H,K-ATPase inhibitors from the marine sponge : Absolute configuration of siphonodiol and two related metabolites

Two New Haliclamines from the Arctic Sponge Haliclona viscosa

“…NMR spectroscopic data of haliclamine C (1) and D (2) in [D 6 ]DMSO; chemical shifts are referenced to the solvent signal ( 1 H 2.50 ppm, 13 C 39.5 ppm); for position 1, δ( 15 N) is given; 15 N NMR spectra were not calibrated with an external standard; the δ value has an accuracy of about 1 ppm in reference to NH 3 (δ ϭ 0 ppm); COSY correlations are given for both sides of the diagonal; HMBC correlations are given from protons to carbon atoms described in the literature as the haliclamines from a Haliclona sp. [18] and the cyclostellettamines from Stelletta maxima (see Figure 2). [19] The lengths of the alkyl chains are 9 and 12 (unsaturated) for the haliclamines and 12 to 14 (saturated) for cyclostellettamines.…”

Polyacetylenediols regulate the function of human monocyte-derived dendritic cells

“…induced neuritogenesis in phenochromocytoma PC 12 cells and neuroblastoma neuron 2A cells [18]. Siphonodiol and two related metabolites from siphonochalina truncata have been shown to inhibit H+, K+-ATPase [19]. Furthermore, callyspongidiol and 14,15-dihydrosiphonodiol exhibited antiproliferative activity against HL-60 [17].…”

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].…”

“…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.…”

“…As callyspongidiol (1) only differs from 2 by one CH 2 and one acetylene group, the configuration of 1 [[a] D value = -7.9°(c 1.13, MeOH)] at C-2 was consistent with being R. Thus, callyspongidiol (1) was designated as (12Z,19Z)-docosa-12,19-diene-3,5,10, 21-tetrayne-1,2(R)-diol. The known compounds 2 and 3 were also isolated, and their structures were determined on the basis of comparison of their 1 H-NMR,13 C-NMR, and HRMS spectra with literature values[2,3] (Figs. 1, 2).…”