Structure and stereochemistry of a new cytotoxic polychlorinated sulfolipid from Adriatic shellfish.
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.
Ciminiello
Patrizia
P
Dipartimento di Chimica delle Sostanze Naturali, Università degli studi di Napoli Federico II, via D. Montesano 49, 80131, Napoli, Italy. ciminiel@unima.it
Dell'Aversano
Carmela
C
Fattorusso
Ernesto
E
Forino
Martino
M
Magno
Silvana
S
Di Rosa
Massimo
M
Ianaro
Angela
A
Poletti
Roberto
R
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
D006843:Hydrocarbons, Chlorinated; D008055:Lipids; D008387:Marine Toxins; C015518:sulfolipids