title: Stereoisomers of 42-hydroxy palytoxin from Hawaiian Palythoa toxica and P. tuberculosa: stereostructure elucidation, detection, and biological activities.
abstract: Palytoxin ranks among the most potent marine biotoxins. Its lethality was well known to native Hawaiians that used to smear a "moss" containing the toxin on their spears to cause instant death to their victims. Human intoxications due to exposure to palytoxin and to its many congeners have been reported worldwide. Currently, palytoxins constitute the main threat to public health across the Mediterranean Sea. In the present work we report on the isolation and stereostructural determination of a new palytoxin analogue from a Hawaiian Palythoa tuberculosa sample. This new toxin is a stereoisomer of 42-hydroxypalytoxin isolated from Palythoa toxica. The whole absolute configuration of this latter toxin is also reported in the paper. Interestingly, the two 42-hydroxypalytoxins do not share the same biological activity. The stereoisomer from P. tuberculosa showed cytotoxicity toward skin HaCaT keratinocytes approximately 1 order of magnitude lower than that of 42-hydroxypalytoxin from P. toxica and about 2 orders of magnitude lower than that of palytoxin itself. This finding holds the prospect of interesting structure-activity relationship evaluations in the future.
authors: Department of Pharmacy, University of Napoli "Federico II" , Via D. Montesano 49, 80131 Napoli, Italy.
authors: Patrizia
authors: P
authors: Ciminiello
authors: Carmela
authors: C
authors: Dell'Aversano
authors: Emma
authors: E
authors: Dello Iacovo
authors: Martino
authors: M
authors: Forino
authors: Luciana
authors: L
authors: Tartaglione
authors: Marco
authors: M
authors: Pelin
authors: Silvio
authors: S
authors: Sosa
authors: Aurelia
authors: A
authors: Tubaro
authors: O
authors: O
authors: Chaloin
authors: Mark
authors: M
authors: Poli
authors: Gary
authors: G
authors: Bignami
mesh_terms: D000178:Acrylamides / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003064:Cnidarian Venoms / Q000737:chemistry / Q000494:pharmacology; D006254:Hawaii; D006801:Humans; D015603:Keratinocytes / Q000187:drug effects; D008387:Marine Toxins / Q000737:chemistry* / Q000633:toxicity; D008522:Mediterranean Sea; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011714:Pyrans / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D000095702:Polyether Toxins
chemical_list: D000178:Acrylamides; D003064:Cnidarian Venoms; D008387:Marine Toxins; D011714:Pyrans; C547187:42-hydroxypalytoxin; D000095702:Polyether Toxins; C010272:palytoxin