LC-MS Guided Isolation of (±)-Sweriledugenin A, a Pair of Enantiomeric Lactones, from Swertia leducii

被引:24
作者
Geng, Chang-An [1 ]
Chen, Xing-Long [1 ]
Zhou, Ning-Jia [1 ]
Chen, Hao [1 ]
Ma, Yun-Bao [1 ]
Huang, Xiao-Yan [1 ]
Zhang, Xue-Mei [1 ]
Chen, Ji-Jun [1 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
基金
美国国家科学基金会; 中国国家自然科学基金; 中国科学院西部之光基金;
关键词
ALKALOIDS;
D O I
10.1021/ol403198d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-)-Sweriledugenin A, a pair of novel enantiomeric lactones, were isolated from Swertia leducii under the guidance of LC-MS investigation. The enantiomeric separation was achieved by HPLC on a chiral column. Their structures were determined by extensive NMR spectra, X-ray, and quantum calculations. (+)-Sweriledugenin A and (-)-sweriledugenin A showed activities inhibiting HBV DNA replication with the IC50 values of 36.86 and 26.55 mu M on the HepG 2.2.15 cell line in vitro.
引用
收藏
页码:370 / 373
页数:4
相关论文
共 13 条
[1]  
[Anonymous], 1988, FLORA CHINA, V62, P391
[2]  
Frisch M. J., 2010, GAUSSIAN 09 REVISION
[3]   Mulberrofuran G and Isomulberrofuran G from Morus alba L.: Anti-hepatitis B Virus Activity and Mass Spectrometric Fragmentation [J].
Geng, Chang-An ;
Ma, Yun-Bao ;
Zhang, Xue-Mei ;
Yao, Shu-Ying ;
Xue, Duo-Qing ;
Zhang, Rong-Ping ;
Chen, Ji-Jun .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (33) :8197-8202
[4]   Anti-Hepatitis B Virus Active Lactones from the Traditional Chinese Herb: Swertia mileensis [J].
Geng, Chang-An ;
Wang, Li-Jun ;
Zhang, Xue-Mei ;
Ma, Yun-Bao ;
Huang, Xiao-Yan ;
Luo, Jie ;
Guo, Rui-Hua ;
Zhou, Jun ;
Shen, Yong ;
Zuo, Ai-Xue ;
Jiang, Zhi-Yong ;
Chen, Ji-Jun .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (14) :3893-3903
[5]   Swerilactones A and B, Anti-HBV New Lactones from a Tradtional Chinese Herb: Swertia mileensis as a Treatment for Viral Hepatitis [J].
Geng, Chang-An ;
Jiang, Zhi-Yong ;
Ma, Yun-Bao ;
Luo, Jie ;
Zhang, Xue-Mei ;
Wang, Hong-Ling ;
Shen, Yong ;
Zuo, Ai-Xue ;
Zhou, Jun ;
Chen, Ji-Jun .
ORGANIC LETTERS, 2009, 11 (18) :4120-4123
[6]  
Guan Tian-Ye, 2011, Chinese Journal of Natural Medicines, V9, P385, DOI 10.3724/SP.J.1009.2011.00385
[7]   Structure and Biosynthesis of the Antibiotic Bottromycin D [J].
Hou, Yanpeng ;
Tianero, Ma. Diarey B. ;
Kwan, Jason C. ;
Wyche, Thomas P. ;
Michel, Cole R. ;
Ellis, Gregory A. ;
Vazquez-Rivera, Emmanuel ;
Braun, Doug R. ;
Rose, Warren E. ;
Schmidt, Eric W. ;
Bugni, Tim S. .
ORGANIC LETTERS, 2012, 14 (19) :5050-5053
[8]   Absolute Configurations of Fungal and Plant Metabolites by Chiroptical Methods. ORD, ECD, and VCD Studies on Phyllostin, Scytolide, and Oxysporone [J].
Mazzeo, Giuseppe ;
Santoro, Ernesto ;
Andolfi, Anna ;
Cimmino, Alessio ;
Troselj, Pavle ;
Petrovic, Ana G. ;
Superchi, Stefano ;
Evidente, Antonio ;
Berova, Nina .
JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04) :588-599
[9]   Spongolactams, farnesyl transferase inhibitors from a marine sponge: Isolation through an LC/MS-Guided assay, structures, and semisyntheses [J].
Mori, Daisuke ;
Kimura, Yuko ;
Kitamura, Shigeyuki ;
Sakagami, Youji ;
Yoshioka, Yukio ;
Shintani, Tomoaki ;
Okamoto, Tetsuji ;
Ojika, Makoto .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) :7190-7198
[10]   6-Deoxyerythronolide B Synthase Thioesterase-Catalyzed Macrocyclization Is Highly Stereoselective [J].
Pinto, Atahualpa ;
Wang, Meng ;
Horsman, Mark ;
Boddy, Christopher N. .
ORGANIC LETTERS, 2012, 14 (09) :2278-2281