title: Structure and stereochemistry of a new cytotoxic polychlorinated sulfolipid from Adriatic shellfish.
abstract: A detailed analysis of the causative toxins contained in the hepatopancreas of toxic mussels from the northern Adriatic sea has been carried out. Along with some DSP (diarrhetic shellfish poisoning) type toxins, such as okadaic acid, yessotoxin, and their derivatives, which are involved in a number of human intoxications throughout the world, we have now isolated a new cytotoxin, a polychlorinated sulfolipid 1, whose gross structure has been elucidated by spectral analysis, including various 2D NMR techniques. The relative stereochemistry of 1 was elucidated by successful application of the J-based configuration analysis developed for acyclic compounds using carbon-proton spin-coupling constants ((2,3)J(C,H)) and proton-proton spin-coupling constants ((3)J(H,H)); its absolute stereochemistry was established by the Mosher method. Compound 1 possesses in vitro cytotoxicity against WEHI 164 and RAW 264.7 cells.
authors.affiliation: Dipartimento di Chimica delle Sostanze Naturali, Università degli studi di Napoli Federico II, via D. Montesano 49, 80131, Napoli, Italy. ciminiel@unima.it
authors.forename: Patrizia
authors.initials: P
authors.lastname: Ciminiello
authors.forename: Carmela
authors.initials: C
authors.lastname: Dell'Aversano
authors.forename: Ernesto
authors.initials: E
authors.lastname: Fattorusso
authors.forename: Martino
authors.initials: M
authors.lastname: Forino
authors.forename: Silvana
authors.initials: S
authors.lastname: Magno
authors.forename: Massimo
authors.initials: M
authors.lastname: Di Rosa
authors.forename: Angela
authors.initials: A
authors.lastname: Ianaro
authors.forename: Roberto
authors.initials: R
authors.lastname: Poletti
mesh_terms: D000818:Animals; D049872:Bivalvia / Q000737:chemistry / Q000378:metabolism; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry*; D008387:Marine Toxins / Q000737:chemistry*; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D006843:Hydrocarbons, Chlorinated; D008055:Lipids; D008387:Marine Toxins; C015518:sulfolipids