Structure elucidation of indole-indoline type alkaloids: A retrospective account from the point of view of current NMR and MS technology

被引:19
作者
Beni, Zoltan [1 ]
Hada, Viktor [2 ]
Dubrovay, Zsofia [1 ]
Szantay, Csaba, Jr. [1 ]
机构
[1] Chem Works Gedeon Richter Plc, API Res & Dev Spectroscop Res, NMR Lab, H-1475 Budapest 10, Hungary
[2] Chem Works Gedeon Richter Plc, API Res & Dev Spectroscop Res, MS Lab, H-1475 Budapest 10, Hungary
关键词
Bisindole; Structure determination; NMR; MS; Historical scope; INDIRECT COVARIANCE NMR; DIMERIC CATHARANTHUS ALKALOIDS; NATURALLY-OCCURRING SUBSTANCES; VINCA ALKALOIDS; DEGRADATION-PRODUCTS; IN-VITRO; MASS-SPECTRA; LEUROCRISTINE VINCRISTINE; METABOLIC TRANSFORMATIONS; CHEMICAL CHARACTERIZATION;
D O I
10.1016/j.jpba.2012.02.015
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
In this review our aim is to look back on how the structure elucidation of bisindoles, especially with focus placed on vinblastine and vincristine analogues, has evolved alongside with the development of MS and NMR over the last 60 years from the perspective of our present-day use of state-of-the-art MS and NMR instrumentation and on the basis of our own accumulated views and experience in the field. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:106 / 124
页数:19
相关论文
共 108 条
[1]   STRUCTURE ELUCIDATION AND CHEMISTRY OF CATHARANTHUS ALKALOIDS .3. STRUCTURE OF LEUROSINE, AN ACTIVE ANTICANCER ALKALOID [J].
ABRAHAM, DJ ;
FARNSWORTH, NR .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1969, 58 (06) :694-+
[2]   Oxidation of vincristine catalyzed by peroxidase and ceruloplasmin [J].
Ahn, SH ;
Duffel, MW ;
Rosazza, JPN .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (11) :1125-1129
[3]   MOLECULAR MODELING, NMR-SPECTROSCOPY, AND CONFORMATIONAL-ANALYSIS OF 3',4'-ANHYDROVINBLASTINE [J].
ANDREWS, CW ;
WISOWATY, J ;
DAVIS, AO ;
CROUCH, RC ;
MARTIN, GE .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) :1011-1017
[4]  
[Anonymous], 2011, VINBL SULF VINCR SUL
[5]   ANALYSIS OF INDOLE ALKALOIDS FROM LEAVES OF CATHARANTHUS-ROSEUS BY MEANS OF SUPERCRITICAL FLUID CHROMATOGRAPHY/MASS SPECTROMETRY [J].
BALSEVICH, J ;
HOGGE, LR ;
BERRY, AJ ;
GAMES, DE ;
MYLCHREEST, IC .
JOURNAL OF NATURAL PRODUCTS, 1988, 51 (06) :1173-1177
[6]   Synthesis and in Vitro Antitumor Effect of Vinblastine Derivative-Oligoarginine Conjugates [J].
Banoczi, Zoltan ;
Gorka-Kereskenyi, Almos ;
Remenyi, Judit ;
Orban, Erika ;
Hazai, Laszlo ;
Tokesi, Natalia ;
Olah, Judit ;
Ovadi, Judit ;
Beni, Zoltan ;
Hada, Viktor ;
Szantay, Csaba, Jr. ;
Hudecz, Ferenc ;
Kalaus, Gyoergy ;
Szantay, Csaba .
BIOCONJUGATE CHEMISTRY, 2010, 21 (11) :1948-1955
[7]   STRUCTURE-ACTIVITY-RELATIONSHIPS OF DIMERIC CATHARANTHUS ALKALOIDS .1. DEACETYLVINBLASTINE AMIDE (VINDESINE) SULFATE [J].
BARNETT, CJ ;
CULLINAN, GJ ;
GERZON, K ;
HOYING, RC ;
JONES, WE ;
NEWLON, WM ;
POORE, GA ;
ROBISON, RL ;
SWEENEY, MJ ;
TODD, GC ;
DYKE, RW ;
NELSON, RL .
JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (01) :88-96
[8]   Crystal structure of vinblastine [J].
Bau, R ;
Jin, KK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (13) :2079-2082
[9]  
BIEMANN K, 1964, LLOYD, V27, P397
[10]   STUDIES ON THE STABILITY OF VINBLASTINE SULFATE IN AQUEOUS-SOLUTION [J].
BLACK, J ;
BUECHTER, DD ;
CHINN, JW ;
GARD, J ;
THURSTON, DE .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1988, 77 (07) :630-634