Vibsatins A and B, Two New Tetranorvibsane-Type Diterpenoids from Viburnum tinus cv. variegatus

被引:20
作者
Gao, Xiu [1 ,2 ]
Shao, Li-Dong [1 ,2 ]
Dong, Liao-Bin [1 ,2 ]
Cheng, Xiao [1 ]
Wu, Xing-De [1 ]
Liu, Fei [1 ,2 ]
Jiang, Wei-Wei [1 ,2 ]
Peng, Li-Yan [1 ]
He, Juan [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] Univ Chinese Acad Sci, Beijing 100039, Peoples R China
关键词
VIBSANE-TYPE DITERPENOIDS; BIOLOGICAL-ACTIVITIES; AWABUKI; ODORATISSIMUM; CYCLOADDITIONS; TRITERPENOIDS; CYLINDRICUM; CELLS;
D O I
10.1021/ol403707a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Vibsatins A (1) and B (2), a pair of 14,15,16,17-tetranorvibsane-type diterpenoids that feature a bicyclo[4.2.1]nonane moiety formed by a new C-13/C-2 bond, were isolated from the twigs and leaves of Viburnum tin us cv. variegatus. The structures and absolute configurations were elucidated by a combination of NMR spectra, optical rotation, and X-ray diffraction experiments. A possible biogenetic pathway is also proposed. Moreover, vibsatin A (1) enhanced the neurite outgrowth of NGF-mediated PC12 cells at a concentration of 10 mu M.
引用
收藏
页码:980 / 983
页数:4
相关论文
共 29 条
[1]  
Annette P.-J.C., 2010, TETRAHEDRON, V66, P6842
[2]   SPECIFICATION OF MOLECULAR CHIRALITY [J].
CAHN, RS ;
INGOLD, C ;
PRELOG, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (04) :385-&
[3]   Total Synthesis of (±)-4,5-Bis-epi-Neovibsanin A and B: A Neurite Outgrowth Comparison Study [J].
Chen, Annette P-J. ;
Mueller, C. Catharina ;
Cooper, Helen M. ;
Williams, Craig M. .
ORGANIC LETTERS, 2009, 11 (16) :3758-3761
[4]   Triterpenoids and Diterpenoids from Viburnum chingii [J].
Chen, Xuan-Qin ;
Li, Yan ;
He, Juan ;
Cheng, Xiao ;
Wang, Kou ;
Li, Ming-Ming ;
Pan, Zheng-Hong ;
Peng, Li-Yan ;
Zhao, Qin-Shi .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (04) :496-498
[5]   New diterpenoids from Viburnum awabuki [J].
El-Gamal, AAH ;
Wang, SK ;
Duh, CY .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (03) :333-336
[6]  
Eliel E. L., 2001, BASIC ORGANIC STEREO
[7]   First Enantiocontrolled Formal Synthesis of (+)-Neovibsanin B, A Neurotrophic Diterpenoid [J].
Esumi, Tomoyuki ;
Mori, Takehiro ;
Zhao, Ming ;
Toyota, Masao ;
Fukuyama, Yoshiyasu .
ORGANIC LETTERS, 2010, 12 (04) :888-891
[8]   Cyclovibsanins, unprecedented seven-membered vibsane-type diterpenes from Viburnum awabuki [J].
Fukuyama, Y ;
Morisaki, M ;
Minoshima, Y ;
Minami, H ;
Takahashi, H ;
Asakawa, Y .
LETTERS IN ORGANIC CHEMISTRY, 2004, 1 (02) :189-193
[9]  
Fukuyama Y., 2011, Current Topics in Phytochemistry, Volume 10, P39
[10]   Absolute structure of vibsanins B and C, and their chemical correlation [J].
Fukuyama, Y ;
Minami, H ;
Taoka, S ;
Kodama, M ;
Kawazu, K ;
Nemoto, H .
TETRAHEDRON LETTERS, 1997, 38 (08) :1435-1438