SIPHONODIOL, A NEW POLYACETYLENIC METABOLITE FROM THE SPONGE SIPHONOCHALINA TRUNCATE

Abstract

A new C23 polyacetylene diol was isolated from the marine sponge S. truncata and its structure was elucidated mainly on the basis of its spectral data.

Biosynthesis and function of polyacetylenes and allied natural products

“…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]. The more highly saturated C 24 enyne callysponginol sulfate A (40S) was found to be a membrane type 1 matrix metalloproteinase inhibitor (Fig.…”

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

“…The 12Z,19Z-configuration was determined by 1 H coupling constants (J 12,13 = 10.7 Hz and J 19,20 = 11.0 Hz). The configuration of compound 1 at C-2 was assigned R by comparison of the [a] D value of (R)-(-)-siphonodiol (2) with that of (S)-(? )- .…”

“…,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].…”

“…Bioassayguided fractionation was applied to the active EtOAcsoluble extract obtained from the sponge. The major compounds of the most active fraction were identified as callyspongidiol (1), siphonodiol (2), and 14,15-dihydrosiphonodiol (3) [2,3]. The structure of callyspongidiol (1) was determined by detailed spectroscopic analyses.…”

<i>In vitro</i> Cytotoxic, Antibacterial and Antiviral Activities of Triterpenes from the Red Sea Sponge, <i>Siphonochalina siphonella</i>

“…A potent hemiasterlin class of antitumor agents has been isolated from Siphonochalina spp. while an antifungal and antibacterial polyacetylene diol, siphonodiol, was reported from the marine sponge Siphonochalina truncate [4]. On the other hand, acetylated bile acid derivatives were obtained from the organic extracts of the sponge S. fortis, collected from Argentina shores [5].…”