Callyspongins A and B:  Novel Polyacetylene Sulfates from the Marine Sponge Callyspongia truncata That Inhibit Fertilization of Starfish Gametes

Abstract

Bioassay-guided fractionation of the fertilization-inhibitory constituents of the marine sponge Callyspongia truncata yielded two novel polyacetylene sulfates designated callyspongins A (1) and B (2). The structures were determined on the basis of spectroscopic data. Compounds 1 and 2 inhibited fertilization of starfish gametes with minimum inhibitory concentrations of 6.3 and 50 μM, respectively, but affected neither maturation of oocytes nor cell division of embryos. These findings indicate that the sulfate group plays an important role in specific inhibition of starfish fertilization.

Biosynthesis and function of polyacetylenes and allied natural products

“…39) [403]. Callyspongins A and B (35U-V) specifically interfered with oocyte fertilization membrane formation at concentrations of 6.3 and 50 μM (MIC), respectively, without affecting embryo and egg development [403]. The stereochemistry of 35U matched that of the known non-sulfonated metabolite siphonodiol 35T [404].…”

“…and C. truncata (Fig. 39) [403]. Callyspongins A and B (35U-V) specifically interfered with oocyte fertilization membrane formation at concentrations of 6.3 and 50 μM (MIC), respectively, without affecting embryo and egg development [403].…”

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

“…Although several natural inhibitors of echinoderm fertilization have been obtained from marine organisms, e.g., jaspisin, 13,15) callyspongins A and B, 16) and halenaquinol sulfate, 29,30) all of them inhibit sperm-egg fusion, but do not affect sperm motility. There are very few, if any, selective inhibitors of sperm motility.…”

“…[1][2][3] Some of them exhibit antimalarial, [4][5][6][7] antifouling, 8,9) antimicrobial, 10) antifungal, 11) and antiparasitic 12) activities. In our continuing search for selective inhibitors of echinoderm fertilization and of embryonic development from marine organisms, [13][14][15][16] we have isolated new spirocyclic sesquiterpenes, (À)-10-epi-axisonitrile-3 (1), exiguamide (2), exicarbamate (3), and exigurin (4), from the marine sponge Geodia exigua Thiele, and have reported the inhibitory activity of 2 on the spicule formation of sea urchin. 17,18) Further investigation of the biological activity of spirocyclic sesquiterpenes revealed that 1 potently inhibits fertilization of sea urchin and starfish gametes by immobilizing sperm without affecting the embryogenesis of the fertilized eggs.…”

Polyacetylene diols with antiproliferative and driving Th1 polarization effects from the marine sponge Callyspongia sp.

“…,K ? -ATPase inhibitory activity, antitumor activity, inhibition of fertilization in the starfish Asterina pectinifera, and anti-HIV activity [1][2][3][4][5][6][7][8][9].…”