title: Are spirolides converted in biological systems?--A study.
abstract: 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.
authors.affiliation: Institute for Nutrition, Friedrich-Schiller-University, Dornburger Strabe 25, D-07749 Jena, Germany. blchbe@uni-jena.de
authors.forename: Bernd
authors.initials: B
authors.lastname: Christian
authors.forename: Anja
authors.initials: A
authors.lastname: Below
authors.forename: Nicole
authors.initials: N
authors.lastname: Drebler
authors.forename: Olaf
authors.initials: O
authors.lastname: Scheibner
authors.forename: Bernd
authors.initials: B
authors.lastname: Luckas
authors.forename: Gunnar
authors.initials: G
authors.lastname: Gerdts
mesh_terms: 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*
chemical_list: D007783:Lactones; D013141:Spiro Compounds