Three new steroidal sapogenins derived from the roots of Cynanchum otophyllum and their cytotoxic activities

被引:6
作者
Li, Xiao-San [1 ,3 ]
Yang, Xue-Mei [1 ]
Liu, Li [1 ]
Zhang, Meng [2 ]
Ren, Yi-Chang [4 ]
Zhan, He-Hui [1 ]
Xing, Rui [1 ]
Luo, Rong-Rong [1 ]
Chen, Tang-Ji [1 ]
Tang, Jin-Shan [2 ]
机构
[1] Guangdong Med Univ, Sch Pharm, Dongguan 523808, Peoples R China
[2] Jinan Univ, Inst Tradit Chinese Med & Nat Prod, Coll Pharm, Guangzhou 510632, Peoples R China
[3] Guangdong Zhanjiang Marine Biomed Res Inst, Zhanjiang 524023, Peoples R China
[4] Southern Med Univ, Sch Pharmaceut Sci, Guangzhou 510515, Peoples R China
关键词
Cynanchum otophyllum; Steroidal sapogenins; Cardenolide; Cytotoxic activities; GLYCOSIDES; PLANTS;
D O I
10.1016/j.phytol.2021.08.002
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Three new steroidal sapogenins, 3fl,8fl,14fl-trihydroxycarda-5,20(22)-dienolide (1), (20R)-12fl,20-epoxy3fl,8fl,14fl-trihydroxy-17a-pregn-5-en-17-yl 4-hydroxy-3-methoxybenzoate (2), and 3,20-dioxo-8fl,14fl,17fltrihydroxy-17a-pregn-5-en-12fl-yl 4-hydroxybenzoate (3), along with four known C21-steroidal sapogenins (4-7) were isolated from the hydrolysate of Cynanchum otophyllum roots. Among them, compound 1 harbouring a rare fl-OH at the C-8 position in the cardenolide skeleton, was identified for the first time in the genus Cynanchum. Their structures were elucidated via extensive spectroscopic analysis, including UV, IR, HR-ESI-MS, 1D and 2D NMR. Compounds 1-7 were evaluated for their cytotoxic activities against four cancer cell lines (MCF-7, H1299, HeLa, and HepG2). Compound 1 exhibited significant inhibitory effects on the growth of the four cell lines, exhibiting IC50 values ranging from 6.86 to 22.09 mu M.
引用
收藏
页码:105 / 109
页数:5
相关论文
共 23 条
  • [11] Lee DU, 2002, B KOR CHEM SOC, V23, P9
  • [12] Bioactive C21 Steroidal Glycosides from the Roots of Cynanchum otophyllum That Suppress the Seizure-like Locomotor Activity of Zebrafish Caused by Pentylenetetrazole
    Li, Jin-Long
    Zhou, Juan
    Chen, Zhen-Hua
    Guo, Sheng-Ya
    Li, Chun-Qi
    Zhao, Wei-Min
    [J]. JOURNAL OF NATURAL PRODUCTS, 2015, 78 (07): : 1548 - 1555
  • [13] Li P.T., 1995, FLORA CHINA, P205
  • [14] New C21-steroidal aglycones from the roots of Cynanchum otophyllum and their anticancer activity
    Li, Xiao-San
    Yang, Xue-Mei
    Ding, Wen-Juan
    Xu, Zhi-Peng
    Zhang, Cai-Mei
    Long, Juan
    Liu, Li
    Lu, Cheng-Yu
    Tang, Jin-Shan
    [J]. FITOTERAPIA, 2021, 149
  • [15] New pregnane glycosides from the roots of Cynanchum otophyllum
    Ma, Xiao-Xia
    Jiang, Fang-Ting
    Yang, Qing-Xiong
    Liu, Xiu-Hua
    Zhang, Ying-Jun
    Yang, Chong-Ren
    [J]. STEROIDS, 2007, 72 (11-12) : 778 - 786
  • [16] Biotransformation of digitoxigenin by Cochliobolus lunatus
    Padua, Rodrigo M.
    Oliveira, Alaide B.
    Souza Filho, Jose D.
    Takahashi, Jaequeline A.
    de Abreu e Silva, Mauricio
    Braga, Fernao C.
    [J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2007, 18 (07) : 1303 - 1310
  • [17] STRUCTURE REVISION AND INTERNAL ACYL MIGRATION OF GYMNEMARSGENIN
    QIU, SX
    LIN, LZ
    NAN, Y
    LIN, P
    CHEN, JJ
    ZHANG, ZX
    ZHOU, J
    CORDELL, GA
    [J]. PHYTOCHEMISTRY, 1995, 40 (03) : 917 - 921
  • [18] STUDIES ON COMPONENTS OF ASCLEPIADACEAE PLANTS .22. STRUCTURES OF CYNANCHOGENIN AND SARCOSTIN
    SHIMIZU, Y
    MITSUHASHI, H
    [J]. TETRAHEDRON, 1968, 24 (11) : 4143 - +
  • [19] Cardiac Glycosides from the Seeds of Thevetia peruviana
    Tian, Dan-Mei
    Cheng, Huo-Yun
    Jiang, Miao-Miao
    Shen, Wei-Zai
    Tang, Jin-Shan
    Yao, Xin-Sheng
    [J]. JOURNAL OF NATURAL PRODUCTS, 2016, 79 (01): : 38 - 50
  • [20] Total Synthesis and Biological Evaluation of 19-Hydroxysarmentogenin-3-O-α-L-rhamnoside, Trewianin, and Their Aglycons
    Urabe, Daisuke
    Nakagawa, Yuki
    Mukai, Ken
    Fukushima, Kei-ichiro
    Aoki, Naoto
    Itoh, Hiroaki
    Nagatomo, Masanori
    Inoue, Masayuki
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (22) : 13888 - 13910