Are spirolides converted in biological systems?--A study.
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.
Christian
Bernd
B
Institute for Nutrition, Friedrich-Schiller-University, Dornburger Strabe 25, D-07749 Jena, Germany. blchbe@uni-jena.de
Below
Anja
A
Drebler
Nicole
N
Scheibner
Olaf
O
Luckas
Bernd
B
Gerdts
Gunnar
G
D000818:Animals; D002474:Cell-Free System; D049896:Crassostrea / Q000378:metabolism; D004141:Dinoflagellida / Q000378:metabolism; D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D049880:Mytilus edulis / Q000378:metabolism; D049910:Pecten / Q000378:metabolism; D013141:Spiro Compounds / Q000737:chemistry / Q000378:metabolism*
D007783:Lactones; D013141:Spiro Compounds