ent-Strobane and ent-Pimarane Diterpenoids from Siegesbeckia pubescens

被引:42
|
作者
Wang, Jianbin [1 ]
Duan, Hongquan [2 ]
Wang, Yi [1 ]
Pan, Bowen [1 ]
Gao, Chun [1 ]
Gai, Chunyan [1 ]
Wu, Qiong [1 ]
Fu, Hongzheng [1 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[2] Tianjin Med Univ, Sch Pharm, Tianjin Key Lab Technol Enabling Dev Clin Therape, Tianjin 300070, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2017年 / 80卷 / 01期
基金
中国国家自然科学基金;
关键词
STEM BARK; KIRENOL; CELLS; ORIENTALIS;
D O I
10.1021/acs.jnatprod.6b00150
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two strobane diterpenoids, strobols A (1) and B (2), 15 new pimarane diterpenoids (3-6 and 8-18), and the known compounds kirenol (19), darutigenol (20), and ent-2 beta,15,16,19-tetrahydroxypimar-8(14)-ene (7) were isolated from the aerial parts of Siegesbeckia pubescens Makino. The structures of the new compounds were established based on the interpretation of HRESIMS and NMR analysis. The configurations of 1, 6, and 17 were confirmed by X-ray-crystallographic data. Compounds 3, 5, and 11 inhibited the migration of MB-MDA-231 breast cancer cells induced by the chemokine epithelial growth factor, with IC50 values of 4.26, 3.45, and 9.70 mu M, respectively.
引用
收藏
页码:19 / 29
页数:11
相关论文
共 50 条
  • [21] ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity
    Nogueira, Mauro S.
    Da Costa, Fernando B.
    Brun, Reto
    Kaiser, Marcel
    Schmidt, Thomas J.
    MOLECULES, 2016, 21 (09):
  • [22] NMR studies of darutoside, a rare ENT-pimarane glucoside
    Son, PT
    Giang, PM
    Taylor, WC
    NATURAL PRODUCT RESEARCH, 2005, 19 (05) : 503 - 507
  • [23] Harnessing the catalytic plasticity of the ent-kaurene synthase from Bradyrhizobium japonicum to produce the ent-rosane and ent-pimarane scaffolds
    Zhang, Fan
    Wang, Su-Jing
    Xiao, Wen
    Yu, Ming-Zhu
    Sha, Feng
    Wu, Ruibo
    Xiang, Zheng
    CATALYSIS SCIENCE & TECHNOLOGY, 2024, 14 (02) : 306 - 314
  • [24] Anticariogenic Properties of ent-Pimarane Diterpenes Obtained by Microbial Transformation
    Severiano, Marcela E.
    Simao, Marilia R.
    Porto, Thiago S.
    Martins, Carlos H. G.
    Veneziani, Rodrigo C. S.
    Furtado, Niege A. J. C.
    Arakawa, Nilton S.
    Said, Suraia
    de Oliveira, Dioneia C. R.
    Cunha, Wilson R.
    Gregorio, Luiz E.
    Ambrosio, Sergio R.
    MOLECULES, 2010, 15 (12) : 8553 - 8566
  • [25] CHEMISTRY OF FIJIAN PLANTS .6. ENT-PIMARANE AND ENT-ABIETANE DITERPENES FROM EUPHORBIA-FIDJIANA
    LAL, AR
    CAMBIE, RC
    RUTLEDGE, PS
    WOODGATE, PD
    PHYTOCHEMISTRY, 1990, 29 (07) : 2239 - 2246
  • [26] DITERPENOIDS FROM SIEGESBECKIA-PUBESCENS
    JIANG, X
    MA, YB
    XU, YL
    PHYTOCHEMISTRY, 1992, 31 (03) : 917 - 921
  • [27] ent-Pimarane Diterpenoid Dimers from Sigesbeckia glabrescens with Potent Anti-inflammatory Activities
    Gao, Xiao-Xu
    Zheng, Ying-Ying
    Zhang, Xiao-Yu
    Hu, Gao-Sheng
    Jia, Jing-Ming
    Wang, An-Hua
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (12) : 3315 - 3321
  • [28] Antimicrobial ent-pimarane diterpenes from Viguiera arenaria against Gram-positive bacteria
    Porto, Thiago Souza
    Furtado, Niege A. J. C.
    Heleno, Vladimir C. G.
    Martins, Carlos H. G.
    Da Costa, Fernando B.
    Severiano, Marcela E.
    Silva, Aline N.
    Veneziani, Rodrigo C. S.
    Ambrosio, Sergio R.
    FITOTERAPIA, 2009, 80 (07) : 432 - 436
  • [29] Oligandrin, a New Ent-Pimarane Type Diterpenoid and Other Bioactive Constituents from the Leaves of Croton oligandrus†
    Yannick S. F. Fongang
    Angelbert F. Awantu
    Jean J. K. Bankeu
    Mehreen Lateef
    Bruno N. Lenta
    Muhammad S. Ali
    Silvere A. Ngouela
    Chemistry of Natural Compounds, 2021, 57 : 94 - 100
  • [30] Oligandrin, a New Ent-Pimarane Type Diterpenoid and Other Bioactive Constituents from the Leaves of Croton oligandrus†
    Fongang, Yannick S. F.
    Awantu, Angelbert F.
    Bankeu, Jean J. K.
    Lateef, Mehreen
    Lenta, Bruno N.
    Ali, Muhammad S.
    Ngouela, Silvere A.
    CHEMISTRY OF NATURAL COMPOUNDS, 2021, 57 (01) : 94 - 100