Stereoisomers of 42-Hydroxy Palytoxin from Hawaiian Palythoa toxica and P. tuberculosa: Stereostructure Elucidation, Detection, and Biological Activities

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• 作者：Patrizia Ciminiello ; Carmela Dell鈥橝versano ; Emma Dello Iacovo ; Martino Forino ; Luciana Tartaglione ; Marco Pelin ; Silvio Sosa ; Aurelia Tubaro ; O. Chaloin ; Mark Poli ; Gary Bignami
• 刊名：Journal of Natural Products
• 出版年：2014
• 出版时间：February 28, 2014
• 年：2014
• 卷：77
• 期：2
• 页码：351-357
• 全文大小：332K
• 年卷期：v.77,no.2(February 28, 2014)
• ISSN：1520-6025

文摘

Palytoxin ranks among the most potent marine biotoxins. Its lethality was well known to native Hawaiians that used to smear a 鈥渕oss鈥?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鈥揳ctivity relationship evaluations in the future.