A Pair of Windmill-Shaped Enantiomers from Lindera aggregata with Activity toward Improvement of Insulin Sensitivity

被引：44
作者：
Wang, Fei [2 ,3 ]
Gao, Yuan [3 ]
Zhang, Ling [2 ]
Bai, Bing [2 ]
Hu, Ya Nan [1 ]
Dong, Ze Jun [2 ]
Zhai, Qi Wei [1 ]
Zhu, Hua Jie [2 ]
Liu, Ji Kai [2 ]
机构：
[1] BioBioPha Co Ltd, Kunming 650204, Peoples R China
[2] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Biol Sci, Inst Nutr Sci, Shanghai 200031, Peoples R China
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 14期
基金：
中国国家自然科学基金;
关键词：
SESQUITERPENE LACTONES; OPTICAL-ROTATION; WATER EXTRACT; STRYCHNIFOLIA; ROOT; BUTANOLIDES;
D O I：
10.1021/ol1011289
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(+)-Linderaspirone A and (-)-linderaspirone A, a pair of natural windmill-shaped enantiomers, were isolated from the traditional Chinese medicine plant tinders aggregate by HPLC using a chiral column, achieving over 98% ee. Their structures and absolute configurations were determined on the basis of extensive analysis of NMR spectra, crystal X-ray diffraction, and calculation of the optical rotations (OR). They have an unprecedented carbon skeleton and showed significant activity against glucosamine-induced insulin resistance.
引用
收藏
页码：3196 / 3199
页数：4
相关论文
共 24 条
  • [11] Assignment of the Absolute Configuration of Concentricolide - Absolute Configuration Determination of Its Bioactive Analogs Using DFT Methods
    Ren, Jie
    Jiang, Ju-Xing
    Li, Liang-Bo
    Liao, Tou-Geng
    Tian, Ren-Rong
    Chen, Xu-lin
    Jiang, Si-Ping
    Pittman, Charles U., Jr.
    Zhu, Hua-Jie
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (23) : 3987 - 3991
  • [12] SIRT1 improves insulin sensitivity under insulin-resistant conditions by repressing PTP1B
    Sun, Cheng
    Zhang, Fang
    Ge, Xinjian
    Yan, Tingting
    Chen, Xingmiao
    Shi, Xianglin
    Zhai, Qiwei
    [J]. CELL METABOLISM, 2007, 6 (04) : 307 - 319
  • [13] Determination of molecular structure in solution using vibrational circular dichroism spectroscopy:: the supramolecular tetramer of S-2,2′-dimethyl-biphenyl-6,6′-dicarboxylic acid
    Urbanová, M
    Setnicka, V
    Devlin, FJ
    Stephens, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (18) : 6700 - 6711
  • [14] Sesquiterpene lactones from Carpesium abrotanoides
    Wang, Fei
    Yang, Ku
    Ren, Fu-Cai
    Liu, Ji-Kai
    [J]. FITOTERAPIA, 2009, 80 (01) : 21 - 24
  • [15] Sulfonated guaianolides from Saussurea lappa
    Wang, Fei
    Xie, Zheng-Hong
    Gao, Yuan
    Xu, Yao
    Cheng, Xue-Lian
    Liu, Ji-Kai
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2008, 56 (06) : 864 - 865
  • [16] Bi-linderone, a Highly Modified Methyl-linderone Dimer from Lindera aggregata with Activity toward Improvement of Insulin Sensitivity in Vitro
    Wang, Fei
    Gao, Yuan
    Zhang, Ling
    Liu, Ji-Kai
    [J]. ORGANIC LETTERS, 2010, 12 (10) : 2354 - 2357
  • [17] ent-Pimarane Diterpenoids from Siegesbeckia orientalis and Structure Revision of a Related Compound
    Wang, Fei
    Cheng, Xue-Lian
    Li, Ya-Ju
    Shi, Song
    Liu, Ji-Kai
    [J]. JOURNAL OF NATURAL PRODUCTS, 2009, 72 (11): : 2005 - 2008
  • [18] New geranyloxycoumarins from Toddalia asiatica
    Wang, Fei
    Xu, Yao
    Liu, Ji-Kai
    [J]. JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2009, 11 (08) : 752 - 756
  • [19] Alstonic acids A and B, unusual 2,3-secofernane triterpenoids from Alstonia scholaris
    Wang, Fei
    Ren, Fu-Cai
    Liu, Ji-Kai
    [J]. PHYTOCHEMISTRY, 2009, 70 (05) : 650 - 654
  • [20] New Terpenoids from Isodon sculponeata
    Wang, Fei
    Li, Xiang-Mei
    Liu, Ji-Kai
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (05) : 525 - 527
123