RAPID AND EFFICIENT ISOLATION OF THE NICOTINIC RECEPTOR ANTAGONIST METHYLLYCACONITINE FROM DELPHINIUM - ASSIGNMENT OF THE METHYLSUCCINIMIDE ABSOLUTE STEREOCHEMISTRY AS S

被引:33
作者
COATES, PA
BLAGBROUGH, IS
HARDICK, DJ
ROWAN, MG
WONNACOTT, S
POTTER, BVL
机构
[1] UNIV BATH, SCH BIOL & BIOCHEM, BATH BA2 7AY, AVON, ENGLAND
[2] UNIV BATH, SCH PHARM & PHARMACOL, BATH BA2 7AY, AVON, ENGLAND
关键词
D O I
10.1016/S0040-4039(00)78476-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyllycaconitine (MLA) has been isolated from Garden Hybrid Delphinium and purified by vacuum liquid chromatography. C-13 NMR and optical rotation have been used to characterize the absolute configuration of the methylsuccinimide moiety as S. Ligand binding assays confirmed the potency of MLA and its selectivity for a-bungarotoxin-sensitive neuronal nicotinic acetylcholine receptors;
引用
收藏
页码:8701 / 8704
页数:4
相关论文
共 25 条
[1]  
BLAGBROUGH IS, 1994, TETRAHEDRON LETT, V35
[2]  
BRUNNER H, 1989, SYNTHESIS-STUTTGART, P743
[3]   THE CONFIGURATIONS OF THE 3-METHYLCYCLOPENTANONES AND RELATED COMPOUNDS [J].
EISENBRAUN, EJ ;
MCELVAIN, SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (12) :3383-3384
[4]  
FURUTA K, 1989, ORG SYNTH, V67, P76
[5]   The alkaloids of the seeds of Delphinium elatum, L [J].
Goodson, JA .
JOURNAL OF THE CHEMICAL SOCIETY, 1943, :139-141
[6]   METHYLLYCACONITINE, A NATURALLY-OCCURRING INSECTICIDE WITH A HIGH-AFFINITY FOR THE INSECT CHOLINERGIC RECEPTOR [J].
JENNINGS, KR ;
BROWN, DG ;
WRIGHT, DP .
EXPERIENTIA, 1986, 42 (06) :611-613
[7]  
KEELER RF, 1975, LLOYDIA, V38, P56
[8]   BRIDGEHEAD RADICALS IN ORGANIC-CHEMISTRY - AN EFFICIENT CONSTRUCTION OF THE ABDE RING-SYSTEM OF THE LYCOCTONINE ALKALOIDS [J].
KRAUS, GA ;
ANDERSH, B ;
SU, QG ;
SHI, JM .
TETRAHEDRON LETTERS, 1993, 34 (11) :1741-1744
[9]   METHYLLYCACONITINE AND (+)-ANATOXIN-A DIFFERENTIATE BETWEEN NICOTINIC RECEPTORS IN VERTEBRATE AND INVERTEBRATE NERVOUS SYSTEMS [J].
MACALLAN, DRE ;
LUNT, GG ;
WONNACOTT, S ;
SWANSON, KL ;
RAPOPORT, H ;
ALBUQUERQUE, EX .
FEBS LETTERS, 1988, 226 (02) :357-363
[10]   ISOLATION AND HPLC DETERMINATION OF METHYLLYCACONITINE IN A SPECIES OF LOW LARKSPUR (DELPHINIUM-NUTTALLIANUM) [J].
MAJAK, W ;
MCDIARMID, RE ;
BENN, MH .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1987, 35 (05) :800-802