Abstract
Bioassay-guided partition of the extract of the Red Sea sponge Pseudoceratina arabica and HPLC purification of the active fraction gave a psammaplysin dimer, psammaceratin A (1), along with psammaplysin A (2). The dimer comprises two units of psammaplysin A (2) connected via the terminal amines with an unprecedented (2Z,3Z)-2,3-bis(aminomethylene)succinamide moiety, and it represents the first dimer to be identified among the psammaplysin family. Data from 1D- and 2D-NMR and HRMS supported the chemical structures of the compounds. Psammaceratin A (1) and psammaplysin A (2) exhibited significant growth inhibition of HCT 116, HeLa, and MBA-MB-231 cells down to 3.1 μM.
Highlights
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Compounds with the dibrominated spirooxepinisoxazoline moiety are reported under different names, including psammaplysins [2,3,4,5,6,7,8,9,10,11,12,13], ceratinamides [12,13,14], ceratinadins [15], and frondoplysins [16]
Spirooxepinisoxazoline derivatives originate mainly from members of the order Verongiida [4,5,6,7,8,9,10,11,12,13], with only two sponges belonging to the Dictyoceratida order [14,15,16]
Summary
Verongid sponges are considered a main source of bioactive brominated alkaloids that originate from bromotyrosine [1,2,3]. These marine alkaloids include a large and structurally diverse class of compounds such as psammaplysins (spirooxepinisoxazolines), bastadins, spirocyclohexadienylisoxazolines, oximes, and others [1,2,3]. Compounds with the dibrominated spirooxepinisoxazoline moiety are reported under different names, including psammaplysins [2,3,4,5,6,7,8,9,10,11,12,13], ceratinamides [12,13,14], ceratinadins [15], and frondoplysins [16]. Spirooxepinisoxazoline derivatives originate mainly from members of the order Verongiida [4,5,6,7,8,9,10,11,12,13], with only two sponges belonging to the Dictyoceratida order [14,15,16]
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