, Zhenggang Yue, Two new compounds from the roots and rhizomes of Trillium tschonoskii Phytochemistry Letters. ,vol. 10, pp. 113- 117 ,(2014) , 10.1016/J.PHYTOL.2014.08.010
Patricia Y. Hayes, Reg Lehmann, Kerry Penman, William Kitching, James J. De Voss, Steroidal saponins from the roots of Trillium erectum (Beth root). Phytochemistry. ,vol. 70, pp. 105- 113 ,(2009) , 10.1016/J.PHYTOCHEM.2008.10.019
Jin-Chao Wei, Shu-Li Man, Wen-Yuan Gao, Xin Chai, Wan-Shun Zhao, Ying Wang, Song-Song Jing, Steroidal saponins from the rhizomes of Trillium tschonoskii Maxim. Biochemical Systematics and Ecology. ,vol. 44, pp. 112- 116 ,(2012) , 10.1016/J.BSE.2012.04.016