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Anti-fertilization activity of a spirocyclic sesquiterpene isocyanide isolated from the marine sponge Geodia exigua and related compounds.

Author

Emi   Ohta,
Mylene   .  UY,
Shinji  Ohta,
Mihoko   YANAI,
Toshifumi  HIRATA,
Susumu Ikegami

Related Institution

Chemistry Department - Mindanao State University - Iligan Institute of Technology

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Publication Information

Publication Type
Journal
Publication Sub Type
Journal Article, Reprint
Title
Bioscience, Biotechnology, and Biochemistry
Publication Date
2008
Volume
72
Issue
7
Page(s)
1764-1771

Abstract

(−)-10-epi-Axisonitrile-3, a spirocyclic sesquiterpene isocyanide obtained from the marine sponge Geodia exigua, immobilized sperm of sea urchin and starfish to block fertilization at the minimum effective concentration of 0.4 μg/ml. On the other hand, fertilized eggs developed normally to the gastrula stage in the presence of a 250-times higher concentration of the isocyanide. Analysis by 31P NMR revealed an accumulation of phosphocreatine and a depletion of inorganic phosphate in the isocyanide-treated sperm, suggesting that (−)-10-epi-axisonitrile-3 inhibited the phosphocreatine shuttle participating in the high-energy phosphate metabolism, thereby immobilizing sperm to block fertilization. No analogs of (−)-10-epi-axisonitrile-3 containing different functionalities or isocyanides with different carbon skeleton exhibited such activity.

Physical Location

LocationLocation CodeAvailable FormatAvailability
Office of the Vice Chancellor for Research and Extension, Mindanao State University-Iligan Institute Technology Fulltext (Download)

 
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