Intramolecular interchain reactions in bidesmosidic glycosides, a new insight into carbohydrate rearrangements induced by electrospray ionisation

被引:9
作者
Dal Piaz, Fabrizio
De Leo, Marinella
Braca, Alessandra
De Simone, Francesco
De Tommasi, Nunziatina
机构
[1] Univ Salerno, Dipartimento Sci Farmaceut, I-84084 Fisciano, SA, Italy
[2] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy
关键词
D O I
10.1002/rcm.2839
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Glycoconjugates are a class of complex molecules that are widely distributed in the plant kingdom and in some marine organisms. This class of compounds has a wide range of biological activities such as anti-inflammatory, antimicrobial, antifungal, anticancer, antiulcer, and immunoenhancing actions.(1-3) Some of them also show various toxic activities such as cytotoxic, hemolytic, cardiotoxic, and teratogenic. Among these compounds, steroidal and triterpenoid saponins have long been known as components of widely used herbal drugs and pharmaceutical preparations; ginseng, Tribulus terrestris, Quillaja saponaria, and Digitalis ssp. are just a few examples. Thus, identification of saponins in herbal drugs used worldwide is of significance in phytochemical and toxicological quality control studies, and for the production of safe health products. Therefore, there is continuing demand for methods to rapidly identify and characterize these natural products. Copyright (c) 2007 John Wiley & Sons, Ltd.
引用
收藏
页码:286 / 296
页数:11
相关论文
共 27 条
[1]   New pregnane glycosides from Caralluma negevensis [J].
Braca, A ;
Bader, A ;
Morelli, I ;
Scarpato, R ;
Turchi, G ;
Pizza, C ;
De Tommasi, N .
TETRAHEDRON, 2002, 58 (29) :5837-5848
[2]   Loss of internal 1->6 substituted monosaccharide residues from underivatized and per-O-methylated trisaccharides [J].
Brull, LP ;
Heerma, W ;
ThomasOates, J ;
Haverkamp, J ;
Kovacik, V ;
Kovac, P .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 1997, 8 (01) :43-49
[3]  
Brull LP, 1998, RAPID COMMUN MASS SP, V12, P1520
[4]   Electrospray ionization mass spectrometry for identification and structural characterization of pregnane glycosides [J].
Dal Piaz, F ;
De Leo, M ;
Braca, A ;
De Simone, F ;
Morelli, I ;
De Tommasi, N .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 2005, 19 (08) :1041-1052
[5]   A SYSTEMATIC NOMENCLATURE FOR CARBOHYDRATE FRAGMENTATIONS IN FAB-MS MS SPECTRA OF GLYCOCONJUGATES [J].
DOMON, B ;
COSTELLO, CE .
GLYCOCONJUGATE JOURNAL, 1988, 5 (04) :397-409
[6]   Measuring the metabolome: current analytical technologies [J].
Dunn, WB ;
Bailey, NJC ;
Johnson, HE .
ANALYST, 2005, 130 (05) :606-625
[7]   False sugar sequence ions in electrospray tandem mass spectrometry of underivatized sialyl-Lewis-type oligosaccharides [J].
Ernst, B ;
Muller, DR ;
Richter, WJ .
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES, 1997, 160 (1-3) :283-290
[8]   Evidence for long-range glycosyl transfer reactions in the gas phase [J].
Franz, AH ;
Lebrilla, CB .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2002, 13 (04) :325-337
[9]   Metabolomic applications of electrochemistry/mass spectrometry [J].
Gamache, PH ;
Meyer, DF ;
Granger, MC ;
Acworth, IN .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2004, 15 (12) :1717-1726
[10]   A STEREOCHEMICAL BRIDGE BETWEEN MASS-SPECTROMETRY AND FREE-RADICAL CHEMISTRY [J].
GREEN, MM .
TETRAHEDRON, 1980, 36 (19) :2687-2699