Anti-Fertilization Activity of a Spirocyclic Sesquiterpene Isocyanide Isolated from the Marine SpongeGeodia exiguaand Related Compounds | Zendy

Emi Ohta | Zendy; Mylene M. Uy | Zendy; Shinji Ohta | Zendy; Mihoko Yanai | Zendy; Toshifumi Hirata | Zendy; Susumu Ikegami | Zendy

Open Access

Anti-Fertilization Activity of a Spirocyclic Sesquiterpene Isocyanide Isolated from the Marine SpongeGeodia exiguaand Related Compounds

Author(s) -

Emi Ohta,

Mylene M. Uy,

Shinji Ohta,

Mihoko Yanai,

Toshifumi Hirata,

Susumu Ikegami

Publication year - 2008

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.80071

Subject(s) - isocyanide , sponge , sea urchin , human fertilization , chemistry , sesquiterpene , sperm , phosphate , pyrophosphate , stereochemistry , biochemistry , biology , botany , anatomy , ecology , enzyme

(-)-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 microg/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 (31)P 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.

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