Synthesis and Biological Evaluation of Heteroanalogues of Kotalanol and De-O-Sulfonated Kotalanol

被引:26
作者
Mohan, Sankar [1 ]
Jayakanthan, Kumarasamy [1 ]
Nasi, Ravindranath [1 ]
Kuntz, Douglas A. [2 ,3 ]
Rose, David R. [2 ,3 ,4 ]
Pinto, B. Mario [1 ]
机构
[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada
[2] Univ Toronto, Dept Med Biophys, Toronto, ON M5G 2M9, Canada
[3] Ontario Canc Inst, Div Mol & Struct Biol, Burnaby, BC V5A 1S6, Canada
[4] Univ Waterloo, Dept Biol, Waterloo, ON N2L 3G1, Canada
关键词
MEDICINE SALACIA-RETICULATA; SULFONIUM SULFATE STRUCTURE; HUMAN MALTASE GLUCOAMYLASE; GLYCOSIDASE INHIBITOR SALACINOL; OCCURRING GLUCOSIDASE INHIBITOR; CHAIN-EXTENDED HOMOLOGS; TRADITIONAL MEDICINE; ANALOGS; BLINTOL;
D O I
10.1021/ol100080m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of nitrogen and selenium analogues of kotalanol and de-O-sulfonated kotalanol, naturally occurring sulfonium-ion glucosidase inhibitors isolated from Salacia reticulata, and their evaluation as glucosidase inhibitors against the N-terminal catalytic domain of human maltase glucoamylase (ntMGAM) are described.
引用
收藏
页码:1088 / 1091
页数:4
相关论文
共 24 条
[1]  
Chandrasena J.P. C., 1935, The Chemistry and Pharmacology of Ceylon and Indian Medicinal Plants
[2]   Synthesis of nitrogen analogues of salacinol and their evaluation as glycosidase inhibitors [J].
Ghavami, A ;
Johnston, BD ;
Jensen, MT ;
Svensson, B ;
Pinto, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (26) :6268-6271
[3]   Structure Proof and Synthesis of Kotalanol and De-O-sulfonated Kotalanol, Glycosidase Inhibitors Isolated from an Herbal Remedy for the Treatment of Type-2 Diabetes [J].
Jayakanthan, Kumarasamy ;
Mohan, Sankar ;
Pinto, B. Mario .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (15) :5621-5626
[4]   Double blind randomised placebo controlled cross over study of a herbal preparation containing Salacia reticulata in the treatment of type 2 diabetes [J].
Jayawardena, MHS ;
de Alwis, NMW ;
Hettigoda, V ;
Fernando, DJS .
JOURNAL OF ETHNOPHARMACOLOGY, 2005, 97 (02) :215-218
[5]  
Jayaweera D.M. A., 1981, Medicinal Plants Used in Ceylon-Part 1, P77
[6]   Synthesis of sulfonium sulfate analogues of disaccharides and their conversion to chain-extended homologues of salacinol: New glycosidase inhibitors [J].
Johnston, BD ;
Jensen, HH ;
Pinto, BM .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) :1111-1118
[7]   Synthesis of selenium analogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors [J].
Johnston, BD ;
Ghavami, A ;
Jensen, MT ;
Svensson, B ;
Pinto, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8245-8250
[8]   A new class of glucosidase inhibitor: Analogues of the naturally occurring glucosidase inhibitor salacinol with different ring heteroatom substituents and acyclic chain extension [J].
Liu, H ;
Sim, L ;
Rose, DR ;
Pinto, BM .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08) :3007-3013
[9]   Efficient synthesis of the glucosidase inhibitor blintol, the selenium analogue of the naturally occurring glycosidase inhibitor salacinol [J].
Liu, H ;
Pinto, BM .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :753-755
[10]  
MOHAN S, 2010, NAT PROD RE IN PRESS