Are spirolides converted in biological systems? - A study

被引:16
作者
Christian, Bernd [1 ]
Below, Anja [1 ]
Dressler, Nicole [1 ]
Scheibner, Olaf [2 ]
Luckas, Bernd [1 ]
Gerdts, Gunnar [3 ]
机构
[1] Univ Jena, Inst Nutr, D-07749 Jena, Germany
[2] Hans Knoell Inst, Leiden Inst Nat Prod Res & Infect Biol, D-07745 Jena, Germany
[3] Alfred Wegener Inst Polar & Marine Res, D-27483 Helgoland, Germany
关键词
spirolides; shellfish; LC-MS analyses; Alexandrium ostenfeldii;
D O I
10.1016/j.toxicon.2007.12.019
中图分类号
R9 [药学];
学科分类号
1007 [药学];
摘要
Spirolides are biologically active macrocycles isolated first from scallops and phytoplankton from aquaculture sites in Nova Scotia. Canada. These compounds displayed "fast-acting" toxicity in the traditional bioassay. That phenomenon is related to the presence of a cyclic imine function in these compounds. Spirolides containing vicinal methyl groups in their seven-membered ring are suspected of being resistant to hydrolysis. We studied possible conversions of vicinal methyl groups wearing spirolides of Alexandrium ostenfeldii KO287 in enzymatic cell-free tissue extracts of Mytilus edulis, Pecten maximus and Crassostrea gigas. Our observations suggest that spirolides that contain an extra methyl group on the imine ring compared with spirolide A and B survive enzymatic hydrolysis conditions in shellfish and therefore may be toxic for human beings when shellfish is consumed. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:934 / 940
页数:7
相关论文
共 14 条
[1]
Detection and identification of spirolides in Norwegian shellfish and plankton [J].
Aasen, J ;
MacKinnon, SL ;
LeBlanc, P ;
Walter, JA ;
Hovgaard, P ;
Aune, T ;
Quilliam, MA .
CHEMICAL RESEARCH IN TOXICOLOGY, 2005, 18 (03) :509-515
[2]
Cembella A., 1998, Xunta de Galicia and Intergovernmental Oceanographic Commission of UNESCO., P481
[3]
The marine dinoflagellate Alexandrium ostenfeldii (Dinophyceae) as the causative organism of spirolide shellfish toxins [J].
Cembella, AD ;
Lewis, NI ;
Quilliam, MA .
PHYCOLOGIA, 2000, 39 (01) :67-74
[4]
Cembella AD, 1999, NAT TOXINS, V7, P197, DOI 10.1002/1522-7189(200009/10)7:5<197::AID-NT62>3.3.CO
[5]
2-8
[6]
Neural injury biomarkers of novel shellfish toxins, spirolides: A pilot study using immunochemical and transcriptional analysis [J].
Gill, S ;
Murphy, M ;
Clausen, J ;
Richard, D ;
Quilliam, M ;
MacKinnon, S ;
LaBlanc, P ;
Mueller, R ;
Pulido, O .
NEUROTOXICOLOGY, 2003, 24 (4-5) :593-604
[7]
Guillard R.R.L., 1975, Culture of Marine Invertebrate Animals: Proceedings, P29, DOI 10.1007/978-1-4615-8714-9_3
[8]
STUDIES OF MARINE PLANKTONIC DIATOMS .1. CYCLOTELLA NANA HUSTEDT, AND DETONULA CONFERVACEA (CLEVE) GRAN [J].
GUILLARD, RR ;
RYTHER, JH .
CANADIAN JOURNAL OF MICROBIOLOGY, 1962, 8 (02) :229-&
[9]
Characterization of biologically inactive spirolides E and F: Identification of the spirolide pharmacophore [J].
Hu, TM ;
Curtis, JM ;
Walter, JA ;
Wright, JLC .
TETRAHEDRON LETTERS, 1996, 37 (43) :7671-7674
[10]
SPIROLIDE-B AND SPIROLIDE-D, 2 NOVEL MACROCYCLES ISOLATED FROM THE DIGESTIVE GLANDS OF SHELLFISH [J].
HU, TM ;
CURTIS, JM ;
OSHIMA, Y ;
QUILLIAM, MA ;
WALTER, JA ;
WATSONWRIGHT, WM ;
WRIGHT, JLC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (20) :2159-2161