Anti-proliferative cassane-type diterpenoids from the seeds of Caesalpinia minax

被引:7
|
作者
Xu, Yunshao [1 ]
Shi, Wei [1 ]
Feng, Lu [2 ,3 ]
Cao, Jun [1 ]
Feng, Zheling [1 ]
Zhang, Qingwen [1 ]
Lu, Jinjian [1 ]
Ye, Yang [2 ,3 ,4 ]
Lin, Ligen [1 ]
机构
[1] Univ Macau, Inst Chinese Med Sci, State Key Lab Qual Res Chinese Med, Macau, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Mat Med, Nat Prod Chem Dept, Shanghai, Peoples R China
[4] Shanghai Tech Univ, Sch Life Sci & Technol, Shanghai, Peoples R China
基金
中国国家自然科学基金;
关键词
Caesalpinia minax; Fabaceae; cassane diterpenoids; cytotoxic activity;
D O I
10.1080/14786419.2020.1853729
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The seeds of Caesalpinia minax Hance have shown anti-tumor potential, while the chemical principle is still unknown. In a search for anti-tumor compounds, six new cassane-type diterpenoids, 12-demethylcaesalpin G (1), caesalpinolide H (2), 12-demethylcaesalpin H (3), caesalpinolide J (4), 12-O-ethyl neocaesalpin B (5), and 3-deacetyldecapetpene B (6), were isolated from the seeds of C. minax Hance, along with fifteen known analogues. The structures of the new compounds were established by means of spectroscopic techniques (NMR, HRESIMS and IR). The absolute configurations of the new compounds were determined by their ECD spectra. All of the new compounds were tested for their anti-proliferative activity against human lung cancer A549 cells, breast cancer MCF-7 cells, and ovarian cancer HEY cells. The results indicated that only compound 6 displayed moderate cytotoxicity against three cancer cell lines. Thus, the opening of furan ring in cassane-type diterpenoids might enhance the cytotoxic activity.
引用
收藏
页码:932 / 941
页数:10
相关论文
共 50 条
  • [31] Cytotoxic cassane diterpenoids from the seeds of Caesalpinia sappan
    Wu, Zheng-Feng
    Bao, Han
    Zhou, Fa-Yang
    Liu, Jing-Xin
    Meng, Fan-Cheng
    Feng, Lu
    Lu, Jin-Jian
    Zhang, Qing-Wen
    Ye, Yang
    Lin, Li-Gen
    CHINESE CHEMICAL LETTERS, 2017, 28 (08) : 1711 - 1715
  • [32] Bioactive cassane diterpenoids from the seeds of Caesalpinia sappan
    Zhu, Nai-Liang
    Xu, Xu-Dong
    Hu, Mei-Geng
    Sun, Zhong-Hao
    Wu, Tong-Yu
    Yuan, Jing-Quan
    Wu, Hai-Feng
    Tian, Yu
    Li, Peng-Fei
    Yang, Jun-Shan
    Ma, Guo-Xu
    PHYTOCHEMISTRY LETTERS, 2017, 22 : 113 - 116
  • [33] Four new cassane-type diterpenoids from the seed kernels of Caesalpinia cucullata Roxb.
    Wang, Miao
    Zhu, Tianliang
    Yu, Siyu
    Liu, Ting
    Zhou, Bei
    Gao, Huiyuan
    NATURAL PRODUCT RESEARCH, 2022, 36 (19) : 5032 - 5038
  • [34] A pair of epimeric cassane-type diterpenoids and a new labdane-type derivative from Caesalpinia decapetala
    Qiao, Yuben
    Liu, Yanfei
    Duan, Xueyan
    Chen, Chunmei
    Liu, Junjun
    Zhu, Hucheng
    Xue, Yongbo
    Zhang, Yonghui
    TETRAHEDRON, 2018, 74 (28) : 3852 - 3857
  • [35] Diterpenoids of the Cassane Type from Caesalpinia decapetala
    Qiao, Yuben
    Xu, Qianqian
    Hu, Zhengxi
    Li, Xiao-Nian
    Xiang, Ming
    Liu, Junjun
    Huang, Jinfeng
    Zhu, Hucheng
    Wang, Jianping
    Luo, Zengwei
    Xue, Yongbo
    Zhang, Yonghui
    JOURNAL OF NATURAL PRODUCTS, 2016, 79 (12): : 3134 - 3142
  • [36] Cassane-type diterpenoids from Caesalpinia echinata (Leguminosae) and their NF-κB signaling inhibition activities
    Mitsui, Taichi
    Ishihara, Risa
    Hayashi, Ken-ichiro
    Matsuura, Nobuyasu
    Akashi, Haruo
    Nozaki, Hiroshi
    PHYTOCHEMISTRY, 2015, 116 : 349 - 358
  • [37] Three new cassane diterpenes from the seeds of Caesalpinia minax Hance
    Liu, Qin
    Bai, Bai
    Yang, De-po
    Peng, Shi-yi
    Zhu, Long-ping
    Luo, Mai-hui
    Zhao, Zhi-min
    NATURAL PRODUCT RESEARCH, 2018, 32 (08) : 885 - 891
  • [38] Caesalpinaxin, a cassane-type diterpenoid with a 21-carbon core skeleton from the seeds of Caesalpinia minax possessing pro-angiogenetic property
    Lou, Ruohan
    Xu, Fan
    Xu, Yunshao
    Chen, Jiali
    Feng, Zheling
    Gan, Lishe
    Lin, Ligen
    BIOORGANIC CHEMISTRY, 2021, 117
  • [39] Six new cassane diterpenoids from the seeds of Caesalpinia sappan
    Deng, Zhen-Tao
    Su, Jia
    Ding, Lin-Fen
    Tu, Wen-Chao
    Yang, Hui
    Peng, Li-Yan
    Zhao, Qin-Shi
    Song, Liu-Dong
    Wu, Xing-De
    PHYTOCHEMISTRY LETTERS, 2016, 16 : 207 - 212
  • [40] Four New Cassane Diterpenoids From the Seeds of Caesalpinia Mimosoides
    Ma, Yu-Xin
    Pu, Xiao-Chen
    Xi, Rong-Gang
    Zhang, Yun-Qi
    Ma, Jun-Yi
    Wu, Zhao-Hua
    Gao, Hui-Yuan
    Wang, Miao
    CHEMISTRY & BIODIVERSITY, 2025,