Ulososides and Urabosides — Triterpenoid Saponins from the Caribbean Marine Sponge Ectyoplasia ferox

Abstract

Three new triterpene glycosides, named ulososide F (1), urabosides A (2) and B (3), together with the previously reported ulososide A (4), were isolated from the Caribbean marine sponge Ectyoplasia ferox. Their structures were elucidated using extensive interpretation of 1D and 2D-NMR data, as well as HRESIMS. The aglycon of all compounds is a rare 30-norlonastane and the sugar residues were identified after acid hydrolysis and GC analyses. Cytotoxicities of the isolated compounds were evaluated against Jurkat and CHO cell lines by a MTT in vitro assay as well as a hemolysis assay. Unexpectedly, all these saponin derivatives showed very low activity in our bioassays.

HPLC-ESI-IT-MS/MS Analysis and Biological Activity of Triterpene Glycosides from the Colombian Marine Sponge Ectyoplasia ferox

“…This approach for molecular structure identification using fragmentation patterns derived from MS 2 and MS 3 measurements indicated that the detected ions at m / z 851 ( 2 ), 716 ( 6 ) and 849 ( 18 ) are consistent with ulososide A, uloloside D and uraboside B, respectively (Figure 4), in comparison with previous reports for these compounds [10,19,20]. The precursor ion at m / z 851 was detected at three different retention times (45.1, 46.4 and 48.0 min), however, the identification of ulososide A as the peak at 46.4 min, did not represent a problem due to its fragmentation pattern (Figure 4A).…”

“…[17], described four different saponins for E. ferox such as: Ectyoplaside A ([M + Na] + : m / z 953), Ectyoplaside B ([M + Na] + : m / z 969), Feroxoside A ([M + Na] + : m / z 1099) and Feroxoside B ([M + Na] + : m / z 1101). Those authors described the molecular structures of these saponins; however, it was also possible to determine in a previous report strong structural differences between triterpenoid skeletons of saponins from the Colombian sponge compared to that initially discovered from the Bahamas [10]. The saponins reported were: ulososide A ([M + Na] + : m / z 851), ulososide F ([M + Na] + : m / z 892), uraboside A ([M + Na] + : m / z 953) and uraboside B ([M + Na] + : m / z 849).…”

Marine natural products

“…749,750 Finally, ulososide F 795, urabosides A 796 and B 797 are triterpene saponins from Ectyoplasia ferox (Caribbean Sea, Colombia), with 797 being the rst reported compound with both C-4 methyls elevated to the carboxylic acid oxidation state. 751…”

Chemical Components and Bioactive of Gorgonian Sea Plumes (Genus Rumphella and Hicksonella) from Raijua Islands-East Nusa Tenggara

“…; Nephthea chabrolii (Wang et al 2012; Triterpenoid terdeteksi pada ekstrak etil asetet, n-heksana dan metanol pada kulit dan aksial ekstrak akar bahar. Penelitian Chung et al (2013;2014) menyatakan bahwa pada Rumphella antipathies dari campuran pelarut methanol dan diklorometan juga menemukan senyawa triterpenoid dari golongan seskuiterpenoid yaitu rumphellclovanes C-E dari dan 4,5-seco-caryophyllane yaitu rumphellaones B dan C. Colorado et al (2013) juga melaporkan mengisolasi tiga senyawa baru triterpen glikosida dari sponge Ectyoplasia ferox menggunakan pelarut methanol dan diklorometana.…”